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Fructose-amino acid conjugate and other constituents from Cyperus rotundus L
Abstract
Further phytochemical study on the aerial parts of Cyperus rotundus L. led to the isolation of a fructose-amino acid conjugate, N-(1-deoxy-alpha-D-fructos-1-yl)-L-tryptophan (16) and its tautomers, in addition to n-butyl-beta-D-fructopyranoside (1), ethyl-alpha-D-glucopyranoside (2), adenosine (3), (-)-(E)-caffeoylmalic acid (4), vitexin (5), isovitexin (6), orientin (7), epiorientin (8), myricetin 3-O-beta-D-galactopyranoside (9), luteolin 7-O-beta-D-glucuronopyranoside-6''-methyl ester (10), chlorogenic acid (11), luteolin 4'-O-beta-D-glucuronopyranoside (12), luteolin 7-O-beta-D-glucuronopyranoside (13), uridine (14) and ellagic acid (15). Their structures were elucidated on the basis of spectroscopic methods. Additionally, antioxidant and alpha-amylase inhibitory activities of some of the isolated phenolic compounds were carried out.
... For example, in some countries in Asia, rhizomes are recommended for the treatment of metabolic diseases, dysentery, bronchitis, fever, and others [6,7]. In Africa, in Egyptian folk medicine, the tubers are used as an anthelmintic and for treating stomach aches [8][9][10][11]. Several authors have reported gas chromatography-mass spectrometry (GC-MS), liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS/MS), ultrahigh performance liquid chromatography-quadrupole timeof-flight mass spectrometry (UHPLC/Q-TOF-MS), molecular networking analyses, and in vitro biological activities of the crude extracts from this plant species [1,7,[12][13][14][15][16][17][18][19][20][21][22][23][24][25]. Terpenoids, flavonoids, stilbenoids, and aliphatics with potent biological activities have been identified from this herb as major compounds from previous papers . ...
... The tubers, rhizomes, and seeds are being used in perfumes, spices, and food flavoring agents in bakeries [48,49]. 3,4,5,6,7,8,9,10,11,12,13,14,15,16,17, and 18, their names and pharmacological activities are listed in Tables 1, 2, 3, 4. ...
... Nootkatone (40), solavetivone (97), and aristolone (98) isolated from this plant species were screened for their 2,2 0 -diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity using gallic acid as standard. Compound 40 had the highest radical scavenging potential (IC 50 = 4.81 μg/mL), next aristolone (98) (IC 50 = 5.28 μg/mL), and the novel NP solavetivone (97) (IC 50 = 6.82 μg/mL) as the least active Compounds 146-148 demonstrated strong antioxidant activity using the DPPH method and propyl gallate as standard [9,10]. Ferulic acid (246), luteolin (151), and (+)-catechin (153) showed lipid peroxidation induced by H 2 O 2 , in a concentration-dependent manner. ...
... Flavonoids are extensively distributed in the plant kingdom with a wide variety of biological activities, which have attracted worldwide attention (Bai et al. 2019). Flavonoids are mainly found in the rhizomes and aerial parts such as the leaves of C. rotundus (Sayed et al. 2007(Sayed et al. , 2008Ibrahim et al. 2018). Until now, a total of fifty-four flavonoids have been isolated and identified from C. rotundus, with chemical structures as displayed in the supplementary Fig. S14-18. ...
... And amentoflavone showed a significant effect on anti-uterine fibroids in pathological rat models (Ying and Bing 2016). 7,8-Dihydroxy-5,6-methylenedioxyflavone (362) was isolated from the rhizomes of C. rotundus (Zhou and Fu 2013); while vitexin (365) glucopyranoside (384) were given from the aerial parts of C. rotundus (Sayed et al. 2008;Ibrahim et al. 2018). Compounds 365-368, 370-371 and 382 exhibited significant antioxidant activities (Sayed et al. 2008), and compounds 365, 367, 371, 375, 383, and 384 possessed significant 5-lipoxygenase inhibitory activity with IC 50 values at 5.1, 4.5, 5.9, 4.0, 3.7, and 2.3 lM, respectively (Ibrahim et al. 2018). ...
... 7,8-Dihydroxy-5,6-methylenedioxyflavone (362) was isolated from the rhizomes of C. rotundus (Zhou and Fu 2013); while vitexin (365) glucopyranoside (384) were given from the aerial parts of C. rotundus (Sayed et al. 2008;Ibrahim et al. 2018). Compounds 365-368, 370-371 and 382 exhibited significant antioxidant activities (Sayed et al. 2008), and compounds 365, 367, 371, 375, 383, and 384 possessed significant 5-lipoxygenase inhibitory activity with IC 50 values at 5.1, 4.5, 5.9, 4.0, 3.7, and 2.3 lM, respectively (Ibrahim et al. 2018). As is reported, khellin (403) and visnagin (404) were reported to show strong cytotoxic activities against L5178y (mouse lymphoma cells) with ED 50 of 4.5 and 0.9 lg/mL, respectively, and also inhibit significantly the growth of the neonate larvae of the pest insect Spodoptera littoralis to exert the antifeedant activity (Sayed et al. 2007). ...
Cyperus rotundus L. has been widely used in the treatment and prevention of numerous diseases in traditional systems of medicine around the world, such as nervous, gastrointestinal systems diseases and inflammation. In traditional Chinese medicine (TCM), its rhizomes are frequently used to treat liver disease, stomach pain, breast tenderness, dysmenorrheal and menstrual irregularities. The review is conducted to summarize comprehensively the plant’s vernacular names, distribution, phytochemistry, pharmacology, toxicology and analytical methods, along with the data mining for TCM prescriptions containing C. rotundus. Herein, 552 compounds isolated or identified from C. rotundus were systematically collated and classified, concerning monoterpenoids, sesquiterpenoids, flavonoids, phenylpropanoids, phenolics and phenolic glycosides, triterpenoids and steroids, diterpenoids, quinonoids, alkaloids, saccharides and others. Their pharmacological effects on the digestive system, nervous system, gynecological diseases, and other bioactivities like antioxidant, anti-inflammatory, anti-cancer, insect repellent, anti-microbial activity, etc. were summarized accordingly. Moreover, except for the data mining on the compatibility of C. rotundus in TCM, the separation, identification and analytical methods of C. rotundus compositions were also systematically summarized, and constituents of the essential oils from different regions were re-analyzed using multivariate statistical analysis. In addition, the toxicological study progresses on C. rotundus revealed the safety property of this herb. This review is designed to serve as a scientific basis and theoretical reference for further exploration into the clinical use and scientific research of C. rotundus.
Graphical Abstract
... The rhizomes have been used in Asian traditional medicine for treating diverse inflammatory diseases (Sayed et al., 2007). Furthermore, the plant possessed different biological activities such as anti-oxidant, cytotoxic (Sayed et al., 2008;Sayed et al., 2007), antipyretic, anti-inflammatory, anti-emetic, hypotensive (Sayed et al., 2001), anticonvulsant (Mayur et al., 2011), anti-malarial, antimicrobial (Thebtaranonth et al., 1995, anti-diarrheal (Daswani et al., 2011), anti-diabetic (Sivapalan, 2013Sayed et al., 2008), hepatoprotective (Sivapalan, 2013), and insecticidal (Singh et al., 2012). The former studies of C. rotundus led to the separation of sesquiterpenes (Kim et al., 2013;Lawal and Oyedeji, 2009), flavonoids (Sayed et al., 2001;Sayed et al., 2007;Sayed et al., 2008;Krishna and Renu, 2013), phenylpropanoids, phenolic acids (Sayed et al., 2008;Zhou and Zhang, 2013;Mohamed, 2015), alkaloids (Jeong et al., 2000), and saponins (Singh and Singh, 1980). ...
... The rhizomes have been used in Asian traditional medicine for treating diverse inflammatory diseases (Sayed et al., 2007). Furthermore, the plant possessed different biological activities such as anti-oxidant, cytotoxic (Sayed et al., 2008;Sayed et al., 2007), antipyretic, anti-inflammatory, anti-emetic, hypotensive (Sayed et al., 2001), anticonvulsant (Mayur et al., 2011), anti-malarial, antimicrobial (Thebtaranonth et al., 1995, anti-diarrheal (Daswani et al., 2011), anti-diabetic (Sivapalan, 2013Sayed et al., 2008), hepatoprotective (Sivapalan, 2013), and insecticidal (Singh et al., 2012). The former studies of C. rotundus led to the separation of sesquiterpenes (Kim et al., 2013;Lawal and Oyedeji, 2009), flavonoids (Sayed et al., 2001;Sayed et al., 2007;Sayed et al., 2008;Krishna and Renu, 2013), phenylpropanoids, phenolic acids (Sayed et al., 2008;Zhou and Zhang, 2013;Mohamed, 2015), alkaloids (Jeong et al., 2000), and saponins (Singh and Singh, 1980). ...
... Furthermore, the plant possessed different biological activities such as anti-oxidant, cytotoxic (Sayed et al., 2008;Sayed et al., 2007), antipyretic, anti-inflammatory, anti-emetic, hypotensive (Sayed et al., 2001), anticonvulsant (Mayur et al., 2011), anti-malarial, antimicrobial (Thebtaranonth et al., 1995, anti-diarrheal (Daswani et al., 2011), anti-diabetic (Sivapalan, 2013Sayed et al., 2008), hepatoprotective (Sivapalan, 2013), and insecticidal (Singh et al., 2012). The former studies of C. rotundus led to the separation of sesquiterpenes (Kim et al., 2013;Lawal and Oyedeji, 2009), flavonoids (Sayed et al., 2001;Sayed et al., 2007;Sayed et al., 2008;Krishna and Renu, 2013), phenylpropanoids, phenolic acids (Sayed et al., 2008;Zhou and Zhang, 2013;Mohamed, 2015), alkaloids (Jeong et al., 2000), and saponins (Singh and Singh, 1980). Continuing the phytochemical study on C. rotundus rhizomes, the current work reported the separation and identification of a new norterpenoid with an unprecedented carbon skeleton: cyperalin A (1), in addition to sugetriol triacetate (2) (fig. ...
Phytochemical investigation of the methanolic extract of Cyperus rotundus L. (Cyperaceae) rhizomes afforded a new norterpenoid with an unprecedented carbon skeleton, namely cyperalin A (1) and sugetriol triacetate (2). Their structures were identified by using advanced spectroscopic technique such as UV, IR, 1D (1H and 13C), 2D (1H-1HCOSY, HSQC, HMBC, and NOESY) NMR, and HRESIMS as well as comparison with literature data. The isolated compounds were evaluated for their anti-inflammatory activity. Compound 1 displayed the highest inhibitory activity of PGE2, COX-2, and LOX-5 with IC50s 0.22, 1.03, and 1.37 µM, respectively compared to indomethacin (IC50s 0.15, 0.69, and 0.81 μM, respectively). Moreover, 2 demonstrated significant activity with IC50s 0.57 (PGE2), 1.74 (COX-2) and 2.03 (LOX-5) μM.
... Also, tubers are used as a remedy for various ailments such as fever, dysentery, diarrhea, cholera, and renal colic (Boulos, 1983). Furthermore, the plant possessed varied bioactivities: cytotoxicity (Sayed et al., 2007(Sayed et al., , 2008, antioxidant (Nagulendran et al., 2007), anti-inflammatory, antipyretic, hypotensive, antiemetic (Sayed et al., 2001), anti-allergic (Meena et al., 2010;Jin et al., 2011), anticonvulsant (Mayur et al., 2011), anti-diarrheal (Daswani et al., 2011), anti-malarial, antimicrobial (Ahmad et al., 2012), hepatoprotective (Mohamed, 2015), insecticidal (Singh et al., 2012), and anti-diabetic (Bawden et al., 2002;Sayed et al., 2008). The former phytochemical researches on C. rotundus revealed the existence of sesquiterpenes (Bawden et al., 2002;Xu et al., 2008;Lawal and Oyedeji, 2009;Kim et al., 2013), saponins (Singh and Singh, 1980), alkaloids (Jeong et al., 2000), flavonoids (Sayed et al., 2001(Sayed et al., , 2007(Sayed et al., , 2008Krishna and Renu, 2013), phenylpropanoids (Sayed et al., 2008;Zhou and Zhang, 2013), phenolic acids (Sayed et al., 2008), and iridoid glycosides (Zhou and Zhang, 2013;Mohamed, 2015). ...
... Also, tubers are used as a remedy for various ailments such as fever, dysentery, diarrhea, cholera, and renal colic (Boulos, 1983). Furthermore, the plant possessed varied bioactivities: cytotoxicity (Sayed et al., 2007(Sayed et al., , 2008, antioxidant (Nagulendran et al., 2007), anti-inflammatory, antipyretic, hypotensive, antiemetic (Sayed et al., 2001), anti-allergic (Meena et al., 2010;Jin et al., 2011), anticonvulsant (Mayur et al., 2011), anti-diarrheal (Daswani et al., 2011), anti-malarial, antimicrobial (Ahmad et al., 2012), hepatoprotective (Mohamed, 2015), insecticidal (Singh et al., 2012), and anti-diabetic (Bawden et al., 2002;Sayed et al., 2008). The former phytochemical researches on C. rotundus revealed the existence of sesquiterpenes (Bawden et al., 2002;Xu et al., 2008;Lawal and Oyedeji, 2009;Kim et al., 2013), saponins (Singh and Singh, 1980), alkaloids (Jeong et al., 2000), flavonoids (Sayed et al., 2001(Sayed et al., , 2007(Sayed et al., , 2008Krishna and Renu, 2013), phenylpropanoids (Sayed et al., 2008;Zhou and Zhang, 2013), phenolic acids (Sayed et al., 2008), and iridoid glycosides (Zhou and Zhang, 2013;Mohamed, 2015). ...
... Furthermore, the plant possessed varied bioactivities: cytotoxicity (Sayed et al., 2007(Sayed et al., , 2008, antioxidant (Nagulendran et al., 2007), anti-inflammatory, antipyretic, hypotensive, antiemetic (Sayed et al., 2001), anti-allergic (Meena et al., 2010;Jin et al., 2011), anticonvulsant (Mayur et al., 2011), anti-diarrheal (Daswani et al., 2011), anti-malarial, antimicrobial (Ahmad et al., 2012), hepatoprotective (Mohamed, 2015), insecticidal (Singh et al., 2012), and anti-diabetic (Bawden et al., 2002;Sayed et al., 2008). The former phytochemical researches on C. rotundus revealed the existence of sesquiterpenes (Bawden et al., 2002;Xu et al., 2008;Lawal and Oyedeji, 2009;Kim et al., 2013), saponins (Singh and Singh, 1980), alkaloids (Jeong et al., 2000), flavonoids (Sayed et al., 2001(Sayed et al., , 2007(Sayed et al., , 2008Krishna and Renu, 2013), phenylpropanoids (Sayed et al., 2008;Zhou and Zhang, 2013), phenolic acids (Sayed et al., 2008), and iridoid glycosides (Zhou and Zhang, 2013;Mohamed, 2015). Resuming the phytochemical study on C. rotundus, a new flavanol glucoside: cyperaflavoside (5) and five known flavonoids (1-4 and 6) were separated and characterized. ...
Cyperus rotundus L. (Suada, Sueda, family: Cyperaceae) is vastly spread in several world's subtropical and tropical regions. It had variable traditional uses and bioactivities. A new flavonol derivative: cyperaflavoside (myricetin 3,3′,5′-trimethyl ether 7-O-β-D-glucopyranoside) and five flavonoids: vitexin, orientin, cinaroside, quercetin 3-O-β-D-glucopyranoside, and myrcetin 3-O-β-D-glucopyranoside were separated from the methanolic extract of C. rotundus aerial parts. Their structures were verified based on UV, IR, NMR (1D and 2D), HRESIMS, and comparison with literature. All metabolites were assessed for their 5-lipoxygenase inhibitory potential. All compounds possessed 5-lipoxygenase inhibitory potentials with IC50s 5.1, 4.5, 5.9, 4.0, 3.7, and 2.3 μM, respectively, in comparison to indomethacin (IC50 0.98 μM). These results supported the traditional uses of C. rotundus in treating inflammation and its related symptoms.
... 1 Also, they are used as a remedy for renal colic and dysentery. 2 Furthermore, the plant possesses different biological activities such as antioxidant, [3][4][5] cytotoxic, 3,5 anti-allergic, 6,7 antipyretic, anti-inflammatory, antiemetic, hypotensive, 8 anticonvulsant, 9 anti-malarial, antimicrobial, 10,11 anti-diarrhoeal, 12 anti-diabetic, 5,13,14 hepatoprotective, 14,15 and insecticide. 16,17 The previous phytochemical studies of C. rotundus L. led to the isolation of sesquiterpenes, 13,[18][19][20][21][22][23] flavonoids, 3,5,8,24,25 phenylpropanoids, 5,26,27 phenolic acids, 5,26 alkaloids, 28 and saponins. ...
... 1 Also, they are used as a remedy for renal colic and dysentery. 2 Furthermore, the plant possesses different biological activities such as antioxidant, [3][4][5] cytotoxic, 3,5 anti-allergic, 6,7 antipyretic, anti-inflammatory, antiemetic, hypotensive, 8 anticonvulsant, 9 anti-malarial, antimicrobial, 10,11 anti-diarrhoeal, 12 anti-diabetic, 5,13,14 hepatoprotective, 14,15 and insecticide. 16,17 The previous phytochemical studies of C. rotundus L. led to the isolation of sesquiterpenes, 13,[18][19][20][21][22][23] flavonoids, 3,5,8,24,25 phenylpropanoids, 5,26,27 phenolic acids, 5,26 alkaloids, 28 and saponins. ...
... 2 Furthermore, the plant possesses different biological activities such as antioxidant, [3][4][5] cytotoxic, 3,5 anti-allergic, 6,7 antipyretic, anti-inflammatory, antiemetic, hypotensive, 8 anticonvulsant, 9 anti-malarial, antimicrobial, 10,11 anti-diarrhoeal, 12 anti-diabetic, 5,13,14 hepatoprotective, 14,15 and insecticide. 16,17 The previous phytochemical studies of C. rotundus L. led to the isolation of sesquiterpenes, 13,[18][19][20][21][22][23] flavonoids, 3,5,8,24,25 phenylpropanoids, 5,26,27 phenolic acids, 5,26 alkaloids, 28 and saponins. 29 In 2013 Zhou and Zhang reported the isolation of iridoid glycosides from C. rotundus rhizomes. ...
On continuation of the phytochemical investigation of the MeOH extract of Cyperus rotundus L. Rhizomes, four compounds namely, methyl 3,4-dihydroxy benzoate (1), ipolamiide (2), 6β-hydroxyipolamiide (3), and rutin (4) were isolated. Their structures were established on the basis of 1D and 2D NMR spectroscopic analyses as well as ESIMS spectral data. Compounds 2 and 3 are reported here for the first time from the genus Cyperus and 1 for the first time from the plant. Co-treatment of CCl4 hepatic injured rats with the total MeOH extract (TME) and EtOAc fraction significantly restored the hepatic marker enzymes and total bilirubin to near-normal values compared to silymarin (reference drug).
... Luteolin 3′-methyl ether Sayed et al. (2001) Luteolin 7, 3′-dimethyl ether Sayed et al. (2007) Luteolin 5, 3′-dimethyl ether Sayed et al. (2007) Luteolin 7-glucuronide Sayed et al. (2007) Luteolin 4′-glucoside Sayed et al. Alkaloids Rotundine A Jeong et al. (2000) Rotundine B Jeong et al. (2000) Rotundine C Jeong et al. (2000) Phenolic acids Gallic acid Jahan et al. (2013) Chlorogenic acid Jahan et al. (2013) Caffeic acid Jahan et al. (2013) p-Coumaric acid Jahan et al. (2013) Loganic acid Ferulic acid Jahan et al. (2013) Li (2014) Ellagic acid Sayed et al. (2008) Iridoides, benzodihydrofurans, and miscellaneous: Rotunduside A Zhou and Rotunduside B Zhou and Zhang (2013) Rotunduside C Zhang et al. 1 [ n-Butyl-β-D-fructopyranoside Sayed et al. (2008) Ethyl-α-D-glucopyranoside Sayed et al. (2008) Trans-(2-chlorovinyl) dimethylethoxysilane Aeganathan et al. (2015) 5-hydroxymethyl furfural Aeganathan et al. Table 5 (continued ) ...
... Luteolin 3′-methyl ether Sayed et al. (2001) Luteolin 7, 3′-dimethyl ether Sayed et al. (2007) Luteolin 5, 3′-dimethyl ether Sayed et al. (2007) Luteolin 7-glucuronide Sayed et al. (2007) Luteolin 4′-glucoside Sayed et al. Alkaloids Rotundine A Jeong et al. (2000) Rotundine B Jeong et al. (2000) Rotundine C Jeong et al. (2000) Phenolic acids Gallic acid Jahan et al. (2013) Chlorogenic acid Jahan et al. (2013) Caffeic acid Jahan et al. (2013) p-Coumaric acid Jahan et al. (2013) Loganic acid Ferulic acid Jahan et al. (2013) Li (2014) Ellagic acid Sayed et al. (2008) Iridoides, benzodihydrofurans, and miscellaneous: Rotunduside A Zhou and Rotunduside B Zhou and Zhang (2013) Rotunduside C Zhang et al. 1 [ n-Butyl-β-D-fructopyranoside Sayed et al. (2008) Ethyl-α-D-glucopyranoside Sayed et al. (2008) Trans-(2-chlorovinyl) dimethylethoxysilane Aeganathan et al. (2015) 5-hydroxymethyl furfural Aeganathan et al. Table 5 (continued ) ...
... The method is based on the a-amylase assay of the EnzCheck 1 Ultra Amylase Assay Kit (E33651). The DQ starch and a-amylase enzyme solutions were diluted with buffer (pH 6.9)252627. Each compound (10 mL/50 mg in DMSO), 50 mL of enzyme, and 40 mL of the buffer were added to the microplate wells and left for 5 min at 37°C, and DQ starch (100 mL) was then added. ...
... Hydrogen bonds and hydrophobic Starch/Stärke 2015, 67, 976–984 Minutaside A, new a-amylase inhibitor contacts were the most important types of interactions with the enzyme. The presence of free hydroxyl groups increased the a-amylase inhibitory activity as in 1, 4, and 5 [26, 27]. The methoxylation and/or glycosylation of the hydroxyl groups in flavonoids decreased their binding affinities to aamylase , as occurred in 2 and 3. Decreasing the hydrogen bond acceptor/donor numbers and hydrogen bonding played an important role in the binding of flavonoids to a-amylase [45]. ...
Investigation of the EtOAc fraction of Tagetes minuta L. (Asteraceae) aerial parts has afforded a
new flavonol glucoside, minutaside A (quercetagetin 6-O-(6-O-hexanoyl)-b-D-glucopyranoside)
(1), together with four known flavonoids: axillarin 7-O-b-D-glucopyranoside (2), quercetagetin
3,7-dimethoxy-6-O-b-D-glucopyranoside (3), quercetagetin 7-methoxy-6-O-b-D-glucopyranoside
(4), and quercetagetin 6-O-b-D-glucopyranoside (5). Their structures were established by
multiple spectroscopic methods in addition to HRESIMS (high-resolution electrospray
ionisation mass spectra) and comparison with literature data. The antioxidant and anti-diabetic
activities of the isolated flavonoids were evaluated using 2,2-diphenyl-1-picrylhydrazyl (DPPH)
and a-amylase inhibition assays. Compounds 1 and 5 showed significant antioxidant activity
(84.1 and 83.0% at a 20 mM dose, respectively). Compounds 1, 4, and 5 exhibited strong aamylase inhibitory activity compared with acarbose (a reference a-amylase inhibitor). However, 2 and 3 showed moderate activity. Molecular modeling studies of 1–5 that included docking, flexible alignment, and surface mapping were performed to evaluate their recognition profile aamylase receptor. In docking simulations, 5 displayed a binding mode similar to that of acarbose in the active site of a-amylase enzyme.
... The aerial parts of C. rotundus showed antihyperglycemic effects via inhibition of protein glycation in a fructosemediated model . Several flavonoids isolated from C. rotundus aerial parts inhibited a-amylase (Sayed et al., 2008). ...
... Consistent with these reports, our results indicated that the inhibitory effects of scirpusin B (4) against a-glucosidase were stronger than those of the less hydroxylated derivative, scirpusin A. The a-glucosidase inhibition may contribute to the blood glucose-lowering effect of scirpusin B in the glycogen-loaded mouse model reported previously by Kobayashi et al. (2006). Although the a-amylase inhibitory activity of the aerial parts of C. rotundus has been reported (Sayed et al., 2008), this is the first study of the effects of C. rotundus rhizomes on a-amylase and a-glucosidase activities. These results may contribute to characterization of the antidiabetic properties of C. rotundus extract Raut & Gaikwad, 2006). ...
Context:
A methanol extract of Cyperus rotundus L. (Cyperaceae) rhizomes showed inhibitory activity against α-glucosidase and α-amylase, two enzymes involve in carbohydrate digestion.
Objective:
Identification of compounds from C. rotundus rhizomes responsible for the inhibition of α-glucosidase and α-amylase.
Materials and methods:
Compounds were identified by a phytochemical investigation using combined chromatographic and spectroscopic methods. α-glucosidase and α-amylase inhibitory activities were evaluated by in vitro enzyme inhibition assays.
Results:
A new (2RS,3SR)-3,4',5,6,7,8-hexahydroxyflavane (1), together with three known stilbene dimers cassigarol E (2), scirpusin A (3) and B (4) were isolated. Compound 2 inhibited both α-glucosidase and α-amylase activities while the flavane 1 only showed effect on α-amylase, and compounds 3 and 4 were active on α-glucosidase. All four compounds showed significant 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging activity.
Discussion:
The inhibitory activities against α-amylase and α-glucosidase of the C. rotundus rhizomes were reported for the first time. Stilbene dimers are considered as potent inhibitors of α-glucosidase and promising antihyperglycemic agents.
Conclusion:
The isolated compounds may contribute to the antidiabetic property of C. rotundus.
... etin 3-O-β-D-galactopyranoside, isovitexin, luteolin 7-O-β-Dglucuronopyranoside, luteolin 4'-O-β-D-glucuronopyranoside, myricetin 3-O-β-D-galactopyranoside, protocatechuic acid, ellagic acid, chlorogenic acid, orientin, epiorientin, isorhamnetin, luteolin 7-O-β-D-glucuronopyranoside, luteolin 4'-O-β-D-glucuronopyranoside, (_)-(E)-caffeoylmalic acid, caffeic acid, p-coumaric acid, tricin, salicylic acid vitexin, isovitexin, methanolic extract/ 3,4',5,6,7,8-hexahydroxyflavane, cassigarol E, scirpusin A and B[140,150] ...
Background: Since time immemorial, humans have identified several herbs to treat various ailments. With the advancement of science and state-of-the-art technologies, different herbal extracts and chemical constituents of herbs were identified as therapeutic targets. Cyperus rotundus, also called mustaka, is one of the most ancient herbs widely distributed in tropical and subtropical regions across the globe. The tuberous and aerial parts of the herb were identified to possess various pharmacological properties. Objectives: This review focuses on the various phytocompounds of mustaka and how these compounds exert pharmacological effects and their mode of action. The molecular and cellular effects of mustaka were also discussed based on the preclinical and clinical reports available using an array of in vitro, in vivo, and ex vivo methodologies. Methods: The information from Google Scholar, Science direct, PUBMED, were reviewed with a special focus on the mode of action of C. rotundus from the data on animal and preclinical experiments to treat various diseases. Conclusion: Based on the literature available on C. rotundus in Google Scholar, Science Direct, and PubMed, the pharmacological properties of mustaka were reviewed with a particular focus on its neuropharmacological activities. The mode of action of C. rotundus and its bioactive metabolites at the molecular biology level were demonstrated based on animal and preclinical experiments to cure various ailments. These diverse effects prove C. rotundus as a valuable traditional medicine for treating various disorders.
... It is about 10-75 cm tall, and leaves are 10-18 cm long [4]. In traditional Chinese medicine, C. rotundus rhizomes known as Xiang-Fu is used to treat women's hormone, menstrual irregulations, dysmenorrheal, and gastrointestinal problems [5][6][7]. In the Indian system of medicine, it helps in treating dysentery, amenorrhea, fever, bronchitis, leprosy, arthritis, blood disorders, dysmenorrhea, and diarrhea, etc. [8,9]. ...
Cyperus rotundus (Linn.) is a versatile plant belonging to the family Cyperaceae, used in herbal medicines worldwide to cure various human ailments. The present study attempts to analyze the profiles of flavonoids in different extracts of C. rotundus with the help of thin-layer chromatography (TLC) and high-performance thin-layer chromatographic (HPTLC) fingerprint. Flower and stem extracts of C. rotundus were screens out with the help of TLC, and the Rf values were determined. HPTLC was used to quantify the flavonoid from flower extract of a plant at a 1.0 mg/mL concentration. It revealed the occurrence of flavonoids, especially quercetin in the ethanolic extract of C. rotundus flower, by using mobile phase toluene-ethyl acetate-formic acid (3:4:2.5 v/v), on a pre-coated plate of silica gel and quantified the amount of quercetin by densitometry absorbance mode at 257 nm. The limits of detection and quantification were 30.08 & 91.16 ng/mL, and the relative standard deviation ranged between 1.03 to 1.48 for intra-day and inter-day for HPTLC. The calibration range was 200-700 ng per band (r 2 = 0.99321). Quercetin quantity in the ethanolic extract of the flower was found to be 0.011 mg/mL of the extract with an average recovery of 99.01-100.00%. Such fingerprinting is valuable in quality control and checking adulterants of natural drugs. Therefore, it can be helpful for the assessment of different marketable pharmaceuticals preparations.
... A strong correlation between inhibitory activity and polyphenol content was found for Aristotelia chilensis (Rubilar et al., 2011). In a study described by Sayed et al. (2008), in which inhibitory activity was determined by another method, the inhibition of vitexin and isovitexin were found to be 65.7% and 30.1%, respectively, at a concentration of 5.0 mg/mL. So, compared to those results, AEMC was found to have a higher inhibition at lower concentrations. ...
The objective of this study was to evaluate biological and phytochemical properties of the aqueous extract from the leaves of Miconia chamissois Naudin (AEMC). Phytochemical properties were assessed by analyzing the chromatographic profile and the polyphenol content of AEMC. Biological properties evaluation was conducted based on cytotoxicity assay and by evaluating the antioxidant, antimicrobial, and enzymatic inhibition activities. Results indicated the presence of phytochemicals in AEMC such as flavonoids and polyphenols, including rutin, isoquercitrin and vitexin derivatives. AEMC showed antioxidant activity, which may be attributed to the high polyphenolic content. Moreover, AEMC demonstrated in vitro enzyme inhibition activity against tyrosinase and alpha-amylase, as well as showed low cytotoxicity. On the other hand, AEMC exhibited weak antimicrobial activity against S. aureus and C. albicans. Thus, AEMC is a promising alternative in search of potential drugs for the treatment of diseases induced by oxidative stress and inflammation, conditions due to hyperpigmentation processes, such as melisma, as well as for diabetes.
... [2][3][4][5][6] Phytochemical studies of the species have resulted in the isolation of monoterpenoids, sesquiterpenoids, flavonoids, triterpenoids, and sterols. [7][8][9][10][11] The plant also possesses a vast array of biological activities, including antipyretic, analgesic, anti-inflammatory, antibacterial, antioxidant, neuroprotective, anticancer, antidiarrheal, and antidysmenorrhea. [12][13][14][15][16][17] Sesquiterpenoids are the main constituents of this herb with diverse skeletons such as eudesmane, guaiane, patchoulane, cadinane, copane, and rotundane types. ...
Two new sesquiterpenoids, isocyperotundone (1) and 1,4-epoxy-4-hydroxy-4,5-seco-guain-11-en-5-one (2), together with 6 known sesquiterpenoids, cyperotundone (3), cyperenoic acid (4), sugetriol triacetate (5), cyperusol A 3 (6), cyperusol A 2 (7), and cyperusol A 1 (8), were isolated from the methanol extract of the rhizomes of Cyperus rotundus L. High-resolution electrospray ionization mass spectrometry and 1-dimensional (1D) and 2D nuclear magnetic resonance spectroscopy were used to establish the structures of all the compounds. All the compounds were tested for activity on nuclear factor kappa-light-chain-enhancer of activated B cells (NF- κB) signaling. Compounds 1-7 exhibited inhibitory activity on tumor necrosis factor- α-induced activation of the NF- κB pathway, with half-maximal inhibitory concentration values ranging from 34.5 to 73.7 μmol/L.
... [13][14][15] Furthermore, they are used as a remedy for renal colic and dysentery. [16] Moreover, the plant possesses several biological properties such as antioxidant, cytotoxic, [17][18][19] antiallergic [20,21] insecticides, [22,23] antimalarial, antimicrobial, [24,25] antidiarrheal, [26] antipyretic, inflammatory, antiemetic, hypotensive [27] hepatoprotective, [28,29] antidiabetic, [30] and anticonvulsant. [31] Here, we aim to explore new activities of C. rotundus which were not investigated earlier. ...
Background: Cyperus rotundus commonly known as “nutgrass” is extensively used in traditional Chinese and Indian Ayurvedic medicine. It is traditionally used to treat fevers, digestive disorders, wound, and bruises.
Materials and Methods: This study evaluated the sedative‑hypnotic and antidepressant effect of the methanolic extract of C. rotundus (MECR). To perform this study, the whole plants of C. rotundus were taken for extraction with methanol following soaking process and tested for acute toxicity on mice first. The sedative and hypnotic activity were then studied performing hole board and open field tests in albino mice model at the doses of 100 and 200 mg/kg body weight of MECR. Diazepam at the dose of 1 mg/kg was utilized as a standard drug in both experiments. Similarly, antidepressant activity test was also performed using forced swimming test and tail suspension test. Nortriptyline was used as a standard to assess antidepressant activity.
Results: We found that MECR produced an insignificant dose‑dependent effects against locomotors activity of mice both in hole cross and open field tests. Besides, it was also noticed after analyzing forced swimming and tail suspension test that it has no significant antidepressant activity.
Conclusion: Taken together, our study suggests that MECR do not possess notable sedative‑hypnotic and antidepressant or neurobehavioral properties.
... C. rotundus extracts are reported to have several biological activities like, anti-inflammatory (Tandon et al., 2010), in vivo hepatoprotective (Gilani and Janbaz, 1995), antimalarial (Thebtaranonth et al., 1995;Rukunga et al., 2008), antidiarrhoeal (Uddin et al., 2006), antioxidant (Yazdanparast and Ardestani, 2007) antimicrobial (Chen et al., 2011), antiplatelet (Seo et al., 2011), neuroprotective (Kumar et al., 2013), anti-hyperglycemic and anti-nociceptive (Alam et al., 2011;Chaulya et al., 2011). Previous phytochemical screening of C. rotundus showed that it contains many phytoconstituents including flavonoids (Sunil et al., 2011), alkaloids (Sayed et al., 2008) and polyphenols (Zhou and Yin, 2012;Dhillon et al., 1993). Moreover, eight sesquiterpenes, nootkatone, valencene epi-guaidiol, sugebiol, guaidiolA, sugetriol triacetate, cyperenoic acid and cyperotundone were isolated from its rhizomes (Thebtaranonth et al., 1995;Dhillon et al., 1993;Jin et al., 2011;Xu et al., 2009;Tsoyi et al., 2011). ...
In the present study we investigated the hepatotoprotective, hepatitis B virus (HBV) inhibitory and hepatic CYP450 enzyme (CYP3A4) modulatory potential of Cyperus rotundus rhizome fractions. The crude ethanol-extract, including different organic and aqueous fractions were tested for in vitro cytoprotection on HepG2 cells (MTT assay), followed by in vivo evaluation in Wistar rats (serum biochemistry and lipid profile). The in vitro anti-HBV activity was tested on HepG2.2.15 cells (HBsAg and HBeAg Elisa). Of these, the n-butanol and aqueous fractions showed the most promising, dose-dependent hepatoprotection in DCFH-injured HepG2 cells. Further, in CCl4-injured rats, oral administration of C. rotundus (100 and 200 mg/kg·bw/day) significantly normalized serum markers of healthy liver function (SGOT, SGPT, GGT, ALP and bilirubin) and lipid profile (cholesterol, HDL, LDL, VLDL, TG and MDA), including tissue NP-SH and TP levels. Compared to other fractions, the ethyl acetate, n-butanol and aqueous fractions exhibited the best inhibitory effects on viral HBsAg and HBeAg secretions in dose- and time-dependent manner. In addition, reporter gene assay (Dual-luciferase) of transfected HepG2 cells showed mild activation of nuclear PXR-mediated CYP3A4 gene by the three active fractions. Taken together, C. rotundus showed very promising hepatoprotective and anti-HBV potential in experimental settings. In addition, this is the first report on modulation of CYP3A4 by C. rotundus that suggests its safe consumption in relation to drug metabolism and efficacy. Our data could therefore, provide the basis for the ethnobotanical medicinal use of C. rotundus in metabolic liver disorder and hepatitis B patients.
... glycine, isoleucine, leucine, methionine, ornithine, tryptophan dan tyrosine. Dibandingkan dengan polen A. conyzoides, polen C. rotundus mempunyai senyawa lebih kompleks terdiri atas konjugasi fruktosa-asam amino, N-(1-deoxy-alpha-D-fructos-1-yl)-L-tryptophan dan tautomernya, n-butyl-beta-D-fructopyranoside,ethylalpha-D-glucopyranoside, adenosine, asam (-)-(E)caffeoylmalic, vitexin, isovitexin, orientin, epiorientin, myricetin 3-O-beta-D-galactopyranoside, luteolin 7-Obeta-D-glucuronopyranoside-6''-methyl ester, chlorogenic acid, luteolin 4'-O-beta-Dglucuronopyranoside, luteolin 7-O-beta-Dglucuronopyranoside, uridine, asam ellagic, berbagai senyawa antioksidan dan senyawa fenol yang memperlihatkan aktivitas alpha-amylase inhibitory (Sayed et al., 2005) (Meissner et al., 1979). ...
The predatory mite of Phytoseiidae family have extensive cruising range that is not only found in cassava, but also a variety of weeds in cassava plants, such as Ageratum conyzoides and Cyperus cyperus. Extensive cruising range is also well explain the survival rate of the Phytoseiidae family at the time of the density of T. urticae decreased. The research objective is to determine the development period, fecundity and survival rate of Phytoseiidae predatory mite populations at different relative densities T. urticae and pollen. The research method used is an experimental laboratory. The procedure include the provision of A. conyzoides and C. rotundus pollen, the multiplication of predatory mite families Phytoseiidae, the determination of the development period, fecundity and survival rate of predatory mite families Phytoseiidae. The results showed that the length of time the development of predatory mites Amblyseius sp. and Phytoseius sp. faster one day of feeding on egg T. urticae feeding compared to the two types of pollen. Predatory mites survival rate Phytoseius sp. higher than the predatory mites Amblyseius sp. eggs fed T. urticae and both types of pollen. Similarly, the fecundity Phytoseius sp. higher than the mites Amblyseius sp. either fed eggs T. urticae as well as to two types of pollen.
... Amylase Assay Kit (E33651) as previously outlined (Mohamed, 2008;Sayed et al., 2008;Ibrahim et al., 2015). ...
A new isoflavonoid glycoside, iridin A (9), along with eight known isoflavonoids: irilone 4′-methyl ether (1), irilone (2), irisolidone (3), irigenin S (4), irigenin (5), irilone 4′-O-β-d-glucopyranoside (6), iridin S (7), and iridin (8) were separated from Iris×germanica L., Iridaceae, rhizomes. The structural elucidation of these flavonoids was achieved with the aid of extensive spectroscopic techniques and comparing with the published data. They were estimated for their α-amylase and 1,1-diphenyl-2-picrylhydrazyl inhibitory capacities. Compounds 3, 5, and 9 showed α-amylase inhibitory activities with % inhibition 70.8, 67.5, and 70.5, respectively compared to acarbose (a reference α-amylase inhibitor). Moreover, 9 exhibited moderate antioxidant activity with IC50 8.91μM.
... Previous studies on this species have resulted in the isolation of sesquiterpenes, flavonoids, triterpenoids, and steroids. [18][19][20] Our continuing efforts are directed towards identification of bio active compounds from the Indian medicinal flora. Recently, we reported morphological and chemoprofiling comparisons of various solvent extracts of these two species C. scariosus and C. rotundus using analytical techniques. ...
Background:
Cyperus scariosus R. Br and Cyperus rotundus L are widely used in ayurvedic preparation for the treatment of diabetes and other diseases. The early literature, so far, does not indicate the presence of any bioactive principle isolated from these plants.
Objective:
To identify free radical scavenging, anti-diabetic and anti- inflammatory principles from these two species.
Materials and methods:
The bioassay guided fractionation and isolation of active constituents was done by chromatographic techniques. They also evaluated their anti-oxidant activity by DPPH and ABTS. The anti-diabetic activity was screened by α- glucosidase and α- amylase assays. Also, the further evaluation of in vitro anti-inflammatory activity using THP-1 monocytic cells and in vivo anti- inflammatory activity, was confirmed by carrageenan induced rat paw edema as model.
Results:
The activity guided isolation led to isolation of twelve compounds Which are: Stigmasterol([1]), β- sitosterol([2]), Lupeol([3]), Gallic acid([4]), Quercetin([5]), β- amyrin([6]), Oleanolic acid([7]), β- amyrin acetate([8]), 4- hydroxyl butyl cinnamate([9]), 4- hydroxyl cinnamic acid([10]), Caffeic acid,([11]) and Kaempferol([12]) respectively. Among the isolates, the compounds 4 and 5 displayed potent radical scavenging activity with an IC50 values of 0.43 and 0.067 ΅g/ml. The compounds 4, 5 and 10 showed significant anti-diabetic activities. while lupeol([3]) showed potent IL-1 β activity inhibition in THP-1 monocytic cells and also displayed significant (p<0.0025) in vivo anti-inflammatory activity.
Conclusion:
Inbrief, we isolated twelve compounds from both the species. Collectively, our results suggested that aromatic compounds showed good anti-oxidant and anti-diabetic activities.
Summary:
The study investigates the free radical scavenging, α-glucosidase inhibitory and anti-inflammatory effects of constituents isolated from Indian sedges viz. C. scariosus and C. rotundus. The results indicated that phenolic compounds displayed potent fee radical scavenging activty and alpha-glucosidase inhibition activity. While terpene constituent, Lupeol[3] showed good IL-1(β) activity inhibition in THP-1 monocytic cells and also displayed significant (p<0.0025) in vivo anti inflammatory activity in carrageenan induced rat paw edema. However, further studies are required to know the exact molecular mechanism. Abbreviations used: DPPH: 2,2- Diphenyl-1-1-picryl hydrazyl, ABTS: 2,2-Azinobis-3-ethylbenzo thiazoline-6-sulfonic acid, THP-1: Human leukaemia monocytic cell line, IL-1β: Interleukin-1β, IC50-Inhibitory concentration 50%.
... Compound 1 thus corresponds to a novel and striking fructosyl-deferoxamine glycoconjugate. To our knowledge, a similar N-linkage was reported only once before, for the fructose-amino acid conjugate from Cyperus rotundus [12]. ...
Activation of silent biosynthetic gene clusters in Streptomyces bacteria via overexpression of cluster-specific regulatory genes is a promising strategy for the discovery of novel bioactive secondary metabolites. This approach was used in an attempt to activate a cryptic gene cluster in a marine sponge-derived Streptomyces albus PVA94-07 presumably governing the biosynthesis of peptide-based secondary metabolites. While no new peptide-based metabolites were detected in the recombinant strain, it was shown to produce at least four new analogues of deferoxamine with additional acyl and sugar moieties, for which chemical structures were fully elucidated. Biological activity tests of two of the new deferoxamine analogues revealed weak activity against Escherichia coli. The gene knockout experiment in the gene cluster targeted for activation, as well as overexpression of certain genes from this cluster did not have an effect on the production of these compounds by the strain overexpressing the regulator. It seems plausible that the production of such compounds is a response to stress imposed by the production of an as-yet unidentified metabolite specified by the cryptic cluster.
... It is also said to increase and purify breast milk (Sharma et al., 200;Chopra and Ananda, 2003). In the traditional Chinese medicine, the rhizomes of C. rotundus are termed as Xiang-Fu and are used to treat stomach and hormone problems in women (Sayed et al., 2007;2008;Liu et al., 2010). Although it is used in the traditional medicine the active constituents, the side effects, especially the toxicity if any is not well documented. ...
The herb Cyperus rotundus L (Cyperaceae) is used by the traditional medicine practitioners of ayurvedic medicine in India for CNS disorders like loss of memory, depression and epilepsy. Though some of these properties have been evaluated, stream lined scientific evaluation is lacking to support the possible association between CNS disorders and C. rotundus. The present study was carried out to identify and characterize the phytochemical constituents and metal contents of the medicinal plant C. rotundus and to determine its toxicity. Qualitative chemical analysis confirmed the presence of phenols, tannins, glycoside and flavonoids. Physiochemical analysis revealed that the herb C. rotundus has low ash value and moderate water and alcohol solubility. Metal analysis revealed the presence of metal contents copper, lead, nickel and cadmium. Characterization of constituents using TLC technique exhibited 6 fractions and HPTLC analysis exhibited 13 peaks. Acute toxicological studies showed no mortality or morbidity up to 2000mg/kg body weight in Wistar rats. Sub chronic toxicity study revealed that, food, water consumption and body weight of animals didn't vary significantly. But the hematological parameters showed an increase in WBC count and Hemoglobin level. The kidney function and liver function didn't change even after long term exposure. Industrial relevance: The herb Cyprus rotundus L (Cyperaceae) is used by the traditional medicine practitioners of ayurvedic medicine in India for CNS disorders like loss of memory, depression and epilepsy. The present study scientifically evaluated the physiochemical and toxicological effects of C. rotundus. The results obtained will help in identification and isolation of bioactive constituents for new therapeutic targets.
... [13] The alpha amylase inhibitory activity is shown by some of the phenolic compound isolated from C. rotundus (L.). [14] In addition to this C. rotundus is also reported for having the antidiabetic activity. [15] An experimental study showed that the extracts of C. rotundus had displayed 100% inhibition of alpha glucosidase at the concentration of 100 µg/ ml. ...
Asthma and diabetes have strong relationship; both are cause and effect of each other. Oxidative stress due to bronchial asthma may cause insulin resistance whereas lack of proper insulin can cause defective smooth muscle relaxant. There is no single medicine available that can manage both diseases, rather the mainstay treatment of bronchial asthma causes hyperglycemia. Keeping this problem in focus, in this study the hypoglycemic effect of an indigenous antiasthmatic Ayurvedic drug Shirishadi was evaluated. Pancreatic alpha amylase and glucosidase inhibitors offer an effective strategy to lower the level of post prandial hyperglycemia via control of starch breakdown. For evaluation of hypoglycemic activity of drug, in-vitro alpha amylase and alpha glucosidase enzyme inhibition was calculated. Ethanolic extract of compound showed 76.40% + 0.88% reduction in alpha amylase activity and 63.85% + 0.36% in alpha glucosidase activity with IC50 0.68 mg/ml and 2.89 mg/ml, respectively. This study suggests that the ethanolic extract of Shirishadi polyherbal compound effectively acts as alpha amylase and glucosidase inhibitor leading to a reduction in starch hydrolysis and hence acts as antiasthmatic as well as hypoglycemic drug.
... In addition, some flavonoids have been known to have antimicrobial and antihypoglycemic activities (Souza et al., 2003). To the best of our knowledge, there has been no previous report on the isolation of compounds 1, 2 and 3 from Remirea, and there is only one previous report on the isolation of compound 3 from Cyperaceae (Sayed et al., 2008). Also, this kind of flavonoid possesses several biological activities (Dayff and Lattanzio, 2008 ), including antioxidant and anti-inflammatory (Ló pez-Lá zaro, 2009) and plays an important role in chemotaxonomy of Cyperaceae species (Harborne et al., 1985). ...
Ethnopharmacological relevance:
Remirea maritima Aubl., popularly known as "capim-da-praia", is popularly employed in the treatment of diarrhea, kidney disease, fever, and for analgesic and anti-inflammatory purposes through the preparation of teas. Few studies have focused on the chemical composition and its biological properties.
Aim of the study:
This work evaluated the antinocipetive, anti-inflammatory and antioxidant activities of the aqueous extract from Remirea maritima Aubl. as well as the isolation and identification of the chemical compounds.
Materials and methods:
Compounds were isolated from aqueous extract of Remirea maritima through preparative HPLC and the structures were identified by means of NMR and MS analysis. The tests for antinociceptive, anti-inflammatory, and antioxidant activities, along with motor coordination test (Rota rod), were performed over the aqueous extract.
Results:
The phytochemical investigation of aqueous extract of Remirea maritima resulted in the isolation of three flavone glycosides. The structures of these compounds were determined by means of MS and 1D and 2D NMR data as vitexin-2″-O-β-D-glucopyranoside, isovitexin-2″-O-β-D-glucopyranoside, and luteolin-7-O-glucuronide. Acute pretreatment with aqueous extract (100, 200 or 400mg/kg, i.p.) caused a significant decrease (p<0.001) in the number of abdominal writhes. In the formalin test, higher doses significantly inhibited the late (inflammatory pain) phase of formalin-induced licking (p<0.05 or 0.001). In the hot plate test, there was no significant difference in nociceptive behavior, discarding the possible central effect of the aqueous extract. In the rota rod test, it was verified that the aqueous extract in all concentration evaluated does not alter the motor coordination of mice, such antinociceptive results were unlikely to be caused by motor abnormality. In the peritonitis test, induced by carrageenan, the treatment with aqueous extract produced a significant reduction in leukocyte migration in all concentration evaluated. Additionally, a significant reduction of lipoperoxidation (TBARS test) and in nitric oxide formation (.NO Scavenging assay) was observed in antioxidant activity assay.
Conclusion:
The biological and phytochemical investigations of the aqueous extract of Remirea maritima resulted in the identification of three flavone glycosides that have been described here for the first time in Remirea and effective analgesic activity in various pain models, probably mediated via the inhibition of peripheral mediators which could be related to its strong antioxidant effect observed in vitro.
... The tuber of Cyperus rotundus is a kind of Traditional Chinese Medicine named "Xiangfuzi", which is widely used in folk medicine as an antidiarrheal, antidepressant, anti-Candida, antipyretic, analgesic, anti-inflammatory, and anti-emetic remedy for dysentery and women's diseases [1,2]. Previous phytochemical studies on this plant have revealed the presence of alkaloids, flavonoids, glycosides and furochromones, and many new sesquiterpenoids [2][3][4][5][6]. Recently, we reported a new flavonoid and five known compounds from the rhizomes of Cyperus rotundus [7]. ...
Two novel compounds, 1α-methoxy-3β-hydroxy-4α-(3′,4′-dihydroxyphenyl)-1, 2,3,4-tetrahydronaphthalin (1) and 1α,3β-dihydroxy-4α-(3′,4′-dihydroxyphenyl)-1,2,3,4-tetrahydronaphthalin (2), were isolated along with six known compounds 3–8 from the rhizomes of Cyperus rotundus. This paper reports the isolation and full spectroscopic characterization of these new compounds by NMR, UV, IR and MS data.
... Phytochemical study on the aerial parts of Cyperus species led to isolation of flavonoids and coumarins (Sayed et al., 2008) as the most important constituents (Yu et al., 2007). Liver ailments remain a serious health problem (Baranisrinivasan et al., 2009). ...
The present work explored the potential hepatoprotective activity of total ethanol and successive extracts of Cyperus alternifolius L (Cyperaceae) against carbon tetrachloride (CCl(4))-induced hepatotoxicity in rats and to isolate their bioactive constituents.
For isolation and identification of the compounds, column chromatography and spectroscopic analysis were used, a model of hepatotoxicity by CCl(4) in rats was used to evaluate the total ethanol extract and its successive fractions.
Phytochemical screening of C. alternifolius revealed the presence of different phytochemical groups. The plant proved to be safe for human use because it did not induce any signs of toxicity or mortality in mice when administered orally at doses up to 5000 mg kg(-1). The total alcoholic extract in doses of 100 and 200 mg kg(-1) and the successive extracts (ether, chloroform and ethyl acetate) in a dose of 10 mg kg(-1) exhibited a significant (p ≤ 0.05) protective effect by lowering the elevated serum levels of aspartate aminotransferase: 230.4, 218.8, 224.6, 227.4 and 231.6 U L(-1), respectively, compared with 111.6 U L(-1) for silymarin (25 mg kg(-1)). Serum levels of alanine aminotransferase were also reduced: 77.4, 72.7, 79.7, 76.0 and 79.7 U L(-1) compared to 63.7 U L(-1) for silymarin. Alkaline phosphatase: 164.6, 158.0, 163.6, 154.7 and 166.4 U L(-1) compared to 138.2 U L(-1) for silymarin. Total bilirubin: 0.50, 0.46, 0.55, 0.52 and 0.57 mg dl(-1) compared to 0.42 mg dl(-1) for silymarin. Cholesterol: 213.1, 200.0, 192.7, 193.6 and 197.1 mg dl(-1) compared to 180.3 mg dl(-1) for silymarin. Triglycerides: 237.3, 222.4, 209.5, 206.8 and 210.2 mg dl(-1) compared to 196.8 mg dl(-1) for silymarin. Eight phenolic compounds were isolated from C. alternifolius for the first time and identified as esculetin 1, umbelliferon 2, imperatorin 3, psoralen 4, xanthotoxin 5, quercetin 6, quercetin-3-O-rutinoside 7 and gallic acid 8.
The results concluded that C. alternifolius possesses significant protective effect against hepatotoxicity induced by CCl(4).
Since centuries, Cyperus rotundus L. has been used against gastric ailments in traditional Indian medicine, especially in Ayurveda and Siddha. Therefore, it is very obvious that this plant will have a greater potential to treat gastric ulcers. For this reason, in this study, we mainly focused on the ulcer-preventive role of C. rotundus in rats treated with non-steroidal anti-inflammatory drugs.
Seventy percent methanolic extract of the plant was prepared and fed to 36-h fasted rats. Ulcer was induced in these rats by single oral administration of aspirin (400 mg/kg) 1 h after the administration of the plant extract. After 4 h, the rats were sacrificed, ulcer index was calculated, and antioxidant activity of the extract in gastric mucosa was evaluated by determining the levels of superoxide dismutase, glutathione, glutathione peroxidase, and tissue lipid peroxidation.
Oral administration of different doses of C. rotundus rhizome methanolic extract (CME; 250 mg/kg and 500 mg/kg) significantly inhibited aspirin-induced gastric ulceration in animals in a dose-dependent manner (49.32% and 53.15%, respectively), which was also comparable with the standard gastric ulcer drug ranitidine. Administration of CME also significantly increased the activity of superoxide dismutase, cellular glutathione and glutathione peroxidase, and inhibited the lipid peroxidation in the gastric mucosa of ulcerated animals in a dose-dependent manner.
Our results showed that C. rotundus extract has the capacity to significantly inhibit aspirin-induced gastric ulcers through an antioxidant defense mechanism. This study warrants further examination of this plant for its gastroprotective activities.
Methanol extracts from the leaves of 55 species, belonging to 4 subgenera and 16 subsection of genus Euphorbia (Euphorbiaceae) have been screened for presence of ellagic acid (EA). EA was quantified by gas chromatography-mass spectrometry (GC-MS) in fresh plant material Euphorbia sp. growing in Russia and Kyrgyzstan in the wild and in indoor and outdoor collections of the Peter the Great Botanical Garden of the Komarov Botanical Institute of the Russian Academy of Sciences (Saint-Petersburg). EA was detected in the extracts of 17 species of tree subgenera. In subgenus Althymalus Neck. Ex Rchb. EA was detected in E. hamata (Haw.) Sweet (section Anthacanthae Lem.), in subgenus Chamaesyce Raf. – E. maculata L. (section Anisophyllum Roep.); in subgenus Esula Pers. This compound was found in representatives of sections Esula (Pers.) Dumort. (E. virgata Waldst. Et Kit.), Helioscopia Dumort. (E. alpina Ledeb., E. aristata Schmalh., E. condylocarpa M. Bieb., E. lucorum Rupr. ex Maxim., E. palustris L., E. procera M. Bieb., E. semivillosa (Prokh.) Kryl., E. squamosa Willd., E. stricta L.), Holophyllum (Prokh.) Prokh. (E. griffithii Hook. f., E. komaroviana Prokh., E. rupestris Ledeb.), Paralias Dumort. (E. taurinensis All.) and Pithyusa (Raf.) Lázaro (E. glareosa Pall. Ex M. Bieb.). In 38 EA was not detected, including all studies species of subgenus Euphorbia. For 10 species (E. alpina, E. glareosa, E. griffithii, E. hamata, E. lucorum, E. procera, E. rupestris, E. semivillosa, E. stricta and E. taurinensis) EA was detected for the first time. Highest EA amount was found in leaves of E. hamata (4100 ppm) and E. squamosa (4300 ppm).
The aim of the present study is to investigate the phytochemical composition of tiger nut (TN) (Cyperus esculentus L.) and its neuroprotective potential in scopolamine (Scop)-induced cognitive impairment in rats. The UHPLC-ESI-QTOF-MS analysis enabled the putative annotation of 88 metabolites, such as saccharides, amino acids, organic acids, fatty acids, phenolic compounds and flavonoids. Treatment with TN extract restored Scop-induced learning and memory impairments. In parallel, TN extract succeeded in lowering amyloid beta, β-secretase protein expression and acetylcholine esterase (AChE) activity in the hippocampus of rats. TN extract decreased malondialdehyde levels, restored antioxidant levels and reduced proinflammatory cytokines as well as the Bax/Bcl2 ratio. Histopathological analysis demonstrated marked neuroprotection in TN-treated groups. In conclusion, the present study reveals that TN extract attenuates Scop-induced memory impairments by diminishing amyloid beta aggregates, as well as its anti-inflammatory, antioxidant, anti-apoptotic and anti-AChE activities.
In this work, twenty-five water-soluble constituents were isolated from the bulbs of Lilium davidii var. unicolor, including two new compounds termed liliumtides A and B (1–2), and seventeen known compounds (3–4, 6–13, 15, 17, 21–25) isolated from the genus of Lilium for the first time. Their structures were established using high-resolution electrospray ionization mass spectroscopy and 1D and 2D nuclear magnetic resonance data. To confirm furtherly the absolute configuration of liliumtide A, and to accumulate enough sample to study the anti-insomnia effect, a total synthesis for liliumtide A was achieved by four steps. The pentobarbital-induced sleeping time test showed that compared with the blank control group, the liliumtide A decreased sleep latency and significantly increased the sleep time. These results suggested that liliumtide A could be investigated as a natural anti-insomnia lead compound in the pharmaceutical and food industries.
Cyperus rotundus (nut grass in English) is a perennial erect sedge plant and is distributed in over 90 countries of the world, where it has been mostly classified as a highly invasive weed. Despite this classification, the plant has been considered from traditional times to be medicinally important. The traditional uses of the plant in various countries include uses against various gastrointestinal tract disorders, skin diseases, leprosy, fever, and neurological disorders. Evaluation of the plant and especially its rhizomes in a scientific manner has revealed the presence of numerous phytochemicals and wide-ranging pharmacological activities, which include anti-microbial, gastrointestinal, wound healing, anti-diabetic, anti-cancer, anti-malarial, anti-obesity, hepatoprotective, and anti-pyretic activity. The scientific validation of a number of traditional uses strongly indicates that the plant may prove useful in the discovery of a number of lead compounds and novel drugs.
Cyperus rotundus L. (Nutgrass, family Cyperaceae) is a notorious weed which is widespread in temperate tropical and subtropical regions of the world. Owing to its richness and potent pharmacological activities, efforts have been devoted to identify its bioactive constituents. Since 1965, a total of about 192 compounds including terpenoids, flavonoids, stilbenes, aromatics and aliphatic fatty acids have been characterized. This review summarizes the bioactivities and mechanism of action of some of the compounds from C. rotundus L.
Cyperus rotundus (nut grass in English) is a perennial erect sedge plant and is distributed in over 90 countries of the world, where it has been mostly classified as a highly invasive weed. Despite this classification, the plant has been considered from traditional times to be medicinally important. The traditional uses of the plant in various countries include uses against various gastrointestinal tract disorders, skin diseases, leprosy, fever, and neurological disorders. Evaluation of the plant and especially its rhizomes in a scientific manner has revealed the presence of numerous phytochemicals and wide-ranging pharmacological activities, which include anti-microbial, gastrointestinal, wound healing, anti-diabetic, anti-cancer, anti-malarial, anti-obesity, hepatoprotective, and anti-pyretic activity. The scientific validation of a number of traditional uses strongly indicates that the plant may prove useful in the discovery of a number of lead compounds and novel drugs.
Galactites is a genus of flowering plants belonging to Asteraceae family. This genus is mainly represented by the Galactites elegans (All.) Nyman ex Soldano, the milky thistle, a plant of Mediterranean origin. Galactites elegans is consumed as a monofloral boar thistle honey. Chromatography separation of CHCl 3 and n- BuOH extracts of aerial parts of G. elegans led to isolation of 18 pure compounds. Their structures were elucidated by 1D-and 2D-NMR spectroscopy and confirmed by mass spectrometry analysis. Sinapic aldehyde, abietin, chlorogenic acid, neochlorogenic acid, 8 α -hydroxypinoresinol, 9 α -hydroxypinoresinol, pinoresinol, 4-ketopinoresinol, nortrachelogenin, and erythro -guaiacylglycerol- β - O -4′-dihydroconiferyl alcohol were isolated from CHCl 3 extract, while luteolin 4′- O -glucuronide, naringenin - 7- O -neohesperidoside, kaempferol-3- O - α -L-rhamnopyranosyl-(1→6)- β -D-glucopyranoside, apigenin-7- O - α -L-rhamnopyranosyl-(1→6)- β -D-glucopyranoside, quercitrin, quercetin-3- O - α -L-rhamnopyranosyl-(1→6)- β -D-glucopyranoside, ciwujiatone, and nortrachelogenin-4,4′-di- O - β -D-glucopyranoside were obtained from n- BuOH extract. The majority of isolated compounds displayed a significant antioxidant potential in vitro test (DPPH). The ability of compounds to reduce the level of peroxides in control and BHP-treated Jurkat cells was studied. The lignan derivatives were also able to reduce at 50 μ M the basal level of peroxides in Jurkat cells as well as counteract peroxide increase induced by BHP treatment. Particularly 8 α -hydroxypinoresinol was the most active showing 70% of peroxide level inhibition.
Purple nutsedge (Cyperus rotundus L.), a troublesome weed, is economically damaging weed, which is widely naturalized in the tropical and subtropical regions of the world. This weed has been reported to cause 20–90% yield losses in various agronomic and horticultural crops across the world. Perennial nature, genetic diversity, ability to tolerate adverse climatic conditions, high rate of reproduction, ease-of-dispersion, strong competitive abilities, and allelopathic potential assist this weed to thrive in a range of agro-climatic regions. Routine cultural approaches, including crop rotation, crop choice, and mechanical cultivation, are ineffective in achieving season-long management of C. rotundus. Pre-emergent and post-emergent herbicides, as well as myco-herbicides, can control its growth but fail to limit the regenerative capacity and tuber viability of C. rotundus in the long term. Integration of herbicides with tillage operations during summer fallows would be a reliable option to desiccate the tubers and rhizomes of C. rotundus. Furthermore, preventive measures as well as complete destruction of nascent foci would be helpful in preventing future spread of this weed. This review will help researchers and scientists in understanding the reproductive biology and future threats of C. rotundus, leading towards the development of improved control methodologies. The information presented in this article will also enable researchers and growers to address the prevailing gaps in the eco-biology of this weed for the long-term control of C. rotundus in economically important field crops.
Background
Cyperus rotundus L. (Cyperaceae), is a perennial sedge distributed throughout India and other parts of the world. Its tubers are used as an appetizer, febrifuge and to treat bleeding, blisters, boils, cough, diarrhea, inflammation, lacteal disorders, rheumatoid arthritis, stomach ailments, skin rashes, thirst, vomiting, worm infestation and wounds.
Objective
Our study was planned to isolate chemical constituents from the rhizomes of C. rotundus and to characterized their structures.
Method
The air-dried rhizome powder was exhaustively extracted with methanol in a Soxhlet apparatus. The concentrated methanol extract was adsorbed on silica gel (60-120 mesh) for the preparation of a slurry. The dried slurry was chromatographed over silica gel column packed in petroleum ether. The column was eluted with petroleum ether, chloroform and methanol, successively, in order of increasing polarity to isolate the compounds.
Results
Phytochemical investigation of the tubers led to isolate a sesquiterpenone characterized as 12-methyl cyprot-3-en-2-one-13-oic acid ( 1 ), two aliphatic ketone viz. n -dotriacontan-15-one ( 2 ) and n -tetracontan-7-one ( 8 ), fatty esters n -pentadecanyl octadec-9, 12- dienoate ( n -pentadecanyl linoleate, 3) , n -hexadecanyl linoleate ( 4 ), n -hexadecanyl oleate ( 5 ) and n -pentacos-13ʹ-enyl octadec-9-enoate ( n -pentacos-13ʹ-enyl oleate, 9 ), two steroidal esters s tigmast-5,22–dien-3 β –olyl n -dodecanoate (stigmasterol laurate, 6 ) and stigmast-5, 22-dien-3 β -olyl n -tetradecanoate (stigmasterol myristate, 7 ), β-sitosterol-3β-O-glucoside (10) and a triterpenic glycosidic ester lup-12, 20 (29)-dien-3β-ol-3-α-L-arabinopyranosyl-2'-oleate (lupenyl 3β-O-arabinpyranosyl 2′-oleate, 11 ). The structures of these compounds were established by spectral data analysis and chemical reactions.
Conclusion
A sesquiterpene identified as cyprot-3-en-2-one-14-oic acid, two aliphatic ketones, fatty esters, two steroidal esters, β-sitosterol-3β-O-glucoside and lupenyl 3β-O-arabinpyranosyl 2′-oleate were isolated for the first time from the rhizomes.
Cyperus rotundus Linn. (family Cyperaceae), commonly known as motha or musta in India and purple nut sedge around the world, noted remarkably for their strong invasive nature, are spreading worldwide. Although being rated as ‘worst weed’, it is a natural reservoir of wide spectrum of bioactive phytochemicals having multifaceted medicinal and therapeutic properties. Its biological potential has been recognized with different scientific standards in various places of the world. C. rotundus has been widely used to ameliorate several maladies in the traditional medical system of India, Pakistan, Bangladesh, Nepal, China, Japan, Arab countries, African nation etc. It contains various volatile and non-volatile components including essential oils, alkaloids, flavonoids, terpenoids, chromones, phenylpropanoids, phenolic acids, iridoides etc. which possess great phyto-pharmaceutical and therapeutic values. The chemical composition and biological efficacy of different solvent extracts and essential oils from C. rotundus has been studied in several geographical locations around the world like Brazil, Tunisia, Germany, Nigeria, South Africa, Iran, China and India and great variations were observed in the phytochemical composition with respect to selected plant parts, extraction systems, phytogeographical locations and seasonal differences suggesting the existence of various chemotypes. Presently, our review consider the confirmation of earlier studies that projecting the medicinal chemistry of C. rotundus coupled with its pharmacological and phytomedicinal properties which may help the researchers towards their future approaches of discovering elite chemotype(s) and explore its industrial and/or commercial uses as ingredients of health promoting and therapeutic natural products.
Descriptions of the drug: Frequently fusiform, some slightly curved, 2–3.5 cm long, 0.5–1 cm in diameter. Externally dark brown or blackish-brown, longitudinally wrinkled and with 6–10 slightly prominent annular nodes with brown fibrous roots and broken roots; or slightly smooth and exhibiting indistinct annular nodes on the ones of fibrous roots completely removed. Texture hard, fracture of steamed rhizomes appearing yellowish-brown or reddish-brown, horny: fracture of the unsteamed ones white and starchy, an endodermis ring obvious, stele darkened in colour, with scattered dotted vascular bundles. Odour, aromatic; taste, slightly bitter.
Nitraria tangutorum Bor., having edible berries, is valued for reputed health benefits in Qinghai-Tibet plateau. The phytochemical research on the fruit juice of N. tangutorum led to the isolation of twenty-six compounds including five new compounds, tangutorids A–D (1, 2, 3a, and 3b), and (3E,5E)-7-O-β-glucosyl-4-(2-methoxy-2-oxoethyl)hepta-3,5-dienoic acid (15). The structures of these compounds were elucidated through comprehensive spectroscopic analyses. Tangutorids A–F were the first examples of glucose-derived β-carbolines from natural products. The biogenetic pathways of 1–8 were proposed to involve Pictet–Spengler reactions and described starting from the co-isolated tryptophan (10) and corresponding aldehydes. All isolates were evaluated for their antioxidant and α-glucosidase inhibitory activities. Compounds 21, 22, and 24 showed antioxidant activity with SC50 values ranging from 12.2 ± 1.9 to 30.4 ± 2.7 μg/mL, and compound 1 showed strong α-glucosidase inhibitory effect with IC50 value of 63.3 ± 4.6 μg/mL.
Iris species are well recognized as wealthy sources of isoflavonoids. In the present study, phytochemical investigation of the rhizomes of Iris germanica (Iridaceae) procure the isolation of two new isoflavonoids namely, 8-hydroxyirilone 5-methyl ether (2) and 8-hydroxyirilone (3), along with eight known isoflavonoids: irilone 4′-methyl ether (1), irilone (4), irisolidone (5), irigenin S (6), irigenin (7), irilone 4′-O-β-D-glucopyranoside (8), iridin S (9), and iridin (10). The isolated flavonoids were structurally characterized with the assist of comprehensive spectroscopic analyses (UV, IR, 1D and 2D NMR, and HRMS) and comparing with the published data. They were estimated for their antioxidant and antidaibetic capacities using DPPH and α-amylase inhibition assays, respectively. Compounds 2, 3, and 4 exhibited prominent antioxidant
activities with IC50 values of 12.92, 9.23, and 10.46 μM, respectively compared to propyl gallate (IC50 7.11 μM).
Moreover, 2–5 possessed highest α-amylase inhibitory activity with % inhibition 66.1, 78.3, 67.3, and 70.1, respectively in comparison to acarbose (reference α-amylase inhibitor). Additionally, their structure-activity relationship has been discussed.
Vitexin and isovitexin are active components of many traditional Chinese medicines, and were found in various medicinal plants. Vitexin (5, 7, 4-trihydroxyflavone-8-glucoside) has recently received increased attention due to its wide range of pharmacological effects, including but not limited to anti-oxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects. Isovitexin (apigenin-6-C-glucoside), an isomer of vitexin, generally purified together with vitexin, also exhibits diverse biological activities. Latest research has suggested that vitexin and isovitexin could be potential substitute medicines for diversity diseases, and may be adjuvants for stubborn diseases or health products. This review summarized recent findings on various pharmacological activities and associative signalling pathways of vitexin and isovitexin to provide a reference for future research and clinical applications.
A new isoflavonoid, 5,7,4'-trihydroxy-2'-methoxy-3'-prenylisoflavone (1), along with eleven phenolic compounds (2-12), licoricone (2), 6-O-p-hydroxybenzoyl-6-epi-aucubin (3), 6-O-p-hydroxybenzoyl-6-epi- monomelittoside (4), 7-O-p-hydroxybenzoyl-8-epi-loganic acid (5), verproside (6), syringopicroside B (7), syringopicroside C (8), oleuropeinic acid (9), oleuroside (10), 10-hydroxyoleuropein (11), senburisideI (12), were obtained from the rhizomes of Cyperus rotundus. Their chemical structures were elucidated on the basis of UV, IR, MS, NMR spectroscopic analyses. Compound 12 showed considerable macrophages respiratory burst (MRB) inhibitory activity in the test with IC50 value of approximately 27 μM.
Species belonging to the family Cyperaceae are an important source of active constituents with biological activity. Cyperaceae is a family of monocotyledonous known as sedges, which superficially resemble grasses or flowering plants rushes. The family comprises about 4000 species described in about 90 genera. These species are widely distributed in tropical Asia and tropical South America. While, sedges may be found growing in all types of soils, many are associated with wet lands or poor soils. The genus Cyperus includes about 600 species, some of which are used in folk medicine, the most important one is Cyperus rotundus L. In this review we focused on the phenolics and nitrogenous constituents isolated from different Cyperus species growing in Egypt.
Two new iridoid glycosides, rotunduside A (1) and rotunduside B (2), along with four known compounds, 6′′-O-p-coumaroylgenipin gentiobioside (3), isoaragoside (4), chionoside A (5), and helioside C (6) were isolated from the rhizomes of Cyperus rotundus L. Their chemical structures were determined by application of spectroscopic (NMR, MS) and chemical methodologies. The macrophages respiratory burst (MRB) inhibitory activity of all the isolated compounds was reported. Compound 2 showed marginal inhibitory activity against MRB in the test with IC50 value of approximately 31 μM.
Supercritical fluid extraction with carbon dioxide (SC-CO2 extraction) was performed to isolate essential oils from the rhizomes of Cyperus rotundus Linn. Effects of temperature, pressure, extraction time, and CO2 flow rate on the yield of essential oils were investigated by response surface methodology (RSM). The oil yield was represented by a second-order polynomial model using central composite rotatable design (CCRD). The oil yield increased significantly with pressure (p0.0001) and CO2 flow rate (p
Fructosamine has long been considered as a key intermediate of the Maillard reaction, which to a large extent is responsible for specific aroma, taste, and color formation in thermally processed or dehydrated foods. Since the 1980s, however, as a product of the Amadori rearrangement reaction between glucose and biologically significant amines such as proteins, fructosamine has experienced a boom in biomedical research, mainly due to its relevance to pathologies in diabetes and aging. In this chapter, we assess the scope of the knowledge on and applications of fructosamine-related molecules in chemistry, food, and health sciences, as reflected mostly in publications within the past decade. Methods of fructosamine synthesis and analysis, its chemical, and biological properties, and degradation reactions, together with fructosamine-modifying and -recognizing proteins are surveyed.
A new iridoid glycoside, rotunduside (1), along with four known iridoid glycosides, 10-O-p-hydroxybenzoyltheviridoside (2), 10-O-vanilloyltheviridoside (3), 6″-O-(trans-p-coumaroyl)-procumbide (4) and loganic acid (5), was isolated from the rhizomes of Cyperus rotundus L. Their chemical structures were elucidated on the basis of UV, IR, MS and NMR spectroscopic analyses. In addition, the macrophages respiratory burst (MRB) inhibitory activity of the isolated compounds was reported. Compound 2 exhibited considerable MRB inhibitory activity in the test with IC(50) value of ∼37 μM.
An extract of the rhizomes of Cyperus rotundus L. afforded two new sesquiterpenoids (2 and 3) with rearranged secoeudesmane and germacrane skeletons, and a new 9,10-seco-cycloartane triterpenoid (9), as well as seven previously reported terpenoids, including a monoterpenoid (1), five sesquiterpenoids (4-8) with guaiane, patchoulane, and eudesmane skeletons, and a 3,4- seco-dammarane nortriterpenoid (10). The structures of 1-10 were elucidated by extensive spectroscopic methods and comparison with the literature data. The structures of 2 and 6 were confirmed by single-crystal X-ray diffraction analysis. The carbon skeleton of 2 is the third example reported thus far of such a skeleton and the 9,10-seco-cycloartane framework of 9 has rarely been found from a natural source. Compound 7 was a new natural product and compounds 1-5 and 7-10 were discovered from the genus Cyperus for the first time. This study may provide some useful information for the chemotaxonomy for the plant Cyperus rotundus.
Fructosamine has long been considered as a key intermediate of the Maillard reaction, which to a large extent is responsible for specific aroma, taste, and color formation in thermally processed or dehydrated foods. Since the 1980s, however, as a product of the Amadori rearrangement reaction between glucose and biologically significant amines such as proteins, fructosamine has experienced a boom in biomedical research, mainly due to its relevance to pathologies in diabetes and aging. In this chapter, we assess the scope of the knowledge on and applications of fructosamine-related molecules in chemistry, food, and health sciences, as reflected mostly in publications within the past decade. Methods of fructosamine synthesis and analysis, its chemical, and biological properties, and degradation reactions, together with fructosamine-modifying and -recognizing proteins are surveyed.
Cyperi rhizoma, the rhizome of Cyperus rotundus L. (Family Cyperaceae), is a well-known functional food and traditional herbal medicine in Korea. It has been reported that Cyperi rhizoma has antioxidant and free radical scavenging activities that play a major role in protection of neurodegenerative disorders, such as Parkinson's disease (PD). In the present study, the neuroprotective effects of a water extract of Cyperi rhizoma (CRE) against 6-hydroxydopamine (6-OHDA)-induced neuronal damage were evaluated in an experimental model of PD. In PC12 cells, CRE showed a significant protective effect on cell viability at 50 and 100 microg/mL. CRE inhibited generation of reactive oxygen species and nitric oxide, reduction of mitochondrial membrane potential, and caspase-3 activity, which were induced by 6-OHDA. CRE also showed a significant protective effect against damage to dopaminergic neurons in primary mesencephalic culture. These results suggest that CRE has neuroprotective effects against 6-OHDA-induced toxicity through antioxidant and anti-apoptotic activities in an in vitro PD model.
Two novel phenolic glycosides cis-p-coumaric acid 4-O-(2′-O-β-d-apiofuranosyl)-β-d-glucopyranoside and trans-p-coumaric acid 4-O-(2′-O-β-d-apiofuranosyl)-β-d-glucopyranoside were isolated and identified from Salvia officinalis together with 4-hydroxyacetophenone 4-O-(6′-O-β-d-apiofuranosyl)-β-d-glucopyranoside, luteolin 7-O-β-d-glucoside, 7- and 3′-O-β-d-glucuronide, 6-hydroxyluteolin 7-O-β-d-glucoside and 7-O-glucuronide, and 6,8-di-C-β-d-glucosylapigenin (vicenin-2). The luteolin glucuronides and vicenin-2 were identified as new sage constituents.
The ftavonoid pigments, one of the most numerous and widespread groups of natural constituents, are ofimportance and interest to a wide variety ofphysical and biological scientists and work on their chemistry, occurrence, natural distribution and biological function continues unabated. In 1975, a mono graph covering their chemistry and biochemistry was published by Chapman and Hall under our editors hip entitled The Flavonoids. The considerable success of this publication indicated that it filled an important place in the scientific literature with its comprehensive coverage of these fascinating and versatile plant substances. The present volume is intended to update that earlier work and provide a detailed review of progress in the ftavonoid field during the years 1975 to 1980. Although cross references are made to The Flavonoids, this supplement is entirely self-contained and where necessary, tabular da ta from the earlier volume are incJuded and expanded here. The choice oftopics in Recent Advances has been dictated by the developments that have occurred in ftavonoid research since 1975, so that not all subjects covered in The Flavonoids are reviewed again here. A major advance in ftavonoid separation has been the app1ication ofhigh performance liquid chromatography (HPLC) and this is reviewed inter alia in the opening chapter on separation techniques. An equally important development in the spectral analysis of ftavonoids has been the measurement of carbon-13 NMR spectra and this subject is authoritatively discussed in Chapter 2 and is also illustrated with the spectra of 125 representative ftavonoids.
Phytochemical investigations on the aerial parts of Phlomis samia resulted in the isolation of a simple phenolic glucoside, 2,6-dimethoxy-4-hydroxyphenol- 1-O-β-D-glucopyranoside (1); a megastigmane glucoside, phlomuroside (=3-hydroxy-5,6-epoxy-β-ionol-9-O-β-D-glucopyranoside) (2); and a nucleotide glycoside, uridine (3). From the aerial parts of P. carica, the same phenolic glucoside, 2,6-dimethoxy-4-hydroxyphenol-1-O-β-D-glucopyranoside (1); as well as an acetophenon glucoside, picein (4); and 2 monoterpenoid glucosides, - betulalbuside A (5) and 1-hydroxylinaloyl-6-O-β-D- glucopyranoside (6) -were isolated and identified. The structure elucidation of the isolates was based on spectroscopic evidence.
Structure of substances XIV and XVIII, obtained previously among the constituents of the calyx of persimmons (Diospyros kaki, Ebenaceae), was examined, and XIV was determined as astragalin (kaempferol 3-β-D-glucopyranoside) and XVIII as n-butyl-β-D-fructopyranoside, although the latter was considered to be an artifact. Carbon-13 NMR spectra of kaempferol, quercetin, trifolin, astragalin, and hyperin were measured and their structure was proved from the assignment of NMR signals. © 1978, The Pharmaceutical Society of Japan. All rights reserved.
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Sixteen compounds were isolated from the aerial parts of Solanum incanum L. These compounds included ten flavonoids ( 1‐10 ), chlorogenic acid ( 11 ), adenosine ( 12 ), benzyl‐ O ‐β‐ D ‐xylopyranosyl(1→2)‐β‐ D ‐glucopyranoside ( 13 ), and three phenylalkanoic acids ( 14‐16 ). The structures were determined from their physical and spectral data. Among these compounds, kaempferol 3‐ O ‐(6″′‐ O ‐2,5‐dihydroxycinnamoyl)‐β‐ D ‐glucopyranosyl (1→2) β‐ D ‐glucopyranoside ( 10 ) was identified as a new compound.
A new chemotype of Cyperus rotundus was found in Hawaii based on the sesquiterpene composition of the mature tubers. The K-type has higher concentrations of patchoulenyl acetate and sugeonyl acetate than the three known Asian chemotypes. Biochemical and evolutionary aspects of these findings are discussed.
A total of 20 Cyperus and four Pycreus species were investigated for their flavonoids. Glycosides of apigenin, luteolin, tricin and quercetin were identified. Luteolin 5-0-methyl ether and the aurones, aureusidin and sulphuretin, were found as aglycones. The distribution of flavonoids in the different taxa and their chemosystematic significance is discussed.
Cyperus capitatus contains a homologous series of 11 6-alkyl-2-hydroxy-3-methyl-1,4-benzoquinones, with chain length C17 to C27. Those with a C17, C19 and C21 side chain were isolated and named as capiquinones A, C and E.
This fourth edition of the highly successful and concise textbook contains about 20 % new data. Now included are chapters on 19F and 31P NMR as well as references to important Raman bands. With their unique approach of presenting - in the form of texts, tables, charts, and graphs - a succinct compilation of essential reference data for the interpretation of NMR, IR, UV/Vis, and mass spectra, the authors also provide a hands-on guide for interpreting experimental spectral data and elucidating the structure of the respective compounds behind them. Besides spectra of common solvents, calibration reagents, and MALDI and FAB MS matrix materials, fragmentation rules for mass spectrometry and UV/Vis spectra of representative compounds are included. The book will benefit students during courses and exercises, and advanced learners may use it to supplement their understanding of extended textbooks on the topic. While only a basic knowledge of spectroscopic techniques is required to use this book, it will serve as a data reference for specialists in the field and will support practitioners routinely faced with the task of interpreting spectral information. From a review of the previous edition: "Practically all teachers in spectroscopy and countless students know these books and work continuously with them." (Magnetic Resonance in Chemistry, 2002, Vol. 40, Issue 3, p. 247) © Springer-Verlag Berlin Heidelberg 2009. All rights are reserved.
A comprehensive and up-to-date listing is provided of the distribution of phenethylamines in the Plant Kingdom. Such a listing is of importance because of their considerable physiological activity in higher animals. Their distribution in plants is also of some taxonomic interest.
The main flavonoid from Oenothera lavandulaefolia, T. and G., has been isolated and shown to be myricetin 3-β-galactoside.
Four sesquiterpenes, β-selinene, isocurcumenol, nootkatone and aristolone and one triterpene, oleanolic acid were isolated from the ethylacetate fraction of the rhizomes of Cyperus rotundus and tested for their ability to modulate γ-aminobutyric acid (GABAA)-benzodiazepine receptor function by radioligand binding assays using rat cerebrocortical membranes. Among these compounds, only isocurcumenol, one of the newly identified constituents of this plant, was found to inhibit [3H]Ro15-1788 binding and enhance [3H]flunitrazepam binding in the presence of GABA. These results suggest that isocurcumenol may serve as a benzodiazepine receptor agonist and allosterically modulate GABAergic neurotransmission via enhancement of endogenous receptor ligand binding.
The methanolic extract of the whole plant of Cyperus longus originating in Egypt was found to show scavenging activity for DPPH radical. By bioassay-guided separation, a nor-stilbene dimer, longusone A, with a tropilene structure and three stilbene dimers, longusols A, B, and C, were isolated as the active constituents together with 10 phenolic compounds. The structures of new compounds were elucidated on the basis of chemical and physicochemical evidence.
High-resolution, 1H- (360 and 400 MHz) and 13C-n.m.r. (90.52 and 100.57 MHz) spectra of the mutarotated N-(1-deoxy-d-fructos-1-yl)-l-amino acids (“fructose-amino acids”) 1–14 in D2O are reported. The 1H spectra allow unambiguous assignment of the signals of the major constituents (β-pyranose forms). Signals of the other forms are not well resolved and therefore not interpreted. The 13C spectra of 1–14 show ∼64% of β-pyranose, ∼15% of α-furanose, ∼15% of β-furanose, and ∼6% of α-pyranose forms. For N-(1-deoxy-d-fructos-1-yl)-l-alanine (2), 2% of the keto form is present. In solution in D2O, H-1 of the fructose moieties undergoes a slow H/D-exchange, which is strongly accelerated at more-basic pH values. Compound 2 is stable over the pH range 0.7–11.9, as revealed by 13C-n.m.r. spectroscopy. The 13C-shift changes caused by protonation/deprotonation are given. There is no significant change in the ratios of the various forms with change in pH.
A new flavone C-glucoside: 2″-O-caffeoylorientin was isolated from the leaves of Vitex polygama and identified by spectroscopic methods, together with orientin, iso-orientin, vitexin, isovitexin, luteolin, quercetin, quercetin 3-O-methylether and p-hydroxybenzoic acid.
New sesquiterpenoids with 4,5-secoeudesmane and cyperolone carbon skeletons were isolated from Cyperus rotundus, and characterized by spectroscopic analysis. The structures were confirmed by synthesis from (+)-dihydrocarvone and (+)-cyperolone.
13C-NMR spectra of hydroxylated flavones and flavonols are presented for the first time. Analyses of the spectra are derived by consideration of a series of acetophenones, cinnamic acids, flavones and flavonols of increasing oxygenation pattern. The accepted substitution additivity rules have been shown to hold for these compounds except in cases where structural modifications involve the C-3,4 and 5 positions.
Die Umsetzung von L-Tryptophan mit D-Fructose liefert kristallisierte 2-Nα-L-Tryptophan-2-desoxy-D-glucose(I), mit D-Glucose 1-Nα-L-Tryptophan-1-desoxy-D-fructose (II), Aus L-Histidin und D-Fructose entsteht 2-Nα-L-Histidin-2-desoxy-D-Glucose (II).
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
The new norsesquiterpene hydrocarbon, cyprotene, the sesquiterpenes 2,4-patchouladiene, epoxycyperene, 2,4,11-eudesmatriene and 3,5,11-eudesmatriene, were identified as constituents in the hydrodistillation products of Cyperus alopecuroides from Cameroon by spectroscopic methods and chemical conversions. © 1997 Elsevier Science Ltd. All rights reserved
Brevifolin carboxylic acid, brevifolin, corilagin, 3,6-(R)-hexahydroxydiphenoyl-(α/β)-1C4-glucopyranose, 1,2,6-tri-O-galloyl-β-4C1-glucopyranose, 1,4,6-tri-O-galloyl-β-4C1-glucopyranose, ellagic acid, 3,4,8,9,10-pentahydroxydibenzo[b,d]pyran-6-one, granatin-B and punicafolin were isolated from the leaves of Punica granatum. 1H and 13C NMR spectra of brevifolin carboxylic acid and brevifolin have been recorded and assigned for the first time. A new interpretation of the NMR data or related compounds is discussed. The structure of the new natural polyphenol-1,2,3- tri-O-galloyl-β-4C1-glucopyranose has been established.
Two new fructofuranosides, n-butyl-α- and β-d-fructofuranoside, were isolated from Cynomorium songaricum. Their structures were established on the basis of spectroscopic methods including 2D NMR techniques.
Spectroscopic methodology in analyzing two-dimensional (2D) NMR spectra of a mixture of several phenolic compounds that occur in natural products is described. Particular emphasis has been given to the determination of scalar coupling connectivities by homonuclear 2D correlated spectroscopy (COSY), remote intraresidue connectivities by totally correlated spectroscopy (TOCSY), and spatially close but uncoupled 1H nuclei by homonuclear 2D nuclear Overhauser effect spectroscopy (NOESY/ROESY). Preliminary data to identify phenolic acids in the methanolic extracts from two oregano plants are also reported. Keywords: Oregano; phenolic acids; 1H NMR; COSY; TOCSY; NOESY/ROESY
Volatile aroma components of raw earth almond and those developed in a roasting process were analyzed by gas chromatography/mass spectrometry to determine the identity of compounds that would indicate the degree of roasting. In all, 143 components (ca. 90% of the total isolate) were positively identified, of which 138 are reported as earth almond volatiles for the first time. The main flavor compounds identified in raw earth almond were alcohols, whereas in roasted earth almond, the majority of the volatiles identified suggest the flavor formation is via the Maillard reaction, with pyrazines contributing directly to the roasted flavor of earth almond. Keywords: Chufa; Cyperus esculentus; earth-almond; roasting process; volatiles
A series of O-isopropylidene protected aromatic Amadori compounds [N-(1-deoxy-d-fructos-1-yl)-l-amino acid esters] were synthesized by reacting 2,3:4,5-di-O-isopropylidene-1-O-(trifluoromethanesulfonyl)-d-fructopyranose with alkyl esters of l-phenylalanine, l-tyrosine, and l-tryptophan. The Amadori compounds were obtained in much higher yields than those previously reported due to utilizing triflate as an extremely reactive leaving group at C-1 of the sugar reagent. The triflate derivative was prepared in high yield using the sterically hindered, non-nucleophilic base, 2,6-di-tert-butyl-4-methylpyridine, as proton acceptor. The Amadori compounds were characterized by 1H- or 13C-n.m.r. spectroscopy, as well as by i.r. and mass spectroscopy. 13C-n.m.r. spectroscopy was used to study the equilibria among the various ring forms of the free-hydroxy d-fructose-tryptophan compound.
The leaves of Parkinsonia aculeata have been found to contain three C-glycosides. Two, could be separated by fractional crystallization after preliminary lead salt purification, but preparative paper chromatography was found effective for the separation of all three. The first (epi-orientin) is a C-glucoside of luteolin and resembles oreintin in composition, chemical reactions and UV and IR spectra but differs in m.p. and rotation and may be an epimer of orientin. The second (Parkinsonin-A) is a C-glucoside of 5-O-methylluteolin and is closely related to orientin. The third (Parkinsonin-B) is a C-glucoside of 5,7-di-O-methylluteolin and has stereochemistry related to epi-orientin.
Leaf extracts from different Sri Lankan provenances of Clausena indica were compared by HPLC linked with diode array detection. Remarkable chemical differences towards different types of amides were observed between the collections from the northern dry semi-evergreen forests and the central montane rainforests. Apart from the already known phenethyl cinnamide, four new tryptamine derived amides were detected with different acid moieties: the cinnamic acid amides named balasubramide and prebalamide and the isovaleric acid amides named madugin and methylmadugin. Balasubramide is characterised by an eightmembered lactam ring. All structures were established by spectral analyses.
Three antifeedants were isolated from the basal stem of Cyperus nipponicus and C. distans. One was identified by spectral analysis as the coumaran, remirol, and the others as the furoquinones, cyperaquinone and scabequinone. The significance of the above compounds in the chemical defense of weeds is discussed.
Naturally occurring cadinenes appearing in the literature up to the end of 1986 have been reviewed.
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The potential of one- and two-dimensional NMR techniques for the identification of individual sugar residues, their anomeric configuration, interglycosidic linkages, sequencing and the site of any appended group, in establishing the structures of naturally occurring oligosaccharides and glycosides is presented.
Pure compounds were isolated from plant extracts with antimalarial activity. The extracts were obtained from the tubers of Cyperus rotundus L. (Cyperaceae), the rootbark of Zanthoxylum gilletii (De Wild) Waterm. (Rutaceae), and the rootbark of Margaritaria discoidea (Baill.) Webster (Euphorbiaceae). The most active compounds included (IC50 within brackets): alpha-cyperone (1) (5.5 micrograms/ml), N-isobutyldeca-2,4-dienamide (2) (5.4 micrograms/ml), and securinine (3) (5.4 micrograms/ml). A mixture of autoxidation products of beta-selinene was found to be the most active antimalarial substances obtained from C. rotundus (5.6 micrograms/ml.