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Leaf flavonoids of Cyperus species in Egypt
Abstract
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.
... Likewise, members of Cyperaceae exhibited the same pattern, especially in the occurrence of the rare marker compound, luteolin 5-methyl ether. Additionally, tricin, and luteolin were found in the glycosidic form in conjugation with uronic acids exemplified in 7-glucosides and/or 7-glucuronides [22,25]. Luteolin was mainly found as luteolin-O-glucuronide (50) Noteworthy, for tricin glycosides, the glucuronyl moiety was tentatively assigned to the O-7 hydroxyl group because the hydroxyl group at C-5 in ring A is not considered a place for sugar substitution [29]. ...
... Aurones are structural isomers of flavones and are considered minor flavonoids owing to their very limited abundance in nature [22]. Abundant aurones were reported in Cyperus species [22]. ...
... Aurones are structural isomers of flavones and are considered minor flavonoids owing to their very limited abundance in nature [22]. Abundant aurones were reported in Cyperus species [22]. In the current study, several aurones were identified in peaks 34, 41, 42, 43, 52, 66, 68, and 71. ...
Chemical Profile of Cyperus laevigatus and Its Protective Effects against Thioacetamide-Induced Hepatorenal Toxicity in Rats
... Likewise, members of Cyperaceae exhibited the same pattern, especially in the occurrence of the rare marker compound, luteolin 5-methyl ether. Additionally, tricin, and luteolin were found in the glycosidic form in conjugation with uronic acids exemplied in 7-glucosides and/or 7-glucuronides [22,25]. Luteolin was mainly found as luteolin-O-glucuronide (50) Noteworthy, for tricin glycosides, the glucuronyl moiety was tentatively assigned to the O-7 hydroxyl group because the hydroxyl group at C-5 in ring A is not considered a place for sugar substitution [29]. ...
... Aurones are structural isomers of avones and are considered minor avonoids owing to their very limited abundance in nature [22]. Abundant aurones were reported in Cyperus species [22]. ...
... Aurones are structural isomers of avones and are considered minor avonoids owing to their very limited abundance in nature [22]. Abundant aurones were reported in Cyperus species [22]. In the current study, several aurones were identied in peaks 34, 41, 42, 43, 52, 66, 68, and 71. ...
Cyperus species represent a group of cosmopolitan plants used in folk medicine to treat
several diseases. In the current study, the phytochemical prole of Cyperus laevigatus ethanolic extract
(CLEE) was assessed using UPLC-QTOF–MS/MS. The protective effect of CLEE at 50 and 100 mg /kg
body weight (b.w.) was evaluated on hepatorenal injuries induced by thioacetamide (100 mg/kg) via
investigation of the extract’s effects on oxidative stress, inammatory markers and histopathological
changes in the liver and kidney. UPLC-QTOF–MS/MS analysis of CLEE resulted in the identication
of 94 compounds, including organic and phenolic acids, avones, aurones, and fatty acids. CLEE
improved the antioxidant status in the liver and kidney, as manifested by enhancement of reduced
glutathione (GSH) and coenzyme Q10 (CoQ10), in addition to the reduction in malondialdehyde
(MDA), nitric oxide (NO), and 8-hydroxy-2′-deoxyguanosine (8OHdG). Moreover, CLEE positively
affected oxidative stress parameters in plasma and thwarted the depletion of hepatorenal ATP content
by thioacetamide (TAA). Furthermore, treatment of rats with CLEE alleviated the signicant increase
in plasma liver enzymes, kidney function parameters, and inammatory markers. The protective
effect of CLEE was conrmed by a histopathological study of the liver and kidney. Our results
proposed that CLEE may reduce TAA-hepatorenal toxicity via its antioxidant and anti-inammatory
properties suppressing oxidative stress.
... Phytochemical studies on C. rotundus have revealed the presence of a variety of avonoids, phenolic acids, cyperol, sitosterol, nootkatone and valencene. [32][33][34][35] To check the catalytic efficiency of the synthesized nanoparticles, we utilize a facile, and environmentally benign protocol for the formation of 2,3-dihydroquinazolin-4(1H)-ones, spirooxindoles, and chromenylpyrimidin-2,4-diones. 2,3-Dihydroquinazolinone derivatives are important fused heterocycles that exhibit a wide range of pharmacological, biological and medicinal properties. ...
... The phytochemical constituents of the plant extracts include catechin (avonoid), gallic acid (phenolic acid), cyperol, sitosterol, nootkatone and valencene (Fig. S5, ESI †), [32][33][34][35] which are likely responsible for the formation of the nanoparticles. The role of polyols present in the extract for the formation of core-shell nanoparticles is depicted in Scheme 2. For example, the phenolic hydroxyl groups of catechin can chelate with metal ions to form chelate rings, which forms the metal nanoparticles by electron transfer. ...
This paper describes the biosynthesis of core–shell CuO–Pd nanoparticles with the aid of a Cyperus
rotundus rhizome extract. The crystallinity, surface chemistry, morphology and thermal properties of the
synthesized nanoparticles were characterized by X-ray diffraction, X-ray photoelectron spectroscopy,
transmission electron microscopy, and thermogravimetric analysis. The nanoparticles with Pd covered by
a CuO enriched shell showed enhanced catalytic performance for organic transformations to synthesize
2,3-dihydroquinazolin-4(1H)-ones, spirooxindoles, and chromenylpyrimidin-2,4-diones in excellent yield.
Moreover, the nanocatalyst can be recycled effectively for five consecutive reactions without significant
loss of catalytic activity.
... Furthermore, the plant possesses antimalarial (Thebtaranonth, Thebtaranonth, Wanauppathamkul, & Yuthavong, 1995; Weenen et al., 1990), antidiarrhoeal (Uddin, Mondal, Shilpi, & Rahman, 2006), anti-diabetic (Bawden, Quant, & Raman, 2002a, b), hepatoprotective (Mehta, Shankar, Geetha, & Saluja, 1999) and insecticidal properties (Morimoto, Fuji, & Komai, 1999). The genus Cyperus is characterised by the presence of sesquiterpenes (Bordoloi, Shukla, Nath, & Sharma, 1989; Fengming, Toshio, Hisashi, Kiyafumi, & Masayuki, 2004; Rizk, 1986), quinones (Alves, Moreira, Paul, & Costa, 1992 Rizk, 1986), flavonoids (Abdel-Mogib, Basaif, & Ezmirly, 2000; Abdel-Razik, Nassar, El-Khrisy, Dawidar, & Mabry, 2005; El-Habashy, Mansour, Zahran, El-Hadidi, & Saleh, 1989; Nassar, Abu-Mustafa, Abdel-Razik, & Dawidar, 1998; Rizk, 1986), stilbenoids (Morikawa, Xu, Matsuda, & Yashikawa, 2002), coumarins (Antonio, Eliseo, Paola, Antonia, & Ildefonsa, 1993) and phenylpropanoids (Abdel-Mogib et al., 2000). The previous phytochemical studies of C. rotundus L. have resulted in the isolation of sesquiterpenes (Bawden et al., 2002a; Bordoloi et al., 1989; Chhabra, Sharma, Dhillon, & Vij, 2002; El-Gohary, 2004; Ha et al., 2002; Kalsi, Sharma, Singh, Singh, & Chhabra, 1995; Komai & Tang, 1989; Ohira et al., 1998; Rizk, 1986; Sonwa & Ko¨nigKo¨nig, 2001; Sonwa, Ko¨nigKo¨nig, Kubeczka, & Motl, 1997), flavonoids (Rizk, 1986; El-Habashy et al., 1989), phenylpropanoids (Koichiro & Kunikazu, 1981), phenolic acids (Koichiro & Kunikazu, 1981), alkaloids (Jeong, Miyamoto, Inagaki, Kim, & Higuchi, 2000) and nitrogenous substances (Cantalejo, 1997; Smith, 1977). ...
... The genus Cyperus is characterised by the presence of sesquiterpenes (Bordoloi, Shukla, Nath, & Sharma, 1989; Fengming, Toshio, Hisashi, Kiyafumi, & Masayuki, 2004; Rizk, 1986), quinones (Alves, Moreira, Paul, & Costa, 1992 Rizk, 1986), flavonoids (Abdel-Mogib, Basaif, & Ezmirly, 2000; Abdel-Razik, Nassar, El-Khrisy, Dawidar, & Mabry, 2005; El-Habashy, Mansour, Zahran, El-Hadidi, & Saleh, 1989; Nassar, Abu-Mustafa, Abdel-Razik, & Dawidar, 1998; Rizk, 1986), stilbenoids (Morikawa, Xu, Matsuda, & Yashikawa, 2002), coumarins (Antonio, Eliseo, Paola, Antonia, & Ildefonsa, 1993) and phenylpropanoids (Abdel-Mogib et al., 2000). The previous phytochemical studies of C. rotundus L. have resulted in the isolation of sesquiterpenes (Bawden et al., 2002a; Bordoloi et al., 1989; Chhabra, Sharma, Dhillon, & Vij, 2002; El-Gohary, 2004; Ha et al., 2002; Kalsi, Sharma, Singh, Singh, & Chhabra, 1995; Komai & Tang, 1989; Ohira et al., 1998; Rizk, 1986; Sonwa & Ko¨nigKo¨nig, 2001; Sonwa, Ko¨nigKo¨nig, Kubeczka, & Motl, 1997), flavonoids (Rizk, 1986; El-Habashy et al., 1989), phenylpropanoids (Koichiro & Kunikazu, 1981), phenolic acids (Koichiro & Kunikazu, 1981), alkaloids (Jeong, Miyamoto, Inagaki, Kim, & Higuchi, 2000) and nitrogenous substances (Cantalejo, 1997; Smith, 1977). Also, saponins (Singh & Singh, 1980), cardiac glycosides and tannins (Rizk, 1986) have been reported. ...
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.
... The differential degree of inhibitory (5, 10, 15, 20 and 25%) effect on the growth of rice cultivars may be due to the presence of various allelochemicals at different levelin both the weed extracts. Previous phytochemical studies on C. rotundus revealed the presence of alkaloids, flavonoids, tannins, starch, glycosides and furochromones, and many novel sesquiterpenoids (Raut et al., 2006;EL-Habashy et al., 1989;Kapadia et al., 1967;Jeong et al., 2000;Sayed et al., 2007;Xuet al., 2008). The herb C.dactylon contains beta sitosterol, beta-carotene, vitamin C, palmitic acid, andtriterpenoids. ...
Weeds are enemies to the crop plants and have harmful effects on agricultural crops due to several factors such as competition for space, light and nutrients and allelopathy. In the present study,various concentrations (0,5,10,15,20 and 25%) of whole plant aqueous extractsof weeds, Cyperus rotundusL.( Purple nut sedge) and Cynodan dactylon(L.) Pers. (Bermuda grass) were tested for assessing their allelopathic potential on seed germination and seedling growth of some rice (Oryza sativa L.) cultivars i.e.ADT-36,BPT5204 and IR-20 using pot culture experiments. The experimental results revealed that all the concentrations of both the weed extracts had inhibition on germination percentage, seedling length, number of,dry weight and chlorophyll contents of 15 day old seedlings of all the three rice cultivars and the inhibitory effect of the extracts was concentration dependent. However, at 5% of C. rotundus and10% of C. dactylon extracts did notaffect seed germination of IR-20 . Among the rice cultivars,the higher degree of growth inhibition was observed in ADT-36followed by BPT-5204 and IR-20 . The weed C.rotundusexhibited more intense on growth suppression of rice cultivars thanC.dactylon.
... The identity of mariscetin has still not been confirmed to date. Interestingly, the 4-deoxyaurone sulfuretin (1, Fig. 2) was also recorded in several Cyperus species (El-Habashy et al., 1989;Kumar et al., 2014), and in Carex appressa (Harborne et al., 1985). This is the only aurone found in the Carex genus. ...
... This paper proposes the green synthesis of hematite nanoparticles using the rhizome of Cyperus rotundus L. a traditional medicinal plant used widely to treat stomach ailments, wounds, boils, and blisters[34][35][36][37]. Phytochemical studies of C. rotundus revealed the presence of flavonoids, tannins, alkaloids, starch, furochromones, and glycosides[38,39]. The above green approach is comparatively facile, fast and eco-friendly because it reduces the environmental hazards by utilizing non-toxic chemicals and renewable materials owing to their larger surface area-volume ratio. ...
A novel magnetically recoverable hematite nanoparticles (α-Fe2O3 NPs) was fabricated by a simple, one pot, and green method using the rhizome of Cyperus rotundus L., as a reducing and stabilizing agent. The prepared nanoparticles were well characterized by all parameters. TEM showed that the hematite nanoparticles had a rhombohedral shape and ranged in size from 80 to 100 nm. The phase study of the α-Fe2O3 nanoparticles was confirmed by Raman spectroscopy. In addition, the synthesized nanoparticles shows good photocatalytic activity in degradation of highly toxic Congo red dye within 25 min, and the same NPs exhibits higher catalytic activity for the reduction of 4-nitro-o-phenylenediamine (4-NPD) to 1,2,4-benzenetriamine in the presence of NaBH4 within 12 min. After the reaction, the catalyst was recovered and reused three times without significant loss of catalytic activity.
... Tricin, in the free form, was first isolated from rusted wheat leaves dating back to 1930 31 and later was also observed in many monocotyledonous plants such as the family of Gramineae 32,33 and Cyperaceae. 34,35 The isolated tricin from plants usually contains tricin derivatives including tricin-glycosides, tricin-lignans, and tricin-lignan-glycosides. In tricin-glycoside, tricin is attached to carbohydrate units, while tricin-lignan refers to tricin derivatives in which tricin is acylated with monolignols ( Fig. 1). ...
Our understanding of the structure and biosynthetic pathway of lignin, a phenylpropanoid heteropolymer, continues to evolve, especially with the discovery of new lignin monomers/structural moieties such as monolignol acetate, hydroxycinnamyl aldehyde/alcohol, and p-hydroxybenzoate in the past decades. Recently, tricin has been reported as a component incorporated into monocot lignin. As a flavonoid compound widely distributed in herbaceous plants, tricin has been extensively studied due to its biological significance in plant growth as well as its potential for pharmaceutical importance. Tricin is biosynthesized as a constituent of plant secondary metabolites through a combination of phenylpropanoid and polyketide pathways. Tricin occurs in plants in either free or conjugated forms such as tricin-glycosides, tricin-lignans, and tricin-lignan-glycosides.The emergence of tricin covalently incorporated with lignin biopolymer implies the possible association of lignification and tricin biosynthesis. This review summarizes the occurrence of tricin and its derivatives in plants. In addition, synthesis, potential application, and characterization of tricin are discussed.
... 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).
... Aureusidin, like myricetin, quercetin or kaempferol, could also be a hydrolysis product. Aureusidin or its glycosides, although known natural products, are rare in nature (El-Habashy, Mansour, Zahram, El-Hadidi & Saleh, 1989) and this is the first report of its presence in blackcurrant. ...
Chemical investigation of blackcurrant seed residue from oil extraction revealed the presence of an array of polyphenols which were dominated by four anthocyanins consisting of the rutinosides and glucosides of delphinidin and cyanidin. Also isolated were the glucosides and rutinosides of myricetin and quercetin, kaempferol-3-glucoside, dihydroquercetin and aureusidin, as well as the phenolic acids 1-cinnamoyl- and 1-p-coumaroyl-β-d-glucosides. This is the first report of aureusidin and 1-cinnamoyl-β-d-glucoside as blackcurrant constituents.
... Saleh et al. (1988) investigaram o perfil flavonoídico de 25 das quase 30 espécies de Avena (Poaceae), revelando sinais de correlação entre a químicas e os diferentes grupos de níveis de ploidia entre elas. El-Habashy et al. (1989) estudaram a química de flavonóides de 20 espécies de Cyperus e 4 espécies de Pycreus (Cyperaceae). Os padrões encontrados demonstraram que ocorrem variações expressivas ao nível de gênero, e isto pode ser extensível ao nível subgenérico. ...
The use of micromolecules as markers for the taxonomy of monocotyledons was firstly approached by Dahlgren (1980). Although he had used his classification system for mapping phytochemical markers occurance among the angiosperms, his first approach had pointed to the existence of steroid saponines and chelidonic acid in the superorder Commeliniflorae, which was a strongly distinct phytochemical characteristic from the superorder Liliiflorae. Other classes of micromolecules were used is his system, concerning their distribution among the all the angiosperms, and one of them were the flavonoids. Even though the flavonoids were not used in the classification system at that time, they became important markers of a wide application in the taxonomic approach of Monocotyledons, among of the most important markers were: flavonols, flavones, 6- and 8-hydroxiflavonoids and flavonoid sulphates. The use of this group of phenolic compounds have allowed the character polarization that makes easy thephylogenetic systematics in identification of mono and polyphyletic groups.
... Compared to the naturally abundance of flavones, aurones have a limited occurrence and have been less investigated. The best known aurone and the frequently cited is aureusidin, which has been isolated from several species of Cyperus [28] where it occurs as the 6-glucoside (aureusin) or 4-glucoside (cernuoside) [29]. Like all subclasses of flavonoids, aurones are mostly found as hydroxylated, methoxylated, glycosylated and to less extent as biaurones [30,31]. ...
Aurones [2-benzylidenebenzofuran-3(2H)-ones] are the secondary metabolites natural compounds belong to the flavonoids family, and structurally are the isomers of flavones, widely present in fruits and flowers where they play significant role in the pigmentation of the part of plant in which they occur. Literature survey clearly indicates that flavones, chalcones, flavonols and isoflavones have been studied largely for their therapeutical potential. Somehow, aurones still are less studied and it is only recently that these compounds have begun to be investigated.
In this review, we report the recent advances made on the therapeutical potential of aurones in different biological areas. Their synthesis, structure-activity relationships, the importance of the substitution pattern will also be discussed. Finally, some aspects regarding the possible development of aurones will be highlighted briefly.
... A number of pharmacological and biological activities including anti-Candida, anti-inflammatory, antidiabetic, antidiarrhoeal, cytoprotective, antimutagenic, antimicrobial, antibacterial, antioxidant, cytotoxic and apoptotic, anti-pyretic and analgesic activities have been reported for this plant7891011121314151617. Previous phytochemical studies on C. rotundus revealed the presence of alkaloids, flavonoids, tannins, starch, glycosides and furochromones, and many novel sesquiterpenoids [9,181920212223242526272829. The chemical composition of the volatile oils of C. rotundus has been extensively studied and four chemotypes (H-, K-, M-O-types), of the essential oils from different parts of Asia have been reported [14,303132333435. ...
The essential oils from the rhizomes of Cyperus rotundus L. collected from two different locations (Empangeni-A and KwaDlangezwa-B; both in the Kwa-Zulu Natal Province of South Africa) were obtained by hydrodistillation and analyzed by capillary GC and GC/MS. Forty-one and 43 components were identified, representing 89.9% and 92.0% of sample A and sample B, respectively. Alpha-cyperone (11.0%), myrtenol (7.9%), caryophyllene oxide (5.4%) and beta-pinene (5.3%) were major compounds in the oil of sample A. The main constituents of the oil of sample B were beta-pinene (11.3%), alpha-pinene (10.8%), alpha-cyperone (7.9%), myrtenol (7.1%) and alpha-selinene (6.6%).
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.
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.
It is the purpose of this chapter to discuss the five remaining flavonoid structural types, here collectively known as the minor flavonoids, chalcones, aurones, dihydrochalcones, flavanones and dihydroflavonols. In order to orientate the reader it should be mentioned that chalcones, aurones and dihydrochalcones were discussed in Chapter 9 of The Flavonoids (1975) while flavanones and dihydroflavonols were treated in Chapter 11. In The Flavonoids-Advances in Research (1982) the five structural types were brought together in Chapter 6 under the present name. As far as is practicable I have presented the material here in the same order and format as used in the earlier two volumes. This makes it possible for the reader to compare current material easily and directly with material in the corresponding sections in the other two books. For the most part each structural type is presented in terms of increasing structural complexity: the primary classification is based upon B-ring oxygenation with the presentation of compounds in order of degree of A-ring oxygenation, O-alkylation and C-alkylation.
The essential oil obtained by hydrodistillation of rhizomes of Cyperus rotundus L.(Nutgrass) was analyzed by GC-MS analysis of oil. Ninety eight components of Cyperus rotundus representing 78.4% of the oil were identified. The main constituents in the essential oil were cyperene (9.76%), humulen (7.97%), β- selinene (7.88%), zierone (4.62%), campholenic aldehyde (3.83%), a.-pinene (3.51%), longiverbenone (2.72%), β.-vatirenene (2.32%), copaene (1.79%), limonene (1.45%).
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.
Recent work on the chemosystematics of the families of the monocotyledons is reviewed. Some emphasis is given to the distribution of plant pigments and
Flavonoids of 27 species of Diplusodon were identified. O-Mono- and diglycosides of apigenin, luteolin, kaempferol, quercetin and myricetin were found. Different glycosidic patterns were observed and they seem to be consistent as taxonomic characters at the species level. Aglycone structures may also be taxonomically relevant, since two main groups of species are sharply discerned by a mutual exclusiveness of flavone and flavonol glycosides. Flavonoid chemistry does not reflect the systems of classifications of the genus and supports the assumption that the foliar pinnately veined pattern is plesiomorphic in Diplusodon.
Flavonoids are a large group of polyphenolic compounds, which are ubiquitously expressed in plants. They are grouped according to their chemical structure and function into flavonols, flavones, flavan-3-ols, anthocyanins, flavanones and isoflavones. Many of flavonoids are found in fruits, vegetables and beverages. Flavonoids have been demonstrated to have advantageous effects on human health because their anti-allergic, anti-inflammatory, anti-platelet aggregation, anti-tumor and anti-oxidant behavior. This report reviews the current knowledge on the molecular mechanisms of action of flavonoids as anti-inflammatory agents and also discusses the relevant patents.
Further phytochemical investigation of the aerial parts of Cyperus rotundus L. afforded a new steroid glycoside named sitosteryl (6'-hentriacontanoyl)-beta-D-galactopyranoside (4) in addition to three furochromones, khellin (2), visnagin (3) and ammiol (9). Furthermore, benzo-alpha-pyrone (coumarin) (1), salicylic acid (5), caffeic acid (6), protocatechuic acid (7), p-coumaric acid (8), tricin (10) and isorhamnetin (11) were isolated. The structures of these compounds were established by spectroscopic methods. The isolated furochromones were tested for insect antifeedant activity against larvae Spodoptera littoralis when incorporated in artificial diet and offered to larvae in a chronic feeding bioassay. Also, visnagin, khellin and sitosteryl (6'-hentriacontanoyl)-beta-D-galactopyranoside showed strong cytotoxic activity against L5178y mouse lymphoma cells and were also active in the brine shrimp lethality test.
A survey of 170 Australian species of Cyperaceae belonging to 35 genera has confirmed that this family
has a highly characteristic flavonoid pattern in leaf and inflorescence. Aurone pigments, the most
distinctive family constituents, were found in the leaves of 25% of the sample and in the inflorescences of
40%. Sulphuretin was found for the first time in the family, in Carex appressa. Flavones, such as tricin and
luteolin, are very common; in addition, a variety of methyl ethers were detected. Luteolin 5-methyl ether
was found in further genera, while luteolin 7-methyl ether, diosmetin and acacetin were detected for the
first time in the Cyperaceae. Flavonols and their methyl ethers occurred in over one-third of the species,
particularly in the leaves, being especially well represented in the genera Fuirena, Gahnia, Lepidosperma
and Mesomelaena. Myricetin was found only twice, in two Baumea species. The 3-desoxyanthocyanidin
carexidin was found in the inflorescences of eight species, i.e. in 5% of the sample. Taxonomically, the
results are mainly of interest at the generic and specific level, where the patterns sometimes show useful
correlations with morphology. At the tribal level, the Sclerieae are the most distinctive, with higher than
average frequency of flavone C-glycosides, flavonols, proanthocyanidins and aurones, and lower than
average frequency of flavones.
A survey of pigmented leaf, inflorescence or seed of eighteen species representing fifteen genera of the Cyperaceae failed to reveal the presence of any of the common anthocyanins, earlier reported as being widespread in the supposedly related grasses (Poaceae). Instead, a new pigment, carexidin (probably a 3-desoxyanthocyanidin), was found in three species and the yellow aurone aureusidin, not previously known in the monocotyledons, was found in eight species. In addition, the chalcone okanin has been detected in the seed of Kyllinga. The taxonomic and phyletic significance of these results are discussed in relation to the existing classification of the grasses and sedges.
A leaf survey of 59 tropical (43 African, and 16 South American) Cyperaceae showed that in addition to the expected flavonoid constituents, i.e. glycoflavones and tricin derivatives, a representative number of them (33%) contained luteolin 5-methyl ether. An equal sample of temperate Cyperaceae failed to show any species with this substance. Thus it appears that this rare 5-methylated flavone is restricted to tropical members of the family. In four species of the South American genus, Lagenocarpus, 6-hydroxyluteolin 7-glucoside was identified. This is the first report of this 6-hydroxyflavone in the Cyperaceae and in the monocotyledons. A new glycoside of iso-orientin, the 3'-glucuronide, was identified in Rhynchospora eximia. The new data have been collected in a revised summary of the leaf flavonoid pattern of the Cyperaceae and compared with those of the Gramineae and Juncaceae. The discovery of luteolin 5-methyl ether in the Cyperaceae brings it closer in chemical terms to the Juncaceae, from which family this compound was first isolated
Flavonoids were surveyed in leaves of 62 species from 11 genera of the Cyperaceae. Over half the sample contained glycoflavones, one half tricin, a third luteolin, while a sixth contained quercetin and/or kaempferol. Tricin was found as the 5-glucoside in Carex riparia and C. acutiformis, the same two species also yielding iso-orientin. Free tricin and a luteolin 7-arabinosylglucoside were obtained from leaves of Cyperus longus. Quercetin 3-rutinoside was detected in leaves of five Carex species. The presence of the characteristic leaf flavonoids (glycoflavones, tricin) of the grasses in this family shows that the Cyperaceae and the Gramineae are more closely linked chemically than a previous study of their inflorescence pigments suggested.