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A new phenylethanoid glucoside from Jacaranda mimosifolia
Abstract
This study reports the isolation of a new phenylethanoid glucoside (1) from the leaves of Jacaranda mimosifolia along with jacaranone (2), followed by the comparative estimation of total antioxidant compounds, total polyphenols and total flavonoids from different solvent extracts of the leaves and flowers. The total antioxidant activity was evaluated by both DPPH and ABTS free-radical scavenging assay methods from different solvent extracts of J. mimosifolia leaves and flowers. The antioxidant activities of the purified compounds (1 and 2) were detected by DPPH-TLC method.
... Jacaranda mimosifolia flowers have a higher amount of total phenols, expressed as mg Gallic acid equivalent (GAE)/g DW (Table 1), compared to seed oil (0.02793 mg GAE/g) reported in Van-Nieuwenhove et al. (2019) and compared to the aqueous extracts of flowers reported by Rana et al. (2013) (49.80 mg GAE/g), both of the same species. Similarly, the results reported in the present research for total phenols are higher than those reported by Li et al. (2014) for 51 types of edible and wildflowers, with ranges from 0.13 to 11.48 mg GAE/g DW for the water-soluble and fat-soluble fractions, additionally, the total phenolic contents varied from 0.50 to 24.36 mg GAE/g DW. ...
... The presence of flavonoids has been described in several investigations with extracts of flowers of the same species. Rana et al. (2013) reported 8.90 mg/g in the aqueous fraction of extracts with organic solvents, whereas Medini et al. (2014) reported 5.55 AE 2.95 and 2.15 AE 0.16 mg Ruthin/g DW for methanol and aqueous extracts of L. delicatulum flowers, respectively. Furthermore, it is observed that the amount of flavonoids is greatly influenced by the type of solvent medium used for the extraction. ...
... The methanol extract of J. mimosifolia flower showed a higher inhibition percentage on the ABTS radicals compared to the DPPH method with no significant difference between both extracts. These results are consistent with those reported by Rana et al. (2013) for aqueous extracts of flowers of the same species. The Jacaranda flower extracts presented a greater antioxidant effect, compared to other extracts of plants used within gastronomy and traditional medicine such as chia (Salvia hispanica) (2.4%-66.3% ...
Antimicrobial resistance to antibiotics is a serious health problem worldwide, for this reason, the search for natural agents with antimicrobial power against pathogenic microorganisms is of current importance. The objective of this work was to evaluate the antioxidant capacity (ABTSþ and DPPH), antimicrobial activity, and polyphenol compounds of methanolic and aqueous extracts of Jacaranda mimosifolia flowers. The antimicrobial activity against Bacillus cereus ATCC 10876, Bacillus subtilis ATCC 6633, Enterococcus faecalis ATCC 51299, Escherichia coli ATCC 25922, Listeria monocytogenes ATCC 19115, Pseudomonas aeruginosa ATCC 27853, Salmonella typhimurium ATCC 14028, Staphylococcus aureus ATCC 25923, and Streptococcus mutans ATCC 25175, was determined using the Kirby Bauer technique. The results of polyphenolic compounds showed a high amount of total flavonoids in the methanolic and aqueous extracts (503.3 AE 86.5 and 245. 7 AE 27.8 mg Rutin Equivalents/g DW, respectively). Quercetin, gallic acid, caffeic acid, and rutin were identified by the HPLC-DAD technique, while in the GC-MS analysis, esters, fatty acids, organic compounds, as well as monosaccharides were identified. Higher antioxidant capacity was detected by the ABTS technique (94.9% and 62.6%) compared to DPPH values (52.5% and 52.7 %) for methanolic and aqueous extracts, respectively. The methanolic extract showed a greater inhibitory effect on gram-positive bacteria, with a predominant higher inhibition percentage on Listeria mono-cytogenes and Streptococcus mutans (86% for both). In conclusion, Jacaranda flower extracts could be a natural antimicrobial and antioxidant alternative due to the considerable amount of polyphenolic compounds, and serve as a sustainable alternative for the isolation of active ingredients that could help in agriculture, aquaculture, livestock, pharmaceutics, and other industrial sectors, to remediate problems such as oxidative stress and anti-microbial abuse.
... Jacaranda copaia [35,36] Antimicrobial (n)Antileishmanial (n)Antitrypanosomal Bark Leaves Jacaranda cuspidifolia [18,19] Moderate antifungal Stem bark Jacaranda filicifolia [37] (n)antimicrobial activity (-)Plasmodium falciparum Jacaranda glabra [28,38] (-)DPPH (-)ABTS Antioxidant Antimicrobial Hypothermic Cardiovascular depressive Hypotensive (-)α-adrenergic receptors Leaves Jacaranda mimosaefolia [25,31,39] Anticancer Potent anticancer Moderate anticancer Twigs Isoliquiritigenin (from twigs) Liquiritigenin (from twigs) Jacaranda obtusifolia [29] Antibacterial Bacteriostatic and bactericidal against S. aureus Antileishmanial Leaves Jacaranda puberula [27,30] (-), decrease, inhibit, reduce, down-regulate. (+), increase, activate, up-regulate. ...
... The antioxidant contents were represented in the form of Trolox equivalent antioxidant capacity (TEAC) per gram of extract which ranged between 38 and 134 mg Trolox equivalent/g extract by ABTS (2, 2'-azinobis-3-ethylbenzothiazoline-6-sulfonic acid) assay, and between 35 and 146 mg Trolox equivalent/g extract by DPPH assay. Isolated compounds [1,6-Bis(1-hydroxy-4-oxo-2,5-cyclohexadiene-1-acetyl)-3-(para-hydroxybenzeneacetyl)β-glucopyranoside and jacaranone] show DPPH-TLC radical scavenging activity [25] . ...
... Similarly, the total flavonoids expressed as quercetin equivalent (QE; 4.4-55.4 mg QE/g) were also higher in the butanolic extracts (55.42 mg/g in the leaves and 32.99 mg/g in the flowers) [25] . Table 3 summarizes the different flavanones, chalcones and isoflavones isolated from Jacaranda species. ...
Genus Jacaranda has been traditionally used in treating skin disorders, venereal diseases, leishmaniasis, colds and rheumatism. Additionally, some species have shown diuretic and astringent properties. Objective: This review highlights and updates the traditional uses, pharmacology and phytochemistry of the genus Jacaranda. Materials and Methods: Information was obtained from Google Scholar, Scirus, PubMed and ScienceDirect. Results: Phytochemical studies on Jacaranda species have shown the presence Flavonoids, Phenylpropanoids, Phenylethanoids, Sterols and Triterpenes. Extracts of different Jacaranda species possess a wide range of pharmacological activities, such as antioxidant antidepressant, antimicrobial, anticancer, anti-leishmanial, anti-protozoal, hypotensive and anti-hypertriglyceridemic activities. Conclusion: The genus Jacaranda is a natural source of antioxidants and has been widely used in traditional Ethnobotany. Thus, it could be exploited as a potential source for plant-based pharmaceutical products. The present review could form a sound basis for further investigation in the potential discovery of new natural bioactive compounds and could provide preliminary information for future research.
... Jacaranda copaia [35,36] Antimicrobial (n)Antileishmanial (n)Antitrypanosomal Bark Leaves Jacaranda cuspidifolia [18,19] Moderate antifungal Stem bark Jacaranda filicifolia [37] (n)antimicrobial activity (-)Plasmodium falciparum Jacaranda glabra [28,38] (-)DPPH (-)ABTS Antioxidant Antimicrobial Hypothermic Cardiovascular depressive Hypotensive (-)α-adrenergic receptors Leaves Jacaranda mimosaefolia [25,31,39] Anticancer Potent anticancer Moderate anticancer Twigs Isoliquiritigenin (from twigs) Liquiritigenin (from twigs) Jacaranda obtusifolia [29] Antibacterial Bacteriostatic and bactericidal against S. aureus Antileishmanial Leaves Jacaranda puberula [27,30] (-), decrease, inhibit, reduce, down-regulate. (+), increase, activate, up-regulate. ...
... The antioxidant contents were represented in the form of Trolox equivalent antioxidant capacity (TEAC) per gram of extract which ranged between 38 and 134 mg Trolox equivalent/g extract by ABTS (2, 2'-azinobis-3-ethylbenzothiazoline-6-sulfonic acid) assay, and between 35 and 146 mg Trolox equivalent/g extract by DPPH assay. Isolated compounds [1,6-Bis(1-hydroxy-4-oxo-2,5-cyclohexadiene-1-acetyl)-3-(para-hydroxybenzeneacetyl)β-glucopyranoside and jacaranone] show DPPH-TLC radical scavenging activity [25] . ...
... Similarly, the total flavonoids expressed as quercetin equivalent (QE; 4.4-55.4 mg QE/g) were also higher in the butanolic extracts (55.42 mg/g in the leaves and 32.99 mg/g in the flowers) [25] . Table 3 summarizes the different flavanones, chalcones and isoflavones isolated from Jacaranda species. ...
ABSTRACT: Genus Jacaranda has been traditionally used in treating skin disorders, venereal diseases, leishmaniasis,
colds and rheumatism. Additionally, some species have shown diuretic and astringent properties. Objective: This
review highlights and updates the traditional uses, pharmacology and phytochemistry of the genus Jacaranda.
Materials and Methods: Information was obtained from Google Scholar, Scirus, PubMed and ScienceDirect.
Results: Phytochemical studies on Jacaranda species have shown the presence Flavonoids, Phenylpropanoids,
Phenylethanoids, Sterols and Triterpenes. Extracts of different Jacaranda species possess a wide range of
pharmacological activities, such as antioxidant antidepressant, antimicrobial, anticancer, anti-leishmanial, antiprotozoal,
hypotensive and anti-hypertriglyceridemic activities. Conclusion: The genus Jacaranda is a natural source
of antioxidants and has been widely used in traditional Ethnobotany. Thus, it could be exploited as a potential source
for plant-based pharmaceutical products. The present review could form a sound basis for further investigation in
the potential discovery of new natural bioactive compounds and could provide preliminary information for future
research.
KEYWORDS: Bignoniaceae; Genus Jacaranda; Pharmacology; Phytochemistry; Traditional uses.
... Jacaranda mimosifolia D. Don, popularly known as jacarandá-mimoso D. Don (Gentry, 1992), is native to northern Argentina, but with wide occurrence in Brazil (Terra et al., 2007;Socolowski and Takaki, 2004). It has antimicrobial (Sidjui et al., 2016;Naz et al., 2014;Rojas et al., 2006), antibacterial (Sidjui et al., 2016), and antioxidant potentials (Rana et al., 2013). ...
... The survival decreasing may be due to the phagodeterrent effect or the action of the secondary metabolites after ingestion (Sapindal et al. 2017). Botanical insecticides can operate in pupal stage, delaying pupae development and consequently inducing metamorphosis deleterious effects (Pratissoli et al., 2008;Rana et al., 2013;Vendramim and Castiglioni, 2000). ...
The high consumption rate of vegetables stimulates the cultivation and increases the demand regarding the adequacy of the production processes. The attack of the pest Plutella xylostella causes high losses by reducing product quality, typifying a phytosanitary problem. This study aimed to verify the bioactivity of aqueous extracts of leaves of Jacaranda decurrens and Jacaranda mimosifolia at concentrations of 5, 10, and 15% on the insect. The choice test was carried out at the laboratory to determine the food effect of plant extracts and evaluate changes in the life cycle of insects exposed to active compounds through the analysis of biological parameters. Plant extracts of J. decurrens and J. mimosifolia presented with phagodeterrent classification in the choice experiments. The three J. decurrens extract concentrations promoted a prolongation of larval and pupal duration, while the duration of individuals treated with J. mimosifolia at 10% was significantly reduced. Occurred reduction in larval survival of individuals treated with aqueous extracts of J. decurrens and J. mimosifolia. Eggs from treatments with aqueous extract of J. decurrens and J. mimosifolia had reduced survival. Pupal survival of individuals treated with extract at 15% showed a significant reduction compared to the treatments at 5% and 10%. Pupae from the treatment with aqueous extract of Jacaranda mimosifolia showed a reduction in biomass in the treatment at 15% differing from the control e 5%. Thus, the aqueous extracts of the species J. decurrens and J. mimosifolia show insecticidal potential in the tests performed on P. xylostella.
... PhGs with a 7,2'-epoxy moiety are rare in the plant kingdom, e.g., compound 103 from Forsythia suspensa which is reported to possess antioxidant as well as antimicrobial activities [49], and compound 104 from Tarphochlamys affinis which was shown to have antioxidant as well as anti-HBV activities [50]. Compound 105 from Jacaranda mimosifolia with antioxidant activity is an example of a PhG with a substituent at C-8 [51]. Compound 106 with melanogenesis inhibitory activity as well as compounds 107 and 108 from Narcissus tazetta var. ...
... PhGs with a 7,2′-epoxy moiety are rare in the plant kingdom, e.g., compound 103 from Forsythia suspensa which is reported to possess antioxidant as well as antimicrobial activities [49], and compound 104 from Tarphochlamys affinis which was shown to have antioxidant as well as anti-HBV activities [50]. Compound 105 from Jacaranda mimosifolia with antioxidant activity is an example of a PhG with a substituent at C-8 [51]. Compound 106 with melanogenesis inhibitory activity as well as compounds 107 and 108 from Narcissus tazetta var. ...
Phenylethanoid glycosides (PhGs) are widely distributed in traditional Chinese medicines as well as in other medicinal plants, and they were characterized by a phenethyl alcohol (C₆-C₂) moiety attached to a β-glucopyranose/β-allopyranose via a glycosidic bond. The outstanding activity of PhGs in diverse diseases proves their importance in medicinal chemistry research. This review summarizes new findings on PhGs over the past 10 years, concerning the new structures, their bioactivities, including neuroprotective, anti-inflammatory, antioxidant, antibacterial and antivirus, cytotoxic, immunomodulatory, and enzyme inhibitory effects, and pharmacokinetic properties.
... Several flavonoids, such as luteolin [30] and jacaranone [31], triterpenes, ursolic acid and oleanolic acid [32], have been identified in the genus Jacaranda, and their antioxidant activities have been described [33], [34], [35], [36]. ...
... Considering the concentration-dependent antioxidant and cytotoxic action of jacaranone [46], a compound also isolated from the leaves of Jacaranda mimosifolia [31], the cytotoxic activity of E-Jds was studied in K562 erythroleukemia cells. There was a concentration-dependent cytotoxic activity against the tumor cells studied (Figure 6A), and the reduction in viability occurred through late apoptosis and necrosis ( Figure 6B), as shown by the activation of caspase-3 ( Figure 6C) and the lowered mitochondrial membrane potential ( Figure 6D). ...
Background and Purpose
Leaves of Jacaranda decurrens are used in traditional Brazilian medicine to treat metabolic diseases related to increased reactive oxygen species. The present study evaluated the antioxidant and cytotoxic potential of hydroethanolic extract from the leaves of Jacaranda decurrens subsp. symmetrifoliolata.
Experimental Approach
Phenolic compounds, flavonoids and saponins were evaluated in an ethanol∶water (80∶20, v/v) extract from the leaves of Jacaranda decurrens subsp. symmetrifoliolata (E-Jds). The antioxidant activity of E-Jds was investigated by assessing the following: 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging activity; protection against 2,2′-azobis (2-amidinopropane) dihydrochloride (AAPH)-induced hemolysis of erythrocytes; in vitro and in vivo malondialdehyde dosage; and the ability to activate antioxidant enzymes. K562 leukemia cells were used for the cytotoxic evaluation of E-Jds and for the assessment of the cell death profile through flow cytometry.
Key Results
Phenolic and flavonoid compounds were quantified as 14.38% and 2.15%, respectively, of E-Jds. These phenolic and flavonoid compounds proved to be able to scavenge DPPH free radicals with an IC50 of 9.3±3.3 µg/mL, to protect up to 50% of erythrocytes against AAPH-induced hemolysis and to reduce in vitro and in vivo malondialdehyde levels up to 84% and 22%, respectively. E-Jds also increased glutathione peroxidase enzyme activity, with a concomitant decrease in superoxide dismutase and catalase activity, and exhibited dose-dependent cytotoxic activity on K562 erythroleukemia cells with cell death occurring via both late apoptosis and necrosis.
Conclusions
E-Jds exhibits in vitro and in vivo antioxidant potential, which may be the mechanism mediating the metabolic activities reported in folk medicine. Furthermore, the cytotoxic activity identified in this study contributes with the knowledge of antiproliferative activities that have been described in the literature for the genus Jacaranda.
... Previous phytochemical studies revealed that irridoids [6], flavonoids [7], naphthoquinones [8], limonoids [9] and steroids [10] are the main secondary metabolites isolated from K. africana, while triterpenes [11], flavonoids [12], acetosides [12], quinones [13], phenylpropanoid derivatives [12,14], fatty acid [15] and anthocyanins [16] have been reported from J. mimosifolia. ...
... Table 1. Yeast inhibition zone diameters of compounds isolated from J. mimosifolia (1)(2)(3)(4)(5) and K. africana (6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17) Test Microorganism (C. albicans) ...
From the stem barks of Jacaranda mimosifolia benzoic acid (1), 1-naphthaleneacetic acid, 5-carboxy-1,2,3,4,4a,7,8,8a-octahydro-1,2,4a-trimethyl-[1S-(1α,2β,4aβ,8aα)] (2), betulinic acid (3), lupeol (4) and ursolic acid (5) were isolated. Similarly, lapachol (6), dehydro-α-lapachone (7), 2-acetylfuro-1, 4-naphthoquinone (8), p-coumaric acid (9), caffeic acid (10), nonacosanoic acid, 2-(4-hydroxyphenyl)ethyl ester (11), β-sitosterol (12), kigelinol (13), oleanolic acid (14), β-friedelinol (15), pomolic acid (16), and kojic acid (17) were isolated from the stem barks of Kigelia africana. All the isolated compounds were characterized by using spectroscopic methods especially 1D and 2D NMR and ESI mass spectrometry and comparison with literature data. To the best of our knowledge, compounds 1, 2, 3 and 5, and compounds 11, 14, 15 and 16 were isolated for the first time from Jacaranda mimosifolia and Kigelia africana, respectively. All these compounds were screened for anticandidal activity by agar diffusion method and microbroth dilution technique on four Candida albicans strains (ATCCL26, ATCC12C, ATCCP37039, and ATCCP37037). Among them, compounds 9, 10, and 17 exhibited the highest anticandidal activity that varied between the microbial species (MIC= 0.01 ± 0.00 − 0.03 ± 0.00 mg/mL) on C. albicans ATCCL26, ATCCP37037, ATCCP37039 and ATCC12C strains. Compound 17 was likely the most active against the four Candida albicans strains (MIC= 0.01 ± 0.00 − 0.02 ± 0.00 mg/mL).
... Previous phytochemical studies revealed that irridoids [6], flavonoids [7], naphthoquinones [8], limonoids [9] and steroids [10] are the main secondary metabolites isolated from K. africana, while triterpenes [11], flavonoids [12], acetosides [12], quinones [13], phenylpropanoid derivatives [12,14], fatty acid [15] and anthocyanins [16] have been reported from J. mimosifolia. ...
... Table 1. Yeast inhibition zone diameters of compounds isolated from J. mimosifolia (1)(2)(3)(4)(5) and K. africana (6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17) Test Microorganism (C. albicans) ...
From the stem barks of Jacaranda mimosifolia benzoic acid (1),1-naphthaleneacetic acid, 5-carboxy-1,2,3,4,4a,7,8,8a-octahydro-1,2,4a-trimethyl-[1S-(1α,2β,4aβ,8aα)] ( 2), betulinic acid ( 3), lupeol (4) and ursolic acid (5) were isolated. Similarly, lapachol (6), dehydro-α-lapachone (7), 2- acetylfuro-1, 4-naphthoquinone (8), p-coumaric acid (9), caffeic acid (10), nonacosanoic acid, 2-(4-hydroxyphenyl)ethyl ester (11), β-sitosterol (12), kigelinol (13), oleanolic acid (14), β-friedelinol (15), pomolic acid (16), and kojic acid (17) were isolated from the stem barks of Kigelia africana. All the isolated compounds were characterized by using spectroscopic methods especially 1D and 2D NMR and ESI mass spectrometry and comparison with literature data. To the best of our knowledge, compounds 1, 2, 3 and 5, and compounds 11, 14, 15 and 16 were isolated for the first time from Jacaranda mimosifolia and Kigelia africana, respectively. All these compounds were screened for anticandidal activity by agar diffusion method and
microbroth dilution technique on four Candida albicans strains (ATCCL26, ATCC12C, ATCCP37039, and ATCCP37037). Among them, compounds 9, 10, and 17 exhibited the highest anticandidal activity that varied between the microbial species (MIC= 0.01 ± 0.00 − 0.03 ± 0.00 mg/mL) on C. albicans ATCCL26, ATCCP37037,
ATCCP37039 and ATCC12C strains. Compound 17 was likely the most active gainst the four Candida albicans strains (MIC= 0.01 ± 0.00 − 0.02 ± 0.00 mg/mL).
Keywords: Bignoniaceae; Jacaranda mimosifolia; Kigelia africana; anticandidal activity. © 2014 ACG Publications.
All rights reserved.
... Extracts of various organs of J. mimosifolia are used in several countries including Bangladesh, India and Pakistan to treat hypertension, ulcers, wounds, diarrhea, dysentery and amoebic infections [30,31,32]. In previous phytochemical studies, triterpenes, acetoside, flavonoids, phenylpropanoid derivatives, quinones, anthocyanins and fatty acids have been isolated from the extracts of J. mimosifolia leaves and flowers [33,34]. Despite reports on the phytochemicals, antioxidants and antimicrobial potential of J. mimosifolia extracts, various aspects related to these phytochemicals including polyphenolic compounds, as well as otherother biological activities such as antiinflammatory and cytotoxic activities remain unexplored. ...
Jacaranda mimosifolia trees are grown in frost-free regions globally. The aim of this study was to evaluate the methanol crude extract and various fractions of increasing polarity of J. mimosifolia leaves for bioactive metabolites, as well as antimicrobial, antioxidant and anti-cancer activities. The anti-inflammatory potential of the various fractions of J. mimosifolia leaf extract was studied via the lipoxygenase (LOX) inhibitory assay. Methanol crude extract (ME), derived fractions extracted with chloroform (CF) and ethyl acetate (EAF), and residual aqueous extract (AE) of dried J. mimosifolia leaves were assayed for polyphenolic compounds , their antioxidant, antimicrobial and lipoxygenase (LOX) inhibitory activities, and anticancer properties. Polyphenolic compounds were determined via HPLC while phyto-chemicals (total phenolics, flavonoids, tannins and ortho-diphenol contents), antioxidant activities (DPPH, hydrogen peroxideperoxide, hydroxyl and superoxide radical anions) and LOX were measured via spectrophotometry. Methanol extracts and various fractions were evaluated for antibacterial activities against Bacillus subtilis, Klebsiella pneumonia, Pseudo-monas aeruginosa and Staphylococcus aureus. Antifungal potential of the fractions was tested against three species: Aspergillus flavus, Aspergillus fumigatus and Fusarium oxy-sporum. The highest values for total phenolic content (TPC), total flavonoid content (TFC), flavonols, tannins and ortho-diphenols were in the ME, followed by CF > EAF > AE. ME also had the highest antioxidant activity with EC 50 values 48±1.3, 45±2.4, 42±1.3 and 46±1.3 μg/ mL based on the DPPH, hydrogen peroxide, hydroxyl radical and superoxide radical assays, respectively. TPC and TFC showed a significant, strong and positive correlation with the values for each of these antioxidant activities. ME exhibited anti-inflammatory potential based on its LOX inhibitory activity (IC 50 = 1.3 μg/mL). ME also had the maximum antibacterial and antifungal potential, followed by EAF > CF > AE. Furthermore, ME showed the strongest cytotoxic effect (EC 50 = 10.7 and 17.3 μg/mL) against human hormone-PLOS ONE PLOS ONE | https://doi.org/10.1371/journal.pone. dependent prostate carcinoma (LnCaP) and human lung carcinoma (LU-1) cell lines, respectively. Bioactive compounds present in leaf methanol extracts of J. mimosifolia were identified using gas chromatography-mass spectrometry (GC-MS). Fifteen compounds were identified including phenolic and alcoholic compounds, as well as fatty acids. Our results suggest that J. mimosifolia leaves are a good source of natural products with antioxi-dant, anti-inflammatory and anti-cancer properties for potential therapeutic, nutraceutical and functional food applications.
... However, there is no report of this compound/plant being used for Covid-19 treatment. PG_447 (1,6-bis (1-hydroxy-4-oxo-2,5-cyclohexadiene-1-acetyl)− 3-(para-hydroxybenzene acetyl)-β-glucopyranoside) has been isolated from Jacaranda mimosifolia, a plant from the Bignoniaceae family, occurring in the Americas [66]. PG_514 (terngymnoside B), was isolated from Ternstroemia gymnanthera, a plant used in the TCM to treat carbuncles, sores, boils and mastitis. ...
Since the advent of Covid-19, several natural products have been investigated regarding their in silico interactions with SARS-CoV-2 proteases ˗ 3CLpro and PLpro, two of the most important pharmacological targets for antiviral development. Phenylethanoid glycosides (PG) are a class of natural products present in important medicinal plants and a drug containing this group of active ingredients has been successfully used in the treatment of Covid-19 in China. Thus, a dataset with 567 derivatives of this class was built from reviews published between 1994 and 2020, and their interaction against both SARS-CoV-2 proteases was investigated. The virtual screening was performed by filtering the PGs through the evaluation of scores based on the AutoDock Vina, GOLD/ChemPLP, and GOLD/GoldScore evaluation functions. The bRO5 pharmacokinetic parameters of the PGs ranked in the previous step were analyzed and their interaction with key amino acid residues of the 3CLpro and PLpro enzymes was evaluated. Ninety-eight compounds were identified by computational approaches against PLpro and 80 PGs against 3CLpro. Of these, four interacted with key catalytic residues of PLpro, which is an indicative of inhibitory activity, and three compounds interacted with catalytic key residues of 3CLpro. Of these, five PGs occur in plants of the Traditional Chinese Medicine (TCM), while two are components of plants/formulations currently used in the Covid-19 protocols in China. The data presented here show the potential of PGs as selective inhibitors of SARS-CoV-2 3CLpro and PLpro.
... Altogether, 35 jacaranones were isolated from 37 plant species; three-quarters of the compounds are monomers (n = 26), and the others are dimers (n = 9) (Figures 2 and 3). Although the best sources of jacaranones are Asteraceae species, certain species of the Acanthaceae [3], Bignoniaceae [1,2,[37][38][39][40][41], Delesseriaceae [42], Gesneriaceae [43,44], Oleaceae [45], and Theaceae [4,5] families were also found to be sources of jacaranones (Table 2). Among Asteraceae species, the genus Senecio is represented by 20 jacaranone derivative-producing plant species [36,[46][47][48][49][50][51][52][53][54][55][56][57][58][59][60][61][62]. ...
Jacaranones are a small group of specific plant metabolites with promising biological activities. The occurrence of jacaranones is limited to only a few plant families, with Asteraceae being the most abundant source of these compounds. Therefore, jacaranones can also serve as chemotaxonomic markers. Our phytochemical investigation of Crepis pulchra L. (Asteraceae) resulted in three jacaranone derivatives (jacaranone, 2,3-dihydro-2-hydroxyjacaranone, 2,3-dihydro-2-methoxyjacaranone), and (6R,9S)-3-oxo-α-ionol-β-d-glucopyranoside, fulgidic acid, 12,15-octadecadienoic acid methyl ester, scopoletin and apigenin-7-O-β-d-glucoside. This is the first report on the isolation of jacaranones from a species belonging to the Cichorioideae subfamily of Asteraceae. Jacaranone derivatives were subjected to an in vitro antiproliferative assay against a panel of human cancer cell lines (MCF-7, MDA-MB-231, HeLa, and C33A), revealing high or moderate activities, with IC50 values ranging from 6.3 to 26.5 μM.
... In addition to its horticultural value, J. mimosifolia was found to be a useful biomonitor of soil metals and atmospheric metals Olowoyo, Van Heerden, Fischer, and Baker 2010) and can also play an important role in soil quality improvement (Rigal et al. 2020). A few active compounds, including jacaric acid (Takagi and Itabashi 1981), jacaranone (Xu et al. 2003), phenylethanoids (Rana et al. 2013;Hendra et al. 2019), and flavonoids (Naz et al. 2020), are commonly isolated from different tissues of J. mimosifolia. Thus, this species has a great potential in medicinal applications due to its antioxidant, antimicrobial, and hypotensive properties (Mostafa et al. 2014). ...
Jacaranda mimosifolia D. Don is a deciduous tree widely cultivated in the tropics and subtropics of the world. It is famous for its beautiful blue flowers and pinnate compound leaves. In addition, this tree has great potential in environmental monitoring, soil quality improvement, and medicinal applications. However, a genome resource for J. mimosifolia has not been reported to date. In this study, we constructed a chromosome-level genome assembly of J. mimosifolia using PacBio sequencing, Illumina sequencing, and Hi-C technology. The final genome assembly was ~707.32 Mb in size, 688.76 Mb (97.36%) of which could be grouped into 18 pseudochromosomes, with contig and scaffold N50 values of 16.77 and 39.98 Mb, respectively. A total of 30,507 protein-coding genes were predicted, 95.17% of which could be functionally annotated. Phylogenetic analysis among 12 plant species confirmed the close genetic relationship between J. mimosifolia and Handroanthus impetiginosus. Gene family clustering revealed 481 unique, 103 significantly expanded, and 16 significantly contracted gene families in the J. mimosifolia genome. This chromosome-level genome assembly of J. mimosifolia will provide a valuable genomic resource for elucidating the genetic bases of the morphological characteristics, adaption evolution, and active compounds biosynthesis of J. mimosifolia.
... Extracts of various organs of J. mimosifolia are used in several countries including Bangladesh, India and Pakistan to treat hypertension, ulcers, wounds, diarrhea, dysentery and amoebic infections [30,31,32]. In previous phytochemical studies, triterpenes, acetoside, flavonoids, phenylpropanoid derivatives, quinones, anthocyanins and fatty acids have been isolated from the extracts of J. mimosifolia leaves and flowers [33,34]. Despite reports on the phytochemicals, antioxidants and antimicrobial potential of J. mimosifolia extracts, various aspects related to these phytochemicals including polyphenolic compounds, as well as otherother biological activities such as antiinflammatory and cytotoxic activities remain unexplored. ...
Jacaranda mimosifolia trees are grown in frost-free regions globally. The aim of this study was to evaluate the methanol crude extract and various fractions of increasing polarity of J. mimosifolia leaves for bioactive metabolites, as well as antimicrobial, antioxidant and anticancer activities. The anti-inflammatory potential of the various fractions of J. mimosifolia leaf extract was studied via the lipoxygenase (LOX) inhibitory assay. Methanol crude extract (ME), derived fractions extracted with chloroform (CF) and ethyl acetate (EAF), and residual aqueous extract (AE) of dried J. mimosifolia leaves were assayed for polyphenolic compounds, their antioxidant, antimicrobial and lipoxygenase (LOX) inhibitory activities, and anticancer properties. Polyphenolic compounds were determined via HPLC while phytochemicals (total phenolics, flavonoids, tannins and ortho-diphenol contents), antioxidant activities (DPPH, hydrogen peroxideperoxide, hydroxyl and superoxide radical anions) and LOX were measured via spectrophotometry. Methanol extracts and various fractions were evaluated for antibacterial activities against Bacillus subtilis, Klebsiella pneumonia, Pseudomonas aeruginosa and Staphylococcus aureus. Antifungal potential of the fractions was tested against three species: Aspergillus flavus, Aspergillus fumigatus and Fusarium oxysporum. The highest values for total phenolic content (TPC), total flavonoid content (TFC), flavonols, tannins and ortho-diphenols were in the ME, followed by CF > EAF > AE. ME also had the highest antioxidant activity with EC50 values 48±1.3, 45±2.4, 42±1.3 and 46±1.3 μg/mL based on the DPPH, hydrogen peroxide, hydroxyl radical and superoxide radical assays, respectively. TPC and TFC showed a significant, strong and positive correlation with the values for each of these antioxidant activities. ME exhibited anti-inflammatory potential based on its LOX inhibitory activity (IC50 = 1.3 μg/mL). ME also had the maximum antibacterial and antifungal potential, followed by EAF > CF > AE. Furthermore, ME showed the strongest cytotoxic effect (EC50 = 10.7 and 17.3 μg/mL) against human hormone-dependent prostate carcinoma (LnCaP) and human lung carcinoma (LU-1) cell lines, respectively. Bioactive compounds present in leaf methanol extracts of J. mimosifolia were identified using gas chromatography–mass spectrometry (GC–MS). Fifteen compounds were identified including phenolic and alcoholic compounds, as well as fatty acids. Our results suggest that J. mimosifolia leaves are a good source of natural products with antioxidant, anti-inflammatory and anti-cancer properties for potential therapeutic, nutraceutical and functional food applications.
... Total polyphenol contents (TPC) were determined by the method described by Rana et al. (2013). 100 lL aliquot was mixed with 500 lL folin ciocalteau's reagent. ...
Apple fruit processing is not variety specific in India, which affect the overall quality of the final processed product. The present study was aimed at elucidation of the nutritive value, phenolic content, antioxidant activity and bioactive phenolic constituents of five widely used apple varieties (Royal Delicious, Red Delicious, Golden Delicious, Red Chief and Red Gold) of western Himalayas. The pomace obtained from different varieties was evaluated to assess the fruit quality. Royal Delicious pomace had significantly high (p < 0.05) total dietary fibre content (42.63 ± 1.26%) together with soluble (8.25 ± 0.95%) and insoluble fibre (32.90 ± 0.89%), as compared to other apple varieties. The pomace samples were extracted with 70% aqueous methanol to obtain polyphenol enriched extracts. The results of Folin–Ciocalteau assay showed that hydroalcoholic extract of Royal Delicious pomace exhibit higher phenolic content as compared to other varieties and ranged between 2.19 ± 0.09 and 4.59 ± 0.47 mg GAE/g. Royal Delicious pomace also possess higher antioxidant capacity i.e. 3.35 ± 0.10 mg/g, 2.71 ± 0.10 mg/g and 4.67 ± 0.03 mg/g as measured by DPPH, ABTS free radical scavenging assay and FRAP reducing assay, respectively. The higher phenolic content in Royal Delicious pomace was also confirmed by RP-HPLC-DAD analysis. Results of HPLC analysis revealed the presence of phloridzin (487.07 ± 0.04 µg/g), quercetin (241.18 ± 0.03 µg/g), quercitrin (178.34 ± 0.02 µg/g) and quercetin-3-glucoside (195.21 ± 0.05 µg/g) as major constituents. Present results indicate that Royal Delicious variety is rich in dietary fibre and phenolic compounds that might be used by the food sector as a source of bioactive health promoting constituents/dietary supplements.
... Free-radical scavenging activity of the purified compounds (1-8) against stable DPPH was determined by DPPH-TLC assay method [15]. One μL (1 mg/mL in methanol) of each compound was spotted on precoated silica plate (silica 60 F254) and dried. ...
Objective: Leaves methanol extract of Jacaranda acutifolia Humb. and Bonpl. (JA) family Bignoniaceae was
subjected to phytochemical investigation as well as antioxidant, hepatoprotective, cytotoxic and antihyperglycemic
activities evaluation.
Key findings: Eight compounds were identified: luteolin-7-O-β-D-glucuronide, luteolin-7-O-β-D-glucoside,
aesculetin, luteolin, verbascoside, luteolin-7-O-β-D-glucuronide methyl ester, apigenin-7-O-β-D-glucuronide methyl
ester and apigenin. JA revealed a potent antioxidant activity in vitro superior to vitamin E (DPPH assay; EC50 of 0.43
mg/mL). A potential cytotoxic activity was produced against hepatocellular (HepG2) and cervical (HeLa) carcinoma
cells with IC50 of 6.05 and 16.7 μg, respectively. Treatment with JA extract inhibited the rise in alanine
aminotransferase and aspartate aminotransferase by 33.6% and 36.8% respectively, reduced thiobarbituric acid by
35.7% and decreased the tamoxifen-induced elevation in tumor necrosis factor alpha (TNF-α) level by 42.86%. JA
extract elicited a significant decrease in fasting blood glucose by -59.26%.
Conclusions: Jacaranda acutifolia could be a natural source for antioxidant, hepatoprotective supplements and
could provide a basis for a potential cytotoxic agent. The compounds isolated are responsible at least in part for the
observed effects.
... This assay was performed by following the modified form of previously reported method (Rana et al. 2013). In detail, ABTS ·+ free radical solution was produced by mixing final concentrations of ABTS solution (7 mM) and potassium per sulphate (2.45 mM) in distilled water and incubated under dark for period of 14 -16 h to produce stable free ABTS ·+ radical. ...
Phytochemical investigation of a methanolic extract of aerial parts Actinidia polygama Miq. led to the isolation of one new diacetylated flavonol triglycoside, kaempferol 3-O-[α-L-rhamnopyranosyl(1→3)-(4-O-acetyl)-O-α-L-rhamnopyranosyl(1→6)-(2-Oacetyl)-O-β-D-galactopyranoside] (1) along with 12 known compounds (2-13). The chemical structures were determined using their spectroscopic data including 1D and 2D NMR. To the best of our knowledge, this is the first time that compounds 2, 4, 6, 7, 8, 9, 12 and 13 are isolated from this plant. All purified compounds were tested for free radical scavenging effect using DPPH and ABTS assays. Our results showed that compounds 4, 6, 7 and 13 have potential antioxidative effect for scavenging both DPPH(·) and ABTS(·+) radicals that are comparable with those of ascorbic acid used as positive control, whereas compounds 1 and 2, which are di- and mono- acetylated flavonol triglycoside respectively, were not found to be potent scavengers of free radicals.
... Total phenolic content of each sample extracts and purified fractions was estimated by Folin's Ciocalteau method (Swain and Hillis 1959) with slight modifications (Rana et al. 2013). Aliquots 50 ll of various extracts from plant parts and purified catechins enriched extracts were taken in triplicate sets in 25 ml volumetric flasks. 1 N Folin's Ciocalteau reagent (1 ml) was added followed by 1 ml of saturated Na 2 CO 3 solution. ...
Comparative investigation of major phytoconstituents was performed from various parts of tea plant viz. apical bud, subtending 1st–5th leaf, stem, coarse leaves, flowers, fruits and roots. From the results of comparative RP-HPLC-DAD analysis it was found that underutilized tea parts especially coarse leaves, flowers and fruits contains abundant amount of phenolics (17.5%) and catechins (4–5%). From these underutilized tea plant parts the catechins were extracted and purified and then screened for their anticancer, immunomodulatory effect and antimicrobial activity against food borne pathogens. The results showed that tea fruit extract exhibited higher toxicity against oral cancer cells and also promotes proliferation of mice splenocytes. The results of antimicrobial studies revealed the inhibitory effect of these extracts against both gram positive and gram negative bacteria. These investigations clearly demonstrated that the underutilized tea plant parts could act as economical and sustainable bioresource of functionally active constituents which further lead to the development of new cost-effective nutraceuticals and other formulations.
... The total phenolic contents of apple leaves extracts obtained using various solvents (ALE-7, ALE-5, ALE, ALM-7, ALM-5 and ALM) were determined by spectrophotometric method (Swain and Hillis, 1959;Rana et al., 2013). The absorbance of reaction mixture was measured at 735 nm using spectrophotometer (T 90 + , PG instruments Ltd). ...
Apple (Malus domestica Borkh.) leaves are good source of polyphenols. Considering the increasing demand of such phytochemicals, particularly in healthcare sector, the objective of this study was to evaluate the bioactivity of apple leaves phenolics. Different solvent mediated extracts obtained from the apple leaves were assessed for presence of phenolic compounds. Among different extracts, the highest phenolic content of 30.38 ± 0.50 mg/g were recorded in 70% aqueous ethanol (ALE-7) with subsequent high antioxidant value (IC50 49.16 μg/mL) by ABTS assay. RP-HPLC-DAD phenolic profiling of leaves extract, irrespective of solvent used for extraction, revealed presence of five major compounds with maximum yield of phloridzin (24.43 ± 0.05 mg/g), followed by quercitrin (2.06 ± 0.05 mg/g), quercetin-3-O-glucoside (1.55 ± 0.001 mg/g), epicatechin (0.37 ± 0.07 mg/g) and phloretin (0.15 ± 0.05 mg/g). ALE-7 extract was further fractionated with hexane (ALH) and ethyl acetate (ALEA), which were evaluated for their in vitro biological activities. ALEA extract exhibited higher nitric oxide (NO) scavenging activity (63.3%) at 200 μg/mL. This fraction also showed maximum lymphocyte proliferation (34%) at 25 μg/mL after 48 h. The antimicrobial testing of isolated fractions revealed that ALH fraction (MIC value ranging from 1.18–2.37 μg/mL) could be a good candidate, especially for controlling food borne pathogen. Furthermore, the in vitro cytotoxicity assessment of different apple leaves fractions was also performed against human cancer cell lines (KB, SiHa and A-549), but none of the fraction was found cytotoxic against selected cell line. In conclusion, the presence of biologically active phenolics in apple leaves makes it a feasible renewable bioresource for extraction of such phytochemicals for the development of nutraceuticals particularly against inflammation and microbial infections.
... The total phenolic content (TPC) of apple pomace was determined using Folin-Ciocalteu's method. 18 Results of total polyphenols were expressed as gallic acid equivalent inmilligram per gram of apple pomace. The total flavonoid content was quantified by the colorimetric method 19 and was expressed as quercetin equivalent inmilligram per gram of apple pomace. ...
Industrial apple pomace, a biowaste generated during apple processing, is rich in cell wall polysaccharides and phenolics. These biologically active compounds are reported to be highly beneficial from the nutritional and health point of view. In the present study, the total phenolic content in the apple pomace aqueous extract (APE) was estimated and evaluated for its possible antioxidant and hepatoprotective efficacy in carbon tetrachloride (CCl4)-induced liver injury mice model. The aqueous extract exhibited 2,2-diphenyl-2-picrylhydrazyl free radical scavenging activity in vitro. Under in vivo study, mice were treated with APE (200 mg and 400 mg/kg body weight) for 2 weeks prior to the administration of CCl4 (30% v/v). The serum liver injury markers alanine transaminase, aspartate transaminase, and alkaline phosphatase were significantly lowered by APE in a dose-dependent manner. The levels of antioxidant parameters superoxide dismutase (SOD), reduced glutathione (redGSH), and lipid peroxidation were also improved by APE in liver homogenate. Histopathological studies revealed that APE treatment significantly lowered the CCl4-induced necrotic changes in the liver. Furthermore, terminal deoxynucleotidyl transferase deoxyuridine triphosphate nick end-labeling assay showed that CCl4-induced apoptosis in the liver was significantly inhibited by APE in a dose-dependent manner. Immunohistochemistry results showed higher expression of nuclear erythroid 2-related factor 2 (Nrf2) in the liver of the APE-treated mice, a key regulator of antioxidative response. In conclusion, the results of the present study revealed the hepatoprotective efficacy of APE by inhibiting CCl4-induced apoptosis, which is due to its antioxidant activity and the ability to induce Nrf2 protein expression.
... pharmacological potential and promising activities as antioxidant activities and in the field of tropical diseases, skin problems and venereal infections and as sources of lectins and trypsin inhibitors (Rana et al. 2013;Arcoverde et al. 2014;Mostafa et al. 2015). ...
A novel biflavonoid [kaempferol (6→8″) apigenin] was isolated from the leaves of Jacaranda acutifolia. The structure was elucidated based on chemical evidence, 1D and 2D spectroscopic analyses as well as spectrometric techniques. The compound showed promising cytotoxic activity against breast cancer cell line MCF-7. The anticancer activity was explained via virtual docking of the isolated compound to the main sites in the human cyclin-dependent kinase2 (CDK2) crystal structure.
... Previous chemical investigations of Jacaranda species have revealed the presence of sterols , triterpenes and various polyphenols (Gachet & Schühly 2009). New phenylethanoid and phenylpropanoids glucosides were isolated from the aerial parts of Jacaranda mimosifolia and the antioxidant activity of the phenylethanoid compound was described (Zaghloul et al. 2011; Rana et al. 2013). Pentacyclic triterpenes oleanolic and ursolic acids were isolated from Jacaranda caroba, the latter being obtained as being 1–2% of the crude extract (Valadares 2009). ...
Jacaranda oxyphylla Cham. (Bignoniaceae) is a shrub found in the Brazilian cerrado and used in folk medicine to treat microbial infections. The aim of this study was to carry out a phytochemical screening and evaluate antioedematogenic, antimicrobial and antiacetylcholinesterase properties of J. oxyphylla crude extracts. All extracts analysed showed presence of terpenoids, which are potentially active chemical substances. A high AChE inhibitory activity for hexane extract from leaves and for the extracts from twigs was found. Ethanol extract from leaves of J. oxyphylla showed activity against Gram-positive (Staphylococcus aureus and Bacillus cereus) and Gram-negative (Escherichia coli) bacteria. This extract was also effective in inhibiting the stages of inflammation evaluated. Biological investigation and phytochemical screening of J. oxyphylla extracts provided additional evidence of its traditional medicinal value.
... Total phenolic content in tea fruits was determined by the Folin-Ciocalteu's method following Rana, Bhangalia, & Singh, 2012. Tea fruit extract (100 µL) was taken into 25-mL volumetric flasks in triplicate. ...
The present study unveils major phenolic antioxidant compounds from Camellia sinensis fruits, followed by their investigation, purification and characterization using HPLC, ESI-MS and NMR studies. The spectrophotometric estimation results have clearly demonstrated that C. sinensis (tea) fruits contain up to 14% of total polyphenols (as gallic acid equivalent) and 7% of flavonoids (as quercetin equivalent) on dry weight basis. Differential solvent-mediated extractions have been performed for quantitative assessment of major phytoconstituents by RP-HPLC analysis. And the results have revealed that these fruits contain adequate amount of tea catechins (4%) along with caffeine (1%) and theanine (0.4%) on dry weight basis. Moreover, purification and characterization of major phytoconstituents such as epigallocatechin, epicatechin, epigallocatechin gallate and epicatechin gallate along with caffeine have been accomplished. Thus, it is clearly demonstrated that tea fruits could act as a possible and reliable source for obtaining major phenolic antioxidants.
The inhibitive behaviour of Jacaranda mimosaefolia flower extract and its green copper nanoparticles (GCuJmNPs) have been studied as green corrosion inhibitors (GCI) using AISI 1018 carbon steel in HCl medium at pH 2, and the green corrosion inhibition efficiency (GCIE) was estimated by Potentiodynamic Polarization Curves (PPC) at 25 + 2 °C. The quantum chemical studies have been also performed using the DFT tool and the electrochemical parameters such as dipole moment (l), EHOMO, ELUMO, energy gap (DE), global hardness (g), chemical softness (S), electron affinity (A), ionization potential (I), the absolute electronegativity (v), the fraction of electron transfer were calculated. The results
showed that J. mimosaefolia flower extract acts as a cathodic inhibitor and protected better than GCuJmNPs, however, the GCuJmNPs made a GCIE in 28%. This work motive continues to study and explore the activity of green metallic nanoparticles as green corrosion inhibitors.
The genus Jacaranda (Bignoniaceae) consists of approximately 50 species, J. cuspidifolia being one member of this genus cultivated all over the world. However, there were no investigations concerning the essential oil composition and antimicrobial activity of the leaves of J. cuspidifolia plant. This study analyzes the chemical composition and biological activity of the essential oil isolated from the leaves of J. cuspidifolia for the first time. The essential oil was obtained by hydrodistillation and investigated by gas chromatography–mass spectrometry (GC-MS) method. The antimicrobial activity of this essential oil against Escherichia coli, Staphylococcus aureus and Candida albicans microbes was tested by the disc diffusion method. Twenty-seven compounds were identified and dominated by linolenic acid (21.52%), followed by (6Z,9Z)-pentadecadien-1-ol (18.03%), geranyl linaloo (11.92%), 9Z,12Z,15Z-octadecatrienoic acid methyl ester (5.57%), 2-butyl-5-hexyloctahydro-1H-Indene (4.56%), octadecenoic acid (3.52%), octadecyl methacrylate (3.35%) and dibutyl phthalate (3.33%). The assay of antimicrobial activity revealed the maximum inhibition zone radii of 8.42, 7.64 and 7.82 mm and the corresponding minimum inhibition concentration (MIC) values of 12.3, 15.9 and 15.4 mg/mL, respectively. Thus, the essential oil of J. cuspidifolia showed potent antimicrobial activity and potential high selectivity against E. coli, S. aureus and C. albicans species.
In this paper, a highly efficient and sustainable synthesis of triarylmethanes through the dehydrative coupling of p-quinols with diaryl carbinols is presented. The catalyst involved in this protocol is in situ generated superacid BF3–H2O from BF3–OEt2. Therefore, moisture has been used as an efficient initiator in this reaction system. A variety of diaryl carbinols and p-quinols have been investigated and found to be compatible to give the triarylmethanes in yields up to 96%.
Background: Traditional Chinese medicine (TCM) is regarded as a large database containing hundreds to thousands of chemical constituents that can be further developed as clinical drugs, such as artemisinin in Artemisia annua. However, effectively exploring novel candidates is still a challenge faced by researchers.
Purpose: In this work, an integrated strategy combining chemical profiling, molecular networking, chemical isolation, and activity evaluation (CMCA strategy) was proposed and applied to systematically characterize and screen novel candidates, and Forsythiae fructus (FF) was used as an example.
Study design: It contained four parts. First, the chemical compounds in FF were detected by ultra-high-performance liquid chromatography-mass spectrometry (UPLC/Q-TOF MS) with data-dependent acquisition, and further, the targeted compounds were screened out based on an in-house database. In the meantime, the representative MS/MS fragmentation behaviors of different chemical structure types were summarized. Second, homologous constituents were grouped and organized based on feature-guided molecular networking, and the nontargeted components with homologous mass fragmentation behaviors were characterized. Third, the novel compounds were isolated and unambiguously identified by nuclear magnetic resonance (NMR). Finally, the anti-angiotensin-converting enzyme 2 (ACE2) activities of isolated chemical constituents were further evaluated by in vitro experiments.
Results: A total of 278 compounds were profiled in FF, including 151 targeted compounds and 127 nontargeted compounds. Among them, 16 were unambitiously identified by comparison with reference standards. Moreover, 25 were classified into potential novel compounds. Two novel compounds were unambiguously identified by using conventional chromatographic methods, and they were named phillyrigeninside D (peak 254) and forsythenside O (peak 155). Furthermore, the ACE2 activity of the compounds in FF was evaluated by modern pharmacological methods, and among them, suspensaside A was confirmed to present obvious anti-ACE2 activity.
Conclusion: Our work provides meaningful information for revealing potential FF candidates for the treatment of COVID-19, along with new insight for exploring novel candidates from complex systems.
Synthesis of complex organic molecules from simple, cheap, and readily available starting materials is one of the most challenging and desirable factors in organic synthesis. In the last two decades, various methods have been developed for the de‐aromatization reaction of planar aromatics compounds which lead to reactive intermediates like 2,5‐cyclohexadienone ketal and para‐quinol having a non‐planar framework. Recently, there is an upsurge of interest in the development of the chemistry of these intermediates due to their inherent dual electrophilic and nucleophilic character. The presence of diverse functionality makes them important scaffolds and thus these are intensively utilized for the development of methodologies towards the synthesis of the highly functionalized and diverse chemical framework. These synthons have also been used in the total synthesis of many natural products. Interestingly, these are also adaptable for asymmetric synthesis. This review is a summary of the recent development of methods for 2,5‐cyclohexadienone ketal and para‐quinol synthesis and their application in natural product synthesis.
Plants are phytochemical hubs containing antioxidants, essential for normal plant functioning and adaptation to environmental cues and delivering beneficial properties for human health. Therefore, knowledge on the antioxidant potential of different plant species and their nutraceutical and pharmaceutical properties is of utmost importance. Exploring this scientific research field provides fundamental clues on (1) plant stress responses and their adaptive evolution to harsh environmental conditions and (2) (new) natural antioxidants with a functional versatility to prevent and treat human pathologies. These natural antioxidants can be valorized via plant-derived foods and products. Cuba contains an enormously rich plant biodiversity harboring a great antioxidant potential. Besides opening new avenues for the implementation of sustainable agroecological practices in crop production, it will also contribute to new strategies to preserve plant biodiversity and simultaneously improve nature management policies in Cuba. This review provides an overview on the beneficial properties of antioxidants for plant protection and human health and is directed to the valorization of these plant antioxidants, emphasizing the need for biodiversity conservation.
The use of traditional herbal remedies as alternative medicine plays an important role in Africa since it forms part of primary health care for treatment of various medical conditions, including wounds. Although physiological levels of free radicals are essential to the healing process, they are known to partly contribute to wound chronicity when in excess. Consequently, antioxidant therapy has been shown to facilitate healing of such wounds. Also, a growing body of evidence suggests that, at least, part of the therapeutic value of herbals may be explained by their antioxidant activity. This paper reviews African herbal remedies with antioxidant activity with the aim of indicating potential resources for wound treatment. Firstly, herbals with identified antioxidant compounds and, secondly, herbals with proven antioxidant activity, but where the compound(s) responsible for the activity has not yet been identified, are listed. In the latter case it has been attempted to ascribe the activity to a compound known to be present in the plant family and/or species, where related activity has previously been documented for another genus of the species. Also, the tests employed to assess antioxidant activity and the potential caveats thereof during assessment are briefly commented on.
In ongoing investigations into colours in Nature, the chemical constituents from the flowers of Acacia pycnantha and Jacaranda mimosifolia D.Don grown in Australia are reported. Eight known secondary metabolites were isolated from the A. pycnantha flower including isosalipurposide (7) which may be responsible for their distinctive colouration. Nine secondary metabolites were isolated from the J. mimosifolia D.Don flower including the new phenylethanoid β-D-glucopyranose (10). All isolated compounds were inactive against bacteria tested at concentration of 32 μg/mL.
Many trees are known to possess important anticancer compounds which include flavonoids and other phenolic compounds, glucosinolates, phytosterols, phytoestrogens, tannins, and protease inhibitors which interrupt with the mitotic activities of abnormal cells. More than 500 compounds belonging to 25 different classes are identified as anticarcinogens. This chapter describes anticancer properties of plants like Bauhinia variegata, Butea monosperma, Callistemon citrinus, Carica papaya, Chukrasia velutina, Cycas revoluta, Dillenia indica, Jasminum officinale, Plumeria rubra, Plumeria obtusa, Magnolia grandiflora, Schleichera oleosa, Sapium sebiferum, and Thuja occidentalis.
This study represents the first report on the chemical composition and antimicrobial activity of the essential oil from the branches of Jacaranda cuspidifolia Mart. Thirty-three compounds were identified by Gas Chromatography-Mass Spectrometry (GC-MS) and the major constituents of the essential oil were Palmitic acid (31.36%), (Z) − 9,17-Octadecadienal (12.06%), Ethyl palmitate (3.81%), Perhydrofarnesyl acetone (2.07%), γ-Maaliene (1.88%), and Cedro (1.42%) and 9,12-Octadecadienoic acid ethyl ester (1.42%). The in vitro antimicrobial activities of the essential oil were evaluated by the disc diffusion method, and the inhibition zones against Escherichia coli, Staphylococcus aureus and Candida albicans were 7.10, 8.20 and 7.25 mm, respectively. The oil showed moderate activities against E. coli, S. aureus and C. albicans with minimum inhibition concentration (MIC) values of 17.3 mg/mL, 12.9 mg/mL and 16.0 mg/mL, respectively.
A general and efficient synthesis of CF3-containing 1,3-dioxolanes using Et3N-catalyzed ketalization/oxa-Michael cascade of quinols with trifluoromethyl ketones is described. The reaction works efficiently under mild reaction conditions and produces the desired products in 68%-95% yields with acceptable diastereoselectivities. In addition, the reaction proceeds smoothly to give the desired product in 92% yield and with high ee (80%) in the presence of a chiral catalyst (DHQ)2PHAL.
A novel phenylethanoid glycoside, 3'-O-methyl isocrenatoside (1), along with two known compounds, methyl caffeate (2) and protocatechuic aldehyde (3), were isolated from the fresh whole plant of Orobanche cernua Loefling. All the isolated compounds (1-3) were elucidated on the basis of spectroscopic analysis including IR, MS and NMR data. The cytotoxic activities of these compounds were evaluated. Results showed that 3'-O-methyl isocrenatoside (1) and methyl caffeate (2) exhibited significant cytotoxicity, with IC50 values of 71.89, 36.97 μg/mL and 32.32, 34.58 μg/mL against the B16F10 murine melanoma and Lewis lung carcinoma cell lines, respectively.
Dihydrobenzo[1,3]dioxolanones, tetrahydrobenzo[d]oxazolones and heterotricyclic derivatives have been stereoselectively synthesized from p-quinols upon reaction with aldehydes or benzaldimines under basic catalysis. Reactions occurred in an experimentally simple one-pot procedure through a domino sequence of two or three reactions. The choice of 4-(dimethylamino)pyridine (DMAP) or 1,4-diazabicyclo[2.2.2]octane (DABCO) as catalyst and MeOH, tetrahydrofuran (THF), or dichloromethane as solvent was essential to achieve the synthesis of bicyclic dioxolanes from aldehydes or bicyclic or tricyclic N,O-aminals from imines. The stereochemical course of these processes is highly dependent on the nature of the electrophiles.
A comparative study was performed on various parts (shoots, roots and flowers) of Incarvillea emodi. The alcoholic extracts of different parts were fractionated with solvents of different polarity and studied for the determination of total polyphenol content and total antioxidant potential. Furthermore, we have isolated major iridoid glucosides from the dried flowers of I. emodi followed by the comparative cytotoxicity studies of these iridoids against five different human cancer cell lines. The results have demonstrated that ethyl acetate fraction of all parts have higher phenolic content (167.87-294.31 mg/g as gallic acid equivalent) and higher total antioxidant potential (252.95-384.64 mg/g as trolox equivalent). The results of in vitro cytotoxicity studies have indicated that boschnaloside (2) possesses promising anticancer potential against three human cancer cell lines, THP-1, A-549 and PC-3, which belong to leukaemia, lung and prostate cancers, respectively, while plantarenaloside (1) expressed relevant cytotoxic activity against THP-1 cell lines of leukaemia.
Processing of apple fruits for juice/cider production generates large volume of pomace at industrial scale. This biomass (cell wall material and pulp tissues) is rich in array of nutrients, especially dietary fiber and polyphenols. Apple fruits confront various processing conditions at industrial level, influencing the biochemical composition of generated pomace, including its phenolic profile. In present study, a simple, fast and reproducible reversed-phase high-performance liquid chromatography method using diode array detector was developed and validated for separation of different phenolics present in industrial apple pomace. The present method showed reliable and reproducible intraday (0.2–4.0 % RSD) and interday (3.7–8.1 % RSD) precision with limits of detection and quantification values in range of 0.14–0.58 and 0.48–1.95 μg ml−1, respectively, for all the phenolics. Different solvent-mediated extraction of dried pomace powder was also performed to evaluate its total antioxidant potential using standard spectrophotometric assays. The major phenolics found in industrial apple pomace extracts were quercetin (1.4–10.3 μg mg−1), phloretin (1.1–9.3 μg mg−1) and phloridzin (0.62–2.0 μg mg−1).
Ternstroemia pringlei represents one of the most widely employed and commercially exploited medicinal plant in Mexico, used popularly as a tranquilizer and for the treatment of insomnia.
To investigate the sedative constituents of the plant through a bio-guided fractionation of extracts derived from calyx and fruits.
Crude extracts with different polarities (CHCl(3), AcOEt, MeOH, aqueous) were prepared and subjected to chromatographic fractionation, leading to the isolation of the sedative compound (1) from the MeOH crude extract. The identity of 1 was unequivocally established by means of 1D and 2D NMR spectroscopic analysis. The sleeping time induced by sodium pentobarbital and the elevated plus-maze models were performed on mice to determine the sedative and anxiolytic activities, respectively. Bioactivity was also investigated though in vitro GABA release experiments using mice brain slices.
The sedative compound was established as jacaranone (1), and its effect was clearly demonstrated through a dose-dependent response analysis (ED(50) = 25 mg/kg mouse weight). When tested in the elevated plus-maze model, none of the extracts from Ternstroemia pringlei displayed anxiolytic activity. GABA release experiments showed that the MeOH and aqueous crude extracts released this neurotransmitter at a ratio of 217 and 179 pmol/g protein, respectively, evidencing the presence of other bioactive constituents in the extracts apart of 1, whose activity was absent in this model.
Although 1 has been isolated and identified in a number of plant species, this is the first time that its sedative effect has been demonstrated. No previous record exists of other sedative compounds having been isolated from Ternstroemia pringlei.
Spectrometric analyses of flavonoids in twenty propolis samples, collected from ten different geographic localities in northern Croatia using two complementary methods, are reported. Flavones and flavonols were determined using aluminum chloride and expressed as quercetine equivalent while flavanones were determined using 2,4-dinitrophenylhydrazine and expressed as naringenin. Contents of flavones and flavonols were similar for most samples and ranged from 2 to 2.3%, except for one sample with a concentration of 1.3% and one sample in which it was not possible to detect flavones and flavonols. The content of flavanones in propolis samples is very variable. 55% of samples contained flavanones between 15 and 24% and 45% of samples between 4 and 14%. Total levels of flavonoids in raw propolis samples ranged between 5 and 26%; for the majority of samples (75%), the total level of flavonoids ranged between 15 and 25.9%. The high variability of flavanone concentration will affect the biological activity of propolis preparations.
Bioassay-guided fractionation of the ethanol extract of Senecio scandens led to the isolation of four new compounds 1-4. These compounds were obtained as tautomeric mixture of alpha/beta epimers, but their structures were confirmed unambiguously by 1D and 2D NMR spectra and LC NMR technology. 1H NMR spectra of pure 1alpha and 1beta were furnished by HPLC NMR technology. Compounds 1-4 exhibited moderate cytotoxicities against five tumor cell lines.
A method for the screening of antioxidant activity is reported as a decolorization assay applicable to both lipophilic and hydrophilic antioxidants, including flavonoids, hydroxycinnamates, carotenoids, and plasma antioxidants. The pre-formed radical monocation of 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS*+) is generated by oxidation of ABTS with potassium persulfate and is reduced in the presence of such hydrogen-donating antioxidants. The influences of both the concentration of antioxidant and duration of reaction on the inhibition of the radical cation absorption are taken into account when determining the antioxidant activity. This assay clearly improves the original TEAC assay (the ferryl myoglobin/ABTS assay) for the determination of antioxidant activity in a number of ways. First, the chemistry involves the direct generation of the ABTS radical monocation with no involvement of an intermediary radical. Second, it is a decolorization assay; thus the radical cation is pre-formed prior to addition of antioxidant test systems, rather than the generation of the radical taking place continually in the presence of the antioxidant. Hence the results obtained with the improved system may not always be directly comparable with those obtained using the original TEAC assay. Third, it is applicable to both aqueous and lipophilic systems.
There is currently much interest in phytochemicals as bioactive components of food. The roles of fruit, vegetables and red wine in disease prevention have been attributed, in part, to the antioxidant properties of their constituent polyphenols (vitamins E and C, and the carotenoids). Recent studies have shown that many dietary polyphenolic constituents derived from plants are more effective antioxidants in vitro than vitamins E or C, and thus might contribute significantly to the protective effects in vivo. It is now possible to establish the antioxidant activities of plant-derived flavonoids in the aqueous and lipophilic phases, and to assess the extent to which the total antioxidant potentials of wine and tea can be accounted for by the activities of individual polyphenols.
Methods for the quantitative analysis of anthocyanins, leuco-anthocyanins, flavanols and total phenols in plant tissue extracts are critically examined and suitable modifications of existing methods are described.
The antiradical activities of various antioxidants were determined using the free radical, 2,2-Diphenyl-1-picrylhydrazyl (DPPH*). In its radical form. DPPH* has an absorption band at 515 nm which dissappears upon reduction by an antiradical compound. Twenty compounds were reacted with the DPPH* and shown to follow one of three possible reaction kinetic types. Ascorbic acid, isoascorbic acid and isoeugenol reacted quickly with the DPPH* reaching a steady state immediately. Rosmarinic acid and δ-tocopherol reacted a little slower and reached a steady state within 30 min. The remaining compounds reacted more progressively with the DPPH* reaching a steady state from 1 to 6 h. Caffeic acid, gentisic acid and gallic acid showed the highest antiradical activities with a stoichiometry of 4 to 6 reduced DPPH* molecules per molecule of antioxidant. Vanillin, phenol, γ-resorcylic acid and vanillic acid were found to be poor antiradical compounds. The stoichiometry for the other 13 phenolic compounds varied from one to three reduced DPPH* molecules per molecule of antioxidant. Possible mechanisms are proposed to explain the experimental results.
The antioxidant potentials of a total ethanolic extract of Hypericum perforatum (TE) and fractions were evaluated and correlated with their phenolic contents. The extracts were fully characterised by HPLC–DAD–MS–MS. Kaempferol 3-rutinoside and rutin-acetyl were identified for the first time in TE extracts. The free radical-scavenging properties of TE (EC50=21 μg dwb/ml) and fractions were studied using DPPH. Fractions containing flavonoids and/or caffeoylquinic acids were found to be the main contributors to the free radical-scavenging activity of the TE. Lipid peroxidation, induced with ascorbate/Fe2+, was significantly reduced in the presence of the TE (EC50=26 μg dwb/ml) and fractions containing flavonoids and/or caffeoylquinic acids. The fraction containing flavonoid aglycones was found to be responsible for a major part of the TE protection against lipid peroxidation. Hypericins and hyperforins made no significant contributions to the antioxidant properties of TE. Human consumption of H. perforatum extract or fractions could be beneficial.
In a survey of plants from Ecuador with antiprotozoal activity, Jacaranda glabra was found to show promising activity against the Plasmodium falciparum K1 strain. Subsequently, activity-guided isolation of the dichloromethane extract from the leaves of J. glabra afforded four new phenylethanoid glucosides containing jacaranone-type moieties (1-4), named jacaglabrosides A-D. Their chemical structures were identified using NMR spectroscopy and MS techniques. The compounds were found to be active in vitro against the P. falciparum K1 strain (IC(50) 1, 1.02; 2, 0.56; 3, 0.56; and 4, 0.55 microg/mL) and generally possessed a low cytotoxicity toward L-6 cells, with the exception of compound 1 (IC(50) 1, 8.3; 2, >90; 3, 87; and 4, 85 microg/mL).
The genus Jacaranda, an important representative of the tribe Tecomeae in the family Bignoniaceae, is interesting from both biological and chemical perspectives. In this review, a contemporary summary of biological and pharmacological research on Jacaranda species will be presented and critically evaluated. Significant findings in the treatment of protozoa-caused diseases as well as of skin illnesses have been presented in ethnobotanical reports and recent studies were performed on crude extracts for certain Jacaranda species. Jacaranone, the most important constituent isolated is known to possess anti-cancer activity. Recently, high cutaneous toxicity together with moderate activity against leishmaniasis was described. Very few additional data are available on the biological activities and cytotoxicity of pure compounds from Jacaranda. Thirteen of the forty-nine distinguished species of Jacaranda have been reported in scientific literature as ethnobotanically used or phytochemically investigated. However, information about a chemical profile is available only for six species. The following article gives a critical assessment of the literature to date and aims to show that the pharmaceutical potential of this genus has been underestimated and deserves closer attention.
Butylated hydroxyanisole (BHA) is a synthetic food antioxidant used to prevent oils, fats and shortenings from oxidative deterioration and rancidity. This review depicts the current knowledge on BHA. The physical and chemical characteristics of BHA are summarized and its function as a food antioxidant is made clear. The toxicological characteristics of BHA and its metabolic fate in man and animal are briefly reviewed. Special emphasis is laid on the carcinogenicity of BHA in the forestomach of rodents and to related events in the forestomach and other tissues in experimental animals. At present there is sufficient evidence for carcinogenicity of BHA, but there is hardly any indication that BHA is genotoxic. Therefore risk assessment for this epigenetic carcinogen is based on non-stochastic principles. However, the mechanism underlying the tumorigenicity of BHA is not known. In the last part of this review an attempt is made to unravel the unknown mechanism of carcinogenicity. It is hypothesized that BHA gives rise to tumor formation in rodent forestomach by inducing heritable changes in DNA. Evidence is being provided that reactive oxygen species, in particular hydroxylradicals, may play a crucial role. The key question with respect to risk assessment for BHA is whether or not the underlying mechanism is thresholded, which is important for the choice of the appropriate model to assess the risk, if any, for man and to manage any potential risk.
A method for the screening of antioxidant activity is reported as a decolorization assay applicable to both lipophilic and hydrophilic antioxidants, including flavonoids, hydroxycinnamates, carotenoids, and plasma antioxidants. The pre-formed radical monocation of 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS*+) is generated by oxidation of ABTS with potassium persulfate and is reduced in the presence of such hydrogen-donating antioxidants. The influences of both the concentration of antioxidant and duration of reaction on the inhibition of the radical cation absorption are taken into account when determining the antioxidant activity. This assay clearly improves the original TEAC assay (the ferryl myoglobin/ABTS assay) for the determination of antioxidant activity in a number of ways. First, the chemistry involves the direct generation of the ABTS radical monocation with no involvement of an intermediary radical. Second, it is a decolorization assay; thus the radical cation is pre-formed prior to addition of antioxidant test systems, rather than the generation of the radical taking place continually in the presence of the antioxidant. Hence the results obtained with the improved system may not always be directly comparable with those obtained using the original TEAC assay. Third, it is applicable to both aqueous and lipophilic systems.
Hypothermic and cardiovascular activities of the methanol extract of Jacaranda mimosaefolia leaves were tested. To evaluate the hypotensive properties, anesthetized rats were used and temperature, blood pressure, and cardiac frequency were recorded. In addition, the in vitro effect produced by the extract on induced contraction with norepinephrine (NE) in rat aorta rings was evaluated. The extract produced a significant hypothermic effect with a maximum at 2 h, an effect which was accompanied by hypotension and low cardiac frequency, physiological conditions that were again re-established to the following 2 h. In isolated aorta preparations norepinephrine antagonistic effect was not correlated with the presence of Ca2+, pD2 for NE was modified by the extract, an effect that could explain a blockade of the adrenergic receptors.
Jacaranone and related compounds (1-3) were isolated, along with three triterpenes (4-6), from the fresh fruits of Ternstroemia japonica. The compounds were identified as jacaranone (1), 3-hydroxy-2,3-dihydrojacaranone (2), 3-methoxy-2,3-dihydrojacaranone (3), 3-O-acetyloleanolic acid (4), 3-O-acetylursolic acid (5), and ursolic acid (6). Jacaranone and its derivatives were isolated for the first time from Theaceae. Of the isolated compounds, compound 3 is a new compound. Jacaranone (1) exhibited weak antioxidative effect on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical.