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Chemical constituents from the fruits of Phyllanthus emblica L

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  • Chengdu In stitute of Biology,Chinese Academy of Sciences
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... The literature survey assembled previously identified active compounds from P.emblica fruits (Liu et al., 2009;Yang and Liu, 2014;Yang et al., 2020). The collected compounds' information and drug resemblance properties were extracted and calculated using PubChem (http s://pubchem.ncbi.nlm.nih.gov/) and SWISSADME (http://www.swiss ...
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Background : Phyllanthus emblica L. fruits (PEf) are thought to be a good source of natural antidiabetic compounds. Nevertheless, the bioactive ingredients and molecular mechanisms of its type 2 diabetes mellitus (T2DM) properties have yet to be established. Here, we implemented a network pharmacology protocol to ascertain its essential compound and mechanisms of action over T2DM. Methods : PEf's bioactive ingredients were mined through a literature study and filtered by employing Lipinski's rule of five. Besides, genes associated with the screened compounds and T2DM were extracted from public databases. A Venn diagram was utilized for retrieving common genes. Cytoscape was used to plot and portray the interconnected network between compounds and intersecting genes. Finally, molecular docking simulations were performed between key compounds and targets. Results : The literature review yielded a total of 57 compounds in PEf, and 38 compounds were filtered based on Lipinski's rule for further investigations. A total of 244 compound-related and 4979 T2DM-targeted genes were extracted, and Venn pinpointed 183 commons among them. Gene set enrichment analysis manifested 15 signaling pathways which were strongly correlated with the mechanism of PEf against T2DM, with the pivotal mechanism being the diminution of oxidative stress, vascular calcification, and the augmentation of superoxide dismutase 1 expression via the inactivation of a number of co-regulated genes in the AGE-RAGE signaling pathway. In addition, the study of molecular docking affirms that Quercetin is the essential compound in T2DM therapy owing to its greater binding affinity among ten proteins connected with the AGE-RAGE signaling cascade. Conclusion : Our study illustrates the pharmacological proof that substantiates the PEf therapeutic effectiveness over T2DM and discovers largely potent PEf chemicals and mechanisms of action against T2DM. Overall, Quercetin might alleviate T2DM by inactivating the AGE-RAGE signaling pathway.
... The presence of various phytoconstituents such as chlorogenic acid (17.43 mg), gallic acid (37.95 mg), quercetin (2.01 mg), and ellagic acid (71.20 mg) was identified per 100 mL of E. officinalis fruit juice [76]. Ellagic acid, gallic acid, (3,6-di-O-galloyl-D-glucose), 1-Ogalloyl-beta-D-glucose, 3-Ethylgallic acid, quercetin, chebulagic acid, (1,6-di-O-galloyl beta D glucose), corilagin, chebulinic acid, and isostrictiniin are among the different compounds extracted and identified in amla [77]. Flavonoids contained in amla generally include kaempferol 3-O-a-L-(600-methyl)-rhamnopyranoside, quercetin, and kaempferol 3-O-a-L-(600-ethyl) rhamnopyranoside [78]. ...
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The current study was aimed at evaluating the antihyperalgesic effects of lignans (phyllanthin and hypophyllanthin) and tannin (corilagin) rich three standardized extracts of Phyllanthus amarus in a model of chronic musculoskeletal inflammatory pain. Three percent carrageenan injected in the gastrocnemius muscle produced hyperalgesia to mechanical and heat stimuli ipsilaterally, which spreads to the contralateral side within 7 to 9 days. To investigate the effects on chronic thermal and mechanical hypersensitivity, three extracts of P. amarus in three doses (100, 200, and 400 mg/kg) were administered to animals intraperitoneally from 14th day to 22nd day after intramuscular injection of carrageenan. It was observed that intraperitoneal administrations of Phyllanthus extracts showed antihyperalgesic activity, as they elevated thermal and mechanical threshold, which was supported by histopathological observations along with reduction in prostaglandin E2 (PGE2) concentration. In conclusion, we strongly suggest that the observed antihyperalgesic and antiinflammatory effects of P. amarus in current pain model are mediated via spinal or supraspinal neuronal mechanisms, mainly by inhibition of PGE2. Modulation of chronic muscular inflammation may be due to presence of phytoconstituents like phyllanthin, hypophyllanthin, and corilagin, which offers a promising means for treatment of chronic muscle pain. Copyright © 2015 John Wiley & Sons, Ltd. Copyright © 2015 John Wiley & Sons, Ltd.
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Two new ellagitannin dimers, euphorbins G (20) and H (21), together with 12 known polyphenols, were isolated from the leaves of Euphorbia prostrata (E. chamaesyce). Their structures, having 1C4 and 4C1 glucopyranose cores in each molecule, were established by spectroscopic and chemical methods. These new dimers, and 13 known hydrolyzable tannins, among which six are the same as those from E.prostrata, were also isolated from E.makinoi.
Article
Together with ten hydolyzable tannins and related compounds (1-10), three novel dimeric ellagitannins, excoecarianin (11), and excoecarinins A (13) and B (16), possessing a dehydrohexahydroxydiphenoyl or an elaeocarpusinoyl group, have been isolated from the leaves of Excoecaria kawakamii HAYATA (Euphorbiaceae). The structures of these tannins were established on the basis of spectroscopic and chemical evidence.
Article
Together with eleven known compounds (1-11), seven new tannins, 3-desgalloylterchebin (12), macaranins A, B and C, and macarinins A, B and C, have been isolated from the leaves of Macaranga sinensis (BAILL.) MUELL.-ARG. (Euphorbiaceae). Macaranins A (14), B (13) and C (17) have been determined on the basis of chemical and spectroscopic evidence to be hydrolyzable tannins possessing a novel acyl group (macaranoly group) at the 3, 6-positions of the 1C4 (or skew boat) β-D-glucopyranose ring, while macarinins A (18), B (15) and (16) were characterized as those having a tergalloyl group at the same positions.
Article
Further chemical examination of the bark and the leaves of Mallotus japonicus (THUNB.) MUELLER-ARG. (Euphorbiaceae) has led to the isolation of two new tannins [named mallotannins A (16) and B (18)]. Based on chemical and spectroscopic evidence, the structures of 16 and 18 were established to be dimeric hydrolyzable tannins in which the free carboxylic acid in mallotinic acid is connected to the C-6 position of bergenin and D-glucose, respectively. On the other hand, fifteen known tannins and related compounds have been isolated from the leaves of M. philippinensis (LAM.) MUELLER-ARG. and identified by comparisons of their physical and spectral data with those of authentic samples. In addition, a survey of tannin patterns in Mallotus species is presented.
Article
During the process of exploring bioactive lead compounds from Phyllanthus species, two new glycosides including an arylnaphthalene lignan, diphyllin 4-O-α-l-arabinopyranosyl-(1 → 3)-α-l-arabinopyranoside (1), and a phenolic compound, 3,4,5-trimethoxybenzyl alcohol 7-O-α-l-arabinofuranosyl-(1 → 6)-β-d-glucopyranoside (2), were isolated from the methanol extract of the whole plants of Phyllanthusglaucus Wall. ex Müll. Arg. In addition, 31 known compounds, including 19 lignan derivatives (3-21), four phenylpropanoids (22-25), seven simple phenolics (26-32) and one monoterpenoid (33) were obtained. Their structures were determined on the basis of the HR-ESI-MS, 1D and 2D NMR spectroscopic analysis, and pre-column derivative/chiral HPLC analysis in case of 1 for the absolute configurations. All these compounds were obtained from P. glaucus for the first time. Moreover, the known lignan glycoside, phyllanthusmin C (5) showed in vitro cytotoxicities against HL-60, MCF-7 and SW480 cells with IC50 values of 9.2 ± 0.2, 19.2 ± 1.7 and 20.5 ± 0.9, respectively.
Article
Two new dimeric dehydroellagitannins, named euphorbin A (6) and euphorbin B (7), were isolated from the aerial parts of Euphorbia hirta, and their structures, containing 4C1 and 1C4 glucopyranose residues and a dehydrohexahydroxydiphenoyl group, were elucidated on the basis of chemical and spectral studies. Five monomeric hydrolyzable tannins, i.e., 2, 4, 6-tri-O-galloyl-D-glucose, 1, 3, 4, 6-tetra-O-galloyl-β-D-glucose, 1, 2, 3, 4, 6-penta-O-galloyl-β-D-glucose, geraniin and terchebin, as well as two quinic acid esters, i.e., 5-O-caffeoylquinic acid and 3, 4-di-O-galloylquinic acid, and three flavonol glycosides were also isolated.
Article
A chemical examination of the leaves of Mallotus repandus (WILLD.) MUELLER-ARG. (Euphorbiaceae) has led to the isolation of four new hydrolyzable tannins, named repandusinin (10), repandusinic acids A (11a) and B (14a) (as monopotassium salts) and mallotinin (15), together with glucogallin (1), eugeniin (2), corilagin (3), punicafolin (4), geraniin (5), furosin (6), mallotinic acid (7), mallotusinic acid (8) and brevifolin carboxylic acid (9). Based on the chemical and spectroscopic evidence, repandusinin was assigned the structure (10) in which brevifolin carboxylic acid is attached to the C-4 position of the glucose moiety in mallotinic acid, while repandusinic acids A and B were characterized as 1-O-galloyl-3, 6-(R)-hexahydroxydiphenoyl-(11a) and 1-O-galloyl-3, 6-(R)-valoneayl-4-O-(4'-dehydrochebuloyl)-β-D-glucoses (14a), respectively. Similarly, mallotinin was found to have the structure (15) possessing a new acid, mallotic acid, linked to the C-2 position of the corilagin moiety.
Article
A chemical examination of the tannins in the leaves of Macaranga tanarius (L.) MUELL. et ARG. (Euphorbiaceae) has led to the isolation of seven new hydrolyzable tannins (22-28), together with twenty-one known tannins (1-21). On the basis of chemical and spectroscopic evidence, the structures of compounds 22-28 were established as 1, 4-di-O- galloyl-α-D-glucopyranose (22), 3, 4-di-O-galloyl-D-glucopyranose (23), galloylpunicafolin (24), galloylgeraniin (25), 1-O- galloyl-3-O-brevifolincarboxyl-β-D-glucopyranose (26), 1, 2, 4-tri-O-galloyl-3, 6-(S)-hexahydroxydiphenoyl-β-D-glucopyranose (macaranganin) (27) and 1, 2, 4-tri-O-galloyl-3, 6-(R)-dehydrohexahydroxydiphenoyl-β-D-glucopyranose (tanarinin) (28).
Article
Two new hydrolysable tannins, chebumeinin A (1) and chebumeinin B (2), together with eight known related compounds (3‒10), were isolated from the fruits of Terminalia chebula. The new compounds were structurally determined by analysis of their spectroscopic data and the known compounds characterized by comparing their spectroscopic data with literature values. All isolates were evaluated by an HCV protease inhibition assay, and some compounds were found to be potently active.
Article
To investigate the chemical constituents of Euphorbia pekinensis roots. METHODS Column and liquid chromatography were used for the isolation of chemical constituents, and their chemical structures were determined using a spectroscopic method. Four compounds were isolated and identified as ziyu glycoside I (1), 3β-α-L-arabinopyranosyloxyurs-12,19(29)-dien-28-oic acid 28-β-D-glucopyranosyl ester (2), lithospermic acid B (3), and senarguine B (4), which were obtained for the first time from the roots of Euphorbia pekinensis.
Article
The air-dried fruit hull of Phyllanthus emblica L. was extracted with 95% ethanol, and then the extract was partitioned by diethyl ether and ethyl acetate (EA). The EA fraction was then subjected to separation and purification using silica gel and Sephadex LH-20 column chromatography repeatedly to obtain five hydrolysable tannins. They were identified as mucic acid 1,4-lactone 3-o-gallate (C1), isocorilagin (C2), chebulanin (C3), chebulagic acid (C4) and isomallotusinin (C5) using mass spectrometry and nuclear magnetic resonance (NMR) spectrometry. Isomallotusinin and chebulanin were identified from emblica dried fruit hull for the first time, and isomallotusinin was the first time identified from Phyllanthus. Furthermore, the antioxidant abilities of these hydrolysable tannins were investigated using DPPH and ABTS+ radical scavenging systems. All hydrolysable tannins showed strong DPPH and ABTS+ radical scavenging activities. Isomallotusinin and chebulagic acid exhibited the highest antioxidant activity compared to other purified compounds tested.
Article
Phytochemical investigation of the leaves and stems of Glochidion wrightii Benth. led to the isolation of one new triterpenoid ester, 3β-tetradecanoyloxy-1β-hydroxylup-20(29)-ene (1), and twenty-nine known compounds (2–30), including (3β,16β)-lup-20(30)-ene-3,16,29-triol (8) reported as a natural product for the first time. Their structures were identified by spectroscopic analysis and by comparison of their spectral data with those reported in the literature. The chemotaxonomic analysis is concordant with the newest molecular phylogenetic and morphological classifications that the genus Glochidion is deeply embedded within the large Phyllanthus.
Article
Three new bergenin derivatives were isolated from the bark of Mallotus japonicus and determined to be 11-O-galloylbergenin, 4-O-galloylbergenin and 11-O-galloyldemethylbergenin. The 13C resonances of bergenin were fully assigned.
Article
The ichtyotoxic lignan justicidin B, ca 0.6% of the dry weight, and the lignan-glucoside phyllanthostatin A were isolated from the chloroform extract of Phyllanthus anisolobus. Two γ-lactones, menisdaurilide and aquilegiolide, were also isolated and their absolute stereostructures determined by the CD allylic benzoate method.
Article
Two lignans, trivially named gaultherins A (1) and B (2), were isolated from the roots of Gaultheria yunnanensis (Ericaceae). Their structures were deduced as 5-methoxy-(+)-isolariciresinol-9,9′-diacetate (1) and (+)-lyoniresinol-9,9′-diacetate (2), based upon physicochemical properties, spectral analyses and chemical degradation.
Article
A chemical investigation of the roots of Euphorbia fischeriana has led to the isolation of three novel gallotannins, 1,3,6-tri-O-, 1,2,6-tri-O- and 1,2,3,6-tetra-O-galloyl-β-d-allopyranoses, together with ellagitannins (corilagin, sanguiin H-5 and tercatain) and 3,4,6-tri-O-galloyl-d-glucose. The structures of these compounds were established from spectroscopic and chemical evidence.
Article
Chemical investigation of Euphorbia thymifolia has led to the isolation and characterization of a new hydrolysable tannin named isomallotinic acid, in addition to 15 known tannins. The structure of isomallotinic acid was established on the basis of spectroscopic and chemical evidence.
Article
Chemical study of Cunonia macrophylla, a New Caledonian Cunoniaceae, based on bioactive effects of a crude methanol extract of the leaves, detected bioactive tannins for the first time in this plant family. These ellagitannins have been identified as ellagic acid-4-O-beta-D-xylopyranoside (6), mallorepanin (3), mallotinic acid (1) along with corilagin (2), chebulagic acid (4), ellagic acid (5) and gallic acid (7) and have been shown to possess antimicrobial activity and to inhibit xanthine oxidase. Antimicrobial effects on bacterial human pathogens (Staphylococcus aureus, Corynebacterium accolans) and on a plant pathogen (Erwinia carotovora) as well as on a human pathogenic yeast (Candida albicans) were investigated. Activity is reported here for the first time for compounds 1, 3, 4 and 6. The inhibitory effects of all molecules against xanthine oxidase in relation to their structure was evaluated and compared. Compound 6 presented the best activity and seems to be of considerable interest for further studies.
Article
Callus and cell suspension cultures of Sapium sebiferum were established and the production of Gallic acid, β-glucogallin, geraniin, furosin, tercatain, chebulagic acid, chlorogenic acid, 1,2,3,6-tetra-O- and 1,2,3,4,6-penta-O-galloyl-β-d-glucoses established. Both in the callus and cell suspension cultures, the main phenolic constituent was geraniin. 1. Ueki, S. Nonaka, G. Nishioka, 1. and Fujiwara, M. 1985 J. Med. Pharm. Soc. WakKAN-YAKU 2,502. 2. Nagasawa, T. Shibutani, S. and Oura, 1-1. 1978 Yakugaku Zasshi 98, 1642. 3. Nagasawa, T. Shibutani, S. and Oura, H. 1980 Yakugaku Zasshi 100, 434. 4. Nagasawa, T. Oura, H. Shoyama, Y. and Nishioka, 1. 1980 Chem. Pharm. Bull. 28,1736. 5. Shibutani, S. Nagasawa, T.' Oura, H. Nonaka, G. and Nishioka, 1. 1 983 Chem. Phllrm. Bull. 31, 2378. 6, Nishizawa, M. Yamagishi, T. Dutschman, G. E. Parker, W.B. Bodner, A.J. Kilkuskie, R. E. Cheng, Y.-C. and Lee, K.-H. 1989 J. Nat. Prod. 52,762. 7. Nonaka, G. Nishioka, I. Nishizawa, M. Yamagishi, T. Kashiwada, Y. Dutschman, G. E. Bodner, A. J. Kilkuskie, R. E. Cheng, Y.-C. and Lee, K.-H. 1990 J. Nat. Prod. 53, 587. 8. Mridula, M. K. Gupta, P. K. and Masearenhas, A. F. 1983 Plant Cell Tiss. Org. Cult. 2,133. 9. Murashige, T. and Skoog, F. 1962 Physiol. Plant. 15, 473. 10. Schmidt, 0. T. and Schmadel, H. 1961 Liebigs Ann. Chem. 649, 149. 11. Court, W. A. 1977 J. Chromatog. 130, 287. 12. Tanaka, T. Nonaka, G. and Nishioka, 1. 1986 Chem. Pharm. Bull. 34, 1039. 13. Haddock, E. A. Gupta, R. K. and Haslam, E. 1 982 J. Chem. Soc. Perkin Trans I 2535. 14. Okuda, T. Yoshida, T. and Hatano, T. 1982 J, Chem. Soc., Perkin Trans I 9. 15. Nishizawa, M. Yamagishi, T. Nonaka, G. and Nishioka, 1. 1982 J. Chem. Soc. Perkin Trans I 2963. 16. Saijo, R. Nonaka, G. and Nishioka, 1. 1989 Chem. Pharm. Bull. 37, 2063. 17. Nishizawa, M. Yamagishi, T. Nonaka, G. and Nishioka, 1. 1983 J. Chem. Soc. Perkin'Trans I 961.
Article
The structure of a new acylated flavonol glycoside from the leaf extract of Euphorbiamaculata was characterized as quercetin 3-O-(2″,3″-di-O-galloyl)-β-D-glucopyranoside. Four new hydrolyzable tannins together with twelve known tannins were also isolated and their structures were established by spectral and chemical means as 1,2,6-tri-O-galloyl-α-D-glucose, 1-O-galloyl-2,4;3,6-di-O-chebuloyl-β-D-glucose (eumaculin E), and dimers (eumaculins B and D) having a tergalloyl and a macaranoyl group as the linking unit of monomers, respectively. Keywords: Euphorbiamaculata, Euphorbiaceae, tannin, eumaculin B, eumaculin E.