Flavoalkaloids and Flavonoids from Astragalus monspessulanus PUMID/DOI：DOI: 10.1021/acs.jnatprod.5b00502 J Nat Prod. 2015 Nov 25;78(11):2565-71. A new flavonol tetraglycoside, quercetin-3-O-[alpha-l-rhamnopyranosyl-(1 -> 2)-[alpha-L-rhamnopyranosyl-(1 -> 6)]-beta-D-galactopyranosyl]-7-O-beta-D-glucopyranoside (1), and two new flavonol alkaloids, N-(8-methylquercetin-3-O-[alpha-L-rhamnopyranosyl-(1 -> 2)-[alpha-L-rhamnopyranosyl-(1 -> 6)]-beta-D-galactopyranosyl])-3-hydroxypiperidin-2-one (2) and N-(8-methylkaempferol-3-O-[alpha-L-rhamnopyranosyl-(1 -> 2)-[?-l-rhamnopyranosyl-(1 -> 6)]-beta-D-galactopyranosyl])-3-hydroxypiperidin-2-one (3), were isolated from the aerial parts of Astragalus monspessulanus ssp. monspessulanus. Two rare flavonoids with an unusual 3-hydroxy-3-methylglutaric acid moiety, quercetin-3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-[6-O-(3-hydroxy-3-methylglutaryl)-beta-D-galactopyranoside (4) and kaempferol-3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-[6-O-(3-hydroxy-3-methylglutaryl)-beta-d-galactopyranoside (5), were isolated from the aerial parts of A. monspessulanus ssp. illyricus. In addition, the eight known flavonoids alangiflavoside (6), alcesefoliside (7), mauritianin (8), quercetin-3-beta-robinobioside (9), cosmosine (10), apigenin-4'-O-glucoside (11), trifolin (12), and rutin (13) were isolated from aerial parts of A. monspessulanus ssp. monspessulanus. Their structures were elucidated via NMR and HRESIMS data. In a model that tested t-BuOOH-induced oxidative stress on isolated rat hepatocytes, flavonoids 1-13 had statistically significant cytoprotective activity similar to that of silymarin, tested at 60 mu g/mL. The most prominent effects were observed for flavonoids 1, 4, 7, and 12. New triterpene glycoside and other chemical constituents from the leaves of Swartzia apetala Raddi var. glabra PUMID/DOI：DOI: 10.1080/14786419.2013.782493 Nat Prod Res. 2013 Oct;27(20):1888-95. A new triterpene saponin (1) was isolated from a methanol extract of Swartzia apetala Raddi var. glabra, together with the flavonoids mauritianin (2), kaempferol (3) and the triterpene saponin -D-glucopyranosyl 3-hydroxy-olean-12-en-28-oate (4). These compounds were characterised on the basis of their spectral data, mainly one-dimension (1D; H-1, C-13, APT) and two-dimension (2D; H-1-H-1-COSY, HMQC and HMBC) nuclear magnetic resonance (NMR) and HR-ESI-MS, and comparison with values in the literature. The analysis by HR-ESI-MS showed a mass compatible with that of triterpene saponin 1. This proposal was supported by molecular modelling. LC-HR-ESI-MS experiment was also used to evaluate the purity of 1 and allowed to speculate about the possibility of the presence of 5 in very small quantity. The extract and four compounds were assayed for antifungal activity against nine strains of Candida spp. Bioactive phenolic compounds from Catharanthus roseus and Vinca minor PUMID/DOI： Nishibe S, Takenaka T, Fujikawa T, et al. Bioactive Phenolic Compounds from Catharanthus roseus and Vinca minor[J]. Natural Medicines, 1996, 50:378-383. Kaempferol 3-O-alpha-L-rhamnopyranosyl-(1 fwdarw 2)-alpha-L-rhamnopyranosyl-(1 fwdarw 6)-beta-D-galactopyranoside (mauritianin), quercetin 3-O-alpha-L-rhamnopyranosyl-(1 fwdarw 2)-alpha-L-rhamnopyranosyl-(1 fwdarw 6)-beta-Dgalactopyranoside and chlorogenic acid were isolated from the leaves of Catharanthus roseus (L.) G. DON (= Vinca rosea L.), used as the herbal medicine "Herba Catharanthi." Kaempferol 3-O-alpha-L-rhamnopyranosyl- (1 fwdarw 6) -beta-D-glucopyranoside-7- O-beta-D-glucopyranoside, 2,3-dihydroxybenzoic acid, 3-beta-Dglucopyranosyloxy-2-hydroxybenzoic acid (vincoside) and chlorogenic acid were isolated from the leaves of Vinca minor L., used as the herbal medicine "Periwinkles." Mauritianin enhanced the 12-Otetradecanoylphorbol-13-acetate-suppressed delayed-type hypersensitivity in mice, indicating that mauritianin may augment the immune resistance to cancer. 2,3-Dihydroxybenzoic acid showed a potent radical-scavenging activity, which may lower the risk of cancer. 2,3-Dihydroxybenzoic acid prevented the formation of advanced glycation end products (AGEs), which may reduce development of diabetic complications.
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The flowers and leaves of Trifolium repens L. (Fabaceae) were subjected to phytochemical investigation in order to identify their major chemical constituents and to evaluate in vitro antioxidant activity of the isolated compounds against DPPH˙. A total of 12 flavonoids, pterocarpan and methyl caffeate were isolated, then characterised by UV, MS, NMR spectroscopy and identified as quercetin and kaempferol 3-O-(6″-α-rhamnopyranosyl-2″-β-xylopyranosyl)-β-galactopyranosides (1, 2), kaempferol 3-O-(2″,6″-α-dirhamnopyranosyl)-β-galactopyranoside, mauritianin (3), quercetin and kaempferol 3-O-(2″-β-xylopyranosyl)-β-galactopyranosides (4, 5), kaempferol and quercetin 3-O-β-(6″-O-acetyl)-galactopyranosides (6, 7), trifolin (8), hyperoside (9), myricetin 3-O-β-galactopyranoside (10), quercetin (11), ononin (12), medicarpin 3-O-β-glucopyranoside (13) and methyl caffeate (14). Mauritianin, ononin, pterocarpan and methyl caffeate have been reported in this plant for the first time. The compounds 4, 7, 9, 10, and 11 were tested for their antioxidant effect against DPPH˙. All studied compounds were found to have potent activity, but the most effective in the test were compounds 9, 10 and 11 (EC(50) values in the range 7.51-9.52 µM).
Study on the phenolic constituents of the flowers and leaves of Trifolium repens L
Agnieszka Kicel 1, Maria Wolbiś
Objective: To investigate the chemical constituents of the branches and leaves of Polyalthia nemoralis.
Method: The compounds were isolated and purified by silica gel, macroporous adsorption resin and Sephadex LH-20 column chromatographic methods. Their chemical structures were elucidated on the basis of physicochemical properties and spectral data.
Result: Fourteen compounds were isolated and identified as syringic acid (1), 3-methoxy-4-hydroxycinnamic acid (2), vanillic acid (3), 4-hydroxybenzoic acid (4), mauritianin (5), (+)-xylopinidine (6), (+)-oblongine(7), (+)-tembetarine (8), eythritol (9), D-mannitol (10), ethyl-beta-D-glucopyranoside (11), (+)-magnoflorine (12), stepharanine (13), (2S, 4R)-4-hydroxy-2-piperidine-carboxylic acid (14), respectively.
Conclusion: All the compounds were isolated from the genus Polyalthia for the first time; compounds 6 and 13 showed inhibitation activities against multi tumor cell lines.
[Study on chemical constituents from branches and leaves of Polyalthia nemoralis]
Ziming Lu 1, Qingjian Zhang, Ruoyun Chen, Dequan Yu
Four known kaempferol glycosides, mauritianin, clitorin, nicotiflorin and biorobin, have been isolated from the flowers and leaves of Acalypha indica. Some formerly published NMR data were corrected.
Flavonoids from Acalypha indica
A Nahrstedt 1, M Hungeling, F Petereit