Gallates of isoorientin and (2S)-1,2-propanediol glucoside from the leaves of Schoepfia jasminodora

A new flavonoid glycoside, chrysin 6-C-β-rutinoside (chrysin α-L-rhamnopyranosyl-(1→6)-C-β-glucopyranoside; 2), and two new triterpene glycosides, (31R)-31-O-methylpassiflorine (7) and (31S)-31-O-methylpassiflorine (8), along with 14 known glycosides, including three flavonoid glycosides, 1, 3, and 4, six triterpene glycosides, 5, 6, and 9-12, three cyano glycosides, 13-15, and two other glycosides, 16 and 17, were isolated from a MeOH extract of the leaves of Passiflora edulis (passion flower; Passifloraceae). The structures of new compounds were elucidated on the basis of extensive spectroscopic analysis and comparison with literature data. Upon evaluation of compounds 1-17 against the melanogenesis in the B16 melanoma cells induced with α-melanocyte-stimulating hormone (α-MSH), three compounds, isoorientin (1), 2, and (6S,9R)-roseoside (17), exhibited inhibitory effects with 37.3-47.2% reduction of melanin content with no, or almost no, toxicity to the cells (90.8-100.2% cell viability) at 100 μM. Western blot analysis showed that compound 2 reduced the protein levels of MITF, TRP-1, and tyrosinase, in a concentration-dependent manner while exerted almost no influence on the level of TRP-2, suggesting that this compound inhibits melanogenesis on the α-MSH-stimulated B16 melanoma cells by, at least in part, inhibiting the expression of MITF, followed by decreasing the expression of TRP-1 and tyrosinase. In addition, compounds 1-17 were evaluated for their inhibitory effects against the EpsteinBarr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells.

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Glycosidic Inhibitors of Melanogenesis from Leaves of Passiflora edulis

Zhang

Koike

Yamamoto

et al. 2013

Chemistry & Biodiversity

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Hirtionosides A–C, gallates of megastigmane glucosides, 3-hydroxyoctanoic acid glucosides and a phenylpropanoid glucoside from the whole plants of Euphorbia hirta

et al. 2012

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From the 1-BuOH-soluble fraction of a MeOH extract of Euphorbia hirta, collected in the Okinawa islands, three new megastigmane glucoside gallates, named hirtionosides A-C, 3-hydroxyoctanoic acid glucosides and a phenylpropanoid glucoside were isolated along with 15 known compounds. The structures of the new compounds were elucidated by detailed analysis of physical data, including one- and two-dimensional NMR spectra, and those of known compounds were determined by comparison of physico-chemical data with those reported in the literature. The absolute structures of the megastigmanes were determined by comparison of NMR data and Cotton effects in the CD spectra. The modified Mosher's method was applied to determine the absolute structure of the chiral center in 3-hydroxyoctanoic acid. The DPPH radical-scavenging properties of megastigmane glucoside gallates were assayed and, as expected, they showed moderate activity.

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Six new compounds from the flowers of Chrysanthemum morifolium and their biological activities

Yang

Feng

et al. 2019

Bioorganic Chemistry

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Gallates of isoorientin and (2S)-1,2-propanediol glucoside from the leaves of Schoepfia jasminodora

Cited by 4 publications

References 18 publications

Glycosidic Inhibitors of Melanogenesis from Leaves of Passiflora edulis

Glycosidic Inhibitors of Melanogenesis from Leaves of Passiflora edulis

Hirtionosides A–C, gallates of megastigmane glucosides, 3-hydroxyoctanoic acid glucosides and a phenylpropanoid glucoside from the whole plants of Euphorbia hirta

Six new compounds from the flowers of Chrysanthemum morifolium and their biological activities

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