RESUMEN
In this study, nine triterpene glycosides including seven previously undescribed compounds (1-7), were isolated from leaves of Cryptolepis buchananii R.Br. ex Roem. and Schult. using various chromatographic methods. The chemical structures of the compounds were elucidated to be 3-O-ß-D-glucopyranosyl-(1 â 6)-ß-D-glucopyranosyluncargenin C 28-O-α-L-rhamnopyranosyl-(1 â 2)-ß-D-glucopyranosyl ester (1), 3-O-ß-D-glucopyranosyl-(1 â 2)-ß-D-glucopyranosyluncargenin C 28-O-α-L-rhamnopyranosyl-(1 â 2)-ß-D-glucopyranosyl ester (2), 3-O-ß-D-glucopyranosyl-(1 â 2)-ß-D-glucopyranosyluncargenin C 28-O-ß-D-glucopyranosyl-(1 â 4)-α-L-rhamnopyranosyl-(1 â 2)-ß-D-glucopyranosyl ester (3), 3-O-ß-D-glucopyranosyl-(1 â 2)-ß-D-glucopyranosylhederagenin 28-O-α-L-rhamnopyranosyl-(1 â 2)-ß-D-glucopyranosyl ester (4), 3-O-ß-D-glucopyranosylarjunolic acid 28-O-α-L-rhamnopyranosyl-(1 â 2)-ß-D-glucopyranosyl ester (5), 3-O-ß-D-glucopyranosyl-(1 â 2)-ß- D-glucopyranosyl-6ß,23-dihydroxyursolic acid 28-O-α-L-rhamnopyranosyl-(1 â 2)-ß-D-glucopyranosyl ester (6), 3-O-ß-D-glucopyranosyl-6ß,23-dihydroxyursolic acid 28-O-α-L-rhamnopyranosyl-(1 â 2)-ß-D-glucopyranosyl ester (7), asiatic acid 28-O-α-L-rhamnopyranosyl-(1 â 2)-ß-D-glucopyranosyl ester (8), and 3-O-ß-D-glucopyranosylasiatic acid 28-O-α-L-rhamnopyranosyl-(1 â 2)-ß-D-glucopyranosyl ester (9), through infrared, high-resolution electrospray ionization mass spectrometry, one- and two-dimensional nuclear magnetic resonance spectral analyses. The isolates inhibited nitric oxide production in lipopolysaccharide-activated RAW 264.7 cells, with half-maximal inhibitory concentration (IC50) values of 18.8-58.5 µM, compared to the positive control compound, dexamethasone, which exhibited an IC50 of 14.1 µM.
Asunto(s)
Glicósidos , Óxido Nítrico , Hojas de la Planta , Triterpenos , Triterpenos/química , Triterpenos/farmacología , Triterpenos/aislamiento & purificación , Óxido Nítrico/metabolismo , Glicósidos/química , Glicósidos/farmacología , Glicósidos/aislamiento & purificación , Ratones , Animales , Estructura Molecular , Hojas de la Planta/química , Células RAW 264.7 , Extractos Vegetales/química , Extractos Vegetales/farmacologíaRESUMEN
A phytochemical study of the aerial parts of Piper mutabile C. DC. revealed seven undescribed compounds [two (2-7')-neolignans and five polyoxygenated cyclohexene glycosides] and six known propenylcatechol derivatives. The chemical structures of the isolated compounds were elucidated by extensive HR-ESI-MS and NMR analyses, as well as comparison with the literature. The absolute configurations of the (2-7')-neolignans were confirmed by GIAO 13C NMR calculations with a sorted training set strategy and TD-DFT calculation ECD spectra. The (2-7')-neolignans and polyoxygenated cyclohexene glycosides are unusual in natural sources. Undescribed neolignans 1 and 2 inhibited NO production in RAW 264.7 cells, with respective IC50 values of 14.4 and 9.5 µM.
Asunto(s)
Ciclohexenos , Glicósidos , Lignanos , Óxido Nítrico , Fitoquímicos , Piper , Componentes Aéreos de las Plantas , Óxido Nítrico/biosíntesis , Óxido Nítrico/metabolismo , Óxido Nítrico/antagonistas & inhibidores , Células RAW 264.7 , Ratones , Piper/química , Estructura Molecular , Componentes Aéreos de las Plantas/química , Animales , Fitoquímicos/farmacología , Fitoquímicos/aislamiento & purificación , Lignanos/farmacología , Lignanos/aislamiento & purificación , Lignanos/química , Glicósidos/farmacología , Glicósidos/aislamiento & purificación , Glicósidos/química , Ciclohexenos/farmacología , Ciclohexenos/aislamiento & purificación , ChinaRESUMEN
Two undescribed triterpenes, syzyfolium A (1) and syzyfolium B (2), together with twelve known compounds, terminolic acid (3), actinidic acid (4), piscidinol A (5), threo-dihydroxydehydrodiconiferyl alcohol (6), lariciresinol-4-O-ß-D-glucoside (7), icariol A2 (8), 14ß,15ß-dihydroxyklaineanone (9), garcimangosone D (10), (+)-catechin (11), myricetin-3-O-α-L-rhamnopyranoside (12), quercitrin (13), and 3, 4, 5-trimethoxyphenyl-(6'-O-galloyl)-O-ß-D-glucopyranoside (14) were isolated from the leaves of Syzygium myrsinifolium. Their chemical structures were determined by IR, HR-ESI-MS, 1D and 2D NMR spectra. Compounds 3 and 4 inhibited significantly α-glucosidase with IC50 values of 23.99 and 36.84, respectively, and compounds 1 and 2 inhibited significantly α-amylase with IC50 values of 35.48 and 43.65â µM, respectively.
Asunto(s)
Syzygium , Triterpenos , Syzygium/química , alfa-Glucosidasas , Extractos Vegetales/farmacología , Triterpenos/farmacología , alfa-Amilasas , Inhibidores de Glicósido Hidrolasas/farmacología , Inhibidores de Glicósido Hidrolasas/químicaRESUMEN
Dracaena cambodiana Pierre ex Gagnep. is well known as a medicinal plant and widely distributed in Vietnam. Phytochemical investigation on the trunks of D. cambodiana lead to the isolation of four undescribed compounds (1-4) together with seven known ones (5-11). Their structures were determined to be pennogenin-24-yl-O-ß-D-glucopyranoside (1), 17α-hydroxycambodianoside C (2), (25R)-27-hydroxypenogenin 3-O-α-L-rhamnopyranosyl-(1â3)-[α-L-rhamnopyranosyl-(1â2)]-ß-D-glucopyranoside (3), (3ß,25R)-17α,22α-dihydroxy-furost-5-en-3-yl-O-α-L-rhamnopyranosyl-(1â3)-[α-L-rhamnopyranosyl-(1â2)]-ß-D-glucopyranoside (4), dracagenin A (5), 1-O-ß-D-glucopyranosyl-2-hydroxy-4-allylbenzene (6), 1-O-α-L-rhamnopyranosyl-(1â6)-ß-D-glucopyranosyl-2-hydroxy-allylbenzene (7), 2-O-α-L-rhamnopyranosyl-(1â6)-ß-D-glucopyranosyl-1-hydroxy-allylbenzene (8), cinnamrutinoside A (9), icariside D1 (10), and seco-isolariciresinol 9-O-ß-glucopyranoside (11) by extensive spectroscopic investigation, HR-ESI-MS, 1D and 2D NMR spectra. The anti-inflammatory activity of the isolated compounds was evaluated on macrophages. Compounds 1-6 significantly inhibited nitric oxide production in lipopolysaccharide (LPS)-induced RAW 264.7 macrophages. Among them, compound 1 showed the best inhibitory activity with an IC50 value of 8.90±0.56â µM.
Asunto(s)
Derivados de Alilbenceno , Dracaena , Saponinas , Lipopolisacáridos/farmacología , Estructura Molecular , Óxido Nítrico , Saponinas/farmacología , Saponinas/química , Glucósidos/química , Glucósidos/farmacologíaRESUMEN
Gnetum latifolium var. funiculare Markgr. is a medicinal plant and widely distributed in mountainous areas of Vietnam. Phytochemical investigation on the trunks of this plant afforded eight stilbene derivatives (1-8) including for new compounds (1-4). Their structures were determined based on extensive analyses of HR-ESI-MS, 1D and 2D NMR spectra. Among the isolates, compounds 1-3 showed moderate NO production inhibition in LPS-activated RAW264.7 cells with the IC50 values ranging from 46.81 to 68.10â µM, compounds 4 and 6 showed weak effects with the IC50 values of 96.57 and 79.46â µM, respectively, compared to that of the positive control compound, dexamethasone (IC50 14.20â µM).
RESUMEN
Phytochemical study on the methanol extract of Aglaia odorata leaves resulted in the isolation of four previously undescribed compounds, including three 2,9-deoxyflavonoids and one flavonol-diamide [3 + 2] adduct, and 13 known compounds. The chemical structures of the four undescribed compounds were elucidated on the basis of their IR, HR-ESI-MS, 1D and 2D NMR, and ECD spectra. The results revealed an unprecedented 2,9-deoxyflavonoid framework, which was confirmed by TD-DFT, ECD, and GIAO 13C-NMR calculations using sorted training set methods. The 17 compounds were examined for their ability to inhibit NO production activity in cultured lipopolysaccharide-activated RAW264.7 cells with aglaodoratas A-C, odorine, and epi-odorine inhibiting NO production, with IC50 values in the range of 16.2-24.3 µM. The other investigated compounds had either weak or no activity.