ABSTRACT
Four undescribed spirostan glycosides, (25S)-5α-spirostan- 12-one-2α,3ß-diol-3-O-ß-D-glucopyranosyl-(1â4)-ß-D-galactopyranoside (1), (25S)-5α-spirostan-12-one-2α,3ß-diol-3-O-ß-D-galatopyranosyl-(1â2)-ß-D-glucopyranosyl- (1â4)-ß-D-galactopyranoside (2), (25S)-5α-spirostan-12-one-2α,3ß-diol-3-O-ß-D-glucopyranosyl-(1â2)-[ß-D-glucopyranosyl-(1â3)]-ß-D-glucopyranosyl-(1â4)-ß-D-galactopyranoside (3), and hecogenin 3-O-ß-D-glucopyranosyl-(1â3)-[ß-D-xylopyranosyl-(1â2)]-ß-D-glucopyranosyl-(1â4)-[α-L-rhamnopyranosyl-(1â2)]-ß-D-galactopyranoside (4), together with eleven known compounds (5-15) were isolated from the branches and leaves of Tribulus terrestris. Their chemical structures were established through spectroscopic methods, including HR-ESI-MS, 1D-, and 2D-NMR spectra. Preliminary biological evaluation on NO production inhibitory activity in LPS activated RAW 264.7â cells showed that compoundsâ 1-3, 5, and 6 had significant inhibitory effects with IC50 values ranging from 2.4 to 18.3â µM, compared to that of the positive control compound, dexamethazone (IC50 13.6â µM).
ABSTRACT
In this study, four undescribed bibenzyl derivatives (1-4), together with seven known compounds (5-11) were isolated from the aerial parts of Dendrobium officinale. Their chemical structures were determined to be (7'S,8'S) -9''-acetyldendrocandin U (1), (7'S,8'S) -4'-methoxydendrocandin T (2), (7'R,8'S) -dendrocandin B (3), (1S,2R) -5'''-methoxydendrofindlaphenol C (4) by analyzing of the spectroscopic data including HR-ESI-MS, 1D-, and 2D-NMR spectra. The absolute configurations of compounds 1-4 were determined by the electronic circular dichroism (ECD) spectra. Compounds 1-3, 5, 10 and 11 inhibited α-glucosidase with the IC50 values ranging from 56.3 to 165.3â µM, compounds 1-3, 5, 7-10 inhibited α-amylase with the IC50 values ranging from 65.2 to 177.6â µM.
ABSTRACT
From the methanol extract of the Cryptolepis buchananii fruits, four undescribed pentacyclic triterpenene glycosides (1-4) and five known pentacyclic triterpenenes (5-9) were isolated. Their structures were determined to be uncargenin C 28-O-α-L-rhamnopyranosyl-(1â2)-ß-D-glucopyranosyl ester (1), 3-O-ß-D-glucopyranosyluncargenin C 28-O-α-L-rhamnopyranosyl-(1â2)-ß-D-glucopyranosyl ester (2), 3-O-ß-D-glucopyranosyl-(1â6)-ß-D-glucopyranosyl-6ß,23-dihydroxyursolic acid 28-O-α-L-rhamnopyranosyl-(1â2)-ß-D-glucopyranosyl ester (3), 3-O-ß-D-glucopyranosyl-(1â2)-ß-D-glucopyranosylasiatic acid 28-O-α-L-rhamnopyranosyl-(1â2)-ß-D-glucopyranosyl ester (4), asiatic acid (5), 2α,3ß,23-trihydroxyoleana-11,13(18)-dien-28-oic acid (6), arjunolic acid (7), 6ß-hydroxyarjunolic acid (8), and actinidic acid (9) based on analyses of their HR-ESI-MS, 1D and 2D NMR spectra. All the isolates showed significantly NO production inhibition in LPS-activated RAW264.7 cells with the IC50 values ranging from 18.79 to 37.57â µM, compared to that of the positive control compound, dexamethasone, which showed IC50 value of 14.05â µM.
Subject(s)
Saponins , Triterpenes , Cryptolepis , Esters , Fruit , Glycosides/pharmacology , Glycosides/chemistry , Lipopolysaccharides/pharmacology , Pentacyclic Triterpenes/pharmacology , Saponins/chemistry , Triterpenes/pharmacology , Triterpenes/chemistryABSTRACT
Four undescribed phenolic glycosides including three stilbene derivatives (1 and 3) and sodium salt of 3 (2), and a chalcone glycoside (4), together with thirteen known compounds (5-17) were isolated from the leaves of Syzygium attopeuense (Gagnep.) Merr. & L.M.Perry. Their chemical structures were elucidated to be (Z)-gaylussacin (1), 6''-O-galloylgaylussacin sodium salt (2), 6''-O-galloylgaylussacin (3), 4'-O-[ß-D-glucopyranosyl-(1â6)-glucopyranosyl]oxy-2'-hydroxy-6'-methoxydihydrochalcone (4), gaylussacin (5), pinosilvin 3-O-ß-D-glucopyranoside (6), myricetin-3-O-(2''-O-galloyl)-α-L-rhamnopyranoside (7), myricetin-3-O-(3''-O-galloyl)-α-L-rhamnopyranoside (8), myricetin-3-O-α-L-rhamnopyranoside (9), quercitrin (10), myricetin-3-O-ß-D-glucopyranoside (11), myricetin-3-O-ß-D-galactopyranoside (12), quercetin 3-O-α-L-arabinopyranoside (13), myricetin-3-O-2''-O-galloyl)-α-L-arabinopyranoside (14), (+)-gallocatechin (15), (-)-epigallocatechin (16), and 3,3',4'-trimethoxyellagic acid 4-O-ß-D-glucopyranoside (17) by the analysis of HR-ESI-MS, 1D and 2D NMR spectra in comparison with the previously reported data. Compounds 1-3, 5, and 6 significant inhibition of NO production in LPS-activated RAW264.7 cells, with IC50 values ranging from 18.37±1.38 to 35.12±2.53â µM, compared to a positive control (dexamethasone) with an IC50 value of 15.37±1.42â µM.
Subject(s)
Glycosides , Syzygium , Glycosides/pharmacology , Glycosides/chemistry , Nitric Oxide , Phenols/pharmacology , Sodium , Molecular StructureABSTRACT
Phytochemical investigation on the aerial parts of Elsholtzia blanda Benth. afforded four new oleuropeic acid derivatives (1-4), named as elsholblanosides A-D, respectively, together with 11 known compounds (5-15). Their structures were determined based on extensive analyses of HR-ESI-MS, 1D and 2D NMR, and ECD spectra. Compounds 1-4 and 14 showed moderate NO production inhibition in LPS-activated RAW264.7 cells with their IC50 values ranging from 23.2 to 86.33â µM, compared to that of the positive control compound, dexamethasone, IC50 value of 16.9â µM.
Subject(s)
Cyclohexanecarboxylic Acids , Lamiaceae , Animals , Mice , Lipopolysaccharides/pharmacology , Lamiaceae/chemistry , RAW 264.7 Cells , Molecular StructureABSTRACT
Phytochemical study on the leaves of Amentotaxus yunnanensis led to the isolation of seventeen phenolic compounds including sixteen neolignans and lignans, and one flavone glycoside. Three among the isolates were previously unreported neolignans and named as amenyunnaosides A-C, respectively. Their structures were elucidated by extensive analyses of HR-ESI-MS, 1D and 2D NMR, and ECD spectra. The isolated neolignans potentially inhibited NO production in LPS-activated RAW264.7 cells with their IC50 values ranging from 11.05 to 44.07â µM, compared to that of the positive control compound, dexamethasone, IC50 value of 16.93â µM. Additionally, amenyunnaoside A dose-dependently reduced production of IL-6 and COX-2 but did not effect to that of TNF-α at concentrations of 0.8, 4, and 20â µM.
Subject(s)
Lignans , Lignans/chemistry , Anti-Inflammatory Agents/chemistry , Glycosides/chemistry , Magnetic Resonance Spectroscopy , Plant Leaves/chemistry , Molecular Structure , Nitric OxideABSTRACT
A new isopropyl chromone (1) and a new flavanone glucoside (2) together with eleven known compounds (3-13) were isolated from the leaves of Syzygium cerasiforme (Blume) Merr. & L.M.Perry. Their structures were elucidated as 5,7-dihydroxy-2-isopropyl-6,8-dimethyl-4H-chromen-4-one (1), 5,7-dihydroxyflavanone 7-O-ß-D-(6''-O-galloylglucopyranoside) (2), strobopinin (3), demethoxymatteucinol (4), pinocembrin-7-O-ß-D-glucopyranoside (5), (2S)-hydroxynaringenin-7-O-ß-D-glucopyranoside (6), afzelin (7), quercetin (8), kaplanin (9), endoperoxide G3 (10), grasshopper (11), vomifoliol (12), litseagermacrane (13) by the analysis of HR-ESI-MS, NMR, and CD spectral data. Compounds 1, 2, 5, 6 and 10 inhibited NO production on LPS-activated RAW264.7 cells with IC50 values of 12.28±1.15, 8.52±1.62, 7.68±0.87, 9.67±0.57, and 6.69±0.34â µM, respectively, while the IC50 values of the other compounds ranging from 33.38±0.78 to 86.51±2.98â µM, compared to that of the positive control, NG -monomethyl-L-arginine acetate (L-NMMA) with an IC50 value of 32.50±1.00â µM.
Subject(s)
Flavanones , Syzygium , Chromones/pharmacology , Flavanones/pharmacology , Glucosides/pharmacology , Glucosides/chemistry , Molecular Structure , Nitric Oxide , Plant Extracts/pharmacology , Plant Extracts/chemistry , Syzygium/chemistryABSTRACT
Three new muurolane type sesquiterpene glycosides, named balanoindicosides A - C (1 - 3), were isolated from the whole plant of Balanophora fungosa subsp. indica using various chromatographic methods. Their structures were determined by extensive analysis of HR-ESI-MS and NMR spectroscopy. The stereochemistry of muurolane sesquiterpene backbone was demonstrated by NOESY analysis. Configuration of C-12 in compounds 2 and 3 could be distinguished by chemical shift value of C-14. Compounds 1-3 exhibited weak cytotoxic activity towards HepG-2, HL-60, LU-1, and MCF-7 cell lines.