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Three new polyketides including two benzophenone derivatives, penibenzones A and B (1 and 2), and a new phthalide derivative, penibenzone C (3), along with six known compounds, were isolated from the solid-substrate cultures of the endophytic fungus Penicillium purpurogenum IMM003. Their structures were elucidated on the basis of spectroscopic data (UV, IR, HRESIMS, 1D and 2D NMR). All compounds were evaluated for inhibitory activity against pancreatic lipase, but none of them displayed activity. [ABSTRACT FROM AUTHOR]

Three new minor valepotriate isomers, jatamanvaltrates Z1 (1), Z2 (2), and Z3 (3), have been isolated from the whole plants ofValeriana jatamansi(syn.Valeriana wallichii.). Their structures were elucidated by extensive spectroscopic analysis, especially 2D NMR and ESI-MS/MSn. All isolated compounds displayed moderate cytotoxicity against the lung adenocarcinoma (A549), metastatic prostate cancer (PC-3 M), colon cancer (HCT-8), and hepatoma (Bel7402) cell lines with IC50values of 2.8–8.3 μM. [ABSTRACT FROM PUBLISHER]

Five new indole alkaloid glucosides named isatindigotindolosides A-E (1–5), along with three known analogs (6–8), were isolated from an aqueous extract of theIsatis indigoticaroots. Their structures including the absolute configurations were determined based on comprehensive spectroscopic data analysis, combined with chemical methods and electronic circular dichroism spectra calculations. In the preliminary assays, compounds1,6and7showed antiviral activity against influenza virus A/Hanfang/359/95 (H3N2) with IC50values of 14.6–33.3 μM. Compound1also exhibited inhibitory effect against nitric oxide (NO) production in microglial cell BV2 with an inhibition ratio of 93.0% at 10 μM. [ABSTRACT FROM AUTHOR]

Seven new C14-polyacetylene glucosides codonopilodiynosides A–G (1–7) were isolated from an aqueous extract of theCodonopsis pilosularoots. Their structures were determined by spectroscopic and chemical methods as (–)-(5S,6E,12E)-tetradeca-6,12-dien-8,10-diyn-1,5,14-triol 5-O-β-d-glucopyranoside (1), (–)-(5S,6E,12E)-tetradeca-6,12-dien-8,10-diyn-1,5,14-triol 5-O-β-d-glucopyranosyl-(1″ → 2′)-β-d-glucopyranoside (2), (–)-(5S,6E,12E)-tetradeca-6,12-dien-8,10-diyn-1,5,14-triol 5,14-di-O-β-d-glucopyranoside (3), (–)-(5S,6E)-tetradeca-6-en-8,10-diyn-1,5,14-triol 5-O-β-d-glucopyranoside (4), (–)-(5S,6E,12E)-tetradeca-6,12-dien-8,10-diyn-1,5-diol 5-O-β-d-glucopyranosyl-(1″ → 2′)-β-d-glucopyranoside (5), (–)-(6S,4E,12E)-tetradeca-4,12-dien-8,10-diyn-1,6-diol 6-O-β-d-glucopyranosyl-(1″ → 2′)-β-d-glucopyranoside (6), and (–)-(5S,6E)-tetradeca-6-en-1,5-epoxy-8,10-diyn-14-ol 14-O-β-d-glucopyranosyl-(1″ → 2′)-β-d-glucopyranoside (7), respectively. The absolute configurations of1–7were assigned by enzymatic hydrolysis followed by isolation of glucose and aglycones (1aand4a–7a), and subsequent comparison of specific rotation, TLC, and1H NMR data of the glucose with an authentic sugar sample and application of modified Mosher's method based on the MPA determination rule of ΔδRSvalues for1aand4a,and ΔδSvalues for6a. The configuration of7was assigned by electronic circular dichroism calculations based on the quantum-mechanical time-dependent density functional theory. [ABSTRACT FROM AUTHOR]

Three new decomposition products of valepotriates, valtrals A–C (1–3), and two known products, baldrinal and homobaldrinal, are formed during the isolation procedure of the ethanol extract of the whole plants ofValeriana jatamansi. Their structures were determined by spectroscopic methods including IR, MS, 1D, and 2D NMR experiments. Compounds1–3showed selective cytotoxicity against metastatic prostate cancer (PC-3M) and colon cancer (HCT-8) cell lines. [ABSTRACT FROM PUBLISHER]

Two new lignans, 9-salicyl-(+)-isolariciresinol (1) and gaultheroside G (2), together with seven known compounds, were isolated from the ethanolic extract of the whole plant ofGaultheria yunnanensis. Their structures were determined by extensive NMR and MS analyses. Gaultheroside G (2) was found to have an unusual ether linkage between the 2 and 9′ positions of aryl-tetralin lignan skeleton. All nine compounds were assayed for inhibitory effects against nitric oxide and pro-inflammatory cytokines TNF-α and IL-6 release in LPS-induced RAW 246.7 macrophages, while no significant activities were observed for the evaluated compounds. [ABSTRACT FROM PUBLISHER]

Six new glycosides (1–6) have been isolated from the flower buds of Lonicera japonica. Their structures including the absolute configurations were determined by spectroscopic and chemical methods as (−)-2-hydroxy-5-methoxybenzoic acid 2-O-β-d-(6-O-benzoyl)-glucopyranoside (1), (−)-4-hydroxy-3,5-dimethoxybenzoic acid 4-O-β-d-(6-O-benzoyl)-glucopyranoside (2), (−)-(E)-3,5-dimethoxyphenylpropenoic acid 4-O-β-d-(6-O-benzoyl)-glucopyranoside (3), (−)-(7S,8R)-(4-hydroxyphenylglycerol 9-O-β-d-[6-O-(E)-4-hydroxy-3,5-dimethoxyphenylpropenoyl]-glucopyranoside (4), (−)-(7S,8R)-(4-hydroxy-3-methoxyphenylglycerol 9-O-β-d-[6-O-(E)-4-hydroxy-3,5-dimethoxyphenylpropenoyl]-glucopyranoside (5), and (−)-4-hydroxy-3-methoxyphenol β-d-{6-O-[4-O-(7S,8R)-(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (6), respectively. [ABSTRACT FROM AUTHOR]

Six new glycosidic constituents (1–6), together with 10 known analogs, have been isolated from the bark of Machilus robusta. Structures of the new compounds, including the absolute configurations, were determined by spectroscopic and chemical methods as (−)-nectandrin B-β-d-glucopyranoside (1), (−)-(7R,7′R,8S,8′R)-4,4′-dihydroxy-3,3′-dimethoxy-7,7′-epoxylignan-4-O-β-d-glucopyranoside (2), (−)-(7R,7′R,8S,8′R)-4,4′-dihydroxy-3,3′-dimethoxy-7,7′-epoxylignan-4′-O-β-d-glucopyranoside (3), (−)-(8S,8′R)-4,4′-dihydroxy-3,3′,5′-trimethoxylignan-4′-O-β-d-glucopyranoside (4), (−)-(7R,8R)-syringylglycerol-8-O-β-d-glucopyranoside (5), and (−)-3-hydroxy-2-methyl-4-pyrone-3-O-β-d-xylopyranosyl-(1 → 6)-O-β-d-glucopyranoside (6), respectively. [ABSTRACT FROM AUTHOR]

Six new butanolide derivatives with long aliphatic side chains (1–6), together with 23 known lipophilic constituents, were isolated from the bark of Machilus yaoshansis. Their structures were elucidated by spectroscopic and chemical methods. All the isolates were evaluated for cytotoxic and anti-inflammatory activities. [ABSTRACT FROM PUBLISHER]

Nine new fatty acid derivatives, including seven methoxylated (1, 2, and 4–8) and two hydroxylated (3 and 9) fatty acids, have been isolated from the ethanol extract of the stem bark of Fraxinus sieboldiana. Their structures were determined by spectroscopic methods including IR, MS, 1D, and 2D NMR experiments. The 3- or 9-methoxylated fatty acids are reported for the first time in nature. [ABSTRACT FROM PUBLISHER]

Five new 9,10-anthraquinones (1–5) were isolated from an ethanol extract of the roots of Knoxia valerianoides. Their structures including absolute configuration of 1 were determined by spectroscopic analysis. Compounds 4 and 5 showed moderate activity against nitrogen oxide production in macrophages induced by lipopolysaccharide, at 10− 5 M, with inhibition ratios of 50.4 ± 3.6 and 41.7 ± 2.1%, respectively. [ABSTRACT FROM PUBLISHER]

Four new minor constituents including two cyclodipeptides (1 and 2) and two cyclopentene derivatives (3 and 4), together with four known cyclodipeptides, have been isolated from an ethanolic extract of the tubers of Gymnadenia conopsea. Their structures including absolute configurations were determined by spectroscopic data interpretation combined with chemical methods. Among them, compound 1 contains an abnormal S-(4''-hydroxybenzyl)cysteine residue, 3 and 4 possess [(4-methylcyclopentyl)methyl]benzene and (4-hydroxymethylcyclopentyl)benzene carbon skeletons, respectively, both of which are first found from the natural source. [ABSTRACT FROM AUTHOR]

Two new cyclohexyl-ethanol derivatives, incarvmareins A (1) and B (2), together with two known derivatives, 3 and 4, were isolated from the ethanolic extract of the roots of Incarvillea mairei. The structures of the new compounds were elucidated primarily on the basis of analysis of spectroscopic data. [ABSTRACT FROM AUTHOR]

Seven new C14-polyacetylene glucosides codonopilodiynosides A-G (1-7) were isolated from an aqueous extract of the Codonopsis pilosula roots. Their structures were determined by spectroscopic and chemical methods as (-)-(5S,6E,12E)-tetradeca-6,12-dien-8,10-diyn-1,5,14-triol 5-O-β-D-glucopyranoside (1), (-)-(5S,6E,12E)-tetradeca-6,12-dien-8,10-diyn-1,5,14-triol 5-O-β-D-glucopyranosyl-(1″ → 2')-β-D-glucopyranoside (2), (-)-(5S,6E,12E)-tetradeca-6,12-dien-8,10-diyn-1,5,14-triol 5,14-di-O-β-D-glucopyranoside (3), (-)-(5S,6E)-tetradeca-6-en-8,10-diyn-1,5,14-triol 5-O-β-D-glucopyranoside (4), (-)-(5S,6E,12E)-tetradeca-6,12-dien-8,10-diyn-1,5-diol 5-O-β-D-glucopyranosyl-(1″ → 2')-β-D-glucopyranoside (5), (-)-(6S,4E,12E)-tetradeca-4,12-dien-8,10-diyn-1,6-diol 6-O-β-D-glucopyranosyl-(1″ → 2')-β-D-glucopyranoside (6), and (-)-(5S,6E)-tetradeca-6-en-1,5-epoxy-8,10-diyn-14-ol 14-O-β-D-glucopyranosyl-(1″ → 2')-β-D-glucopyranoside (7), respectively. The absolute configurations of 1-7 were assigned by enzymatic hydrolysis followed by isolation of glucose and aglycones (1a and 4a-7a), and subsequent comparison of specific rotation, TLC, and (1)H NMR data of the glucose with an authentic sugar sample and application of modified Mosher's method based on the MPA determination rule of Δδ(RS) values for 1a and 4a, and Δδ(S) values for 6a. The configuration of 7 was assigned by electronic circular dichroism calculations based on the quantum-mechanical time-dependent density functional theory.