A new pair of butylphthalide diastereomers from the roots of Angelica sinensis.

A new pair of butylphthalide diastereomers, dangguinolide A (1) and dangguinolide B (2), together with two known butylphthalide were isolated from Angelica sinensis. Their structures were determined by extensive spectroscopic analyses, and the absolute configurations of 1 and 2 were assigned via NMR calculations and ECD calculations. Their anti-inflammatory activities have evaluated in vitro.

A novel Alisma orientale extract alleviates non-alcoholic steatohepatitis in mice via modulation of PPARα signaling pathway.

Non-alcoholic fatty liver disease (NAFLD), particularly advanced non-alcoholic steatohepatitis (NASH), leads to irreversible liver damage. This study investigated the therapeutic effects and potential mechanism of a novel extract from traditional Chinese medicine Alisma orientale (Sam.) Juzep (AE) on free fatty acid (FFA)-induced HepG2 cell model and high-fat diet (HFD) + carbon tetrachloride (CCl4)-induced mouse model of NASH. C57BL/6 J mice were fed a HFD for 10 weeks. Subsequently, the mice were injected with CCl4 to induce NASH and simultaneously treated with AE at daily doses of 50, 100, and 200 mg/kg for 4 weeks. At the end of the treatment, animals were fasted for 12 h and then sacrificed. Blood samples and liver tissues were collected for analysis. Lipid profiles, oxidative stress, and histopathology were examined. Additionally, a polymerase chain reaction (PCR) array was used to predict the molecular targets and potential mechanisms involved, which were further validated in vivo and in vitro. The results demonstrated that AE reversed liver damage (plasma levels of alanine aminotransferase (ALT), aspartate aminotransferase (AST), hepatocyte ballooning, hepatic steatosis, and NAS score), the accumulation of hepatic lipids (TG and TC), and oxidative stress (MDA and GSH). PCR array analysis and Kyoto Encyclopedia of Genes and Genomes (KEGG) pathway enrichment analysis revealed that AE protects against NASH by regulating the adipocytokine signaling pathway and influencing nuclear receptors such as PPARα. Furthermore, AE increased the expression of peroxisome proliferator-activated receptor gamma coactivator-1α (PPARGC1α) and reversed the decreased expression of PPARα in NASH mice. Moreover, in HepG2 cells, AE reduced FFA-induced lipid accumulation and oxidative stress, which was dependent on PPARα up-regulation. Overall, our findings suggest that AE may serve as a potential therapeutic approach for NASH by inhibiting lipid accumulation and reducing oxidative stress specifically through the PPARα pathway.

A new butylphthalide from Ligusticum striatum DC.

One new butylphthalide ligusticumolide H (1), together with the known butylphthalides senkyunolide I (2), senkyunolide H (3), (3 R,3'S)-3'-hydroxy-3-butylphthalide (4), (3 R)-4-hydroxy-3-butylphthalide (5) and senkyunolide C (6) was isolated from the rhizome of Ligusticum striatum DC. Their structures were determined by extensive spectroscopic analyses including HR-ESI-MS, 1D and 2D NMR, and the absolute configuration of 1 was established by NMR and ECD calculations. Their effect on NO production in IL-1ß-stimulated chondrocytes was also evaluated.

Three undescribed coumarins from the roots of Angelica pubescens.

Three undescribed coumarins, 6-(3-hydroxy-3-methyl-2-oxobutyl)-7-methoxycoumarin (1), (R)-6-(1,3-dihydroxy-3-methyl-2-oxobutyl)-7-methoxycoumarin (2), angelol N (6), together with four known coumarins were isolated from the roots of Angelica pubescens. Their structures were determined by extensive spectroscopic analyses. The absolute configurations of compounds 2 and 6 were assigned via electronic circular dichroism (ECD). Their inhibitory effects on lipopoly-saccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 cells were evaluated. Compounds 1-4 exhibited moderate inhibitory activities.

Four new flavonol glycosides from the leaves of Ginkgo biloba.

Four new flavonol glycosides, 5, 7, 5'-trihydroxy-3', 4'-dimethoxyflavonol-3-O-α-L-rhamnopyranosyl-(1→6)-ß-D-glucopyranoside (1), quercetin 3-O-(6-trans-feruloyl)-ß-D-glucopyranosyl-(1→2)-α-L-rhamnopyranoside (2), kaempferol 3-O-(6-trans-caffeoyl)-ß-D-glucopyranosyl-(1→2)-α-L-rhamnopyranoside (3), myricetin 3-O-(6-trans-p-coumaroyl)-ß-D-glucopyranosyl-(1→2)-α-L-rhamnopyranoside (4), together with nine known flavonoids and two known lignans, were isolated from the leaves of Ginkgo biloba. Their structures were determined by extensive spectroscopic analyses. Their cardioprotective effects against H2O2-induced apoptosis in H9c2 cells were also evaluated. The flavonol glycosides had stronger activity than the acylated flavonol glycosides at the concentration of 50 µM.

A new ferulic acid ester from Rhodiola wallichiana var. cholaensis (Crassulaceae).

A new ferulic acid ester, 6-feruloyloxyhexanoic acid (1), was isolated along with 10 known ones (2-11), from the concentrated water extract of Rhodiola wallichiana var. cholaensis. Their chemical structures were elucidated on the basis of extensive spectroscopic methods including Two-dimensional nuclear magnetic resonance (2D NMR) experiments. Compound 3 was isolated from this plant for the first time. The protective effects against H2O2-induced myocardial cell injury in cultured H9c2 cells were also evaluated. Compounds 1, 5 and 7-11 provided significant protective effects on H2O2-induced H9c2 cells injury at the concentration of 25 µg/mL. And the protective effects of compound 1 was also investigated by the oxygen-glucose deprivation/reperfusion (OGD/R) tests.

A new flavonol glycoside from the florets of Carthamus tinctorius L.

One new flavonol glycoside, 6-hydroxykaempferol-3-O-ß-D-glucoside-7-O-ß-D-glucuronide (1), together with eight known flavonoids and three known quinochalcones, was isolated from the florets of Carthamus tinctorius L. Their structures were determined by extensive spectroscopic analyses. Their cardioprotective effects against H2O2-induced apoptosis in H9c2 cells were also evaluated; compounds 1, 2, 4-5, 7-10 and 12 provided significant protective effects on H2O2-induced H9c2 cells at the concentration of 25 µg/mL.

[Application of molecularly imprinted technology for separation of PGG from Guizhi Fuling capsule].

1,2,3,4,6-penta-O-galloyl-D-glucose (PGG) is one of the main active compounds of Guizhi Fuling capsule. Molecularly imprinted polymers (MIP) have high affinity toward template molecules synthesized by molecularly imprinted technology for its specific combined sites, which can overcome the shortcoming of traditional separation methods, such as complex operation, low efficiency, using large quantity of solvent and environmental pollution. In this paper, surface molecularly imprinted polymer (SMIP) was prepared by surface imprinting with PGG as the template molecule. Its adsorption capacity was measured by the scatchard equation. The separation of PGG from Guizhi Fuling capsule at preparatived scale was achieved with molecularly imprinted polymer as stationary phase and the purity was 90.2% by HPLC. This method can be used to prepare PGG from Guizhi Fuling capsule with large capacity and is easy to operate. It provides a new method for efficient separation and purification for other natural products.

[Anti-complementary phenolic acids from Lonicera japonica].

OBJECTIVE: To study the anti-complementary phenolic acids from Lonicera japonica. METHOD: The anti-complementary activity-directed isolation was carried out with the hemolysis test as guide. All isolation was evaluated for their in vitro anti-complementary activities. The structures were identified by various spectroscopic data including ESI-MS, 1H-NMR, 13C-NMR data. RESULT: Fourteen compounds were isolated from the EtOAc fraction of L. japonica extracts, including 8 phenolic acids: 5-O-caffeoylquinic acid (1), chlorogenic (2), 4-O-caffeoylquinic acid (3), 3,5-di-O-caffeoylquinic acid (4), 4,5-di-O-caffeoylquinic acid (5), 3,4-di-O-caffeoylquinic acid (6), caffeic acid (7) and methyl caffeate acid (8); 3 iridoids: secologanoside (9), sweroside (10) and secoxyloganin (11); and 3 flavonoids: luteolin (12), quercetin (13) and kaempferol (14). Compounds 1-9 and 11-14 showed anti-complementary activity in different extents and 3,5-di-O-caffeoylquinic acid (4) exhibited the most significant activity against the classical pathway. CONCLUSION: Compound 14 is obtained from this plant for the first time, phenolic acids are the main anti-complementary constituents of L. japonica and 3,5-di-O-caffeoylquinic acid(4) is a potential complement inhibitor with strong activity, which worthy to be studied further in the future.

[Chemical constituents from Artemisia annua].

OBJECTIVE: To investigate the chemical constituents of dried whole plants of Artemisia annua. METHOD: The chemical constituents were isolated by repeated silica gel chromatography, medium pressure column chromatography, and semi-preparative HPLC, and their structures were elucidated by spectroscopic analyses and comparison of NMR data with those reported in literature. RESULT: 15 compounds were isolated and identified to be 5-O-[(E)-Caffeoyl] quinic acid(l), 1,3-di-O-caffeoylquinic acid(2), 4 5-di-O-caffeoylquinic acid(3), 3, 5-di-O-caffeoylquinic acid (4), 3, 4-di-O-caffeoylquinic acid (5), methyl-3,4-di-O-caffeoylquinic acid(6), methyl-3,5-di-O-caffeoylquinic acid(7), 3,6'-O-diferuloylsucrose(8), 5'-ß-D-glucopyranosyloxyjasmonic acid(9), Scopoletin(10), scoparone (11), 4-O-ß-D-glucopyranosyl-2-hydroxyl-6-methoxyacetophenone (12), chrysosplenol D (13), casticin (14), chrysosplenetin(15). CONCLUSION: Compounds 2, 6, 8 and 9 are obtained from the Artemisia genus for the first time. Compounds 7 and 15 are obtained from this plant for the first time.