Sesquiterpene lactones of : Pharmacology, pharmacokinetics, toxicity, and structure-activity relationship.

The medicinal part of (Asteraceae) is its dried root, which is one of the commonly used Chinese medicinal materials. Here we reviewed sesquiterpene lactones isolated from over the past ten years in the following aspects of pharmacological activities, pharmacokinetics, toxicology, structure-activity relationship. Pharmacological activities consist of anti-cancer, anti-inflammatory activity, anti-immunity activity, anti-oxidant activity, antimicrobial activity, spasmolytic activity and so on.

Biotransformation of ursolic acid by Alternaria longipes AS3.2875.

Microbial transformation of ursolic acid (1) was carried out by Alternaria longipes AS 3.2875. Six transformed products (2-7) from 1 were isolated and their structures were identified as 3-carbonyl ursolic acid 28-O-β-D-glucopyranosyl ester (2), ursolic acid 3-O-β-D-glucopyranoside (3), ursolic acid 28-O-β-D-glucopyranosyl ester (4), 2α, 3β-dihydroxy ursolic acid 28-O-β-D-glucopyranosyl ester (5), 3β, 21β dihydroxy ursolic acid 28-O-β-D-glucopyranosyl ester (6), and 3-O-(β-D-glucopyranosyl)- ursolic acid 28-O-(β-D-glucopyranosyl) ester (7) based on the analysis of 1D NMR, 2DNMR and MS data.

Three new triterpenoid saponins from the roots of Ardisia crenata and their cytotoxic activities.

Three new triterpenoid saponins, ardisicrenoside O (1), ardisicrenoside P (2) and ardisicrenoside Q (3) together with three known compounds, 3β,16α-dihydroxy-30-methoxy-28, 30-epoxy-olean-12-en, cyclamiretin A 3-O-β-d-glucopyranosyl-(1→2) -α-l-arabinopyranoside and cyclamiretin A 3-O-β-d-glucopyranosyl-(1→4) -α-l-arabinopyranoside were isolated from the roots of Ardisia crenata Sims. Their structures were determined by one- and two-dimensional NMR techniques, including HSQC, HMBC and TOCSY experiments, as well as acid hydrolysis and GC analysis. All isolates were evaluated for the cytotoxic activities on two human cancer cell lines and compounds 3, 5 and 6 showed significant cytotoxicity.

Ophiobolins P-T, five new cytotoxic and antibacterial sesterterpenes from the endolichenic fungus Ulocladium sp.

Five ophiobolane sesterterpenes, ophiobolins P-T, and three known compounds, 6-epi-21,21-O-dihydroophiobolin G, 6-epi-ophiobolin G and 6-epi-ophiobolin K, were isolated from the acetone extract of the endolichenic fungus Ulocladium sp. by using OSMAC method. Their structures were elucidated on the basis of spectroscopic analysis.

Anti-inflammatory and immunomodulatory mechanisms of artemisinin on contact hypersensitivity.

Artemisinin (Art) is a sesquiterpene trioxane lactone from Artemisia annua L., which has been shown to affect immune responses. However, the underlying mechanism remains elusive.

Synthesis and antitumor activity of novel podophyllotoxin derivatives against multidrug-resistant cancer cells.

Seven novel 4β-N-substituted podophyllotoxin derivatives with indole rings were prepared and evaluated for cytotoxicity against human cancer cell lines HeLa, KB, KBV, K562, and K562/AO2. Most of them demonstrated improved antitumor activity and weak multidrug resistance compared to the drugs currently available.

Biotransformation of oleanolic acid by Alternaria longipes and Penicillium adametzi.

Microbial transformation of oleanolic acid (1) was carried out. Six transformed products (2-7) from 1 by Alternaria longipes and three transformed products (8-10) from 1 by Penicillium adametzi were isolated. Their structures were elucidated as 2α,3α,19α-trihydroxy-ursolic acid-28-O-β-d-glucopyranoside (2), 2α,3β,19α-trihydroxy-ursolic acid-28-O-β-d-glucopyranoside (3), oleanolic acid 28-O-β-d-glucopyranosyl ester (4), oleanolic acid-3-O-β-d-glucopyranoside (5), 3-O-(β-d-glucopyranosyl)-oleanolic acid-28-O-β-d-glucopyranoside (6), 2α,3β,19a-trihydroxy-oleanolic acid-28-O-β-d-glucopyranoside (7), 21β-hydroxyl oleanolic acid-28-O-β-d-glucopyranoside (8), 21β-hydroxyl oleanolic acid (9), and 7α,21β-dihydroxyl oleanolic acid (10) based on the extensive NMR studies.

Pro-apoptotic and microtubule-disassembly effects of ardisiacrispin (A+B), triterpenoid saponins from Ardisia crenata on human hepatoma Bel-7402 cells.

Ardisiacrispin (A+B) is a mixture of ardisiacrispins A and B, derived from Ardisia crenata with a fixed proportion (2:1). The present study was conducted to investigate its anticancer activity on human cancer cells and its underlying mechanism of action. The (IC50)s of ardisiacrispin (A+B) on proliferation of several human cancer cell lines were in the range of 0.

Synthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenes and their analogues.

A total synthetic route for two natural dihydrostilbenes with significant cytotoxicity toward human cancer cell lines, (3-(2-(7-methoxybenzo[d][1,3]dioxol-5-yl)ethyl)phenol 1a and 6-(3-hydroxyphenethyl)benzo[d][1,3]dioxol-4-ol 1b), which were isolated from Bulbophyllum odoratissimum Lindl, was developed via Wittig-Horner reaction. The natural products 1a and 1b were obtained in 28% and 20% overall yield, respectively. Additionally, nine analogues, 1c-1k, of the two natural dihydrostilbenes were synthesized and evaluated for their anti-proliferative activity against human SGC-7901, KB and HT-1080 cell lines by MTT assay.

Water-soluble phenolic glycosides from the whole plant of Bulbophyllum odoratissimum.

Aim: To investigate the water-soluble phenolic glycosides from the whole plant of Bulbophyllum odoratissimum.

Methods: Column chromatography techniques were used to isolate the chemical constituents, physico-chemical constants and spectroscopic analysis were employed for structural elucidation.

Results: Bulbophyllinoside (1), a new phenolic glycoside and three known compounds were isolated from the whole plant of Bulbophyllum odoratissimum Lindl.