Ming-Hua Qiu

Kuguacins F-S, cucurbitane triterpenoids from Momordica charantia.

Chemical investigation of the vines and leaves of Momordica charantia resulted in isolation of fourteen cucurbitane triterpenoids, kuguacins F-S (1-14), including two pentanorcucurbitacins (6 and 7), one octanorcucurbitacin (8), and two trinorcucurbitacins (11 and 12), along with six known analogues. Their structures were elucidated on the basis of extensive spectroscopic and single-crystal X-ray diffraction analyses. Compounds 1-14 exhibited weak anti-HIV-1 activities in vitro.

Protective effects of triterpenoids from Ganoderma resinaceum on H2O2-induced toxicity in HepG2 cells

Ganoderma resinaceum Boud. (Polyporeseae) has long been used for antioxidant, immunoregulation and liver protection. From the fruiting bodies of G. resinaceum, eight new lanostanoids, lucidones D-G (1-4), 7-oxo-ganoderic acid Z2 (5), 7-oxo-ganoderic acid Z3 (6), ganoderesin A (7), and ganoderesin B (8), together with six known lanostanoids (9-14) were isolated. The structures of new compounds were elucidated through extensive spectroscopic analysis. In an in vitro model, ganoderesin B (8), ganoderol B (10) and lucidone A (11) showed inhibitory effects against the increase of ALT and AST levels in HepG2 cells induced by H2O2 compared to a control group in the range of their maximum non-toxic concentration (MNTC). However, compounds 8, 10 and 11 displayed no anti-oxidant activities by DPPH assay. Meanwhile, activation for PXR (Pregnane X Receptor) of ganoderesin B (8), ganoderol B (10) and lucidone A (11) was evaluated; ganoderol (10) exhibited a vital activation for PXR-induced CYP3A4 expression. These results suggested that GTs (Ganoderma triterpenoids) exhibited hepatoprotective activities by lowering ALT and AST levels.

New Cucurbitane Triterpenoids and Steroidal Glycoside from Momordica charantia

Three new cucurbitane triterpenoids 1–3 and one new steroidal glycoside 4, were isolated together with ten known compounds from Momordica charantia. The structures of new compounds were determined to be 19(R)-n-butanoxy-5β,19-epoxycucurbita-6,23-diene-3β,25-diol 3-O-β-glucopyranoside (1), 23-O-β-allopyranosyle-cucurbita-5,24-dien-7α,3β,22(R),23(S)-tetraol 3-O-β-allopyranoside. (2), 23(R),24(S),25-trihydroxycucurbit-5-ene 3-O-{[β-glucopyranosyl(1→6)]-O-β-glucopyranosyl}-25-O-β-glucopyranoside (3), and 24(R)-stigmastan-3β,5α,6β-triol-25-ene 3-O-β-glucopyranoside (4), respectively. Their structures were elucidated by the combination of mass spectrometry (MS), one and two-dimensional NMR experiments and chemical reactions.

Cycloartane triterpenoids from Cimicifuga yunnanensis induce apoptosis of breast cancer cells (MCF7) via p53-dependent mitochondrial signaling pathway

The present study was carried out to investigate the antitumor activity of five cycloartane triterpenoids isolated from Cimicifuga yunnanensis on the breast cancer cell line MCF7 and its corresponding drug resistant subline R‐MCF7, including cimigenol‐3‐O‐β‐d‐xylopyranoside (compound 1), 25‐O‐acetylcimigenol‐3‐O‐β‐d‐xylopyranoside (compound 2), 25‐chlorodeoxycimigenol‐3‐O‐β‐d‐xylopyranoside (compound 3), 25‐O‐acetylcimigenol‐3‐O‐α‐l‐arabinopyranoside (compound 4) and 23‐O‐acetylcimigenol‐3‐O‐β‐d‐xylopyranoside (compound 5). The results showed that compounds 2–5 have relatively high antitumor activity on both MCF7 and R‐MCF7 cells. The involvement of apoptosis as a major cause of cycloartane triterpenoids‐induced cell death was further confirmed. The results of RT‐PCR showed that compounds 2–5 increased the expression of p53 and bax, which led to the loss of mitochondrial potential and then resulted in the activation of caspase‐7. These findings collectively demonstrated that compounds 2–5 induced apoptosis of MCF7 via p53‐dependent mitochondrial pathway. Copyright

Two ellagic acid glycosides from Gleditsia sinensis Lam. with antifungal activity on Magnaporthe grisea

Two ellagic acid glycosides were isolated by bioassay-guided fractionation from the antimicrobial ethyl acetate fraction of the ethanol extract from Gleditsia sinensis spines, and identified as 3-O-methylellagic acid-4′-(5″-acetyl)-α-L-arabinofuranoside (1) and 3-O-methylellagic acid-4′-O-α-L-rhamnopyranoside (2). Both compounds were isolated from this plant species for the first time, and 1 is a new compound. The two compounds showed significant antifungal activity against the spore germination of rice blast fungus Magnaporthe grisea, with an IC50 value of 13.56 µg mL−1 for 1 and 16.14 µg mL−1 for 2.

A new anti-HIV lupane acid from Gleditsia sinensis Lam.

A new lupane acid, 2β-carboxyl,3β-hydroxyl-norlupA (1)-20 (29)-en-28-oic acid (1), together with five known lupane acid derivatives (2–6), were isolated from the stings of Gleditsia sinensis Lam.. Their structures were elucidated on the basis of 1D and 2D NMR techniques. All these known compounds were isolated from this genus for the first time. The new compound 1 showed strong anti-HIV activity.

Isolation and bioactivity evaluation of terpenoids from the medicinal fungus Ganoderma sinense.

A new pentanorlanostane, ganosineniol A (1), eight new lanostane triterpenoids, ganosinoside A (2), ganoderic acid Jc (3), ganoderic acid Jd (4), ganodermatetraol (5), ganolucidic acid γa (6), ganolucidate F (7), ganoderiol J ( 8), and methyl lucidenate Ha ( 9), and a new sesquiterpenoid, ganosinensine (10), together with eleven known triterpenoids (11- 21), were isolated from the fruiting bodies of the fungus Ganoderma sinense. Chemical structures were determined based on spectroscopic evidence, including 1D, 2D NMR, and mass spectral data. Furthermore, all isolates were tested for cytotoxic activity and induction ability of hPXR-mediated CYP3A4 expression. Among them, ganoderic acid Jc (3) displayed selective inhibitory activity against HL-60 cells (IC₅₀ = 8.30 µM), and ganoderiol E (11) exhibited selective cytotoxic activity against MCF-7 cells (IC₅₀ = 6.35 µM). Meanwhile, compounds 5, 7, and ganolucidic acids B and C (19, 20) showed induction ability of hPXR-mediated CYP3A4 expression.

Three new triterpenoids containing four-membered ring from the fruiting body of Ganoderma sinense.

Methyl ganosinensate A (1), ganosinensic acid A (1a), and ganosinensic acid B (2), three new triterpenoids with an unusual four-membered ring skeleton produced by a bond across C-1 to C-11, were isolated from the fruiting body of Ganoderma sinense . Their structures were established on the basis of extensive spectroscopic methods, including 1D and 2D NMR techniques, and methyl ganosinensate A was confirmed by X-ray crystallographic analysis.

Unusual prenylated phenols with antioxidant activities from Ganoderma cochlear.

Seven new prenylated phenols, five novel phenols (1-5) with polycyclic skeleton and two new phenols (6 and 7) with a carbon chain, along with one known compound (8) were isolated from the fruiting bodies of Ganoderma cochlear. The structures of new compounds were elucidated by the spectroscopic technologies, X-ray crystallography analysis and chiral HPLC chromatography. All compounds showed antioxidant effect in radical scavenging assays and a plausible biosynthetic pathway for 1-8 was proposed.

Four New Polycyclic Meroterpenoids from Ganoderma cochlear

Four pairs of new polycyclic-meroterpenoid enantiomers, ganocins A-C (1-3) possessing a spiro[4,5]decane ring system, along with ganocin D (4) with an eight-membered ring, were isolated from the fruiting bodies of Ganoderma cochlear. Their structures were determined by spectroscopic data and X-ray diffraction crystallography. Their anti-AChE activities were evaluated, and a possible biogenetic pathway was also proposed.