Yin-Di Zhu

Antimalarial and Antiproliferative Cassane Diterpenes of Caesalpinia sappan.

Bioassay-guided fractionation of a methanol extract of the seeds of Caesalpinia sappan led to the isolation of 12 new cassane-type diterpenes, caesalsappanins A-L (1-12). Their structures were elucidated on the basis of NMR and HRESIMS analysis, and the absolute configuration of compound 1 was determined by single-crystal X-ray crystallography. All isolated compounds were tested against a chloroquine-resistant Plasmodium falciparum strain for antiplasmodial activities and against a small panel of human cancer cell lines for antiproliferative activities. Compounds 7 and 8 displayed antimalarial activity against the chloroquine-resistant K1 strain of P. falciparum with IC50 values of 0.78 and 0.52 μM and selectivity indices of 17.6 and 16.4, respectively. Compound 10 showed antiproliferative activity against the KB cancer cell line with an IC50 value of 7.4 μM.

Two new abietane diterpenoid glycosides from Clinopodium chinense

Abstract Two new abietane diterpenoid glycosides, named clinopoditerpenes B (1) and C (2), were isolated from Clinopodium chinese. The structures of the new compounds were determined on the basis of extensive spectral analysis. Compound 1 exhibited cardioprotective effect against H2O2-induced apoptosis in H9c2 cells.

Norcassane- and cassane-type furanoditerpenoids from the seeds of Caesalpinia sappan

Three novel furanoditerpenoids, norcaesalpinin J (1) featuring an unusual 20-norcassane hydroperoxide and phangininoxys B (2) and C (3) possessing cassane hemiketal skeletons, were isolated from the seeds of Caesalpinia sappan. Their structures were elucidated by extensive spectroscopic methods. All isolates were evaluated for the cytotoxic activities on three human cancer cell lines.

Four new phenolic acid with unusual bicycle [2.2.2] octane moiety from Clerodendranthus spicatus and their anti-inflammatory activity

Four new phenolic acids, clerodens A-D (1-4) possessing an unusual bicycle [2.2.2] octane moiety were isolated from the whole plants of Clerodendranthus spicatus. Their structures were elucidated by extensive spectroscopic methods, including NMR, MS, and ECD data. All isolates were evaluated for their anti-inflammatory activities on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW 264.7, and compound 4 showed significant inhibitory activities with IC50 value of 6.8 μM.

Study of ATP-binding Cassette Transporter A1 (ABCA1)-mediated Cellular Cholesterol Efflux in Diabetic Golden Hamsters

The effects of cyclic adenosine monophosphate (cAMP) and atorvastatin on macrophage adenosine triphosphate (ATP)-binding cassette transporter A1 (ABCA1)-mediated cholesterol efflux were investigated in a diabetic animal model. Golden hamsters were fed a high-fat diet which resulted in insulin resistance. Diabetes was induced by a single intraperitoneal injection of streptozotocin (30 mg/kg). Normal golden hamsters were used as controls. Peritoneal macrophages were incubated with apolipoprotein A-1 (apoA-1), 8-bromoadenosine-3′,5′-cyclic monophosphate (8-br-cAMP), and atorvastatin in vitro Intracellular cholesterol accumulation was greater in the diabetic animals than in the insulin-resistant animals. Expression of ABCA1 mRNA in macrophages from diabetic animals was upregulated by 8-br-cAMP and atorvastatin. ApoA-1 caused a time-dependent cellular cholesterol efflux. Both atorvastatin and 8-br-cAMP significantly facilitated ABCA1-mediated cellular cholesterol efflux, with the maximal cholesterol efflux rate observed in the macrophages from diabetic animals. Accumulation of cholesterol in the macrophages of diabetic animals can be significantly alleviated by atorvastatin or 8-br-cAMP through improving ABCA1-mediated cellular cholesterol efflux.

Clinoposides A–F: meroterpenoids with protective effects on H9c2 cardiomyocyte from Clinopodium chinense

Six novel flavonoid–triterpene saponin meroterpenoids, clinoposides A–F (1–6), with two unusual skeletons were isolated from Clinopodium chinense. Clinoposides A–F represent a new class of isopentenyl flavonoid saponin. Their structures were determined based on spectroscopic data and chemical methods. The relative and absolute stereochemistries were assigned using a combination of NOESY and ECD. A possible biogenetic pathway for 1–6 is proposed. The protective effects of clinoposides A–F against H2O2-induced H9c2 cardiomyocyte injury were tested, and all compounds exhibited significantly dose-dependent effects, clinoposides B, D and F showed better protective effects as evidence by increased levels of SOD, CAT and GSH-Px but reduced MDA, LDH, caspase-3 and -9 levels.

A new phenylethanoid glycoside from Incarvillea compacta

Abstract A new phenylethanoid glycoside, 3′′′-O-methylcampneoside I (1), was isolated from the 90% ethanolic extract of the roots of Incarvillea compacta, together with three known compounds, campneoside I (2), ilicifolioside A (3), and campneoside II (4). Their structures were determined spectroscopically and compared with previously reported spectral data. Compound 1 existed as epimers and displayed better 1,1-diphenyl-2-picrylhydrazyl (DPPH)-free radical scavenging activity using di-tert-butyl-4-methylphenol (BHT) as the positive control. In addition, pretreatment of human HepG2 cells with compound 1 significantly increased the viability on CCl4-induced cell death.

Two new flavonoid–triterpene saponin meroterpenoids from Clinopodium chinense and their protective effects against anoxia/reoxygenation-induced apoptosis in H9c2 cells

Two new flavonoid-triterpene saponin meroterpenoids, clinoposides G (1) and H (2) were isolated from the aerial parts of Clinopodium chinense (Benth.) O. Kuntze. Their structures were elucidated through spectroscopic and electronic circular dichroism (ECD) analyses. Compounds 1 and 2 were evaluated for their protective effects against anoxia/reoxygenation(A/R)-induced injury in H9c2 cells. A/R treatment severely injured the H9c2 cells, which was accompanied by apoptosis. Both 1 and 2 pretreatment significantly inhibited cell injury and apoptosis, improved mitochondrial membrane potential, increased activities of antioxidant enzymes, and reduced the levels of the inflammatory cytokines. In addition, the presence of 1 and 2 significantly decreased the protein level of p65 and increased the level of Nrf2 in cell nucleus. Unique chemical structure and good biological activity of 1 and 2 elucidated the potential of meroterpenoids as a promising reagent for treating heart disease.

Oleanane triterpene saponins with cardioprotective activity from Clinopodium polycephalum

Abstract Two new triterpene saponins, clinopodiside VI (1) and saikosaponin c (2), along with six known saikosaponins (3–8), were isolated from the plant of Clinopodium polycephalum. Compounds 1–3 showed moderate inhibition against H9c2 cell damage induced by H2O2.

Structure elucidation of a new cycloartane triterpene glycoside from Souliea vaginata by NMR

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