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Seven new cucurbitane-type triterpenoids, kuguaovins A–G (1–7), and five known ones were isolated from the rattans of wild Momordica charantia. Their structures were established by spectroscopic da...

Trapa natans L., called water chestnut or water caltrop, is a floating aquarium plant. Its fruits are widely used as food. Two new tannins, 1 and 2, one new neolignan, 14, one new norlignan, 17, and 20 known compounds, 3-13, 15, 16, and 18-24 were isolated from T. natans pericarps in this study. The 1, 2, 14, and 17 structures were elucidated using a chemical method and extensive spectral evidence. A series of hydrolyzable tannins, 1-8, a lignin, 13, a flavonoid, 16, a norlignan, 17, and phenolic compounds, 18, 20, 21, and 24 resulted in the enhanced glucose uptake activity in C2C12 myotubes. Compounds 4 and 5 significantly increased GLUT4 protein expression in C2C12 myotubes. In addition, 4 and 5 improved the phosphorylation of AMPK, AKT(S473), and AKT(T308). The involvement of AMPK and PI3K in the mechanism of action of compounds 4 and 5 was confirmed by use of AMPK and PI3K inhibitors, which completely suppressed the 4- and 5-mediated activities of glucose uptake in C2C12 myotubes. We also demonstrated that 4 and 5 could increase GLUT4 protein levels in plasma membranes.

Glaulactams A–C (1–3), which possess a novel skeleton, as well as the known compound daphmanidin B (4), were isolated from the leaves of Daphniphyllum glaucescens and separated using ion-exchange chromatography aided by NMR fingerprinting. Their structures, including their absolute configurations, were elucidated by spectroscopic analyses and time-dependent density-functional-theory-calculated electronic circular dichroism spectra; the data were subsequently analyzed to gain insight into the respective biogenetic relationships between the isolates, which exhibited anti-H1N1 and immunosuppressive activities.

Five new 5β,19-epoxycucurbitane triterpenoids, taikugausins A-E (1-5), together with 5β,19-epoxy-25-methoxycucurbita-6,23-diene-3β,19-diol (6), have been isolated and characterized from the 70 % EtOH extract of the fresh fruits of Momordica charantia. The chemical structures of compounds 1-6 were elucidated on the basis of extensive spectroscopic analyses, especially 2D NMR (HMQC, HMBC, and NOESY) experiments and HRESIMS data. The relationship between NMR chemical shifts and the configuration of C-19 with an OMe group in 5β,19-epoxycucurbitane are described. Among them, compounds 3 and 4 exhibited remarkable anti-inflammatory activities by the inhibition of nitric oxide production at the concentration of 10 µg/mL. In addition, 3 and 4 also showed moderate cytotoxicity against WiDr, Hep G2, MCF-7, and HEp-2 human tumor cell lines.

Two new steroidal saponins, named drangustosides A–B (1–2), together with eight known compounds 3–10 were isolated and characterized from the MeOH extract of Dracaena angustifolia Roxb. The structures of compounds were assigned based on 1D and 2D NMR spectroscopic analyses, including HMQC, HMBC, and NOESY. Compounds 1 and 2 showed anti-inflammatory activity by superoxide generation and elastase release by human neutrophils in response to fMLP/CB.

This paper reports that bioassay-guided fractionations of EtOH extract of Momordica charantia fruits led to the isolation of 15 cucurbitane-type triterpene glycosides including 4 new compounds, kuguaosides A-D (1-4), along with 11 known ones, charantoside A (5), momordicosides I (6), F1 (7), F2 (8), K (9), L (10), and U (11), goyaglycosides-b (12) and -d (13), 7β,25-dihydroxycucurbita-5,23(E)-dien-19-al 3-O-β-d-allopyranoside (14), and 25-hydroxy-5β,19-epoxycucurbita-6,23-dien-19-on-3β-ol 3-O-β-d-glucopyranoside (15). Their structures were elucidated on the basis of spectroscopic analyses and chemical methods. This study also established the HPLC-ELSD fingerprinting profile of an antiproliferative fraction of which 11 main peaks were identified. Biological evaluation showed that several isolated cucurbitane-type triterpene glycosides had antiproliferative activities against MCF-7, WiDr, HEp-2, and Doay human tumor cell lines. In addition, compound 14 showed potent hypoglycemic activities by glucose uptake assay.

In an attempt to study the chemical constituents from the twigs and leaves of Flueggea virosa, a new terpenoid, 9(10→20)-abeo-ent-podocarpane, 3β,10α-dihydroxy-12-methoxy-13- methyl-9(10→20)-abeo-ent-podocarpa-6,8,11,13-tetraene (1), as well as five known compounds were characterized. Their structures were elucidated on the basis of spectroscopic analysis. In addition, the structure of dehydrochebulic acid trimethyl ester was revised as (2S,3R)-4E-dehydrochebulic acid trimethyl ester based on a single-crystal X-ray diffraction study. The in vitro anti-hepatitis C virus (anti-HCV) activity and cytotoxicity against Huh7.5 cells for the isolated compounds were evaluated.