Kaguacidine A: a novel spirohydantoin-containing cucurbitane glycoside from vines of Momordica charantia L.

Abstract

The spirohydantoin-containing cucurbitane-type triterpenoid, kaguacidine A (1), was isolated and purified from 95% ethanol extracts of vines of Momordica charantia L (Cucurbitaceae). Its unprecedented chemical structure, a spirohydantoin substituent at C-23 of cucurbitane, was elucidated by extensive spectroscopic analyses, including HRESIMS, IR, optical rotation, 1D-and 2D-NMR spectra. The possible biosynthetic pathway is deduced and may be attributed to the metabolic activity of microbial symbionts in M. charantia L. Compound 1 was evaluated for anti-inflammatory activity against LPS-induced NO production in RAW 264.7 cells and anti-proliferative activity against four cancer cell lines, including HEp-2, MCF-7, Hep-G2, and WiDr. Compound 1 showed moderate anti-inflammatory activity with an IC50 value of 18.5 ± 0.4 μg/mL and weak anti-proliferative activity against MCF-7, HEp-2, Hep-G2, and WiDr with IC50 values of >40,