Cucurbitane-Type Triterpenoids from the Fruit of Momordica charantia

Abstract

The structures of three new cucurbitane-type triterpenoids isolated from the methanol extract of the fruit of Japanese Momordica charantia were established as (19R,23E)-5beta,19-epoxy-19-methoxycucurbita-6,23,25-trien-3beta-ol (1), (23E)-3beta-hydroxy-7beta-methoxycucurbita-5,23,25-trien-19-al (2), and (23E)-3beta-hydroxy-7beta,25-dimethoxycucurbita-5,23-dien-19-al (3) on the basis of spectroscopic methods. These compounds were accompanied by the known (19R,23E)-5beta,19-epoxy-19,25-dimethoxycucurbita-6,23-dien-3beta-ol (4) and (19R,23E)-5beta,19-epoxy-19-methoxycucurbita-6,23-diene-3beta,25-diol (5). This is the first report of the isolation of tetracyclic triterpenoids possessing a delta23,25-conjugated diene system, viz., 1 and 2, from a natural source.

Sterols from the Stems of Momordica charantia

“…The combined EtOAc soluble layer was subjected to repeated silica gel column chromatography and further purification by semi-preparative HPLC to yield compounds 1-9. The eight known compounds (2)(3)(4)(5)(6)(7)(8)(9) were identified by comparing their physical and spectral data with the reported values. The structure of the new sterol (1) was elucidated as follows.…”

“…Previous pharmacological studies have showed that the extracts or compounds of tissues of M. charantia possess anti-diabetic and anti-inflammatory activities. [1][2][3] Chemical investigations of M. charantia also revealed that more than seventy cucurbitane-type triterpenes have been isolated form the fruits, [3][4][5][6][7][8][9][10][11][12] seeds, 13,14 root, 15 and leaves and vines 16,17 of M. charantia. As part of our program aimed at the discovery of bioactive secondary metabolites from Taiwanese M. charantia, we had reported the isolation and structure elucidation of twenty-five cucurbitane-type triterpenoids from the MeOH extract of the stems of this plant.…”

Kuguacin J, a Triterpenoid from Momordica charantia Linn: A Comprehensive Review of Anticarcinogenic Properties

“…The cucurbitane-type triterpenoids and their aglycones have shown some biological effects beneficial in treating diabetes and obesity, and possess anticancer, anti-HIV and antifeedant properties [7,39]. More than fifty cucurbitacins and cucurbitane glycosides from the fruits, seeds, leaves, vines and stems have been reported [40][41][42][43][44][45][46][47][48]. Recently, Chen et al (2008) isolated and structured elucidation of nineteen cucurbitacins named kuguacins A-E from the roots of MC [49] and kuguacins F-S [50] from the vines and leaves of MC.…”

Synthesis of liposomes using -phosphotidycholine and metabolites obtained from Elephantorrhiza elephantina and Pentanisia prunelloides

“…Recently, much phytochemical-research attention has focused on the metabolites and pharmacokinetics of saponins due to their biological activities and absorption profile (Akihisa et al, 2007;Donya et al, 2007;Harinantenaina et al, 2006;Kimura et al, 2005). Saponins are responsible for diverse effects including anti-inflammation, anti-allergy, antitumor, augmentation of the immune responses, stimulating the apoptosis of skin cells, anti-obesity and anti-hyperlipidemia (Awad et al, 2011;Amin et al, 2010;Wang et al, 2011).…”