title: The antigluconeogenic activity of cucurbitacins from Momordica charantia.
abstract: Five new cucurbitacins, kuguacins II-VI (1-5), along with five known analogues (6-10), were obtained from the fruit of Momordica charantia. Structures of the new compounds were elucidated as 5β,19-epoxycucurbit-23-en-7-on-3β,25-diol (1), 5β,19-epoxycucurbit-7,23-dion-3β,25-diol (2), 5β,19-epoxycucurbit-6-en-19,23-dion-3β,25-diol (3), 5β,19-epoxy-23,24,25,26,27-pentanorcucurbit-6-en-7,19-dion-3β,22-diol (4), and cucurbit-5-en-7,23-dion-3β,19,25-triol (5) by extensive spectroscopic and single-crystal X-ray diffraction analyses. Some cucurbitane compounds from this species were screened for their potential antidiabetic properties in terms of antigluconeogenic activity. As a result, compounds 1, 10, 11, and 12 (at 25-100 µM) showed concentration-dependent inhibition on glucose production from liver cells. In addition, compounds 11 and 12 (at 100 µM) showed around 20-30 % inhibition on PEPCK activity.
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Yunnan, P. R. China.
authors.forename: Jian-Chao
authors.initials: JC
authors.lastname: Chen
authors.affiliation: Institute of Chinese Medicine, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, P. R. China.
authors.forename: Clara Bik-San
authors.initials: CB
authors.lastname: Lau
authors.affiliation: Institute of Chinese Medicine, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, P. R. China.
authors.forename: Judy Yuet-Wa
authors.initials: JY
authors.lastname: Chan
authors.affiliation: Institute of Chinese Medicine, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, P. R. China.
authors.forename: Kwok-Pui
authors.initials: KP
authors.lastname: Fung
authors.affiliation: Institute of Chinese Medicine, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, P. R. China.
authors.forename: Ping-Chung
authors.initials: PC
authors.lastname: Leung
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Yunnan, P. R. China.
authors.forename: Jie-Qing
authors.initials: JQ
authors.lastname: Liu
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Yunnan, P. R. China.
authors.forename: Lin
authors.initials: L
authors.lastname: Zhou
authors.affiliation: School of Chemical Science and Technology, Yunnan University, Kunming, P. R. China.
authors.forename: Ming-Jin
authors.initials: MJ
authors.lastname: Xie
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Yunnan, P. R. China.
authors.forename: Ming-Hua
authors.initials: MH
authors.lastname: Qiu
mesh_terms: D054728:Cucurbitacins / Q000302:isolation & purification / Q000494:pharmacology*; D005638:Fruit / Q000737:chemistry; D005943:Gluconeogenesis / Q000187:drug effects*; D005947:Glucose / Q000378:metabolism*; D006027:Glycosides / Q000302:isolation & purification / Q000494:pharmacology; D007004:Hypoglycemic Agents / Q000302:isolation & purification / Q000494:pharmacology*; D008099:Liver / Q000187:drug effects* / Q000378:metabolism; D015394:Molecular Structure; D029777:Momordica charantia / Q000737:chemistry*; D019764:Phosphoenolpyruvate Carboxykinase (ATP) / Q000378:metabolism; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D014315:Triterpenes / Q000302:isolation & purification / Q000494:pharmacology; D014961:X-Ray Diffraction
chemical_list: D006027:Glycosides; D007004:Hypoglycemic Agents; D010936:Plant Extracts; D014315:Triterpenes; C514277:cucurbitane; D054728:Cucurbitacins; C000597251:PCK2 protein, human; D019764:Phosphoenolpyruvate Carboxykinase (ATP); D005947:Glucose