Kleinhospitine E and Cycloartane Triterpenoids from Kleinhovia hospita

Journal of Natural Products
Abdul RahimKyoko Nakagawa-Goto

Abstract

A novel cycloartane triterpenoid alkaloid, kleinhospitine E (1), six new cycloartane triterpenoids (2-7), three known cycloartane triterpenoids (8-10), and taraxerone (11) were isolated from a methanol extract of Kleinhovia hospita. Their structures were elucidated by 1D- and 2D-NMR spectroscopy as well as HRMS analysis. The absolute configurations of all isolated compounds were determined from their ECD spectra by comparison with theoretical values. Kleinhospitine E (1) is the first cycloartane alkaloid possessing an unusual γ-lactam with an oxopropylidene side chain. Compounds 2, 3, and 6 were assigned as cycloartane triterpenoids with a 9α,10α-cyclopropyl ring, which is found rarely among naturally occurring compounds, while 4 and 5 were established as isomers of compound 3 containing a 21,23-diacetal side chain. Biological evaluation revealed that compounds 4 and 9 exhibited more potent antiproliferative activities against a multidrug-resistant tumor cell line compared with its parent chemosensitive cell line. Furthermore, compound 6 exhibited submicromolar anti-HIV activity.

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Citations

Feb 6, 2019·Organic & Biomolecular Chemistry·Yong-Li LiXian-Wen Yang
Jul 16, 2020·Medicinal Research Reviews·Hai-Feng WuKuo-Hsiung Lee
Jun 9, 2021·Natural Product Research·Yi-Ting WangDuo-Zhi Chen

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