A new noroleanane named as karounitriol (1), together with four known compounds, 7-oxodihydrokarounidiol (2), isokarounidiol (3), karounidiol (4), and stigmasta-7,22-dien-3β-ol were isolated from the seeds of Trichosanthes kirilowii Maxim. Structure of the new compound was elucidated as 3α,7β,29-trihydroxy-D:C-friedo-olean-8-ene on the basis of spectroscopic methods including extensive 1D NMR (1H, 13C), 2D NMR (1H-1H COSY, DEPT, HMQC, HMBC, and NOESY), IR, and MS studies.
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(a) YasukawaK., AkihisaT., TamuraT., TakidoM. (1994) Inhibitory effect of karounidiol on 12-O-tetradecanoylphorbol-13-acetate-induced tumor promotion. Biological & Pharmaceutical Bulletin, 17, 460–462; (b) Akihisa T, Yasukawa K, Kimura Y, Takido M, Kokke WC, Tamura T. (1994) Five D:C-friedo-oleanane triterpenes from the seeds of Trichosanthes kirilowii Maxim. and their anti-inflammatory effects. Chemical & Pharmaceutical Bulletin, 42, 1101-1105.
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ChaoZ.M., TangC.F., ZhangG.F., SunW. (2012) TLC identification and HPLC assay on trichosanthis semen. Chinese Journal of Experimental Traditional Medical Formulae, 18, 86–88.
13.
(a) AkihisaT., KokkeW.C., TamuraT., NambaraT. (1992) 7-Oxodihydrokarounidiol [7-oxo-D:C-friedo-olean-8-ene-3α,29-diol], a novel triterpene from Trichosanthes kirilowi.Chemical & Pharmaceutical Bulletin, 40, 1199–1202. (b) Chao ZM, Shibusawa Y, Yanagida A, Shimotakahara S, Shindo H. (2005) Two new triterpenes from the seeds of Trichosanthes cucumeroides. Natural Product Research, 19, 211-216.
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AkihisaT., KokkeW.C., KimuraY., TamuraT. (1993) Isokarounidiol [D:C-friedooleana-6,8-diene-3α,29-diol]: the first naturally occurring triterpene with a Δ68-conjugated diene system. Iodine-mediated dehydrogenation and isomerization of its diacetateJournal of Organic Chemistry, 58, 1959–1962.
17.
AkihisaT., TamuraT., MatsumotoT. (1988) Karounidiol [D:C-friedo-oleana-7,9(11)-diene-3α,29-diol] and its 3-O-benzoate: novel pentacyclic triterpenes from Trichosanthes kirilowii. X-ray molecular structure of karounidiol diacetate. Journal of the Chemical Society Perkin Transactions, 3, 439–443.
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