4575-74-0Relevant academic research and scientific papers
Cycloarta-16,24-dien-3β-ol: Revised structure of cimicifugenol, a cycloartane triterpenoid
Akihisa, Toshihiro,Hideshima, Ryuichi,Koike, Kazuo
, p. 1157 - 1160 (1999)
The structure of a triterpene alcohol isolated from the nonsaponifiable lipids of both the root and aerial part extracts of Cimicifuga simplex (Ranunculaceae) was established to be cycloarta-16,24-dien-3β-ol (1). Spectral identity of the 24,25-dihydro derivative (4) of 1 with 24,25- dihydrocimicifugenol demonstrated that cimicifugenol, previously assigned the erroneous structure of cycloarta-7,24-dien-3β-ol, possesses structure 1.
Oxyfunctionalization of unactivated C-H bonds in triterpenoids with tert-butylhydroperoxide catalyzed by meso-5,10,15,20-tetramesitylporphyrinate osmium(II) carbonyl complex
Ogawa, Shoujiro,Wakatsuki, Yasuo,Makino, Mitsuko,Fujimoto, Yasuo,Yasukawa, Ken,Kikuchi, Takashi,Ukiya, Motohiko,Akihisa, Toshihiro,Iida, Takashi
experimental part, p. 165 - 171 (2010/06/19)
A system consisting of meso-5,10,15,20-tetramesitylporphyrinate osmium(II) carbonyl complex [Os(TMP)CO] as a precatalyst and tert-butylhydroperoxide (TBHP) as an oxygen donor is shown to be an efficient, regioselective oxidant system for the allylic oxidation, ketonization and hydroxylation of unactivated C-H bonds in a series of the peracetate derivatives of penta- and tetracyclic triterpenoids. Treatment of the substrates with this oxidant system afforded a variety of novel or scarce oxygenated derivatives in one-step. Structures of the isolated components, after chromatographic separation, were determined by spectroscopic methods including GC-MS and shift-correlated 2D-NMR techniques. Factors governing the regioselectivity and the possible mechanism for the oxyfunctionalization of the unactivated carbons are also discussed.
Cytotoxic triterpenoids from the leaves of Euphorbia pulcherrima
Smith-Kielland,Dornish,Malterud,Hvistendahl,R?mming,B?ckman,Kolsaker,Stenstr?m,Nordal
, p. 322 - 325 (2007/10/03)
Two cytotoxic triterpenes have been isolated from Euphorbia pulcherrima. Their structures and stereochemistry have been established from NMR, IR, and EI-mass spectroscopy. The compounds were identified as 9,19-cycloart-23-ene-3β,25-diol and 9,19-cycloart-25-ene-3β,24-diol. Cytotoxicity evaluation was performed using Ehrlich ascites tumor cells. While cycloartenol induced no cytotoxic activity against Ehrlich ascites tumor cells, both isolated triterpenes exhibited cell inactivating effects. The IC50 is approximately 7.5 μM, while the IC90 is approximately 13.5 μM for 9,19-cycloart-25-ene-3β,24-diol. The 3β,25-diol compound is 50% less active.
CYCLOROYLENOL, A CYCLOPROPANE CONTAINING EUPHOID FROM EUPHORBIA ROYLEANA
Vijaya, S. Bhat,Vimal, S. Joshi,Dwipin, D. Nanavati
, p. 5207 - 5210 (2007/10/02)
Cycloroylenol, a new tetracyclictriterpene in the latex of Euphorbia royleana Boiss is shown to have structure (1a)
