39765-50-9Relevant academic research and scientific papers
Conformation of Bryonolic Acid and Its Derivatives in CDCl3 Solution by 1H NMR and 13C NMR Spectroscopy
Kamisako, Wasuke,Suwa, Kiyoko,Honda, Chie,Isoi, Koichiro,Nakai, Hiroshi,et al.
, p. 848 - 855 (1987)
Comparison of the 1H and 13C chemical shift data of bryonolic acid (D:C-friedoolean-8-en-3β-ol-29-oic acid) and its derivatives (13 species) revealed that the conformational features of these compounds in CDCl3 solution depend on whether the functional groups at C-29 are trigonal, such as COOCH3, or tetrahedral, such as CH2OH.In order to study the conformational features of these two groups of compounds, vicinal coupling constants between the protons on the E rings of the methyl ester of D:C-friedoolean-8-en-29-oic acid, D:C-fridoolean-8-en-29-ol and its acetate were measured.Comparison of the results with the steric geometries to be expected from the molecular mechanics calculation for the E-ring moieties of these derivatives in the S form (D-E rings: boat-boat form) and the F form (D-E rings: chair-chair form) led to the conclusion that the compounds having a trigonal functional group at C-29 mainly adopt the S form, and those having a tetrahedral functional group at C-29 are present as mixtures of the S and F form in equilibrium in the solutions.KEY WORDS - Conformation D:C-friedoolean-8-enes Molecular mechanics calculation 1H and 13C NMR
Five D:C-friedo-oleanane triterpenes from the seeds of Trichosanthes kirilowii MAXIM. and their anti-inflammatory effects
Akihisa,Yasukawa,Kimura,Takido,Kokke,Tamura
, p. 1101 - 1105 (2007/10/02)
Five triterpenes with a D:C-friedo-oleanane skeleton, D:C-friedo-oleana- 7,9(11)-diene-3β,29-diol (3-epikarounidiol), 7-oxo-D:C-friedo-olean-8-en- 3β-ol (7-oxoisomultiflorenol), 7-oxo-8β-D:C-friedo-olean-9(11)-ene-3α,29- diol, D:C-friedo-olean-8-ene-3α,29-diol (3-epibryonolol), and D:C-friedo- olean-8-ene-3β,29-diol (bryonolol), the first four of which are new naturally occurring compounds, were isolated from the seeds of Trichosanthes kirilowii MAXIM. The structures were determined by spectral and chemical methods. 3-Epikarounidiol, 7-oxoisomultiflorenol, and 3-epibryonolol showed marked inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced ear inflammation in mice. The 50% inhibitory dose of these triterpenes for TPA-induced inflammation (1 μg) was 0.2-0.6 mg/ear.
BIOSYNTHESIS OF BRYONOLIC ACID IN CULTURED CELLS OF WATERMELON
Cho, Hi Jae,Ito, Michiho,Tanaka, Shigeo,Kamisako, Wasuke,Tabata, Mamoru
, p. 1407 - 1414 (2007/10/02)
Bryonolic acid, a pentacyclic triterpene having an anti-allergic activity, was biosynthesized from R-mevalonate or acetate administered to cell cultures of watermelon (citrullus lanatus).The radioactivity of the labelled mevalonate added to cell-free extracts in the presence of ATP, Mg2+ adn NADPH was also incorporated into bryonolic acid as well as into the possible intermediates, isomultiflorenol, bryonolol and bryonolal.Furthermore, 2,2-oxidosqualene added to the microsomal solution of the same cell-free extracts was converted enzymatically into isomultiflorenol, which is converted to be the first cyclization product in the biosynthesis of bryonolic acid.These results indicate that bryonolic acid is biosynthesized from 2,3-oxidosqualene via isomultiflorenol and subsequent oxidations of the methyl group at C-29.
7-Oxodihydrokarounidiol [7-oxo-D:C-friedo-olean-8-ene-3α,29-diol], novel triterpene from Trichosanthes kirilowii
Akihisa,Kokke,Tamura,Nambara
, p. 1199 - 1202 (2007/10/02)
The structure of 7-oxodihydrokarounidiol [7-oxo-D:C-friedo-olean-8-ene-3α,29-diol], isolated from the seeds of Trichosanthes kirilowii (Cucurbitaceae), was determined by chemical correlation with karounidiol [D:C-friedo-oleana-7,9(11)-diene-3α,29-diol] from the same source. Two other natural products, viz. bryonolic acid (3β-hydroxy-D:C-friedo-olean-8-en-29-oic acid) and bryononic acid (3-oxo-D:C-friedo-olean-8-en-29-oic acid), were also correlated with karounidiol.
