3-epicabraleahydroxylactone and other triterpenoids from camellia oil and their inhibitory effects on Epstein-Barr virus activation.

The structure of a triterpenoid isolated from the nonsaponifiable lipid (NSL) of the seed oil of the camellia (Camellia japonica L.; Theaceae) was established to be (20S)-3beta-hydroxy-25,26,27-trisnordammaran-24,20-olide (1; 3-epicabraleahydroxylactone) on the basis of spectroscopic and chemical methods. Six other triterpenoids isolated from the NSL were identified as 3-epicabraleadiol (2), ocotillol II (3), ocotillol I (4), dammarenediol II (5), (20R)-taraxastane-3beta,20-diol (6), and lupane-3beta,20-diol (7). Upon evaluation of the seven triterpenoids (1-7) with respect to their inhibitory effects on the induction of Epstein-Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, three compounds (5-7) showed potent inhibitory effects against EBV-EA induction (IC(50) values of 277-420 mol ratio/32 pmol TPA).

[1]  K. Koike,et al.  Constituents of compositae plants. 2. Triterpene diols, triols, and their 3-o-fatty acid esters from edible chrysanthemum flower extract and their anti-inflammatory effects. , 2001, Journal of agricultural and food chemistry.

[2]  T. Akihisa,et al.  Antitumor-promoting and anti-inflammatory activities of triterpenoids and sterols from plants and fungi , 2001 .

[3]  K. Koike,et al.  Acyclic and incompletely cyclized triterpene alcohols in the seed oils of theaceae and Gramineae , 1999, Lipids.

[4]  K. N. Rao,et al.  Triterpenoids from Mangifera indicafn1fn1Part iii in the series Triterpenoids from Mangifera indica. For part ii see Anjaneyulu et al., 1989. , 1999 .

[5]  Akihisa,et al.  Camelliols A-C, three novel incompletely cyclized triterpene alcohols from sasanqua oil (Camellia sasanqua) , 1999, Journal of natural products.

[6]  T. Akihisa,et al.  Sasanquol, a 3,4-seco-triterpene alcohol from sasanqua oil, and its anti-inflammatory effect. , 1998, Phytochemistry.

[7]  Akihisa,et al.  Isohelianol: A 3,4-seco-Triterpene Alcohol from Sasanqua Oil , 1998, Journal of natural products.

[8]  T. Akihisa,et al.  Triterpene alcohols from camellia and sasanqua oils and their anti-inflammatory effects. , 1997, Chemical & pharmaceutical bulletin.

[9]  H. Itokawa,et al.  Cytotoxic triterpenes from Cleome africana. , 1997, Phytochemistry.

[10]  T. Satoh,et al.  Chemical Evaluation of Betula Species in Japan. II. Constituents of Betula platyphylla var. japonica , 1996 .

[11]  A. Murakami,et al.  Anti-tumor promotion with food phytochemicals: a strategy for cancer chemoprevention. , 1996, Bioscience, biotechnology, and biochemistry.

[12]  H. Wagner,et al.  Triterpenoids from the aerial parts of Salvia montbretii , 1994 .

[13]  H. Nishino,et al.  Inhibitory effects of dihydroagarofuran sesquiterpenes on Epstein-Barr virus activation. , 1992, Cancer letters.

[14]  T. Nikaido,et al.  Constituents of Pollen. V. Constituents of Betula platyphylla var. japonica , 1978 .

[15]  R. Kasai,et al.  13C NMR Study of ginseng sapogenins and their related dammarane type triterpenes , 1977 .

[16]  D. Lavie,et al.  Cabralea eichleriana dc. (meliaceae)—I structure and stereochemistry of wood extractives , 1975 .

[17]  K. Brown,et al.  Biogenetically significant triterpenes in a species of meliaceae: Cabralea polytricha A.Juss. , 1972 .

[18]  A. Bose,et al.  Terpenoids—LXXXVI : Structure of epi-ψ-taraxastanonol and epi-ψ-taraxastanediol☆ , 1966 .

[19]  E. Warnhoff,et al.  DESERT PLANT CONSTITUENTS: II. OCOTILLOL: AN INTERMEDIATE IN THE OXIDATION OF HYDROXY ISOÖCTENYL SIDE CHAINS , 1965 .