Cytotoxic Triterpenes and Sterol from the Fruit of Rabbiteye Blueberry (Vaccinium ashei)

Seven triterpenes, α-amyrin (1), uvaol (2), ursolic acid (3), β-amyrin (4), erythrodiol (5), lupeol (6) and betulin (7), two sterols, β-sitosterol (8) and β-sitosterol 3-O-β-glucopyranoside (9), and one flavonoid, syringetin 3-O-α-rhamnopyranoside (10) were isolated from the methanol extract of the fruit of rabbiteye blueberry (Vaccinium ashei). Their chemical structures were determined on the basis of spectroscopic data. Among them, 3, 4 and 9 exhibited moderate growth inhibitory activity against human lung cancer cells (PC-12) and human colon cancer cells (HCT116) using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay.

[1]  T. Nohara,et al.  Antioxidant ortho-benzoyloxyphenyl acetic acid ester, vaccihein A, from the fruit of rabbiteye blueberry (Vaccinium ashei). , 2002, Chemical & pharmaceutical bulletin.

[2]  H. Sakagami,et al.  Production of bioactive triterpenes by Eriobotrya japonica calli. , 2002, Phytochemistry.

[3]  Mingfu Wang,et al.  Antioxidative and cytotoxic components of highbush blueberry (Vaccinium corymbosum L.). , 1999 .

[4]  Li-zhen Xu,et al.  Flavonol glycosides from Lysimachia congestiflora , 1998 .

[5]  W. Kalt,et al.  Antioxidant capacity as influenced by total phenolic and anthocyanin content, maturity, and variety of Vaccinium species , 1998 .

[6]  Y. Noda,et al.  Enhanced cytotoxicity of some triterpenes toward leukemia L1210 cells cultured in low pH media: possibility of a new mode of cell killing. , 1997, Chemical & pharmaceutical bulletin.

[7]  K. Singletary,et al.  In vitro anticancer activity of fruit extracts from Vaccinium species. , 1996, Planta medica.

[8]  H. Ogura,et al.  Sterol glucosides from Prunella vulgaris , 1990 .

[9]  A. Numata,et al.  Cytotoxic triterpenes from a Chinese medicine, Goreishi. , 1989, Chemical & pharmaceutical bulletin.

[10]  A. McPhail,et al.  Cytotoxic components of Diospyros morrisiana , 1989 .

[11]  G. Cordell,et al.  3β-(3,4-Dihydroxycinnamoyl)-erythrodiol and 3β-(4-hydroxycinnamoyl)-erythrodiol from Larrea tridentata , 1988 .

[12]  H. Noguchi,et al.  Biosynthesis of sitosterol in tissue cultures of Rabdosia japonica hara and ergosterol in yeast from [2-13C,2-2H3]acetate , 1986 .

[13]  T. Mosmann Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. , 1983, Journal of immunological methods.

[14]  M. Katai,et al.  13C Nuclear Magnetic Resonance Spectra of Several Triterpenoids of Taraxerane and Ursane Series , 1983 .

[15]  M. Brattain,et al.  Heterogeneity of malignant cells from a human colonic carcinoma. , 1981, Cancer research.

[16]  R. Kasai,et al.  ^ C Nuclear Magnetic Resonance of Lupane-Type Triterpenes, Lupeol, Betulin and Betulinic Acid , 1980 .

[17]  K. Tanaka,et al.  Thromboplastic and fibrinolytic activities of cultured human cancer cell lines. , 1979, British Journal of Cancer.

[18]  J. Harborne,et al.  The leaf flavonoids of the Zingiberales. , 1977 .

[19]  Y. Tomita,et al.  Carbon-13 nmr spectra of urs-12-enes and application to structural assignments of components of tissue cultures , 1975 .