Ichthyotoxic and anticarcinogenic effects of triterpenoids from Sandoricum koetjape bark.

After bioassay-guided fractionation of the extract from Sandoricum koetjape bark, which exhibited significant toxicity to killifish (Oryzias latipes), two ichthyotoxic triterpenoids were isolated and characterized as koetjapic acid and 3-oxo-olean-12-en-29-oic acid. These constituents, along with non-toxic katonic acid, had a remarkable inhibitory effect on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol 13-acetate (TPA), which is a preliminary in vitro screening method for possible anti-tumor-promoting agents. Of the triterpenoids active in vitro, koetjapic acid appears to be a promising cancer chemopreventive agent, since it significantly delayed tumor promotion in two-stage mouse skin carcinogenesis induced by 7,12-dimethylbenz(a)anthracene and promoted by TPA.

[1]  Hiroyuki Suzuki,et al.  Constituents of Compositae plants III. Anti-tumor promoting effects and cytotoxic activity against human cancer cell lines of triterpene diols and triols from edible chrysanthemum flowers. , 2002, Cancer letters.

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

[3]  T. Konoshima,et al.  Cancer-chemopreventive effects of natural sweeteners and related compounds , 2002 .

[4]  H. Nishino,et al.  Anti-tumor promoting effects of multiflorane-type triterpenoids and cytotoxic activity of karounidiol against human cancer cell lines. , 2001, Cancer letters.

[5]  A. Yoshitake,et al.  Cancer chemopreventive agents, serratane-type triterpenoids from Picea jezoensis. , 2001, Cancer letters.

[6]  M. Hayashi,et al.  New multiflorane-type triterpenoid acids from Sandoricum indicum. , 2001, Journal of natural products.

[7]  T. Yoshida,et al.  Ichthyotoxic phloroglucinol derivatives from Dryopteris fragrans and their anti-tumor promoting activity. , 2000, Chemical & pharmaceutical bulletin.

[8]  S. R. Starck,et al.  DNA Polymerase Inhibitors from Sandoricum k oetjape , 1999 .

[9]  Hideyuki Ito,et al.  Identification of iridals as piscicidal components of Iridaceous plants and their conformations associated with CD spectra , 1997 .

[10]  T. Konoshima,et al.  Anti-tumor-promoting activities of triterpenoids from ferns. I. , 1996, Biological & pharmaceutical bulletin.

[11]  Y. Asakawa,et al.  Secomultiflorane-type triterpenoid acids from stem bark of Sandoricum koetjape , 1995 .

[12]  J. Pezzuto,et al.  Plant anticancer agents, L. cytotoxic triterpenes from Sandoricum koetjape stems. , 1992, Journal of natural products.

[13]  T. Konoshima,et al.  Inhibition of 12-O-tetradecanoylphorbol-13-acetate-promoted mouse skin papilloma by saponins. , 1991, Oncology.

[14]  J. Clardy,et al.  Limonoid antifeedants from seed of Sandoricum koetjape. , 1991, Journal of natural products.

[15]  T. Sugimura,et al.  Antitumor promoting activity of (−)‐epigallocatechin gallate, the main constituent of “Tannin” in green tea , 1987 .

[16]  Y. Ito,et al.  Epstein-Barr virus activation by tung oil, extracts of Aleurites fordii and its diterpene ester 12-O-hexadecanoyl-16-hydroxyphorbol-13-acetate. , 1983, Cancer letters.

[17]  L. M. Perry,et al.  Medicinal Plants of East and Southeast Asia: Attributed Properties and Uses , 1980 .

[18]  T. Okuda,et al.  Studies on the Constituents of Buddleja Species. I. Structures of Buddledin A and B, Two New Toxic Sesquiterpenes from Buddleja davidii FRANCH. , 1978 .

[19]  S. Soloway Naturally occurring insecticides. , 1976, Environmental health perspectives.

[20]  D. Crosby,et al.  Naturally Occurring Insecticides , 1972 .

[21]  B. A. Westfall,et al.  Antitumor activity of Juglans niga (black walnut) extractives. , 1968, Journal of pharmaceutical sciences.

[22]  W. Henle,et al.  Immunofluorescence in Cells Derived from Burkitt's Lymphoma , 1966, Journal of bacteriology.