Cytotoxic activities and anti-tumor-promoting effects of microbial transformation products of prenylated chalcones from Angelica keiskei

Chemistry & Biodiversity
Toshihiro AkihisaYumiko Kimura

Abstract

Three prenylated chalcones, 4-hydroxyderricin (1), xanthoangelol (2), and xanthoangelol F (3), isolated from Angelica keiskei, were transformed by the fungus Aspergillus saitoi. These chalcones were converted to flavanones (i.e., 4, 8, and 12), and prenyl-chain-hydrated (i.e., 5, 7, 9-11, and 13) and ring-B-hydroxylated (i.e., 6) chalcones. The structures of three new metabolites, 7, 9, and 13, were established as 2″,3″-dihydro-4,3″-dihydroxyderricin, 6″,7″-dihydro-7″-hydroxyxanthoangelol, and 6″,7″-dihydro-7″-hydroxyxanthoangelol F, respectively. Upon evaluation of cytotoxic activities of compounds 1-13, the metabolite 7 exhibited potent cytotoxicity against HL60 cells, and this cell death was revealed to be mostly due to apoptosis. In addition, compounds 1-4, 7-10, 12, and 13 were examined for their inhibitory effects on the induction of Epstein-Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells. All compounds tested showed inhibitory effects against EBV-EA activation with potencies higher than that of β-carotene. Furthermore, the metabolite 13 exhibited inhibitory effect on skin tumor promotion in an in vivo two-stage mouse skin carcinogenesis test based on 7,12-dimethylbenz[a]anthr...Continue Reading

References

May 29, 2003·Current Pharmaceutical Biotechnology·R K Venisetty, V Ciddi
Mar 9, 2004·Phytochemistry·Aslieh NookandehHans Becker
Apr 24, 2004·Journal of Natural Products·M Sanchez-Gonzalez, J P N Rosazza
Dec 29, 2004·Journal of Natural Products·Lucas R ChadwickGuido F Pauli
Aug 5, 2005·Biological & Pharmaceutical Bulletin·Keiichi TabataTakashi Suzuki
Jan 31, 2006·Journal of Natural Products·Toshihiro AkihisaHoyoku Nishino
Mar 28, 2006·Journal of Natural Products·Shuvendu Das, John P N Rosazza
Apr 29, 2006·Journal of Natural Products·Toshihiro AkihisaYumiko Kimura
May 9, 2006·Biochimica Et Biophysica Acta·Vladimir GogvadzeBoris Zhivotovsky
May 17, 2007·Journal of Natural Products·Takashi KikuchiHoyoku Nishino
Jun 23, 2007·Journal of Agricultural and Food Chemistry·Tatsuji EnokiIkunoshin Kato
Aug 23, 2007·Journal of Agricultural and Food Chemistry·Shigenori KumazawaTsutomu Nakayama
Apr 23, 2010·Chemical & Pharmaceutical Bulletin·Takashi KikuchiToshihiro Akihisa
May 21, 2010·Journal of Oleo Science·Toshihiro AkihisaJiradej Manosroi

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Citations

Dec 3, 2014·Biotechnology Advances·Hui CaoJianbo Xiao
Oct 21, 2016·Chemistry & Biodiversity·Jie ZhangToshihiro Akihisa

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