Cytotoxic activities and anti-tumor-promoting effects of microbial transformation products of prenylated chalcones from Angelica keiskei.
Chem Biodivers
; 9(2): 318-30, 2012 Feb.
Article
em En
| MEDLINE
| ID: mdl-22344908
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 2â³,3â³-dihydro-4,3â³-dihydroxyderricin, 6â³,7â³-dihydro-7â³-hydroxyxanthoangelol, and 6â³,7â³-dihydro-7â³-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 ß-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]anthracene (DMBA) as initiator, and with TPA as promoter.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Neoplasias Cutâneas
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Transformação Celular Neoplásica
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Apoptose
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Angelica
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Chalconas
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Antineoplásicos Fitogênicos
Limite:
Animals
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Humans
Idioma:
En
Revista:
Chem Biodivers
Assunto da revista:
BIOQUIMICA
/
QUIMICA
Ano de publicação:
2012
Tipo de documento:
Article
País de afiliação:
Japão