Microbial Transformation of Yakuchinone A and Cytotoxicity Evaluation of Its Metabolites.
Int J Mol Sci
; 23(7)2022 Apr 03.
Article
em En
| MEDLINE
| ID: mdl-35409351
ABSTRACT
Yakuchinone A (1) is a bioactive diarylheptanoid isolated from the dried fruits of Alpinia oxyphylla. Microbial transformation has been recognized as an efficient method to produce new biologically active derivatives from natural products. In the present study, microbial transformation of yakuchinone A was performed with the fungus Mucor hiemalis KCTC 26779, which led to the isolation of nine new metabolites (2, 3a, 3b, and 4-9). Their structures were elucidated as (3S)-oxyphyllacinol (2), (3S,7R)- and (3S,7S)-7-hydroxyoxyphyllacinol (3a and 3b), (3S)-oxyphyllacinol-4'-O-ß-d-glucopyranoside (4), (3S)-4â³-hydroxyoxyphyllacinol (5), (3S)-3â³-hydroxyoxyphyllacinol (6), (3S)-2â³-hydroxyoxyphyllacinol (7), (3S)-2â³-hydroxyoxyphyllacinol-2â³-O-ß-d-glucopyranoside (8), and (3S)-oxyphyllacinol-3-O-ß-d-glucopyranoside (9) based on the comprehensive spectroscopic analyses and the application of modified Mosher's method. All compounds were evaluated for their cytotoxic activities against melanoma, as well as breast, lung, and colorectal cancer cell lines. Compound 9, which was O-glucosylated on the diarylheptanoid alkyl chain, exhibited the most selective cytotoxic activities against melanoma cell lines with the IC50 values ranging from 6.09 to 9.74 µM, indicating that it might be considered as a possible anti-cancer lead compound.
Palavras-chave
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Alpinia
/
Melanoma
Limite:
Humans
Idioma:
En
Revista:
Int J Mol Sci
Ano de publicação:
2022
Tipo de documento:
Article