Microbial Transformation of Yakuchinone A and Cytotoxicity Evaluation of Its Metabolites

• Published in: International journal of molecular sciences Vol. 23; no. 7; p. 3992
• Main Authors: Huo, Chen, Han, Fubo, Xiao, Yina, Kim, Hyun Jung, Lee, Ik-Soo
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 03-04-2022; MDPI
• Subjects: Alpinia - chemistry; Biocompatibility; Biological activity; Breast cancer; Carbon; Colorectal carcinoma; Cytotoxicity; Diarylheptanoids; Fruit; Glucose; Humans; Hydrocarbons; Lead compounds; Lung cancer; Melanoma; Metabolites; microbial transformation; Microorganisms; Molecular Structure; Mosher’s method; Natural products; Plant Extracts - chemistry; Transformations; Tumor cell lines; yakuchinone A; Mosher’s method; microbial transformation; yakuchinone A; cytotoxicity
• ISSN: 1422-0067; 1661-6596; 1422-0067
• DOI: 10.3390/ijms23073992

Yakuchinone A (
) is a bioactive diarylheptanoid isolated from the dried fruits of
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
KCTC 26779, which led to the isolation of nine new metabolites (
,
,
, and
-
). Their structures were elucidated as (3
)-oxyphyllacinol (
), (3
)- and (3
)-7-hydroxyoxyphyllacinol (
and
), (3
)-oxyphyllacinol-4'-
-β-d-glucopyranoside (
), (3
)-4″-hydroxyoxyphyllacinol (
), (3
)-3″-hydroxyoxyphyllacinol (
), (3
)-2″-hydroxyoxyphyllacinol (
), (3
)-2″-hydroxyoxyphyllacinol-2″-
-β-d-glucopyranoside (
), and (3
)-oxyphyllacinol-3-
-β-d-glucopyranoside (
) 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
, which was
-glucosylated on the diarylheptanoid alkyl chain, exhibited the most selective cytotoxic activities against melanoma cell lines with the IC
values ranging from 6.09 to 9.74 μM, indicating that it might be considered as a possible anti-cancer lead compound.