Microbial Transformation and Biological Activities of the Prenylated Aromatic Compounds from Broussonetia kazinoki

• Published in: Molecules (Basel, Switzerland) Vol. 27; no. 6; p. 1879
• Main Authors: Choi, EunA, Han, Fubo, Park, Jisu, Lee, Ik-Soo
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 14-03-2022; MDPI
• Subjects: Acne; Aromatic compounds; Broussonetia - chemistry; Broussonetia kazinoki; Carbon; Cell lines; Cytotoxicity; Flavonoids - chemistry; Glucose; Melanoma; Metabolites; microbial transformation; Microorganisms; Monophenol Monooxygenase; NMR; Nuclear magnetic resonance; Polyphenols; Skin; Spectrum analysis; Transformations; Tyrosinase; tyrosinase inhibition; microbial transformation; tyrosinase inhibition; Broussonetia kazinoki; cytotoxicity
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules27061879

has been used as a traditional medicine for the treatment of burns and acne, and its extracts have been found to show tyrosinase inhibitory and anticancer activities. In this study, the tyrosinase inhibitory and cytotoxic activities of
were explored, leading to the isolation of kazinol C (
), kazinol E (
), kazinol F (
), broussonol N (
), and kazinol X (
), of which the compounds
and
have not been previously reported. Microbial transformation has been recognized as an efficient tool to generate more active metabolites. Microbial transformation of the major compounds
and
was conducted with
, where four glucosylated metabolites (
-
) were produced from
, while one hydroxylated (
) and one glucosylated (
) metabolites were obtained from
. Structures of the isolated metabolites were determined by extensive spectroscopic analyses. All compounds were evaluated for their tyrosinase inhibitory and cytotoxic activities. Compound
and its metabolites, kazinol Y (
) and kazinol F-4″-
-β-d-glucopyranoside (
), exhibited the most potent tyrosinase inhibitory activities with the IC
values ranging from 0.71 to 3.36 µM. Meanwhile, none of the metabolites, except for kazinol C-2',3″-di-
-β-d-glucopyranoside (
), showed moderate cytotoxic activities (IC
17.80 to 24.22 µM) against A375P, B16F10 and B16F1 cell lines.