Enzymatic transformation products of phloretin as potent antiadipogenic compounds
- Authors
- Jeong, Gyeong Han; Cho, Jae-Hyeon; Park, Eui Kyun; Kim, Tae Hoon
- Issue Date
- Dec-2021
- Publisher
- Japan Society for Bioscience Biotechnology and Agrochemistry/Nippon Nogeikagaku Kai
- Keywords
- polyphenol oxidase; phloretin oxidation; biotransformation; pancreatic lipase; adipocyte differentiation
- Citation
- Bioscience, Biotechnology and Biochemistry, v.85, no.12, pp 2352 - 2359
- Pages
- 8
- Indexed
- SCIE
SCOPUS
- Journal Title
- Bioscience, Biotechnology and Biochemistry
- Volume
- 85
- Number
- 12
- Start Page
- 2352
- End Page
- 2359
- URI
- https://scholarworks.gnu.ac.kr/handle/sw.gnu/2964
- DOI
- 10.1093/bbb/zbab168
- ISSN
- 0916-8451
1347-6947
- Abstract
- Enzymatic structure modification of the representative chalcone phloretin (1) with polyphenol oxidase from Agaricus bisporus origin produced 2 new biphenyl-type phloreoxin (2) and phloreoxinone (3), and a previously undescribed (2R)-5,7,3',5'-tetrahydroxyflavanone (4). The structure of these new oxidized products 2-4 elucidated by interpreting the spectroscopic data (NMR and FABMS) containing the absolute stereochemistry is established by the analysis of the circular dichroism spectrum. Compared to the original phloretin, the new products (2) and (3) showed highly improved antiadipogenic potencies both toward pancreatic lipase and accumulation of 3T3-L1 cells. Also, phloreoxin (2) effectively inhibited the expression of C/EBP beta, PPAR gamma, and aP2 at the mRNA level in the 3T3 adipocytes. Thus, phloreoxin (2), containing a biphenyl moiety catalyzed by A. bisporus polyphenol oxidase, have the potential to influence the antiadipogenic capacity. [GRAPHICS] Enzymatic oxidation products 2 and 3 of phloretin as potent antiadipogenic effects.
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