Anti-diabetic potential of Masclura tricuspidata leaves: Prenylated isoflavonoids with α-glucosidase inhibitory and anti-glycation activity
- Authors
- Jo, Yang Hee; Lee, Solip; Yeon, Sang Won; Turk, Ayman; Lee, Jae Hyuk; Hong, Seong-Min; Han, Yoo Kyong; Lee, Ki Yong; Hwang, Bang Yeon; Kim, Sun Yeou; Lee, Mi Kyeong
- Issue Date
- Sep-2021
- Publisher
- ACADEMIC PRESS INC ELSEVIER SCIENCE
- Keywords
- Cudracusisoflavones A-P; Glycation; Masclura tricuspidata; Molecular docking analysis; Prenylated isoflavonoids; α-glucosidase
- Citation
- Bioorganic Chemistry, v.114
- Journal Title
- Bioorganic Chemistry
- Volume
- 114
- URI
- https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/82082
- DOI
- 10.1016/j.bioorg.2021.105098
- ISSN
- 0045-2068
- Abstract
- Investigation of chemical constituents of Masclura tricuspidata leaves resulted in the isolation of 47 isoflavonoids possessing prenyl groups with different numbers and structures. Among them, sixteen compounds named cudracusisoflavones A-P (1–16) were first isolated from nature. The isoflavonoids isolated from M. tricuspidata leaves showed anti-diabetic effects as measured by inhibition on α-glucosidase activity and advanced glycation end-products (AGEs) formations. Especially, cudracusisoflavone L (12), a new compound, together with gancaonin M (27), erysenegalensein E (41) and millewanin G (44) showed strong α-glucosidase inhibition with IC50 values <10.0 μM. In addition, cudracusisoflavones A (1), D (4), M (13) and N (14), together with known prenylated isoflavonoids efficiently inhibited methylglyoxal (MGO)- or glyoxal (GO)-induced AGE formations. Structure activity relationship together with molecular docking analysis suggested the importance of hydroxy group and linear type of prenyl moiety for α-glucosidase inhibition. Conclusively, diverse prenylated isoflavonoids in M. tricuspidata leaves might ameliorate glycotoxicity-induced metabolic diseases. © 2021
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