Biotransformation of isoimperatorin and imperatorin by Glomerella cingulata and beta-secretase inhibitory activity

Bioorganic & Medicinal Chemistry
Shinsuke Marumoto, Mitsuo Miyazawa

Abstract

Biotransformation studies conducted on the furanocoumarins isoimperatorin (1) and imperatorin (3) have revealed that 1 was metabolized by Glomerella cingulata to give the corresponding reduced acid, 6,7-furano-5-prenyloxy hydrocoumaric acid (2), and 3 was transformed by G. cingulata to give the dealkylated metabolite, xanthotoxol (4) in high yields (83% and 81%), respectively. The structures of the new compound 2 have been established on the basis of spectral data. The metabolites 2 and 4 were tested for the beta-secretase (BACE1) inhibitory activity in vitro, and metabolite 2 slightly inhibited the beta-secretase activity with an IC(50) value of 185.6+/-6.8 microM. The metabolite 4 was less potent activity than compounds 1-3. In addition, methyl ester (2Me), methyl ether (2a) and methyl ester and ether (2aMe) of 2 were synthesized, and investigated for the ability to inhibit beta-secretase. Compound 2aMe exhibited the best beta-secretase inhibitory activity at the IC(50) value 16.2+/-1.2 microM and found to be the 2aMe showed competitive mode of inhibition against beta-secretase with K(i) value 11.3+/-2.8 microM.

References

Nov 7, 2006·Phytomedicine : International Journal of Phytotherapy and Phytopharmacology·S-Y JeonK-S Song

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Citations

Oct 27, 2011·Journal of Oleo Science·Shinsuke Marumoto, Mitsuo Miyazawa
Jul 28, 2016·Phytochemistry Reviews : Proceedings of the Phytochemical Society of Europe·Ewelina Kozioł, Krystyna Skalicka-Woźniak
Jul 6, 2014·Phytochemistry·Xiong-Hao LinMin Ye
Dec 17, 2014·Chemico-biological Interactions·Jiaojiao CaoJiang Zheng
Feb 1, 2017·Journal of Asian Natural Products Research·Xiu-Lan XinXiang-Ge Tian
Jun 10, 2010·Journal of Agricultural and Food Chemistry·Shinsuke Marumoto, Mitsuo Miyazawa
Dec 30, 2010·Journal of Natural Products·Mai FujiwaraMitsuo Miyazawa

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