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Paper | Regular issue | Vol 96, No. 2, 2018, pp.273-285
Published online, 19th January, 2018
DOI: 10.3987/COM-17-13854
Coumarins with Anti-Melanogenesis Activities from a Chemically Engineered Extract of a Marine-Derived Fungus

Hitoshi Kamauchi, Kaoru Kinoshita, and Kiyotaka Koyama*

*Department of Pharmacognosy and Phytochemistry, Pharmaceutical Sciences, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan

Abstract

Chemical investigation of new resources is critical for developing medicinal leads. Chemically engineered extracts, a technique for derivatization of natural extracts, was performed on crude extracts of marine-derived fungus Eurotium rubrum; the resulting reaction mixture exhibited enhanced tyrosinase inhibition. Coumarin derivatives (1-3) were isolated from this chemically engineered extract. The structures of 1-3 were established using NMR, MS, and IR methods, revealing coumarin structures with side chains biosynthesized by the acetate-malonate pathway. 1-3 showed tyrosinase inhibition (IC50 = 7.7, 13.3, and 9.5 μM, respectively) and anti-melanogenesis activity (IC50 = 6.6, 7.2, and 6.6 μM, respectively, against B16 melanoma cells).