Revision of NMR assignment for Morin-3-O-glucoside and microbial production of Morin-2'-O-glucoside.

J Nat Med

Department of Pharmacognosy, Graduate School of Biomedical and Health Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima, 734-8553, Japan.

Published: March 2024

AI Article Synopsis

  • * Morin-3-O-glucoside, the glycoside of morin, was first reported in 2008, but its chemical properties were not adequately defined compared to similar compounds.
  • * In this study, researchers created morin-3-O-glucoside through microbial transformation and discovered a new compound, morin-2'-O-glucoside, refining the NMR data for better structural understanding.

Article Abstract

Morin is a flavonol having 2',4'-dihydroxy group on B-ring identified especially in Moraceae plants. While morin is widely known, its glycosides are relatively rare. To the best of our knowledge, morin-3-O-glucoside (1) was first reported in 2008. However, the reported chemical shift values of 1 were unsatisfactory with those of the aglycone, morin, which is rather similar to quercetin-3-O-glucoside (2). Therefore, we prepared morin-3-O-glucoside (1) by microbial transformation of morin with Cunninghamella sp., and the NMR assignment was reinvestigated. The microbial culture also produced another compound (3). The NMR and MS analyses of 3 revealed it as a novel compound, morin-2'-O-glucoside (3).In this study, the revision of the NMR assignment of morin-3-O-glucoside (1), and the preparation and structural elucidation of a novel compound, morin-2'-O-glucoside (3), were described.

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http://dx.doi.org/10.1007/s11418-023-01771-1DOI Listing

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