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

J Nat Med. 2024 Mar;78(2):403-410. doi: 10.1007/s11418-023-01771-1. Epub 2024 Jan 18.

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.

Keywords: Cunninghamella; Microbial transformation; Morin.

MeSH terms

  • Flavones*
  • Flavonoids* / chemistry
  • Flavonols
  • Glucosides* / chemistry
  • Glycosides / chemistry

Substances

  • morin
  • Flavonoids
  • Glucosides
  • Glycosides
  • Flavonols
  • Flavones