Two new diterpenoids from the rhizomes of Zingiber officinale

Nat Prod Res. 2023 Jul;37(13):2255-2262. doi: 10.1080/14786419.2022.2038595. Epub 2022 Feb 19.

Abstract

Two undescribed labdane diterpenoids (5S,8S,9R,10S,11E)-8,17-epoxy-13,14-dinorlabd-11-en-13-one (1) and (5S,9R,10S,12E)-17-hydroxy-labd-7,12-dien-15(16)-olide (2), together with seven known sesquiterpenoids (3-9) and two known monoterpenoids (10-11) were isolated from the dried rhizome of Zingiber officinale. Their structures were elucidated by detailed spectroscopic data (IR, UV, HR-ESI-MS, 1D and 2D NMR), X-ray crystallographic and ECD analysis. Moreover, all the 11 compounds were tested for α-glucosidase inhibitory effects and 9 was found to exhibit stronger inhibitory effects at IC50 = 4.8 μM against a positive control acarbose with IC50 = 414.6 μM.

Keywords: X-ray crystallographic analysis; Zingiber officinale Roscoe; diterpenoid; α-glucosidase inhibitory activity.

MeSH terms

  • Diterpenes* / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Rhizome / chemistry
  • Zingiber officinale* / chemistry

Substances

  • Diterpenes