Labdane- type diterpenoids and sesquiterpenes from Curcuma aromatica and their nitric oxide inhibitory activity in lipopolysaccharide-stimulated RAW264.7 macrophages

J Asian Nat Prod Res. 2024 Mar;26(3):387-393. doi: 10.1080/10286020.2023.2220273. Epub 2023 Jun 8.

Abstract

One new labdane-type diterpenoid, 3β,15-dihydroxylabda-8(17),12E-dien-16,15-olide (1) named curcumatin and twelve known compounds, coronarin D (2), isocoronarin D (3), (E)-labda-8(17),12-diene-15,16-dial (4), zerumin A (5), (E)-labda-8(17),12-dien-15,16-dioic acid (6), furanodiene (7), linderazulene (8), zedoarol (9), zedoarondiol (10), germacrone-1,10-epoxide (11), germacrone-4,5-epoxide (12), and zingiberenol (13) were isolated from the ethanol extract of the roots of Curcuma aromatica Salisb. Their structures were elucidated by 1D-, 2D-NMR spectroscopic analysis, HR-ESI-MS, and comparing with the NMR data reported in the literature. Compounds 2, 5, and 13 significantly inhibited the nitric oxide production effect in LPS-stimulated RAW 264.7 macrophages with IC50 values of 8.8 ± 1.7, 4.0 ± 0.9, and 6.2 ± 0.4 µM, respectively.

Keywords: Curcuma aromatica; curcumatin; labdane; nitric oxide; zingiberaceae.

MeSH terms

  • Curcuma / chemistry
  • Diterpenes* / chemistry
  • Diterpenes* / pharmacology
  • Epoxy Compounds / pharmacology
  • Lipopolysaccharides / pharmacology
  • Macrophages
  • Molecular Structure
  • Nitric Oxide
  • Sesquiterpenes* / pharmacology
  • Sesquiterpenes, Germacrane*

Substances

  • germacrone
  • Lipopolysaccharides
  • Nitric Oxide
  • Sesquiterpenes
  • Diterpenes
  • Epoxy Compounds
  • Sesquiterpenes, Germacrane