ent-Strobane and ent-Pimarane Diterpenoids from Siegesbeckia pubescens

J Nat Prod. 2017 Jan 27;80(1):19-29. doi: 10.1021/acs.jnatprod.6b00150. Epub 2016 Dec 23.

Abstract

Two strobane diterpenoids, strobols A (1) and B (2), 15 new pimarane diterpenoids (3-6 and 8-18), and the known compounds kirenol (19), darutigenol (20), and ent-2β,15,16,19-tetrahydroxypimar-8(14)-ene (7) were isolated from the aerial parts of Siegesbeckia pubescens Makino. The structures of the new compounds were established based on the interpretation of HRESIMS and NMR analysis. The configurations of 1, 6, and 17 were confirmed by X-ray crystallographic data. Compounds 3, 5, and 11 inhibited the migration of MB-MDA-231 breast cancer cells induced by the chemokine epithelial growth factor, with IC50 values of 4.26, 3.45, and 9.70 μM, respectively.

MeSH terms

  • Abietanes / chemistry
  • Abietanes / isolation & purification*
  • Abietanes / pharmacology*
  • Asteraceae / chemistry*
  • Crystallography, X-Ray
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology*
  • Diterpenes, Kaurane / chemistry
  • Diterpenes, Kaurane / isolation & purification*
  • Diterpenes, Kaurane / pharmacology*
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology*
  • Humans
  • Molecular Structure
  • Plant Oils / chemistry*

Substances

  • Abietanes
  • Diterpenes
  • Diterpenes, Kaurane
  • Drugs, Chinese Herbal
  • Plant Oils
  • kirenol
  • strobol A
  • strobol B
  • darutigenol