neo-Clerodane Diterpenoids from Salvia polystachya Stimulate the Expression of Extracellular Matrix Components in Human Dermal Fibroblasts

J Nat Prod. 2017 Nov 22;80(11):3003-3009. doi: 10.1021/acs.jnatprod.7b00591. Epub 2017 Nov 14.

Abstract

Eleven neo-clerodane diterpenoids (1-11) including the new analogues 1, 2, and 10, and 3',5,6,7-tetrahydroxy-4'-methoxyflavone (12) were isolated from the aerial parts of Salvia polystachya. Polystachyne G (1) and 15-epi-polystachyne G (2) were isolated as an epimeric mixture, containing a 5-hydroxyfuran-2(5H)-one unit in the side chain at C-12 of the neo-clerodane framework. Polystachyne H (10) contains a 1(10),2-diene moiety and a tertiary C-4 hydroxy group. The structures of these compounds were established by analysis of their NMR spectroscopic and MS spectrometric data. The absolute configurations of compounds 3, 4, and 10 were determined through single-crystal X-ray diffraction analysis. The antibacterial, antifungal, and phytotoxic activities of the diterpenoids were determined. In addition, the stimulatory effect of the expression of extracellular matrix components of nine of the isolates (1-8 and 11) was assayed. Compounds 1-4, 8, and 11 increased the expression of the genes codifying for type I, type III, and type V collagens and for elastin.

MeSH terms

  • Bacillus / drug effects
  • Candida albicans / drug effects
  • Collagen / drug effects
  • Collagen / genetics
  • Crystallography, X-Ray
  • Diterpenes, Clerodane / chemistry
  • Diterpenes, Clerodane / isolation & purification*
  • Diterpenes, Clerodane / pharmacology*
  • Elastin / drug effects
  • Elastin / genetics
  • Escherichia coli / drug effects
  • Extracellular Matrix / drug effects*
  • Fibroblasts / drug effects*
  • Flavonoids / chemistry
  • Flowers / chemistry
  • Humans
  • Mexico
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / chemistry
  • Polymerase Chain Reaction
  • Salvia / chemistry*

Substances

  • 15-epi-polystachyne G
  • 4'-methoxyflavone
  • Diterpenes, Clerodane
  • Flavonoids
  • polystachyne G
  • Collagen
  • Elastin