Substolides A-G, germacrane sesquiterpenoids from Salvia substolonifera

Phytochemistry. 2015 Dec:120:28-35. doi: 10.1016/j.phytochem.2015.09.013. Epub 2015 Oct 17.

Abstract

Chemical investigation of the whole plants of Salvia substolonifera E.Peter yielded seven germacrane sesquiterpenoids, substolides A-G (1-7), an ethoxylated artifact (8), and two known analogues, 6β-tigloyloxyglechomafuran (9) and castanin F (10). Four germacrane 8-acetylation derivatives (1a-4a) were obtained by chemical transformation. Their structures and relative or absolute configurations were elucidated by intensive spectroscopic methods, and single-crystal X-ray diffraction analysis. Compounds 1a-4a, and 5-10 were evaluated for their in vitro anti-angiogenic effects. Compounds 7 and 9 significantly inhibited VEGF-induced human umbilical vein endothelial cell (HUVEC) proliferation in vitro, with IC50 values of 16.15 ± 0.19, and 4.03 ± 0.26 μM, respectively. The structure activity relationship of these compounds is discussed.

Keywords: Acetylation; Anti-angiogenic effect; Germacrane; Lamiaceae; Salvia substolonifera E.Peter; Sesquiterpenoid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology
  • Human Umbilical Vein Endothelial Cells / drug effects
  • Humans
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Salvia / chemistry*
  • Sesquiterpenes, Germacrane / chemistry
  • Sesquiterpenes, Germacrane / isolation & purification*
  • Sesquiterpenes, Germacrane / pharmacology
  • Vascular Endothelial Growth Factor A / pharmacology

Substances

  • Drugs, Chinese Herbal
  • Sesquiterpenes, Germacrane
  • Vascular Endothelial Growth Factor A