Anti-complement activity of norlignans and terpenes from the stem bark of Styrax japonica

Planta Med. 2004 Dec;70(12):1210-5. doi: 10.1055/s-2004-835853.

Abstract

A new norlignan, styraxlignolide A (1), and two new terpenes, styraxosides A (2) and B (3), were isolated from the MeOH-soluble fraction of Styrax japonica Sieb. et Zucc. (Styracaceae) stem bark, together with two known compounds, egonol (4) and masutakeside I (5). The new compounds were determined as 5-(3''-hydroxypropyl)-7-methoxy-2-(3',4'-dimethoxyphenyl)-benzofuran 3''- O-[beta-D-xylopyranoside-(1-->6)-beta- D-glucopyranoside] (1), 3beta,7beta-dihydroxy-4alpha,4beta,8beta,10beta,14alpha-pentamethyl-5alpha-gon-16-en-2-one 3-O-[beta-D-glucopyranoside-(1-->2)-beta-D-glucopyranoside] (2), and 3beta,17beta-dihydroxy-28-norolean-12-en-16-one 3-O-[alpha-L-rhamopyranoside-(1-->2)-beta-D-glucuronopyranoside] (3) by spectroscopic means including 2D-NMR. The five compounds were tested in vitro for anti-complement activity against the complement system. Compounds 1, 3, 4, and 5 displayed inhibitory activity in the anti-complement assay, with IC50 values of 123, 65, 33, and 166 microM, respectively. Compound 1a and camellenodiol (3a), obtained from acid hydrolysis of 1 and 3, respectively, did not affect the hemolytic activity of human serum against sensitized erythrocytes. This shows that a sugar seems to play a role of enhancing significantly anti-complement activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Complement System Proteins / drug effects*
  • Disaccharides / administration & dosage
  • Disaccharides / pharmacology
  • Disaccharides / therapeutic use
  • Humans
  • Inhibitory Concentration 50
  • Lignans / administration & dosage
  • Lignans / pharmacology
  • Lignans / therapeutic use
  • Magnetic Resonance Spectroscopy
  • Phytotherapy*
  • Plant Bark
  • Plant Extracts / administration & dosage
  • Plant Extracts / pharmacology*
  • Plant Extracts / therapeutic use
  • Styrax*
  • Terpenes / administration & dosage
  • Terpenes / pharmacology
  • Terpenes / therapeutic use

Substances

  • Disaccharides
  • Lignans
  • Plant Extracts
  • Terpenes
  • styraxlignolide A
  • Complement System Proteins