ent-rosane and labdane diterpenoids from Sagittaria sagittifolia and their antibacterial activity against three oral pathogens

J Nat Prod. 2006 Feb;69(2):255-60. doi: 10.1021/np050479e.

Abstract

Seven new ent-rosane diterpenoids, sagittines A-G (1-7), together with one new labdane diterpene, 13-epi-manoyl oxide-19-O-alpha-l-2',5'-diacetoxyarabinofuranoside (8), were isolated from the whole plant of Sagittaria sagittifolia. The structures and relative configurations of 1-8 were characterized using spectroscopic means, chemical methods, and X-ray crystallography. Compounds 1-4 exhibited antibacterial activity against the oral pathogens Streptococcus mutans ATCC 25175 and Actinomyces naeslundiis ATCC 12104, with MIC values between 62.5 and 125 microg/mL. Compound 5 was active against only A. naeslundiis ATCC 12104, with an MIC value of 62.5 microg/mL.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Actinomyces / drug effects
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology*
  • Arabinose / analogs & derivatives*
  • Arabinose / chemistry
  • Arabinose / isolation & purification
  • Arabinose / pharmacology
  • Crystallography, X-Ray
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology*
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology*
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Molecular Structure
  • Plants, Medicinal / chemistry*
  • Sagittaria / chemistry*
  • Streptococcus mutans / drug effects

Substances

  • 13-epi-manoyl oxide-19-O-alpha-l-2',5'-diacetoxyarabinofuranoside
  • Anti-Bacterial Agents
  • Diterpenes
  • Drugs, Chinese Herbal
  • labdane
  • Arabinose