Planta Med 2008; 74(3): 290-292
DOI: 10.1055/s-2008-1034312
Natural Products Chemistry
Letter
© Georg Thieme Verlag KG Stuttgart · New York

Synthesis and Antimicrobial Activity of 3-Alkoxyjatrorrhizine Derivatives

Li-jun Wang1 , Xiao-li Ye2 , Xue-gang Li1 , Qing-lei Sun3 , Gang Yu1 , Xiao-gang Cao1 , Yan-ting Liang1 , Hua-san Zhang2 , Jia-zhou Zhou1
  • 1Chemistry Institute of Pharmaceutical resources, School of Pharmaceutical Science, Southwest University, Chongqing, P. R. China
  • 2School of Life Science, Southwest University, Chongqing, P. R. China
  • 3Shandong Analysis and Test Center, Shandong Academy of Science, Jinan, P. R. China
Weitere Informationen

Publikationsverlauf

Received: October 17, 2007 Revised: December 11, 2007

Accepted: December 17, 2007

Publikationsdatum:
26. Februar 2008 (online)

Preview

Abstract

The compounds 3-ethoxy- (2), 3-butoxy- (3), 3-hexyloxy- (4), 3-octyloxy- (5), 3-decyloxy- (6) and 3-dodecyloxyjatrorrhizine chlorides (7) were synthesized and tested for their antimicrobial activity in vitro to evaluate structure-activity relationships. Substitution of the H with alkyl groups at C-3-OH led to significant changes in the antimicrobial activity. The antimicrobial activity of the substituted derivatives was 32 - 1000 times higher than that of jatorrhizine (1), which increased as the aliphatic chain was elongated and then decreased slightly when the alkyl chain exceeded eight carbon atoms. 3-Octyloxyjatrorrhizine (5) displayed the highest antimicrobial activity of all compounds. The LD50 values of compounds 1 - 7 were more than 6000 mg/kg body weight, showing a low toxicity. The toxicities of compounds 2 - 7 were slightly lower than that of (1).

References

Prof. Dr. Xue-gang Li

Chemistry Institute of Pharmaceutical resources

School of Pharmaceutical Science

Southwest University

Chongqing 400715

People’s Republic of China

Telefon: +86-23-6825-0728

Fax: +86-23-6825-0728

eMail: Xuegangli2000@yahoo.com.cn