Synthesis and Antimicrobial Activity of 3-Alkoxyjatrorrhizine Derivatives

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).

Coptis chinensis Franch. - Ranunculaceae - jatrorrhizine - 3-alkoxyjatrorrhizine derivatives - antimicrobial activity - acute toxicity

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