Isolation of echinocystic acid-3-O-sulfate, a new triterpene, from Tetrapleura tetraptera, and evaluation of the mutagenic potential of molluscicidal extracts and isolates.
A known triterpene glycoside, 3-O-[beta-D-glucopyranosyl-(1"-6')-2'-acetamido-2'-deoxy-beta-D-gluco pyranosyl]olean-12-en-28-oic acid [3], and new sulfated triterpene, echinocystic acid-3-O-sodium sulfate [4], have been isolated from the stem bark of Tetrapleura tetraptera. Compound 3 was 100% lethal to Biomphalaria glabrata at 20 ppm, while 4 was not molluscicidal at the same concentration. In a forward mutation assay utilizing Salmonella typhimurium strain TM677, T. tetraptera stem bark extracts were found to be mutagenic in the absence of a metabolic activating system (S-9). An MeOH extract of the fruit exhibited weak mutagenic activity only in the presence of S-9. The stem bark isolates, which included aridanin [1], 3-O-(2'-acetamido-2'-deoxy-beta-D-glucopyranosyl)echinocystic acid [2], and compounds 3 and 4, were not mutagenic either with or without metabolic activation.
Ngassapa
O
O
Progam for Collaborative Research in the Pharmaceutical Sciences, College of Pharmacy, University of Illinois at Chicago 60680.
Beecher
C W
CW
Pezzuto
J M
JM
Farnsworth
N R
NR
Henderson
T O
TO
Boye
G L
GL
D000818:Animals; D001700:Biomphalaria / Q000187:drug effects; D001711:Biotransformation; D007887:Fabaceae / Q000737:chemistry*; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D008975:Molluscacides / Q000302:isolation & purification* / Q000493:pharmacokinetics / Q000633:toxicity; D009153:Mutagens / Q000302:isolation & purification* / Q000493:pharmacokinetics / Q000633:toxicity; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000302:isolation & purification / Q000493:pharmacokinetics / Q000633:toxicity; D010936:Plant Extracts / Q000633:toxicity*; D010946:Plants, Medicinal; D051381:Rats; D012486:Salmonella typhimurium / Q000235:genetics; D013055:Spectrophotometry, Infrared; D014961:X-Ray Diffraction
D008975:Molluscacides; D009153:Mutagens; D010936:Plant Extracts; C085391:echinocystic acid-3-O-sulfate; D009828:Oleanolic Acid