Molluscicidal acridone alkaloids from Angostura paniculata: isolation, structures, and synthesis.
Two novel acridone alkaloids, cuspanine [1] and cusculine [2], were isolated from the CH2Cl2 extract of the leaves of Angostura paniculata (Rutaceae). Their structures were established as 1-hydroxy-2,3,5,6-tetramethoxy-9-acridone for 1 and 1,2,3,5,6-pentamethoxy-9-acridone for 2 by means of spectroscopic studies, in particular nmr. These structural assignments were confirmed by synthesis, using a direct metallation method as a key reaction. Both alkaloids exhibited moderate molluscicidal activity against an aquatic snail, Biomphalaria glabrata, and cytotoxicity against several types of carcinoma cell lines.
Vieira
P C
PC
Division of Entomology and Parasitology, College of Natural Resources, University of California, Berkeley 94720.
Kubo
I
I
Kujime
H
H
Yamagiwa
Y
Y
Kamikawa
T
T
D000166:Acridines / Q000633:toxicity*; D000470:Alkaloids / Q000633:toxicity*; D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000633:toxicity; D001700:Biomphalaria / Q000502:physiology; D001938:Brazil; D006367:HeLa Cells; D006801:Humans; D008975:Molluscacides / Q000633:toxicity*; D010936:Plant Extracts / Q000032:analysis; D010947:Plants, Toxic / Q000737:chemistry*; D014407:Tumor Cells, Cultured / Q000187:drug effects
D000166:Acridines; D000470:Alkaloids; D000972:Antineoplastic Agents, Phytogenic; D008975:Molluscacides; D010936:Plant Extracts