Ponapensin, a cyclopenta[bc]benzopyran with potent NF-kappaB inhibitory activity from Aglaia ponapensis.
Two new compounds, a cyclopenta[bc]benzopyran, ponapensin (1), and an aglaialactone, 5,6-desmethylenedioxy-5-methoxy-aglalactone (2), together with nine known compounds were isolated from the CHCl(3) soluble extract of the leaves and twigs of Aglaia ponapensis. Their structures were established by spectroscopic data interpretation. Ponapensin (1) exhibited significant NF-kappaB inhibitory activity in an Elisa assay, and was found to be more potent than the positive control rocaglamide. All of the compounds isolated were also tested in a panel of human cancer cell lines, with the known sterol E-volkendousin (3) and methyl rocaglate (aglafoline) found to be the only active substances.
Salim
Angela A
AA
Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH 43210, USA.
Pawlus
Alison D
AD
Chai
Hee-Byung
HB
Farnsworth
Norman R
NR
Douglas Kinghorn
A
A
Carcache-Blanco
Esperanza J
EJ
D031602:Aglaia / Q000737:chemistry*; D001572:Benzofurans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001578:Benzopyrans / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D004797:Enzyme-Linked Immunosorbent Assay; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D006801:Humans; D015394:Molecular Structure; D016328:NF-kappa B / Q000037:antagonists & inhibitors*; D018515:Plant Leaves / Q000737:chemistry
C519000:5,6-desmethylenedioxy-5-methoxyaglalactone; D001572:Benzofurans; D001578:Benzopyrans; D006575:Heterocyclic Compounds, 3-Ring; D016328:NF-kappa B; C518999:ponapensin; C107772:rocaglamide