Isolation and structure identification of an active DNA strand-scission agent, (+)-3,4-di-hydroxy-8,9-methylenedioxypterocarpan.
A new pterocarpan, (+)-3,4-dihydroxy-8,9-methylenedioxypterocarpan [1], was isolated from the flowers of Petalostemon purpureus by a DNA strand-scission assay-guided fractionation procedure. Compound 1 demonstrated activity in a standard in vitro DNA strand-scission assay, and cytotoxicity toward a KB tumor cell line. Two other related pterocarpans [2, 3] isolated from same plant were found to be moderately active for KB cells, but were inactive in the DNA strand-scission assay. (+)-4-Hydroxy-3-methoxy-8,9-methylenedioxypterocarpan [2] has not been reported previously as a natural product, while (+)-maackiain [3] has been isolated only as an optically inactive racemate along with its optical antipode, the (-)-isomer.
Chaudhuri
S K
SK
Chemistry and Life Sciences Group, Research Triangle Institute, Research Triangle Park, North Carolina 27709, USA.
Huang
L
L
Fullas
F
F
Brown
D M
DM
Wani
M C
MC
Wall
M E
ME
D000970:Antineoplastic Agents / Q000302:isolation & purification* / Q000494:pharmacology; D001572:Benzofurans / Q000302:isolation & purification* / Q000494:pharmacology; D001578:Benzopyrans / Q000302:isolation & purification* / Q000494:pharmacology; D004273:DNA, Neoplasm / Q000737:chemistry / Q000187:drug effects*; D006801:Humans; D007624:KB Cells; D010946:Plants, Medicinal / Q000737:chemistry*; D036343:Pterocarpans
C100482:3,4-dihydroxy-8,9-methylenedioxypterocarpan; D000970:Antineoplastic Agents; D001572:Benzofurans; D001578:Benzopyrans; D004273:DNA, Neoplasm; D036343:Pterocarpans