Rare, seven-membered cyclic ether labdane diterpenoid from Dodonaea polyandra.
Previous phytochemical studies on the leaf resin of dioecious plant species Dodonaea polyandra have identified the presence of furanoclerodane diterpenoids. As part of ongoing research on this species the chemical profile of an individual plant displaying male flowers was investigated. Repeated chromatographic separation of a resinous extract from the leaves of the plant yielded three labdane diterpenoids, 13,17-epoxy-13-methyl-15-oxo-labda-7-ene (1), 17-hydroxy-13-methyl-labda-7,13Z-diene-15-oic acid (2) and 13-methyl-17-oxo-labda-7,13Z-diene-15-oic acid (3) and a fourth known labdane diterpenoid (4) reported as being isolated from a natural source for the first time. Structural elucidation was carried out using conventional 1D and 2D NMR and mass spectrometry together with other complementary techniques (UV and IR). The leaf extract from this individual of D. polyandra with male flowers present displays a marked difference in the chemical composition of diterpenoids compared to previously studied extracts from the leaves of this species.
Sansom Institute for Health Research, School of Pharmacy and Medical Sciences, University of South Australia, Adelaide, South Australia 5000, Australia. bradley.simpson@unisa.edu.au
Bradley S
BS
Simpson
David J
DJ
Claudie
Nick M
NM
Smith
Ross A
RA
McKinnon
Susan J
SJ
Semple
D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification*; D004988:Ethers, Cyclic / Q000737:chemistry / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy / Q000592:standards; D008968:Molecular Conformation; D012015:Reference Standards; D029631:Sapindaceae / Q000737:chemistry*
D004224:Diterpenes; D004988:Ethers, Cyclic; C433017:labdane