beta-Methoxy-gamma-methylene-alpha,beta-unsaturated-gamma-butyrolactones from Artabotrys hexapetalus.
The dichloromethane extract of the aerial parts of Artabotrys hexapetalus afforded three beta-methoxy-gamma-methylene-alpha,beta-unsaturated-gamma-butyrolactones, which are proposed to be derived from a C(18) unsaturated fatty acid by a biosynthetic route similar to that proposed for the Annonaceous acetogenins. The structure of the unique beta-methoxy-gamma-methylene-substituted, alpha,beta-unsaturated-gamma-butyrolactone ring of artapetalins A-C (1-3) was determined by 2D-NMR spectroscopic analyses. Two unusual simple butyrolactones, (+)-tulipalin B and (2R,3R)- 3-hydroxy-2-methylbutyrolactone were also isolated from this species.
Wong
Ho Fai
HF
Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong.
Brown
Geoffrey D
GD
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification; D029061:Annonaceae / Q000737:chemistry*; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification*; D001952:Bridged-Ring Compounds / Q000737:chemistry / Q000302:isolation & purification
D000962:Antimalarials; D001952:Bridged-Ring Compounds; C450173:artapetalin A; C450174:artapetalin B; C450175:artapetalin C; D015107:4-Butyrolactone