Phytochemical studies on Stemona burkillii prain: two new dihydrostemofoline alkaloids.
Two new dihydrostemofoline alkaloids, 11(S),12(R)-dihydrostemofoline (3) and stemoburkilline (4), along with stemofoline (1) and 2'-hydroxystemofoline (2) have been isolated from a root extract of Stemona burkillii Prain. The structure and relative configuration of 3 have been determined via spectroscopic data and from comparison with synthetic 11(S),12(S)-dihydrostemofoline (5). The configuration of the exo-cyclic alkene group in 4 is tentively assigned as E on the basis of mechanistic considerations.
Mungkornasawakul
Pitchaya
P
Department of Chemistry, University of Wollongong, New South Wales, 2522, Australia.
Pyne
Stephen G
SG
Jatisatienr
Araya
A
Lie
Wilford
W
Ung
Alison T
AT
Issakul
Kritchaya
K
Sawatwanich
Auntika
A
Supyen
Damrat
D
Jatisatienr
Chaiwat
C
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry / Q000302:isolation & purification*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D041901:Stemonaceae / Q000737:chemistry*; D013785:Thailand
C493706:11(S),12(R)-dihydrostemofoline; D000470:Alkaloids; D005663:Furans; D006576:Heterocyclic Compounds, 4 or More Rings; C493707:stemoburkilline; C430220:stemofoline