Phytochemical studies on Stemona burkillii prain: two new dihydrostemofoline alkaloids

Pitchaya Mungkornasawakul; Stephen G Pyne; Araya Jatisatienr; Wilford Lie; Alison T Ung; Kritchaya Issakul; Auntika Sawatwanich; Damrat Supyen; Chaiwat Jatisatienr

doi:10.1021/np049791z

Phytochemical studies on Stemona burkillii prain: two new dihydrostemofoline alkaloids

J Nat Prod. 2004 Oct;67(10):1740-3. doi: 10.1021/np049791z.

Authors

Pitchaya Mungkornasawakul¹, Stephen G Pyne, Araya Jatisatienr, Wilford Lie, Alison T Ung, Kritchaya Issakul, Auntika Sawatwanich, Damrat Supyen, Chaiwat Jatisatienr

Affiliation

¹ Department of Chemistry, University of Wollongong, New South Wales, 2522, Australia.

PMID: 15497953
DOI: 10.1021/np049791z

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemistry
Alkaloids / isolation & purification*
Furans / chemistry
Furans / isolation & purification*
Heterocyclic Compounds, 4 or More Rings / chemistry
Heterocyclic Compounds, 4 or More Rings / isolation & purification*
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Plant Roots / chemistry
Plants, Medicinal / chemistry*
Stemonaceae / chemistry*
Thailand

Substances

11(S),12(R)-dihydrostemofoline
Alkaloids
Furans
Heterocyclic Compounds, 4 or More Rings
stemoburkilline
stemofoline