Phytochemical Studies on Stemona Plants:  Isolation of Stemofoline Alkaloids

• Published in: Journal of natural products (Washington, D.C.) Vol. 68; no. 12; pp. 1763 - 1767
• Main Authors: Sastraruji, Thanapat, Jatisatienr, Araya, Pyne, Stephen G, Ung, Alison T, Lie, Wilford, Williams, Morwenna C
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01-12-2005; Glendale, AZ American Society of Pharmacognosy
• Subjects: alkaloids; Alkaloids - chemistry; Alkaloids - isolation & purification; Biological and medical sciences; chemical structure; General pharmacology; Heterocyclic Compounds, 4 or More Rings - chemistry; Heterocyclic Compounds, 4 or More Rings - isolation & purification; hydroxystemofoline; Medical sciences; Molecular Structure; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Plant Roots - chemistry; Plants, Medicinal - chemistry; spectral analysis; stemofolenol; stemofoline alkaloids; stemofolinoside; Stemona; Stemonaceae - chemistry; stereochemistry; Stereoisomerism; Thailand; Thailand; Asia; Monocotyledones; Five membered ring; Root; Stemonaceae; Pharmacognosy; Relative configuration; Lactone; Tetracyclic compound; Oxygen heterocycle; Medicinal plant; Alkaloid; Angiospermae; Plant origin; Isolation; Spermatophyta; Chemical synthesis; Structural analysis; Hemisynthesis; Oxygen nitrogen heterocycle; Below ground plant part
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np050361y

Six new stemofoline alkaloids, (2‘R)-hydroxystemofoline (5), (3‘R)-stemofolenol (6), (3‘S)-stemofolenol (7), 1‘,2‘-didehydrostemofoline-N-oxide (8), the first C19 stemofoline alkaloid, methylstemofoline (9), and the first glycosidated Stemona alkaloid, stemofolinoside (10), and three known alkaloids, (2‘S)-hydroxystemofoline (2), (11Z)-1‘,2‘-didehydrostemofoline (3), and (11E)-1‘,2‘-didehydrostemofoline (4), have been isolated from a root extract of an unidentified Stemona species. The structure and relative configuration of these new alkaloids have been determined by spectral data interpretation and from semisynthetic studies.