Semisynthesis and acetylcholinesterase inhibitory activity of stemofoline alkaloids and analogues

• Main Authors: Kwankamol Sastraruji, Thanapat Sastraruji, Stephen G. Pyne, Alison T. Ung, Araya Jatisatienr, Wilford Lie
• Format: Journal
• Published: 2018
• Subjects: Biochemistry, Genetics and Molecular Biology; Chemistry; Medicine; Pharmacology, Toxicology and Pharmaceutics
• Online Access: https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=77952982010&origin=inward; http://cmuir.cmu.ac.th/jspui/handle/6653943832/50569
• Institution: Chiang Mai University

Semisynthesis of the known Stemona alkaloids oxystemofoline (7) and methoxystemofoline (8) has been achieved starting from (11Z)-1′,2′- didehydrostemofoline (6), which confirmed their structures and absolute configurations. The synthesis of (1′R)-hydroxystemofoline (9) helped establish this compound as a natural product from Stemona aphylla. (1′S)-Hydroxystemofoline (10) and a number of related analogues were also prepared. In a TLC bioautographic assay, 9 was found to be the most active acetylcholinesterase inhibitor, but it was not as active as galanthamine. © 2010 The American Chemical Society and American Society of Pharmacognosy.