Semisynthesis and biological activity of stemofoline alkaloids

• Main Authors: Morwenna C. Baird, Stephen G. Pyne, Alison T. Ung, Wilford Lie, Thanapat Sastraruji, Araya Jatisatienr, Chaiwat Jatisatienr, Srisulak Dheeranupattana, Jaturong Lowlam, Sukanya Boonchalermkit
• 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=65649116635&origin=inward; http://cmuir.cmu.ac.th/jspui/handle/6653943832/48885
• Institution: Chiang Mai University

The semisynthesis of the Stemona alkaloids (3′R)-stemofolenol (1), (3′S)-stemofolenol (2), methylstemofoline (3), and (3′S)- hydroxystemofoline (5) and the unnatural analogues (11E)-methylstemofoline (15) and 3′R-hydroxystemofoline (11) has been achieved starting from (11Z)-1′,2′-didehydrostemofoline (4). This synthesis allowed, for the first time, access to diastereomerically enriched samples of 1 and 2 and the assignment of their absolute configurations at C-3′. These compounds were obtained in sufficient quantities to allow for their biological testing. In a quantitative assay as AChE inhibitors, (11Z)-1′,2′- didehydrostemofoline (4) and (3′S)-hydroxystemofoline (5) were found to be the most active. © 2009 American Chemical Society and American Society of Pharmacognosy.