Lycocasuarines A–C, Lycopodium alkaloids from Lycopodiastrum casuarinoides. Issue 52 (27th December 2017)

• Record Type: Journal Article
• Authors: Wang, Lu-Lu; Zhou, Zhong-Bo; Zhu, Xin-Liu; Yuan, Fang-Yu; Miyamoto, Tomofumi; Pan, Ke
• Is Part Of: Tetrahedron letters. Volume 58:Issue 52(2017)
• Page Start: 4827
• Page End: 4831
• Publication Date: 2017-12-27
• Subjects: Lycopodiastrum casuarinoides -- Lycopodium alkaloids -- Lycodine-type alkaloids -- Acetylcholinesterase; OIOHNJHCOIQZML-KCEWHOTPSA-N; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.11.019
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Three new lycodine-type Lycopodium alkaloids were isolated from Lycopodiastrum casuarinoides. Lycocasuarine A (1 ) possesses a rearranged five-membered ring D resulting from C-8/C-15 cleavage and a new C-7/C-15 linkage. Lycocasuarine B (2 ) is the first Lycopodium alkaloid found to bear an additional carbon (C-17) directly bonded to C-8. Lycocasuarine C (3 ) showed inhibitory activity against acetylcholinesterase. Abstract: Three lycodine-type Lycopodium alkaloids (1 –3 ) were isolated from Lycopodiastrum casuarinoides . Their structures were elucidated by spectroscopic analysis, single-crystal X-ray crystallography, and computational methods. Compound1 possesses a rearranged five-membered ring D resulting from C-8/C-15 cleavage and a new C-7/C-15 linkage. Compound2 is the first Lycopodium alkaloid found to bear an additional carbon (C-17) directly bonded to C-8, which is particularly unusual from a biogenetic point of view. Compounds1 –3 were evaluated for acetylcholinesterase inhibitory activities.