Huperserratines A and B, Two Macrocyclic Lycopodium Alkaloids with an Unusual Skeleton from Huperzia serrata

Huperserratines A (1) and B (2), two Lycopodium alkaloids with an unprecedented 5-aza-bicyclo[10.4.0]­hexadecane skeleton and an oxime function, were isolated from Huperzia serrata. Their structures including absolute configurations were determined by extensive NMR spectroscopic and X-ray diffractio...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-05, Vol.85 (10), p.6803-6807
Main Authors: Wu, Xing-De, Li, Xiao-Nian, Peng, Li-Yan, Zhao, Qin-Shi
Format: Article
Language:English
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Summary:Huperserratines A (1) and B (2), two Lycopodium alkaloids with an unprecedented 5-aza-bicyclo[10.4.0]­hexadecane skeleton and an oxime function, were isolated from Huperzia serrata. Their structures including absolute configurations were determined by extensive NMR spectroscopic and X-ray diffraction analysis. Compounds 1 and 2 were the first examples of macrocyclic Lycopodium alkaloids with an aza-12-membered ring. A plausible biogenetic pathway of these compounds was also proposed. Compound 1 exhibited moderate anti-HIV-1 activity with an EC50 of 52.91 μg/mL and a therapy index greater than 3.78.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c00623