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Concise Total Synthesis of Complanadine A Enabled by Pyrrole-to-Pyridine Molecular Editing.
Synthesis (Stuttg)
January 2024
Department of Chemistry, Purdue University, 720 Clinic Drive, West Lafayette, Indiana 47907, USA.
alkaloid complanadine A, isolated by Kobayashi et al. in 2000, is a complex and unsymmetrical dimer of lycodine. Biologically, it is a novel and promising lead compound for the development of new treatment for neurodegenerative disorders and persistent pain management.
View Article and Find Full Text PDFThe Chemistry and Biology of Lycopodium Alkaloids.
Chem Biodivers
August 2024
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, People's Republic of China.
Article Synopsis
- * LAs have distinct tricyclic or tetracyclic structures and play important roles in inhibiting acetylcholinesterase, making them a focus of scientific research.
- * This review compiles and categorizes all known LAs from 1881 to December 2023, addressing the lack of comprehensive summaries on their classification and biological activities.
Lycopodium alkaloids from Huperzia serrata and their cholinesterase inhibitory activities.
Phytochemistry
July 2024
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China; University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China. Electronic address:
Huperzia serrata, belonging to the Lycopodiaceae family, has been traditionally utilized for the management of treating rheumatic numbness, arthritic pain, dysmenorrhea, and contusions. This plant is a rich source of lycopodium alkaloids, some of which have demonstrated notable cholinesterase inhibitory activity. The objective of this study was to identify lycopodium alkaloids with cholinesterase inhibitory properties from H.
View Article and Find Full Text PDFLycocasine A, a Alkaloid from and Its Acid-Sensing Ion Channel 1a Inhibitory Activity.
Molecules
April 2024
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China.
A novel alkaloid, lycocasine A (), and seven known alkaloids (-), were isolated from . Their structures were determined through NMR, HRESIMS, and X-ray diffraction analysis. Compound features an unprecedented 5/6/6 tricyclic skeleton, highlighted by a 5-aza-tricyclic[6,3,1,0]dodecane motif.
View Article and Find Full Text PDFSynthetic Efforts toward Lannotinidine G Based on an Aziridinium-Mediated Ring Contraction and Dienyne Metathesis.
Org Lett
April 2024
Department of Chemistry, New York University, New York, New York 10003, United States.
Lannotinidine G is a unique Lycopodium alkaloid that features a tricyclic [6/6/6] core with 3 contiguous stereocenters and a 1,3-diene moiety in addition to a 7-membered lactone. Herein, we disclose our efforts toward the synthesis of this natural product, which achieved the construction of the aza-tricyclic core with the correct configuration at its three stereocenters. Key features of our strategy include a highly diastereoselective Fráter-Seebach alkylation and Corey-Chaykovsky type epoxide formation, an unusual aziridinium-mediated ring contraction for the formation of the piperidine moiety, and a regioselective dienyne metathesis.
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