Biological Evaluations, NMR Analyses, Molecular Modeling Studies, and Overview of the Synthesis of the Marine Natural Product (-)-Mucosin.

Autor: Nolsøe JMJ; Faculty of Chemistry, Biotechnology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, NO-1433 Ås, Norway.; Faculty of Biosciences and Aquaculture, Nord University, P.O. Box 1490, NO-8049 Bodø, Norway., Underhaug J; Department of Chemistry, University of Bergen, Allégaten 41, NO-5007 Bergen, Norway., Sørskar ÅM; Department of Pharmacy, Section for Pharmaceutical Chemistry, University of Oslo, P.O. Box 1068, NO-0316 Oslo, Norway., Antonsen SG; Department of Mechanical, Electronic and Chemical Engineering, Faculty of Technology, Art and Design, Oslo Metropolitan University, NO-0130 Oslo, Norway., Malterud KE; Department of Pharmacy, Section for Pharmaceutical Chemistry, University of Oslo, P.O. Box 1068, NO-0316 Oslo, Norway., Gani O; Department of Pharmacy, Section for Pharmaceutical Chemistry, University of Oslo, P.O. Box 1068, NO-0316 Oslo, Norway., Fan Q; Department of Molecular Medicine, Institute of Basic Medical Sciences, Faculty of Medicine, University of Oslo, NO-0317 Oslo, Norway., Hjorth M; Department of Molecular Medicine, Institute of Basic Medical Sciences, Faculty of Medicine, University of Oslo, NO-0317 Oslo, Norway., Sæther T; Department of Molecular Medicine, Institute of Basic Medical Sciences, Faculty of Medicine, University of Oslo, NO-0317 Oslo, Norway., Hansen TV; Faculty of Chemistry, Biotechnology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, NO-1433 Ås, Norway.; Department of Pharmacy, Section for Pharmaceutical Chemistry, University of Oslo, P.O. Box 1068, NO-0316 Oslo, Norway., Stenstrøm YH; Faculty of Chemistry, Biotechnology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, NO-1433 Ås, Norway.; Department of Mechanical, Electronic and Chemical Engineering, Faculty of Technology, Art and Design, Oslo Metropolitan University, NO-0130 Oslo, Norway.
Jazyk: angličtina
Zdroj: Molecules (Basel, Switzerland) [Molecules] 2024 Feb 24; Vol. 29 (5). Date of Electronic Publication: 2024 Feb 24.
DOI: 10.3390/molecules29050994
Abstrakt: Natural products obtained from marine organisms continue to be a rich source of novel structural architecture and of importance in drug discovery, medicine, and health. However, the success of such endeavors depends on the exact structural elucidation and access to sufficient material, often by stereoselective total synthesis, of the isolated natural product of interest. (-)-Mucosin ( 1 ), a fatty acid derivative, previously presumed to contain a rare cis -bicyclo[4.3.0]non-3-ene moiety, has since been shown to be the trans -congener. Analytically, the fused bicyclic ring system in (-)- 1 constitutes a particular challenge in order to establish its relative and absolute stereochemistry. Herein, data from biological evaluations, NMR and molecular modeling studies of (-)- 1 are presented. An overview of the synthetic strategies enabling the exact structural elucidation of (-)-mucosin ( 1 ) is also presented.
Databáze: MEDLINE
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