Abstract

Three new compounds of the malyngamide series, 6,8-di-O-acetylmalyngamide 2 (1), 6-O-acetylmalyngamide 2 (2), and N-demethyl-isomalyngamide I (3), were isolated from the marine cyanobacterium Moorea producens. Their structures were determined by spectroscopic analysis and chemical derivatization and degradation. These compounds stimulated glucose uptake in cultured L6 myotubes. In particular, 6,8-di-O-acetylmalyngamide 2 (1) showed potent activity and activated adenosine monophosphate-activated protein kinase (AMPK).

Highlights

  • The ocean covers more than 70% of the Earth’s surface and hosts huge biological and chemical diversity

  • The malyngamide series of natural products have been isolated from various marine filamentous cyanobacteria

  • As part of our ongoing effort to identify novel bioactive natural products, we have focused on the constituents of marine cyanobacteria and isolated odoamide [9,10] and odobromoamide [11]

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Summary

Introduction

The ocean covers more than 70% of the Earth’s surface and hosts huge biological and chemical diversity. Because marine environmental conditions are quite different from terrestrial ones, natural products from marine organisms have unique structures and biological activities. Bisebromoamide, isolated from Lyngbya sp., showed potent cytotoxicity against HeLa S3 cells [4]. The malyngamide series of natural products have been isolated from various marine filamentous cyanobacteria. A, the first compound of this group, was isolated from Lyngbya majuscule in 1979 [7]; since over 30 malyngamide analogs have been isolated [8]. As part of our ongoing effort to identify novel bioactive natural products, we have focused on the constituents of marine cyanobacteria and isolated odoamide [9,10] and odobromoamide [11]. We report the isolation, structure determination, and biological evaluation of these compounds.

Results
Partial
H NMR configuration at the
H-7 H-9 andwere
Biological
General Experimental Procedures
Identification of the Marine Cyanobacterium
Preparation of MTPA Esters of 2
Preparation of Acetylated Compound 2
Base Hydrolysis of Compounds 2 and 3
Culture of L6 Myoblasts
Determination of Glucose Uptake
3.10. Western Blotting
Conclusions
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