Literature DB >> 20166701

Isolation and biological evaluation of 8-epi-malyngamide C from the Floridian marine cyanobacterium Lyngbya majuscula.

Jason C Kwan1, Max Teplitski, Sarath P Gunasekera, Valerie J Paul, Hendrik Luesch.   

Abstract

A new stereoisomer of malyngamide C, 8-epi-malyngamide C (1), and the known compound lyngbic acid [(4E,7S)-7-methoxytetradec-4-enoic acid] were isolated from a sample of Lyngbya majuscula collected near Bush Key, Dry Tortugas, Florida. The structure of 1 was determined by NMR and MS experiments. The absolute configuration of 1 was determined by selective Mitsunobu inversion of C-8 to give malyngamide C, as determined by NMR, MS, and comparison of specific rotation. Both 1 and malyngamide C were found to be cytotoxic to HT29 colon cancer cells (IC(50) 15.4 and 5.2 microM, respectively) and to inhibit bacterial quorum sensing in a reporter gene assay.

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Year:  2010        PMID： 20166701      PMCID： PMC2846190          DOI： 10.1021/np900614n

Source DB:  PubMed          Journal:  J Nat Prod        ISSN： 0163-3864            Impact factor:   4.050


  16 in total

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Authors:  W A Gallimore; P J Scheuer
Journal:  J Nat Prod       Date:  2000-10       Impact factor: 4.050

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Journal:  J Nat Prod       Date:  2000-07       Impact factor: 4.050

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Review 4.  Bacterial quorum sensing and interference by naturally occurring biomimics.

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Journal:  Anal Bioanal Chem       Date:  2006-09-26       Impact factor: 4.142

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Journal:  J Nat Prod       Date:  1995-05       Impact factor: 4.050

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Review 6.  Marine natural product peptides with therapeutic potential: Chemistry, biosynthesis, and pharmacology.

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7.  Lyngbyoic acid, a "tagged" fatty acid from a marine cyanobacterium, disrupts quorum sensing in Pseudomonas aeruginosa.

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8.  Two cytotoxic stereoisomers of malyngamide C, 8-epi-malyngamide C and 8-O-acetyl-8-epi-malyngamide C, from the marine cyanobacterium Lyngbya majuscula.

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