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2-Methoxylated fatty acids in marine sponges: Defense mechanism against mycobacteria?

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Lipids

Abstract

A series of saturated 2-methoxylated FA having even-numbered chains with 8–14 carbons were synthesized, and their spectroscopic data are presented for the first time. The 2-methoxylated C10−C14 acids were prepared from the corresponding 2-hydroxylated FA, whereas the 2-methoxyoctanoic acid was synthesized starting with heptaldehyde. All of the methoxylated FA displayed some degree of inhibition (between 2 and 99%) of Mycobacterium tuberculosis H37Rv at 6.25 μg/mL. The most inhibitory FA was 2-methoxydecanoic acid, with a minimum inhibitory concentration of 200–239 μM against M. tuberculosis H37Rv as determined by both the microplate Alamar Blue assay and the green fluorescent protein microplate assay. These results are discussed in terms of the possible role of the 2-methoxylated FA as antimicrobial lipids produced either by marine sponges, or the associated marine symbiotic bacteria, as a defense mechanism in a highly competitive environment.

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Abbreviations

FU:

fluorescence units

GFPMA:

green fluorescent protein microplate assay

MABA:

microplate Alamar Blue assay

MIC:

minimum inhibitory concentration

OADC:

oleic acid, albumin, dextrose, catalase

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Author information

Authors and Affiliations

  1. Tuberculosis Antimicrobial Acquisition & Coordinating Facility, 35255-5305, Birmingham, Alabama

    Cecil D. Kwong

  2. Institute for Tuberculosis Research, College of Pharmacy, The University of Illinois at Chicago, 60612-7231, Chicago, Illinois

    Baojie Wan & Scott Franzblau

  3. Department of Chemistry, University of Puerto Rico, P.O. Box 23346, 00931-3346, San Juan, Puerto Rice

    Néstor M. Carballeira & Heindyleen Cruz

Authors
  1. Néstor M. Carballeira
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  2. Heindyleen Cruz
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  3. Cecil D. Kwong
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  4. Baojie Wan
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  5. Scott Franzblau
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Corresponding author

Correspondence to Néstor M. Carballeira.

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Carballeira, N.M., Cruz, H., Kwong, C.D. et al. 2-Methoxylated fatty acids in marine sponges: Defense mechanism against mycobacteria?. Lipids 39, 675–680 (2004). https://doi.org/10.1007/s11745-004-1281-8

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  • DOI: https://doi.org/10.1007/s11745-004-1281-8

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