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Chemical Compound Review:

Sarcinic acid 12-methyltetradecanoic acid

Synonyms: AGN-PC-00S4RX, CHEMBL495852, CHEBI:39251, M3664_SIGMA, AC1L2ITY, ...

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Disease relevance of Sarcinic acid

Here we study 12-methyltetradecanoic acid (12-MTA), a branched-chain fatty acid, isolated from a sea cucumber extract, on the growth of prostate cancer cells and investigate the underlying mechanisms of its effect [1].
The iso/anteiso pair, 13-methyltetradecanoic acid and 12-methyltetradecanoic acid, were the principal fatty acids in the gram positive cocci, and the 9- and 11-hexadecenoic acids were particularly abundant in V. parahaemolyticus [2].
The purpose of this research was to evaluate the effects of targeted arterial delivery of the branched chain fatty acid 12-methyltetradecanoic acid (12-MTA) on the VX2 squamous cell carcinoma in rabbits [3].

High impact information on Sarcinic acid

Inhibition of proliferation of PC3 cells by the branched-chain fatty acid, 12-methyltetradecanoic acid, is associated with inhibition of 5-lipoxygenase [1].
The marine strain Bacillus pumilus strain AAS3, isolated from the Mediterranean sponge Acanthella acuta, produced a diglucosyl-glycerolipid, 1,2-O-diacyl-3-[beta-glucopyranosyl-(1-6)-beta-glucopyranosyl)]glycerol, with 14-methylhexadecanoic acid and 12-methyltetradecanoic acid as the main fatty acid moieties (GGL11) [4].
One of them, DMI-4 was distinguished from DMI-1, -2 and -3 previously reported with respect to certain properties, DMI-4 is considered to be a triglyceride consisting of the fatty acids anteisopentadecanoic acid (C15:0), isopalmitic acid (C16:0) and isostearic acid (C18:0) from the results of gas chromatography analysis [5].
This was in contrast to results with aseanostatin P5 which selectively inhibited FMLP-induced MPO release [6].
Solid state NMR spectra of dimyristoylphosphatidylcholine (DMPC) lipid membranes containing either free 12-methyltetradecanoic acid (a15:0) or free 13-methyltetradecanoic acid (i15:0), show significant differences in their impact on the lipid bilayer [7].

Biological context of Sarcinic acid

Two components P1 and P5 with the IC50 of 0.96 and 0.54 microgram/ml to the MPO release were obtained as pure forms, indicating aseanostatin P5 was higher activity than aseanostatin P1 [8].

Anatomical context of Sarcinic acid

Both the enantiomers of aseanostatin P5 (sarcinic acid), an inhibitor of myeloperoxidase (MPO) release from human polymorphonuclear leukocytes (PMN), with high optical purity were synthesized by starting from (S)-2-methylbutanol and methyl (S)-3-hydroxy-2-methylpropanoate [9].

References

Inhibition of proliferation of PC3 cells by the branched-chain fatty acid, 12-methyltetradecanoic acid, is associated with inhibition of 5-lipoxygenase. Yang, P., Collin, P., Madden, T., Chan, D., Sweeney-Gotsch, B., McConkey, D., Newman, R.A. Prostate (2003) [Pubmed]
Comparison of the fatty acids of the tunicate Botryllus schlosseri from the Black Sea with two associated bacterial strains. Carballeira, N.M., Shalabi, F., Stefanov, K., Dimitrov, K., Popov, S., Kujumgiev, A., Andreev, S. Lipids (1995) [Pubmed]
Evaluation of targeted arterial delivery of the branched chain fatty acid 12-methyltetradecanoic acid as a novel therapy for solid tumors. Wright, K.C., Yang, P., Van Pelt, C.S., Hicks, M.E., Collin, P., Newman, R.A. J. Exp. Ther. Oncol. (2005) [Pubmed]
Diglucosyl-glycerolipids from the marine sponge-associated Bacillus pumilus strain AAS3: their production, enzymatic modification and properties. Ramm, W., Schatton, W., Wagner-Döbler, I., Wray, V., Nimtz, M., Tokuda, H., Enjyo, F., Nishino, H., Beil, W., Heckmann, R., Lurtz, V., Lang, S. Appl. Microbiol. Biotechnol. (2004) [Pubmed]
Inhibition of DNA methyltransferase by microbial inhibitors and fatty acids. Suzuki, K., Nagao, K., Tokunaga, J., Katayama, N., Uyeda, M. J. Enzym. Inhib. (1996) [Pubmed]
Pyrrolomycin group antibiotics inhibit substance P-induced release of myeloperoxidase from human polymorphonuclear leukocytes. Masuda, K., Suzuki, K., Ishida-Okawara, A., Mizuno, S., Hotta, K., Miyadoh, S., Hara, O., Koyama, M. J. Antibiot. (1991) [Pubmed]
Impact on lipid membrane organization by free branched-chain fatty acids. Lindstr??m, F., Thurnhofer, S., Vetter, W., Gr??bner, G. Physical chemistry chemical physics : PCCP. (2006) [Pubmed]
Purification and characterization of aseanostatins: actinomycete-derived fatty acid inhibitors to myeloperoxidase release from human polymorphonuclear leukocytes. Ishida-Okawara, A., Kimoto, Y., Watanabe, K., Tokuda, K., Shibata, M., Masuda, K., Takano, Y., Kawaguchi, K., Akagawa, H., Nilubol, N. J. Antibiot. (1991) [Pubmed]
Synthesis of both the enantiomers of aseanostatin P5 (sarcinic acid), an inhibitor of myeloperoxidase release, and four diastereomers of aggreceride A, a platelet aggregation inhibitor. Kitahara, T., Aono, S., Mori, K. Biosci. Biotechnol. Biochem. (1995) [Pubmed]

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