Streptomyces sp. ZZ035 isolated from a folk medicinal soil sample in China showed remarkable antimicrobial activities. During the isolation of secondary metabolites, a white crystal powder (1) was isolated from the broth of this strain. Its nuclear magnetic resonance (NMR) and infrared (IR) spectra indicated that it was a complex composed of triglycerides. Next, six C15-17 long- chain fatty acids derived from these triglycerides were respectively identified as n-pentadecanoyl, 12-methyltetradecanoyl, 14-methyl pentadecanoyl, palmitoyl, 15-methyl hexadecanoyl and 14-methyl hexadecanoyl using the gas chromatography-mass spectroscopy (GC-MS) technology. Finally, the 13C and 1H assignments of 1 were achieved through the analyses of NMR data. Based on above, their detailed NMR spectroscopic elucidation and meticulous 13C, 1H assignments, especially the split peaks and coupling correlation of protons attached on the glycerol carbons, were performed for distinguishing triglycerides from other glycerides and for the identification of the long-chain fatty acids, and which would be helpful to the qualitative and quantitative analyses of tri-, di-and mono-glycerides.
References
[1]
Yuan, G., Li, P., Yang, H., Wu, X., Tu, G. and Wei, S. (2012) Chemical Screening of Sixty-One Actinomycete Strains and Anti-Methicillin-Resistant Staphylococcus aureus Assays of Target Strains. Chinese Journal of Natural Medicine, 10, 155-160.
https://doi.org/10.3724/SP.J.1009.2012.00155
[2]
Xu, X., Wu, X., Yuan, G., Zhong, Q. and Xu, L. (2017) A New Inhibitor of γ-Aminobutric Acid Aminotransferase from Streptomyces sp. ZZ035 Isolated from a Folk Medicinal Soil in China.
[3]
Nieva-Echevarría, B., Goicoechea, E., Manzanos, M.J. and Guillén, M.D. (2016) A Study by 1H NMR on the Influence of Some Factors Affecting Lipid in Vitro Digestion. Food Chemistry, 211, 17-26.
[4]
Nieva-Echevarría, B., Goicoechea, E., Manzanos, M.J. and Guillén, M.D. (2015) Usefulness of 1H NMR in Assessing the Extent of Lipid Digestion. Food Chemistry, 179, 182-190.
[5]
Nieva-Echevarría, B., Goicoechea, E., Manzanos, M.J. and Guillén, M.D. (2014) A Method Based on 1H NMR Spectral Data Useful to Evaluate the Hydrolysis Level in Complex Lipid Mixtures. Food Research International, 66, 379-387.
[6]
Sopelana, P., Arizabaleta, I., Ibargoitia, M.L. and Guillén, M.D. (2013) Characterisation of the Lipidic Components of Margarines by 1H Nuclear Magnetic Resonance. Food Chemistry, 141, 3357-3364.
[7]
Lu, Y., Wang, J., Deng, Z., Wu, H., Deng, Q., Tan, H. and Cao, L. (2013) Isolation and Characterization of Fatty Acid Methyl Ester (FAME)-Producing Streptomyces sp. S161 from Sheep (Ovis aries) Faeces. Letters in Applied Microbiology, 57, 200- 205.
https://doi.org/10.1111/lam.12096
[8]
Akeda, Y., Shibata, K., Ping, X., Tanaka, T. and Taniguchi, M. (1995) AKD-2A, B, C and D, New Antibiotics from Streptomyces sp. OCU-42815: Taxonomy, Fermentation, Isolation, Structure Elucidation and Biological Activity. Journal of Antibiotics, 48, 363-368.
https://doi.org/10.7164/antibiotics.48.363
[9]
Serdarevich, B. and Carroll, K.K. (1966) Synthesis and Characterization of 1- and 2-Monoglycerides of anteiso Fatty Acids. Journal of Lipid Research, 7, 277-284.
[10]
Parkash, S. and Blanshard, J.M.V. (1975) Infrared Spectra of Selected Ultra-Pure Triglycerides. Spectrochimica Acta Part A: Molecular Spectroscopy, 31, 951-957.
[11]
Omura, S., Nakagawa, A., Fukamachi, N., Otoguro, K. and Kobayashi, B. (1986) Aggreceride, a New Platelet Aggregation Inhibitor from Streptomyces. Journal of Antibiotics, 34, 1180-1181.
https://doi.org/10.7164/antibiotics.39.1180
[12]
Kim, Y.A., Park, M.S., Kim, Y.H. and Han, S. (2003) Synthesis of 1-lyso-2-Palmitoyl- rac-glycero-3-phosphocholine and Its Regioisomers and Structural Elucidation by NMR Spectroscopy and FAB Tandem Mass Spectrometry. Tetrahedron, 59, 2921- 2928.
[13]
Mechoulam, R., Ben-Shabat, S., Hanus, L., Ligumsky, M., Kaminski, N.E., Schatz, A.R., Gopher, A., Almog, S., Martin, B.R., Compton, D.R., Pertwee, R.G., Griffin, G., Bayewitch, M., Barg, J. and Vogel, Z. (1995) Identification of an Endogenous 2-Monoglyceride, Present in Canine Gut, That Binds to Cannabinoid Receptors. Biochemical Pharmacology, 50, 83-90.
[14]
Aizpurua-Olaizola, O., Elezgarai, I., Rico-Barrio, I., Zarandona, I., Etxebarria, N. and Usobiaga, A. (2016) Targeting the Endocannabinoid System: Future Therapeutic Strategies. Drug Discovery Today, 22, 105-110.
[15]
Konishi, T., Satsu, H., Hatsugai, Y., Aizawa, K., Inakuma, T., Nagata, S., Sakuda, S., Nagasawa, H. and Shimizu, M. (2004) A Bitter Melon Extract Inhibits the P-Gly- coprotein Activity in Intestinal Caco-2 Cells: Monoglyceride as an Active Compound. BioFactors, 22, 71-74.
https://doi.org/10.1002/biof.5520220113
[16]
Almoselhy, R.I.M., Allam, M.H., El-Kalyoubi, M.H. and El-Sharkawy, A.A. (2014) 1H NMR Spectral Analysis as a New Aspect to Evaluate the Stability of Some Edible Oils. Annals of Agricultural Science, 59, 201-206.
[17]
Gunstone, F.D. (1991) 13C-NMR Studies of Mono-, Di- and Triacylglycerols Leading to Qualitative and Semiquantitative Information about Mixtures of These Glycerol Esters. Chemistry and Physics of Lipids, 58, 219-224.
