Abstract

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.

Highlights

  • Around the reservoir for domestic water in Chinese rural areas, a folk medicinal soil in a dark and moist environment is used to prevent infection and accelerating cure by being spread around the wound after dog bite

  • The 13C and 1H assignments of 1 were achieved through the analyses of nuclear magnetic resonance (NMR) data. 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

  • Assigned to many methylene carbons confirmed by its distortionless enhancement by polarization transfer (Dept) 135 ̊ and heteronuclear single-quantum correlation (HSQC) spectra, a large peak at 29.26 - 29.95 ppm in its 13C NMR and a corresponding peak at 1.20 - 1.36 ppm in its 1H NMR indicated that 1 was likely a fatty acid ester [3] [9]

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Summary

Introduction

Around the reservoir for domestic water in Chinese rural areas, a folk medicinal soil in a dark and moist environment is used to prevent infection and accelerating cure by being spread around the wound after dog bite. To reveal the anti-infection reasons of this soil, a sample was collected in Xianjing Countryside in Zhuzhou County, China, and sixty-one actinomycete strains ZZ01 to ZZ061. After chemical analysis were performed for discovering strains producing a series of secondary metabolites, the bioactive evaluation showed that thirteen strains had antimicrobial activities against Staphylococcus aureus, Escherichia coli and/or Candida albicans, and the classification and identification of targeted seven strains indicated that they belonged to the genus Streptomyces [2]. ZZ035 with remarkable antimicrobial activities against S. aureus, E. coli and C. albicans was targeted for discovering antimicrobial metabolites. During the isolation of components from the broth of this strain, a white crystal powder was isolated and identified as triglycerides, and many nuclear magnetic resonance (NMR) data including 1H, 13C, distortionless enhancement by polarization transfer (Dept), heteronuclear single-quantum correlation (HSQC), 1H-1H correlation spectroscopy (1H-1H COSY) and heteronuclear multiple-bond correlation (HMBC) were obtained for the structural analyses of these triglycerides

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