Efficient and selective catalytic hydroxylation of unsaturated plant oils: a novel method for producing anti-pathogens

Ahmed M Senan; Binru Yin; Yaoyao Zhang; Mustapha M Nasiru; Yong-Mei Lyu; Muhammad Umair; Javaid A Bhat; Sicheng Zhang; Li Liu

doi:10.1186/s13065-021-00748-z

Efficient and selective catalytic hydroxylation of unsaturated plant oils: a novel method for producing anti-pathogens

BMC Chem. 2021 Mar 29;15(1):20. doi: 10.1186/s13065-021-00748-z.

Authors

Ahmed M Senan^{1

2}, Binru Yin³, Yaoyao Zhang³, Mustapha M Nasiru³, Yong-Mei Lyu³, Muhammad Umair³, Javaid A Bhat³, Sicheng Zhang⁴, Li Liu^{5

6}

Affiliations

¹ Glycomics and Glycan Bioengineering Research Center School of Food Science and Technology, Nanjing Agricultural University, Nanjing, 210095, People's Republic of China. ahmedmsenan@njau.edu.cn.
² Department of Pharmaceutical Sciences, College of Pharmacy, University of Tennessee Health Science Center, Memphis, TN, 38163, USA. ahmedmsenan@njau.edu.cn.
³ Glycomics and Glycan Bioengineering Research Center School of Food Science and Technology, Nanjing Agricultural University, Nanjing, 210095, People's Republic of China.
⁴ Department of Pharmaceutical Sciences, College of Pharmacy, University of Tennessee Health Science Center, Memphis, TN, 38163, USA.
⁵ Glycomics and Glycan Bioengineering Research Center School of Food Science and Technology, Nanjing Agricultural University, Nanjing, 210095, People's Republic of China. lichen.liu@njau.edu.cn.
⁶ Department of Pharmaceutical Sciences, College of Pharmacy, University of Tennessee Health Science Center, Memphis, TN, 38163, USA. lichen.liu@njau.edu.cn.

Abstract

With the increasing demand for antimicrobial agents and the spread of antibiotic resistance in pathogens, the exploitation of plant oils to partly replace antibiotic emerges as an important source of fine chemicals, functional food utility and pharmaceutical industries. This work introduces a novel catalytic method of plant oils hydroxylation by Fe(III) citrate monohydrate (Fe³⁺-cit.)/Na₂S₂O₈ catalyst. Methyl (9Z,12Z)-octadecadienoate (ML) was selected as an example of vegetable oils hydroxylation to its hydroxy-conjugated derivatives (CHML) in the presence of a new complex of Fe(II)-species. Methyl 9,12-di-hydroxyoctadecanoate 1, methyl-9-hydroxyoctadecanoate 2 and methyl (10E,12E)-octadecanoate 3 mixtures is produced under optimized condition with oxygen balloon. The specific hydroxylation activity was lower in the case of using Na₂S₂O₈ alone as a catalyst. A chemical reaction has shown the main process converted of plantoils hydroxylation and (+ 16 Da) of OH- attached at the methyl linoleate (ML-OH). HPLC and MALDI-ToF-mass spectrometry were employed for determining the obtained products. It was found that adding oxidizing agents (Na₂S₂O₈) to Fe³⁺ in the MeCN mixture with H₂O would generate the new complex of Fe(II)-species, which improves the C-H activation. Hence, the present study demonstrated a new functional method for better usage of vegetable oils.Producing conjugated hydroxy-fatty acids/esters with better antipathogenic properties. CHML used in food industry, It has a potential pathway to food safety and packaging process with good advantages, fundamental to microbial resistance. Lastly, our findings showed that biological monitoring of CHML-minimum inhibitory concentration (MIC) inhibited growth of various gram-positive and gram-negative bacteria in vitro study. The produced CHML profiles were comparable to the corresponding to previousstudies and showed improved the inhibition efficiency over the respective kanamycin derivatives.

Keywords: Anti-pathogens; Catalyst; Functional method; Growth-inhibition; Hydroxy-fatty acids/esters.

Abstract

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