Biotransformation of terpene and terpenoid derivatives by Aspergillus niger NRRL 326

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ORIGINAL ARTICLE

Biotransformation of terpene and terpenoid derivatives by Aspergillus niger NRRL 326 Cengiz Çorbacı 1 Received: 13 March 2019 / Accepted: 17 February 2020 # Institute of Molecular Biology, Slovak Academy of Sciences 2020

Abstract Natural products are chemicals used in many industrial processes due to their various pharmacological or biological actions. Microorganisms can catalyze reactions that allow modification of structures of phytochemicals and organic compounds. Hereby, it is possible to obtain valuable products with regio- and stereo-selective reactions. The aim of the paper was to biotransform several terpenes and terpenoids including (−)-α-pinene, β-ionone and isophorone by using A. niger NRRL 326 and to determine their biotransformation products and biological activities. According to the GC-MS analysis, the following compounds were obtained: (S)-(+)-carvone hydrate (4.28%) from (−)-α-pinene; 4-hydroxybetaionone (48.33%), 2-hydroxybetaionone (22.40%), α-ionone (1.29%) and dihydro-3-oxo-beta-ionol (1.11%) from β-ionone; 4-hydroxyisophorone (55.54%), 3,3-dimethyl-5-oxocyclohexanecarboxaldehyde (1.87%), 4-ketoisophorone (1.22%) and dihydrooxoisophorone (0.59%) from isophorone. The biological activities of the extracts were found to be slightly higher than the control experiments. The findings obtained will contribute to the literature and A. niger NRRL 326 have the potential to become an important biotransformation agent. Keywords A. niger . Antimicrobial . Antioxidant . Biotransformation . GC-MS . Terpenes

Abbreviations ABTS 2,2′-azinobis-3-ethylbenzothiazoline6-sulfonic acid A. niger Aspergillus niger B.c Bacillus cereus RSKK 709 C.a Candida albicans ATCC 10231 DMSO Dimethyl sulfoxide DPPH 1,1-diphenyl-2-picrylhydrazyl EI Electron ionization EtOAc Ethyl acetate GC-MS Gas chromatography-mass spectrometer K2S2O8 Potassium persulfate MHA Mueller hinton agar MHB Mueller hinton broth MIC Minimum inhibitor concentration MRSA Methicillin resistant Staphylococcus aureus Na2SO4 Anhydrous sodium sulfate nd Not determined

* Cengiz Çorbacı [email protected] 1

Department of Genetics and Bioengineering, Faculty of Engineering, Giresun University, 28200 Giresun, Turkey

P.a PDA S.a TEAC TIC TLC w YM

Pseudomonas aeruginosa ATCC 27853 Potato dextrose agar methicillin resistant Staphylococcus aureus (MRSA) ATCC 43300 Trolox equivalent antioxidant capacity Total ion chromatogram Thin layer chromatography Weak Yeast malt

Introduction Natural products are known as chemical compounds or substances produced by an organism found in nature. In a broader sense, these products can be defined as any compound provided by life. They are interesting metabolites and can also be obtained by chemical synthesis, and in some cases, may have pharmacological or biological activities with therapeutic benefits in the treatment of diseases. Thus, they are effective ingredients not only for conventional medicines but also for modern drugs (Cutler and Cutler 1999; Samuelson 1999). In recent years, the recognition