Microbial Transformation of 3,3-Dimethylcyclohexyl methyl ketone and Antimicrobial Evaluation

Abstract

3,3-Dimethylcyclohexyl methyl ketone (Herbac®) is a fine fragrance compound used in the cosmetic industry. In this study, the biological derivatisation of the substrate 3,3-dimethylcyclohexyl methyl ketone by 18 fungal cultures was carried out to obtain new derivatives. Among the evaluated, the plant fungus Aspergillus niger ATCC 10549, biotransformed the substrate to the 4-hydroxy derivative in 19% yield. The structure was determined by using NMR and GC-MS spectroscopic methods. In addition, the antimicrobial activity of Herbac® with the metabolite against a panel of pathogenic microbial strains were evaluated using in vitro microdilution. The results showed that the metabolite was relatively more susceptible compared to the substrate Herbac®.

Keywords

• antimicrobial activity
• Aspergillus niger
• Biotransformation
• Fragrance compounds

References

1. M.A. Longo, M.A. Sanroman, Production of food aroma compounds: microbial and enzymatic methodologies, Food Technol. Biotechnol., 44 (2006) 335-353.
2. A. Rayar, R. Manivannan, In Vitro Alpha-Amylase and Alpha-Glucosidase Inhibition Activity of Umbelliferone and Beta-Ionone Isolated from Coriandrum sativum Linn., World J. Pharm. Pharm. Sci., 5 (2016) 1280-1289.
3. J.P. Horst Surburg, Common Fragrance and Flavor Materials: Preparation, Properties and Uses. Individual Fragrance and Flavor Materials. Wiley‐VCH Verlag GmbH & Co. KGaA, 2009.
4. P. Kraft, Perspectives in Flavor and Fragrance Research. The Search for New Fragrance Ingredients for Functional Perfumery, 2005.
5. J. Scognamiglio, C.S. Letizia, A.M. Api, Fragrance material review on 1-(3,3-dimethylcyclohexyl)ethan-1-one. Food Chem. Toxicol.,62 (2013) 56-60.
6. J. Liu, Q. Zhang, P. Li, Z. Qu, S. Sun, Y. Ma, D. Su, Y. Zong, J. Zhang, Six-Membered Silacycle Odorants: Synthesis and Olfactory Characterization of Si Analogues of Artemone, β-Dynascone, and Herbac. Eur J. Inorg. Chem.,21 (2014) 3435-3440.
7. Z. Jiang, C. Kempinski, J. Chappell, Extraction and Analysis of Terpenes/Terpenoids. Curr. Protoc. Plant Biol., 1 (2016) 345-358.
8. Ö. Özşen Batur, İ. Kiran, F. Demirci, K.H.C. Başer, Fungal biotransformation of cedramber, Biocatal. Biotransformation, 40 (2021) 1-4.

9. M27-A2, Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeast Approved Standard, Second Edition. vol 22. Clinical and Laboratory Standards Institute (CLSI) [formerly NCCLS], Wayne, Pennsylvani, USA, 2002.
10. M38-A2, Reference Method for Broth Dilution Antifungal Susceptibility Testing of Flamentous Fungi, Approved Standard, Second Edition. vol 22. Clinical and Laboratory Standards Institute (CLSI) [formerly NCCLS], Wayne, Pennsylvani, USA, 2008.
11. M100-S16, Performance Standards for Antimicrobial Susceptibility Testing, Sixteenth Informational Supplement. vol 26. Clinical and Laboratory Standards Institute (CLSI) [formerly NCCLS], Wayne, Pennsylvani, USA, 2006.
12. Ö. Özşen, İ. Kıran, İ. Dağ, Ö. Atlı, G.A. Çiftçi, F. Demirci, Biotransformation of abietic acid by fungi and biological evaluation of its metabolites, Process Biochem., 52 (2017), 130-140.
13. I. Kiran , O. Ozsen, K.H. Can Baser, F. Demirci, Fungal Biotransformation of Cyclademol and Antimicrobial Activities of Its Metabolites, Nat. Prod. Commun., 12 (2017) 1529-1530.