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

Year 2022, , 263 - 267, 01.08.2022
https://doi.org/10.15671/hjbc.982977

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®.

Supporting Institution

Scientific and Technological Research Council of Turkey

Project Number

TEYDEB- 7110249

Thanks

Financial support from the Scientific and Technological Research Council of Turkey (Grant no: TEYDEB- 7110249) is kindly acknowledged. The authors express their thamks to International Flavors & Fragrances (IFF) Co., USA for providing HERBAC and Badebio Biotechnology Ltd. its infrastructure.

References

  • M.A. Longo, M.A. Sanroman, Production of food aroma compounds: microbial and enzymatic methodologies, Food Technol. Biotechnol., 44 (2006) 335-353.
  • 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.
  • 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.
  • P. Kraft, Perspectives in Flavor and Fragrance Research. The Search for New Fragrance Ingredients for Functional Perfumery, 2005.
  • 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.
  • 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.
  • Z. Jiang, C. Kempinski, J. Chappell, Extraction and Analysis of Terpenes/Terpenoids. Curr. Protoc. Plant Biol., 1 (2016) 345-358.
  • Ö. Özşen Batur, İ. Kiran, F. Demirci, K.H.C. Başer, Fungal biotransformation of cedramber, Biocatal. Biotransformation, 40 (2021) 1-4.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
Year 2022, , 263 - 267, 01.08.2022
https://doi.org/10.15671/hjbc.982977

Abstract

Project Number

TEYDEB- 7110249

References

  • M.A. Longo, M.A. Sanroman, Production of food aroma compounds: microbial and enzymatic methodologies, Food Technol. Biotechnol., 44 (2006) 335-353.
  • 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.
  • 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.
  • P. Kraft, Perspectives in Flavor and Fragrance Research. The Search for New Fragrance Ingredients for Functional Perfumery, 2005.
  • 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.
  • 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.
  • Z. Jiang, C. Kempinski, J. Chappell, Extraction and Analysis of Terpenes/Terpenoids. Curr. Protoc. Plant Biol., 1 (2016) 345-358.
  • Ö. Özşen Batur, İ. Kiran, F. Demirci, K.H.C. Başer, Fungal biotransformation of cedramber, Biocatal. Biotransformation, 40 (2021) 1-4.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
There are 13 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Research Article
Authors

Özge Özşen Batur 0000-0002-6908-1174

İsmail Kıran 0000-0003-4929-9341

Kemal Başer 0000-0003-2710-0231

Fatih Demirci 0000-0003-1497-3017

Project Number TEYDEB- 7110249
Publication Date August 1, 2022
Acceptance Date March 14, 2022
Published in Issue Year 2022

Cite

APA Özşen Batur, Ö., Kıran, İ., Başer, K., Demirci, F. (2022). Microbial Transformation of 3,3-Dimethylcyclohexyl methyl ketone and Antimicrobial Evaluation. Hacettepe Journal of Biology and Chemistry, 50(3), 263-267. https://doi.org/10.15671/hjbc.982977
AMA Özşen Batur Ö, Kıran İ, Başer K, Demirci F. Microbial Transformation of 3,3-Dimethylcyclohexyl methyl ketone and Antimicrobial Evaluation. HJBC. August 2022;50(3):263-267. doi:10.15671/hjbc.982977
Chicago Özşen Batur, Özge, İsmail Kıran, Kemal Başer, and Fatih Demirci. “Microbial Transformation of 3,3-Dimethylcyclohexyl Methyl Ketone and Antimicrobial Evaluation”. Hacettepe Journal of Biology and Chemistry 50, no. 3 (August 2022): 263-67. https://doi.org/10.15671/hjbc.982977.
EndNote Özşen Batur Ö, Kıran İ, Başer K, Demirci F (August 1, 2022) Microbial Transformation of 3,3-Dimethylcyclohexyl methyl ketone and Antimicrobial Evaluation. Hacettepe Journal of Biology and Chemistry 50 3 263–267.
IEEE Ö. Özşen Batur, İ. Kıran, K. Başer, and F. Demirci, “Microbial Transformation of 3,3-Dimethylcyclohexyl methyl ketone and Antimicrobial Evaluation”, HJBC, vol. 50, no. 3, pp. 263–267, 2022, doi: 10.15671/hjbc.982977.
ISNAD Özşen Batur, Özge et al. “Microbial Transformation of 3,3-Dimethylcyclohexyl Methyl Ketone and Antimicrobial Evaluation”. Hacettepe Journal of Biology and Chemistry 50/3 (August 2022), 263-267. https://doi.org/10.15671/hjbc.982977.
JAMA Özşen Batur Ö, Kıran İ, Başer K, Demirci F. Microbial Transformation of 3,3-Dimethylcyclohexyl methyl ketone and Antimicrobial Evaluation. HJBC. 2022;50:263–267.
MLA Özşen Batur, Özge et al. “Microbial Transformation of 3,3-Dimethylcyclohexyl Methyl Ketone and Antimicrobial Evaluation”. Hacettepe Journal of Biology and Chemistry, vol. 50, no. 3, 2022, pp. 263-7, doi:10.15671/hjbc.982977.
Vancouver Özşen Batur Ö, Kıran İ, Başer K, Demirci F. Microbial Transformation of 3,3-Dimethylcyclohexyl methyl ketone and Antimicrobial Evaluation. HJBC. 2022;50(3):263-7.

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