As a result, microbial transformation reactions produced various volatile compounds mainly consisting of ketones, aldehydes and alcohol-bearing derivatives of β-caryophyllene and longifolene.
📌 3 Key Takeaways
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Objective & Hypothesis:β-Caryophyllene and longifolene are sesquiterpenes with characteristic aroma properties, which are primary constituents of essential oils and important ingredients commonly used in food, perfumery, cosmetics, detergents and pharmaceuticals, which create a worldwide market. β-Caryophyllene and longifolene were converted through microbial biotransformation by using Wolfiporia extensa to a mixture of products over seven days at 25 oC to be evaluated as potential aroma and antimicrobial agents.
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Key Findings & Data:The characterization of transformation products was carried out by comparison of their GC-MS spectra and retention indices with that of published data (Wiley, NIST and ADAMS databases).
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Conclusion & Impact:As a result, microbial transformation reactions produced various volatile compounds mainly consisting of ketones, aldehydes and alcohol-bearing derivatives of β-caryophyllene and longifolene.
β-Caryophyllene and longifolene are sesquiterpenes with characteristic aroma properties, which are primary constituents of essential oils and important ingredients commonly used in food, perfumery, cosmetics, detergents and pharmaceuticals, which create a worldwide market. β-Caryophyllene and longifolene were converted through microbial biotransformation by using Wolfiporia extensa to a mixture of products over seven days at 25 oC to be evaluated as potential aroma and antimicrobial agents. The characterization of transformation products was carried out by comparison of their GC-MS spectra and retention indices with that of published data (Wiley, NIST and ADAMS databases). As a result, microbial transformation reactions produced various volatile compounds mainly consisting of ketones, aldehydes and alcohol-bearing derivatives of β-caryophyllene and longifolene.
BATUR, Ö. Ö., KIRAN, İ., BERGER, R. G., DEMİRCİ, B. (2019). Microbial transformation of β-Caryophyllene and Longifolene by Wolfiporia extensa. Natural Volatiles and Essential Oils, Cilt: 6 Sayı: 3, 8–15. https://ajindex.com/articles/1003504
Abraham, W. R., Hoffmann, H. M., Kieslich, K., Reng, G., & Stumpf, B. (1985). Microbial transformations of some monoterpenoids and sesquiterpenoids. Ciba Found Symp, 111, 146-160.
Adams, R. P. (1995). Identification of Essential Oil Components by Gas Chromatography/mass Spectrometry. Carol Stream: Allured Publishing Corporation. Andersen, F. A., Bergfeld, W. F., Belsito, D. V., Hill, R. A., Klaassen, C. D., Liebler, D. C.,. Snyder, P. W. (2010). Final report of the cosmetic ingredient review expert panel amended safety assessment of Calendula officinalis-derived cosmetic ingredients. Int. J. Toxicol., 29(Suppl. 4), 221S-243S. doi:10.1177/1091581810384883 Asakawa, Y., Ishida, T., Toyota, M., & Takemoto, T. (1986). Terpenoid biotransformation in mammals. IV Biotransformation of (+)-longifolene, (-)-caryophyllene, (-)-caryophyllene oxide, (-)-cyclocolorenone, (+)-nootkatone, (-)-elemol, (-)-abietic acid and (+)-dehydroabietic acid in rabbits. Xenobiotica, 16(8), 753-767. doi:10.3109/00498258609043566 Berger, R. G., & Editor. (2007). Flavours and Fragrances: Chemistry, Bioprocessing and Sustainability: Springer GmbH. Bhattacharyya, P. K., Prema, B. R., Dhavalikar, R. S., & Ramchandran, B. V. (1963). Microbiological transformations of terpenes. IV. Structure of an anhydride obtained after fermentation of some terpenoid hydrocarbons by Aspergillus niger. Indian J. Chem., 1, 171-176.
Cao, Y., Zhang, R., Liu, W., Zhao, G., Niu, W., Guo, J.,. Liu, H. (2019). Manipulation of the precursor supply for high-level production of longifolene by metabolically engineered Escherichia coli. Sci. Rep., 9(1), 1-10. doi:10.1038/s41598-018-36495-w Choudhary, M. I., Siddiqui, Z. A., Nawaz, S. A., & Atta ur, R. (2006). Microbial Transformation and Butyrylcholinesterase Inhibitory Activity of (-)-Caryophyllene Oxide and Its Derivatives. J. Nat. Prod., 69(10), 1429-1434. doi:10.1021/np0680174 Dev, S. (1981). Aspects of longifolene chemistry. An example of another facet of natural products chemistry. Acc. Chem. Res., 14(3), 82-88. doi:10.1021/ar00063a004 Devi, J. R. (1979). Microbiological transformations of terpenes. Part XXVI. Microbiological transformation of caryophyllene. Indian J. Biochem. Biophys., 16(2), 76-79.
Fitjer, L., Malich, A., Paschke, C., Kluge, S., Gerke, R., Rissom, B.,. Noltemeyer, M. (1995). Rearrangement of (-)-β-Caryophyllene. A Product Analysis and Force Field Study. J. Am. Chem. Soc., 117(36), 9180-9189. doi:10.1021/ja00141a009 Ford, R. A., Api,