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Year 2019, Volume: 6 Issue: 3, 8 - 15, 22.12.2019

Abstract

References

  • 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, A. M., & Letizia, C. S. (1992). Longifolene. Food Chem. Toxicol., 30(Suppl.), 67S-68S. doi:10.1016/0278-6915(92)90241-C
  • Heinlein, A., & Buettner, A. (2012). Monitoring of biotransformation of hop aroma compounds in an in vitro digestion model. Food Funct., 3(10), 1059-1067. doi:10.1039/c2fo30061c
  • Ishida, T. (2005). Biotransformation of terpenoids by mammals, microorganisms, and plant-cultured cells. Chem. Biodiversity, 2(5), 569-590. doi:10.1002/cbdv.200590038
  • Jennings, W., & Shibamoto, T. (1980). Qualitative Analysis of Flavor and Fragrance Volatiles by Glass Capillary Gas Chromatography: Academic Press.
  • Joglekar, S. S., Vora, M. A., Dhere, S. G., & Dhavilkar, R. S. (1968). Microbial transformations of terpenoids: citronellal, citral, eugenol, Δ3-carene, α-pinene, and longifolene. Indian Oil Soap J., 34(4), 85-88.
  • Johnston, C. (1989). The Wiley / NBS Registry of Mass Spectral Data, Volumes 1-7 (McLafferty, Fred W.; Stauffer, Douglas B.). Journal of Chemical Education, 66(10), A256. doi:10.1021/ed066pA256.3
  • Joulain, D., & Konig, W. (1998). The Atlas of Spectral Data of Sesquiterpene Hydrocarbons: E.B.-Verlag.
  • Khan, N. T., Atif, M., & Al-Aboudi, A. (2014). Microbial transformation of (-)-alloisolongifolene. Orient. J. Chem., 30(3), 941-945. doi:10.13005/ojc/300304
  • King, A. J., & Dickinson, J. R. (2003). Biotransformation of hop aroma terpenoids by ale and lager yeasts. FEMS Yeast Res., 3(1), 53-62. doi:10.1111/j.1567-1364.2003.tb00138.x
  • Koenig, W. A., & D. Hochmuth, J. D. H. (2004). Terpenoids and Related Constituents of Essential Oils. MassFinder 3, Hamburg, Germany.
  • Kondjoyan, N., & Berdagué, J.-L. (1996). A compilation of relative retention indices for the analysis of aromatic compounds. INRA de Theix, France: Laboratoire Flaveur.
  • Noma, Y., Hashimoto, T., Uehara, S., & Asakawa, Y. (2010). Microbial transformation of isopinocampheol and caryophyllene oxide. Flavour Fragrance J., 25(3), 161-170. doi:10.1002/ffj.1988
  • Oda, S., Fujinuma, K., Inoue, A., & Ohashi, S. (2011). Synthesis of (-)-β-caryophyllene oxide via regio- and stereoselective endocyclic epoxidation of β-caryophyllene with Nemania aenea SF 10099-1 in a liquid-liquid interface bioreactor (L-L IBR). J. Biosci. Bioeng., 112(6), 561-565. doi:10.1016/j.jbiosc.2011.07.024
  • Rychlik, M., Schieberle, P., Grosch, W., Deutsche Forschungsanstalt für, L., Universität, M., & Institut für Lebensmittelchemie der, T. (1998). Compilation of odor thresholds, odor qualities and retention indices of key food odorants. Garching: Deutsche Forschungsanstat für Lebensmittelchemie and Instit für Lebensmittelchemie der Technischen Universität München.
  • Schmitt, D., Levy, R., & Carroll, B. (2016). Toxicological evaluation of β-caryophyllene oil: subchronic toxicity in rats. Int. J. Toxicol., 35(5), 558-567. doi:10.1177/1091581816655303
  • Sharma, C., Al Kaabi, J. M., Nurulain, S. M., Goyal, S. N., Kamal, M. A., & Ojha, S. (2016). Polypharmacological Properties and Therapeutic Potential of β-Caryophyllene: A Dietary Phytocannabinoid of Pharmaceutical Promise. Curr. Pharm. Des., 22(21), 3237-3264. doi:10.2174/1381612822666160311115226
  • Wright, J. (2010). Creating and formulating flavours. In: Food Flavour Technology, Second Edition, Taylor A.J. and Linforth R.S.T., 1-23. doi:10.1002/9781444317770.ch1
  • Younis, N. S., & Mohamed, M. E. (2019). β-caryophyllene as a potential protective agent against myocardial injury: the role of toll-like receptors. Molecules, 24(10), 1929. doi:10.3390/molecules24101929

Microbial transformation of β-Caryophyllene and Longifolene by Wolfiporia extensa

Year 2019, Volume: 6 Issue: 3, 8 - 15, 22.12.2019

Abstract

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.

References

  • 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, A. M., & Letizia, C. S. (1992). Longifolene. Food Chem. Toxicol., 30(Suppl.), 67S-68S. doi:10.1016/0278-6915(92)90241-C
  • Heinlein, A., & Buettner, A. (2012). Monitoring of biotransformation of hop aroma compounds in an in vitro digestion model. Food Funct., 3(10), 1059-1067. doi:10.1039/c2fo30061c
  • Ishida, T. (2005). Biotransformation of terpenoids by mammals, microorganisms, and plant-cultured cells. Chem. Biodiversity, 2(5), 569-590. doi:10.1002/cbdv.200590038
  • Jennings, W., & Shibamoto, T. (1980). Qualitative Analysis of Flavor and Fragrance Volatiles by Glass Capillary Gas Chromatography: Academic Press.
  • Joglekar, S. S., Vora, M. A., Dhere, S. G., & Dhavilkar, R. S. (1968). Microbial transformations of terpenoids: citronellal, citral, eugenol, Δ3-carene, α-pinene, and longifolene. Indian Oil Soap J., 34(4), 85-88.
  • Johnston, C. (1989). The Wiley / NBS Registry of Mass Spectral Data, Volumes 1-7 (McLafferty, Fred W.; Stauffer, Douglas B.). Journal of Chemical Education, 66(10), A256. doi:10.1021/ed066pA256.3
  • Joulain, D., & Konig, W. (1998). The Atlas of Spectral Data of Sesquiterpene Hydrocarbons: E.B.-Verlag.
  • Khan, N. T., Atif, M., & Al-Aboudi, A. (2014). Microbial transformation of (-)-alloisolongifolene. Orient. J. Chem., 30(3), 941-945. doi:10.13005/ojc/300304
  • King, A. J., & Dickinson, J. R. (2003). Biotransformation of hop aroma terpenoids by ale and lager yeasts. FEMS Yeast Res., 3(1), 53-62. doi:10.1111/j.1567-1364.2003.tb00138.x
  • Koenig, W. A., & D. Hochmuth, J. D. H. (2004). Terpenoids and Related Constituents of Essential Oils. MassFinder 3, Hamburg, Germany.
  • Kondjoyan, N., & Berdagué, J.-L. (1996). A compilation of relative retention indices for the analysis of aromatic compounds. INRA de Theix, France: Laboratoire Flaveur.
  • Noma, Y., Hashimoto, T., Uehara, S., & Asakawa, Y. (2010). Microbial transformation of isopinocampheol and caryophyllene oxide. Flavour Fragrance J., 25(3), 161-170. doi:10.1002/ffj.1988
  • Oda, S., Fujinuma, K., Inoue, A., & Ohashi, S. (2011). Synthesis of (-)-β-caryophyllene oxide via regio- and stereoselective endocyclic epoxidation of β-caryophyllene with Nemania aenea SF 10099-1 in a liquid-liquid interface bioreactor (L-L IBR). J. Biosci. Bioeng., 112(6), 561-565. doi:10.1016/j.jbiosc.2011.07.024
  • Rychlik, M., Schieberle, P., Grosch, W., Deutsche Forschungsanstalt für, L., Universität, M., & Institut für Lebensmittelchemie der, T. (1998). Compilation of odor thresholds, odor qualities and retention indices of key food odorants. Garching: Deutsche Forschungsanstat für Lebensmittelchemie and Instit für Lebensmittelchemie der Technischen Universität München.
  • Schmitt, D., Levy, R., & Carroll, B. (2016). Toxicological evaluation of β-caryophyllene oil: subchronic toxicity in rats. Int. J. Toxicol., 35(5), 558-567. doi:10.1177/1091581816655303
  • Sharma, C., Al Kaabi, J. M., Nurulain, S. M., Goyal, S. N., Kamal, M. A., & Ojha, S. (2016). Polypharmacological Properties and Therapeutic Potential of β-Caryophyllene: A Dietary Phytocannabinoid of Pharmaceutical Promise. Curr. Pharm. Des., 22(21), 3237-3264. doi:10.2174/1381612822666160311115226
  • Wright, J. (2010). Creating and formulating flavours. In: Food Flavour Technology, Second Edition, Taylor A.J. and Linforth R.S.T., 1-23. doi:10.1002/9781444317770.ch1
  • Younis, N. S., & Mohamed, M. E. (2019). β-caryophyllene as a potential protective agent against myocardial injury: the role of toll-like receptors. Molecules, 24(10), 1929. doi:10.3390/molecules24101929
There are 29 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Özge Özşen Batur

İsmail Kıran This is me

Ralf G. Berger This is me

Betül Demirci

Publication Date December 22, 2019
Published in Issue Year 2019 Volume: 6 Issue: 3

Cite

APA Özşen Batur, Ö., Kıran, İ., Berger, R. G., Demirci, B. (2019). Microbial transformation of β-Caryophyllene and Longifolene by Wolfiporia extensa. Natural Volatiles and Essential Oils, 6(3), 8-15.