Monoterpenes, microbial transformation

Tissue Cultures, Microbial Transformations.—Little success has rewarded the search for cell cultures that effectively biosynthesize monoterpenes de novo. The most impressive studies utilize cultures from a variety of Mentha spp. yields of oil were some 60 % (w/v) of those in the parent plants, but the monoterpene products were generally more oxidized (i.e. ketones extra C=C bonds predominated). In vitro, oxidation at C-3 of the menthane skeleton was also restricted, apparently owing to an inhibition of the enzymic reduction of the 4(8) double bond in the intermediates formed.925 926 Colchicine stimulated synthesis of essential oil by Mentha cultures.927 Iridoid glucosides have been produced by cultured cells of Gardenia spp.673 Menthone was biotransformed to neomenthol by Mentha suspension cultures,928 and Nicotiana lines oxidized linalool and its derivatives at C-10 to aldehydes and alcohols,929 and also foreign substrates such as a-terpineol (at C-6 and C-7) and /raw.s-/ -menthan-9-en-l-ol (at C-4 and C-10).930... 

Microbial Transformation of Monoterpenes Flavor and Biological Activity... 

FIGURE 19.80 Biotransformation of carvacrol (191) and carvacrol methyl ether (191-Me) by rats. (Modi ed from Ausgulen, L.T. et al., Pharmacol. Toxicol., 61, 98, 1987) and microorganisms (Modi ed from Demirci. R, Microbial transformation of bioactive monoterpenes. Ph.D. thesis, Anadolu University. Eskisehir, Turkey, 2000, pp. 1-137.)... 

Abraham, W.-R., H.M.R. Hoffmann, K. Kieslich, G. Reng, and B. Stumpf, 1985. Microbial transformation of some monoterpenes and sesquiterpenoids. In Enzymes in Organic Synthesis, R. Porter and S. Clark, ed., Ciba Foundation Symposium 111, pp. 146-160. London, U.K. Pitman Press. 

Abraham, W.-R., K. Kieslich, H. Reng, and B. Stumpf, 1984. Formation and production of 1,2-trans-glycols from various monoterpenes with 1-menthene skeleton by microbial transformations with Diplodia gos-sypina. In Third European Congress on Biotechnology, Vol. 1, pp. 245-248. VerlagChemie, Weinheim, Germany. 

Demirci, F., 2000. Microbial transformation of bioactive monoterpenes. PhD thesis, pp. 1-137. Anadolu University, Fskisehir, Turkey. 

Madyastha, K.M. 1984. Microbial transformations of acyclic monoterpenes. Proc. Indian Acad. Sci. (Chem. Sci.), 93 677-686. 

Nishimura, H., S. Hiramoto, J. Mizutani, Y. Noma, A. Furusaki, and T. Matsumoto, 1983b. Structure and biological activity of bottrospicatol, a novel monoterpene produced by microbial transformation of -) -cis-carveol. 47 2697 2699. 

Nishimura, H. and Y. Noma, 1996. Microbial transformation of monoterpenes Flavor and biological activity. In Biotechnoloev for Improved Foods and Flavors. G.R. Takeoka, R. Teranishi, P.J. Williams, and A. Kobayashi, A., eds., ACS Symposium Series 637, pp. 173-187. Washington, DC American Chemical Society. 

Trudgill PW (1994) Microbial metabolism and transformation of selected monoterpenes. In Biochemistry of Microbial Degradation (Ed C Ratledge), pp. 33-61. Kluwer Academic Publishers, Dordrecht, The Netherlands. 

Scheme 23.9 Some microbial monoterpene transformations leading to interesting flavour molecules...

Rama Devi, J. and P.K. Bhattacharyya. 1978. Molecular rearrangements in the microbiological transformations of terpenes and the chemical logic of microbial processes. J. Indian Chem. Soc., 55 1131-1137. Rapp, A. and H. Mandery, 1988. In uence of Botrytis cinerea on the monoterpene fraction wine aroma. In Bioflavour 87. Analysis—Biochemistry—Biotechnology, P. Schreier. ed.. pp. 445-452. Berlin, Germany Walter de Gruyter and Co. 

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