Limonene litura

Both the (+)- and (-)- enantiomers of limonene were transformed by larvae of the cutworm Spodop-tera litura (Miyazawa et al. 1998). For both of them the reactions involved are (a) dihydroxylation between C-8 and C-9 and (b) oxidation of the C-1 methyl group to carboxyl. These transformations were not dependent on the intestinal microflora in contrast to the transformation of a-terpinene to p-mentha-l,3-dien-7-ol and p-cymene whose formation could be attributed to the intestinal flora. 

Miyazawa, M., T. Wada, and H. Kameoka. 1998. Biotransformation of (+) and (-) limonene by the larvae of common cutworm (Spodoptera litura).. Agric. Food Chem. 46 300-303. 

FIGURE 19.39 Biotransformation of (+) limonene (68) and (-)-limonene (68 ) by Spodoptera litura. (Modi ed from Miyazawa, M. et al., Biotransformation of terpinene, limonene and a-phellandrene in common cutworm larvae, Spodoptera litura Fabricius, Proceedings of 39th TEAC, 1995a. pp. 362-363.)... 

As shown in Figure 19.49, S. litura converted (4/ )-p-menth-l-ene (62) at C-7 position to (47 )-phellandric acid (65) (Miyazawa et al, 1996b). On the other hand, when Cladosporium sp. Ti was cultivated with (+)-limonene (68) as the sole carbon source, it converted 62 to trans-p-menthane-l,2-diol (54) (Mukherjee et al, 1973). 

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