Corynespora cassiicola

Stereospecific Biotransformation of (/ )-Linaiooi by Corynespora cassiicola DSM 62475 into Linalool Oxides... 

The biotransformation of (/f,5)-Iinalool by fungi is a useful method for the preparation of natural linalool oxides. The stereospecific conversion of (J ,5)-linalool by Corynespora cassiicola DSM 62475 led to 5/f-configured furanoid linalool oxides and 55-configured pyranoid linalool oxides, both via bS -configured epoxylinalool as postulated intermediate (Figure 12.6). The biotransformation protocol affords an almost total conversion of the substrate with high enantioselectivities and a molar conversion yield close to 100% (Table 12.4). Pure linalool oxides are of interest for lavender notes in perfumery. ... 

The same group also studied the bioconversion of Z- and -nerolidol with three more fungal species Diplodia gossypina, Corynespora cassiicola and Gibberella cyanea [112]. It was found that all strains hydroxylated the substrates to their respective vicinal diols (glycols). The highest yield was obtained with the strain G. cyanea (79.5%) and the substrate -nerolidol. Also hydroxyketones were found in lower yields (0.5-5%) and in some cases traces of epoxides were produced. 

Staphylococcus aureus Lactobacillus plantarum Pseudopleuronectes americanus Corynespora cassiicola Ecballium elaterium Staphylococcus epidermidis Helianthus annuus... 

Isp-Hydroxylation 1ip,21-Dihydroxy- pregn-4-ene-3,20- dione lip, 18,21-Trihydroxy- pr n-4-ene-3,20- dione Corynespora cassiicola... 

Kondo, Mitsugi, and Tori (Ap-38) extended this finding to develop a synthesis of aldosterone, using Corynespora cassiicola. 

Hydroxylation of corticosterone by Corynespora cassiicola and Corynespora melonis. Microbial synthesis of aldosterone. 

The production of glycols from limonene (68) and other terpenes with a 1-menthene skeleton was reported by Corynespora cassiicola DSM 62475 and D. gossypina ATCC 10936 (Abraham et al., 1984). Accumulation of glycols during fermentation was observed. An extensive overview on the microbial transformations of terpenoids with a 1-p-menthene skeleton was published by Abraham et al. (1986). 

FIGURE 19.53 Biotransformation of terpinolene (346) by Aspergillus niger (Asakawa et al., 1991), Corynespora cassiicola (Abraham et al., 1985), rabbit (Asakawa et al., 1983), and 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.)... 

C. aphidicola bioconverted cedrol (414) into 417 (Hanson and Nasir, 1993). On the other hand, Corynespora cassiicola produced 419 in addition to 417 (Abraham et ah, 1987). It is noteworthy that B. cinerea that damages many owers, fruits, and vegetables biotransformed cedrol into different metabolites (420-422) from those mentioned earlier (Aleu et ah, 1999a). 

Terpinolene (346) was converted by Aspergillus niger to give (l/ )-8-hydroxy-3-p-menthen-2-one (347), (l/ )-l,8-dihydroxy-3-p-menthen-2-one (348), and 5P-hydroxyfenchol (350b ). In case of Corynespora cassiicola it was converted to terpinolene-l,2-tra 5 -diol (351) and terpinolene-4,8-diol (352). Furthermore, in case of rabbit terpinolene-9-ol (353) and terpinolene-lO-ol (354) were formed from 346 (Asakawa et al., 1983). Spodoptera litura also converted 346 to give l-p-menthene, 8-diol (352), cuminic acid (194, 29% main product), and terpinolene-7-oic acid (357) (Figure 14.53). 

While i -(+)-limonene (134), for example, was completely and specifically converted by PenicilUum digitatum DSM 6284 to the corresponding a-terpineol enantiomer 135 [159,160], both limonene enantiomers were oxidized by Corynespora cassiicola DSM... 

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