Diplodia gossypina

Recently, a patent described the use of Diplodia gossypina ATCC 10936 for the production of natural jasmonic acid [47]. With submerged cultures, up to 1.5 g L" jasmonic acid was obtained after 11 days of incubation the addition of 10-oxo-8-fra s-decenoic acid, a hormone stimulating mycelial growth, proved to be advantageous methyl jasmonate was obtained by autoclaving the... 

Fig. (3). Hydroxylation of myrcene by Diplodia gossypina (after[24]> and by Ganoderma applanatum and Pleurotus sp. (after [25])...

Another example of fungal bioconversion of linalool was described in literature the biotransformation by Diplodia gossypina ATCC 10936 [61]. A conversion scheme for the bioconversion of both (/ )-(-)- and (S)-(+)-linalool was proposed. 

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. 

Abraham et al. [144-146] studied the biotransformation of caryophyllene (190) and humulene (196) by Diplodia gossypina (ATCC 10936) and two strains of Chaetomium cochliodes (DSM 63353 and ATCC 10195), Fig. (38) and Fig. (39). Sixty three products, including 49 that had never been described previously, were obtained and tested for their biological activity [147]. More recently, the bioconversion of (-)-caryophyllene by Chaetomium cochliodes IFO 30576 was also studied by another group [148]. The substrate was first epoxidized at the C-C double bond, producing (-)-caryophyllene-4,5-oxide (191), which was then hydroxylated at the ge/n-dimethyl group and C-7 position giving 193. 

Fig. (38). Main biotransformation products of caryophyllene by Diplodia gossypina and Chaetomium cochliodes (after [144,145])...

The microbial transformation of humulene, a substrate showing a structure similar to that of germacrone, was studied by Abraham and Stumpf using a screen of about 300 strains1175 . This led the authors to select the fungi Diplodia gossypina and Chaetonium cochlioides for preparative scale experiments. It was thus observed that the main reaction path starts with the epoxidation of the 1,2-double bond, as shown by direct biotransformation of this monoepoxide obtained by chemical synthesis. This is then further oxidized to yield a multitude of products including diepoxides and hydroxy-epoxides (Fig. 16.1-28). 

The microbial biotransformation of myrcene (302) was described with Diplodia gossypina ATCC 10936 (Abraham et al., 1985). The main reactions were hydroxylation, as shown in Figure 19.1. On oxidation, myrcene (302) gave the diol (303) (yield up to 60%) and also a side product (304) that possesses one carbon atom less than the parent compound, in yields of l%-2%. 

FIGURE 20.23 Biotransformation of l(10)-aristolene (36) by Diplodia gossypina and Bacillus megaterium. 

FIGURE 20.131 Biotransformation of (-)-P-caryophyllene (451) by Pseudomonas cruciviae, Diplodia gossypina, and Chaetomium cochliodes. 

Abraham, W.R., L. Ernst, and B. Stumpf, 1990. Biotransformation of caryophyllene by Diplodia gossypina. 

The production of glycols from limonene (68) and other terpenes with a 1-menthene skeleton was reported by Corynespora cassiicola DSM 62475 and Diplodia gossypina ATCC 10936 (Abraham et ah, 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 etal. (1986). 

Metabolic pathways of myrcene (302) and citronellene (309) by microorganisms and insects are summarized in Figure 14.205. i-Myrcene (302) was metabolized with Diplodia gossypina ATCC 10936 (Abragam et al., 1985) to the diol (303) and a side-product (304). P-Myrcene (302) was metabolized with Ganoderma applanatum, Pleurotus flabellatus, and Pleurotus sajor-caju to myrcenol (305) (2-methyl-6-methylene-7-octen-2-ol) and 306 (Busmann and Berger, 1994). 

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 gossypina. In 3rd European Congr. on Biotechnology, Vol. 1, pp. 245-248. Verlag Chemie, Weinheim. 

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