Botryosphaeria dothidea

Stereoselectivity in the Biotransformation of 1,8-Cineole (122) by Aspergillus niger, Botryosphaeria dothidea, and Pseudomonas dava ... 

Biotransformation of Nootkatone (2) by Fusarium culmorum AND Botryosphaeria dothidea... 

FIGURE 20.59 Biotransformation of y-cyclocostunolide (171) by Aspergillus niger, Aspergillus cellulosae, and Botryosphaeria dothidea. 

FIGURE 20.79 Biotransformation of (-)-dehydrocostuslactone (249) hy Aspergillus species and Botryosphaeria dothidea. 

The expensive grapefruit aromatic, nootkatone (2) used by cosmetic and fiber manufacturers was obtained in high yield by biotransformation of (+)-valencene (1), which can be cheaply obtained from Valencia orange, by Chlorella species, fungi such as Mucor species, Botryosphaeria dothidea, and Botryodiplodia theobromae. This is a very inexpensive and clean oxidation reaction, which does not use any heavy metals, and thus this method is expected to find applications in the industrial production of nootkatone. 

The biotransformation of 2 by Aspergillus niger and Botryosphaeria dothidea resembled to that of the oral administration to rabbit since the ratio of the major metabolites 115- (6) and 1 l/ -nootkatone-11,12-diol (7) was similar. It is noteworthy that the biotransformation of 2 by Fusarium culmorum affords stereospecifically nootkatone-11/ , 12-diol (7) (Noma et al., 2001a) (Figure 15.10). 

Botryosphaeria dothidea has no stereoselectivity to rednce C11-C13 double bond of p-cyclocos-tnnolide (170) since this organism gave two dihydro derivatives 182 (16.7%) and 183 (37.8%), respectively, as shown in Figure 15.57. 

FIGURE 15.57 Biotransformation of P-cyclocostunolide (170) hy Aspergillus cellulosae tind Botryosphaeria dothidea. 

Ma, Z., Morgan, D.P., Felts, D. and Michailides, T.J. (2002) Sensitivity of Botryosphaeria dothidea from California pistachio to tebuconazole. Crop Protection 21 (9) 829-835. 

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