Botrytis allii

The biotransformation of (K)-(+)-pulegone was also studied by a Japanese group [116]. The major bioconversion metabolite of this substrate with Botrytis allii was (-)-(1 / )-8-hydroxy-4-p-menthen-3-one. The secondary major product from this biotransformation was isolated and its structure established as piperitenone [117]. It is interesting to note that the same group also investigated the bioconversion of piperitone, the dihydrogenation product of piperitenone a strain of Rhizoctonia solani was found able to hydroxylate the substrate preferentially at the 6-position [118,119]. 

Richmond (12) made similar observations with Botrytis allii. Pring (11) studied Uromyces vicia fabae infecting leaves of broad beans and Puccinia recondita infecting wheat. Results in these tests conducted in the intact host-pathogen system correlated well with the changes observed in nutrient solution. 

Richmond, D. V. (1984) Effects of Triadimefon on the Fine Structure of Germinating Conidia of Botrytis allii, Pesticide Biochemistry and Physiology 21, 74 - 83. 

P. janczewskii as an anti-fungal metabolite with a particular curling effect on the hyphae of the plant pathogen, Botrytis allii. The structure of griseofulvin... 

The development of resistance to chlorinated and nitrated benzene derivatives has been studied by several researchers (Priest and Wood, 1961 Georgopoulos and Zaracovitis, 1967). Botrytis allii strains in cultures under laboratory conditions could be resistant to tetrachloronitrobenzenes, dicloran and 2,3,5,6-tetra-chloronitroaniline (Priest and Wood, 1961). Resistance was not important under field conditions (Kuiper, 1965 Skorda, 1977). 

Miyazawa, M., H. Furuno, and H. Kameoka, 1992a. Biotransformation of thujone by plant pathogenic microorganism, Botrytis allii IFO 9430. Proceedings of the 36th TEAC, pp. 197-198. 

Miyazawa, M., H. Huruno, and H. Kameoka, 1991b. Biotransformation of (+)-pulegone to (-)-177-8-hydroxy-4- -menthen-3-one hy Botrytis allii. Chem. Express, 6 479-482. 

Botrytis allii converted (+)-pulegone (119) to (-)-(l/ )-8-hydroxy-4-p-menthen-3-one (121) and piperitenone (112) (Miyazawa et al., 1991a, 1991b). Hormonema isolate (UOFS Y-0067) quantitatively reduced (+)-pulegone (119) and (-)-menthone (149a) to (+)-neomenthol (137a) (van Dyk et al., 1998) (Figure 14.125). 

Piperitenone (112) is metabolized to 5-hydroxypiperitenone (117), 7-hydroxypiperitenone (118), and 7,8-dihydroxypiperitone (157). Isopiperitenol (110) is reduced to give isopiperitenone (111), which is further metabolized to piperitenone (112), 7-hydroxy- (113), 10-hydroxy- (115), 4-hydroxy- (114), and 5-hydroxy-isopiperitenone (116). Compounds 111 and 112 are isomerized to each other. Pulegone (119) was metabolized to 112, 8,9-dehydromenthenone (120) and 8-hydroxymenthenone (121) as shown in the biotransformation of the same substrate using Botrytis allii (Miyazawa et al., 1991b) (Figure 14.127). 

Botrytis allii Penicillium Aspergillus italicum niger Rhizopus nigricans Glomerella cingulata Cladosporium cucumerinum... 

Compound Botrytis allii Peniciiiium italicum Aspergillus niger Rhizopus nigricans... 

Kameda, K., H. Aoki, M. Namiki, and J.C. Overeem An Alternative Structure for Botrallin, A Metabolite of Botrytis allii. Tetrahedron Letters 1974, 103. 

Biol Prop. Activity as fungicide against Aspergillus niger, Botrytis allii, Penicillium niger, Rhizopus nigricans (221). 

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