Formation of Monohydroxy-n-Nonane-2-Ones from Tricaprin by Fusarium avenaceum f. sp. fabae IFO 7158

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Fusarium avenaceum f. sp. fabae IFO 7158 metabolized tricaprin with accumulation of n-nonane-2-one and three unknown minor compounds in the medium. The three compounds were identified to be 8-hydroxy-n-nonane-2-one, 7-hydroxy-n-nonane-2-one, and 6-hydroxy-n-nonane-2-one. The accumulation of the monohydroxy-n-nonane-2-ones took place with a decrease in n-nonane-2-one (C_<9 : 0>-2-one) once formed from capric acid (C_<10 : 0>. Thus, it is speculated that hydroxylations of n-nonane-2-one at ω2,ω3,and ω4 carbons gave the 8-hydroxy-, 7-hydroxy-, and 6-hydroxy-n-nonane-2-ones, repectively. Even though the microorganism could utilize well for growth all of the synthetic triglycerides, such as tricaproin, tricaprylin, tricaprin, trilaurin, trimyristin, and tripalmitin, the monohydroxy-n-alkane-2-one was formed exclusively from tricaprin. The maximal accumulation of monohydroxy-n-nonane-2-ones, a mixture of 8-hydroxy-, 7-hydroxy- and 6-hydroxy-n-nonane-2-ones in an approximate ratio of 10 : 7 : 0.5,was 139 mg from 1.0 g tricaprin. Finally, a novel metabolic pathway for the medium chain fatty acid in the fungus is discussed.
1991-03-25