Microbial conversion of milbemycins: 30-oxidation of milbemycin A4 and related compounds by Amycolata autotrophica and Amycolatopsis mediterranei.
Microorganisms were screened for their ability to modify milbemycin A4 (1a). Many strains, mostly actinomycetes and zygomycetes, were found to convert milbemycin A4 (1a) to one or more new products. Among these products, M-1, M-2, and M-3 were obtained using Amycolata autotrophica subsp. amethystina ATCC 35204, and were identified as 30-hydroxymilbemycin A4 (1b), 26,30-dihydroxymilbemycin A4 (1c), and milbemycin A4 30-oic acid (1d), respectively. Other milbemycins and LL-F28249 alpha (7a) also underwent 30-hydroxylation by the microorganism. 22,23-Dihydroavermectin B1a (8a) was not hydroxylated at any position by A. autotrophica subsp. amethystina ATCC 35204, but a corresponding hydroxyl product at the C-30 position was obtained using Amycolatopsis mediterranei IFO 13415.
Nakagawa
K
K
Fermentation Research Laboratories, Sankyo Co., Ltd., Tokyo, Japan.
Torikata
A
A
Sato
K
K
Tsukamoto
Y
Y
D000192:Actinomycetales / Q000378:metabolism*; D000871:Anthelmintics / Q000737:chemistry / Q000378:metabolism*; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D007306:Insecticides / Q000737:chemistry / Q000378:metabolism*; D018942:Macrolides; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction
D000871:Anthelmintics; D000900:Anti-Bacterial Agents; D007306:Insecticides; D018942:Macrolides; C027837:moxidectin