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In previous papers, we reported that milbemycins were converted into 30-hydroxy, 13/Miydroxy, and 13/?,29-dihydroxy derivatives by using Amycolata autotrophica subsp. amethystina ATCC 35204, Cunninghamella echinulata ATCC9244, and Streptomyces cavourensis SANK67386, respectively.4~6) As part of our continuing screening effort for microbial conversion of milbemycins, we observed that Syncephalastrum racemosum and Syncephalastrum nigricans had conversion abilities to milbemycin A4 (la). The present paper describes the isolation and identification of converted products of milbemycin A4 (la), A3 (2a), D (3a) and 5-ketomilbemycin A4 5-oxime (4a) by S. racemosum (Fig. 1). Milbemycins conversion were followed by TLC (Merck Art. No. 5715: EtOAc) and HPLC (column: Waters, Nova pak C18 8mmx10cm; solvent: system 1, acetonitrile-water (75 :25), with a flow rate of 1.5 ml/minute; system 2, acetonitrile -water (55 : 45), with a flow rate of 1.0ml/minute; detector: UV 243 nm). S. racemosum SANK42672 was cultured in five 500-ml Erlenmeyer flasks containing 100ml MY medium composed of glucose 1.0%, Polypepton (Daigo Nutritive Chemicals) 0.5%, yeast extract (Difco) 0.3%, and malt extract (Difco) 0.3% (pH 6.3 ~6.5) at 26°C on a rotary shaker (200~220 rpm).

Microbial conversion of milbemycins: 29-Hydroxylation of milbemycins by genus Syncephalastrum.