New milbemycins from Streptomyces hygroscopicus subsp. aureolacrimosus: fermantation, isolation and strucutre elucidation.
Twelve new milbemycins have been isolated and characterized from some strains derived from Streptomyces hygroscopicus subsp. aureolacrimosus SANK 60286 and SANK 60526. The metabolites 1 approximately 4 and 9 approximately 11 were produced by strain RM28D-688 SANK 60797 as minor products. The metabolites 5 approximaetly 8 were obtained from a broth of strain 57-338 SANK 61796. Strain MK-1391 SANK 62896 was used for the production of metabolite 12. The new metabolites, eight alpha-class and four beta-class compounds, have new structural features. For example, milbemycins alpha26 and alpha27, have the 26-hydroxy moiety, and other derivatives (milbemycins alpha20 approximately 23) have different side chains at the C-26 position from those of milbemycins alpha11 and alpha14. In addition, 5-hydroxylmilbemycin beta7 (beta12), involved in the major biosynthetic pathway of 25-methyl and 25-ethyl milbemycins, was discovered.
Nonaka
K
K
Lead Discovery Research Laboratories, Sankyo Co., Ltd., Iwaki-shi, Fukushima, Japan.
Tsukiyama
T
T
Okamoto
Y
Y
Sato
K
K
Kumasaka
C
C
Yammoto
T
T
Maruyama
F
F
Yoshikawa
H
H
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism; D005285:Fermentation; D018942:Macrolides; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D013302:Streptomyces / Q000378:metabolism*
D000900:Anti-Bacterial Agents; D018942:Macrolides; C027837:moxidectin