Novel 24-membered macrolides, JBIR-19 and -20 isolated from Metarhizium sp. fE61.
In the course of our screening program for active compounds that induce cell morphological changes of Saccharomyces cerevisiae, the culture broth of an entomopathogenic fungus Metarhizium sp. fE61 exhibited a unique morphological phenotype. We conducted an activity-guided isolation from the fermentation broth of Metarhizium sp. fE61 to yield two new macrolide compounds named JBIR-19 (1) and -20 (2) as active substances. Their structures were determined to be 24-membered macrolide analogs containing a 2-aminoethyl phosphate ester on the basis of NMR and other spectroscopic data. Compounds 1 and 2 induced striking elongated morphology of S. cerevisiae at concentrations of 3.1 and 13 microM, but showed weak antiyeast activity at MICs of 200 and >200 microM, respectively.
Kozone
Ikuko
I
Biomedicinal Information Research Center (BIRC), Japan Biological Informatics Consortium (JBIC), Koto-ku, Tokyo, Japan.
Ueda
Jun-ya
JY
Watanabe
Machika
M
Nogami
Satoru
S
Nagai
Aya
A
Inaba
Shigeki
S
Ohya
Yoshikazu
Y
Takagi
Motoki
M
Shin-ya
Kazuo
K
D000935:Antifungal Agents / Q000096:biosynthesis* / Q000737:chemistry / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D003470:Culture Media; D005285:Fermentation; D018942:Macrolides / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D052981:Metarhizium / Q000145:classification / Q000378:metabolism*; D012441:Saccharomyces cerevisiae / Q000187:drug effects; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
D000935:Antifungal Agents; D003470:Culture Media; C544244:JBIR-19; C544243:JBIR-20; D018942:Macrolides