PF1163A and B are a pair of antifungal agents isolated from a fermentation broth of Penicillium sp. PF1163A inhibited ergosterol synthesis in Saccharomyces cerevisiae, resulting in an accumulation of 4,4-dimethylzymosterol and a decrease of ergosterol. The ERG25 strain overexpressing the ERG25 gene was resistant to PF1163A. ERG25p is a C-4 sterol methyl oxidase known to be essential for the viability of yeast and fungi because of the known role of ERG25 gene disruption in S. cerevisiae-led lethality. ERG25p is the enzyme responsible for the first step in the removal of the two methyl groups at the C-4 position of sterol. From the results obtained here, we conclude that PF1163A is a novel natural antifungal that inhibits C-4 sterol methyl oxidase.

01 Jan 2000·The Journal of AntibioticsQ4 · MEDICINE

PF1163A and B, New Antifungal Antibiotics Produced by Penicilium sp. II. Physico-chemical Properties and Structure Elucidation.

Q4 · MEDICINE

Article

Author: Satoko Takano ; Yasuo Ohtsuka ; Kuniaki Tatsuta ; Takashi Watanabe ; Takashi Shomura ; Toru Sasaki ; Hiroshi Nose ; Shigemi Yoshida ; Takayuki Usui ; Ayako Hosoya ; Mami Kawaguchi

The structures of new antifungal antibiotics, PF1163A and B, were elucidated by spectroscopic analyses of the degradation products and by X-ray crystallography of the de-2-hydroxyethyl derivative of PF1163B. Both antibiotics consist of a 13-membered macrocyclic structure containing a derivative of N-methyl tyrosine and a hydroxy fatty acid. PF1163A differs from PF 1163B by having an additional hydroxyl group on the side chain.

01 Jan 1999·The Journal of AntibioticsQ4 · MEDICINE

The Total Synthesis and Absolute Structure of Antifungal Antibiotics (-)-PF 1163A and B.

Q4 · MEDICINE

Letter

Author: Satoko Takano ; Kuniaki Tatsuta ; Shojiro Miyazaki ; Yuichi Ikeda ; Satoshi Nakano

The total synthesis of (-)-PF1163A and B (I, R = β-OH, H) from Boc-L-tyrosine and (R)-citronellol was accomplished and their absolute configurations determinedConversion of the protected intermediate from Boc-L-tyrosine with β-naphthoyl chloride to the mixed anhydride followed by reaction of II gave III which after removal of all protecting groups yielded an amino acid which was cyclized by Bop-Cl to give 62% of (-)-PF1163B.(-)-PF1163A was prepared via similar strategy and both were identical to the natural antibiotics in all respects.

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Indication	Highest Phase	Country/Location	Organization	Date
Mycoses	Discovery	JP	Meiji Seika Pharma Co., Ltd.	-

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