PF1092A, B and C, New Nonsteroidal Progesterone Receptor Ligands Produced by Penicillium oblatum II. Physico-chemical Properties and Structure Elucidation

• Published in: Journal of antibiotics Vol. 50; no. 4; pp. 309 - 313
• Main Authors: TABATA, YUJI, HATSU, MASAHIRO, KURATA, YASUSHI, MIYAJIMA, KAORI, TANI, MASATO, SASAKI, TORU, KODAMA, YOSHIO, TSURUOKA, TAKASHI, OMOTO, SHOJI
• Format: Journal Article
• Language: English
• Published: Tokyo JAPAN ANTIBIOTICS RESEARCH ASSOCIATION 01.04.1997; Japan Antibiotics Research Association
• Subjects: Antibiotics (antibacterial agents, antifungal agents); Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents; Applied microbiology; Biological and medical sciences; Fundamental and applied biological sciences. Psychology; Furans - chemistry; Furans - pharmacology; Microbiology; Molecular Structure; Naphthols - chemistry; Naphthols - pharmacology; Sesquiterpenes - chemistry; Ligand; Lactone; Acetate; Fungi; Antibiotic; Sesquiterpenes; Acetylation; Fungi Imperfecti; Progesterone; Non steroid compound; Physicochemical properties; Thallophyta; Structural analysis; Hormonal receptor
• ISSN: 0021-8820; 1881-1469
• DOI: 10.7164/antibiotics.50.309

The structures of PF1092A (1), B (2) and C (3), new nonsteroidal progesterone receptor ligands produced by Penicillium oblatum, were elucidated by spectroscopic analyses. These compounds possess an eremophilane-type sesquiterpene carbon skeleton and differ only in that 1 and 2 are different monoacetates of 3. The absolute configurations of 1-3 were determined by single crystal X-ray diffraction analysis of the 4-bromobenzoyl ester of PF1092A and by measuring the optical rotations of the acetylation products of these compounds.