BE-14348 SUBSTANCES, NEW SPECIFIC ESTROGEN-RECEPTOR BINDING INHIBITORS PRODUCTION, ISOLATION, STRUCTURE DETERMINATION AND BIOLOGICAL PROPERTIES

• Published in: Journal of antibiotics Vol. 43; no. 12; pp. 1533 - 1542
• Main Authors: KONDO, HISAO, NAKAJIMA, SHIGERU, YAMAMOTO, NAOKO, OKURA, AKIRA, SATOH, FUMIO, SUDA, HIROYUKI, OKANISHI, MASANORI, TANAKA, NOBUO
• Format: Journal Article
• Language: English
• Published: Japan JAPAN ANTIBIOTICS RESEARCH ASSOCIATION 01.12.1990
• Subjects: Animals; Breast Neoplasms; Chromatography; Estrogen Antagonists - chemistry; Estrogen Antagonists - isolation & purification; Estrogen Antagonists - pharmacology; Female; Fermentation; Flavanones; Flavonoids - biosynthesis; Flavonoids - chemistry; Flavonoids - isolation & purification; Flavonoids - pharmacology; HeLa Cells; Magnetic Resonance Spectroscopy; Mass Spectrometry; Microscopy, Electron, Scanning; Molecular Conformation; Molecular Structure; Receptors, Estrogen - antagonists & inhibitors; Receptors, Estrogen - metabolism; Soil Microbiology; Solubility; Stereoisomerism; Streptomyces - classification; Streptomyces - metabolism; Streptomyces - ultrastructure; Swine; Tumor Cells, Cultured; Uterus - metabolism
• ISSN: 0021-8820; 1881-1469
• DOI: 10.7164/antibiotics.43.1533

Streptomyces graminofaciens BA14348, isolated from a soil sample, was found to produce new specific inhibitors of estrogen binding to its receptor. Five related substances, BE-14348A-E, were isolated, and their structures were determined by analyses of spectral properties. Of these substances, A was identical with the known flavanone, naringenin. On the other hand, B, C, D and E were all new compounds; the structure of B was determined to be 2(S):3(S)-3-methyl-4', 5, 7-trihydroxyflavanone, C was a racemic mixture of 2(S):3(R) and 2(R):3(S)-3-methyl-4', 5, 7-trihydroxyflavanone; D and E were 8-chloro derivatives of B and C, respectively.