BE-14348 substances, new specific estrogen-receptor binding inhibitors. Production, isolation, structure determination and biological properties.

Abstract

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(7?) : 3(S)-3-methyl-4',5,7-trihydroxyrlavanone; D and E were 8-chloro derivatives of B and C, respectively.

Identification and characterization of a novel estrogenic ligand actinopolymorphol A

“…Beyond the molecular diversity presented by natural product extracts, a strong motivator for interest in the screening of natural product extracts is their ready availability via scaled up fermentation of the producing organism and our ability to produce analogs via the application of combinatorial biosynthesis methods. Finally, it is well established that terrestrial microbes are a rich source for xenoestrogens [21, 22, 30-33]. This realization supported our hypothesis that crude extracts from the WDL might be an excellent source of ER modulators.…”

“…Metabolites of xenoestrogenic and phytoestrogenic compounds have been demonstrated to be produced by several bacterial strains including those present in the intestinal flora [15-20] and soil bacteria [21, 22]. For example, bisphenol A (BPA) can be metabolized by many organisms ranging from microorganisms to animals, and these transformations represent an important pathway for its detoxification [23].…”

Efeitos dos Fitoestrogênios sobre Alguns Parâmetros Clínicos e Laboratoriais no Climatério

“…O poder estrogênico destas substâncias é variável. O grupo de isoflavona (malonilgenistina, malonildaidzina, genistina, daidzina, genisteína, daidzeína, acetildaidzina, gliciteína, acetilgenistina e equol) tem maior atividade estrogênica e maior afinidade pelos receptores [4][5][6][7][8][9] . Um dos metoxi-derivados da isoflavona, chamado de biochanin A, não se liga aos receptores de estrogênios mas tem efeito estrogênico in vivo.…”

Synthesis and Transformation of Halochromones

“…Sordidone, 8-chloro-5,7-dihydroxy-2,6-dimethoxychromone, the first isolated halochromone, was found in Lecanora lichen [32,33]. Some 6-and 8-mono-and 6,8-dichloro derivatives have been identified in Streptomyces strains [34][35][36] and recently three pestalochromones from Pestalotiopsis were isolated [37]. Halochromones also occur in higher plants, where 6-chloroapigenin was found in Equisetum arvense [38] and recently two 8-chloro-2-(2-phenylethyl)chromones were obtained from Aquilaria sinensis [39].…”

“…1). All the naturally-occurring derivatives are mono-or dichlorinated compounds and were mainly isolated from bacteria and fungi [32][33][34][35][36][37]. Sordidone, 8-chloro-5,7-dihydroxy-2,6-dimethoxychromone, the first isolated halochromone, was found in Lecanora lichen [32,33].…”