Abstract
Bendigoles A~C are the first secondary metabolites to be isolated from a member of the actinomycete genus Gordonia. They were detected in a culture filtrate extract of Gordonia australis Acta 2299 by HPLC-diode array analysis and characterized as new steroids by mass spectrometry and NMR experiments. Bendigole C show binding affinity to the human progesterone and A~C to androgen receptor but are inactive at mineralocorticoid and estrogen receptors. In in vitro transactivation studies bendigoles A and C showed moderate and weak androgenic activities.
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Fiedler H-P, Brunter C, Riedlinger J, Bull AT, Knutsen G, Goodfellow M, Jones AL, Maldonado L, Pathom-aree W, Beil W, Schneider K, Keller S, Süssmuth RD . Proximicin A, B and C, novel aminofuran antibiotic and anticancer compounds isolated from marine strains of the actinomycete Verrucosispora. J Antibiot 61: 158–163 ( 2008)
Fiedler H-P . Biosynthetic capacities of actinomycetes. 1. Screening for novel secondary metabolites by HPLC and UV-visible absorbance libraries. Nat Prod Lett 2: 119–128 ( 1993)
Stainsby FM, Soddell J, Seviour R, Upton J, Goodfellow M . Dispelling the “Nocardia amarae” myth: a phylogenetic and phenotypic study of mycolic acid-containing actinomycetes isolated from activated sludge foam. Water Sci Technol 46: 81–90 ( 2002)
Soddell JA, Stainsby FM, Eales KL, Seviour RJ, Goodfellow M . Gordonia defluvii sp. nov., an actinomycete isolated from activated sludge foam. Int J Syst Evol Microbiol 56: 2265–2269 ( 2006)
SCALE3 and CrysAlisRed (Version 1.171.29.10), Oxford Diffraction Ltd. Abingdon, Oxford, England ( 2006)
Sheldrick GM . SHELX97, Program package for the solution and refinement of crystal structures, Release 97-2, University of Göttingen, Germany ( 1997)
Fuhrmann U, Hess-Stumpp H, Cleve A, Neef G, Schwede W, Hoffmann J, Fritzemeier KH, Chwalisz K . Synthesis and biological activity of a novel, highly potent progesterone receptor antagonist. J Med Chem 43: 5010–5016 ( 2000)
Ourisson G, Nakatani Y . The terpenoid theory of the origin of cellular life: the evolution of terpenoids to cholesterol. Chem Biol 1: 11–23 ( 1994)
Kannenberg EL, Poralla K . Hopanoid biosynthesis and function in bacteria. Naturwissenschaften 86: 168–176 ( 1999)
Volkman JK . Sterols and other triterpenoids: source specificity and evolution of biosynthetic pathways. Org Geochem 36: 139–159 ( 2005)
Bird CW, Lynch JM, Pirt FJ, Reid WW, Brooks CJW, Middleditch BS . Steroids and squalene in Methylococcus capsulatus grown on methane. Nature 230: 473–474 ( 1971)
Bouvier P, Rohmer M, Benveniste P, Ourisson G . Δ 8(14)-steroids in the bacterium Methylococcus capsulatus. Biochem J 159: 267–271 ( 1976)
Patt TE, Hanson RS . Intracytoplasmic membrane, phospholipid, and sterol content of Methylobacterium organophilum cells grown under different conditions. J Bacteriol 134: 636–644 ( 1978)
Schouten S, Bowman JP, Rijpstra WIC, Sinninghe Damsté JS . Sterols in a psychrophilic methanotroph, Methylosphaera hansonii. FEMS Microbiol Lett 186: 193–195 ( 2000)
Kohl W, Gloe A, Reichenbach H . Steroids from the myxobacterium Nannocystis exedens. J Gen Microbiol 129: 1629–1635 ( 1983)
Bode HB, Zeggel B, Silakowski B, Wenzel SC, Reichenbach H, Müller R . Steroid biosynthesis in prokaryotes: identification of myxobacterial steroids and cloning of the first bacterial 2,3(S)-oxidosqualene cyclase from the myxobacterium Stigmatella aurantiaca. Mol Microbiol 47: 471–481 ( 2003)
Pearson A, Budin M, Brocks JJ . Phylogenetic and biochemical evidence for sterol synthesis in the bacterium Gemmata obscuriglobus. PNAS 100: 15352–15357 ( 2003)
Barnes PJ, Baty JD, Bilton RF, Mason AN . Degradation of deoxycholic acid by Pseudomonas sp. NCIB 10590. Tetrahedron 32: 89–93 ( 1976)
Kondo T, Yamamoto D, Yokota A, Suzuki A, Nagasawa H, Sakuda S . Gordonan, an acidic polysaccharide with cell aggregation-inducing activity in insect BM-N4 cells, produced by Gordonia sp. Biosci Biotechnol Biochem 64: 2388–2394 ( 2000)
3-[7aβ-Methyl-5-oxo-1β-(1α-methyl-2-oxopropyl)-3aαh-hexahydroindan-4α-yl]-propionic acid. ( Mitsubishi Chemical Industries Co., Ltd., Japan). Jpn Kokai Tokkyo Koho, 8 pp. Application: JP 79-70308 ( 1980)
Herath HMTB, Athukoralage PS . Triterpenoids of Gordonia dassanayakei. Nat Prod Sci 6: 102–105 ( 2000)
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Art. No. 43 in 'Biosynthetic Capacities of Actinomycetes'. Art. No. 42: See ref. 1
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Schneider, K., Graf, E., Irran, E. et al. Bendigoles A~C, New Steroids from Gordonia australis Acta 2299. J Antibiot 61, 356–364 (2008). https://doi.org/10.1038/ja.2008.50
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DOI: https://doi.org/10.1038/ja.2008.50
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