Article

Bendigoles A~C, New Steroids from Gordonia australis Acta 2299†

Institut für Chemie, Technische Universität Berlin, Germany.
The Journal of Antibiotics (Impact Factor: 2.04). 07/2008; 61(6):356-64. DOI: 10.1038/ja.2008.50
Source: PubMed

ABSTRACT Bendigoles A approximately 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 approximately 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.

Download full-text

Full-text

Available from: Hans-Peter Fiedler, May 24, 2015
0 Followers
 · 
296 Views
  • Source
    • "Bendigoles are the first secondary metabolites to be isolated from a member of the actinomycete genus Gordonia and were detected in the culture filtrate extract of G. australis. One of these steroid compounds, Bendigole C, showed binding affinity to the human progesterone and Bendigoles A-C to the androgen receptor, but are inactive at mineralocorticoid and estrogen receptors (Schneider et al., 2008). "
    [Show abstract] [Hide abstract]
    ABSTRACT: This review about the genus Gordonia provides a current overview of recent research on a young genus that was introduced in the year 1997 ( Stackebrandt et al., 1997 ). This emerging genus has attracted increasing environmental, industrial, biotechnological and medical interest during the last few years, in particular due to the capabilities of its members to degrade, transform, and synthesize organic compounds as well as to the pathogenic effects that have been described in many case studies. The number of publications about Gordonia has increased significantly after the year 2004 (the year of the first Gordonia review published by Arenskötter et al.) describing 13 new validly published species (type strains), many newly described physiological and metabolic capabilities, new patent applications and many new case reports of bacterial infections. Members of the genus Gordonia are widely distributed in nature and it is therefore important to unravel the species richness and metabolic potential of gordoniae in future studies to demonstrate their environmental impact especially on the degradation of persistent organic compounds and their ecological participation in the carbon cycle of organic material in soil and water. This review summarizes mainly the current state of importance and potential of the members of this genus for the environmental and biotechnological industry ("the strengthsâ) and briefly its pathogenic impact to humans ("the weaknessesâ).
    Critical Reviews in Microbiology 05/2012; 38(4):300-16. DOI:10.3109/1040841X.2012.668134 · 6.09 Impact Factor
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
    ChemInform 12/2008; 39(50). DOI:10.1002/chin.200850193
  • [Show abstract] [Hide abstract]
    ABSTRACT: Marine derived actinomycetes have become an important source of bioactive natural products. Here we report the structure and bioactivity of the bendigoles D-F (1-3), 3-keto sterols isolated from the new marine sponge derived bacterium, Actinomadura sp. SBMs009. The isolation of these compounds was guided by a novel high-content screen for NF-κB and glucocorticoid receptor (GR) activity, and cytotoxicity assays. The structures of 1-3 were determined by detailed analysis of NMR, MS, and single crystal X-ray diffraction data. Interestingly, 1 displayed cytotoxicity against the L929 (mouse fibroblast) cell line with an IC(50) approximated to 30 μM and was the most active inhibitor of GR-translocation, while 3 was the most effective inhibitor of NF-κB nuclear translocation with an IC(50) of 71 μM.
    Bioorganic & medicinal chemistry 05/2011; 19(22):6570-5. DOI:10.1016/j.bmc.2011.05.044 · 2.95 Impact Factor
Show more