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

Schneider, Kathrin; Graf, E.; Irran, Elisabeth; Nicholson, Graeme; Stainsby, Fiona M.; Goodfellow, Michael; Borden, Steffen A.; Keller, Simone; Süssmuth, Roderich D.; Fiedler, Hans‐Peter

doi:10.1038/ja.2008.50

Cited by 15 publications

(6 citation statements)

References 17 publications

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“…In most of the included studies (62.5%), at least one compound was isolated. In fact, in the studies of Schneider et al [ 51 ], Ma et al [ 56 ], Takaichi et al [ 53 ], and Lin et al [ 54 ], 3, 4, 7, and 12 metabolites were reported, respectively. The characteristics of the metabolites retrieved from the studies included in this review are presented in the following section.…”

Section: Resultsmentioning

confidence: 99%

Specialized Metabolism of Gordonia Genus: An Integrated Survey on Chemodiversity Combined with a Comparative Genomics-Based Analysis

Sánchez-Suárez

Díaz

Coy-Barrera

et al. 2022

BioTech

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Members of the phylum Actinomycetota (formerly Actinobacteria) have historically been the most prolific providers of small bioactive molecules. Although the genus Streptomyces is the best-known member for this issue, other genera, such as Gordonia, have shown interesting potential in their specialized metabolism. Thus, we combined herein the result of a comprehensive literature survey on metabolites derived from Gordonia strains with a comparative genomic analysis to examine the potential of the specialized metabolism of the genus Gordonia. Thirty Gordonia-derived compounds of different classes were gathered (i.e., alkaloids, amides, phenylpropanoids, and terpenoids), exhibiting antimicrobial and cytotoxic activities, and several were also isolated from Streptomyces (e.g., actinomycin, nocardamin, diolmycin A1). With the genome data, we estimated an open pan-genome of 57,901 genes, most of them being part of the cloud genome. Regarding the BGCs content, 531 clusters were found, including Terpenes, RiPP-like, and NRPS clusters as the most frequent clusters. Our findings demonstrated that Gordonia is a poorly studied genus in terms of its specialized metabolism production and potential applications. Nevertheless, given their BGCs content, Gordonia spp. are a valuable biological resource that could expand the chemical spectrum of the phylum Actinomycetota, involving novel BGCs for inspiring innovative outlines for synthetic biology and further use in biotechnological initiatives. Therefore, further studies and more efforts should be made to explore different environments and evaluate other bioactivities.

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Section: Resultsmentioning

confidence: 99%

Specialized Metabolism of Gordonia Genus: An Integrated Survey on Chemodiversity Combined with a Comparative Genomics-Based Analysis

Sánchez-Suárez

Díaz

Coy-Barrera

et al. 2022

BioTech

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“…Pseudomonas fragi ECS9, after PLC (AcOEt/cyclohexane/AcOH 70:30:2), afforded 12 α ‐hydroxy‐3‐oxopregna‐1,4‐diene‐20‐carboxylic acid (= bendigole A ; 8b ) . Yield: 80%.…”

Section: Experimental Partmentioning

confidence: 99%

“…). Bendigoles A – C, that showed binding affinity to androgen receptor, have been isolated as secondary metabolites of Gordonia australis Acta 2299 , a strain from activated sludge foam near Bendigo (Victoria, Australia).…”

Section: Introductionmentioning

confidence: 99%

Biotransformations of Bile Acids with Bacteria from Cayambe Slaughterhouse (Ecuador): Synthesis of Bendigoles

Costa

Rodríguez

Rugiero

et al. 2016

Chemistry & Biodiversity

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The biotransformations of cholic acid (1a), deoxycholic acid (1b), and hyodeoxycholic acid (1c) to bendigoles and other metabolites with bacteria isolated from the rural slaughterhouse of Cayambe (Pichincha Province, Ecuador) were reported. The more active strains were characterized, and belong to the genera Pseudomonas and Rhodococcus. Various biotransformation products were obtained depending on bacteria and substrates. Cholic acid (1a) afforded the 3-oxo and 3-oxo-4-ene derivatives 2a and 3a (45% and 45%, resp.) with P. mendocina ECS10, 3,12-dioxo-4-ene derivative 4a (60%) with Rh. erythropolis ECS25, and 9,10-secosteroid 6 (15%) with Rh. erythropolis ECS12. Bendigole F (5a) was obtained in 20% with P. fragi ECS22. Deoxycholic acid (1b) gave 3-oxo derivative 2b with P. prosekii ECS1 and Rh. erythropolis ECS25 (20% and 61%, resp.), while 3-oxo-4-ene derivative 3b was obtained with P. prosekii ECS1 and P. mendocina ECS10 (22% and 95%, resp.). Moreover, P. fragi ECS9 afforded bendigole A (8b; 80%). Finally, P. mendocina ECS10 biotransformed hyodeoxycholic acid (1c) to 3-oxo derivative 2c (50%) and Rh. erythropolis ECS12 to 6α-hydroxy-3-oxo-23,24-dinor-5β-cholan-22-oic acid (9c, 66%). Bendigole G (5c; 13%) with P. prosekii ECS1 and bendigole H (8c) with P. prosekii ECS1 and Rh. erythropolis ECS12 (20% and 16%, resp.) were obtained.

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“…Their ability includes but is not limited to degradation of various phthalic acid esters (PAEs), poly aromatic hydrocarbons (PAHs), alkylpyridines, 1,3,5-triazines and synthetic isoprene rubber (Drzyzga 2012). Production of extracellular polysaccharides (Ta-Chen et al 2008), carotenoids (Arenskötter et al 2004), steroids (Schneider et al 2008), and surfactants (Drzyzga 2012) has been documented. With major technological advances in genome sequencing, prediction and elucidation of the biosynthetic pathways of these novel compounds through genome mining is now possible.…”

Section: Introductionmentioning

confidence: 99%

In silico genome analysis reveals the metabolic versatility and biotechnology potential of a halotorelant phthalic acid esters degrading Gordonia alkanivorans strain YC-RL2

et al. 2019

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Members of genus Gordonia are known to degrade various xenobitics and produce secondary metabolites. The genome of a halotorelant phthalic acid ester (PAEs) degrading actinobacterium Gordonia alkanivorans strain YC-RL2 was sequenced using Biosciences RS II platform and Single Molecular Real-Time (SMRT) technology. The reads were assembled de novo by hierarchical genome assembly process (HGAP) algorithm version 2. Genes were annotated by NCBI Prokaryotic Genome Annotation Pipeline. The generated genome sequence was 4,979,656 bp with an average G+C content of 67.45%. Calculation of ANI confirmed previous classification that strain YC-RL2 is G. alkanivorans . The sequences were searched against KEGG and COG databases; 3132 CDSs were assigned to COG families and 1808 CDSs were predicted to be involved in 111 pathways. 95 of the KEGG annotated genes were predicted to be involved in the degradation of xenobiotics. A phthalate degradation operon could not be identified in the genome indicating that strain YC-RL2 possesses a novel way of phthalate degradation. A total of 203 and 22 CDSs were annotated as esterase/hydrolase and dioxygenase genes respectively. A total of 53 biosynthetic gene clusters (BGCs) were predicted by antiSMASH (antibiotics & Secondary Metabolite Analysis Shell) bacterial version 4.0. The genome also contained putative genes for heavy metal metabolism. The strain could tolerate 1 mM of Cd 2+ , Co 2+ , Cu 2+ , Ni 2+ , Zn 2+ , Mn 2+ and Pb 2+ ions. These results show that strain YC-RL2 has a great potential to degrade various xenobiotics in different environments and will provide a rich genetic resource for further biotechnological and remediation studies. Electronic supplementary material The online version of this article (10.1186/s13568-019-0733-5) contains supplementary material, which is available to authorized users.

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

Cited by 15 publications

References 17 publications

Specialized Metabolism of Gordonia Genus: An Integrated Survey on Chemodiversity Combined with a Comparative Genomics-Based Analysis

Specialized Metabolism of Gordonia Genus: An Integrated Survey on Chemodiversity Combined with a Comparative Genomics-Based Analysis

Biotransformations of Bile Acids with Bacteria from Cayambe Slaughterhouse (Ecuador): Synthesis of Bendigoles

In silico genome analysis reveals the metabolic versatility and biotechnology potential of a halotorelant phthalic acid esters degrading Gordonia alkanivorans strain YC-RL2

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