2017
DOI: 10.1002/chem.201701005
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Isolation, Biosynthesis and Chemical Modifications of Rubterolones A–F: Rare Tropolone Alkaloids from Actinomadura sp. 5‐2

Abstract: The discovery of six new, highly substituted tropolone alkaloids, rubterolones A-F, from Actinomadura sp. 5-2, isolated from the gut of the fungus-growing termite Macrotermes natalensis is reported. Rubterolones were identified by using fungus-bacteria challenge assays and a HRMS-based dereplication strategy, and characterised by NMR and HRMS analyses and by X-ray crystallography. Feeding experiments and subsequent chemical derivatisation led to a first library of rubterolone derivatives (A-L). Genome sequenci… Show more

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Cited by 46 publications
(50 citation statements)
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“…By tracing back the antifungal agents, comparative analysis of culture extracts resulted in the detection of predominant rubterolone derivatives ( 6 , 8 , and 9 ) [ 27 ] and a unique m/z signal pattern indicative for a dichlorinated natural product ( 11 ). Subsequent purification of co-cultivation and liquid culture extracts by semipreparative HPLC led to the isolation of the natural product banegasine ( 10 ) and the chlorinated natural product cyclo( N Me-L-3,5-dichlorotyrosine-Dhb) ( 11 ) ( Table S7 ) [ 36 ].…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…By tracing back the antifungal agents, comparative analysis of culture extracts resulted in the detection of predominant rubterolone derivatives ( 6 , 8 , and 9 ) [ 27 ] and a unique m/z signal pattern indicative for a dichlorinated natural product ( 11 ). Subsequent purification of co-cultivation and liquid culture extracts by semipreparative HPLC led to the isolation of the natural product banegasine ( 10 ) and the chlorinated natural product cyclo( N Me-L-3,5-dichlorotyrosine-Dhb) ( 11 ) ( Table S7 ) [ 36 ].…”
Section: Resultsmentioning
confidence: 99%
“…RB1 led to the isolation of termisoflavones A–C (termisoflavone A, 1 ) [ 26 ], and co-cultivation studies of Actinomadura sp. RB29 yielded a new group of tropolone derivatives named rubterolones (e.g., rubterolone D, 6 ) [ 27 ].…”
Section: Introductionmentioning
confidence: 99%
“…7 Aer the tropolone alkaloid rubrolone A produced by Streptomyces enchinoruber was rst reported in 1978 ( Fig. 1B), 8 the rubrolone family has since expanded with the identication of isatropolones 9 and rubterolones 10 from Actinomycete strains (Fig. 1B).…”
Section: Introductionmentioning
confidence: 93%
“…S8 †). 10 We therefore selected RblE and three other RubS3 homologues to test their functions. As expected, only RblE could convert 1 to 4 (Fig.…”
Section: Phylogenetic and Kinetic Analysis Of Rubs3 And Rblementioning
confidence: 99%
“…As part of our continuing endeavor to identify structurally novel and/or bioactive secondary metabolites from termite-associated microbes [ 14 , 15 , 16 , 17 ], we focused on the termite-associated Actinomadura sp. RB99, isolated from the fungus-growing termite, Macrotermes natalensis .…”
Section: Introductionmentioning
confidence: 99%