Isolation, Biosynthesis and Chemical Modifications of Rubterolones A–F: Rare Tropolone Alkaloids from <i>Actinomadura</i> sp. 5‐2

Guo, Huijuan; Benndorf, René; Leichnitz, Daniel; Klassen, Jonathan L.; Vollmers, John; Görls, Helmar; Steinacker, Matthias; Weigel, Christiane; Dahse, Hans‐Martin; Kaster, Anne‐Kristin; Beer, Z. Wilhelm de; Poulsen, Michael; Beemelmanns, Christine

doi:10.1002/chem.201701005

Cited by 47 publications

(50 citation statements)

References 39 publications

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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%

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Natural Products from Actinobacteria Associated with Fungus-Growing Termites

et al. 2018

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The chemical analysis of insect-associated Actinobacteria has attracted the interest of natural product chemists in the past years as bacterial-produced metabolites are sought to be crucial for sustaining and protecting the insect host. The objective of our study was to evaluate the phylogeny and bioprospecting of Actinobacteria associated with fungus-growing termites. We characterized 97 Actinobacteria from the gut, exoskeleton, and fungus garden (comb) of the fungus-growing termite Macrotermes natalensis and used two different bioassays to assess their general antimicrobial activity. We selected two strains for chemical analysis and investigated the culture broth of the axenic strains and fungus-actinobacterium co-cultures. From these studies, we identified the previously-reported PKS-derived barceloneic acid A and the PKS-derived rubterolones. Analysis of culture broth yielded a new dichlorinated diketopiperazine derivative and two new tetracyclic lanthipeptides, named rubrominins A and B. The discussed natural products highlight that insect-associated Actinobacteria are highly prolific natural product producers yielding important chemical scaffolds urgently needed for future drug development programs.

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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%

Natural Products from Actinobacteria Associated with Fungus-Growing Termites

et al. 2018

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“…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%

Biosynthetic access to the rare antiarose sugar via an unusual reductase-epimerase

et al. 2020

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“…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%

Natalenamides A–C, Cyclic Tripeptides from the Termite-Associated Actinomadura sp. RB99

Lee

et al. 2018

Molecules

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In recent years, investigations into the biochemistry of insect-associated bacteria have increased. When combined with analytical dereplication processes, these studies provide a powerful strategy to identify structurally and/or biologically novel compounds. Non-ribosomally synthesized cyclic peptides have a broad bioactivity spectrum with high medicinal potential. Here, we report the discovery of three new cyclic tripeptides: natalenamides A–C (compounds 1–3). These compounds were identified from the culture broth of the fungus-growing termite-associated Actinomadura sp. RB99 using a liquid chromatography (LC)/ultraviolet (UV)/mass spectrometry (MS)-based dereplication method. Chemical structures of the new compounds (1–3) were established by analysis of comprehensive spectroscopic methods, including one-dimensional (1H and 13C) and two-dimensional (1H-1H-COSY, HSQC, HMBC) nuclear magnetic resonance spectroscopy (NMR), together with high-resolution electrospray ionization mass spectrometry (HR-ESIMS) data. The absolute configurations of the new compounds were elucidated using Marfey’s analysis. Through several bioactivity tests for the tripeptides, we found that compound 3 exhibited significant inhibitory effects on 3-isobutyl-1-methylxanthine (IBMX)-induced melanin production. The effect of compound 3 was similar to that of kojic acid, a compound extensively used as a cosmetic material with a skin-whitening effect.

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Isolation, Biosynthesis and Chemical Modifications of Rubterolones A–F: Rare Tropolone Alkaloids from Actinomadura sp. 5‐2

Cited by 47 publications

References 39 publications

Natural Products from Actinobacteria Associated with Fungus-Growing Termites

Natural Products from Actinobacteria Associated with Fungus-Growing Termites

Biosynthetic access to the rare antiarose sugar via an unusual reductase-epimerase

Natalenamides A–C, Cyclic Tripeptides from the Termite-Associated Actinomadura sp. RB99

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