A Common Origin for Guanidinobutanoate Starter Units in Antifungal Natural Products

Hong, Hui; Fill, Taícia Pacheco; Leadlay, Peter F.

doi:10.1002/ange.201308136

Cited by 16 publications

(3 citation statements)

References 42 publications

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“…Recently, arginine was established as the putative precursor of bacterial macrocyclic guanidine polyketides. 41 Although a common biogenetic pathway for bacterial and marine sponge guanidine polyketides remains elusive at this point, there is increasing evidence of prokaryotic origin for many sponge metabolites, particularly those that are PKS or NRPS derived. 42 A similar hypothesis clearly deserves consideration for these marine sponge guanidine alkaloids.…”

Section: ■ Conclusionmentioning

confidence: 99%

Anti-parasitic Guanidine and Pyrimidine Alkaloids from the Marine Sponge Monanchora arbuscula

et al. 2015

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HPLC-UV-ELSD-MS-guided fractionation of the anti-parasitic extract obtained from the marine sponge Monanchora arbuscula, collected off the southeastern coast of Brazil, led to the isolation of a series of guanidine and pyrimidine alkaloids. The pyrimidines monalidine A (1) and arbusculidine A (7), as well as the guanidine alkaloids batzellamide A (8) and hemibatzelladines 9-11, represent new minor constituents that were identified by analysis of spectroscopic data. The total synthesis of monalidine A confirmed its structure. Arbusculidine A (7), related to the ptilocaulin/mirabilin/netamine family of tricyclic guanidine alkaloids, is the first in this family to possess a benzene ring. Batzellamide A (8) and hemibatzelladines 9-11 represent new carbon skeletons that are related to the batzelladines. Evaluation of the anti-parasitic activity of the major known metabolites, batzelladines D (12), F (13), L (14), and nor-L (15), as well as of synthetic monalidine A (1), against Trypanosoma cruzi and Leishmania infantum is also reported, along with a detailed investigation of parasite cell-death pathways promoted by batzelladine L (14) and norbatzelladine L (15).

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Section: ■ Conclusionmentioning

confidence: 99%

Anti-parasitic Guanidine and Pyrimidine Alkaloids from the Marine Sponge Monanchora arbuscula

et al. 2015

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“…Azl4 catalyzes the activation of 4-guanidinobutyric acid by addition of coenzyme A to the molecule. Azl5 consecutively loads 4-guanidinobutyryl-CoA onto the azalomycin F PKS [ 32 ]. In the second mutant strain ∆ azlH , the azlH gene, which encodes a part of the PKS [ 30 , 32 ], was deleted.…”

Section: Resultsmentioning

confidence: 99%

“…Azl5 consecutively loads 4-guanidinobutyryl-CoA onto the azalomycin F PKS [ 32 ]. In the second mutant strain ∆ azlH , the azlH gene, which encodes a part of the PKS [ 30 , 32 ], was deleted. Neither of the mutants ∆ azl4 ∆ azl5 and ∆ azlH produced detectable amounts of azalomycin F and both failed to decolorize C. reinhardtii (Fig.…”

Section: Resultsmentioning

confidence: 99%

Lichen-like association of Chlamydomonas reinhardtii and Aspergillus nidulans protects algal cells from bacteria

et al. 2020

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Organismal interactions within microbial consortia and their responses to harmful intruders remain largely understudied. An important step toward the goal of understanding functional ecological interactions and their evolutionary selection is the study of increasingly complex microbial interaction systems. Here, we discovered a tripartite biosystem consisting of the fungus Aspergillus nidulans, the unicellular green alga Chlamydomonas reinhardtii, and the algicidal bacterium Streptomyces iranensis. Genetic analyses and MALDI-IMS demonstrate that the bacterium secretes the algicidal compound azalomycin F upon contact with C. reinhardtii. In co-culture, A. nidulans attracts the motile alga C. reinhardtii, which becomes embedded and surrounded by fungal mycelium and is shielded from the algicide. The filamentous fungus Sordaria macrospora was susceptible to azalomycin F and failed to protect C. reinhardtii despite chemotactically attracting the alga. Because S. macrospora was susceptible to azalomycin F, this data imply that for protection the fungus needs to be resistant. Formation of the lichen-like association between C. reinhardtii and A. nidulans increased algal growth. The protection depends on the increased amounts of membrane lipids provided by resistant fungi, thereby generating a protective shelter against the bacterial toxin. Our findings reveal a strategy whereby algae survive lethal environmental algicides through cooperation with fungi.

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An Amidinohydrolase Provides the Missing Link in the Biosynthesis of Amino Marginolactone Antibiotics

et al. 2015

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A Common Origin for Guanidinobutanoate Starter Units in Antifungal Natural Products

Cited by 16 publications

References 42 publications

Anti-parasitic Guanidine and Pyrimidine Alkaloids from the Marine Sponge Monanchora arbuscula

Anti-parasitic Guanidine and Pyrimidine Alkaloids from the Marine Sponge Monanchora arbuscula

Lichen-like association of Chlamydomonas reinhardtii and Aspergillus nidulans protects algal cells from bacteria

An Amidinohydrolase Provides the Missing Link in the Biosynthesis of Amino Marginolactone Antibiotics

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