Cladomarine, a new anti-saprolegniasis compound isolated from the deep-sea fungus, Penicillium coralligerum YK-247

Takahashi, K.; Sakai, Kazunari; Nagano, Yuriko; Sakaguchi, Sakiko Orui; Lima, André Oliveira de Souza; Pellizari, Vivian H.; Iwatsuki, Masato; Takishita, Kiyotaka; Nonaka, Kenichi; Fujikura, Katsunori; Ōmura, Satoshi

doi:10.1038/ja.2017.58

Cited by 27 publications

(20 citation statements)

References 20 publications

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“…NMR experiments such as 1 H, COSY, ROESY, DEPT‐HSQC, and HMBC allowed the structures and relative configurations to be elucidated as discussed in the Supporting Information. Specifically, 3 was identical to cladomarine, 5 to 4′‐hydroxyasperentin, and 6 to 5′‐hydroxyasperentin …”

Section: Methodsmentioning

confidence: 99%

Cladosporin Derivatives Obtained by Biotransformation Provide Guidance for the Focused Derivatization of this Antimalarial Lead Compound

et al. 2018

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Cladosporin, a natural product known for decades, has recently been discovered to display potent and selective antiplasmodial activity by inhibition of lysyl‐tRNA synthetase. It was subjected to a panel of oxidative biotransformations with one fungal and two actinomycetes strains, as well as a triple mutant bacterial CYP102A1, yielding eight, mostly hydroxylated, derivatives. These new compounds covered a wide chemical space and contained two pairs of epimers in the tetrahydropyran ring. Although less potent than the parent compound, all analogues showed activity in a cell‐based synthetase assay, thus demonstrating uptake and on‐target activity in living cells with varying degrees of selectivity for the enzyme lysyl‐tRNA synthetase from Plasmodium falciparum and highlighting sites suitable for synthesis of future cladosporin analogues. Compounds with adjacent hydroxy functions showed different MS/MS fragmentation that can be explained in terms of an, in some cases, regioselective loss of water followed by a retro‐Diels–Alder reaction.

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Section: Methodsmentioning

confidence: 99%

Cladosporin Derivatives Obtained by Biotransformation Provide Guidance for the Focused Derivatization of this Antimalarial Lead Compound

et al. 2018

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“…Further chromatographic fractionation of the cultured broth led to the isolation of cladomarine ( 143 ) ( Figure 23 ) which showed selective antimicrobial activity against Saprolegnia parasitica and Pythium sp. sakari1 at a concentration of 10 μg/disc [ 50 ].…”

Section: Piezophilic Fungimentioning

confidence: 99%

Novel Natural Products from Extremophilic Fungi

Zhang

et al. 2018

Marine Drugs

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“…Likewise, cladomarine and quellenin, two antibiotics produced by the deep-sea fungus Penicillium coralligerum (YK-247) and Aspergillus sp. (strain YK-76), respectively, were shown to exhibit anti- Saprolegnia activity ( Takahashi et al, 2017 ). However, despite the discovery of these promising natural anti-oomycete compounds, their large-scale production has proven to be challenging and too expensive to be commercially viable.…”

Section: Introductionmentioning

confidence: 99%

Identification of Growth Inhibitors of the Fish Pathogen Saprolegnia parasitica Using in silico Subtractive Proteomics, Computational Modeling, and Biochemical Validation

et al. 2020

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Cladomarine, a new anti-saprolegniasis compound isolated from the deep-sea fungus, Penicillium coralligerum YK-247

Cited by 27 publications

References 20 publications

Cladosporin Derivatives Obtained by Biotransformation Provide Guidance for the Focused Derivatization of this Antimalarial Lead Compound

Cladosporin Derivatives Obtained by Biotransformation Provide Guidance for the Focused Derivatization of this Antimalarial Lead Compound

Novel Natural Products from Extremophilic Fungi

Identification of Growth Inhibitors of the Fish Pathogen Saprolegnia parasitica Using in silico Subtractive Proteomics, Computational Modeling, and Biochemical Validation

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