Arthrobotrisins A–C, Oligosporons from the Nematode-Trapping Fungus <i>Arthrobotrys oligospora</i>

Wei, Lu-Xia; Zhang, Huixiang; Tan, Jun; Chu, Yan-Sheng; Li, Nan; Xue, Hua-Xi; Wang, Yanli; Niu, Xue‐Mei; Zhang, Ying; Zhang, Ke‐Qin

doi:10.1021/np200187z

Cited by 44 publications

(58 citation statements)

References 8 publications

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“…Strong activity was observed against B. subtilis , but the activity against two other Bacillus species and Staphylococcus aureus were moderate in comparison to the bacteriostatic standard chloramphenicol. None of the arthrobotrisins displayed nematicidal activity against the free-living nematode Panagrellus redivivus (Wei et al 2011 ).…”

Section: Metabolites Produced By Nematophagous Fungimentioning

confidence: 99%

Metabolites from nematophagous fungi and nematicidal natural products from fungi as an alternative for biological control. Part I: metabolites from nematophagous ascomycetes

Degenkolb

Vilcinskas

2015

Appl Microbiol Biotechnol

131

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Plant-parasitic nematodes are estimated to cause global annual losses of more than US$ 100 billion. The number of registered nematicides has declined substantially over the last 25 years due to concerns about their non-specific mechanisms of action and hence their potential toxicity and likelihood to cause environmental damage. Environmentally beneficial and inexpensive alternatives to chemicals, which do not affect vertebrates, crops, and other non-target organisms, are therefore urgently required. Nematophagous fungi are natural antagonists of nematode parasites, and these offer an ecophysiological source of novel biocontrol strategies. In this first section of a two-part review article, we discuss 83 nematicidal and non-nematicidal primary and secondary metabolites found in nematophagous ascomycetes. Some of these substances exhibit nematicidal activities, namely oligosporon, 4′,5′-dihydrooligosporon, talathermophilins A and B, phomalactone, aurovertins D and F, paeciloxazine, a pyridine carboxylic acid derivative, and leucinostatins. Blumenol A acts as a nematode attractant. Other substances, such as arthrosporols and paganins, play a decisive role in the life cycle of the producers, regulating the formation of reproductive or trapping organs. We conclude by considering the potential applications of these beneficial organisms in plant protection strategies.

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Section: Metabolites Produced By Nematophagous Fungimentioning

confidence: 99%

Metabolites from nematophagous fungi and nematicidal natural products from fungi as an alternative for biological control. Part I: metabolites from nematophagous ascomycetes

Degenkolb

Vilcinskas

2015

Appl Microbiol Biotechnol

131

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“…In 1994, linoleic acid was reported to be a putative nematicidal compound from several nematophagous fungi ( 22 ). At the same time, a unique class of hybrid oligosporon metabolites found to be chemotaxonomic markers was reported from different strains of a model species of Arthrobotrys oligospora isolated from The Netherlands ( 23 ), from Australia ( 24 ), and, later, from China ( 25 , 26 ). These known metabolites from A. oligospora are nonvolatile compounds and exhibit several biological activities, including moderate antibacterial properties and significant autoregulatory effects on the formation of conidiophores and hyphal fusions in A. oligospora ( 26 , 27 ).…”

Section: Introductionmentioning

confidence: 97%

Integrated Metabolomics and Morphogenesis Reveal Volatile Signaling of the Nematode-Trapping Fungus Arthrobotrys oligospora

Wang

Xue

et al. 2018

Appl Environ Microbiol

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The adjustment of metabolic patterns is fundamental to fungal biology and plays vital roles in adaptation to diverse ecological challenges. Nematode-trapping fungi can switch their lifestyle from saprophytic to pathogenic by developing specific trapping devices induced by nematodes to infect their prey as a response to nutrient depletion in nature. However, the chemical identity of the specific fungal metabolites used during the switch remains poorly understood. We hypothesized that these important signal molecules might be volatile in nature. Gas chromatography-mass spectrometry was used to carry out comparative analysis of fungal metabolomics during the saprophytic and pathogenic lifestyles of the model species Arthrobotrys oligospora. Two media commonly used in research on this species, cornmeal agar (CMA) and potato dextrose agar (PDA), were chosen for use in this study. The fungus produced a small group of volatile furanone and pyrone metabolites that were associated with the switch from the saprophytic to the pathogenic stage. A. oligospora fungi grown on CMA tended to produce more traps and employ attractive furanones to improve the utilization of traps, while fungi grown on PDA developed fewer traps and used nematode-toxic furanone metabolites to compensate for insufficient traps. Another volatile pyrone metabolite, maltol, was identified as a morphological regulator for enhancing trap formation. Deletion of the gene AOL_s00079g496 in A. oligospora led to increased amounts of the furanone attractant (2-fold) in mutants and enhanced the attractive activity (1.5-fold) of the fungus, while it resulted in decreased trap formation. This investigation provides new insights regarding the comprehensive tactics of fungal adaptation to environmental stress, integrating both morphological and metabolomic mechanisms.IMPORTANCE Nematode-trapping fungi are a unique group of soil-living fungi that can switch from the saprophytic to the pathogenic lifestyle once they come into contact with nematodes as a response to nutrient depletion. In this study, we investigated the metabolic response during the switch and the key types of metabolites involved in the interaction between fungi and nematodes. Our findings indicate that A. oligospora develops multiple and flexible metabolic tactics corresponding to different morphological responses to nematodes. A. oligospora can use similar volatile furanone and pyrone metabolites with different ecological functions to help capture nematodes in the fungal switch from the saprophytic to the pathogenic lifestyle. Furthermore, studies with A. oligospora mutants with increased furanone and pyrone metabolites confirmed the results. This investigation reveals the importance of volatile signaling in the comprehensive tactics used by nematode-trapping fungi, integrating both morphological and metabolomic mechanisms.

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“…[33] In current study, the isolated compounds were tested for several bioactivities, including cytotoxicity, anti-inflammation, anti-allergy, antiangiogenesis and nematocidal activities. However, the results demonstrated that the isolates (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12) had no significant activities in cytotoxic, anti-inflammatory, and anti-angiogenesis assays. And 1 was inactive in cytotoxic, anti-allergic and nematocidal assays.…”

Section: Resultsmentioning

confidence: 98%

“…[10,11,12,13] In past, secondary metabolites, oligosporon, oligosporol B, 4',5'-dihydrooligosporon, hydroxyoligosporon, 10',11'-epoxyoligosporon, 4',5'-dihydro-oligosporol B, arthrobotrisins A, B, C and arthrosporols A, B, C were reported from other species of this genus. [10,11,14] However, to the best of our knowledge, there has been no chemical and biological investigation on the species of Arthrobotrys foliicola yet. In addition, this fungus was successfully modulated by epigenetic manipulation in our preliminary evaluation.…”

Section: Introductionmentioning

confidence: 99%

“…The compound which was identified as 4-ethyl-7-hydroxy-8methyl-2H-chromen-2-one (1) was isolated from nature for the first time. Moreover, the investigation on the remaining part of the HPLC profile led to the separation of 6-ethyl-2,4dihydroxy-3-methylbenzaldehyde (2) and ten 2,5-diketopiperazine compounds (3)(4)(5)(6)(7)(8)(9)(10)(11)(12). The structures of isolates were deduced by their mass and NMR spectroscopic data.…”

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confidence: 99%

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Epigenetic Manipulation Induces the Production of Coumarin‐Type Secondary Metabolite from Arthrobotrys foliicola

Hsueh

et al. 2019

Israel Journal of Chemistry

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Pursuing epigenetic manipulation approach in fungi led to the isolation of an unusual coumarin metabolite from fungi. An addition of the histone deacetylase inhibitor, suberohydroxamic acid (SBHA), to the culture medium of Arthrobotrys foliicola induced production of the coumarin‐type secondary metabolite represented by a single intensive peak in the HPLC profile of the ethyl acetate extract. The compound which was identified as 4‐ethyl‐7‐hydroxy‐8‐methyl‐2H‐chromen‐2‐one (1) was isolated from nature for the first time. Moreover, the investigation on the remaining part of the HPLC profile led to the separation of 6‐ethyl‐2,4‐dihydroxy‐3‐methylbenzaldehyde (2) and ten 2,5‐diketopiperazine compounds (3–12). The structures of isolates were deduced by their mass and NMR spectroscopic data. The coumarin‐type secondary metabolite (1) with peculiar smell induced by epigenetic stimulation is found for the first time in the Arthrobotrys species and the family Orbiliaceae. We evaluated 1 for the cytotoxic, anti‐inflammatory, anti‐allergic and nematocidal activities, however, it was found inactive.

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Arthrobotrisins A–C, Oligosporons from the Nematode-Trapping Fungus Arthrobotrys oligospora

Cited by 44 publications

References 8 publications

Metabolites from nematophagous fungi and nematicidal natural products from fungi as an alternative for biological control. Part I: metabolites from nematophagous ascomycetes

Metabolites from nematophagous fungi and nematicidal natural products from fungi as an alternative for biological control. Part I: metabolites from nematophagous ascomycetes

Integrated Metabolomics and Morphogenesis Reveal Volatile Signaling of the Nematode-Trapping Fungus Arthrobotrys oligospora

Epigenetic Manipulation Induces the Production of Coumarin‐Type Secondary Metabolite from Arthrobotrys foliicola

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