Nematodetoxic Aurovertin-Type Metabolites from a Root-Knot Nematode Parasitic Fungus<i>Pochonia chlamydosporia</i>

Niu, Xue‐Mei; Wang, Yanli; Chu, Yan-Sheng; Xue, Hua-Xi; Nan, Lijun; Wei, Lu-Xia; Mo, Ming-He; Zhang, Ke‐Qin

doi:10.1021/jf903259n

Cited by 64 publications

(64 citation statements)

References 34 publications

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“…Preliminary analysis of the NMR data also indicated that 2 possessed a similar skeleton to that of aurovertin I (14). 10 The same demethylation at C-16 (δ C 101.0) was concluded by the observed HMBC correlations from H-16 to C-14, C-15, C-17, and C-18 as the same to those of 1. In addition, a methyl carbon at δ C 26.5 (q) was assigned to be placed at O 6 .…”

Section: Resultssupporting

confidence: 58%

“…The structures of the known compounds 11-14 isolated were identified as aurovertin B, 5 aurovertin C, 22 aurovertin E, 8 and aurovertin I, 10 respectively, by comparison of their spectroscopic data with literature values. All aurovertins obtained from cultures of the basidiomycete A. confluens were yellow syrup, and could not obtain as crystals in diverse solution systems.…”

Section: Resultsmentioning

confidence: 99%

“…They have attracted considerable attention of chemists because of their actitivities as potent inhibitors of ATP synthesis and antitumor agents. [2][3][4][5][6][7] There have been nine aurovertins (A-I) structurally elucidated to date, 1,[8][9][10] while the relative and absolute configurations of aurovertin B were determined by spectroscopic analysis and total synthesis, respectively. 11,12 The absolute configuration of aurovertin F was determined by analysis of the CD spectrum recently.…”

Section: Introductionmentioning

confidence: 99%

“…9 It is deduced that aurovertin-type of compounds obtained in literature probably share the same absolute configuration on biosynthetic grounds. 10,13 During our continuing investigation of bioactive microbial secondary metabolites from the fungus, 8,[14][15][16][17][18][19][20][21][22][23] ten new aurovertin derivatives, named as aurovertins J-S (1-10), along with four previously reported aurovertins B, C, E and I (11)(12)(13)(14), were isolated from cultures of the basidiomycete Albatrellus confluens (Alb. et Schw.…”

Section: Introductionmentioning

confidence: 99%

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Ten new aurovertins from cultures of the basidiomycete Albatrellus confluens

Guo

Feng

et al. 2013

Nat. Prod. Bioprospect.

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Section: Resultssupporting

confidence: 58%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Ten new aurovertins from cultures of the basidiomycete Albatrellus confluens

Guo

Feng

et al. 2013

Nat. Prod. Bioprospect.

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“…A chemical study performed by Niu et al (2010) detected toxicity of two aurovetin compounds obtained from fermented mycelia extract of P. chlamydosporia on worms of P. redivivus, leading to body disintegration. This chemical support may explain the better performance of P. chlamydosporia on preying P. redivivus compared to H. thompsonii ability ( Table 2).…”

Section: Related To Than H Thomentioning

confidence: 99%

Hirsutella thompsonii and Pochonia chlamydosporia (Syn. Verticillium chlamydosporium) Mycelia Growth and Predation on Panagrellus redivivus

Lubian¹,

Martinha²,

Portz³

et al. 2017

JAS

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This research aimed to evaluate the nematophagous ability of 4077-Verticillium chlamydosporium var. chlamydosporium and 4466-Hirsutella thompsonii isolates and relate mycelia growth to the influence provoked by movement of nematodes. Each fungus grew in PDA (potato, dextrose, agar) medium end up to pure colonization. Then, ten mycelia plugs of 8 mm diameter were removed from colony borders and transferred to the center of ten Petri plates containing water-agar 2% medium. These plates were previously divided into four quadrants that received a number of 25 individuals of free-living nematodes (Panagrellus redivivus), composing a total of 100 nematodes per plate. Evaluations started after 24 hours of interaction, considering predation percentage and mycelia growth as stimuli of nematodes presence. Results showed growing predation performance to both isolates, being higher for V. chlamydosporium var. chlamydosporium since from first evaluation time, controlling more than 50% of nematode population initially added. Its predation potential was 39.2%, 38.4% and 48.35% higher than H. thompsonii at first, second and third evaluation day, respectively. Generally, nematodes did not stimulate mycelia growth, unless for H. thompsonii at 72 hours of interaction compared to control plates (without nematodes). Stress resulting from isolates transference from PDA to water-agar 2% resulted in sparse mycelia growth and it could have affected the predation performance of H. thompsonii that controlled nematodes in low levels throughout experiment. Independently of predation level, pictures revealed that both isolates has ability to control P. redivivus through hyphae penetration.

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Coordination of Polyketide Release and Multiple Detoxification Pathways for Tolerable Production of Fungal Mycotoxins

Cao

et al. 2022

Angewandte Chemie

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Efficient biosynthesis of microbial bioactive natural products (NPs) is beneficial for the survival of producers, while self-protection is necessary to avoid self-harm resulting from over-accumulation of NPs. The underlying mechanisms for the effective but tolerable production of bioactive NPs are not well understood. Herein, in the biosynthesis of two fungal polyketide mycotoxins aurovertin E (1) and asteltoxin, we show that the cyclases in the gene clusters promote the release of the polyketide backbone, and reveal that a signal peptide is crucial for their subcellular localization and full activity. Meanwhile, the fungus adopts enzymatic acetylation as the major detoxification pathway of 1. If intermediates are over-produced, the non-enzymatic shunt pathways work as salvage pathways to avoid excessive accumulation of the toxic metabolites for selfprotection. These findings provided new insight into the interplay of efficient backbone release and multiple detoxification strategies for the production of fungal bioactive NPs.Microbial natural products (NPs) have diverse bioactivities. They protect producers from predators, antagonize the growth of other species or hosts, and help to compete for the ecological niche. Some bioactive NPs, such as antibiotics and mycotoxins, are important to compete against other organisms within the same ecological space. Therefore, they are usually produced abundantly to maximize the competitive capacity of their producers. [1] It has been suggested that the efficient release of NP backbones from the enzymatic assembly lines has contributed significantly to the NP yields. [2] The main types of NPs in nature, such as polyketides (PKs), non-ribosomal peptides (NRPs), ribosomally synthesized and post-translationally modified peptides (RiPPs), and terpenes, are released through cyclization, hydrolysis and reduction. [3] These reactions can be catalyzed by assembly enzyme-fused domains or stand-alone enzymes, such as condensation domains, thioesterases, reductases and product templates. [4] In bacteria, PKs are also liberated by the stand-alone small cyclases, [5] which belong to the nuclear transport factor 2 (NTF2)-like superfamily SnoaL-2 proteins. These proteins have also been shown to act as postline tailoring enzymes, catalyzing highly selective [6+4] cycloaddition and polyether formation. [6] In fungi, an NTF2like superfamily protein has been reported to catalyze semipinacol rearrangement. [7] But their ability to act as cyclases is poorly characterized. Meanwhile, NP producers, have evolved exquisite strategies to avoid self-harm from bioactive NPs, [8] in particular if producers also contain the conserved target of NPs. These detoxification strategies include export by transporters or subcellular trafficking, neutralization by duplication of self-resistance target proteins, and NP inactivation by enzyme-catalyzed chemical modifications. [1b, 8, 9] However, the regulatory coordination between the backbone release and detoxification in fungi for the physiologically tolerable pr...

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Nematodetoxic Aurovertin-Type Metabolites from a Root-Knot Nematode Parasitic FungusPochonia chlamydosporia

Cited by 64 publications

References 34 publications

Ten new aurovertins from cultures of the basidiomycete Albatrellus confluens

Ten new aurovertins from cultures of the basidiomycete Albatrellus confluens

Hirsutella thompsonii and Pochonia chlamydosporia (Syn. Verticillium chlamydosporium) Mycelia Growth and Predation on Panagrellus redivivus

Coordination of Polyketide Release and Multiple Detoxification Pathways for Tolerable Production of Fungal Mycotoxins

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