Biomimetic Total Synthesis of (±)‐Homodimericin A

Ma, Dawei; Liu, Yangbin; Wang, Zhang

doi:10.1002/anie.201702775

Cited by 22 publications

(22 citation statements)

References 46 publications

(6 reference statements)

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“…harzianum WC13 in 2016 . 8- epi -Homodimericin A was first obtained and reported during the total synthesis of homodimericin A . As far as we know, 8- epi -homodimericin A was isolated from fungal culture for the first time in this study.…”

Section: Resultsmentioning

confidence: 74%

ThpacC Acts as a Positive Regulator of Homodimericin A Biosynthesis and Antifungal Activities of Trichoderma harzianum 3.9236

Wei

et al. 2021

J. Agric. Food Chem.

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The Pal/Rim pathway and its key transcription factor PacC play important roles in fungal adaptation to ambient pH regarding growth, secondary metabolism, and virulence. However, the effect of PacC on the secondary metabolism of the important biocontrol fungus Trichoderma harzianum remains elusive. To answer this question, ThpacC deletion (KO-ThpacC) and overexpression (OE-ThpacC) mutants of T. harzianum 3.9236 were constructed. Transcriptomic analysis of T. harzianum and KO-ThpacC suggested that ThpacC acted as both a positive and a negative regulator for secondary metabolite (SM) production. Further investigation revealed that deletion of ThpacC abolished homodimericin A and 8-epi-homodimericin A production. Moreover, ThpacC plays a role in the antagonism of T. harzianum against Sclerotinia sclerotiorum. 8-epi-Homodimericin A demonstrated moderate inhibitory activity against S. sclerotiorum. Our results contribute to a deeper understanding of the ThpacC function on SM production and the antifungal activity of T. harzianum.

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Section: Resultsmentioning

confidence: 74%

ThpacC Acts as a Positive Regulator of Homodimericin A Biosynthesis and Antifungal Activities of Trichoderma harzianum 3.9236

Wei

et al. 2021

J. Agric. Food Chem.

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“…The bafilomycins are known potent and specific inhibitors of fungal vacuolar-type H + -ATPases, which when inhibited causes increases in both cellular pH and oxidative stress (Werner et al 1984 ; Dröse and Altendorf 1997 ). We suggest that the production of homodimericin A, which requires a six-electron non-enzymatic oxidation from its starting material (Mevers et al 2016 ; Ma et al 2017 ), would relieve the oxidative stress caused by bafilomycin C1, while t22-azaphilone neutralizes the active threat by inhibiting the growth of Streptomyces sp. 4231 and thus ceasing the production of bafilomycin C1.…”

Section: Discussionmentioning

confidence: 99%

Chemical Interaction among Termite-Associated Microbes

Mevers

Chouvenc

et al. 2017

J Chem Ecol

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Bacteria and fungi in shared environments compete with one another for common substrates, and this competition typically involves microbially-produced small molecules. An investigation of one shared environmental niche, the carton material of the Formosan subterranean termite Coptotermes formosanus, identified the participants on one of these molecular exchanges. Molecular characterization of several termite-associated actinobacteria strains identified eleven known antimicrobial metabolites that may aid in protecting the C. formosanus colony from pathogenic fungal infections. One particular actinobacterial-derived small molecule, bafilomycin C1, elicited a strong chemical response from Trichoderma harzianum, a common soil saprophyte. Upon purification and structure elucidation, three major fungal metabolites were identified, t22-azaphilone, cryptenol, and homodimericin A. Both t22-azaphilone and homodimericin A are strongly upregulated, 123- and 38-fold, respectively, when exposed to bafilomycin C1, suggesting each play a role in defending T. harzianum from the toxic effect of bafilomycin C1.Electronic supplementary materialThe online version of this article (10.1007/s10886-017-0900-6) contains supplementary material, which is available to authorized users.

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“…(2006) – antagonize Streptomyces sp. 4231 by antibiosis (Mevers et al ., 2016; Ma et al ., 2017). Our data here provided extra evidence against this argument.…”

Section: Discussionmentioning

confidence: 99%

Azaphilones biosynthesis complements the defence mechanism of Trichoderma guizhouense against oxidative stress

Pang

Sun

et al. 2020

Environmental Microbiology

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Summary Filamentous fungi are known as producers of a large array of diverse secondary metabolites (SMs) that aid in securing their environmental niche. Here, we demonstrated that the SMs have an additional role in fungal defence against other fungi: Trichoderma guizhouense, a mycoparasite, is able to antagonize Fusarium oxysporum f. sp. cubense race 4 (Foc4) by forming aerial hyphae that kill the host with hydrogen peroxide. At the same time, a gene cluster comprising two polyketide synthases is strongly expressed. Using functional genetics, we characterized this cluster and identified its products as azaphilones (termed as trigazaphilones). The trigazaphilones were found lacking of antifungal toxicity but exhibited high radical scavenging activities. The antioxidant property of trigazaphilones was in vivo functional under various tested conditions of oxidative stress. Thus, we conclude that the biosynthesis of trigazaphilones serves as a complementary antioxidant mechanism and defends T. guizhouense against the hydrogen peroxide that it produces to combat other fungi like Foc4.

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Biomimetic Total Synthesis of (±)‐Homodimericin A

Cited by 22 publications

References 46 publications

ThpacC Acts as a Positive Regulator of Homodimericin A Biosynthesis and Antifungal Activities of Trichoderma harzianum 3.9236

ThpacC Acts as a Positive Regulator of Homodimericin A Biosynthesis and Antifungal Activities of Trichoderma harzianum 3.9236

Chemical Interaction among Termite-Associated Microbes

Azaphilones biosynthesis complements the defence mechanism of Trichoderma guizhouense against oxidative stress

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