Chevalinulins A and B, Proangiogenic Alkaloids with a Spiro[bicyclo[2.2.2]octane-diketopiperazine] Skeleton from Deep-Sea Cold-Seep-Derived Fungus <i>Aspergillus chevalieri</i> CS-122

Yan, L.-L.; Li, Peihai; Li, Xiaoming; Yang, Sui-Qun; Liu, Kechun; Wang, Bin‐Gui

doi:10.1021/acs.orglett.2c00781

Cited by 45 publications

(43 citation statements)

References 20 publications

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“…The structure of chevalinulin A 6 , a metabolite of the deep-sea cold-seep-derived fungus Aspergillus chevalieri CS-122, was established by X-ray analysis. 6 It is suggested that the biosynthesis of chevalinulin A 6 involves a Diels–Alder cycloaddition of an indole diketopiperazine with a cyclohexadiene precursor.…”

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Hill

Sutherland

2022

Nat. Prod. Rep.

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Hill

Sutherland

2022

Nat. Prod. Rep.

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“…Cyclic dipeptides ring systems are achieved by the fusion of two α-amino acids, and the fungi are well-known primary producers of a diversity of cyclic dipeptides [ 1 – 4 ]. They have a wide range of biological activities, including antimicrobial, antiviral, anticancer, and proangiogenic activity [ 4 – 6 ]. This type of natural product contains numerous therapeutically promising compounds [ 7 ], such as plinabulin, the derivative of phenylahistin which was isolated from the fungus Aspergillus ustus [ 8 ], plinabulin has been advanced to Phase III clinical trials as an antitumor drug candidate [ 9 ].…”

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Efficient production of a cyclic dipeptide (cyclo-TA) using heterologous expression system of filamentous fungus Aspergillus oryzae

Han

Sui

et al. 2022

Microb Cell Fact

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Background Cyclic dipeptides are an important class of natural products owing to their structural diversity and biological activities. In fungi, the cyclo-ring system is formed through the condensation of two α-amino acids via non-ribosomal peptide synthetase (NRPS). However, there are few investigations on the functional identification of this enzyme. Additionally, information on how to increase the production of cyclic dipeptide molecules is relatively scarce. Results We isolated the Eurotium cristatum NWAFU-1 fungus from Jing-Wei Fu brick tea, whose fermentation metabolites contain echinulin-related cyclic dipeptide molecules. We cloned the cirC gene, encoding an NRPS, from E. Cristatum NWAFU-1 and transferred it into the heterologous host Aspergillus oryzae. This transformant produced a novel metabolite possessing an l-tryptophan-l-alanine cyclic dipeptide backbone (Cyclo-TA). Based on the results of heterologous expression and microsomal catalysis, CriC is the first NRPS characterized in fungi that catalyzes the formation of a cyclic dipeptide from l-tryptophan and l-alanine. After substrate feeding, the final yield reached 34 mg/L. In this study, we have characterized a novel NRPS and developed a new method for cyclic dipeptide production. Conclusions In this study we successfully expressed the E. Cristatum NWAFU-1 criC gene in A. oryzae to efficiently produce cyclic dipeptide compounds. Our findings indicate that the A. oryzae heterologous expression system constitutes an efficient method for the biosynthesis of fungal Cyclic dipeptides.

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“…Seven of these compounds are C7-alkylated salicylaldehyde derivatives and nine are prenylated indole alkaloids. Interestingly, two indole DKPs were reported to be generated by the deep-sea cold-seep-derived fungus Aspergillus chevalieri CS-122 ( Yan et al, 2022 ).…”

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confidence: 99%

Indole Diketopiperazine Alkaloids Isolated From the Marine-Derived Fungus Aspergillus chevalieri MCCC M23426

Xia

Guan

et al. 2022

Front. Microbiol.

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Two new indole diketopiperazines (1–2) obtained from the fermentation culture of a deep-sea-derived fungus Aspergillus chevalieri MCCC M23426, were characterized, together with nine biogenetic related compounds (3–11). The structures of 1–2 were assigned based on NMR, MS, NMR calculation, DP4+ analysis, and ECD calculation. The bioactive assay showed that compounds 1, 5–7 significantly inhibited the growth of Staphylococcus aureus. Meanwhile, compound 8 potently reduced the cell viability of gastric cancer cell MKN1 with an IC50 value of 4.6 μM.

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Chevalinulins A and B, Proangiogenic Alkaloids with a Spiro[bicyclo[2.2.2]octane-diketopiperazine] Skeleton from Deep-Sea Cold-Seep-Derived Fungus Aspergillus chevalieri CS-122

Cited by 45 publications

References 20 publications

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Hot off the Press

Efficient production of a cyclic dipeptide (cyclo-TA) using heterologous expression system of filamentous fungus Aspergillus oryzae

Indole Diketopiperazine Alkaloids Isolated From the Marine-Derived Fungus Aspergillus chevalieri MCCC M23426

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