Precursor-directed fungal generation of novel halogenated chaetoglobosins with more preferable immunosuppressive action

Ge, Hui; Yan, Wei; Zhong, Guo; Luo, Qiong; Feng, Rui; Zang, Le Yun; Shen, Yan; Jiao, Rui Hua; Xu, Qiang; Tan, Ren Xiang

doi:10.1039/c0cc04183a

Cited by 30 publications

(32 citation statements)

References 11 publications

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“…This deduction could also be concluded by comparison of the cytotoxic activities between compounds 3 and 7 . In previous investigations, the known chaetoglobosins covered in the study had shown cytotoxicity against many different human cancer cell lines [15,16,27,28,29,32,33]. To our best knowledge, there were no previous reports on the cytotoxicity of these chaetoglobosins to MDA-MB-435, A549 and SGC-7901 cell lines, except compounds 8 and 9 , which were tested on the A549 cell line [28,29] with IC 50 values almost identical to our current results.…”

Section: Resultsmentioning

confidence: 99%

Bioactive Chaetoglobosins from the Mangrove Endophytic Fungus Penicillium chrysogenum

Huang

Chen

et al. 2016

Marine Drugs

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A novel chaetoglobosin named penochalasin I (1) with a unprecedented six-cyclic 6/5/6/5/6/13 fused ring system, and another new chaetoglobosin named penochalasin J (2), along with chaetoglobosins G, F, C, A, E, armochaetoglobosin I, and cytoglobosin C (3–9) were isolated from the culture of Penicillium chrysogenum V11. Their structures were elucidated by 1D, 2D NMR spectroscopic analysis and high resolution mass spectroscopic data. The absolute configuration of compounds 1 and 2 were determined by comparing the theoretical electronic circular dichroism (ECD) calculation with the experimental CD. Compound 1 was the first example, with a six-cyclic fused ring system formed by the connection of C-5 and C-2′ of the chaetoglobosin class. Compounds 5–8 remarkably inhibited the plant pathogenic fungus R. solani (minimum inhibitory concentrations (MICs) = 11.79–23.66 μM), and compounds 2, 6, and 7 greatly inhibited C. gloeosporioides (MICs = 23.58–47.35 μM), showing an antifungal activity higher than that of carbendazim. Compound 1 exhibited marked cytotoxicity against MDA-MB-435 and SGC-7901 cells (IC50 < 10 μM), and compounds 6 and 9 showed potent cytotoxicity against SGC-7901 and A549 cells (IC50 < 10 μM).

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Section: Resultsmentioning

confidence: 99%

Bioactive Chaetoglobosins from the Mangrove Endophytic Fungus Penicillium chrysogenum

Huang

Chen

et al. 2016

Marine Drugs

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“…However, biochemical evidences that confirm the direct incorporation of tryptamine as a precursor have not been reported [295]. Most, if not all, Chaetonium fungi in the Chaetomiaceae family produce L-tryptophan-derived alkaloid, but no P-S reaction-based secondary metabolite has been detected [296][297][298].…”

Section: Unnatural Compounds From Fungal Pictet-spengler Biosynthesismentioning

confidence: 99%

The Pictet-Spengler Reaction Updates Its Habits

et al. 2020

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The Pictet-Spengler reaction (P-S) is one of the most direct, efficient, and variable synthetic method for the construction of privileged pharmacophores such as tetrahydro-isoquinolines (THIQs), tetrahydro-β-carbolines (THBCs), and polyheterocyclic frameworks. In the lustro (five-year period) following its centenary birthday, the P-S reaction did not exit the stage but it came up again on limelight with new features. This review focuses on the interesting results achieved in this period (2011–2015), analyzing the versatility of this reaction. Classic P-S was reported in the total synthesis of complex alkaloids, in combination with chiral catalysts as well as for the generation of libraries of compounds in medicinal chemistry. The P-S has been used also in tandem reactions, with the sequences including ring closing metathesis, isomerization, Michael addition, and Gold- or Brønsted acid-catalyzed N-acyliminium cyclization. Moreover, the combination of P-S reaction with Ugi multicomponent reaction has been exploited for the construction of highly complex polycyclic architectures in few steps and high yields. The P-S reaction has also been successfully employed in solid-phase synthesis, affording products with different structures, including peptidomimetics, synthetic heterocycles, and natural compounds. Finally, the enzymatic version of P-S has been reported for biosynthesis, biotransformations, and bioconjugations.

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“…Komplexere Moleküle, für die PDB durchgeführt wurde, sind sieben pilzliche Systeme (Tabelle ): die Ergotpeptide ( Claviceps purpurea ), Aureobasidin, Asperlicin, das Immunsuppressivum Cyclosporin ( Tolypocladium inflatum ), Chateoglobosin ( Chaetomium sp. ) wie auch die CDPs Enniatin ( Fusarium sp. ) und Beauvericin ( Beauveriva bassiana ) .…”

Section: Erzeugung Von Strukturdiversität Durch Nrpssunclassified

Nicht‐ribosomale Peptidsynthese – Prinzipien und Perspektiven

Süßmuth

Mainz

2017

Angewandte Chemie

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Nicht‐ribosomale Peptidsynthetasen (NRPSs) sind große Multienzymmaschinerien, die zahlreiche Peptide mit enormer struktureller und funktionaler Diversität erzeugen. Unter diesen Produkten befinden sich mehr als 20 auf dem Markt befindliche Wirkstoffe, darunter Antibiotika (Penicillin, Vancomycin), antitumorale Medikamente (Bleomycin) und Immunsuppressiva (Cyclosporin). In den vergangenen Jahrzehnten haben biochemische sowie strukturbiologische Studien mechanistische Einblicke in die hochkomplexen NRPSs gewährt. Dieser Aufsatz fasst den aktuellen Kenntnisstand über die zugrundeliegenden Mechanismen von NRPSs zusammen und gibt einen Überblick über die Vielfalt ihrer Produkte. Ebenso behandelt werden die Probleme und Herausforderungen, die mit der Umprogrammierung von NRPS‐Systemen einhergehen. Das Potenzial einer solchen Umprogrammierung liegt begründet in einer nachhaltigen Generierung von Wirkstoffanaloga und neuen Substanzbibliotheken, die anderenfalls kaum zugänglich sind.

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Precursor-directed fungal generation of novel halogenated chaetoglobosins with more preferable immunosuppressive action

Abstract: Precursor-fed cultivation of endophytic Chaetomium globosum 1C51 afforded nine novel "unnatural" halogenated chaetoglobosins including those with more preferable immunosuppressive activity.

Cited by 30 publications

References 11 publications

Bioactive Chaetoglobosins from the Mangrove Endophytic Fungus Penicillium chrysogenum

Bioactive Chaetoglobosins from the Mangrove Endophytic Fungus Penicillium chrysogenum

The Pictet-Spengler Reaction Updates Its Habits

Nicht‐ribosomale Peptidsynthese – Prinzipien und Perspektiven

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