Novoamauromine and ent-Cycloechinulin: Two New Diketopiperazine Derivatives from Aspergillus novofumigatus

Ishikawa, Kazuki; Hosoe, Tomoo; Itabashi, Takeshi; Wakana, Daigo; Takizawa, Kayoko; Yaguchi, Takashi; Kawai, Ken‐ichi

doi:10.1248/cpb.58.717

Cited by 27 publications

(20 citation statements)

References 14 publications

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“…Novoamauromine ( 128 ) was obtained from Aspergillus novofumitatus CBS117520. This compound had inhibitory activity on the cell proliferation of A549, HeLa, LNCap (human prostate carcinoma cells) [ 59 ].…”

Section: Tryptophan–tryptophan Cyclodipeptidesmentioning

confidence: 99%

Structural Diversity and Biological Activities of the Cyclodipeptides from Fungi

Wang

Zhang

et al. 2017

Molecules

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Cyclodipeptides, called 2,5-diketopiperazines (2,5-DKPs), are obtained by the condensation of two amino acids. Fungi have been considered to be a rich source of novel and bioactive cyclodipeptides. This review highlights the occurrence, structures and biological activities of the fungal cyclodipeptides with the literature covered up to July 2017. A total of 635 fungal cyclodipeptides belonging to the groups of tryptophan-proline, tryptophan-tryptophan, tryptophan–Xaa, proline–Xaa, non-tryptophan–non-proline, and thio-analogs have been discussed and reviewed. They were mainly isolated from the genera of Aspergillus and Penicillium. More and more cyclodipeptides have been isolated from marine-derived and plant endophytic fungi. Some of them were screened to have cytotoxic, phytotoxic, antimicrobial, insecticidal, vasodilator, radical scavenging, antioxidant, brine shrimp lethal, antiviral, nematicidal, antituberculosis, and enzyme-inhibitory activities to show their potential applications in agriculture, medicinal, and food industry.

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Section: Tryptophan–tryptophan Cyclodipeptidesmentioning

confidence: 99%

Structural Diversity and Biological Activities of the Cyclodipeptides from Fungi

Wang

Zhang

et al. 2017

Molecules

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“…It is an isomer of viridamine 88 [129] and interferes with the mitochondrial respiratory chain [130]. Also no biological activities are known for the tryptophan-derived isomeric novoamauromine 89 and ent-cycloechinulin 90 which were isolated from Aspergillus novofumigatus [131]. From the fungus Chromocleista species six diketopiperazines of unreported biological activities were identified: the novel epimeric diketopiperazines cyclo(L-Phe-2-OH-Pro) 91 and 92 and the known compounds cyclo(L-Leu-L- [132].…”

Section: Discussionmentioning

confidence: 99%

Antimicrobial and Biofilm Inhibiting Diketopiperazines

Carvalho

Abraham²

2012

CMC

136

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“…The 2‐dimethyl‐3‐methyl‐azetidine ring on 1 is fused to the HPI moiety, which is unprecedented in nature and is challenging to construct by chemical synthesis. The azocine ring can be found in some natural products, such as cycloechinulins and versicamides …”

Section: Figurementioning

confidence: 99%

Biosynthesis of Complex Indole Alkaloids: Elucidation of the Concise Pathway of Okaramines

Lai

Hewage

et al. 2017

Angewandte Chemie

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The okaramines are a class of complex indole alkaloids isolated from Penicillium and Aspergillus species. Their potent insecticidal activity arises from selectively activating glutamate‐gated chloride channels (GluCls) in invertebrates, not affecting human ligand‐gated anion channels. Okaramines B (1) and D (2) contain a polycyclic skeleton, including an azocine ring and an unprecedented 2‐dimethyl‐3‐methyl‐azetidine ring. Owing to their complex scaffold, okaramines have inspired many total synthesis efforts, but the enzymology of the okaramine biosynthetic pathway remains unexplored. Here, we identified and characterized the biosynthetic gene cluster (oka) of 1 and 2, then elucidated the pathway with target gene inactivation, heterologous reconstitution, and biochemical characterization. Notably, we characterized an α‐ketoglutarate‐dependent non‐heme FeII dioxygenase that forged the azetidine ring on the okaramine skeleton.

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Novoamauromine and ent-Cycloechinulin: Two New Diketopiperazine Derivatives from Aspergillus novofumigatus

Cited by 27 publications

References 14 publications

Structural Diversity and Biological Activities of the Cyclodipeptides from Fungi

Structural Diversity and Biological Activities of the Cyclodipeptides from Fungi

Antimicrobial and Biofilm Inhibiting Diketopiperazines

Biosynthesis of Complex Indole Alkaloids: Elucidation of the Concise Pathway of Okaramines

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