Anthelmintic activity of 3,6-dibenzyl-2,5-dioxopiperazine, cyclo(L-Phe-L-Phe)

Walchshofer, Nadia; Sarciron, Marie‐Elisabeth; Garnier, François; Delatour, P.; Petavy, A.F.; Pâris, J.

doi:10.1007/bf01373425

Cited by 15 publications

(11 citation statements)

References 11 publications

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“…Cyclo( l -Phe– l -Phe) ( 357 ) originally isolated from Penicillium nigricans was also isolated from a marine mangrove endophytic fungus [ 171 ], and exhibited good anthelmintic activity against Hymenolepis nata and Schistosoma mansoni in mice [ 172 ].…”

Section: Non-tryptophan–non-proline 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: Non-tryptophan–non-proline Cyclodipeptidesmentioning

confidence: 99%

Structural Diversity and Biological Activities of the Cyclodipeptides from Fungi

Wang

Zhang

et al. 2017

Molecules

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“…Cyclo( L -Phe- L -Phe) is of special interest among DKPs in foods and beverages because it is found not only in chicken essence [11] but also in some commercial chicken soups such as bouillon cubes and powders. Besides its known biological activities (antifungal [31] and anthelmintic activities [32]), we have now shown that cyclo( L -Phe- L -Phe) is a dual inhibitor of the SERT and ACh that has both antidepression and antiamnesic effects in animal models. Animal studies have demonstrated that post-training SSRI administration improves memory more than that of pre-training administration [33].…”

Section: Discussionmentioning

confidence: 99%

A DKP Cyclo(L-Phe-L-Phe) Found in Chicken Essence Is a Dual Inhibitor of the Serotonin Transporter and Acetylcholinesterase

Tsuruoka¹,

Beppu

Kôda

et al. 2012

PLoS ONE

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Diketopiperazines (DKPs) are naturally-occurring cyclic dipeptides with a small structure and are found in many organisms and in large amounts in some foods and beverages. We found that a chicken essence beverage, which is popular among Southeast Asians as a traditional remedy and a rich source of DKPs, inhibited the serotonin transporter (SERT) and suppressed serotonin uptake from rat brain synaptosomes, which prompted us to isolate and identify the active substance(s). We purified a SERT inhibitor from the chicken essence beverage and identified it as the DKP cyclo(L-Phe-L-Phe). Interestingly, it was a naturally occurring dual inhibitor that inhibited both SERT and acetylcholinesterase (AChE) in vitro. The DKP increased extracellular levels of the cerebral monoamines serotonin, norepinephrine, and dopamine in the medial prefrontal cortex and acetylcholine in the ventral hippocampus of freely moving rats when administered orally. Moreover, cyclo(L-Phe-L-Phe) significantly shortened escape latency in the water maze test in depressed mice previously subjected to a repeated open-space swimming task, which induces a depression-like state. Cyclo(L-Phe-L-Phe) also significantly improved accuracy rates in a radial maze test in rats and increased step-through latencies in a passive avoidance test in mice with scopolamine-induced amnesia. These animal test results suggest that cyclo(L-Phe-L-Phe), which is present abundantly in some foods such as chicken essence, may abrogate the onset of depression and, thus, contribute to preventing the development of Alzheimer’s disease and other dementia, because senile depression is a risk factor for dementia.

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“…Drimentines have anthelmintic activity against various parasites [253][254][255]. DKPs demonstrate an antimalarial effect [256][257][258][259].…”

Section: Anthelmintic Activitymentioning

confidence: 99%

Cyclic Dipeptides: The Biological and Structural Landscape with Special Focus on the Anti-Cancer Proline-Based Scaffold

et al. 2021

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Cyclic dipeptides, also know as diketopiperazines (DKP), the simplest cyclic forms of peptides widespread in nature, are unsurpassed in their structural and bio-functional diversity. DKPs, especially those containing proline, due to their unique features such as, inter alia, extra-rigid conformation, high resistance to enzyme degradation, increased cell permeability, and expandable ability to bind a diverse of targets with better affinity, have emerged in the last years as biologically pre-validated platforms for the drug discovery. Recent advances have revealed their enormous potential in the development of next-generation theranostics, smart delivery systems, and biomaterials. Here, we present an updated review on the biological and structural profile of these appealing biomolecules, with a particular emphasis on those with anticancer properties, since cancers are the main cause of death all over the world. Additionally, we provide a consideration on supramolecular structuring and synthons, based on the proline-based DKP privileged scaffold, for inspiration in the design of compound libraries in search of ideal ligands, innovative self-assembled nanomaterials, and bio-functional architectures.

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Anthelmintic activity of 3,6-dibenzyl-2,5-dioxopiperazine, cyclo(L-Phe-L-Phe)

Cited by 15 publications

References 11 publications

Structural Diversity and Biological Activities of the Cyclodipeptides from Fungi

Structural Diversity and Biological Activities of the Cyclodipeptides from Fungi

A DKP Cyclo(L-Phe-L-Phe) Found in Chicken Essence Is a Dual Inhibitor of the Serotonin Transporter and Acetylcholinesterase

Cyclic Dipeptides: The Biological and Structural Landscape with Special Focus on the Anti-Cancer Proline-Based Scaffold

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