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Journal articles on the topic '5-diketopiperazine'

Author: Grafiati

Published: 9 March 2023

Last updated: 10 March 2023

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1

Xu, Mao, Xue, et al. "Structures and Absolute Configurations of Diketopiperazine Alkaloids Chrysopiperazines A–C from the Gorgonian-Derived Penicillium chrysogenum Fungus." Marine Drugs 17, no. 5 (2019): 250. http://dx.doi.org/10.3390/md17050250.

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Three new diketopiperazine alkaloids, including two oxepine‐containing diketopiperazines, chrysopiperazines A and B (1 and 2), and one quinazoline‐containing diketopiperazine, chrysopiperazine C (5), together with three known analogues (3, 4, and 6), were isolated from the gorgonian-derived Penicillium chrysogenum fungus. The relative and absolute configurations of C-3 and C-15 in 1 and 2, C-3 and C-14 in 5 were established by NOE modified Marfey’s analysis and electronic circular dichroism (ECD) calculations. Particularly, the absolute configurations of C-19 in 1 and 3, which was very challen

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2

Pétry, Nicolas, Hafid Benakki, Eric Clot, et al. "A mechanochemical approach to access the proline–proline diketopiperazine framework." Beilstein Journal of Organic Chemistry 13 (October 19, 2017): 2169–78. http://dx.doi.org/10.3762/bjoc.13.217.

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Ball milling was exploited to prepare a substituted proline building block by mechanochemical nucleophilic substitution. Subsequently, the mechanocoupling of hindered proline amino acid derivatives was developed to provide proline–proline dipeptides under solvent-free conditions. A deprotection–cyclization sequence yielded the corresponding diketopiperazines that were obtained with a high stereoselectivity which could be explained by DFT calculations. Using this method, an enantiopure disubstituted Pro–Pro diketopiperazine was synthesized in 4 steps, making 5 new bonds using a ball mill.

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3

Lee, Seoung Rak, Christine Beemelmanns, Leah M. M. Tsuma, Jon Clardy, Shugeng Cao, and Ki Hyun Kim. "A New Diketopiperazine, Cyclo(D-trans-Hyp-L-Leu) from a Kenyan Bacterium Bacillus licheniformis LB 8CT." Natural Product Communications 11, no. 4 (2016): 1934578X1601100. http://dx.doi.org/10.1177/1934578x1601100410.

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Bacterially-produced small molecules demonstrate a wide range of structural and functional diversity. A new diketopiperazine, cyclo(D- trans-Hyp-L-Leu) (1), and five other known diketopiperazines (2–6), were isolated and purified from the fermented broth of a Kenyan bacterium Bacillus licheniformis LB 8CT. The structure of 1 was elucidated by a combination of extensive spectroscopic analyses, including 2D NMR and HR-MS, and the absolute configuration was determined by a combination of NOESY analysis and Marfey's method. The known compounds were identified as cyclo(D- cis-Hyp-L-Leu) (2), cyclo(

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4

Mohsenian Kouchaksaraee, Reza, Mahdi Moridi Farimani, Fengjie Li, Melika Nazemi, and Deniz Tasdemir. "Integrating Molecular Networking and 1H NMR Spectroscopy for Isolation of Bioactive Metabolites from the Persian Gulf Sponge Axinella sinoxea." Marine Drugs 18, no. 7 (2020): 366. http://dx.doi.org/10.3390/md18070366.

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The geographic position, highly fluctuating sea temperatures and hypersalinity make Persian Gulf an extreme environment. Although this unique environment has high biodiversity dominated by invertebrates, its potential in marine biodiscovery has largely remained untapped. Herein, we aimed at a detailed analysis of the metabolome and bioactivity profiles of the marine sponge Axinella sinoxea collected from the northeast coast of the Persian Gulf in Iran. The crude extract and its Kupchan subextracts were tested in multiple in-house bioassays, and the crude extract and its CHCl3-soluble portion s

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5

Lamm, Assaf, Igal Gozlan, Adi Rotstein, and Dror Avisar. "Detection of amoxicillin-diketopiperazine-2′, 5′ in wastewater samples." Journal of Environmental Science and Health, Part A 44, no. 14 (2009): 1512–17. http://dx.doi.org/10.1080/10934520903263306.

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6

Zhang, Geng, Zhang, et al. "Discovery of Bioactive Indole-Diketopiperazines from the Marine-Derived Fungus Penicillium brasilianum Aided by Genomic Information." Marine Drugs 17, no. 9 (2019): 514. http://dx.doi.org/10.3390/md17090514.

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Identification and analysis of the whole genome of the marine-derived fungus Penicillium brasilianum HBU-136 revealed the presence of an interesting biosynthetic gene cluster (BGC) for non-ribosomal peptide synthetases (NRPS), highly homologous to the BGCs of indole-diketopiperazine derivatives. With the aid of genomic analysis, eight indole-diketopiperazines (1−8), including three new compounds, spirotryprostatin G (1), and cyclotryprostatins F and G (2 and 3), were obtained by large-scale cultivation of the fungal strain HBU-136 using rice medium with 1.0% MgCl2. The absolute configurations

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7

Suciati and Mary J. Garson. "Isolation of the Tetrapeptide Apicidins G, H and I from the Fungus Fusarium semitectum." Natural Product Communications 9, no. 2 (2014): 1934578X1400900. http://dx.doi.org/10.1177/1934578x1400900226.

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This study reports the isolation and characterization of three new tetrapeptides, apicidins G (1), H (2) and I (3), along with the known apicidin (4), apicidin A (5), apicidin C (6), diketopiperazine 7, equisetin (8) and 7-hydroxy-2-(2-hydroxypropyl)-5-methylchromone (9). The structures of the new compounds were deduced by 2D NMR spectroscopic and MS data.

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8

Fu, Peng, Peipei Liu, Haijun Qu та ін. "α-Pyrones and Diketopiperazine Derivatives from the Marine-Derived Actinomycete Nocardiopsis dassonvillei HR10-5". Journal of Natural Products 74, № 10 (2011): 2219–23. http://dx.doi.org/10.1021/np200597m.

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9

Marcuccio, SM, and JA Elix. "Pyrazine Chemistry. V. Synthesis of Methylanhydropicroroccellin and Dimethylpicroroccellin." Australian Journal of Chemistry 38, no. 12 (1985): 1785. http://dx.doi.org/10.1071/ch9851785.

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The structure of the lichen diketopiperazine, picroroccellin, has been studied by the synthesis of several of its degradation products. The three possible formulations of methylanhydropicroroccellin (3), (4) and (5) were synthesized and from the physical and chemical properties, the former two compounds were shown to be dissimilar from the naturally derived material. Furthermore, the reactivity of the 3- methoxypiperazine-2,5-dione (5) entirely paralleled that reported for picroroccellin and was consistent with the oxygen functions being located at the 3- and 6-positions of the piperazine-2,5-

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10

Song, Yin-Ping, Feng-Ping Miao, Sheng-Tao Fang, Xiu-Li Yin, and Nai-Yun Ji. "Halogenated and Nonhalogenated Metabolites from the Marine-Alga-Endophytic Fungus Trichoderma asperellum cf44-2." Marine Drugs 16, no. 8 (2018): 266. http://dx.doi.org/10.3390/md16080266.

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One new bisabolane sesquiterpene, bisabolan-1,10,11-triol (1), one new norbisabolane sesquiterpene, 12-nor-11-acetoxybisabolen-3,6,7-triol (2), two new naturally occurring monoterpenes, (7S)- and (7R)-1-hydroxy-3-p-menthen-9-oic acids (3 and 4), one new naturally occurring trichodenone, dechlorotrichodenone C (5), one new chlorine-containing trichodenone, 3-hydroxytrichodenone C (6), one new diketopiperazine, methylcordysinin A (7), and one new naturally occurring oxazole derivative, 4-oxazolepropanoic acid (8), were isolated from the culture of a marine brown alga-endophytic strain (cf44-2) o

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11

Radadia, Arpit C., Jaydip G. Rajapara, and Yogesh T. Naliapara. "An efficient protocol for the synthesis of N-fused 2, 5-diketopiperazine via base catalyzed Ugi-type MCR." Arkivoc 2018, no. 3 (2018): 174–83. http://dx.doi.org/10.24820/ark.5550190.p010.387.

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12

Chen, Xin, Xinyang Chen, Raphael R. Steimbach, et al. "Novel 2, 5-diketopiperazine derivatives as potent selective histone deacetylase 6 inhibitors: Rational design, synthesis and antiproliferative activity." European Journal of Medicinal Chemistry 187 (February 2020): 111950. http://dx.doi.org/10.1016/j.ejmech.2019.111950.

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13

Borthwick, Alan D., and John Liddle. "The design of orally bioavailable 2, 5-diketopiperazine oxytocin antagonists: from concept to clinical candidate for premature labor." Medicinal Research Reviews 31, no. 4 (2009): 576–604. http://dx.doi.org/10.1002/med.20193.

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14

Cai, Jian, Chunmei Chen, Yanhui Tan, et al. "Bioactive Polyketide and Diketopiperazine Derivatives from the Mangrove-Sediment-Derived Fungus Aspergillus sp. SCSIO41407." Molecules 26, no. 16 (2021): 4851. http://dx.doi.org/10.3390/molecules26164851.

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Ten polyketide derivatives (1–10), including a new natural product named (E)-2,4-dihydroxy-3-methyl-6-(2-oxopent-3-en-1-yl) benzaldehyde (1), and five known diketopiperazines (11–15), were isolated from the mangrove-sediment-derived fungus Aspergillus sp. SCSIO41407. The structures of 1–15 were determined via NMR and MS spectroscopic analysis. In a variety of bioactivity screening, 3 showed weak cytotoxicity against the A549 cell line, and 2 exhibited weak antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). Compounds 3, 5, and 6 showed inhibition against acetylch

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15

Acquah, Kojo Sekyi, Denzil R. Beukes, Digby F. Warner, et al. "Novel South African Rare Actinomycete Kribbella speibonae Strain SK5: A Prolific Producer of Hydroxamate Siderophores Including New Dehydroxylated Congeners." Molecules 25, no. 13 (2020): 2979. http://dx.doi.org/10.3390/molecules25132979.

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In this paper, we report on the chemistry of the rare South African Actinomycete Kribbella speibonae strain SK5, a prolific producer of hydroxamate siderophores and their congeners. Two new analogues, dehydroxylated desferrioxamines, speibonoxamine 1 and desoxy-desferrioxamine D1 2, have been isolated, together with four known hydroxamates, desferrioxamine D1 3, desferrioxamine B 4, desoxy-nocardamine 5 and nocardamine 6, and a diketopiperazine (DKP) 7. The structures of 1–7 were characterized by the analysis of HRESIMS and 1D and 2D NMR data, as well as by comparison with the relevant literat

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16

Yan, Li-Hong, Xiao-Ming Li, Lu-Ping Chi, Xin Li, and Bin-Gui Wang. "Six New Antimicrobial Metabolites from the Deep-Sea Sediment-Derived Fungus Aspergillus fumigatus SD-406." Marine Drugs 20, no. 1 (2021): 4. http://dx.doi.org/10.3390/md20010004.

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Six new metabolites, including a pair of inseparable mixtures of secofumitremorgins A (1a) and B (1b), which differed in the configuration of the nitrogen atom, 29-hydroxyfumiquinazoline C (6), 10R-15-methylpseurotin A (7), 1,4,23-trihydroxy-hopane-22,30-diol (10), and sphingofungin I (11), together with six known compounds (2–5 and 8–9), were isolated and identified from the deep-sea sediment-derived fungus Aspergillus fumigatus SD-406. Their structures were determined by detailed spectroscopic analysis of NMR and MS data, chiral HPLC analysis of the acidic hydrolysate, X-ray crystallographic

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17

Shaala, Lamiaa A., Diaa T. A. Youssef, Jihan M. Badr, Steve M. Harakeh, and Grégory Genta-Jouve. "Bioactive Diketopiperazines and Nucleoside Derivatives from a Sponge-Derived Streptomyces Species." Marine Drugs 17, no. 10 (2019): 584. http://dx.doi.org/10.3390/md17100584.

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Fractionation and purification of the ethyl acetate extract of the culture of a sponge-derived actinomycete, Streptomyces species Call-36, resulted in the isolation and identification of a new diketopiperazine, actinozine A (1), cyclo(2-OH-d-Pro-l-Leu) (2), two new nucleosides, thymidine-3-mercaptocarbamic acid (3) and thymidine-3-thioamine (4), together with cyclo(d-Pro-l-Phe) (5) and cyclo(l-Pro-l-Phe) (6). The structure assignments of the compounds were carried out by interpretation of 1D and 2D NMR data and mass spectral determinations. The absolute configurations of 1 and 2 were determine

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18

Lenstra, A. T. H., B. Bracke, B. van Dijk, S. Maes, C. Vanhulle, and H. O. Desseyn. "Net Intensities: Accuracy Improvement Through a Bayesian Perspective on the Measuring Strategy and Their Persistent Lack of Precision. An Illustration." Acta Crystallographica Section B Structural Science 54, no. 6 (1998): 851–58. http://dx.doi.org/10.1107/s0108768198004637.

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2,3-Diketopiperazine (2,3-piperazinedione), C4H6N2O2, crystallizes in the monoclinic space group P21/c with a = 5.941 (3), b = 10.080 (3), c = 8.282 (2) Å, β = 95.87 (3)°, V = 493.4 (5) Å3, Z = 4, Dx = 1.536 Mg m−3 and Mr = 114.1. The six-membered ring adopts a skew-boat conformation with Q = 0.467 (3) Å, θ = 64.6 (3)° and φ = 269.8 (4)°. The C 2 symmetry, which typifies the free molecule, is broken by the formation of two intermolecular N—H...O bonds involving only one of the C=O groups of the 2,3-diketopiperazine molecule. The intensity data typical for a time series are summarized in tradit

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19

Cai, Runlin, Hongming Jiang, Zeen Xiao, et al. "(−)- and (+)-Asperginulin A, a Pair of Indole Diketopiperazine Alkaloid Dimers with a 6/5/4/5/6 Pentacyclic Skeleton from the Mangrove Endophytic Fungus Aspergillus sp. SK-28." Organic Letters 21, no. 23 (2019): 9633–36. http://dx.doi.org/10.1021/acs.orglett.9b03796.

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20

Szultka-Młyńska, Małgorzata, Daria Janiszewska, and Bogusław Buszewski. "Molecularly Imprinted Polymers as Solid-Phase Microextraction Fibers for the Isolation of Selected Antibiotics from Human Plasma." Materials 14, no. 17 (2021): 4886. http://dx.doi.org/10.3390/ma14174886.

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The aim of this study was to examine the synthesis of novel molecularly imprinted polymer (MIP)-coated polythiophene and poly(3-methylthiophene) solid-phase microextraction fibers using the direct electropolymerization method. Synthesized SPME fibers were characterized with the use of various physicochemical instrumental techniques. MIP-SPME coatings were successfully applied to carry out the selective extraction of selected antibiotic drugs (amoxicillin, cefotaxime, metronidazole) and their metabolites (amoxycilloic acid, amoxicillin diketopiperazine, desacetyl cefotaxime, 3-desacetyl cefotax

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21

Yurchenko, Ekaterina, Ekaterina Menchinskaya, Evgeny Pislyagin, et al. "Neuroprotective Activity of Some Marine Fungal Metabolites in the 6-Hydroxydopamin- and Paraquat-Induced Parkinson’s Disease Models." Marine Drugs 16, no. 11 (2018): 457. http://dx.doi.org/10.3390/md16110457.

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A new melatonin analogue 6-hydroxy-N-acetyl-β-oxotryptamine (1) was isolated from the marine-derived fungus Penicillium sp. KMM 4672. It is the second case of melatonin-related compounds isolation from microfilamentous fungi. The neuroprotective activities of this metabolite, as well as 3-methylorsellinic acid (2) and 8-methoxy-3,5-dimethylisochroman-6-ol (3) from Penicillium sp. KMM 4672, candidusin A (4) and 4″-dehydroxycandidusin A (5) from Aspergillus sp. KMM 4676, and diketopiperazine mactanamide (6) from Aspergillus flocculosus, were investigated in the 6-hydroxydopamine (6-OHDA)- and pa

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22

Shaala, Lamiaa A., Diaa T. A. Youssef, Torki A. Alzughaibi, and Sameh S. Elhady. "Antimicrobial Chlorinated 3-Phenylpropanoic Acid Derivatives from the Red Sea Marine Actinomycete Streptomyces coelicolor LY001." Marine Drugs 18, no. 9 (2020): 450. http://dx.doi.org/10.3390/md18090450.

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The actinomycete strain Streptomyces coelicolor LY001 was purified from the sponge Callyspongia siphonella. Fractionation of the antimicrobial extract of the culture of the actinomycete afforded three new natural chlorinated derivatives of 3-phenylpropanoic acid, 3-(3,5-dichloro-4-hydroxyphenyl)propanoic acid (1), 3-(3,5-dichloro-4-hydroxyphenyl)propanoic acid methyl ester (2), and 3-(3-chloro-4-hydroxyphenyl)propanoic acid (3), together with 3-phenylpropanoic acid (4), E-cinnamic acid (5), and the diketopiperazine alkaloids cyclo(l-Phe-trans-4-OH-l-Pro) (6) and cyclo(l-Phe-cis-4-OH-d-Pro) (7)

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23

Salers, P., L. H. Ouafik, P. Giraud, J. Y. Maltese, A. Dutour, and C. Oliver. "Ontogeny of prolyl endopeptidase, pyroglutamyl peptidase I, TRH, and its metabolites in rat pancreas." American Journal of Physiology-Endocrinology and Metabolism 262, no. 6 (1992): E845—E850. http://dx.doi.org/10.1152/ajpendo.1992.262.6.e845.

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We demonstrate that two enzymes, soluble unspecific pyroglutamyl peptidase I and prolyl endopeptidase, able to degrade thyrotropin-releasing hormone (TRH) in vitro were present in pancreas at the early stage of rat development. Specific particulate pyroglutamyl peptidase II remained undetectable during ontogenesis. Pyroglutamyl peptidase I specific activity increased until day 3 and decreased after day 5. Furthermore, prolyl endopeptidase specific activity rose slightly to a peak on postnatal day 20. A good correlation between immunoreactive TRH and deaminated TRH (TRH-OH) was found in the 1st

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24

Miyamori, Chiaki, Taizo Kato, Eiichi Imura, et al. "Long-term effects of thyrotropin-releasing hormone and histidyl-proline diketopiperazine on the maturation of homeothermia and mitochondrial enzyme activities in neonatal rats." Acta Endocrinologica 119, no. 4 (1988): 575–81. http://dx.doi.org/10.1530/acta.0.1190575.

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Abstract. To elucidate the mechanism by which TRH and its metabolite, histidyl-proline diketopiperazine (cyclo(His-Pro)), act on the maturation of homoiothermy, the chronic effects of intrathecal administration of the peptides on body temperature, serum thyroid hormone levels, and mitochondrial energy-producing enzyme activities were examined in neonatal rats. The two peptides or an equimolar mixture of both were injected intrathecally at a dose of 3, 6 and 9 nmol for 7 consecutive days during the 1st, 2nd or 3rd week of life, respectively. Control rats were treated with saline and they were s

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25

van Vliet, Kimber, Elise S. Melis, Pim de Blaauw, et al. "Aspartame and Phe-Containing Degradation Products in Soft Drinks across Europe." Nutrients 12, no. 6 (2020): 1887. http://dx.doi.org/10.3390/nu12061887.

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Phenylketonuria and tyrosinemia type 1 are treated with dietary phenylalanine (Phe) restriction. Aspartame is a Phe-containing synthetic sweetener used in many products, including many ‘regular’ soft drinks. Its amount is (often) not declared; therefore, patients are advised not to consume aspartame-containing foods. This study aimed to determine the variation in aspartame concentrations and its Phe-containing degradation products in aspartame-containing soft drinks. For this, an LC–MS/MS method was developed for the analysis of aspartame, Phe, aspartylphenylalanine, and diketopiperazine in so

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26

Charlton, Peter A., Richard W. Faint, Fiona Bent, et al. "Evaluation of a Low Molecular Weight Modulator of Human Plasminogen Activator Inhibitor-1 Activity." Thrombosis and Haemostasis 75, no. 05 (1996): 808–15. http://dx.doi.org/10.1055/s-0038-1650371.

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SummaryA critical component in the regulation of thrombus formation and clearance is the balance between tissue plasminogen activator (tPA) and plasminogen activator inhibitor type-1 (PAM). An increase in the plasma concentration of PAH has been proposed as a risk factor in thrombotic disease. Inhibition of PAI-1 activity may have utility in the treatment of thromboembolic disease. We report here the evaluation of three diketopiperazine-based low molecular weight inhibitors of PAI-1 activity (XR334, XR1853 and XR5082). In vitro these compounds reversed the inhibitory effects of PAI-1 against b

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27

Prodolliet, Jacques, and Milene Bruelhart. "Determination of Aspartame and Its Major Decomposition Products in Foods." Journal of AOAC INTERNATIONAL 76, no. 2 (1993): 275–82. http://dx.doi.org/10.1093/jaoac/76.2.275.

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Abstract A liquid chromatographic procedure already evaluated in a preceding study for the analysis of acesulfam-K is also suitable for the determination of the intense sweetener aspartame in tabletop sweetener, candy, fruit beverage, fruit pulp, soft drink, yogurt, cream, cheese, and chocolate preparations. The method also allows the determination of aspartame’s major decomposition products: diketopiperazine, aspartylphenylalanine, and phenylalanine. Samples are extracted or diluted with water and filtered. Complex matrixes are centrifuged or clarified with Carrez solutions. An aliquot of the

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Hedley, Douglas, and Peter F. T. Vaughan. "Thyroliberin (TRH), 6-methyl-5-oxothiomorpholinyl-3-carbonyl histidylproline amide and histidylproline diketopiperazine do not affect the release of [3H]-acetyl choline and [3H]-choline from rat brain tissue cubes." Biochemical Pharmacology 34, no. 8 (1985): 1341–43. http://dx.doi.org/10.1016/0006-2952(85)90517-9.

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Ding, Yi, Xiaojing Zhu, Liling Hao, Mengyao Zhao, Qiang Hua, and Faliang An. "Bioactive Indolyl Diketopiperazines from the Marine Derived Endophytic Aspergillus versicolor DY180635." Marine Drugs 18, no. 7 (2020): 338. http://dx.doi.org/10.3390/md18070338.

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Four new indolyl diketopiperazines, aspamides A–E (1–4) and two new diketopiperazines, aspamides F–G (5–6), along with 11 known diketopiperazines and intermediates were isolated from the solid culture of Aspergillus versicolor, which is an endophyte with the sea crab (Chiromantes haematocheir). Further chiral high-performance liquid chromatography resolution gave enantiomers (+)- and (−)-4, respectively. The structures and absolute configurations of compounds 1–6 were determined by the comprehensive analyses of nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HR-MS), and el

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Harvey, S., and J. S. Baidwan. "Thyrotrophin-releasing hormone (TRH)-induced growth hormone secretion in fowl: binding of TRH to pituitary membranes." Journal of Molecular Endocrinology 3, no. 1 (1989): 23–32. http://dx.doi.org/10.1677/jme.0.0030023.

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ABSTRACT Heat-labile specific binding sites for [3H]3-methylhistidine2-TRH ([3H]Me-TRH) were demonstrated on chicken adenohypophysial membranes. These binding sites were of both high affinity (dissociation constant, Kd = 15·53 nm) and low capacity (maximum binding capacity, Bmax = 8·73 pmol/g tissue) and of low affinity (Kd = 104·5 nm) and high capacity (Bmax = 32·41 pmol/g). Binding of [3H]Me-TRH to the pituitary membranes was greater at 4 °C than at 39 °C and occurred with rate constants (k1) of 1·6× 106 and 3·39×106m-1 min-1 respectively. Dissociation of [3H]Me-TRH binding at 4 °C occurred

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Weckenmann, N. M., C. Maichle-Mössmer, and B. J. Nachtsheim. "Template-assisted photodimerization of N-unprotected uracil derivatives: selective formation of the cis–syn photodimer." Chemical Communications 53, no. 69 (2017): 9610–12. http://dx.doi.org/10.1039/c7cc05353c.

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Regulska, Katarzyna, Agnieszka Matera-Witkiewicz, Aleksandra Mikołajczyk, and Beata J. Stanisz. "The Degradation Product of Ramipril Is Potentially Carcinogenic, Genotoxic and Mutagenic." Applied Sciences 13, no. 4 (2023): 2358. http://dx.doi.org/10.3390/app13042358.

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(1) Background: The aim of this study was to identify the degradation product of ramipril (RAM) formed under dry air and to verify its potential modes of carcinogenicity. We intended to check whether its formation and presence in final dosage forms could pose a cancer risk to humans who are treated with RAM due to cardiological indications. The carcinogenicity of this compound was evaluated with respect to two mechanisms: a potential direct DNA-damage and indirect toxicity, secondary to forming mutagenic N-nitroso metabolites. (2) Methods: Firstly, a forced ageing test under dry air was conduc

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Rabal Biasetto, Carolina, Andressa Somensi, Fernanda Sales Figueiro, et al. "Diketopiperazines and arylethylamides produced by Schizophyllum commune, an endophytic fungus in Alchornea glandulosa." Eclética Química Journal 44, no. 3 (2019): 36–42. http://dx.doi.org/10.26850/1678-4618eqj.v44.3.2019.p36-42.

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Chemical investigation of the crude PDB extract obtained from the endophytic fungus Schizophyllum commune afforded the pure substances, cyclo(L-Pro-L-Val) (1), uracil (2), cyclo(Pro-Tyr) (3), p-hydroxybenzoic acid (4) and a mixture of Rel.cyclo(Pro-Phe) (5) and Rel.cyclo(Pro-Ile) (6). When cultured in corn, the extract of this fungus yielded N-(2-phenylethyl) acetamide (7) and N-(4-hydroxyphenylethyl) acetamide (8). The structures of all compounds were determined based on the analyses of their MS, 1D and 2D-NMR spectroscopic data. Analysis of the crude extracts obtained from small-scale cultur

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Shi, Ting, Li Zheng, Xiang-Qian Li, et al. "Nitrogenous Compounds from the Antarctic Fungus Pseudogymnoascus sp. HSX2#-11." Molecules 26, no. 9 (2021): 2636. http://dx.doi.org/10.3390/molecules26092636.

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The species Pseudogymnoascus is known as a psychrophilic pathogenic fungus which is ubiquitously distributed in Antarctica. While the studies of its secondary metabolites are infrequent. Systematic research of the metabolites of the Antarctic fungus Pseudogymnoascus sp. HSX2#-11 led to the isolation of one new pyridine derivative, 4-(2-methoxycarbonyl-ethyl)-pyridine-2-carboxylic acid methyl ester (1), together with one pyrimidine, thymine (2), and eight diketopiperazines, cyclo-(dehydroAla-l-Val) (3), cyclo-(dehydroAla-l-Ile) (4), cyclo-(dehydroAla-l-Leu) (5), cyclo-(dehydroAla-l-Phe) (6), cy

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35

Chen, M. Z., M. L. Dewis, K. Kraut, et al. "2, 5-Diketopiperazines (Cyclic Dipeptides) in Beef: Identification, Synthesis, and Sensory Evaluation." Journal of Food Science 74, no. 2 (2009): C100—C105. http://dx.doi.org/10.1111/j.1750-3841.2009.01062.x.

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36

Afiyatullov, Shamil Sh, Olesya I. Zhuravleva, Alexandr S. Antonov, et al. "New Metabolites from the Marine-Derived Fungus Aspergillus Fumigatus." Natural Product Communications 7, no. 4 (2012): 1934578X1200700. http://dx.doi.org/10.1177/1934578x1200700421.

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A new alkaloid, fumiquinazoline K (1), and a new nordammarane triterpenoid (2), together with three known diketopiperazines (3-5) and tryptoquivaline F (6) have been isolated from a marine strain of Aspergillus fumigatus KMM 4631 associated with the soft coral Sinularia sp. Their structures were determined by HR-MS and 1D and 2D NMR. Compounds 3-5 exhibit weak cytotoxicity against cytoplasm non-specific esterase in Ehrlich carcinoma cells. Compound 3 also induces early apoptosis of the same cells in a non-toxic range of concentrations.

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37

Haino, Takeharu, Hisashi Mitsuhashi, and Yoshimasa Fukazawa. "On-beads screening of solid-attached diketopiperazines for calix[5]arene-based receptor." Tetrahedron Letters 44, no. 20 (2003): 3889–92. http://dx.doi.org/10.1016/s0040-4039(03)00825-6.

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38

Iyer, Mani S., and Mark A. Lipton. "An improved synthesis of the diketopiperazine catalyst cyclo[(S)-HIS-(S)-PHE]." Bioorganic & Medicinal Chemistry Letters 3, no. 10 (1993): 2061–62. http://dx.doi.org/10.1016/s0960-894x(01)81015-5.

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39

Wang, Hongpeng, Frederike Drawert, Michael Steinert, Stefan Schulz та Hartmut Laatsch. "1-Acyl-3-O-[β-glucopyranosyl-(1″→6′)-β-glucopyranosyl]-glycerols and Cordycedipeptides B and C, New Metabolites from Bacillus pumilus". Natural Product Communications 11, № 9 (2016): 1934578X1601100. http://dx.doi.org/10.1177/1934578x1601100936.

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Four 1-monoacyl-3- O-[β-glucopyranosyl-(1→6)-β-glucopyranosyl]-glycerols (1) and four 1,2-diacyl-3- O-[β-glucopyranosyl-(1→6)-β-glucopyranosyl]-glycerols (2a) with acyl residues consisting of 1:1 mixtures of 1- iso-pentadecanoyl- and 1- anteiso-pentadecanoyl residues and the respective heptadecanoic acid isomers s as main components, have been characterized in the extracts of Bacillus pumilus strain DKS1. Twenty-seven further metabolites, among them the diketopiperazines cordycedipeptide A (3), B (4), and C (5), were obtained. All compounds were elucidated by NMR and MS techniques and fully ch

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40

Hirose, Yukiko, Norio Ogawa, and Akitane Mori. "Properties of histidyl-proline diketopiperazine [cyclo(His-Pro)] binding sites in rat liver." Regulatory Peptides 12, no. 4 (1985): 279–88. http://dx.doi.org/10.1016/0167-0115(85)90171-5.

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41

Hu, Jiansen, Zheng Li, Jieyu Gao, et al. "New Diketopiperazines from a Marine-Derived Fungus Strain Aspergillus versicolor MF180151." Marine Drugs 17, no. 5 (2019): 262. http://dx.doi.org/10.3390/md17050262.

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Six new diketopiperazines, (±)-7,8-epoxy-brevianamide Q ((±)-1), (±)-8-hydroxy-brevianamide R ((±)-2), and (±)-8-epihydroxy-brevianamide R ((±)-3), together with four known compounds, (±)-brevianamide R ((±)-4), versicolorin B (5) and averufin (6), were isolated from a marine-derived fungus strain Aspergillus versicolor MF180151, which was recovered from a sediment sample collected from the Bohai Sea, China. The chemical structures were established by 1D- and 2D-NMR spectra and HR-ESI-MS. 1 is the first sample of brevianamides with an epoxy moiety. Their bioactivities were evaluated against Ca

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42

Chi, Lu-Ping, Xiao-Ming Li, Li Li, Xin Li, and Bin-Gui Wang. "Cytotoxic Thiodiketopiperazine Derivatives from the Deep Sea-Derived Fungus Epicoccum nigrum SD-388." Marine Drugs 18, no. 3 (2020): 160. http://dx.doi.org/10.3390/md18030160.

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Four new thiodiketopiperazine alkaloids, namely, 5’-hydroxy-6’-ene-epicoccin G (1), 7-methoxy-7’-hydroxyepicoccin G (2), 8’-acetoxyepicoccin D (3), and 7’-demethoxyrostratin C (4), as well as a pair of new enantiomeric diketopiperazines, (±)-5-hydroxydiphenylalazine A (5), along with five known analogues (6–10), were isolated and identified from the culture extract of Epicoccum nigrum SD-388, a fungus obtained from deep-sea sediments (−4500 m). Their structures were established on the basis of detailed interpretation of the NMR spectroscopic and mass spectrometric data. X-ray crystallographic

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43

Kawamura, Shunsuke, Shinobu Sakurada, Tsukasa Sakurada, Kensuke Kisara, Yusuke Sasaki, and Kenji Suzuki. "The antinociceptive effects of histidyl-proline diketopiperazine and thyrotropin-releasing hormone in the mouse." European Journal of Pharmacology 112, no. 3 (1985): 287–94. http://dx.doi.org/10.1016/0014-2999(85)90774-5.

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44

Gao, Huquan, Tianjiao Zhu, Dehai Li, Qianqun Gu, and Weizhong Liu. "Prenylated indole diketopiperazine alkaloids from a mangrove rhizosphere soil derived fungus Aspergillus effuses H1-1." Archives of Pharmacal Research 36, no. 8 (2013): 952–56. http://dx.doi.org/10.1007/s12272-013-0107-5.

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45

Mieczkowski, Adam, Elżbieta Speina, Damian Trzybiński, et al. "Diketopiperazine-Based, Flexible Tadalafil Analogues: Synthesis, Crystal Structures and Biological Activity Profile." Molecules 26, no. 4 (2021): 794. http://dx.doi.org/10.3390/molecules26040794.

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Phosphodiesterase 5 (PDE5) is one of the most extensively studied phosphodiesterases that is highly specific for cyclic-GMP hydrolysis. PDE5 became a target for drug development based on its efficacy for treatment of erectile dysfunction. In the present study, we synthesized four novel analogues of the phosphodiesterase type 5 (PDE5) inhibitor—tadalafil, which differs in (i) ligand flexibility (rigid structure of tadalafil vs. conformational flexibility of newly synthesized compounds), (ii) stereochemistry associated with applied amino acid building blocks, and (iii) substitution with bromine

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46

Liu, Wen, Liping Wang, Bin Wang, et al. "Diketopiperazine and Diphenylether Derivatives from Marine Algae-Derived Aspergillus versicolor OUCMDZ-2738 by Epigenetic Activation." Marine Drugs 17, no. 1 (2018): 6. http://dx.doi.org/10.3390/md17010006.

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A chemical-epigenetic method was used to enhance the chemodiversity of a marine algicolous fungus. Apart from thirteen known compounds, (+)-brevianamide R ((+)-3), (‒)-brevianamide R ((‒)-3), (+)-brevianamide Q ((+)-4), (‒)-brevianamide Q ((‒)-4), brevianamide V ((+)-5), brevianamide W ((‒)-5), brevianamide K (6), diorcinol B (7), diorcinol C (8), diorcinol E (9), diorcinol J (10), diorcinol (11), 4-methoxycarbonyldiorcinol (12), two new compounds, (+)- and (‒)-brevianamide X ((+)- and (‒)- 2)), as well as a new naturally occurring one, 3-[6-(2-methylpropyl)-2-oxo-1H-pyrazin-3-yl]propanamide (

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47

Pons, Jean-François, Jean-Luc Fauchère, Frédéric Lamaty, Annie Molla, and René Lazaro. "A Constrained Diketopiperazine as a New Scaffold for the Synthesis of Peptidomimetics." European Journal of Organic Chemistry 1998, no. 5 (1998): 853–59. http://dx.doi.org/10.1002/(sici)1099-0690(199805)1998:5<853::aid-ejoc853>3.0.co;2-f.

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48

Murphy, K. P., and S. J. Gill. "Calorimetric measurement of the enthalpy of dissolution of diketopiperazine in water as a function of temperature." Thermochimica Acta 139 (March 1989): 279–90. http://dx.doi.org/10.1016/0040-6031(89)87028-5.

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49

Coursindel, Thibault, Audrey Restouin, Georges Dewynter, Jean Martinez, Yves Collette, and Isabelle Parrot. "Stereoselective ring contraction of 2,5-diketopiperazines: An innovative approach to the synthesis of promising bioactive 5-membered scaffolds." Bioorganic Chemistry 38, no. 5 (2010): 210–17. http://dx.doi.org/10.1016/j.bioorg.2010.05.002.

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50

Ho, Junming, Michelle L. Coote, and Christopher J. Easton. "The Distal Effect of N-Electron-withdrawing Groups on the Stability of Peptide Carbon Radicals." Australian Journal of Chemistry 64, no. 4 (2011): 403. http://dx.doi.org/10.1071/ch11003.

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The effect of electron-withdrawing substituents, hydrogen bonding and protonation at amide nitrogen on the stability of radicals formed by loss of either a distal C–H adjacent to the amide carbonyl or one proximal to the amide nitrogen for a series of acetamides and diketopiperazines has been studied via high-level ab initio methods. These studies show that the effect is to destabilize the radicals formed by abstraction of the proximal hydrogens, typically by 10–20 kJ mol–1, and stabilize the distal radicals typically by 5–10 kJ mol–1, but only if the distal radicals are polarized by another d

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