Diketopiperazines from the Marine Sponge Axinella sp.

Huang, Riming; Yan, Tao; Peng, Yan; Zhou, Xuefeng; Yang, Xian‐Wen; Liu, Yonghong

doi:10.1007/s10600-014-0911-2

Cited by 13 publications

(7 citation statements)

References 24 publications

(22 reference statements)

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“…The organic extracts of five marine-derived bacterial strains, specifically Bacillus endophyticus BI0327, Streptomyces albidoflavus BI0383, Nocardiopsis aegyptia BI0618, Streptomyces smyrnaeus BI0918, and Bacillus subtilis BI0980, isolated from marine sediments collected in the Aegean and Ionian seas, were subjected to repetitive chromatographic fractionations to yield three new natural products, namely cis-cyclo(Pro-3-chloro-Tyr) (15), trans-cyclo(Pro-3-chloro-Tyr) (16), and cis-cyclo(3-chloro-Tyr-Ile) (31), and 29 previously reported metabolites, which were identified as cyclo(Pro-Gly) (1) [24,25], cis-cyclo(Pro-Ala) (2) [26,27], cis-cyclo(Pro-Val) (3) [28][29][30], cis-cyclo(Pro-Leu) (4) [25,29,31,32], trans-cyclo(Pro-Leu) (5) [31,33], cis-cyclo(trans-4-Hyp-Leu) (6) [34], trans-cyclo(cis-4-Hyp-Leu) (7) [35], cis-cyclo(Pro-Ile) (8) [28,31,36], trans-cyclo(Pro-Ile) (9) [36,37], cis-cyclo(Pro-OMet) (10) [38], cis-cyclo(Pro-Phe) (11) [28,30,31,39,40], trans-cyclo(Pro-Phe) (12) [33,36,40], cis-cyclo(trans-4-Hyp-Phe) (13) [36,41], cis-cyclo(Pro-Tyr) (14) [42,43], cis-cyclo(Pro-Trp) (17) [44,45], cyclo(Leu-Gly) (18) [46]…”

Section: Resultsmentioning

confidence: 99%

New Chlorinated 2,5-Diketopiperazines from Marine-Derived Bacteria Isolated from Sediments of the Eastern Mediterranean Sea

et al. 2020

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From the organic extracts of five bacterial strains isolated from marine sediments collected in the East Mediterranean Sea, three new (15, 16, 31) and twenty-nine previously reported (1–14, 17–30, 32) metabolites bearing the 2,5-diketopiperazine skeleton were isolated. The structures of the chlorinated compounds 15, 16, and 31 were elucidated by extensive analysis of their spectroscopic data (NMR, MS, UV, IR). Compounds 15 and 16 were evaluated for their antifungal activity against Candida albicans and Aspergillus niger but were proven inactive. The relevant literature is supplemented with complete NMR assignments and revisions for the 29 previously reported compounds.

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Section: Resultsmentioning

confidence: 99%

New Chlorinated 2,5-Diketopiperazines from Marine-Derived Bacteria Isolated from Sediments of the Eastern Mediterranean Sea

et al. 2020

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“…Several types of cyclic dipeptides have been identified for their antimicrobial activities [ 31 , 32 , 33 , 34 ], indicating that they would be potential for antibiotic design. Some dipeptides were also reported to reduce virulence-factor production in bacterial pathogens [ 33 , 35 , 36 ].…”

Section: Discussionmentioning

confidence: 99%

Identification of Cyclic Dipeptides from Escherichia coli as New Antimicrobial Agents against Ralstonia Solanacearum

Song

Sun

et al. 2018

Molecules

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Ralstonia solanacearum is a causative agent of bacterial wilt in many important crops throughout the world. How to control bacterial wilt caused by R. solanacearum is a major problem in agriculture. In this study, we aim to isolate the biocontrol agents that have high efficacy in the control of bacterial wilt. Three new bacterial strains with high antimicrobial activity against R. solanacearum GMI1000 were isolated and identified. Our results demonstrated that these bacteria could remarkably inhibit the disease index of host plant infected by R. solanacearum. It was indicated that strain GZ-34 (CCTCC No. M 2016353) showed an excellent protective effect to tomato under greenhouse conditions. Strain GZ-34 was characterized as Escherichia coli based on morphology, biochemistry, and 16S rRNA analysis. We identified that the main antimicrobial compounds produced by E. coli GZ-34 were cyclo(l-Pro-d-Ile) and cyclo(l-Pro-l-Phe) using electrospray ionization mass spectrometry (ESI-MS) and nuclear magnetic resonance (NMR) analysis. The two active compounds also interfered with the expression levels of some pathogenicity-contributors of R. solanacearum. Furthermore, cyclo(l-Pro-l-Phe) effectively inhibited spore formation of Magnaporthe grisea, which is a vital pathogenesis process of the fungal pathogen, suggesting cyclic dipeptides from E. coli are promising potential antimicrobial agents with broad-spectrum activity to kill pathogens or interfere with their pathogenesis.

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“…Bioguided fractionation of the crude extract was then carried out by flash chromatography and preparative HPLC, and twelve DKPs were isolated: cyclo(dehydoalanine‐L‐leucine) ( 1 ) [26], cyclo(dehydroalanine‐L‐isoleucine) ( 2 ) [26], cyclo(L‐phenylalanine‐L‐alanine) ( 3 ) [27], cyclo(L‐leucine‐L‐glutaric acid) ( 4 ) [28], cyclo(L‐leucine‐L‐alanine) ( 5 ) [29], cyclo(L‐tyrosine‐L‐valine) ( 6 ) [30], cyclo(L‐tyrosine‐L‐tyrosine) ( 7 ) [31], cyclo(L‐tyrosine‐L‐leucine) ( 8 ) [32], cyclo(L‐proline‐L‐methionine) ( 9 ) [33], cyclo(L‐tyrosine‐L‐proline) ( 10 ) [33], cyclo(L‐proline‐L‐valine) ( 11 ) [34] and cyclo(L‐proline‐L‐isoleucine) ( 12 ) [35] (Fig. 2).…”

Section: Resultsmentioning

confidence: 99%

2,5‐diketopiperazines mitigate the amount of advanced glycation end products accumulated with age in human dermal fibroblasts

André

Touré²,

Stien

et al. 2020

Intern J of Cosmetic Sci

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OBJECTIVE: Glycation is a common non-enzymatic reaction between proteins and sugars, resulting in the formation of advanced glycation end products (AGEs) in the human body. As can be seen in diabetic patients, the accumulation of AGEs in the skin has aesthetic consequences (wrinkles, brown spots and yellowish complexion). Therefore, the objective of this work was to find compounds isolated from natural sources that could eliminate the final AGEs accumulated in the skin with ageing. METHODS AND RESULTS: A preliminary screening performed on a bank of microbial extracts and pure compounds showed that 2,5-Diketopiperazines (DKPs), as well as the extract of Sphingobacterium sp (SNB-CN13), reduced the presence of AGEs in fibroblasts by À28% and À23%, respectively. In this article, we present the dereplication approach used to reveal the presence of 26 different DKPs in the crude extract of Sphingobacterium sp. Bioguided fractionation has led to the isolation of 12 of them, whose identity has been confirmed by HRMS and NMR. A green synthesis approach has been developed to synthesize 3 symmetrical DKPs. The biological activity of all DKPs was evaluated by the development of an in vitro test using immunocytochemistry to reveal the presence of AGE carboxymethyl-lysine in human dermal fibroblasts. CONCLUSION: Our work shows for the first time that DKPs decrease the amount of carboxymethyl-lysine AGE in elderly human dermal fibroblasts grown in vitro. Therefore, diketopiperazines can be considered as compounds of interest for dermatological and cosmetic applications with an anti-ageing aim. R esum e OBJECTIF: La glycation est une r eaction non enzymatique courante entre les prot eines et les sucres, qui entraîne la formation de produits finaux de glycation avanc ee (AGE) dans le corps humain. Comme on peut le voir chez les patients diab etiques, l'accumulation d'AGE dans la peau a des cons equences esth etiques (rides, taches brunes, teint jaunâtre). Par cons equent, l'objectif de ce travail etait de trouver des compos es isol es de sources naturelles qui pourraient eliminer les AGE finaux accumul es dans la peau avec le vieillissement. M ETHODES & R ESULTATS: Un examen pr eliminaire effectu e sur une banque d'extraits microbiens et de compos es purs a montr e que les 2,5-dic etopip erazines (DKP), ainsi que l'extrait de Sphingobacterium sp. (SNB-CN13), r eduisaient la pr esence d'AGE dans les fibroblastes de-28% et-23% respectivement. Dans cet article, nous pr esentons l'approche de d er eplication utilis ee pour r ev eler la pr esence de 26 DKP diff erentes dans l'extrait brut de Sphingobacterium sp. Le fractionnement bioguid e a conduit a l'isolement de 12 d'entre elles, dont l'identit e a et e confirm ee par HRMS et RMN. Une approche de synth ese verte a et e d evelopp ee pour synth etiser 3 DKP sym etriques. L'activit e biologique de toutes les DKP a et e evalu ee par le d eveloppement d'un test in vitro utilisant l'immunocytochimie pour r ev eler la pr esence de carboxym ethyl-lysine AGE dans les fibroblastes dermiques...

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Diketopiperazines from the Marine Sponge Axinella sp.

Cited by 13 publications

References 24 publications

New Chlorinated 2,5-Diketopiperazines from Marine-Derived Bacteria Isolated from Sediments of the Eastern Mediterranean Sea

New Chlorinated 2,5-Diketopiperazines from Marine-Derived Bacteria Isolated from Sediments of the Eastern Mediterranean Sea

Identification of Cyclic Dipeptides from Escherichia coli as New Antimicrobial Agents against Ralstonia Solanacearum

2,5‐diketopiperazines mitigate the amount of advanced glycation end products accumulated with age in human dermal fibroblasts

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