Diketopiperazines and other bioactive compounds from bacterial symbionts of marine sponges

Santos, José Diogo Neves dos; Vitorino, Inês; Cruz, Mercedes de la; Díaz, Caridad; Cautain, Bastien; Annang, Frederick; Pérez-Moreno, Guiomar; González, Ignacio; Tormo, José R.; Martín, Jesús; Vicente, M. Francisca; Lage, Olga Maria

doi:10.1007/s10482-020-01398-2

Cited by 17 publications

(9 citation statements)

References 41 publications

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“…The synthesis of DKP stereoisomers, 1–12 , has also created an opportunity to systematically study their stereochemistry–activity relationship using in vitro assays, such as the biofilm assay. Although there have been reports of the biofilm modulation by DKPs, they either only identified the constituent amino acids present without attending to stereochemistry, or only looked at one stereoisomer without comparison to others [ 3 , 19 , 27 , 28 , 29 ]. The current study, on the other hand, is the first to screen all stereoisomers of cyclo(Phe-Pro), cyclo(Leu-Pro), and cyclo(Val-Pro), which revealed the most pronounced effects of cyclo(D-Phe-L-Pro) on both E. coli growth and biofilm formation.…”

Section: Discussionmentioning

confidence: 99%

Unambiguous Stereochemical Assignment of Cyclo(Phe-Pro), Cyclo(Leu-Pro), and Cyclo(Val-Pro) by Electronic Circular Dichroic Spectroscopy

et al. 2021

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2,5-diketopiperazines (DKPs) are cyclic dipeptides ubiquitously found in nature. In particular, cyclo(Phe-Pro), cyclo(Leu-Pro), and cyclo(Val-Pro) are frequently detected in many microbial cultures. Each of these DKPs has four possible stereoisomers due to the presence of two chirality centers. However, absolute configurations of natural DKPs are often ambiguous due to the lack of a simple, sensitive, and reproducible method for stereochemical assignment. This is an important problem because stereochemistry is a key determinant of biological activity. Here, we report a synthetic DKP library containing all stereoisomers of cyclo(Phe-Pro), cyclo(Leu-Pro), and cyclo(Val-Pro). The library was subjected to spectroscopic characterization using mass spectrometry, NMR, and electronic circular dichroism (ECD). It turned out that ECD can clearly differentiate DKP stereoisomers. Thus, our ECD dataset can serve as a reference for unambiguous stereochemical assignment of cyclo(Phe-Pro), cyclo(Leu-Pro), and cyclo(Val-Pro) samples from natural sources. The DKP library was also subjected to a biological screening using assays for E. coli growth and biofilm formation, which revealed distinct biological effects of cyclo(D-Phe-L-Pro).

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Section: Discussionmentioning

confidence: 99%

Unambiguous Stereochemical Assignment of Cyclo(Phe-Pro), Cyclo(Leu-Pro), and Cyclo(Val-Pro) by Electronic Circular Dichroic Spectroscopy

et al. 2021

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“…In fact, this is important not only to help reduce the number of strains to work with, but also to discriminate promising strains belonging to the same species, as even phylogenetically close strains can have different genomic content regarding the presence of biosynthetic gene clusters [ 131 ]. Moreover, this approach has proven to be successful in helping select good candidates which ultimately showed interesting bioactive profiles, including the potential production of novel molecules [ 131 , 132 , 133 ]. Furthermore, with the increase in available data on sequenced bacterial genomes, genome mining techniques have rapidly evolved for detecting secondary metabolite gene clusters [ 134 ].…”

Section: Screening Methodologies For the Detection Of Bioactive Mamentioning

confidence: 99%

From Ocean to Medicine: Pharmaceutical Applications of Metabolites from Marine Bacteria

et al. 2020

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Oceans cover seventy percent of the planet’s surface and besides being an immense reservoir of biological life, they serve as vital sources for human sustenance, tourism, transport and commerce. Yet, it is estimated by the National Oceanic and Atmospheric Administration (NOAA) that eighty percent of the oceans remain unexplored. The untapped biological resources present in oceans may be fundamental in solving several of the world’s public health crises of the 21st century, which span from the rise of antibiotic resistance in bacteria, pathogenic fungi and parasites, to the rise of cancer incidence and viral infection outbreaks. In this review, health risks as well as how marine bacterial derived natural products may be tools to fight them will be discussed. Moreover, an overview will be made of the research pipeline of novel molecules, from identification of bioactive bacterial crude extracts to the isolation and chemical characterization of the molecules within the framework of the One Health approach. This review highlights information that has been published since 2014, showing the current relevance of marine bacteria for the discovery of novel natural products.

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“…In addition to actinomycetes and their secondary metabolites, other bacteria and their products have demonstrated anti-hepatoma properties. For example, in 2019, Santos et al isolated and tested 12 Firmicutes and 44 Proteobacteria from Erylus spp. sponges obtained in Portuguese waters.…”

Section: Marine Bacteriamentioning

confidence: 99%

Marine Natural Products: A Potential Source of Anti-hepatocellular Carcinoma Drugs

et al. 2021

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Hepatocellular carcinoma (HCC) has high associated morbidity and mortality rates. Although chemical medication represents a primary HCC treatment strategy, low response rates and therapeutic resistance serve to reduce its efficacy. Hence, identifying novel effective drugs is urgently needed, and many researchers have sought to identify new anticancer drugs from marine organisms. The marine population is considered a "blue drug bank" of unique anti-cancer compounds with diverse groups of chemical structures. Here, we discuss marine-derived compounds, including PM060184 and bryostatin-1, with demonstrated anti-cancer activity in vitro or in vivo. Based on the marine source (sponges, algae, coral, bacteria, and fungi), we introduce pharmacological parameters, compound-induced cytotoxicity, effects on apoptosis and metastasis, and potential molecular mechanisms. Cumulatively, this review provides insights into anti-HCC research conducted to date in the field of marine natural products and marine-derived compounds, as well as the potential pharmacological mechanisms of these compounds and their status in drug development.

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Diketopiperazines and other bioactive compounds from bacterial symbionts of marine sponges

Cited by 17 publications

References 41 publications

Unambiguous Stereochemical Assignment of Cyclo(Phe-Pro), Cyclo(Leu-Pro), and Cyclo(Val-Pro) by Electronic Circular Dichroic Spectroscopy

Unambiguous Stereochemical Assignment of Cyclo(Phe-Pro), Cyclo(Leu-Pro), and Cyclo(Val-Pro) by Electronic Circular Dichroic Spectroscopy

From Ocean to Medicine: Pharmaceutical Applications of Metabolites from Marine Bacteria

Marine Natural Products: A Potential Source of Anti-hepatocellular Carcinoma Drugs

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