Tasiamide F, a potent inhibitor of cathepsins D and E from a marine cyanobacterium

Al-Awadhi, Fatma H.; Ratnayake, Ranjala; Paul, Valerie J.; Luesch, Hendrik

doi:10.1016/j.bmc.2016.04.062

Cited by 30 publications

(32 citation statements)

References 27 publications

(41 reference statements)

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“…Tesiamide F ( 36 ), an analog of tesiamide B, was isolated from cyanobacterial species Lyngbya , from Guam [ 51 ]. As compound tesiamide F was an analog of the previously isolated tesiamide B, the difference lies in the replacement of amino acid residues in tesiamide B to Ala → Gly, Leu → Ile, Val → Ile, with the presence of a statin unit Ahppa (Amino hydroxyphenyl pentanoic acid) differing it from other tesiamide structures.…”

Section: Chemical Diversity Of Secondary Metabolites From Cyanobacmentioning

confidence: 99%

Structural Diversity, Biological Properties and Applications of Natural Products from Cyanobacteria. A Review

et al. 2017

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Nowadays, various drugs on the market are becoming more and more resistant to numerous diseases, thus declining their efficacy for treatment purposes in human beings. Antibiotic resistance is one among the top listed threat around the world which eventually urged the discovery of new potent drugs followed by an increase in the number of deaths caused by cancer due to chemotherapy resistance as well. Accordingly, marine cyanobacteria, being the oldest prokaryotic microorganisms belonging to a monophyletic group, have proven themselves as being able to generate pharmaceutically important natural products. They have long been known to produce distinct and structurally complex secondary metabolites including peptides, polyketides, alkaloids, lipids, and terpenes with potent biological properties and applications. As such, this review will focus on recently published novel compounds isolated from marine cyanobacteria along with their potential bioactivities such as antibacterial, antifungal, anticancer, anti-tuberculosis, immunosuppressive and anti-inflammatory capacities. Moreover, various structural classes, as well as their technological uses will also be discussed.

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Section: Chemical Diversity Of Secondary Metabolites From Cyanobacmentioning

confidence: 99%

Structural Diversity, Biological Properties and Applications of Natural Products from Cyanobacteria. A Review

et al. 2017

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“…For instance, grassystatins-tasiamides constitute a depsipeptide group of related compounds isolated from Lyngbya and Symploca tropical species [350,351,352,353,354,355,356]. These metabolites have shown protease inhibitory activity against cathepsin D, cathepsin E, and the β-amyloid precursor protein-cleaving enzyme A (BACE1) for tasiamides B and F [350,351] (Table 11). In addition, these compounds have shown moderate or no cytotoxicity at concentrations higher than required for protease inhibitory activity [353,354,356].…”

Section: Beneficial Activities Of Natural Products Produced By Cyamentioning

confidence: 99%

Natural Products from Cyanobacteria: Focus on Beneficial Activities

et al. 2019

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Cyanobacteria are photosynthetic microorganisms that colonize diverse environments worldwide, ranging from ocean to freshwaters, soils, and extreme environments. Their adaptation capacities and the diversity of natural products that they synthesize, support cyanobacterial success in colonization of their respective ecological niches. Although cyanobacteria are well-known for their toxin production and their relative deleterious consequences, they also produce a large variety of molecules that exhibit beneficial properties with high potential in various fields (e.g., a synthetic analog of dolastatin 10 is used against Hodgkin’s lymphoma). The present review focuses on the beneficial activities of cyanobacterial molecules described so far. Based on an analysis of 670 papers, it appears that more than 90 genera of cyanobacteria have been observed to produce compounds with potentially beneficial activities in which most of them belong to the orders Oscillatoriales, Nostocales, Chroococcales, and Synechococcales. The rest of the cyanobacterial orders (i.e., Pleurocapsales, Chroococcidiopsales, and Gloeobacterales) remain poorly explored in terms of their molecular diversity and relative bioactivity. The diverse cyanobacterial metabolites possessing beneficial bioactivities belong to 10 different chemical classes (alkaloids, depsipeptides, lipopeptides, macrolides/lactones, peptides, terpenes, polysaccharides, lipids, polyketides, and others) that exhibit 14 major kinds of bioactivity. However, no direct relationship between the chemical class and the respective bioactivity of these molecules has been demonstrated. We further selected and specifically described 47 molecule families according to their respective bioactivities and their potential uses in pharmacology, cosmetology, agriculture, or other specific fields of interest. With this up-to-date review, we attempt to present new perspectives for the rational discovery of novel cyanobacterial metabolites with beneficial bioactivity.

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“…For instance, grassystatins-tasiamides constitutes a depsipeptide group of related compounds isolated from Lyngbya and Symploca tropical species [337][338][339][340][341][342][343]. These metabolites have shown protease inhibitory activity against cathepsin D, cathepsin E, and the β-amyloid precursor proteincleaving enzyme A (BACE1) for tasiamides B and F [337,338] (Table 11). In addition, these compounds have shown moderate or no cytotoxicity at concentrations higher than that of protease inhibitory activity [340,341,343].…”

Section: Other Metabolites With Potential Beneficial Propertiesmentioning

confidence: 99%

“…BACE1 is responsible for Aβ formation by cleaving the amyloid precursor protein (APP). As a result, BACE1 inhibitors could be promising targets for the development of new therapeutics against Alzheimer's disease [338,345]. Considering these activities, we assume that members of the grassystatins-tasiamides family constitute promising components for the development of antiproliferative agents, immune response modulatory compounds, and therapeutics for Alzheimer's disease treatment.…”

Section: Other Metabolites With Potential Beneficial Propertiesmentioning

confidence: 99%

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Natural Products from Cyanobacteria: Focus on Beneficial Activities

Demay

Bernard²,

Reinhardt

et al. 2019

Preprint

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Cyanobacteria are photosynthetic microorganisms that colonize diverse environments worldwide, ranging from ocean to freshwaters, soils, and extreme environments. Their adaptation capacities and the diversity of natural products (molecules, metabolites, or compounds) that they synthesize support the cyanobacterial success for the colonization of their respective ecological niches. Although cyanobacteria are well-known for their toxin production and their relative deleterious consequences, they also produce a large variety of molecules that exhibit beneficial properties with high potential for various fields of application (e.g., synthetic analog of the dolastatin 10 used against Hodgkin lymphoma). The present review specially focuses on the beneficial activities of cyanobacterial molecules described so far. Based on an analysis of 670 papers, it appears that more than 90 genera of cyanobacteria have been found to produce compounds with potential beneficial activities, most of them belonging to the orders Oscillatoriales, Nostocales Chroococcales, and Synechococcales. The rest of the cyanobacterial orders (i.e., Pleurocapsales, Chroococcidiopsales, and Gloeobacterales) remain poorly explored in terms of their molecular diversity and relative bioactivity. The diverse cyanobacterial molecules presenting beneficial bioactivities belong to 10 different chemical classes (alkaloids, depsipeptides, lipopeptides, macrolides/lactones, peptides, terpenes, polysaccharides, lipids, polyketides, and others) that exhibit 14 major kinds of bioactivity. However, no direct relation between the chemical class and the bioactivity of these molecules has been demonstrated. We further selected and specifically described 50 molecule families according to their specific bioactivities and their potential uses in pharmacology, cosmetology, agriculture, or other specific fields of interest. This up-to-date review takes advantage of the recent progresses in genome sequencing and biosynthetic pathway elucidation, and presents new perspectives for the rational discovery of new cyanobacterial metabolites with beneficial bioactivity.

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Tasiamide F, a potent inhibitor of cathepsins D and E from a marine cyanobacterium

Cited by 30 publications

References 27 publications

Structural Diversity, Biological Properties and Applications of Natural Products from Cyanobacteria. A Review

Structural Diversity, Biological Properties and Applications of Natural Products from Cyanobacteria. A Review

Natural Products from Cyanobacteria: Focus on Beneficial Activities

Natural Products from Cyanobacteria: Focus on Beneficial Activities

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