2022
DOI: 10.1002/anie.202203175
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Euglenatides, Potent Antiproliferative Cyclic Peptides Isolated from the Freshwater Photosynthetic Microalga Euglena gracilis

Abstract: By limiting the nitrogen source to glutamic acid, we isolated cyclic peptides from Euglena gracilis containing asparagine and non-proteinogenic amino acids. Structure elucidation was accomplished through spectroscopic methods, mass spectrometry and chemical degradation. The euglenatides potently inhibit pathogenic fungi and cancer cell lines e.g., euglenatide B exhibiting IC 50 values of 4.3 μM in Aspergillus fumigatus and 0.29 μM in MCF-7 breast cancer cells. In an unprecedented convergence of non-ribosomal p… Show more

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Cited by 18 publications
(8 citation statements)
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“…Under anaerobic conditions, E. gracilis cells accumulate wax-esters [ 42 ]. Modification of the growth medium by replacing yeast extract, tryptone, and peptone with a single amino acid (glutamic acid, glutamate, or asparagine) resulted in the production of euglenatides, a new class of cyclic peptides with a strong inhibitory effect on pathogen fungi as well as a breast cancer cell line [ 43 ]. Transcript analysis of cells during improved culture conditions, which result in the accumulation of a desired product, will help to understand the underlying mechanism enabling further modification of the culturing process.…”
Section: Discussionmentioning
confidence: 99%
“…Under anaerobic conditions, E. gracilis cells accumulate wax-esters [ 42 ]. Modification of the growth medium by replacing yeast extract, tryptone, and peptone with a single amino acid (glutamic acid, glutamate, or asparagine) resulted in the production of euglenatides, a new class of cyclic peptides with a strong inhibitory effect on pathogen fungi as well as a breast cancer cell line [ 43 ]. Transcript analysis of cells during improved culture conditions, which result in the accumulation of a desired product, will help to understand the underlying mechanism enabling further modification of the culturing process.…”
Section: Discussionmentioning
confidence: 99%
“…For example, the presence of the euglenatides in multiple species of Euglena suggested an important biological role for these molecules. [58] Understanding specialized metabolite production in Trichodesmium species has application to areas as diverse as biological oceanography, chemical ecology, and drug discovery.…”
Section: Discussionmentioning
confidence: 99%
“…The polyketide framework of nemamide A embedded with three conjugated E-olefins and three asymmetric centers among which two are hydroxylated and one is aminated whereas nemamide B possess an additional conjugated olefin. In 2022, a series of another hybrid natural products euglenatides A-E (3)(4)(5)(6)(7) were discovered by Ganesan and coworkers from biomass extract of E. gracilis, a freshwater unicellular microalga, bearing a gene cluster of NRPSs and PKSs. 4 The structures of these secondary metabolites were established similarly to nemamides where the polyketide frameworks were found to be resembled closely to nemamide A.…”
Section: Introductionmentioning
confidence: 99%
“…In 2022, a series of another hybrid natural products euglenatides A-E (3)(4)(5)(6)(7) were discovered by Ganesan and coworkers from biomass extract of E. gracilis, a freshwater unicellular microalga, bearing a gene cluster of NRPSs and PKSs. 4 The structures of these secondary metabolites were established similarly to nemamides where the polyketide frameworks were found to be resembled closely to nemamide A. The saturated chain of these members is two-carbon homologated compared to nemamide A and there is an additional hydroxylated center in the polyketide counterpart for euglenatides A-C (3)(4)(5).…”
Section: Introductionmentioning
confidence: 99%