Chetracins E and F, cytotoxic epipolythiodioxopiperazines from the marine-derived fungus <i>Acrostalagmus luteoalbus</i> HDN13-530

Yu, Ge; Wang, Yanjuan; Yu, Rilei; Feng, Yanyan; Wang, Lu; Che, Qian; Gu, Qianqun; Li, Dehai; Li, Jing; Zhu, Tianjiao

doi:10.1039/c7ra12063j

Cited by 20 publications

(33 citation statements)

References 14 publications

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“…First described from an Antarctic psychrophilic fungus along with the symmetric hexasulfide homolog chetracin C ( 23 ) (Figure 6) [126], 22 was later isolated from the algicolous fungus Westerdykella reniformis obtained from Prince Edward Island, Canada [125]. In 2018, Yu and colleagues [127] identified a marine strain of the fungus Acrostalagmus luteoalbus (HDN13-530) as a source of chetracins C ( 23 ), E ( 24 ) and F ( 25 ) (Figure 6).…”

Section: Chemistry and Biological Properties Of Marine Diketopipermentioning

confidence: 99%

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Double the Chemistry, Double the Fun: Structural Diversity and Biological Activity of Marine-Derived Diketopiperazine Dimers

et al. 2019

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While several marine natural products bearing the 2,5-diketopiperazine ring have been reported to date, the unique chemistry of dimeric frameworks appears to remain neglected. Frequently reported from marine-derived strains of fungi, many naturally occurring diketopiperazine dimers have been shown to display a wide spectrum of pharmacological properties, particularly within the field of cancer and antimicrobial therapy. While their structures illustrate the unmatched power of marine biosynthetic machinery, often exhibiting unsymmetrical connections with rare linkage frameworks, enhanced binding ability to a variety of pharmacologically relevant receptors has been also witnessed. The existence of a bifunctional linker to anchor two substrates, resulting in a higher concentration of pharmacophores in proximity to recognition sites of several receptors involved in human diseases, portrays this group of metabolites as privileged lead structures for advanced pre-clinical and clinical studies. Despite the structural novelty of various marine diketopiperazine dimers and their relevant bioactive properties in several models of disease, to our knowledge, this attractive subclass of compounds is reviewed here for the first time.

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Section: Chemistry and Biological Properties Of Marine Diketopipermentioning

confidence: 99%

“…Chetracins 22 – 25 were shown to be potent in vitro cytotoxic agents towards a series of cancer cell lines, in low µM or nM concentrations [126,127]. However, their pharmacological interest stems predominantly from their ability to act as HSP90 inhibitors [127,128].…”

Section: Chemistry and Biological Properties Of Marine Diketopipermentioning

confidence: 99%

Double the Chemistry, Double the Fun: Structural Diversity and Biological Activity of Marine-Derived Diketopiperazine Dimers

et al. 2019

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“…These compounds were evaluated for their cytotoxic activities against SF-268, MCF-7, NCI-H460, and HepG-2 cell lines, and compounds 1–5 showed significant cytotoxicity against all four cancer cell lines [44]. Two new epipolythiodioxopiperazines, named chetracins E and F (1 and 2), along with the previously known chetracin C, exhibited cytotoxicity against the five tested cancer cell lines at the low-micromolar or nanomolar IC50 values isolated from A. luteoalbus [45]. A novel alkali-tolerant rhamnosidase was isolated from the soil fungus A. luteoalbus from Argentina [46].…”

Section: Discussionmentioning

confidence: 99%

First Records of Rare Ascomycete Fungi,Acrostalagmus luteoalbus,Bartalinia robillardoides, andCollariella carterifrom Freshwater Samples in Korea

et al. 2019

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The distribution and occurrence of rare ascomycete fungi within freshwater samples in Korea was investigated. Three rare fungal strains, CNUFC-YR537-1, CNUFC-CNUP1-1, and CNUFC-NDR3-1, were isolated using serial dilution method. On the basis of their morphological characteristics and phylogenetic analysis of their internal transcribed spacer regions and 28S rDNA sequences, the three isolates were identified as Acrostalagmus luteoalbus , Bartalinia robillardoides , and Collariella carteri, respectively. To our knowledge, these are the first records of rare genera Acrostalagmus , Bartalinia , and Collariella from Korea, and the first reports of A. luteoalbus , B. robillardoides , and C. carteri from freshwater samples.

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“…Piperazine-derived alkaloids, especially diketopiperazines, are another common alkaloid class discovered from marine fungi. Two new cyctotoxic epipolythiodioxopiperazines alkaloids that possessed a bridged polysulfide piperazine ring, namely chetracins E ( 188 ) and F ( 189 ), were discovered from the marine-derived fungus Acrostalagmus luteoalbus HDN13-530 by Yu et al They exhibited remarkable cytotoxicity against a wide spectrum of cancer lines, with IC 50 values ranging from 0.2 to 3.6 μM [73]. Algae-derived fungi are also an excellent source of alkaloids.…”

Section: Alkaloidsmentioning

confidence: 99%

Bioactive Compounds Isolated from Marine-Derived Microbes in China: 2009–2018

Sun

et al. 2019

Marine Drugs

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This review outlines the research that was carried out regarding the isolation of bioactive compounds from marine-derived bacteria and fungi by China-based research groups from 2009–2018, with 897 publications being surveyed. Endophytic organisms featured heavily, with endophytes from mangroves, marine invertebrates, and marine algae making up more than 60% of the microbial strains investigated. There was also a strong focus on fungi as a source of active compounds, with 80% of publications focusing on this area. The rapid increase in the number of publications in the field is perhaps most notable, which have increased more than sevenfold over the past decade, and suggests that China-based researchers will play a major role in marine microbial natural products drug discovery in years to come.

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Chetracins E and F, cytotoxic epipolythiodioxopiperazines from the marine-derived fungus Acrostalagmus luteoalbus HDN13-530

Abstract: Three epipolythiodioxopiperazines with two new ones were isolated from a marine-derived fungus, and all of them exhibited extensive cytotoxicity.

Cited by 20 publications

References 14 publications

Double the Chemistry, Double the Fun: Structural Diversity and Biological Activity of Marine-Derived Diketopiperazine Dimers

Double the Chemistry, Double the Fun: Structural Diversity and Biological Activity of Marine-Derived Diketopiperazine Dimers

First Records of Rare Ascomycete Fungi,Acrostalagmus luteoalbus,Bartalinia robillardoides, andCollariella carterifrom Freshwater Samples in Korea

Bioactive Compounds Isolated from Marine-Derived Microbes in China: 2009–2018

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