A new asymmetric diketopiperazine dimer from the sponge‐associated fungus <i>Aspergillus versicolor</i> 16F‐11

Gu, Bin-Bin; Gui, Yu-Han; Liu, Li; Su, Zhi-You; Lin, Hou‐Wen; Li, Lei; Sun, Fan; Wang, Shuping; Yang, Fan; Lin, Hou-Wen

doi:10.1002/mrc.4780

Cited by 14 publications

(22 citation statements)

References 10 publications

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“…Weak in vitro cytotoxicity was recorded towards prostate cancer PC3 cells upon exposure to 2 – 5 at 30 μM [57]. Recently, the epimer asperflocin ( 6 ) (Figure 1) was obtained from an EtOAc extract of A. versicolor 16F-11 isolated from the marine sponge Phakellia fusca , collected from Yongxing Island in China [58]. Solely differing from 2 on the chirality of C11’, asperflocin ( 6 ) was possibly biosynthesized by fungus through the random selection of L- or D-tryptophan since different residues are embedded in the structure [58].…”

Section: Chemistry and Biological Properties Of Marine Diketopipermentioning

confidence: 99%

“…Recently, the epimer asperflocin ( 6 ) (Figure 1) was obtained from an EtOAc extract of A. versicolor 16F-11 isolated from the marine sponge Phakellia fusca , collected from Yongxing Island in China [58]. Solely differing from 2 on the chirality of C11’, asperflocin ( 6 ) was possibly biosynthesized by fungus through the random selection of L- or D-tryptophan since different residues are embedded in the structure [58]. Despite being assayed against a panel of four cancer cell lines, 6 only proved to exert cytotoxicity against human melanoma A375 cells [58].…”

Section: Chemistry and Biological Properties Of Marine Diketopipermentioning

confidence: 99%

“…Solely differing from 2 on the chirality of C11’, asperflocin ( 6 ) was possibly biosynthesized by fungus through the random selection of L- or D-tryptophan since different residues are embedded in the structure [58]. Despite being assayed against a panel of four cancer cell lines, 6 only proved to exert cytotoxicity against human melanoma A375 cells [58].…”

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%

Section: Chemistry and Biological Properties Of Marine Diketopipermentioning

confidence: 99%

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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“…Asperflocin ( 154 ), a novel asymmetric DKP dimer, was isolated from the fungus Aspergillus versicolor 16F-11, which was obtained from the sponge Phakellia fusca from Yongxing Island in the South China Sea. Compound 154 could inhibit the A375 (human melanoma) cell lines growth with the IC 50 value of 10.29 ± 2.37 μM [ 79 ].…”

Section: Chemical Structures Of Diketopiperazines From Marine Organismsmentioning

confidence: 99%

Structures and Biological Activities of Diketopiperazines from Marine Organisms: A Review

et al. 2021

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Diketopiperazines are potential structures with extensive biological functions, which have attracted much attention of natural product researchers for a long time. These compounds possess a stable six-membered ring, which is an important pharmacophore. The marine organisms have especially been proven to be a wide source for discovering diketopiperazine derivatives. In recent years, more and more interesting bioactive diketopiperazines had been found from various marine habitats. This review article is focused on the new 2,5-diketopiperazines derived from marine organisms (sponges and microorganisms) reported from the secondary half-year of 2014 to the first half of the year of 2021. We will comment their chemical structures, biological activities and sources. The objective is to assess the merit of these compounds for further study in the field of drug discovery.

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“…Aspergillus versicolor , a slow-growing filamentous fungus, normally are found in air, soil, marine sediment, corrupted plants, and agricultural products. Previous chemical investigations on the fungus Aspergillus versicolor from different environments have resulted in the identification of new secondary metabolites with a variety of structures, such as alkaloids [4,5,6,7,8,9], anthraquinones [10,11,12,13,14], xanthones [15,16,17,18,19], diphenyl ethers [20,21], lactones [22,23,24,25,26], peptides [27], polyketide [28], terpenoids [29,30], and varicuothiols [31].…”

Section: Introductionmentioning

confidence: 99%

New Diketopiperazines from a Marine-Derived Fungus Strain Aspergillus versicolor MF180151

Gao

et al. 2019

Marine Drugs

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Six new diketopiperazines, (±)-7,8-epoxy-brevianamide Q ((±)-1), (±)-8-hydroxy-brevianamide R ((±)-2), and (±)-8-epihydroxy-brevianamide R ((±)-3), together with four known compounds, (±)-brevianamide R ((±)-4), versicolorin B (5) and averufin (6), were isolated from a marine-derived fungus strain Aspergillus versicolor MF180151, which was recovered from a sediment sample collected from the Bohai Sea, China. The chemical structures were established by 1D- and 2D-NMR spectra and HR-ESI-MS. 1 is the first sample of brevianamides with an epoxy moiety. Their bioactivities were evaluated against Candida albicans, Bacillus subtilis, Staphylococcus aureus, methicillin-resistant S. aureus, Pseudomonas aeruginosa, and Bacillus Calmette-Guérin. Compounds 1–4 showed no activities against the pathogens, and compounds 5 and 6 showed moderate activities against S. aureus and methicillin-resistant S. aureus.

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A new asymmetric diketopiperazine dimer from the sponge‐associated fungus Aspergillus versicolor 16F‐11

Cited by 14 publications

References 10 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

Structures and Biological Activities of Diketopiperazines from Marine Organisms: A Review

New Diketopiperazines from a Marine-Derived Fungus Strain Aspergillus versicolor MF180151

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