Chemical diversity and biological function of indolediketopiperazines from marine-derived fungi

Cao, Jun; Wang, Bin‐Gui

doi:10.1007/s42995-019-00023-0

Cited by 17 publications

(15 citation statements)

References 70 publications

(57 reference statements)

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“…In conclusion, chemical investigation of the mangrove endophytic fungus Aspergillus sp. 16-5c led to isolation and identification of six new alkaloids, aspergiamides A-F (1-6), with ten known analogs (7)(8)(9)(10)(11)(12)(13)(14)(15)(16). The potential of DKPs alkaloids as antidiabetic agents was evaluated by α-glucosidase inhibition and PTP1B inhibition assay.…”

Section: Resultsmentioning

confidence: 99%

“…16-5c were investigated. Chemical investigation yielded six new diketopiperazine alkaloids, including five indole diketopiperazine alkaloids, aspergiamides A-E (1-5) and one 4-quinazolinone like diketopiperazine alkaloids aspergiamide F (6), together with ten known alkaloids (7)(8)(9)(10)(11)(12)(13)(14)(15)(16) from the culture extracts of the fungus 16-5c (Figure 1). These compounds were evaluated the antidiabetic potential by screening the enzyme inhibition of α-glucosidase and PTP1B.…”

Section: Introductionmentioning

confidence: 99%

“…Marine fungi are important sources of diketopiperazine alkaloids. According to statistics, between 2000 and 2019, as many as 155 indole diketopiperazine alkaloids were identified from marine fungi alone [ 14 ].…”

Section: Introductionmentioning

confidence: 99%

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Isolation, Structural Characterization and Antidiabetic Activity of New Diketopiperazine Alkaloids from Mangrove Endophytic Fungus Aspergillus sp. 16-5c

Huang

et al. 2021

Marine Drugs

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Six new DIKETOPIPERAZINE alkaloids aspergiamides A–F (1–6), together with ten known alkaloids (7–16), were isolated from the mangrove endophytic fungus Aspergillus sp. 16-5c. The structures of the new compounds were elucidated based on 1D/2D NMR spectroscopic and HR-ESIMS data analyses. The absolute configurations of aspergiamides A-F were established based on the experimental and calculated ECD data. All the compounds were evaluated for the antidiabetic activity against α-glucosidase and PTP1B enzyme. The bioassay results disclosed compounds 1 and 9 exhibited significant α-glucosidase inhibitory with IC50 values of 18.2 and 7.6 μM, respectively; compounds 3, 10, 11, and 15 exhibited moderate α-glucosidase inhibition with IC50 values ranging from 40.7 to 83.9 μM; while no compounds showed obvious PTP1B enzyme inhibition activity.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Isolation, Structural Characterization and Antidiabetic Activity of New Diketopiperazine Alkaloids from Mangrove Endophytic Fungus Aspergillus sp. 16-5c

Huang

et al. 2021

Marine Drugs

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“…Endophytic fungi of these marine macroorganisms algae, sponges, corals, and mangrove have been the subject of this review since they are promising sources of diverse endophytic fungi with an isolation rate of 17%, 12%, 10%, and 10%, respectively as illustrated in Figure 2 [ 67 ]. Overall, from Figure 3 we can assume that the alkaloids and terpenoid constitute the highest percentage of compounds in the bioactive constituents of marine endophytic fungi followed by macrocyclic lactones, steroids, phenyl propanoid, anthraquinones, azaphilones, phenyl ether derivatives, and peptide as well as in this order they are the most frequent fungi in the isolation procedure.…”

Section: Main Textmentioning

confidence: 99%

Marine endophytic fungal metabolites: A whole new world of pharmaceutical therapy exploration

El-Bondkly

2021

Heliyon

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The growing threat arises due to diseases such as cancer and the infections around the world leading to a critical requirement for novel and constructive compounds with unique ways of action capable of combating these deadly diseases. At present, it is evident that endophytic fungi constitute an enormous as well as comparatively untapped source of great biodiversity that can be considered as a wellspring of effective novel natural products for medical, agricultural and industrial use. Marine endophytic fungi have been found in every marine plants (algae, seagrass, driftwood, mangrove plants), marine vertebrates (mainly, fish) or marine invertebrates (mainly, sponge and coral) inter- and intra-cellular without causing any palpable symptoms of illness. Since evolution of microbes and eukaryotes to a higher level, coevolution has resulted in specific interaction mechanisms. Endophytic fungi are known to influence the life cycle and are necessary for the homeostasis of their eukaryotic hosts and the chemical signals of their host have been shown to activate gene expression in endophytes to induce expression of endophytic secondary metabolites. Marine endophytic fungi are receiving increasing attention by chemists because of their varied and structurally unmatched compounds that have strong biological roles in life as lead pharmaceutical compounds, including anticancer, antiviral, insulin mimetic, antineurodegenerative, antimicrobial, antioxidant and immuno-suppressant compounds. Moreover, fungal endophytes proved to have different biological activities for exploitation in the environmental and agricultural sustainability.

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“…Marine fungi have proven to be a large reservoir of structurally unique and biologically active compounds (Cao and Wang 2020;Liu et al 2019). So far, over 2000 new natural products have been discovered from marine fungi, such as nitrogen-containing metabolites, sulfur-bearing compounds, and halogenated structures, even some of them with clinically relevant pharmacological activities (Jia et al 2015;Meng et al 2013;Newman and Cragg 2016;Rateb and Ebel 2011;Wang et al 2018).…”

Section: Introductionmentioning

confidence: 99%

Three nitrogen-containing metabolites from an algicolous isolate of Trichoderma asperellum

Song

Miao

Yin

et al. 2020

Mar Life Sci Technol

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As one of the most productive species, Trichoderma asperellum, especially isolated from marine algae, has contributed a number of new terpenes and nitrogen-bearing compounds, encouraging our continuous efforts to further explore them. Consequently, three new nitrogen-containing secondary metabolites, including cyclo(L-5-MeO-Pro-L-5-MeO-Pro) (1), 5′-acetoxy-deoxycyclonerin B (2), and 5′-acetoxy-deoxycyclonerin D (3) were isolated from the marine alga-derived endophytic fungus Trichoderma asperellum A-YMD-9-2. Their structures and relative configurations were fully elucidated through spectroscopic techniques, mainly including 1D/2D NMR and MS. The absolute configurations of 1 and 2 were ascertained on the basis of X-ray diffraction (Cu Kα radiation) and ECD data, respectively. The isolation of these new nitrogen-bearing compounds adds to the structural diversity of marine algicolous Trichoderma spp., and they display potent inhibition against some marine phytoplankton species.

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Chemical diversity and biological function of indolediketopiperazines from marine-derived fungi

Cited by 17 publications

References 70 publications

Isolation, Structural Characterization and Antidiabetic Activity of New Diketopiperazine Alkaloids from Mangrove Endophytic Fungus Aspergillus sp. 16-5c

Isolation, Structural Characterization and Antidiabetic Activity of New Diketopiperazine Alkaloids from Mangrove Endophytic Fungus Aspergillus sp. 16-5c

Marine endophytic fungal metabolites: A whole new world of pharmaceutical therapy exploration

Three nitrogen-containing metabolites from an algicolous isolate of Trichoderma asperellum

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