Tryptoquivalines W and X, two new compounds from a Hawaiian fungal strain and their biological activities

Zaman, KH Ahammad Uz; Hu, Zhenquan; Wu, Xiaohua; Cao, Shugeng

doi:10.1016/j.tetlet.2020.151730

Cited by 11 publications

(8 citation statements)

References 34 publications

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“…Interestingly, tryptoquivaline K (2) has a rare non-proteinogenic amino acid, 1-aminocyclopropane-1-carboxylic acid, uncommonly incorporated during the biosynthesis of the natural product [ 27 ]. A variety of biological results are reported in the literature for tryptoquivaline derivatives, including antifungal [ 28 ], antiviral [ 29 ] and NF-κB inhibitory activities [ 30 ].…”

Section: Resultsmentioning

confidence: 99%

Chemical Elicitors Induce Rare Bioactive Secondary Metabolites in Deep-Sea Bacteria under Laboratory Conditions

et al. 2021

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Bacterial genome sequencing has revealed a vast number of novel biosynthetic gene clusters (BGC) with potential to produce bioactive natural products. However, the biosynthesis of secondary metabolites by bacteria is often silenced under laboratory conditions, limiting the controlled expression of natural products. Here we describe an integrated methodology for the construction and screening of an elicited and pre-fractionated library of marine bacteria. In this pilot study, chemical elicitors were evaluated to mimic the natural environment and to induce the expression of cryptic BGCs in deep-sea bacteria. By integrating high-resolution untargeted metabolomics with cheminformatics analyses, it was possible to visualize, mine, identify and map the chemical and biological space of the elicited bacterial metabolites. The results show that elicited bacterial metabolites correspond to ~45% of the compounds produced under laboratory conditions. In addition, the elicited chemical space is novel (~70% of the elicited compounds) or concentrated in the chemical space of drugs. Fractionation of the crude extracts further evidenced minor compounds (~90% of the collection) and the detection of biological activity. This pilot work pinpoints strategies for constructing and evaluating chemically diverse bacterial natural product libraries towards the identification of novel bacterial metabolites in natural product-based drug discovery pipelines.

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Section: Resultsmentioning

confidence: 99%

Chemical Elicitors Induce Rare Bioactive Secondary Metabolites in Deep-Sea Bacteria under Laboratory Conditions

et al. 2021

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“…Tryptoquivalines are a type of indole alkaloids broadly dispersed in nature [ 12 ]. Interestingly, 24 Tryptoquivalines (A-V) have been isolated from two fungal genera.…”

Section: Secondary Metabolites Isolated From a Terreusmentioning

confidence: 99%

“…Interestingly, 24 Tryptoquivalines (A-V) have been isolated from two fungal genera. While Tryptoquivalines A-O, W and X were isolated from Aspergillus spp , Tryptoquivalines P–V were reported in Neosartorya species ( N. laciniosa, N. takakii, and N. pseudofischeri ) [ 12 ]. Tryptoquivalines A and B have been reported to display tremorgenic properties while Tryptoquivaline O exhibited antifungal activity [ 12 ].…”

Section: Secondary Metabolites Isolated From a Terreusmentioning

confidence: 99%

“…A. terreus is a significant saprophytic filamentous fungus that can be found in soils [ 11 ]. A. terreus is an ubiquitous fungal specie in tropical and subtropical regions, nonetheless, can additionally be found in brutal environmental conditions [ 12 ], such as extreme habitats with high salt, high alkalinity, high temperature, as well as drought, and other conditions [ 13 ]. Moreover, this endophytic fungus can be isolated from different hosts, including terrestrial plants, mangrove plants, soil samples, and marine organisms as demonstrated in Table 1 .…”

Section: Introductionmentioning

confidence: 99%

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Unearthing the fungal endophyte Aspergillus terreus for chemodiversity and medicinal prospects: a comprehensive review

Amr

Ibrahim

Elissawy

et al. 2023

Fungal Biol Biotechnol

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Aspergillus terreus microorganism represents a promising prospective source for drug discovery since it is rich in diverse kinds of bioactive secondary metabolites. It contributed to many biotechnological applications and its metabolites are used in the synthesis of certain pharmaceuticals and food products, in addition to its useful uses in fermentation processes. There are about 346 compounds identified from marine and terrestrial-derived A. terreus from 1987 until 2022, 172 compounds of them proved a vast array of bioactivity. This review aimed to create an up-to-date comprehensive literature data of A. terreus’s secondary metabolites classes supported by its different bioactivity data to be a scientific record for the next work in drug discovery.

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“…In the past few years, our research group has studied the secondary metabolites of some marine fungi including different Aspergillus species from Hawaii. These secondary metabolites had different types of structures and exhibited various biological activities ( Li et al, 2015 ; Fei-Zhang et al, 2016 ; Li et al, 2016 ; Huang et al, 2017 ; Li et al, 2018 ; Li et al, 2019 ; Wang et al, 2019 ; Zaman et al, 2020a ; Wang et al, 2020 ; Zaman et al, 2021 ). In our continuing search for bioactive molecules from Hawaiian fungi, we studied an extract of Aspergillus felis FM324, which led to the separation and identification of ten compounds (1–10).…”

Section: Introductionmentioning

confidence: 99%

New Alkaloids From a Hawaiian Fungal Strain Aspergillus felis FM324

et al. 2021

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Two new alkaloids tryptoquivaline Y (1) and pseurotin I (2), together with eight known compounds (3–10), were purified from a fungal strain Aspergillus felis FM324, which was isolated from a Hawaiian beach soil sample. The absolute configuration and physicochemical data of tryptoquivaline Z (3) were reported for the first time here in this paper. Compound 1 is an uncommon tryptoquivaline analog containing a 3-O-isobutanoyl group. The structures of the new compounds 1–2 and known compound 3 were elucidated through HRESIMS, NMR spectroscopy and ECD analysis. All the compounds were evaluated for their antiproliferative, antibacterial and NF-κB inhibitory activities. Compound 4 showed weak antibacterial activity against Staphylococcus aureus, methicillin resistant Staphylococcus aureus and Bacillus subtilis with the same MIC value of 59.2 µM. Compounds 3 and 2 inhibited NF-κB with IC50 values of 26.7 and 30.9 μM, respectively.

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Tryptoquivalines W and X, two new compounds from a Hawaiian fungal strain and their biological activities

Cited by 11 publications

References 34 publications

Chemical Elicitors Induce Rare Bioactive Secondary Metabolites in Deep-Sea Bacteria under Laboratory Conditions

Chemical Elicitors Induce Rare Bioactive Secondary Metabolites in Deep-Sea Bacteria under Laboratory Conditions

Unearthing the fungal endophyte Aspergillus terreus for chemodiversity and medicinal prospects: a comprehensive review

New Alkaloids From a Hawaiian Fungal Strain Aspergillus felis FM324

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