Antibacterial and NF-κB Inhibitory Lumazine Peptides, Aspochalasin, γ-Butyrolactone Derivatives, and Cyclic Peptides from a Hawaiian <i>Aspergillus flavipes</i>

Wu, Xiaohua; Bai, Helong; Zaman, KH Ahammad Uz; Hou, Shaobin; Saito, Jennifer A.; Wongwiwatthananukit, Supakit; Kim, Kyung Sik; Cao, Shugeng

doi:10.1021/acs.jnatprod.0c00344

Cited by 18 publications

(10 citation statements)

References 46 publications

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“…Chemical investigation of the EtOAc extract of an endophytic fungus Aspergillus flavipes DZ-3 led to the isolation of two new alkaloids, named asperflaloids A and B (1-2), and 10 known compounds (3)(4)(5)(6)(7)(8)(9)(10)(11)(12). The structures were established by extensive analyses of spectroscopic data (1D and 2D NMR, HRESIMS) and quantum chemistry calculation.…”

Section: Discussionmentioning

confidence: 99%

“…Species in Aspergillus have been proved to be prolific and are considered as an important source of chemical leads with hopeful biological activities [3,4]. Among the Aspergillus species, Aspergillus flavipes was an outstanding member; recent chemical research of the species resulted in the production of plenty of molecules with new structures and obvious biological activities, such as structurally complex merocytochalasans [5][6][7], lumazine peptides possessing significant antibacterial and NF-κB inhibitory activities [8], unusual chlorinated PKS-NRPS hybrid metabolites bearing potent pancreatic lipase inhibitory activity [9], and rare prenylated phenylbutyrolactones [10].…”

Section: Introductionmentioning

confidence: 99%

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Asperflaloids A and B from Aspergillus flavipes DZ-3, an Endophytic Fungus of Eucommia ulmoides Oliver

et al. 2021

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The fungus strain DZ-3 was isolated from twigs of the well-known medicinal plant Eucommia ulmoides Oliver and identified as Aspergillus flavipes. Two new alkaloids, named asperflaloids A and B (1 and 2), together with 10 known compounds (3–12) were obtained from the EtOAc extract of the strain. Interestingly, the alkaloids 1–4 with different frameworks are characterized by the presence of the same anthranilic acid residue. The structures were established by detailed analyses of the spectroscopic data. The absolute configuration of asperflaloids A and B was resolved by quantum chemistry calculation. All compounds were screened for their inhibitions against α-glucosidase and the antioxidant capacities. The results were that compound 3 had an IC50 value of 750.8 μM toward α-glucosidase, and the phenol compounds 7 and 8 exhibited potent antioxidant capacities with IC50 values 14.4 and 27.1 μM respectively.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Asperflaloids A and B from Aspergillus flavipes DZ-3, an Endophytic Fungus of Eucommia ulmoides Oliver

et al. 2021

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“…Cell viability assay of small-scale extracts to prioritize strains for large-scale fermentation The small-scale extracts prepared from isolated fungal strains were tested for the lack of toxicity against one or other of three human cell lines: HT1080 (fibrosarcoma cell line), T46D (breast cancer cell line) and A2780S (ovarian cancer cell line). Nontoxic extracts produced by the respective fungal strains were prioritized for large-scale fermentation (Wang et al, 2020a;Qader et al, 2021;Zaman et al, 2021).…”

Section: Fermentation and Extractionmentioning

confidence: 99%

A validated high-throughput method for assaying rat lungworm (Angiostrongylus cantonensis) motility when challenged with potentially anthelmintic natural products from Hawaiian fungi

et al. 2022

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Parasitic nematodes devastate human and animal health. The limited number of anthelmintics available is concerning, especially because of increasing drug resistance. Anthelmintics are commonly derived from natural products, e.g. fungi and plants. This investigation aimed to develop a high-throughput whole organism screening method based on a motility assay using the wMicroTracker system. Anthelmintic activity of extracts from Hawaiian fungi was screened against third-stage larvae of the parasitic nematode Angiostrongylus cantonensis, categorized according to the degree of motility reduction. Of the 108 crude samples and fractionated products, 48 showed some level of activity, with 13 reducing motility to 0–25% of the maximum exhibited, including two pure compounds, emethacin B and epicoccin E, neither previously known to exhibit anthelmintic properties. The process of bioassay-guided fractionation is illustrated in detail based on analysis of one of the crude extracts, which led to isolation of lamellicolic anhydride, a compound with moderate activity. This study validates the wMicroTracker system as an economical and high-throughput option for testing large suites of natural products against A. cantonensis, adds to the short list of diverse parasites for which it has been validated and highlights the value of A. cantonensis and Hawaiian fungi for discovery of new anthelmintics.

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“…These diverse climatic, ecological and geographical features have made Hawai’i a home for organisms with a vast diversity. Our studies over the past few years disclosed that fungi isolated from different Hawaiian sources such as soil, plants and the marine environment showed a great chemical and biological diversity [ 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 ].…”

Section: Introductionmentioning

confidence: 99%

Aspochalasin H1: A New Cyclic Aspochalasin from Hawaiian Plant-Associated Endophytic Fungus Aspergillus sp. FT1307

Qader

Zaman

et al. 2021

Molecules

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Aspergillus is one of the most diverse genera, and it is chemically profound and known to produce many biologically active secondary metabolites. In the present study, a new aspochalasin H1 (1), together with nine known compounds (2–10), were isolated from a Hawaiian plant-associated endophytic fungus Aspergillus sp. FT1307. The structures were elucidated using nuclear magnetic resonance (NMR) (1H, 1H-1H COSY, HSQC, HMBC, ROESY and 1D NOE), high-resolution electrospray ionization mass spectroscopy (HRESIMS), and comparisons with the reported literature. The absolute configuration of the new compound was established by electronic circular dichroism (ECD) in combination with NMR calculations. The new compound contains an epoxide moiety and an adjacent trans-diol, which has not been reported before in the aspochalasin family. The antibacterial screening of the isolated compounds was carried out against pathogenic bacteria (Staphylococcus aureus, Methicillin-resistant S. aureus and Bacillus subtilis). The antiproliferative activity of compounds 1–10 was evaluated against human breast cancer cell lines (MCF-7 and T46D) and ovarian cancer cell lines (A2780).

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Antibacterial and NF-κB Inhibitory Lumazine Peptides, Aspochalasin, γ-Butyrolactone Derivatives, and Cyclic Peptides from a Hawaiian Aspergillus flavipes

Cited by 18 publications

References 46 publications

Asperflaloids A and B from Aspergillus flavipes DZ-3, an Endophytic Fungus of Eucommia ulmoides Oliver

Asperflaloids A and B from Aspergillus flavipes DZ-3, an Endophytic Fungus of Eucommia ulmoides Oliver

A validated high-throughput method for assaying rat lungworm (Angiostrongylus cantonensis) motility when challenged with potentially anthelmintic natural products from Hawaiian fungi

Aspochalasin H1: A New Cyclic Aspochalasin from Hawaiian Plant-Associated Endophytic Fungus Aspergillus sp. FT1307

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