Prenylated phenylbutyrolactones from cultures of a marine sponge-associated fungus Aspergillus flavipes KUFA1152

Machado, Fátima P.; Kumla, Decha; Pereira, José A.; Sousa, Emı́lia; Dethoup, Tida; Freitas-Silva, Joana; Costa, Paulo Martins da; Mistry, Sharad; Silva, Artur M. S.; Kijjoa, Anake

doi:10.1016/j.phytochem.2021.112709

Cited by 15 publications

(9 citation statements)

References 32 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%

“…The calculated ECD spectrum for (8 S)-1 showed a similar ECD curve with Cotton effects at 231 nm (−) and 290 (−) nm, allowing the assignment of the 8 S configuration for 1. The remaining compounds were identical to 2-(4-hydroxybenzyl)quinazolin-4(3H)one (3) [17], penipanoid A (4) [18], oxaline (5) [19], fuscoatramide (6) [20], 3,4-dihydroxybenzeneacetic acid (7) [21], 3,4-dihydroxyphenylacetic acid methyl ester (8) [21], phenylacetic acid (9) [22], 4-hydroxybenzeneacetamide (10) [23], 4-hydroxy phenylacetic acid methyl ester (11) [24], and 4-hydroxyphenylacetonitrile (12) [23] based on comparisons of their NMR data (Figures S13-S32) and specific rotations with those reported in the literature.…”

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%

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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“…Compound 4 was determined to be aspulvinone H by comparison its MS and NMR data with that of literature (Nagia et al, 2012). Compound 6 was identified as aspulvinone R, which was recently isolated from a marine sponge-associated fungus A. flavipes KUFA1152 as the first example of triprenylated aspulvinones (Machado et al, 2021). Compound 1 was obtained as yellow solid.…”

Section: Isolation and Structure Determination Of Aspulvinonesmentioning

confidence: 99%

“…Subsequent HPLC-guided chemical investigation of ASM-1 fermentation resulted in the isolation of six aspulvinone derivatives (1-6), including three new ones (1-3) (Figure 1). Aspulvinones and the analogs have been reported with various biological activities, such as inhibiting antibacterial (Machado et al, 2021), luciferase (Cruz et al, 2011), anti-influenza A viral (Gao et al, 2013), anticancer (Sun et al, 2019), anti-DPPH radicals (Zhang et al, 2015), as well as α-glucosidase inhibitory activity (Dewi et al, 2014;Wang et al, 2016;Zhang et al, 2016). However, there has been no systematic report on the mechanism for inhibition of α-glucosidase, structure-activity relationships, and hpyerglycemic effect in vivo by natural aspulvinones.…”

Section: Introductionmentioning

confidence: 99%

Aspulvinones Suppress Postprandial Hyperglycemia as Potent α-Glucosidase Inhibitors From Aspergillus terreus ASM-1

Cui

Sun

et al. 2021

Front. Chem.

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Chemical investigation of Aspergillus terreus ASM-1 fermentation resulted in the isolation of three new prenylated aspulvinones V–X (1–3), together with the previously reported analogs, aspulvinone H (4), J-CR (5), and R (6). Their structures were elucidated by various spectroscopic methods including HRESIMS and NMR, and the absolute configurations of 2 and 3 were determined by ECD comparison. Compounds 1–6 were evaluated for α-glucosidase inhibitory effects with acarbose as positive control. As a result, compounds 1 and 4 exhibited potent α-glucosidase inhibitory activities with IC50 values of 2.2 and 4.6 µM in mixed-type manners. The thermodynamic constants recognized the interaction between inhibitors and α-glucosidase was hydrophobic force-driven spontaneous exothermic reaction. The CD spectra also indicate that the compounds 1 and 4 changed the enzyme conformation. Furthermore, compound 4 significantly suppressed the increases in postprandial blood glucose levels in the C57BL/6J mice.

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γ‐Aromatic Butenolides of Microbial Source – A Review of Their Structures, Biological Activities and Biosynthesis

Fan

Wei

Si-Tu

et al. 2022

Chemistry & Biodiversity

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γ‐Aromatic butenolides (γ‐AB) are an important type of structures found in many bioactive microbial secondary metabolites (SMs). γ‐AB refer to a group of natural products (NPs) containing five‐membered (unsaturated) lactones with 3‐phenyl and 4‐benzyl substituents. Their wide‐range biological activities have inspired pharmaceutical chemists to explore its biosynthesis mechanisms and design strategies to construct the γ‐AB skeleton. Recently, there are a great deal of interesting research progress on the structures, biological activities and biosynthesis of γ‐AB. This review will focus on these aspects and summarize the important achievements of γ‐AB from 1975 to 2021.

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Prenylated phenylbutyrolactones from cultures of a marine sponge-associated fungus Aspergillus flavipes KUFA1152

Cited by 15 publications

References 32 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

Aspulvinones Suppress Postprandial Hyperglycemia as Potent α-Glucosidase Inhibitors From Aspergillus terreus ASM-1

γ‐Aromatic Butenolides of Microbial Source – A Review of Their Structures, Biological Activities and Biosynthesis

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