New butenolide derivatives from the marine sponge-derived fungus Aspergillus terreus

Sun, Yating; Liu, Jing‐Tang; Li, Lei; Gong, Chi Li; Wang, Shuping; Yang, Fan; Hua, Hui‐Ming; Lin, Hou-Wen

doi:10.1016/j.bmcl.2017.12.049

Cited by 51 publications

(41 citation statements)

References 25 publications

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“…(±)-Asperteretone B ( 2a/2b ) were also obtained as white, amorphous powders and assigned the molecular formula C 23 H 24 O 5 , as determined from the HRESIMS analysis at m/z 403.1526 [M + Na] + (calcd for C 23 H 24 O 5 Na, 403.1521) and 13 C NMR data. The 1D (Table 2 ) and 2D NMR spectra of 2 were completely identical to that of the reported (±)-asperteretal D (Sun Y. et al, 2018 ), which drove us to believe that they shared the same structures. The 1,3,4-trisubstituted phenyl group with a C-4” hydroxyl and a C-3” prenyl motif and para -disubstituted phenyl group with a C-4' hydroxyl motif were explicitly confirmed by detailed analysis of the 2D NMR data (Figure 2 ) of 2 .…”

Section: Resultssupporting

confidence: 75%

α-Glucosidase Inhibitors From the Coral-Associated Fungus Aspergillus terreus

Liu

Sun

et al. 2018

Front. Chem.

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Nine novel butenolide derivatives, including four pairs of enantiomers, named (±)-asperteretones A–D (1a/1b–4a/4b), and a racemate, named asperteretone E (5), were isolated and identified from the coral-associated fungus Aspergillus terreus. All the structures were established based on extensive spectroscopic analyses, including HRESIMS and NMR data. The chiral chromatography analyses allowed the separation of (±)-asperteretones A–D, whose absolute configurations were further confirmed by experimental and calculated electronic circular dichroism (ECD) analysis. Structurally, compounds 2–5 represented the first examples of prenylated γ-butenolides bearing 2-phenyl-3-benzyl-4H-furan-1-one motifs, and their crucial biogenetically related metabolite, compound 1, was uniquely defined by an unexpected cleavage of oxygen bridge between C-1 and C-4. Importantly, (±)-asperteretal D and (4S)-4-decarboxylflavipesolide C were revised to (±)-asperteretones B (2a/2b) and D (4), respectively. Additionally, compounds 1a/1b–4a/4b and 5 were evaluated for the α-glucosidase inhibitory activity, and all these compounds exhibited potent inhibitory potency against α-glucosidase, with IC50 values ranging from 15.7 ± 1.1 to 53.1 ± 1.4 μM, which was much lower than that of the positive control acarbose (IC50 = 154.7 ± 8.1 μM), endowing them as promising leading molecules for the discovery of new α-glucosidase inhibitors for type-2 diabetes mellitus treatment.

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Section: Resultssupporting

confidence: 75%

α-Glucosidase Inhibitors From the Coral-Associated Fungus Aspergillus terreus

Liu

Sun

et al. 2018

Front. Chem.

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“…The fungus Aspergillus terreus is widely present in both marine benthos and terrestrial creatures and was previously reported to be rich in a characteristic metabolites‐butenolide (18, 19). The butenolide was widely concerned with its wide range of biologic activities, such as anti‐inflammatory (17), antioxidant (20), and α‐glucosidase inhibitor activities (21). Herein, 11 butenolides from the marine sponge–derived fungus A. terreus were sifted for their TNF‐α and α‐glucosidase inhibitory activites in vitro .…”

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confidence: 99%

Butyrolactone‐I, an efficient α‐glucosidase inhibitor, improves type 2 diabetes with potent TNF‐α–lowering properties through modulating gut microbiota in db/db mice

Liu

Zhu

et al. 2019

The FASEB Journal

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The aim of this study was to evaluate the effects of butyrolactone‐I (A6) on type 2 diabetes (T2D) in db/db mice because A6 was found to inhibit α‐glucosidase activities and TNF‐α release, which were associated with improving T2D. Male db/db mice were divided into 6 groups and given an equivalent volume of olive oil, acarbose, or different doses of A6 for 4 wk (n = 8/group). In this study, 11 butenolide derivatives were screened for their α‐glucosidase and TNF‐α suppressive activity in vitro. A6, an efficient α‐glucosidase inhibitor, exerts hypoglycemic and multiple activities in reducing weight, improving glucose tolerance and insulin resistance, increasing short‐chain fatty acid (SCFA) levels, activating SCFA‐induced increases in glucagon‐like peptide 1 and peroxisome proliferator‐activated receptor‐γ expression, enhancing intestinal mucosal barrier function and mitigating endoxemia in db/db mice. These effects may result from mediation of gut microbiota by A6. Meanwhile, A6, with potent TNF‐α–lowering properties, was demonstrated to have multiple salutary effects with excellent structural stability and long‐term safety in vivo. A6, an effective α‐glucosidase inhibitor with high security and stability, exerted potent antidiabetic effects in vivo. Furthermore, the modulation of gut microbiota of A6 was demonstrated to be one of the mechanisms contributing to anti‐inflammation properties and improving endoxemia. Our work confirms that the compound A6 is a prospective drug candidate for T2D.—Wu, W., Liu, L., Zhu, H., Sun, Y., Wu, Y., Liao, H., Gui, Y., Li, L., Liu, L., Sun, F., Lin, H. Butyrolactone‐I, an efficient α‐glucosidase inhibitor, improves type 2 diabetes with potent TNF‐α–lowering properties through modulating gut microbiota in db/db mice. FASEB J. 33, 12616–12629 (2019). http://www.fasebj.org

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“…α-Glucosidase, a crucial enzyme that breaks down complex carbohydrates for absorption, plays a key role in the treatment of diabetes. α-Glucosidase inhibitors such as natural products acarbose and voglibose can reduce the impact of carbohydrates on blood glucose level and prevent the digestion of carbohydrates, indicating that natural compounds play an important role in a discovery of anti-diabetic drugs [6,7].…”

Section: Introductionmentioning

confidence: 99%

“…Mar. Drugs 2020, 18, x 2 of 9 acarbose and voglibose can reduce the impact of carbohydrates on blood glucose level and prevent the digestion of carbohydrates, indicating that natural compounds play an important role in a discovery of anti-diabetic drugs [6,7]. Mangrove-derived fungi can produce secondary metabolites with novel structures and biological activities [8].…”

Section: Introductionmentioning

confidence: 99%

Bioactive Secondary Metabolites from the Culture of the Mangrove-Derived Fungus Daldinia eschscholtzii HJ004

et al. 2019

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Two new polyketides, 8-O-methylnodulisporin F (1) and nodulisporin H (2), two new naphthoquinones, 5-hydroxy-2-methoxy-6,7-dimethyl-1,4-naphthoquinone (3) and 5-hydroxy-2-methoxynaphtho[9–c]furan-1,4-dione (4), and a new naphthofuran 1,3,8-trimethoxynaphtho[9–c]furan (5), along with five known compounds 4-O-methyl eleutherol (6), 2-acetyl-7-methoxybenzofuran (7), (-)-orthosporin (8), diaporthin (9), and 6-hydroxymellein (10), were obtained from the EtOAc extract of the mangrove-derived fungus Daldinia eschscholtzii HJ004. The structures of the isolated compounds were elucidated by extensive NMR and MS analyses, while the absolute configurations of the stereogenic carbons were established based on experimental and calculated electronic circular dichroism spectra. Compounds 4 and 7 displayed a potent inhibitory activity against α-glucosidase with the IC50 values of 5.7 and 1.1 μg/mL, respectively. Compounds 1 and 2 showed a moderate antibacterial activity against Staphylococcus aureus, methicillin-resistant S. aureus (MRSA) and Bacillus cereus, with minimum inhibitory concentration (MIC) values ranging from 6.25 to 12.5 μg/mL. Compound 3 exhibited antibacterial activity against B. cereus with the MIC value of 12.5 μg/mL.

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New butenolide derivatives from the marine sponge-derived fungus Aspergillus terreus

Cited by 51 publications

References 25 publications

α-Glucosidase Inhibitors From the Coral-Associated Fungus Aspergillus terreus

α-Glucosidase Inhibitors From the Coral-Associated Fungus Aspergillus terreus

Butyrolactone‐I, an efficient α‐glucosidase inhibitor, improves type 2 diabetes with potent TNF‐α–lowering properties through modulating gut microbiota in db/db mice

Bioactive Secondary Metabolites from the Culture of the Mangrove-Derived Fungus Daldinia eschscholtzii HJ004

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