Aspulvinone H
Aspulvinone H is an orally active inhibitor of AChE, pancreatic lipase, glutamic-oxaloacetic transaminase 1, and α-glucosidase, with IC50 values of 25.95 μM, 47.06 μM, 5.91/6.91 μM, and 4.6 μM, respectively. It has a Ka of 2.14 μM against GOT1 and a Ki of 6.58 μM against α-glucosidase. Aspulvinone H inhibits cancer cell proliferation, interferes with glutamine metabolism, elevates ROS levels, and induces cell apoptosis and S-phase arrest. Aspulvinone H exhibits antibacterial activity against Staphylococcus aureus. Aspulvinone H inhibits the growth of pancreatic ductal adenocarcinoma xenografts. Aspulvinone H reduces postprandial blood glucose in mice. Aspulvinone H can be used in research related to pancreatic ductal adenocarcinoma, diabetes, and Staphylococcus aureus infection.
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- CAS No.: 57744-69-1
- Formule: C27H28O5
- Masse moléculaire:432.51
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Stockage:
Please store the product under the recommended conditions in the Certificate of Analysis.
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Activité biologique
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Chemical Information
- Pureté et documentation
- Références
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Help & FAQs
Activité biologique
Description
In Vitro
Aspulvinone H (Compound 4) moderately inhibits acetylcholinesterase and pancreatic lipase in vitro, with IC50 values of 25.95 μM and 47.06 μM, respectively[1].
Aspulvinone H (Compound 6) inhibits the enzymatic activity of recombinant human GOT1 with IC50 values of 5.91 μM and 6.91 μM, respectively. It also binds directly to GOT1 with a Kd of 2.14 μM[2].
Aspulvinone H (0.1-100 μM; 48 h) selectively inhibits the proliferation of SW1990, PANC-1 and AsPC-1 pancreatic ductal adenocarcinoma cells (IC50 6.32-10.47 μM), while exhibits extremely low toxicity to non-malignant HPDE6C7 cells (IC50 >100 μM after 48 h treatment)[2].
Aspulvinone H (10-40 μM) disrupts glutamine metabolism, reduces the NADPH/NADP+ ratio in SW1990 pancreatic ductal adenocarcinoma cells, and increases their ROS levels[2].
Aspulvinone H (10-40 μM; 48 h) induces dose-dependent apoptosis and S-phase cell cycle arrest, inhibits cell proliferation, and suppresses migration in a dose- and time-dependent manner in SW1990 pancreatic ductal adenocarcinoma cells[2].
Aspulvinone H (Compound 4) (0.1 μM-10 mM; 10 min enzyme incubation, 15 min substrate incubation) potently inhibits α-glucosidase derived from Saccharomyces cerevisiae via a mixed-type inhibition mechanism, with an IC50 value of 4.6 μM, and exhibits higher affinity for the free enzyme than for the enzyme-substrate complex[3].
Aspulvinone H (40 μg/disc; 24 h) exhibits antibacterial activity against Staphylococcus aureus, producing an 11 mm inhibition zone after incubation at 38 °C for 24 h[4].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:Pancreatic ductal adenocarcinoma cell lines SW1990, PANC-1, AsPC-1; nonmalignant human pancreatic duct epithelial cell line HPDE6C7
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Concentration:0.1-100 μM
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Incubation Time:48 h
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Result:Inhibited growth of PDAC cell lines with IC50 values of 6.32 μM (SW1990), 10.47 μM (PANC-1), and a value between these for AsPC-1.
Exhibited minimal cytotoxicity to nonmalignant HPDE6C7 cells, with an IC50 value over 100 μM.
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Cell Line:SW1990 PDAC cells
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Concentration:10-40 μM
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Incubation Time:48 h
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Result:Induced apoptosis in a dose-dependent manner, with apoptosis rates of 9.5% (10 μM), 28.3% (20 μM), and 80.2% (40 μM).
Induced S-phase cell cycle arrest, increasing S-phase cell proportion to 32.5% (10 μM), 38.6% (20 μM), and 43.9% (40 μM), while decreasing G0/G1 phase proportion to 59.4% (10 μM), 48.6% (20 μM), and 43.5% (40 μM).
In Vivo
Aspulvinone H (25 mg/kg; oral gavage; single administration) reduces the postprandial blood glucose AUC0-t and inhibits blood glucose elevation in female C57BL/6J mice subjected to oral sucrose and maltose tolerance tests[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:CB-17/SCID (male, 8 weeks old, subcutaneous injection of 3×106 SW1990 cells)[2]
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Dosage:2.5 mg/kg; 5 mg/kg
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Administration:i.p.; daily; 14 days
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Result:Reduced tumor volumes significantly compared to control.
Decreased oxaloacetate (OAA) and malate levels in tumor tissue.
Increased aspartate (Asp) and glutamine (Gln) levels in tumor tissue.
Decreased NADPH/NADP+ ratio in tumor tissue.
Caused no significant changes in mouse body weight or histomorphology.
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Animal Model:C57BL/6J (female, 6 weeks old, 16-20 g)[3]
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Dosage:25 mg/kg
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Administration:i.g.; single dose
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Result:Significantly suppressed the rise in blood glucose levels at 30 and 60 minutes after sucrose loading compared to the negative control group.
Reduced the area under the blood glucose concentration-time curve (AUC) over 0-120 minutes by 13.2%.\nSignificantly reduced the postprandial blood glucose peak compared to the negative control group.
Reduced the AUC of postprandial blood glucose over 0-120 minutes by 19.7%.
Chemical Information
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CAS No. 57744-69-1
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Masse moléculaire 432.51
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Formule C27H28O5
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SMILES
OC1=C(C2=CC(C/C=C(C)\C)=C(C=C2)O)C(O/C1=C\C3=CC(C/C=C(C)\C)=C(C=C3)O)=O
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Structure Classification
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Initial Source
Aspergillus terreus ASM-1
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Livraison
Room temperature in continental US; may vary elsewhere.
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Stockage
Please store the product under the recommended conditions in the Certificate of Analysis.
Pureté et documentation
Références
[1]. Qi X, et al. A glyoxylate-containing benzene derivative and butenolides from a marine algicolous fungus Aspergillus sp. SCSIO 41304. Nat Prod Res. 2023;37(3):441-448. [Content Brief]
[2]. Yan S, et al. Discovery of GOT1 Inhibitors from a Marine-Derived Aspergillus terreus That Act against Pancreatic Ductal Adenocarcinoma. Mar Drugs. 2021 Oct 20;19(11):588. [Content Brief]
[3]. Wu C, et al. Aspulvinones Suppress Postprandial Hyperglycemia as Potent α-Glucosidase Inhibitors From Aspergillus terreus ASM-1. Front Chem. 2021 Aug 17;9:736070. [Content Brief]
[4]. Nagia MM, et al. Four butyrolactones and diverse bioactive secondary metabolites from terrestrial Aspergillus flavipes MM2: isolation and structure determination. Org Med Chem Lett. 2012;2(1):9. Published 2012 Mar 1. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Aspulvinone H Related Classifications
HY-N14093 Related Classifications
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