Aspulvinone H

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 208017

CAS#: 57744-69-1

Description: Aspulvinone H is a natural inhibitor of glutamic oxaloacetate transaminase 1 (GOT1), suppressing glutamine metabolism, making PDAC cells sensitive to oxidative stress and inhibiting cell proliferation, exhibiting potent in vivo antitumor activity in an SW1990-cell-induced xenograft model.

Chemical Structure

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Aspulvinone H
CAS# 57744-69-1
Instruction

Theoretical Analysis

MedKoo Cat#: 208017
Name: Aspulvinone H
CAS#: 57744-69-1
Chemical Formula: C27H28O5
Exact Mass: 432.19
Molecular Weight: 432.516
Elemental Analysis: C, 74.98; H, 6.53; O, 18.50

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Aspulvinone H; Aspulvinone-H; AspulvinoneH

IUPAC/Chemical Name: (Z)-4-hydroxy-5-(4-hydroxy-3-(3-methylbut-2-en-1-yl)benzylidene)-3-(4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl)furan-2(5H)-one

InChi Key: LFDYHAWYVIBCDT-OYKKKHCWSA-N

InChi Code: InChI=1S/C27H28O5/c1-16(2)5-8-19-13-18(7-11-22(19)28)14-24-26(30)25(27(31)32-24)21-10-12-23(29)20(15-21)9-6-17(3)4/h5-7,10-15,28-30H,8-9H2,1-4H3/b24-14-

SMILES Code: C/C(C)=C\CC1=CC(/C=C2OC(C(C3=CC(C/C=C(C)/C)=C(O)C=C3)=C\2O)=O)=CC=C1O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 432.52 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1.Liang XX, Zhang XJ, Zhao YX, Feng J, Zeng JC, Shi QQ, Kaunda JS, Li XL, Wang WG, Xiao WL. Aspulvins A-H, Aspulvinone Analogues with SARS-CoV-2 Mpro Inhibitory and Anti-inflammatory Activities from an Endophytic Cladosporium sp. J Nat Prod. 2022 Apr 22;85(4):878-887. doi: 10.1021/acs.jnatprod.1c01003. Epub 2022 Mar 16. PMID: 35293744; PMCID: PMC8938825.
2. Yan S, Qi C, Song W, Xu Q, Gu L, Sun W, Zhang Y. Discovery of GOT1 Inhibitors from a Marine-Derived Aspergillus terreus That Act against Pancreatic Ductal Adenocarcinoma. Mar Drugs. 2021 Oct 20;19(11):588. doi: 10.3390/md19110588. PMID: 34822459; PMCID: PMC8618880.
3. Qi X, Chen WH, Lin XP, Liao SR, Yang B, Zhou XF, Liu YH, Wang JF, Li Y. A glyoxylate-containing benzene derivative and butenolides from a marine algicolous fungus Aspergillus sp. SCSIO 41304. Nat Prod Res. 2021 Sep 20:1-8. doi: 10.1080/14786419.2021.1978994. Epub ahead of print. PMID: 34542359.
4. Wu C, Cui X, Sun L, Lu J, Li F, Song M, Zhang Y, Hao X, Tian C, Song M, Liu X. Aspulvinones Suppress Postprandial Hyperglycemia as Potent α-Glucosidase Inhibitors From Aspergillus terreus ASM-1. Front Chem. 2021 Aug 17;9:736070. doi: 10.3389/fchem.2021.736070. PMID: 34485249; PMCID: PMC8416056.
5. Machado FP, Kumla D, Pereira JA, Sousa E, Dethoup T, Freitas-Silva J, Costa PM, Mistry S, Silva AMS, Kijjoa A. Prenylated phenylbutyrolactones from cultures of a marine sponge-associated fungus Aspergillus flavipes KUFA1152. Phytochemistry. 2021 May;185:112709. doi: 10.1016/j.phytochem.2021.112709. Epub 2021 Feb 23. PMID: 33636575.
6. Wodajo A, Tskhovrebov AG, Le TA, Kubasov AS, Grishina MM, Krutius ON, Khrustalev VN. Crystal structure of 1,1'-{(1E,1'E)-[4,4'-(9H-fluorene-9,9-di-yl)bis-(4,1-phenyl-ene)]bis-(aza-nylyl-idene)bis(methanylyl-idene)}bis-(naphthalen-2-ol) di-chloro-benzene monosolvate. Acta Crystallogr E Crystallogr Commun. 2020 Sep 4;76(Pt 10):1579-1581. doi: 10.1107/S2056989020012104. PMID: 33117567; PMCID: PMC7534250.
7. Ezekiel CN, Kraak B, Sandoval-Denis M, Sulyok M, Oyedele OA, Ayeni KI, Makinde OM, Akinyemi OM, Krska R, Crous PW, Houbraken J. Diversity and toxigenicity of fungi and description of Fusarium madaense sp. nov. from cereals, legumes and soils in north-central Nigeria. MycoKeys. 2020 Jun 8;67:95-124. doi: 10.3897/mycokeys.67.52716. PMID: 32565683; PMCID: PMC7295817.
8. Manchoju A, Annadate RA, Desquien L, Pansare SV. Functionalization of diazotetronic acid and application in a stereoselective modular synthesis of pulvinone, aspulvinones A-E, G, Q and their analogues. Org Biomol Chem. 2018 Aug 29;16(34):6224-6238. doi: 10.1039/c8ob01511b. PMID: 30109333.
9. Nagia MM, El-Metwally MM, Shaaban M, El-Zalabani SM, Hanna AG. Four butyrolactones and diverse bioactive secondary metabolites from terrestrial Aspergillus flavipes MM2: isolation and structure determination. Org Med Chem Lett. 2012 Mar 1;2(1):9. doi: 10.1186/2191-2858-2-9. PMID: 22380482; PMCID: PMC3349564.
10. Takahashi I, Ojima N, Ogura K, Seto S. Purification and characterization of dimethylallyl pyrophosphate: aspulvinone dimethylallyltransferase from Aspergillus terreus. Biochemistry. 1978 Jun 27;17(13):2696-702. doi: 10.1021/bi00606a037. PMID: 678538.