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MedKoo Cat#: 574184 | Name: Avenaciolide
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Description:

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

Avenaciolide is a water-insoluble fungal metabolite that inhibits glutamate transport in isolated rat liver mitochondria and Induces Apoptosis in Human Malignant Meningioma Cells through the Production of Reactive Oxygen Species.

Chemical Structure

Avenaciolide
Avenaciolide
CAS#26057-70-5

Theoretical Analysis

MedKoo Cat#: 574184

Name: Avenaciolide

CAS#: 26057-70-5

Chemical Formula: C15H22O4

Exact Mass: 266.1518

Molecular Weight: 266.34

Elemental Analysis: C, 67.65; H, 8.33; O, 24.03

Price and Availability

Size Price Availability Quantity
500µg USD 450.00 Back order
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Related CAS #
No Data
Synonym
(±)-Avenaciolide, Avenaciolide
IUPAC/Chemical Name
(3aR,4R,6aR)-rel-dihydro-3-methylene-4-octyl-furo[3,4-b]furan-2,6(3H,4H)-dione
InChi Key
GSTQYRQXFPSWSH-AVGNSLFASA-N
InChi Code
InChI=1S/C15H22O4/c1-3-4-5-6-7-8-9-11-12-10(2)14(16)19-13(12)15(17)18-11/h11-13H,2-9H2,1H3/t11-,12-,13-/m0/s1
SMILES Code
O=C(C1=C)O[C@@]2([H])[C@]1([H])[C@H](CCCCCCCC)OC2=O
Appearance
A residue
Purity
>95% (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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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

Preparing Stock Solutions

The following data is based on the product molecular weight 266.34 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
1: Katsuzawa T, Kujirai K, Kamisuki S, Shinoda Y. Avenaciolide Induces Apoptosis in Human Malignant Meningioma Cells through the Production of Reactive Oxygen Species. Biol Pharm Bull. 2022;45(4):517-521. doi: 10.1248/bpb.b21-01039. PMID: 35370277. 2: Godinot C. Avenaciolide inhibition of anion transport in mitochondria. FEBS Lett. 1974 Sep 15;46(1):138-40. doi: 10.1016/0014-5793(74)80353-4. PMID: 4370621. 3: Harris EJ, Wimhurst JM. Is avenaciolide another ionophore? Nat New Biol. 1973 Oct 31;245(148):271-3. doi: 10.1038/newbio245271a0. PMID: 4518992. 4: Wimhurst JM, Harris EJ. The actions of avenaciolide and ethanol on glucose metabolism and on related enzyme activities in the isolated perfused rat liver. Biochim Biophys Acta. 1976 Jun 23;437(1):51-61. doi: 10.1016/0304-4165(76)90346-9. PMID: 949510. 5: McGivan JD, Chappell JB. Avenaciolide: a specific inhibitor of glutamate transport in rat liver mitochondria. Biochem J. 1970 Feb;116(4):37P-38P. PMID: 5435480; PMCID: PMC1185479. 6: Harris EJ, Wimhurst JM. Ionophoric actions of avenaciolide on mitochondrial cations. Arch Biochem Biophys. 1974 Jun;162(2):426-35. doi: 10.1016/0003-9861(74)90201-x. PMID: 4276119. 7: Castelo-Branco PA, Rubinger MM, Guilardi S, Leite VM, dos Santos AR, de C Alves L, Lariucci C, Vencato I, Piló-Veloso D, Zambolim L. Synthesis, characterization, absolute structural determination and antifungal activity of a new chlorinated aromatic avenaciolide analogue. Pest Manag Sci. 2009 Jan;65(1):34-40. doi: 10.1002/ps.1640. PMID: 18785221. 8: Clark TN, Bishop AI, McLaughlin M, Calhoun LA, Johnson JA, Gray CA. Isolation of (-)-avenaciolide as the antifungal and antimycobacterial constituent of a Seimatosporium sp. Endophyte from the medicinal plant Hypericum perforatum . Nat Prod Commun. 2014 Oct;9(10):1495-6. PMID: 25522544. 9: Castelo-Branco PA, Rubinger MM, Alves Lde C, de Barros PM, Pereira SG, de Melo VJ, Pilo-Veloso D, Zambolim L. Synthesis and antifungal activity of aromatic bis-gamma-lactones analogous to avenaciolide. Chem Biodivers. 2007 Dec;4(12):2745-54. doi: 10.1002/cbdv.200790223. PMID: 18081084. 10: Aldridge DC, Turner WB. Two new mould metabolites related to avenaciolide. J Chem Soc Perkin 1. 1971;13:2431-2. doi: 10.1039/j39710002431. PMID: 5166602. 11: Parker WL, Johnson F. The total synthesis of dl-avenaciolide. J Org Chem. 1973 Jul 13;38(14):2489-96. doi: 10.1021/jo00954a015. PMID: 4730671. 12: Kovacević Z. Possible mechanisms of the efflux of glutamate from kidney mitochondria generated by the activity of mitochondrial glutaminase. Biochim Biophys Acta. 1975 Sep 8;396(3):325-34. doi: 10.1016/0005-2728(75)90139-5. PMID: 1174515. 13: Chang CM, Chern J, Chen MY, Huang KF, Chen CH, Yang YL, Wu SH. Avenaciolides: potential MurA-targeted inhibitors against peptidoglycan biosynthesis in methicillin-resistant Staphylococcus aureus (MRSA). J Am Chem Soc. 2015 Jan 14;137(1):267-75. doi: 10.1021/ja510375f. Epub 2014 Dec 31. Erratum in: J Am Chem Soc. 2015 Mar 18;137(10):3717. PMID: 25521652. 14: Bryła J, Dzik JM. Glutamate metabolism in relation to glutamate transport in kidney cortex mitochondria of rabbit. Biochim Biophys Acta. 1978 Oct 11;504(1):15-25. doi: 10.1016/0005-2728(78)90003-8. PMID: 708719. 15: Kuo JF. Effects of Bacillus subtilis protease, type 8 (subtilopeptidase A) on isolated adipose cells. Fructose utilization and its inhibition by avenaciolide, piericidin A and puromycin. Biochim Biophys Acta. 1968 Sep 3;165(2):208-17. doi: 10.1016/0304-4165(68)90048-2. PMID: 4971641. 16: Kuo JF, Dill IK, Holmlund CE, Bohonos N. Effects of avenaciolide on lipolysis and on glucose, amino acid and palmitic acid metabolism in isolated adipose cells. Biochem Pharmacol. 1968 Mar;17(3):345-50. doi: 10.1016/0006-2952(68)90243-8. PMID: 4298503. 17: Yu CM, Youn J, Jung J. Asymmetric sequential allylic transfer reaction for the synthesis of 2-(1-stannylvinyl)-1,3-diols: concise synthesis of (-)-avenaciolide and (-)-isoavenaciolide. Angew Chem Int Ed Engl. 2006 Feb 27;45(10):1553-6. doi: 10.1002/anie.200503863. PMID: 16470753. 18: Herrmann JL, Berger MH, Schlessinger RH. Letter: An efficient total synthesis of dl-avenaciolide. J Am Chem Soc. 1973 Nov 14;95(23):7923. doi: 10.1021/ja00804a091. PMID: 4759040. 19: Yang SS, Wang GJ, Cheng KF, Chen CH, Ju YM, Tsau YJ, Lee TH. Bioactive γ-lactones from the fermented broth of Neosartorya sp. Planta Med. 2010 Oct;76(15):1701-5. doi: 10.1055/s-0030-1249907. Epub 2010 May 5. PMID: 20446242. 20: Dennis SC, Land JM, Clark JB. Glutamate metabolism and transport in rat brain mitochondria. Biochem J. 1976 May 15;156(2):323-31. doi: 10.1042/bj1560323. PMID: 942412; PMCID: PMC1163752.

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