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Heptelidic acid

AG-CN2-0118-C250 250 µg INQ
AG-CN2-0118-M001 1 mg INQ
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Additional Information

Product Data
Synonyms Koningic acid; Avocettin; FO-4443; BRN 5091359
Properties
Formula C15H20O5
MW 280.3
CAS 57710-57-3 (74310-84-2 deleted)
Source/Host Isolated from Trichoderma sp.
Purity ≥95% (HPLC)
Appearance White solid.
Solubility Soluble in DMSO, ethanol, methanol or water.
Origin Manufactured by BioLinks K.K. with courtesy strain from The Kitasato Institute.
InChi Key JESMSCGUTIEROV-RTWAVKEYSA-N
Product Type Chemical
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Keep cool and dry.
Use/Stability Stable for at least 3 years after receipt when stored at -20°C.
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Product Description

  • Antibiotic [1, 2].
  • Potent selective glyceraldehyde 3-phosphate dehydrogenase (GAPDH) inhibitor. Binds to the essential Cys149 residue in the catalytic site of GAPDH [3-7, 10, 11].
  • Anticancer compound [8]. Selectively kills high-glycolytic cancer cells through glucose-dependent active ATP deprivation [12].
  • Antimalarial [9].
  • Apoptosis inhibitor. DNA fragmentation and caspase-3 activation inhibitor [13,16].
  • Selective and competitive inhibitor of mammalian DNA polymerases beta, lambda and terminal deoxynucleotidyl transferase (TdT) in family X of pols [14].

Product References

  1. A new sesquiterpene antibiotic, heptelidic acid producing organisms, fermentation, isolation and characterization: Y. Itoh, et al.; J. Antibiot. (Tokyo) 33, 468 (1980)
  2. Structure of heptelidic acid, a new sesquiterpene antibiotic from fungi: Y. Itoh, et al.; J. Antibiot. (Tokyo) 33, 525 (1980)
  3. Specific inhibition of glyceraldehyde-3-phosphate dehydrogenase by koningic acid (heptelidic acid): A. Endo, et al.; J. Antibiot. (Tokyo) 38, 920 (1985)
  4. Inactivation of rabbit muscle glyceraldehyde-3-phosphate dehydrogenase by koningic acid: K. Sakai, et al.; Biochim. Biophys. Acta 952, 297 (1988)
  5. Identification of koningic acid (heptelidic acid)-modified site in rabbit muscle glyceraldehyde-3-phosphate dehydrogenase: K. Sakai, et al.; Biochim. Biophys. Acta 1077, 192 (1991)
  6. Koningic acid (heptelidic acid) inhibition of glyceraldehyde-3-phosphate dehydrogenases from various sources: M. Kato, et al.; Biochim. Biophys. Acta 1120, 113 (1992)
  7. Glyceraldehyde-3-phosphate dehydrogenase is required for the transport of nitric oxide in platelets: B. McDonald, et al.; PNAS 90, 11122 (1993)
  8. Antitumor activity of heptelidic acid chlorohydrin: J. Kawashima, et al.; J. Antibiot. (Tokyo) 47, 1562 (1994)
  9. Antimalarial activity of radicicol, heptelidic acid and other fungal metabolites: Y. Tanaka, et al.; J. Antibiot. (Tokyo) 51, 153 (1998)
  10. Glyceraldehyde-3-phosphate dehydrogenase activity as an independent modifier of methylglyoxal levels in diabetes: P.J. Beisswenger, et al.; Biochim. Biophys. Acta 1637, 98 (2003)
  11. D-Glyceraldehyde causes production of intracellular peroxide in pancreatic islets, oxidative stress, and defective beta cell function via non-mitochondrial pathways: H. Takahashi, et al.; J. Biol. Chem. 279, 37316 (2004)
  12. Glucose-dependent active ATP depletion by koningic acid kills high-glycolytic cells: S. Kumagai, et al.; BBRC 365, 362 (2008)
  13. Heptelidic acid, a sesquiterpene lactone, inhibits Etoposide-induced apoptosis in human leukemia U937 cells: J.H. Kim & C.H. Lee; J. Microbiol. Biotechnol. 19, 787 (2009)
  14. Novel terpenoids, trichoderonic acids A and B isolated from Trichoderma virens, are selective inhibitors of family X DNA polymerases: Y. Yamaguchi, et al.; Biosci. Biotechnol. Biochem. 74, 793 (2010)
  15. Rapid effector function of memory CD8+ T cells requires an immediate-early glycolytic switch: P. M. Gubser, et al.; Nat. Immunol. 14, 1064 (2013)
  16. The immune-metabolic basis of effector memory CD4+ T cell function under hypoxic conditions: S. Dimeloe, et al.; J. Immunol. 196, 106 (2016)
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