Aristolochic acid

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Aristolochic acid I
Aristolochic acid molecule
IUPAC name

8-methoxy-6-nitrophenanthro[3,4-d][1,3]dioxole-5-carboxylic acid
Other names

Aristinic acid, Aristolochia yellow, Aristolochic acid A, Aristolochin, Aristolochine, Descresept, Tardolyt, TR 1736
Identifiers
CAS number 313-67-7 YesY
PubChem 2236
ChemSpider 2149 YesY
KEGG C08469 YesY
ChEMBL CHEMBL93353 YesY
Jmol-3D images Image 1
Properties
Molecular formula C17H11NO7
Molar mass 341.27 g mol−1
Density 1.571g/cm3
Melting point

260 - 265 °C
Boiling point

615.5°C @760mmHg
Solubility in water slightly soluble in water
Hazards
NFPA 704
NFPA 704.svg
1
2
0
Flash point 326°C
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Aristolochic acids are a family of carcinogenic, mutagenic, and nephrotoxic compounds commonly found in the Aristolochiaceae family of plants, including Aristolochia and Asarum (wild ginger), which are commonly used in Chinese herbal medicine.[1][2] Aristolochic acid I is the most abundant of the aristolochic acids and is found in almost all Aristolochia species.[3] Aristolochic acids are often accompanied by aristolactams.[4]

Aristolochic acids are slightly soluble in water, have a melting point between 281 and 286 degrees celsius,[5] and have a bitter flavor.[6]

Contents

Toxicity [edit]

Aristolochic acids are hypothesized to be causative agents in Balkan endemic nephropathy;[7][8][9] and a related—possibly identical—condition known as "Chinese herbs nephropathy".[10] Exposure to aristolochic acid is associated with a high incidence of uroepithelial tumorigenesis,[11] and was linked to aristolochic acid-associated urothelial cancer in a 2012 Taiwanese study.[12]

In April 2001, the Food and Drug Administration issued a consumer health alert warning against consuming botanical products, sold as "traditional medicines" or as ingredients in dietary supplements, containing aristolochic acid.[13] The agency warned that consumption of aristolochic acid-containing products was associated with "permanent kidney damage, sometimes resulting in kidney failure that has required kidney dialysis or kidney transplantation. In addition, some patients have developed certain types of cancers, most often occurring in the urinary tract."[13]

See also [edit]

References [edit]

  1. ^ Heinrich M, Chan J, Wanke S, Neinhuis C, Simmonds MS (August 2009). "Local uses of Aristolochia species and content of nephrotoxic aristolochic acid 1 and 2--a global assessment based on bibliographic sources". J Ethnopharmacol 125 (1): 108–44. doi:10.1016/j.jep.2009.05.028. PMID 19505558. 
  2. ^ Nolin, Thomas D. & Himmelfarb, Jonathan (2010). "Mechanisms of drug-induced nephrotoxicity". In Uetrecht, Jack. Adverse Drug Reactions. Springer. p. 123. ISBN 978-3-642-00662-3. 
  3. ^ Wu, Tian-Shung et al. (2005). "Chemical constituents and pharmacology of Aristolochia species". In Rahman, Atta-ur. Studies in Natural Products Chemistry: Bioactive Natural Products (Part L). Gulf Professional Publishing. p. 863. ISBN 978-0-444-52171-2. 
  4. ^ Wink, Michael & Schimmer, Oskar (1999). "Modes of action of defensive secondary metabolites". In Wink, Michael. Functions of plant secondary metabolites and their exploitation in biotechnology. CRC Press. p. 75. ISBN 978-0-8493-4086-4. 
  5. ^ Barceloux, Donald G. (2008). "Aristolochic acid and Chinese Herb nephropathy". Medical toxicology of natural substances: foods, fungi, medicinal herbs, plants, and venomous animals. John Wiley & Sons. p. 384. ISBN 978-0-471-72761-3. 
  6. ^ Offermanns, S. & Amara, Susan G., ed. (2006). Reviews of physiology, biochemistry and pharmacology, Volume 154. Birkhäuser. p. 56. ISBN 978-3-540-30384-8. 
  7. ^ Gluhovschi G, Margineanu F, Velciov S, Gluhovschi C, Bob F, Petrica L, Bozdog G, Trandafirescu V, Modalca M (January 2011). "Fifty years of Balkan endemic nephropathy in Romania: some aspects of the endemic focus in the Mehedinti county". Clin. Nephrol. 75 (1): 34–48. PMID 21176749. 
  8. ^ Geacintov, Nicholas E. & Broyde, Suse, ed. (2010). "Introduction and perspectives on the Chemistry and Biology of DNA Damage". The Chemical Biology of DNA Damage. Wiley-VCH. p. 7. ISBN 978-3-527-32295-4. 
  9. ^ Wild, Chris et al., ed. (2008). Molecular epidemiology of chronic diseases. John Wiley & Sons. p. 113. ISBN 978-0-470-02743-1. 
  10. ^ De Broe ME (March 2012). "Chinese herbs nephropathy and Balkan endemic nephropathy: toward a single entity, aristolochic acid nephropathy". Kidney Int. 81 (6): 513–5. doi:10.1038/ki.2011.428. PMID 22373701. 
  11. ^ Ronco, Claudio et al., ed. (2008). Critical care nephrology. Elsevier Health Sciences. p. 1699. ISBN 978-1-4160-4252-5. 
  12. ^ Chen CH, Dickman KG, Moriya M, Zavadil J, Sidorenko VS, Edwards KL, Gnatenko DV, Wu L, Turesky RJ, Wu XR, Pu YS, Grollman AP (May 2012). "Aristolochic acid-associated urothelial cancer in Taiwan". Proc. Natl. Acad. Sci. U.S.A. 109 (21): 8241–6. doi:10.1073/pnas.1119920109. PMC 3361449. PMID 22493262. 
  13. ^ a b FDA Warns Consumers to Discontinue Use of Botanical Products that Contain Aristolochic acid. April 11, 2001.

14.Links : www.timesofindia.indiatimes.com/home/science/Herbal-medicines-causing-kidney-failure-bladder-cancer-in-India/articleshow/19052908.cms

Further reading [edit]

  • Aronson, J.K. (2008). "Aristolochicae". Meyler's side effects of herbal medicines. Elsevier. p. 55. ISBN 978-0-444-53269-5. 
  • Lai M., 2009. Journal of National Cancer Institute. doi:10.1093/jnci/djp467. (Short summary published as "Chinese herbal products containing aristolochic acid were associated with urinary tract cancer" in "HemOnc today", page 28, dated 2010-01-25.)
  • Mills, Simon & Bone, Kerry (2005). "Aristolochic Acid Nephropathy". The essential guide to herbal safety. Elsevier Health Sciences. p. 15. ISBN 978-0-443-07171-3. 
  • Wing-Tat Poon, Chi-Kong Lai, Albert Yan-Wo Chan, 2007. "Aristolochic Acid Nephropathy: The Hong Kong Perspective." Hong Kong Journal of Nephrology, 9(1):7-14.

External links [edit]

Wikimedia Commons has media related to: Aristolochic acid
Retrieved from "http://en.wikipedia.org/w/index.php?title=Aristolochic_acid&oldid=546888368"