Hydroxycitric acid

Hydroxycitric acid
Names
Preferred IUPAC name
1,2-Dihydroxypropane-1,2,3-tricarboxylic acid
Other names
Hydroxycitrate (anion name)
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C6H8O8/c7-2(8)1-6(14,5(12)13)3(9)4(10)11/h3,9,14H,1H2,(H,7,8)(H,10,11)(H,12,13) checkY
    Key: ZMJBYMUCKBYSCP-UHFFFAOYSA-N checkY
  • InChI=1/C6H8O8/c7-2(8)1-6(14,5(12)13)3(9)4(10)11/h3,9,14H,1H2,(H,7,8)(H,10,11)(H,12,13)
    Key: ZMJBYMUCKBYSCP-UHFFFAOYAQ
  • O=C(O)C(O)C(O)(C(=O)O)CC(=O)O
Properties
C6H8O8
Molar mass 208.122 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Hydroxycitric acid (HCA) is a derivative of citric acid that is found in a variety of tropical plants including Garcinia cambogia and Hibiscus sabdariffa.

There are four isomers, (+)- and (-)-hydroxycitric acid, and (+)- and (-)-allo-hydroxycitric acid. The (-)-hydroxycitric acid isomer is the one found in Garcinia.

Chemistry

Hydroxycitric acid as such cannot be isolated from garcinia fruits or hibiscus sabdariffa fruits. It exists in both the open and lactone forms. The presence of two chiral centres in the molecule is exploited to construct molecular skeletons that are otherwise difficult to synthesize, thus demonstrating the lactones use as chirons.

Biological effects

(-)-HCA is a competitive inhibitor of ATP citrate lyase, which converts citrate into oxaloacetate and acetyl CoA. The reverse of this conversion is a step in the citric acid cycle.

Laboratory and animal studies of HCA have produced results that indicate a potential for modulation of lipid metabolism. A meta-analysis published in 2010 revealed that gastrointestinal adverse effects were twice as likely for users of hydroxycitric acid. The use of HCA is contraindicated in people with colitis or inflammatory bowel disease.

Potential for liver damage

A 2024 review indicated that consuming foods or dietary supplements containing hydroxycitric acid, such as Garcinia products, may cause liver disease.

References

  1. ↑ Yamada T, Hida H, Yamada Y (2007). "Chemistry, physiological properties, and microbial production of hydroxycitric acid". Appl. Microbiol. Biotechnol. 75 (5): 977–82. doi:10.1007/s00253-007-0962-4. PMID 17476502. S2CID 25194835.
  2. 1 2 Jena, BS; Jayaprakasha, GK; Singh, RP; Sakariah, KK (2002-01-02). "Chemistry and biochemistry of (-)-hydroxycitric acid from Garcinia". Journal of Agricultural and Food Chemistry. 50 (1): 10–22. doi:10.1021/jf010753k. PMID 11754536.
  3. ↑ Habel, Deenamma; Nair, Divya S.; Kallingathodi, Zabeera; Mohan, Chithra; Pillai, Sarath M.; Nair, Rani R.; Thomas, Grace; Haleema, Simimole; Gopinath, Chithra; Abdul, Rinshad V.; Fritz, Matthew (2020-07-24). "Natural Product-Derived Chiral Pyrrolidine-2,5-diones, Their Molecular Structures and Conversion to Pharmacologically Important Skeletons". Journal of Natural Products. 83 (7): 2178–2190. doi:10.1021/acs.jnatprod.0c00211. ISSN 0163-3864. PMID 32584573. S2CID 220079442.
  4. ↑ Shara M, Ohia SE, Yasmin T, et al. (2003). "Dose- and time-dependent effects of a novel (−)-hydroxycitric acid extract on body weight, hepatic and testicular lipid peroxidation, DNA fragmentation and histopathological data over a period of 90 days". Mol. Cell. Biochem. 254 (1–2): 339–46. doi:10.1023/A:1027358106407. PMID 14674714. S2CID 25594704.
  5. ↑ Igho O, Shao K, Rachel P, Barbara W, Edzard E (2011). "The Use of Garcinia Extract Hydroxycitric Acid as a Weight loss Supplement: A Systematic Review and Meta-Analysis of Randomised Clinical Trials". J. Obes. 2011 (622): 1–9. doi:10.1155/2011/509038. PMC 3010674. PMID 21197150.
  6. ↑ Philips CA, Theruvath AH (April 2024). "A comprehensive review on the hepatotoxicity of herbs used in the Indian (Ayush) systems of alternative medicine". Medicine (Baltimore). 103 (16) e37903. doi:10.1097/MD.0000000000037903. PMC 11029936. PMID 38640296.