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{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 400112197 | verifiedrevid = 440298418
|ImageFile=Hydroxycitric acid.png | ImageFile=Hydroxycitric acid.png
|ImageSize=200px | ImageSize=200px
|IUPACName=1,2-dihydroxypropane-1,2,3-tricarboxylic acid | PIN=1,2-Dihydroxypropane-1,2,3-tricarboxylic acid
|OtherNames=Hydroxycitrate | OtherNames=Hydroxycitrate (anion name)
|Section1= {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 110439 | ChemSpiderID = 110439
| 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) | 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)
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| StdInChIKey = ZMJBYMUCKBYSCP-UHFFFAOYSA-N | StdInChIKey = ZMJBYMUCKBYSCP-UHFFFAOYSA-N
| CASNo=6205-14-7 | CASNo=6205-14-7
| CASNo_Ref = {{cascite|correct|CAS}}
⚫ | PubChem=123908
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | SMILES = O=C(O)C(O)C(O)(C(=O)O)CC(=O)O
| UNII = 8W94T9026R
⚫ | PubChem=123908
⚫ | SMILES = O=C(O)C(O)C(O)(C(=O)O)CC(=O)O
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| C=6 | H=8 | O=8
| Formula=C<sub>6</sub>H<sub>8</sub>O<sub>8</sub>
| Appearance=
| MolarMass=208.12292
| Appearance= | Density=
| Density= | MeltingPt=
| MeltingPt= | BoilingPt=
| BoilingPt= | Solubility=
| Solubility=
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}


'''Hydroxycitric acid''' (HCA) is a derivative of ] that is found in a variety of tropical plants including '']'' and '']''.<ref name="Yamada" />
'''Hydroxycitric acid''' (HCA) is a derivative of ] that is found in a variety of tropical plants including '']'' and '']''.<ref name="Yamada">{{cite journal |author=Yamada T, Hida H, Yamada Y |title=Chemistry, physiological properties, and microbial production of hydroxycitric acid |journal=Appl. Microbiol. Biotechnol. |volume=75 |issue=5 |pages=977–82 |year=2007 |pmid=17476502 |doi=10.1007/s00253-007-0962-4}}</ref> Laboratory and animal studies of HCA have produced results that indicate a potential for modulation of lipid metabolism;<ref name="Shara">{{cite journal |author=Shara M, Ohia SE, Yasmin T, ''et al.'' |title=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 |journal=Mol. Cell. Biochem. |volume=254 |issue=1–2 |pages=339–46 |year=2003 |pmid=14674714 |doi=10.1023/A:1027358106407}}</ref> consequently HCA is an ingredient in some weight loss products and dietary supplements. However, a clinical study has demonstrated that HCA has no effect in terms of weight loss or reduction of fat mass.<ref>{{cite journal | journal = JAMA | year = 1998 | volume = 280 | issue = 18 | pages = 1596–600 | title = Garcinia cambogia (hydroxycitric acid) as a potential antiobesity agent: a randomized controlled trial | author = Heymsfield SB, Allison DB, Vasselli JR, Pietrobelli A, Greenfield D, Nunez C. | doi = 10.1001/jama.280.18.1596 | pmid = 9820262}}</ref>


There are four isomers, (+)- and (-)-hydroxycitric acid, and (+)- and (-)-allo-hydroxycitric acid. The (-)-hydroxycitric acid isomer is the one found in '']''.<ref name="Chemistry and biochemistry of --h">{{cite journal |last1=Jena |first1=BS |last2=Jayaprakasha |first2=GK |last3=Singh |first3=RP |last4=Sakariah |first4=KK |title=Chemistry and biochemistry of (-)-hydroxycitric acid from Garcinia. |journal=Journal of Agricultural and Food Chemistry |date=2002-01-02 |volume=50 |issue=1 |pages=10–22 |doi=10.1021/jf010753k |pmid=11754536}}</ref>
One ] of HCA, known as (2''S'',3''R'')-HCA, inhibits pancreatic ] and intestinal ], leading to a reduction in carbohydrate metabolism '']''.<ref name="Yamada"/> In a study in ]s, which are genetically predisposed to obesity, ''Garcinia cambogia'' extract containing HCA showed that high doses led to significant suppression of epididymal fat accumulation, but also caused potent testicular atrophy and toxicity.<ref name="Saito">{{cite journal |author=Saito M, Ueno M, Ogino S, Kubo K, Nagata J, Takeuchi M |title=High dose of Garcinia cambogia is effective in suppressing fat accumulation in developing male Zucker obese rats, but highly toxic to the testis |journal=Food Chem. Toxicol. |volume=43 |issue=3 |pages=411–9 |year=2005 |pmid=15680676 |doi=10.1016/j.fct.2004.11.008}}</ref> However, this study has been criticized because of possible contamination of the HCA used and various design flaws.<ref>{{cite journal | author = Madhusudan Soni Burdock Group | year = 2005 | title = Garcinia cambogia toxicity is misleading | journal = Food and Chemical Toxicology | volume = 43 | issue = 11 | pages = 1683–1684 | doi = 10.1016/j.fct.2005.05.011 | pmid = 15993998}}</ref><ref>{{cite journal | pmid = 18316163 | year = 2008 | last1 = Hayamizu | first1 = K | last2 = Tomi | first2 = H | last3 = Kaneko | first3 = I | last4 = Shen | first4 = M | last5 = Soni | first5 = MG | last6 = Yoshino | first6 = G | title = Effects of Garcinia cambogia extract on serum sex hormones in overweight subjects | volume = 79 | issue = 4 | pages = 255–61 | doi = 10.1016/j.fitote.2007.12.003 | journal = Fitoterapia}}</ref>

==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.<ref>{{Cite journal|last1=Habel|first1=Deenamma|last2=Nair|first2=Divya S.|last3=Kallingathodi|first3=Zabeera|last4=Mohan|first4=Chithra|last5=Pillai|first5=Sarath M.|last6=Nair|first6=Rani R.|last7=Thomas|first7=Grace|last8=Haleema|first8=Simimole|last9=Gopinath|first9=Chithra|last10=Abdul|first10=Rinshad V.|last11=Fritz|first11=Matthew|date=2020-07-24|title=Natural Product-Derived Chiral Pyrrolidine-2,5-diones, Their Molecular Structures and Conversion to Pharmacologically Important Skeletons|url=https://pubs.acs.org/doi/10.1021/acs.jnatprod.0c00211|journal=Journal of Natural Products|language=en|volume=83|issue=7|pages=2178–2190|doi=10.1021/acs.jnatprod.0c00211|pmid=32584573|s2cid=220079442 |issn=0163-3864}}</ref>

==Biological effects==
(-)-HCA is a competitive inhibitor of ], which converts citrate into ] and ].<ref name="Chemistry and biochemistry of --h"/> The reverse of this conversion is a step in the ].

Laboratory and animal studies of HCA have produced results that indicate a potential for modulation of lipid metabolism.<ref name="Shara" /> However, a clinical study has demonstrated that HCA has no effect in terms of weight loss or reduction of fat mass.<ref name="Heymsfield" /> 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 patients suffering Colitis or Inflammatory Bowel Disease.<ref name="Igho" />

One ] of HCA, known as (2''S'',3''R'')-HCA, inhibits pancreatic ] and intestinal ], leading to a reduction in carbohydrate metabolism '']''.<ref name="Yamada"/> In a study in ]s, which are genetically predisposed to obesity, ''Garcinia cambogia'' extract containing HCA showed that high doses led to significant suppression of ] fat accumulation, but also had high testicular toxicity.<ref name="Saito" /> However, this study has been criticized because of possible contamination of the HCA used and various design flaws.<ref name=MSBG /><ref name=Hayamizu />

Researchers at the ] reported hydroxycitrate is capable of dissolving ] crystals, a component of human kidney stones. Recent studies (2019) shows kidney stones are layered and the stones may form and dissolve with time. The researchers believe the effect could lead to the development of new drugs for human kidney stones.<ref name=Chung />


==References== ==References==

{{reflist}} {{reflist|refs=
<ref name="Yamada">{{cite journal |vauthors=Yamada T, Hida H, Yamada Y |title=Chemistry, physiological properties, and microbial production of hydroxycitric acid |journal=Appl. Microbiol. Biotechnol. |volume=75 |issue=5 |pages=977–82 |year=2007 |pmid=17476502 |doi=10.1007/s00253-007-0962-4|s2cid=25194835 }}</ref>
<ref name="Shara">{{cite journal |vauthors=Shara M, Ohia SE, Yasmin T, etal |title=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 |journal=Mol. Cell. Biochem. |volume=254 |issue=1–2 |pages=339–46 |year=2003 |pmid=14674714 |doi=10.1023/A:1027358106407|s2cid=25594704 }}</ref>
<ref name="Heymsfield">{{cite journal | journal = JAMA | year = 1998 | volume = 280 | issue = 18 | pages = 1596–600 | title = Garcinia cambogia (hydroxycitric acid) as a potential antiobesity agent: a randomized controlled trial |vauthors=Heymsfield SB, Allison DB, Vasselli JR, Pietrobelli A, Greenfield D, Nunez C | doi = 10.1001/jama.280.18.1596 | pmid = 9820262| doi-access = }}</ref>
<ref name="Igho">{{cite journal |vauthors=Igho O, Shao K, Rachel P, Barbara W, Edzard E |title=The Use of Garcinia Extract Hydroxycitric Acid as a Weight loss Supplement: A Systematic Review and Meta-Analysis of Randomised Clinical Trials |journal=J. Obes. |volume=2011 |issue=622 |year=2011 |pmid=21197150 |pmc=3010674 |doi=10.1155/2011/509038 |pages=1–9|doi-access=free }}</ref>
<ref name="Saito">{{cite journal |vauthors=Saito M, Ueno M, Ogino S, Kubo K, Nagata J, Takeuchi M |title=High dose of Garcinia cambogia is effective in suppressing fat accumulation in developing male Zucker obese rats, but highly toxic to the testis |journal=] |volume=43 |issue=3 |pages=411–9 |year=2005 |pmid=15680676 |doi=10.1016/j.fct.2004.11.008}}</ref>
<ref name=MSBG>{{cite journal |author= Madhusudan Soni Burdock Group | year= 2005 | title= Garcinia cambogia toxicity is misleading |journal= ] |volume=43 |issue=11 |pages=1683–1684 |doi=10.1016/j.fct.2005.05.011 |pmid=15993998}}</ref>
<ref name=Hayamizu>{{cite journal |pmid= 18316163 |year=2008 |last1=Hayamizu |first1=K |last2=Tomi |first2=H |last3=Kaneko | first3=I | last4=Shen |first4=M | last5= Soni |first5=MG |last6=Yoshino |first6=G |title=Effects of Garcinia cambogia extract on serum sex hormones in overweight subjects |volume=79 |issue=4 |pages=255–61 |doi= 10.1016/j.fitote.2007.12.003 |journal=Fitoterapia}}</ref>
<ref name=Chung>{{cite journal |vauthors=Chung J, Granja I, Taylor M, Mpourmpakis G, Asplin J |title=Molecular modifiers reveal a mechanism of pathological crystal growth inhibition |journal=] |year=2016 |volume=536 |issue=7617 |pages=446–450 |doi=10.1038/nature19062|pmid=27501150 |bibcode=2016Natur.536..446C |s2cid=4452431 }}</ref>
}}


{{DEFAULTSORT:Hydroxycitric Acid}} {{DEFAULTSORT:Hydroxycitric Acid}}
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