Hydroxycitric acid

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Hydroxycitric acid
Hydroxycitric acid.png
Names
Preferred IUPAC name
1,2-Dihydroxypropane-1,2,3-tricarboxylic acid
Other names
Hydroxycitrate (anion name)
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
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) Yes check.svgY
    Key: ZMJBYMUCKBYSCP-UHFFFAOYSA-N Yes check.svgY
  • 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Hydroxycitric acid (HCA) is a derivative of citric acid that is found in a variety of tropical plants including Garcinia cambogia and Hibiscus sabdariffa . [1]

Contents

There are four isomers, (+)- and (-)-hydroxycitric acid, and (+)- and (-)-allo-hydroxycitric acid. The (-)-hydroxycitric acid isomer is the one found in Garcinia . [2]

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. [3]

Biological effects

(-)-HCA is a competitive inhibitor of ATP citrate lyase, which converts citrate into oxaloacetate and acetyl CoA. [2] 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. [4] However, a clinical study has demonstrated that HCA has no effect in terms of weight loss or reduction of fat mass. [5] 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. [6]

One isomer of HCA, known as (2S,3R)-HCA, inhibits pancreatic alpha-amylase and intestinal alpha-glucosidase, leading to a reduction in carbohydrate metabolism in vitro . [1] In a study in Zucker rats, 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 had high testicular toxicity. [7] However, this study has been criticized because of possible contamination of the HCA used and various design flaws. [8] [9]

Researchers at the University of Houston reported hydroxycitrate is capable of dissolving calcium oxalate 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. [10]

Related Research Articles

<span class="mw-page-title-main">Citric acid cycle</span> Interconnected biochemical reactions releasing energy

The citric acid cycle—also known as the Krebs cycle, Szent-Györgyi-Krebs cycle or the TCA cycle (tricarboxylic acid cycle)—is a series of biochemical reactions to release the energy stored in nutrients through the oxidation of acetyl-CoA derived from carbohydrates, fats, and proteins. The chemical energy released is available under the form of ATP. The Krebs cycle is used by organisms that respire (as opposed to organisms that ferment) to generate energy, either by anaerobic respiration or aerobic respiration. In addition, the cycle provides precursors of certain amino acids, as well as the reducing agent NADH, that are used in numerous other reactions. Its central importance to many biochemical pathways suggests that it was one of the earliest components of metabolism. Even though it is branded as a 'cycle', it is not necessary for metabolites to follow only one specific route; at least three alternative segments of the citric acid cycle have been recognized.

<span class="mw-page-title-main">Citric acid</span> Weak organic acid

Citric acid is an organic compound with the chemical formula HOC(CO2H)(CH2CO2H)2. It is a colorless weak organic acid. It occurs naturally in citrus fruits. In biochemistry, it is an intermediate in the citric acid cycle, which occurs in the metabolism of all aerobic organisms.

<span class="mw-page-title-main">Tartaric acid</span> Organic acid found in many fruits

Tartaric acid is a white, crystalline organic acid that occurs naturally in many fruits, most notably in grapes, but also in tamarinds, bananas, avocados and citrus. Its salt, potassium bitartrate, commonly known as cream of tartar, develops naturally in the process of fermentation. It is commonly mixed with sodium bicarbonate and is sold as baking powder used as a leavening agent in food preparation. The acid itself is added to foods as an antioxidant E334 and to impart its distinctive sour taste. Naturally occurring tartaric acid is a useful raw material in organic chemical synthesis. Tartaric acid, an alpha-hydroxy-carboxylic acid, is diprotic and aldaric in acid characteristics, and is a dihydroxyl derivative of succinic acid.

<i>Hibiscus</i> Genus of plants

Hibiscus is a genus of flowering plants in the mallow family, Malvaceae. The genus is quite large, comprising several hundred species that are native to warm temperate, subtropical and tropical regions throughout the world. Member species are renowned for their large, showy flowers and those species are commonly known simply as "hibiscus", or less widely known as rose mallow. Other names include hardy hibiscus, rose of sharon, and tropical hibiscus.

<i>Garcinia</i> Genus of flowering plants

Garcinia is a genus of flowering plants in the family Clusiaceae native to Asia, America, Australia, tropical and southern Africa, and Polynesia. The number of species is disputed; Plants of the World Online (POWO) recognise up to 400. Commonly, the plants in this genus are called saptrees, mangosteens, or garcinias, and is one of several plants known as by the name "monkey fruit".

<span class="mw-page-title-main">Calcium citrate</span> Chemical compound

Calcium citrate is the calcium salt of citric acid. It is commonly used as a food additive (E333), usually as a preservative, but sometimes for flavor. In this sense, it is similar to sodium citrate. Calcium citrate is also found in some dietary calcium supplements. Calcium makes up 24.1% of calcium citrate (anhydrous) and 21.1% of calcium citrate (tetrahydrate) by mass. The tetrahydrate occurs in nature as the mineral Earlandite.

<i>Garcinia gummi-gutta</i> Species of flowering plant

Garcinia gummi-gutta is a tropical species of Garcinia native to South Asia and Southeast Asia. Common names include Garcinia cambogia, as well as brindle berry, and Malabar tamarind. The fruit looks like a small pumpkin and is green to pale yellow in color.

<span class="mw-page-title-main">Chlorogenic acid</span> Chemical compound

Chlorogenic acid (CGA) is the ester of caffeic acid and (−)-quinic acid, functioning as an intermediate in lignin biosynthesis. The term "chlorogenic acids" refers to a related polyphenol family of esters, including hydroxycinnamic acids with quinic acid.

<span class="mw-page-title-main">Caffeine citrate</span> Medication

Caffeine citrate, sold under the brand name Cafcit among others, is a medication used to treat a lack of breathing in premature babies. Specifically it is given to babies who are born at less than 35 weeks or weigh less than 2 kilograms (4.4 lb) once other causes are ruled out. It is given by mouth or slow injection into a vein.

<span class="mw-page-title-main">Hibiscus tea</span> Drink made from sepals of Hibiscus sabdariffa

Hibiscus tea is a herbal tea made as an infusion from crimson or deep magenta-colored calyces (sepals) of the roselle flower. It is consumed both hot and cold. It has a tart, cranberry-like flavor.

<span class="mw-page-title-main">Magnesium citrate</span> Chemical compound

Magnesium citrate is a magnesium preparation in salt form with citric acid in a 1:1 ratio. It contains 11.23% magnesium by weight.

Isocitric acid is a structural isomer of citric acid. Since citric acid and isocitric acid are structural isomers, they share similar physical and chemical properties. Due to these similar properties, it is difficult to separate the isomers. Salts and esters of isocitric acid are known as isocitrates. The isocitrate anion is a substrate of the citric acid cycle. Isocitrate is formed from citrate with the help of the enzyme aconitase, and is acted upon by isocitrate dehydrogenase.

<span class="mw-page-title-main">Fenoprofen</span> NSAID analgesic and anti-inflammatory drug

Fenoprofen, sold under the brand name Nalfon among others, is a nonsteroidal anti-inflammatory drug (NSAID). Fenoprofen calcium is used for symptomatic relief for rheumatoid arthritis, osteoarthritis, and mild to moderate pain. It has also been used to treat postoperative pain. It is available as a generic medication.

Sodium citrate may refer to any of the sodium salts of citric acid :

<span class="mw-page-title-main">Protocatechuic acid</span> Chemical compound

Protocatechuic acid (PCA) is a dihydroxybenzoic acid, a type of phenolic acid. It is a major metabolite of antioxidant polyphenols found in green tea. It has mixed effects on normal and cancer cells in in vitro and in vivo studies.

<span class="mw-page-title-main">Diethyl phthalate</span> Chemical compound

Diethyl phthalate (DEP) is a phthalate ester. It occurs as a colourless liquid without significant odour but has a bitter, disagreeable taste. It is more dense than water and insoluble in water; hence, it sinks in water.

<i>Garcinia atroviridis</i> Species of tree

Garcinia atroviridis, known as asam gelugur, asam gelugo, or asam keping is a large rainforest tree native to Peninsular Malaysia and Sumatra. This species grows wild throughout Peninsular Malaysia but is also widely cultivated, especially in the northern states, owing to its economic and medicinal value. Garcinia atroviridis is a large perennial plant commonly found in evergreen forests in the southern region of Thailand and Malaysia.

<span class="mw-page-title-main">Gambogic acid</span> Chemical compound

Gambogic acid is a xanthonoid that is derived from the brownish or orange resin from Garcinia hanburyi. Garcinia hanburyi is a small to medium-sized evergreen tree with smooth grey bark. It is native to Cambodia, southern Vietnam, and Thailand and has been successfully introduced in Singapore.

<span class="mw-page-title-main">Methyl fluoroacetate</span> Chemical compound

Methyl fluoroacetate (MFA) is an extremely toxic methyl ester of fluoroacetic acid. It is a colorless, odorless liquid at room temperature. It is used as a laboratory chemical and as a rodenticide. Because of its extreme toxicity, MFA was studied for potential use as a chemical weapon.

Alkali citrate is an inhibitor of kidney stones. It is used to increase urine citrate levels - this prevents calcium oxalate stones by binding to calcium and inhibiting its binding to oxalate. It is also used to increase urine pH - this prevents uric acid stones and cystine stones.

References

  1. 1 2 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. ↑ Heymsfield SB, Allison DB, Vasselli JR, Pietrobelli A, Greenfield D, Nunez C (1998). "Garcinia cambogia (hydroxycitric acid) as a potential antiobesity agent: a randomized controlled trial". JAMA. 280 (18): 1596–600. doi:10.1001/jama.280.18.1596. PMID   9820262.
  6. ↑ 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.
  7. ↑ Saito M, Ueno M, Ogino S, Kubo K, Nagata J, Takeuchi M (2005). "High dose of Garcinia cambogia is effective in suppressing fat accumulation in developing male Zucker obese rats, but highly toxic to the testis". Food Chem. Toxicol. 43 (3): 411–9. doi:10.1016/j.fct.2004.11.008. PMID   15680676.
  8. ↑ Madhusudan Soni Burdock Group (2005). "Garcinia cambogia toxicity is misleading". Food and Chemical Toxicology . 43 (11): 1683–1684. doi:10.1016/j.fct.2005.05.011. PMID   15993998.
  9. ↑ Hayamizu, K; Tomi, H; Kaneko, I; Shen, M; Soni, MG; Yoshino, G (2008). "Effects of Garcinia cambogia extract on serum sex hormones in overweight subjects". Fitoterapia. 79 (4): 255–61. doi:10.1016/j.fitote.2007.12.003. PMID   18316163.
  10. ↑ Chung J, Granja I, Taylor M, Mpourmpakis G, Asplin J (2016). "Molecular modifiers reveal a mechanism of pathological crystal growth inhibition". Nature . 536 (7617): 446–450. Bibcode:2016Natur.536..446C. doi:10.1038/nature19062. PMID   27501150. S2CID   4452431.
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