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Chicoric acid

From Wikipedia, the free encyclopedia
Chemical compound
Chicoric acid
Names
Preferred IUPAC name
(2R,3R)-2,3-Bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid
Other names
Cichoric acid; (2R,3R)-O-Dicaffeoyltartaric acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard100.109.212Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)/b7-3+,8-4+/t19-,20-/m1/s1 ☒N
    Key: YDDGKXBLOXEEMN-IABMMNSOSA-N ☒N
  • InChI=1/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)/b7-3+,8-4+/t19-,20-/m1/s1
    Key: YDDGKXBLOXEEMN-IABMMNSOBV
  • O=C(O)[C@H](OC(=O)\C=C\c1ccc(O)c(O)c1)[C@@H](OC(=O)\C=C\c2cc(O)c(O)cc2)C(=O)O
Properties
C22H18O12
Molar mass474.371 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Chicoric acid (also known ascichoric acid) is ahydroxycinnamic acid, an organic compound of thephenylpropanoid class and occurs in a variety of plant species. It is a derivative of bothcaffeic acid andtartaric acid.[1]

As a suitable marker for the distinction ofEchinacea species, it is often assayed usingRP-HPLC andThin layer chromatography (TLC) methods.[2]

Sources

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Chicoric acid has first been isolated fromCichorium intybus (chicory) but also occurs in significant amounts inEchinacea, in particularE. purpurea,dandelion leaves,basil,lemon balm, andaquatic plants, includingalgae andseagrasses.[3][4][5][6]

Biological functions

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Chicoric acid has been shown to stimulatephagocytosis in bothin vitro andin vivo studies, to inhibit the function ofhyaluronidase (an enzyme that breaks downhyaluronic acid in the human body), to protectcollagen from damage due tofree radicals, and to inhibit the function ofHIV-1integrase.[7][8]

See also

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References

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  1. ^John Shi; Giuseppe Mazza; Marc Le Maguer (27 February 2002).Functional Foods: Biochemical and Processing Aspects. CRC Press. pp. 241–.ISBN 978-1-4200-1287-3.
  2. ^Bauer R, Khan IA, Wagner H. Echinacea-Drogen, Standardisierung mittels HPLC und DC. Deutsche Apotheker Zeitung, 1986, 126:1065–1070. Citation inWHO Monographs on Selected Medicinal Plants - Volume 1
  3. ^Chkhikvishvili, I. D.; Kharebava, G. I. (2001). "Chicoric and Chlorogenic Acids in Plant Species from Georgia".Applied Biochemistry and Microbiology.37 (2):188–191.doi:10.1023/a:1002888016985.S2CID 6322156.
  4. ^Lee, Jungmin (2010). "Caffeic acid derivatives in dried Lamiaceae and Echinacea purpurea products".Journal of Functional Foods.2 (2):158–162.doi:10.1016/j.jff.2010.02.003.
  5. ^Lee, Jungmin; Scagel, Carolyn F. (2009). "Chicoric acid found in basil (Ocimum basilicum L.) leaves".Food Chemistry.115 (2):650–656.doi:10.1016/j.foodchem.2008.12.075.
  6. ^Lee, Jungmin; Scagel, Carolyn F. (2013)."Chicoric acid: Chemistry, distribution, and production".Frontiers in Chemistry.1: 40.Bibcode:2013FrCh....1...40L.doi:10.3389/fchem.2013.00040.PMC 3982519.PMID 24790967.
  7. ^Mazza, G.; Oomah, B. Dave (2000),Herbs, Botanicals & Teas, CRC Press, p. 51,ISBN 1-56676-851-9, retrieved2008-12-09
  8. ^Miller, Sandra Carol; Yu, He-Ci (2004),Echinacea, CRC Press, p. 140,ISBN 0-415-28828-2, retrieved2008-12-09
Aglycones
Precursor
Monohydroxycinnamic acids
(Coumaric acids)
Dihydroxycinnamic acids
Trihydroxycinnamic acids
O-methylated forms
others
Esters
glycoside-likes
Esters of
caffeic acid
with cyclitols
esters of
quinic acid
esters of
shikimic acid
Glycosides
Tartaric acid esters
Other esters
with caffeic acid
Caffeoyl phenylethanoid
glycoside (CPG)
Oligomeric forms
Dimers
Trimers
Tetramers
Conjugates with
coenzyme A (CoA)
Retrieved from "https://en.wikipedia.org/w/index.php?title=Chicoric_acid&oldid=1190948544"
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