Cichoric acid

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Cichoric acid
IUPAC name

(2R,3R)-2,3-bis{[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid

Other names

2R,3R-O-dicaffeoyltartaric acid

Identifiers
CAS number 6537-80-0 YesY
PubChem 5281764
ChemSpider 4445078 N
KEGG C10437 YesY
ChEMBL CHEMBL282731 N
Jmol-3D images {{#if: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|Image 1
Properties
Molecular formula C22H18O12
Molar mass 474.371 g/mol
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Cichoric acid is a hydroxycinnamic acid, an organic compound of the phenylpropanoid class and occurs in a variety of plant species. It is a derivative of both caffeic acid and tartaric acid.[1] As a suitable marker for the distinction of Echinacea species, it is often assayed using RP-HPLC and Thin layer chromatography (TLC) methods.[2]

Sources

Cichoric acid has first been isolated from Cichorium intybus (chicory) but also occurs in significant amounts in Echinacea, in particular E. purpurea, dandelion leaves, basil, lemon balm, and aquatic plants, including algae and sea grasses.[3][4]

Biological functions

Cichoric acid has been shown to stimulate phagocytosis in both in vitro and in vivo studies, to inhibit the function of hyaluronidase (an enzyme that breaks down hyaluronic acid in the human body), to protect collagen from damage due to free radicals, and to inhibit the function of HIV-1 integrase.[5][6]

See also

References

  1. ↑ Hall III, Clifford; Jurgen G. Schwarz (2002) John Shi, G. Mazza, Marc Le Maguer, ed. Functional Foods: Biochemical & Processing Aspects 2 CRC Press p. 241 ISBN 1-56676-902-7 retrieved 2008-12-09 
  2. ↑ Bauer R, Khan IA, Wagner H. Echinacea-Drogen, Standardisierung mittels HPLC und DC. Deutsche Apotheker Zeitung, 1986, 126:1065–1070. Citation in WHO Monographs on Selected Medicinal Plants - Volume 1
  3. ↑ I.D. Chkhikvishvili and G.I. Kahrebava (2001). "Cichoric and Chlorogenic Acids in Plant Species from Georgia". Applied Biochemistry and Microbiology, 37 (2): 188-191. doi:10.1023/a:1002888016985
  4. ↑ Jungmin Lee (2010). Short communication "Caffeic acid derivatives in dried Lamiaceae and Echinacea purpurea products". Journal of Functional Foods 2, 158-162. doi:10.1016/j.jff.2010.02.003
  5. ↑ Mazza, G.; Oomah, B. Dave (2000), Herbs, Botanicals & Teas, CRC Press, p. 51, ISBN 1-56676-851-9, retrieved 2008-12-09 
  6. ↑ Miller, Sandra Carol; Yu, He-Ci (2004), Echinacea, CRC Press, p. 140, ISBN 0-415-28828-2, retrieved 2008-12-09 


Aglycones
Precursor
Monohydroxycinnamic acids
(Coumaric acids)
Trihydroxycinnamic acids
  • 3,4,6-Trihydroxycinnamic acid
O-methylated forms
others
Esters
glycoside-likes
Esters of
caffeic acid
with cyclitols
esters of
quinic acid
  • Chlorogenic acid (3-caffeoylquinic acid)
  • Cryptochlorogenic acid (4-O-caffeoylquinic acid)
  • Neochlorogenic acid (5-O-Caffeoylquinic acid)
  • Cynarine (1,5-dicaffeoylquinic acid)
  • 3,4-dicaffeoylquinic acid
  • 3,5-dicaffeoylquinic acid
esters of
shikimic acid
Glycosides
Tartaric acid esters
Other esters
with caffeic acid
Oligomeric forms
Dimers
Trimers
Tetramers
  • Tetraferulic acids
Conjugates with coenzyme A
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