Cichoric acid

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Cichoric acid
Chicoric acid.svg
Names
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
6537-80-0 YesY
ChEMBL ChEMBL282731 N
ChemSpider 4445078 N
Jmol-3D images Image
KEGG C10437 YesY
PubChem 5281764
Properties
C22H18O12
Molar mass 474.371 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
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[edit]

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][5][6]

Biological functions[edit]

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.[7][8]

See also[edit]

References[edit]

  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. [1] doi:10.1023/a:1002888016985
  4. ^ Lee J. (2010). "Caffeic acid derivatives in dried Lamiaceae and Echinacea purpurea products". Journal of Functional Foods 2, 158-162. [2]doi|10.1016/j.jff.2010.02.003
  5. ^ Lee J. Scagel, C.F. (2009). "Chicoric acid found in basil (Ocimum basilicum L.) leaves.". Food Chemistry 115, 650-656. [3]doi:10.1016/j.foodchem.2008.12.075
  6. ^ Lee J. Scagel, C.F. (2013). "Chicoric acid: chemistry, distribution, and production". Frontiers in Chemistry 1:40. [4]doi: 10.3389/fchem.2013.00040
  7. ^ Mazza, G.; Oomah, B. Dave (2000), Herbs, Botanicals & Teas, CRC Press, p. 51, ISBN 1-56676-851-9, retrieved 2008-12-09 
  8. ^ Miller, Sandra Carol; Yu, He-Ci (2004), Echinacea, CRC Press, p. 140, ISBN 0-415-28828-2, retrieved 2008-12-09