Chicoric acid

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
CAS Number
  • 6537-80-0 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL282731 ☒N
ChemSpider
  • 4445078 ☒N
ECHA InfoCard 100.109.212 Edit this at Wikidata
KEGG
  • C10437 checkY
PubChem CID
  • 5281764
UNII
  • S4YY3V8YHD checkY
CompTox Dashboard (EPA)
  • DTXSID0033332 Edit this at Wikidata
InChI
  • 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
Chemical formula
 C22H18O12
Molar mass 474.371 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references
Chemical compound

Chicoric acid (also known as 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

Chicoric 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 seagrasses.[3][4][5][6]

Biological functions

Chicoric 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

References

  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 in WHO 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, 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
  • v
  • t
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Aglycones
Precursor
Monohydroxycinnamic acids
(Coumaric acids)
  • p-Coumaric acid
  • o-Coumaric acid
  • m-Coumaric acid
Dihydroxycinnamic acids
Trihydroxycinnamic acids
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
  • Ferulic acid glucoside
  • p-Coumaric acid glucoside
  • 1-Sinapoyl-D-glucose
Tartaric acid esters
Other esters
with caffeic acid
Caffeoyl phenylethanoid
glycoside (CPG)
  • Echinacoside
  • Calceolarioside A, B, C, F
  • Chiritoside A, B, C
  • Cistanoside A, B, C, D, E, F, G, H
  • Conandroside
  • Myconoside
  • Pauoifloside
  • Plantainoside A
  • Plantamajoside
  • Tubuloside B
  • Verbascoside (Isoverbascoside, 2′-Acetylverbascoside)
Oligomeric forms
Dimers
Trimers
Tetramers
  • Tetraferulic acids
Conjugates with
coenzyme A (CoA)