Chicoric acid

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Chicoric acid
Chicoric acid.svg
Cichoric acid-3D-balls.png
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 InfoCard 100.109.212 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
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 X mark.svgN
    Key: YDDGKXBLOXEEMN-IABMMNSOSA-N X mark.svgN
  • 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 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).
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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]

Contents

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

Related Research Articles

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4-Aminobenzoic acid (also known as para-aminobenzoic acid or PABA because the two functional groups are attached to the benzene ring across from one another in the para position) is an organic compound with the formula H2NC6H4CO2H. PABA is a white solid, although commercial samples can appear gray. It is slightly soluble in water. It consists of a benzene ring substituted with amino and carboxyl groups. The compound occurs extensively in the natural world.

<span class="mw-page-title-main">Phytochemistry</span> Study of phytochemicals, which are chemicals derived from plants

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<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">Caffeic acid</span> Chemical compound

Caffeic acid is an organic compound that is classified as a hydroxycinnamic acid. This yellow solid consists of both phenolic and acrylic functional groups. It is found in all plants because it is an intermediate in the biosynthesis of lignin, one of the principal components of woody plant biomass and its residues.

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

Ferulic acid is a hydroxycinnamic acid, is an organic compound with the formula (CH3O)HOC6H3CH=CHCO2H. The name is derived from the genus Ferula, referring to the giant fennel (Ferula communis). Classified as a phenolic phytochemical or polyphenol, ferulic acid is an amber colored solid. Esters of ferulic acid are found in plant cell walls, covalently bonded to hemicellulose such as arabinoxylans. Salts and esters derived from ferulic acid are called ferulates.

<i>Ipomoea purpurea</i> Species of plant

Ipomoea purpurea, the common morning-glory, tall morning-glory, or purple morning glory, is a species in the genus Ipomoea, native to Mexico and Central America.

Hydroxycinnamic acids (hydroxycinnamates) are a class of aromatic acids or phenylpropanoids having a C6–C3 skeleton. These compounds are hydroxy derivatives of cinnamic acid.

<i>Echinacea purpurea</i> Species of flowering plant in the daisy family Asteraceae

Echinacea purpurea, the eastern purple coneflower, purple coneflower, hedgehog coneflower, or echinacea, is a North American species of flowering plant in the family Asteraceae. It is native to parts of eastern North America and present to some extent in the wild in much of the eastern, southeastern and midwestern United States as well as in the Canadian Province of Ontario. It is most common in the Ozarks and in the Mississippi/Ohio Valley. Its habitats include dry open woods, prairies and barrens.

<span class="mw-page-title-main">Rosmarinic acid</span> Chemical compound found in a variety of plants

Rosmarinic acid, named after rosemary, is a polyphenol constituent of many culinary herbs, including rosemary, perilla, sage, mint, and basil.

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

Caftaric acid is a non-flavonoid phenolic compound.

<span class="mw-page-title-main">Thiosulfinate</span> Functional group

In organosulfur chemistry, thiosulfinate is a functional group consisting of the linkage R-S(O)-S-R. Thiolsulfinates are also named as alkanethiosulfinic acid esters.

<span class="mw-page-title-main">Phenolic acid</span> Class of chemical compounds

Phenolic acids or phenolcarboxylic acids are types of aromatic acid compounds. Included in that class are substances containing a phenolic ring and an organic carboxylic acid function. Two important naturally occurring types of phenolic acids are hydroxybenzoic acids and hydroxycinnamic acids, which are derived from non-phenolic molecules of benzoic and cinnamic acid, respectively.

<span class="mw-page-title-main">Naturally occurring phenols</span> Group of chemical compounds

In biochemistry, naturally occurring phenols are natural products containing at least one phenol functional group. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants.

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

Verbascoside is a caffeoyl phenylethanoid glycoside in which the phenylpropanoid caffeic acid and the phenylethanoid hydroxytyrosol form an ester and an ether bond respectively, to the rhamnose part of a disaccharide, namely β-(3′,4′-dihydroxyphenyl)ethyl-O-α-L-rhamnopyranosyl(1→3)-β-D-(4-O-caffeoyl)-glucopyranoside.

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

Echinacoside is a natural phenol. It is a caffeic acid glycoside from the phenylpropanoid class. It is constituted from a trisaccharide consisting of two glucose and one rhamnose moieties glycosidically linked to one caffeic acid and one dihydroxyphenylethanol (hydroxytyrosol) residue at the centrally situated rhamnose. This water-soluble glycoside is a distinctive secondary metabolite of Echinacea angustifolia and Echinacea pallida but only occurs in trace amounts in Echinacea purpurea. It is also isolated from Cistanche spp.

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