Chicoric acid (dicaffeyltartic acid): Its isolation from chicory (Chicorium intybus) and synthesis

https://doi.org/10.1016/0040-4020(58)88005-9Get rights and content

Abstract

The isolation from the aqueous decoction of chicory leaves of a new optically active crystalline substance is described, for which the name chicoric acid is proposed. Experimental evidence indicates its structure as a caffeic diester of laevorotatory tartaric acid, which for the first time was found in nature in its (−)-form. Its synthesis, as well as that of laevorotatory and optically inactive isomers, was effected by the action of the chloride of carbonylcaffeic acid on d(−)-, l(+)- and meso-tartaric acids, respectively.

References (3)

  • M.L. Scarpati et al.

    Ann. Chim.

    (1957)
There are more references available in the full text version of this article.

Cited by (84)

  • In-solution structural studies involving a phospholipase A<inf>2</inf>-like myotoxin and a natural inhibitor: Plasticity of oligomeric assembly affects mechanisms of inhibition

    2021, Biochimie
    Citation Excerpt :

    However, PD values did not eliminate the possibility that monomers were present, which was similar to results of tests that directly assessed effects of buffer III. CA is a phenolic vegetal compound derivative of caffeic and tartaric acid, which was initially isolated from Cichorium intybus leaves [48]. After its discovery, this compound was identified within plants of 13 different orders (more frequently in Asteraceae species) [49], and has been associated with several types of therapeutic activities (reviewed in [32,49,50]).

  • Caffeic acid ester derivatives and flavonoids of genus Arnaldoa (Asteraceae, Barnadesioideae)

    2019, Biochemical Systematics and Ecology
    Citation Excerpt :

    The structures of the isolated compounds were established based on 1D and 2D-NMR spectroscopy, high-resolution MS and MS/MS analyses, and comparison with literature data. 2-O-Caffeoyltartaric acid (1) (Singleton et al., 1978), 5-O-caffeoylquinic acid (3) (Forino et al., 2015), caffeic acid (4) (Flamini et al., 2001), 2,3-O-dicaffeoyltartaric acid (9) (Scarpati and Oriente, 1958), quercetin-3-O-rutinoside (10) (Beck and Häberlein., 1999), quercetin-3-O-glucoside (11) (Manguro et al., 2003), and the putative quercetin-3-O-(6-O-malonyl)-glucoside (14) (Katsube et al., 2006) were isolated from A. weberbaueri. Additionally, 3-O-caffeoylquinic acid (2), 4-O-caffeoylquinic acid (5), 5-O-caffeoylquinic acid (3) (Pauli et al., 1998; Forino et al., 2015), 5-O-feruloylquinic acid (7), 3,4-O-dicaffeoylquinic acid (13), 1,5-O-dicaffeoylquinic acid (15), 3,5-O-dicaffeoylquinic acid (16), 4,5-O-dicaffeoylquinic acid (19) (Pauli et al., 1998, Pantoja Pulido et al., 2017), 4-O-caffeoyl-2-C-methyl-D-erythronic acid (8), 3-O-caffeoyl-2-(2-propyl)-2-hydroxybutanedioic acid (17), 3-O-caffeoyl-2-(2-butyl)-2-hydroxybutanedioic acid (20) (Ccana-Ccapatinta et al., 2017) and quercetin-3-O-glucoronide (12) (Bouktaib et al., 2002) were isolated from T. diversifolia.

  • Structural basis of phospholipase A<inf>2</inf>-like myotoxin inhibition by chicoric acid, a novel potent inhibitor of ophidian toxins

    2018, Biochimica et Biophysica Acta - General Subjects
    Citation Excerpt :

    The final crystallographic structure of the BthTX-I/CA complex was deposited in the Protein Data Bank under the code PDB ID: 6DIK. Chicoric acid (CA) is a phenolic vegetal compound derivative of caffeic and tartaric acid isolated initially from Cichorium intybus leaves [62]. After its discovery, this compound was found in 13 different plant orders, most often in Asteraceae species [63].

  • Identification of chicoric acid as a hypoglycemic agent from Ocimum gratissimum leaf extract in a biomonitoring in vivo study

    2014, Fitoterapia
    Citation Excerpt :

    Lamidey et al. (2002) reported a specific rotation of − 242.7° ([α]D22, c = 0.89, methanol) for l-chicoric acid, a value similar to that observed in our study [33]. Scarpati and Oriente (1958) however found a quite different value: − 384.2° ([α]D25, c = 1.075, methanol) using the same solvent employed by Lamidey et al. (2002) [34]. For l-caftaric acid, the reported [α]D20 is − 30.3° (c = 2, H2O) [35].

  • Sortase A inhibitory metabolites from the roots of Pulsatilla koreana

    2014, Bioorganic and Medicinal Chemistry Letters
View all citing articles on Scopus
View full text