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Results for “Quinic Acid”

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At least 19 recordsLinked to original sources
PubMed2000

Thermodynamics of interaction of caffeic acid and quinic acid with multisubunit proteins.

Helianthinin is a multisubunit protein from Sunflower seeds. Caffeic acid (CA) and quinic acid (QA) are intrinsic ligands present in sunflower seeds. The mechanism of interaction of these ligands with multisubunit proteins is limited. The present study enables one to understand the mechanism of the interaction of these ligands with the protein helianthinin. From this study, it is shown that CA has two classes of binding sites on helianthinin. The high-affinity class of sites total six from 60+/-10 for both high-affinity and low-affinity sites. Tryptophan, tyrosine and lysine residues of the protein are mainly involved in the interaction with CA. The temperature dependence of the binding in the range 10-45 degrees C can be clearly described by an enthalpy-entropy compensation effect at the low-affinity class of sites, while it is described by positive DeltaC(p)(o) at the high-affinity class of sites. This positive DeltaC(p)(o) has a contribution to the protein stability. The binding strength of CA also has a positive cooperativity at higher protein concentration. QA has two classes of binding sites on the protein based on the strength of the interaction. The interaction of QA with the protein is predominantly described by positive DeltaC(p)(o) for both classes of affinity. This suggests predominance of ionic/hydrogen bonding in the interaction process. Differential scanning calorimetric measurements reveal that the binding of both CA and QA induces destabilisation of the subunit-subunit interaction. Human methaemoglobin (mHb) has two binding sites on the molecule for CA. Both CA and QA decrease the stability of mHb, as indicated by decreased T(m). This destabilisation is also accompanied by dissociation to the monomers with concomitant conformational changes.

2S Albumins, Plant↗
PubMedDate not supplied

Shikimic acid and quinic acid are not mutagenic in the Ames assay.

Shikimic acid, reported to cause tumors in mice, and its close structural analog, quinic acid, both ubiquitous constituents of higher plants, were found not be be mutagenic in the Ames assay when tested with and without the rat liver microsomal activation system.

Animals↗
PubMed2006

Vanillic acid glycoside and quinic acid derivatives from Gardeniae Fructus.

Bioassay-directed chromatographic fractionation of an ethyl acetate extract of Gardenia jasminoides (Gardeniae Fructus) afforded a new vanillic acid 4-O-beta-d-(6'-sinapoyl)glucopyranoside (1) and five new quinic acid derivatives, methyl 5-O-caffeoyl-3-O-sinapoylquinate (2), ethyl 5-O-caffeoyl-3-O-sinapoylquinate (3), methyl 5-O-caffeoyl-4-O-sinapoylquinate (4), ethyl 5-O-caffeoyl-4-O-sinapoylquinate (5), and methyl 3,5-di-O-caffeoyl-4-O-(3-hydroxy-3-methyl)glutaroylquinate (6), together with three known quinic acid derivatives, two flavonoids, two iridoids, and two phenolic compounds. The structures of new compounds were elucidated by the aid of spectroscopic methods. These compounds were assessed for antioxidant activity using three different cell-free bioassay systems and for HIV-1 integrase inhibitory activity. Five new quinic acid derivatives showed potent DPPH radical scavenging, superoxide anion scavenging, and lipid peroxidation inhibition activities. These new quinic acid derivatives also exhibited HIV-1 integrase inhibitory activity.

Antioxidants↗
PubMed2001

Isolation from Cussonia barteri of 1'-O-chlorogenoylchlorogenic acid and 1'-O-chlorogenoylneochlorogenic acid, a new type of quinic acid esters.

1'-O-Chlorogenoylchlorogenic acid and 1'-O-chlorogenoylneochlorogenic acid, a new type of quinic acid esters, have been isolated, in addition to six known quinic acid esters, rutin, and a mixture of saponins, from the methanol extract of Cussonia barteri Seemann (Araliaceae) leaves collected in Cameroon. Structure determination was achieved by NMR, mass, IR, and UV spectroscopy. All compounds were tested for inhibitory activity on 5-lipoxygenase and cyclooxygenase-1, for antimicrobial activity against Bacillus subtilis, Pseudomonas fluorescens, and Cladosporium cucumerinum, and for haemolytic activity.

Anti-Infective Agents↗
PubMed1985

[Quinic acid lactone in coffee].

Quinic acid and its lactone (quinide) have been determined in coffee by capillary gas chromatography. No quinide could be detected in 14 green coffee's. After steaming of 4 green coffee's the content of quinic acid was always higher, but no quinide had been formed. During roasting, the latter can be detected when roasting loss exceed 6.5%. It increases approximately proportionally with quinic acid and amounts to 50% of the latter at 22% roasting loss. Both constituents decrease at unusual high roasting loss. In 13 commercial blends of roast coffee 2.4-6.4 g/kg quinide and 8.7-16.6 g/kg quinic acid were present. Especially high values were found in one Espresso type blend and high values in steamed and decaffeinated coffee's. In 11 commercial coffee extracts 2.0-23.2 g/kg quinide and 24.6-36.4 g/kg quinic acid were determined. At higher extraction yield, more quinic acid and quinide is formed, but at very high extraction yield the content of quinide is diminished. During holding of coffee brews at elevated temperature, quinide is slowly hydrolysed.

Chromatography, Gas↗
PubMed2004

Deodorization with ku-ding-cha containing a large amount of caffeoyl quinic acid derivatives.

Caffeoyl quinic acid (CQA) derivatives in ku-ding-cha, mate, coffee, and related plants were determined by HPLC. One ku-ding-cha contained a large amount of 3,5-dicaffeoylquinic acid (3,5-diCQA, 10.6% in dry weight) as well as 3-CQA (1.7%), 4-CQA (1.1%), 5-CQA (6.3%), 3,4-diCQA (1.8%), and 4,5-diCQA (4.3%). In this ku-ding-cha, the total caffeic acid moiety was 90.3 mmol/100 g of dry weight. The leaves of Ilex latifolia, which is one original species of ku-ding-cha, and another plant of the same genus, I. rotunda, also contained 3,5-diCQA (9.5 and 14.6%), 3-CQA (4.3 and 1.9%), and 5-CQA (4.8 and 3.8%), respectively, whereas raw coffee bean contained 5.5% 5-CQA and other low CQA derivatives. 3,5-DiCQA and 5-CQA with an apple acetone powder (AP) containing polyphenol oxidase showed high capturing activities toward thiols, and two addition compounds between 3,5-diCQA and methane thiol were also identified. Ku-ding-cha indicated extremely strong capturing activities toward methanethiol, propanethiol, and 2-propenethiol in the presence of apple AP. Furthermore, drinking ku-ding-cha reduced the amount of allyl methyl sulfide gas, well-known to persist as malodorous breath long after the ingestion of garlic.

Allyl Compounds↗
PubMed2005

Sialyl Lewis(x) analogs based on a quinic acid scaffold as the fucose mimic.

(-)-Quinic acid was used as a starting material for the preparation of sialyl Lewis(x) mimetics in order to target E-selectin. Spatial orientation of the hydroxyl groups of quinic acid could mimic the l-fucose ones. Introduction of a side chain ending with a carboxylic acid was effected to replace the sialic acid interaction at the carbohydrate recognition domain. A first series of derivatives, incorporating amino acids linked to quinic acid, were tested for their affinity and found to interact with E-selectin with IC(50) within the millimolar range.

Cell Adhesion↗
PubMedDate not supplied

Distribution of quinic acid derivatives and other phenolic compounds in Brazilian propolis.

The quinic acid derivatives (including 4-feruoyl quinic and 5-ferruoyl quinic acids characterized for first time in propolis samples) and other phenolic compounds were quantified in thirteen Brazilian propolis samples by HPLC analysis. For chemometrical analysis, the distribution of quinic acid derivatives and other phenolic compounds were considered. The results suggest that the Brazilian propolis with floral origin from Citrus sp. have the highest concentration of the quinic acid derivatives (between 11.0 to 58.4 mg/mg of the dried crude hydroalcoholic extract) and therefore would probably show a more effective hepatoprotective activity.

Brazil↗
PubMed1970

Species differences in the aromatization of quinic acid in vivo and the role of gut bacteria.

1. The fate of (-)-quinic acid has been investigated in 22 species of animals including man. 2. In man and three species of Old World monkeys, i.e. rhesus monkey, baboon and green monkey, oral quinic acid was extensively aromatized (20-60%) and excreted in the urine as hippuric acid, which was determined fluorimetrically. 3. In three species of New World monkeys, i.e. squirrel monkey, spider monkey and capuchin, in three species of lemurs, i.e. bushbaby, slow loris and tree shrew, in the dog, cat, ferret, rabbit, rat, mouse, guinea pig, hamster, lemming, fruit bat, hedgehog and pigeon, oral quinic acid was not extensively aromatized (0-5%). 4. In the rhesus monkey, injected quinic acid was not aromatized, but largely excreted unchanged. 5. In rhesus monkeys pretreated with neomycin to suppress gut flora, the aromatization of oral quinic acid was considerably suppressed. 6. In rats and rhesus monkeys [(14)C]quinic acid was used and this confirmed its low aromatization in rats and its high aromatization in the monkeys. 7. Shikimic acid given orally was excreted as hippuric acid (26-56%) in rhesus monkeys, but not in rats. 8. The results support the view that quinic acid and shikimic acid are aromatized by the gut flora in man and the Old World monkeys.

Animals↗