(−)-Quinic acid: configurational (stereochemical) descriptors

Eliel, Ernest L.; Ramirez, Mara Bello

doi:10.1016/s0957-4166(97)00454-0

Cited by 41 publications

(59 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The presence of two peaks with m ∕ z 343 but different retention times can be explained by the presence of quinic acid and its isomer epiquinic acid (27) (28) (Eliwl & Ramirez, 1997). …”

Section: Resultsmentioning

confidence: 99%

Identification of phenolic secondary metabolites fromSchotia brachypetalaSond. (Fabaceae) and demonstration of their antioxidant activities inCaenorhabditis elegans

Sobeh

Elhawary

Peixoto

et al. 2016

PeerJ

View full text Add to dashboard Cite

BackgroundSchotia brachypetala Sond. (Fabaceae) is an endemic tree of Southern Africa whose phytochemistry and pharmacology were slightly studied. The present work aimed at profiling the major phenolics compounds present in the hydro-alcohol extract from S. brachypetala leaves (SBE) using LC/HRESI/MS/MS and NMR and prove their antioxidant capabilities using novel methods.MethodsIn vitro assays; DPPH, TEAC persulfate decolorizing kinetic and FRAP assays, and in vivo assays: Caenorhabditis elegans strains maintenance, Intracellular ROS in C. elegans, Survival assay, GFP expression and Subcellular DAF-16 localization were employed to evaluate the antioxidant activity.ResultsMore than forty polyphenols, including flavonoid glycosides, galloylated flavonoid glycosides, isoflavones, dihydrochalcones, procyanidins, anthocyanins, hydroxy benzoic acid derivatives, hydrolysable tannins, and traces of methylated and acetylated flavonoid derivatives were identified. Three compounds were isolated and identified from the genus Schotia for the first time, namely gallic acid, myricetin-3-O-α-L-1C4-rhamnoside and quercetin-3-O-L-1C4-rhamnoside. The total phenolics content of SBE was (376 mg CAE/g), followed by flavonoids (67.87 QE/g). In vitro antioxidant activity of SBE was evidenced by DPPH radical scavenging activity (IC50 of 9 µg/mL), FRAP ferric reducing activity (5,000 mol Fe2+ E/mg) and ABTS peroxide inhibiting activity (1,054 mM Trolox E/mg). The tested extract was able to protect the worms against juglone induced oxidative stress, an increased survival rate (up to 41%) was recorded, when compared with the control group (11%) and attenuate the reactive oxygen species (ROS) accumulation in dose-dependent and reached up to 72% for the highest tested concentration. SBE was also able to attenuate the levels of heat shock protein (HSP) expression in dose-dependent up to 60% in the 150 µg SBE/mL group. In DAF-16 Subcellular localization SBE treated worms showed nuclear localization pattern up to 78%, while it was only 5% in the untreated control group.DiscussionA pronounced antioxidant activity in vivo, which can be attributed to its ability to promote the nuclear translocation of DAF-16/FOXO, the main transcription factor regulating the expression of stress response genes. The remarkable antioxidant activity in vitro and in vivo correlates to SBE rich phenolic profile.

show abstract

“…The presence of two peaks with m ∕ z 343 but different retention times can be explained by the presence of quinic acid and its isomer epiquinic acid (27) (28) (Eliwl & Ramirez, 1997). …”

Section: Resultsmentioning

confidence: 99%

Identification of phenolic secondary metabolites fromSchotia brachypetalaSond. (Fabaceae) and demonstration of their antioxidant activities inCaenorhabditis elegans

Sobeh

Elhawary

Peixoto

et al. 2016

PeerJ

View full text Add to dashboard Cite

show abstract

“…1. In the IUPAC system (−)-quinic acid is defined as 1L-1(OH),3,4/5-tetrahydroxycyclohexane carboxylic acid, but Eliel and Ramirez (1997) recommend 1α,3R,4α,5R-tetrahydroxycyclohexane carboxylic acid. CGAs are widely distributed in plants (Clifford, 2000) but the coffee bean is remarkably rich in these compounds containing at least 72 chlorogenic acids that are not acylated at the C1 of the quinic acid moiety (Clifford, Johnston, Knight, & Kuhnert, 2003;.…”

Section: Introductionmentioning

confidence: 99%

Does roasted coffee contain chlorogenic acid lactones or/and cinnamoylshikimate esters?

Jaiswal

Matei

Subedi

et al. 2014

Food Research International

View full text Add to dashboard Cite

“…1. In the IUPAC system, used throughout this manuscript, (−) -quinic acid is defined as 1L-1(OH),3,4/5-tetrahydroxycyclohexane carboxylic acid but Eliel and Ramirez [8] recommend 1α,3R,4α,5R-tetrahydroxycyclohexane carboxylic acid. The CGAs show a variety of biological activities like antioxidant, anti-inflammatory, anti-HIV, anti-HBV, radical scavenging, inhibit mutagenesis and carcinogenesis and are considered to be beneficial to human health.…”

Section: Introductionmentioning

confidence: 99%

How to identify and discriminate between the methyl quinates of chlorogenic acids by liquid chromatography–tandem mass spectrometry

Jaiswal

Kuhnert

2011

J. Mass Spectrom.

View full text Add to dashboard Cite

The methyl esters of chlorogenic acids, methyl quinates, are widely distributed in plant materials and frequently appear as extraction artifacts in plant samples. This is the first time when liquid chromatography-tandem mass spectrometry methods have been used for the identification and characterization of the methyl quinates. For this purpose, methyl quinates of mono caffeoylquinic acids and mono feruloylquinic acids were synthesized as authentic standards. The methyl quinates of mono and diacyl chlorogenic acids have shown characteristic fragmentation pattern in their tandem mass spectra. MS(n + 1) spectra of the methyl quinates of diacyl chlorogenic acids were identical to MS(n) spectra of mono acyl derivatives. These quinates do not produce any methyl quinate peak at m/z 205 if compared with quinic acid peak at m/z 191 in negative ion mode. In the MS(n) spectra of these quinates, cinnamic acid part or cinnamoyl part was detected as a base peak in negative ion mode. The retention time, order of elution and fragmentation pattern were completely different if compared with LC-MS(n) methods developed for chlorogenic acids. These LC-MS(n) methods have been applied for the identification and regioisomeric characterization of the methyl quinates of chlorogenic acids in maté tea and woodruff (Galium odoratum). Two methyl caffeoylquinates (2 and 4) were identified as methyl 3-caffeoylquinate and methyl 5-caffeoylquinate.

show abstract

(−)-Quinic acid: configurational (stereochemical) descriptors

Cited by 41 publications

References 12 publications

Identification of phenolic secondary metabolites fromSchotia brachypetalaSond. (Fabaceae) and demonstration of their antioxidant activities inCaenorhabditis elegans

Identification of phenolic secondary metabolites fromSchotia brachypetalaSond. (Fabaceae) and demonstration of their antioxidant activities inCaenorhabditis elegans

Does roasted coffee contain chlorogenic acid lactones or/and cinnamoylshikimate esters?

How to identify and discriminate between the methyl quinates of chlorogenic acids by liquid chromatography–tandem mass spectrometry

Contact Info

Product

Resources

About