Quinic acid esters of hydroxycinnamic acids in stone and pome fruit

The am ounts of free, conjugated (hydroxycinnamic acid amides) and insoluble (poly)amines (putrescine, spermidine, spermine) as well as hydroxycinnamic acid esters (quinic acid esters) were determined during development of male inflorescences of Corylus avellana L. The location of these compounds either in sporophytic or gametophytic tissues and the possible correlation of their accumulation with exine formation are discussed.

Download Full-text

Application of Chemometrics Tools to the Study of the Fe(III)–Tannic Acid Interaction

Frontiers in Chemistry ◽

10.3389/fchem.2020.614171 ◽

2020 ◽

Vol 8 ◽

Author(s):

Silvia Berto ◽

Eugenio Alladio

Keyword(s):

Tannic Acid ◽

Quinic Acid ◽

Multivariate Curve Resolution ◽

Concentration Profiles ◽

Data Treatment ◽

Chemical Models ◽

Parallel Factor ◽

The Stability ◽

Ph Range ◽

Acid Esters

Chemometric techniques were applied to the study of the interaction of iron(III) and tannic acid (TA). Modeling the interaction of Fe(III)–TA is a challenge, as can be the modeling of the metal complexation upon natural macromolecules without a well-defined molecular structure. The chemical formula for commercial TA is often given as C76H52O46, but in fact, it is a mixture of polygalloyl glucoses or polygalloyl quinic acid esters with the number of galloyl moieties per molecule ranging from 2 up to 12. Therefore, the data treatment cannot be based on just the stoichiometric approach. In this work, the redox behavior and the coordination capability of the TA toward Fe(III) were studied by UV-vis spectrophotometry and fluorescence spectroscopy. Multivariate Curve Resolution-Alternating Least Squares (MCR-ALS) and Parallel Factor Analysis (PARAFAC) were used for the data treatment, respectively. The pH range in which there is the redox stability of the system Fe(III)–TA was evaluated. The binding capability of TA toward Fe(III), the spectral features of coordination compounds, and the concentration profiles of the species in solution as a function of pH were defined. Moreover, the stability of the interaction between TA and Fe(III) was interpreted through the chemical models usually employed to depict the interaction of metal cations with humic substances and quantified using the concentration profiles estimated by MCR-ALS.

Download Full-text

Collagenase Inhibitory Quinic Acid Esters fromIpomoeapes-caprae

Journal of Natural Products ◽

10.1021/np0500631 ◽

2005 ◽

Vol 68 (5) ◽

pp. 794-796 ◽

Cited By ~ 28

Author(s):

Fumihiro Teramachi ◽

Takashi Koyano ◽

Thaworn Kowithayakorn ◽

Masahiko Hayashi ◽

Kanki Komiyama ◽

...

Keyword(s):

Quinic Acid ◽

Acid Esters

Download Full-text

Das Vorkommen von Glucosaminestern der Hydroxy-zimtsäuren in Gewebekulturen von Nicotiana tabacum

Zeitschrift für Naturforschung B ◽

10.1515/znb-1965-1223 ◽

1965 ◽

Vol 20 (12) ◽

pp. 1297-1301 ◽

Cited By ~ 6

Author(s):

L. Bergmann ◽

W. Thies ◽

K. Erdelsky

Keyword(s):

Phenolic Compounds ◽

Nicotiana Tabacum ◽

Ferulic Acid ◽

Spectral Data ◽

Phenolic Acid ◽

Hydroxycinnamic Acids ◽

Tissue Cultures ◽

Acid Esters

Tissue cultures of Nicotiana tabacum var. “Samsun” contain an array of phenolic compounds. Beside the known glucose and quinyl esters of the hydroxycinnamic acids three hitherto unreported phenolic acid esters were isolated from tobacco tissue cultures. The analytical and spectral data presented in this paper lead to the conclusion that these compounds are glucosamine esters of p-coumaric, caffeic, and ferulic acid.

Download Full-text

Agronomic and Metabolomic Side-Effects of a Divergent Selection for Indol-3-Ylmethylglucosinolate Content in Kale (Brassica oleracea var. acephala)

Metabolites ◽

10.3390/metabo11060384 ◽

2021 ◽

Vol 11 (6) ◽

pp. 384

Author(s):

Jorge Poveda ◽

Pablo Velasco ◽

Antonio de Haro ◽

Tor J. Johansen ◽

Alex C. McAlvay ◽

...

Keyword(s):

Brassica Oleracea ◽

Direct Evidence ◽

Quinic Acid ◽

Hydroxycinnamic Acids ◽

Coumaric Acid ◽

Flower Buds ◽

Cruciferous Vegetable ◽

Biotic Stresses ◽

Brassica Crops ◽

Selection For

Brassica oleracea var. acephala (kale) is a cruciferous vegetable widely cultivated for its leaves and flower buds in Europe and a food of global interest as a “superfood”. Brassica crops accumulate phytochemicals called glucosinolates (GSLs) which play an important role in plant defense against biotic stresses. Studies carried out to date suggest that GSLs may have a role in the adaptation of plants to different environments, but direct evidence is lacking. We grew two kale populations divergently selected for high and low indol-3-ylmethylGSL (IM) content (H-IM and L-IM, respectively) in different environments and analyzed agronomic parameters, GSL profiles and metabolomic profile. We found a significant increase in fresh and dry foliar weight in H-IM kale populations compared to L-IM in addition to a greater accumulation of total GSLs, indole GSLs and, specifically, IM and 1-methoxyindol-3-ylmethylGSL (1MeOIM). Metabolomic analysis revealed a significant different concentration of 44 metabolites in H-IM kale populations compared to L-IM. According to tentative peak identification from MS interpretation, 80% were phenolics, including flavonoids (kaempferol, quercetin and anthocyanin derivates, including acyl flavonoids), chlorogenic acids (esters of hydroxycinnamic acids and quinic acid), hydroxycinnamic acids (ferulic acid and p-coumaric acid) and coumarins. H-IM kale populations could be more tolerant to diverse environmental conditions, possibly due to GSLs and the associated metabolites with predicted antioxidant potential.

Download Full-text

Effects of hydroxycinnamic acid esters on sweetpotato weevil feeding and oviposition and interactions with Bacillus thuringiensis proteins

Journal of Pest Science ◽

10.1007/s10340-020-01297-5 ◽

2020 ◽

Author(s):

Milton O. Anyanga ◽

Dudley I. Farman ◽

Gorrettie N. Ssemakula ◽

Robert O. M. Mwanga ◽

Philip C. Stevenson

Keyword(s):

Host Plant ◽

Plant Resistance ◽

Host Plant Resistance ◽

Larval Mortality ◽

Hydroxycinnamic Acid ◽

Hydroxycinnamic Acids ◽

Sweetpotato Weevil ◽

Bt Protein ◽

Hydroxycinnamic Acid Esters ◽

Acid Esters

AbstractSweetpotato weevil (SPW) pest management is challenging because the pest target is sub-terranean, so the application of pesticides is impractical and usually ineffective. Host plant resistance and the genetic transformation of sweetpotatoes to produce entomotoxic Bt proteins offer potential for environmentally benign pest control. Resistance can be conferred by naturally occurring hydroxycinnamic acids which protect against oviposition by adults, but these compounds are restricted to the root surface so do not protect against the cortex bound larvae where the greatest damage occurs. Resistance could be enhanced if combined with expression of Bt proteins in transformed plants, but interactions between hydroxycinnamic acids and Bt proteins remain unknown. Here the bioactivity of Cry7Aa1 protein and hydroxycinnamic acid esters was evaluated individually and in combination against SPW larvae and mortality determined. Low and high concentrations of hydroxycinnamic acid esters alone caused significantly higher mortality of both weevil species in all experiments compared to the control. SPW larval mortality was greater when tested as a combination of hydroxycinnamic acid esters and Bt protein, but this effect was additive not synergistic. Although we report no evidence of antagonistic interactions, the antifeedant effects of the plant compounds conferring host plant resistance could have reduced consumption of the Bt protein in our assays leading to a lower efficacy when combined. Further work is required to determine whether the toxic effects of Bt proteins function alongside host plant resistance in sweetpotato under field conditions.

Download Full-text