The structure‐dependent self‐association of five phenolic acids in aqueous solution

Xiao, Chaoni; Wu, Man; Zhang, Yajun; Zhao, Xinfeng; Yu, Jie; Zheng, Xiaohui

doi:10.1002/mrc.4089

Cited by 8 publications

(5 citation statements)

References 29 publications

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“…Despite being small aromatic molecules, some of them should form aggregates in solution at high concentrations, corresponding to crystal nucleation. Such aggregation processes can be monitored by concentration-dependent 1 H NMR spectral shifts. − Furthermore, there have been attempts to construct small π-system-based supramolecular polymers by utilizing intermolecular hydrogen bonding and hydrophobic interactions. , However, they do not bring about significant absorption and fluorescence spectral changes as seen in the larger π-systems like cyanine and PBI dyes, since intermolecular π–π interactions are weak between such small aromatic molecules …”

Section: Introductionmentioning

confidence: 99%

Supramolecular Complexation and Collective Optical Properties Induced by Linking Two Methyl Salicylates via a σ-Bridge

et al. 2022

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Supramolecular complexes or polymers, formed by noncovalent intermolecular forces such as π–π and dipole–dipole interactions, have the potential to render collective optical properties brought about by excitons spreading over multiple molecules, as seen in J-aggregates. In this respect, molecules with a large π-system and dipole moment are advantageous. However, we report here that methyl salicyate (MS) dyad-type molecules, synthesized by connection of two MSs via a σ-bridge, are effective for forming stable aggregates with collective optical properties. The self-association of MS-dyads occurs in a CHCl3 solution at a high concentration of over 10–2 M, which is recognized by the appearance of an absorption band (λmax = 464 nm) bathochromically shifted beyond 8300 cm–1 from the band in the dilute solution (λmax = 334 nm). Upon excitation of this band, an intense green fluorescence is observed without aggregation-caused quenching. The absorption and fluorescence bands, both of which have well-resolved vibronic progressions, are in a near-mirror image relationship, yielding a small Stokes shift of 600 cm–1. A reasonable explanation for these characteristic optical properties is provided from theoretical considerations on the aggregate model constructed based on the results of single-crystal X-ray analysis. The 1H NMR measurements suggest that unconnected MSs also form aggregates at high concentrations, although the absorption measurements do not provide any evidence for this. It is thus presumed that the connection of MSs stabilizes the MS stacking structure of the aggregates, leading to the generation of an excited state delocalized over multiple molecules.

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Section: Introductionmentioning

confidence: 99%

Supramolecular Complexation and Collective Optical Properties Induced by Linking Two Methyl Salicylates via a σ-Bridge

et al. 2022

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“…Due to the presence of ester bonds, the conformation of RosA, SalA-C, LSA and CY have a certain degree of flexibility. The structure of phenolic acids may change or degrade under the influence of pH and temperature, and structure-dependent self-association may occur in an aqueous solution [ 32 , 33 , 39 ]. Docking analysis suggests that these phenolic acids may have more than one possible configuration on the JAK ( Figure 4 ).…”

Section: Resultsmentioning

confidence: 99%

The Potential Role of Phenolic Acids from Salvia miltiorrhiza and Cynara scolymus and Their Derivatives as JAK Inhibitors: An In Silico Study

Liao

Tzen

2022

IJMS

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JAK inhibition is a new strategy for treating autoimmune and inflammatory diseases. Previous studies have shown the immunoregulatory and anti-inflammatory effects of Salvia miltiorrhiza and Cynara scolymus and suggest that the bioactivity of their phenolic acids involves the JAK-STAT pathway, but it is unclear whether these effects occur through JAK inhibition. The JAK binding affinities obtained by docking Rosmarinic acid (RosA), Salvianolic acid A (SalA), Salvianolic acid C (SalC), Lithospermic acid, Salvianolic acid B and Cynarin (CY) to JAK (PDB: 6DBN) with AutoDock Vina are −8.8, −9.8, −10.7, −10.0, −10.3 and −9.7 kcal/mol, respectively. Their predicted configurations enable hydrogen bonding with the hinge region and N- and C-terminal lobes of the JAK kinase domain. The benzofuran core of SalC, the compound with the greatest binding affinity, sits near Leu959, such as Tofacitinib’s pyrrolopyrimidine. A SalC derivative with a binding affinity of −12.2 kcal/mol was designed while maintaining this relationship. The docking results show follow-up studies of these phenolic acids as JAK inhibitors may be indicated. Furthermore, derivatives of SalC, RosA, CY and SalA can yield better binding affinity or bioavailability scores, indicating that their structures may be suitable as scaffolds for the design of new JAK inhibitors.

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“…Chemical shift of quantitative peaks upfielded slightly along with the degradation went on. Assignment of quantitative peaks also referred to Zhou et al’s [ 26 ] and Xiao et al’s works [ 36 ]. For ascertaining specificity of the quantitative peaks, 2D NMR (COSY and HSQC) were adopted, supporting the assignment of peaks used for the quantification.…”

Section: Resultsmentioning

confidence: 99%

Degradation Kinetics and Mechanism of Lithospermic Acid under Low Oxygen Condition Using Quantitative 1H NMR with HPLC-MS

Pan

Gong

2016

PLoS ONE

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A novel quantitative 1H NMR (Q-NMR) combined with HPLC-MS method has been proposed for investigating the degradation process of traditional Chinese medicine (TCM) components. Through this method, in-situ monitoring of dynamics degradation process of lithospermic acid (LA), one of the popular polyphenolic acids in TCM, was realized under low oxygen condition. Additionally, this methodology was proved to be simple, rapid and specific. Degradation kinetic runs have been carried out to systematically investigate the effects of two key environmental factors, initial pH values and temperatures. Eight main degradation products of LA were detected, seven of which were tentatively structural elucidated with the help of both NMR and LC-MS in this work and salvianolic acid A (Sal A) was the primary degradation product of LA. A possible degradation pathway of LA was proposed, subsequently. The results showed that the degradation of LA followed pseudo-first-order kinetics. The apparent degradation kinetic constants increased as the initial pH value of the phosphate buffer increased. Under the given conditions, the rate constants of overall degradation as a function of temperature obeyed the Arrhenius equation. Our results proved that the Q-NMR combined with HPLC-MS method can be one of the most promising techniques for investigating degradation process of active components in TCM.

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The structure‐dependent self‐association of five phenolic acids in aqueous solution

Cited by 8 publications

References 29 publications

Supramolecular Complexation and Collective Optical Properties Induced by Linking Two Methyl Salicylates via a σ-Bridge

Supramolecular Complexation and Collective Optical Properties Induced by Linking Two Methyl Salicylates via a σ-Bridge

The Potential Role of Phenolic Acids from Salvia miltiorrhiza and Cynara scolymus and Their Derivatives as JAK Inhibitors: An In Silico Study

Degradation Kinetics and Mechanism of Lithospermic Acid under Low Oxygen Condition Using Quantitative 1H NMR with HPLC-MS

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