Uv–vis. Spectroscopic Characteristics of Ferulic Acid and Related Compounds

Pan, George X.; Thomson, Cameron I.; Leary, Gordon

doi:10.1081/wct-120013358

Cited by 27 publications

(10 citation statements)

References 18 publications

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“…Such a shoulder is consistent with π-π interactions of the aromatic ferulate group. 30 Raman spectroscopy also shows that as the gel concentration is increased, there are several changes in the vibrational spectra. The spectrum for a 5 % gel includes no features which are not also present for the two individual components.…”

Section: Scheme 2 Chemical Structures Of Phytosterols Used In Dockinmentioning

confidence: 99%

Molecular Interactions behind the Self-Assembly and Microstructure of Mixed Sterol Organogels

et al. 2018

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In this work, we have employed docking and atomistic molecular dynamics (MD) simulations supported by complementary experiments using atomic force microscopy, rheology, and spectroscopy to investigate the self-assembled structure of β-sitosterol and γ-oryzanol molecules into cylindrical tubules in a nonaqueous solvent. Docking models of several phytosterols, including sitosterol, with oryzanol and other sterol esters demonstrate that for systems to form tubules, the phytosterol sterane group must be stacked in a wedge shape with the ester sterane group and a hydrogen bond must form between the hydroxyl group of the phytosterol and the carbonyl group of the ester. MD of the self-assembled structure were initiated with the molecules in a roughly cylindrical configuration, as suggested from previous experimental studies, and the configurations were found to be stable during 50 ns simulations. We performed MD simulations of two tubules in proximity to better understand the aggregation of these fibrils and how the fibrils interact in order to stick together. We found that an interfibril network of noncovalent bonds, in particular van der Waals and π-π contacts, which is formed between the ferulic acid groups of oryzanol through the hydroxyl, methoxy, and aromatic groups, is responsible for the surface-to-surface interactions between fibrils; an observation supported by molecular spectroscopy. We believe that these interactions are of primary importance in creating a strong organogel network.

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Section: Scheme 2 Chemical Structures Of Phytosterols Used In Dockinmentioning

confidence: 99%

Molecular Interactions behind the Self-Assembly and Microstructure of Mixed Sterol Organogels

et al. 2018

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“…6. Pan et al [16] studied the UV-vis absorption spectroscopy of ferulic acid and ethyl ferulate in 50% aqueous 2-methoxy ethanol and observed a red shift from 310 to 325 nm. Ferulic acid is characterized by k max at 320 nm while soyamide based ferulate exhibits k max at 327 nm corresponding to a molar extinction coefficient of 19,705 L mol -1 cm -1 .…”

Section: Soyamide Ferulate Synthesismentioning

confidence: 99%

Synthesis and Characterization of Soyamide Ferulate

Rawlins

Pramanik

Mendon

2008

J Americ Oil Chem Soc

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Ferulic acid (4-hydroxy-3-methoxycinnamic acid) is a phytochemical antioxidant that is widely distributed throughout the plant kingdom. Cinnamic acid derivatives are used as biobased ultraviolet (UV) absorbers in sunscreen formulations. Soybean oil ferulate, a biobased UV absorber, was synthesized by reacting soyamide with ferulic acid. The resulting product was characterized by infrared (IR) and nuclear magnetic resonance (NMR) spectroscopy, and gel permeation chromatography (GPC). Spectroscopic studies measured the soyamide-based ferulate maximum absorbance at 327 nm with a molar extinction coefficient of 19,705 L mol -1 cm -1 . Soyamide ferulate has potential to be used in coatings.

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“…The advantage is that it can eliminate residual radiation where it would be most harmful. To eliminate excess and secondary produced ROS, for example from the metabolism, inflammatory reactions or high energy visible light, rosemary extract, especially carnosic acid and carnosine efficiently eliminate reactive oxygen species [33]. Interestingly, the combination of the ingredients of the active ingredient is able to stabilize the expression of 8‐oxo guanidine glycosylase after UV‐B impact in keratinocytes, facilitating repair of oxidatively damaged DNA and recover faster from circadian phase shift.…”

Section: Resultsmentioning

confidence: 99%

Influence of cosmetic formulations on the skin's circadian clock

Hettwer¹,

Gyenge²,

Obermayer³

2020

Intern J of Cosmetic Sci

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The circadian rhythm was set into focus by awarding the Nobel Price of Physiology/Medicine to Jeffrey Hall, Michael Rosbash and Michael Young in late 2017. Numerous publications elucidated the molecular mechanisms driving the circadian biorhythms of our body, peripheral organs and each single cell. However, there is minor knowledge on the circadian rhythm of the skin, which has its own peripheral circadian clock in contact with cosmetic formulations. The skin's epidermal clock is excessively influenced by environmental factors like UV radiation or modern lifestyle, which may induce epidermal jetlag. Here, we give an overview on the current knowledge about the epidermal circadian clock and provide a cosmetic solution to protect and preserve the biorhythm of the skin. METHODS: Quantitative RT-PCR to analyse the gene expression of circadian clock genes and the downstream DNA repair gene OGG1 in keratinocytes irradiated with UV-B. In vivo study to determine skin parameters dependent on the circadian cycle and interference of cosmetic formulations to them by assessment of morning and evening values at each measurement day after 28, 56 and 84 days of the study. RESULTS: UV-B irradiation leads to a pronounced delay in circadian clock and downstream gene expression which interferes in the proper function of epidermal stem cells and as thus skin function. The use of a cosmetic active ingredient prevents cyclobutane pyrimidine dimer formation, protects epidermal stem cells and resets the circadian gene expression. It preserves the circadian changes in skin hydration, reduces daily fluctuations of skin redness and strengthens the skin barrier. CONCLUSION: The skin has its own circadian biorhythm to gain full functionality. Interruption of this oscillation will lead to functional impairments. Here we show a cosmetic solution to protect and preserve the skin's circadian rhythm. DNA protection, ROS elimination and stimulation of circadian gene expression seem to be crucial to keep the skin in balance. CONCLUSION: La peau a son propre biorythme circadien pour acqu erir une assurer une parfaite fonctionnalit e. L'interruption de cette oscillation entraînera des troubles fonctionnels. Nous pr esentons ici une solution cosm etique pour prot eger et pr eserver le rythme circadien de la peau. La protection de l'ADN, l' elimination des ROS et la stimulation de l'expression des g enes circadiens semblentêtre cruciales pour maintenir l' equilibre de la peau.

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Uv–vis. Spectroscopic Characteristics of Ferulic Acid and Related Compounds

Cited by 27 publications

References 18 publications

Molecular Interactions behind the Self-Assembly and Microstructure of Mixed Sterol Organogels

Molecular Interactions behind the Self-Assembly and Microstructure of Mixed Sterol Organogels

Synthesis and Characterization of Soyamide Ferulate

Influence of cosmetic formulations on the skin's circadian clock

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