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https://read.qxmd.com/read/36976846/-in-vitro-hepatic-metabolism-of-the-natural-product-quebecol
#1
JOURNAL ARTICLE
Gabriel Bernardes, Ed S Krol
Quebecol (2,3,3-tri-(3-methoxy-4-hydroxyphenyl)-1-propanol) is a polyphenolic compound, which is formed during maple syrup production from Acer spp. Quebecol bears structural similarities to the chemotherapy drug tamoxifen, which has led to synthesis of structural analogues and investigations into their pharmacological properties, however there are no reports on the hepatic metabolism of quebecol.This interest in therapeutic properties spurred us to investigate the in vitro microsomal Phase I and II metabolism of quebecol...
March 28, 2023: Xenobiotica; the Fate of Foreign Compounds in Biological Systems
https://read.qxmd.com/read/35745702/antipsoriatic-potential-of-quebecol-and-its-derivatives
#2
JOURNAL ARTICLE
Corinne Bouchard, Alexe Grenier, Sébastien Cardinal, Sarah Bélanger, Normand Voyer, Roxane Pouliot
Psoriasis is a chronic inflammatory skin disease mainly characterized by the hyperproliferation and abnormal differentiation of the epidermal keratinocytes. An interesting phenolic compound, namely quebecol (2,3,3-tri-(3-methoxy-4-hydroxyphenyl)-1-propanol) (compound 1 , CPD1), was isolated from maple syrup in 2011 and was recently synthesized. Quebecol and its derivatives ethyl 2,3,3-tris(3-hydroxy-4-methoxyphenyl)propenoate (compound 2 , CPD2) and bis(4-hydroxy-3-methoxyphenyl)methane (compound 3 , CPD3) have shown antiproliferative and anti-inflammatory potential, making them promising candidates for the treatment of psoriasis...
May 26, 2022: Pharmaceutics
https://read.qxmd.com/read/35405614/a-world-tour-in-the-name-of-natural-products
#3
JOURNAL ARTICLE
Christian Bailly
BACKGROUND: Names of natural products (NP) are usually given depending on the species of origin, be it a plant, a marine organism or a microbial species. In some cases, names have been given with reference to people, animals, music, foods or places. Many NP refer to countries, cities or specific places such as mountains, deserts, seas and oceans. PURPOSE: On the basis of NP names, a world tour has been imagined referring to more than one hundred NP with names evocative of over 50 countries and regions...
March 27, 2022: Phytomedicine
https://read.qxmd.com/read/34722979/quebecol-shows-potential-to-alleviate-periodontal-tissue-damage-and-promote-bone-formation-in-in-vitro-models
#4
JOURNAL ARTICLE
Sébastien Cardinal, Amel Ben Lagha, Jabrane Azelmat, Daniel Grenier
Quebecol is a polyphenolic compound initially isolated from Canadian maple syrup in 2011. Recently, our group demonstrated in a macrophage model that quebecol inhibits the secretion of pro-inflammatory cytokines and reduces the activation of the NF-κB transcription factor. In this study, we further explored the therapeutic potential of quebecol against periodontal disease, an inflammatory disorder of bacterial origin affecting tooth-supporting tissues. More specifically, the effects of this natural compound on matrix metalloproteinase (MMP) activity and macrophage secretion, as well as on the mineralization activity of osteoblasts (bone-forming cells), were investigated...
October 26, 2021: ACS Omega
https://read.qxmd.com/read/34180070/chemistry-processing-and-functionality-of-maple-food-products-an-updated-comprehensive-review
#5
REVIEW
Mohamed Fawzy Ramadan, Haidy A Gad, Mohamed A Farag
Maple sap is a rich nutrient matrix collected from Acer trees to produce several food products (i.e., sap, water, extract, syrup, and sugar), of which syrup is the most famous in the food industry for its distinct taste and flavor. Maple syrup is produced from the sap of several species (Acer saccharum, Acer nigrum, and Acer rubrum) of maple. Maple syrup is chiefly produced through the concentration of sap via thermal evaporation (pan evaporation) or membrane separation. Each processing technique affects the quality and characteristics of processed maple products...
June 27, 2021: Journal of Food Biochemistry
https://read.qxmd.com/read/28258800/synthesis-and-anti-inflammatory-activity-of-isoquebecol
#6
JOURNAL ARTICLE
Sébastien Cardinal, Pierre-Alexandre Paquet-Côté, Jabrane Azelmat, Corinne Bouchard, Daniel Grenier, Normand Voyer
We report here the synthesis of isoquebecol, an unprecedented constitutional isomer of quebecol, a polyphenolic compound discovered in maple syrup. The methodology used to prepare isoquebecol involves, as key steps, the formation of a dibromoalkene from an α-ketoester precursor, followed by a double Suzuki-Miyaura reaction. The anti-inflammatory activity of isoquebecol was studied on macrophage cells by monitoring its ability to inhibit LPS-induced IL-6 secretion. Results show that this new compound has an improved bioactivity over that of its natural isomer...
April 1, 2017: Bioorganic & Medicinal Chemistry
https://read.qxmd.com/read/26691759/anti-inflammatory-properties-of-quebecol-and-its-derivatives
#7
JOURNAL ARTICLE
Sébastien Cardinal, Jabrane Azelmat, Daniel Grenier, Normand Voyer
Herein we report our results on the anti-inflammatory activity of quebecol, a polyphenolic compound discovered in maple syrup. Bioassays demonstrated that quebecol has an anti-inflammatory effect on LPS-induced NF-κB activation and inhibits the secretion of two pro-inflammatory cytokines, IL-6 and TNF-α. We also prepared and tested precursors of quebecol and its derivatives corresponding to its substructures of interest, with the aim to study the structure-activity relationships. Comparing the results obtained for all tested compounds allowed the identification of the main moiety responsible for the anti-inflammatory activity of quebecol...
January 15, 2016: Bioorganic & Medicinal Chemistry Letters
https://read.qxmd.com/read/23953195/synthesis-and-antiproliferative-activities-of-quebecol-and-its-analogs
#8
JOURNAL ARTICLE
Kasiviswanadharaju Pericherla, Amir Nasrolahi Shirazi, V Kameshwara Rao, Rakesh K Tiwari, Nicholas DaSilva, Kellen T McCaffrey, Yousef A Beni, Antonio González-Sarrías, Navindra P Seeram, Keykavous Parang, Anil Kumar
Simple and efficient synthesis of quebecol and a number of its analogs was accomplished in five steps. The synthesized compounds were evaluated for antiproliferative activities against human cervix adenocarcinoma (HeLa), human ovarian carcinoma (SK-OV-3), human colon carcinoma (HT-29), and human breast adenocarcinoma (MCF-7) cancer cell lines. Among all the compounds, 7c, 7d, 7f, and 8f exhibited antiproliferative activities against four tested cell lines with inhibition over 80% at 75 μM after 72 h, whereas, compound 7b and 7g were more selective towards MCF-7 cell line...
October 1, 2013: Bioorganic & Medicinal Chemistry Letters
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