Published November 12, 2022 | Version v1
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NMR 800Hz characterization, mass spectrometry discussion and anti-proliferative effects of flavonoids, senecic acid and caffeic acid isolated from Senecio leucanthemifolius poiret growing in Morocco

Authors/Creators

  • 1. Hassan-II Institute of Agronomy and Veterinary Medicine (IAV), Madinat Al Irfane. BP 6202-Instituts, 10101-Rabat, Morocco.
  • 2. Laboratory of Electrochemistry and Analytical chemistry Faculty of Sciences, University Mohammed V-Agdal, Avenue Ibn Battouta 1014, Rabat, Morocco
  • 3. Institute of Natural Products Chemistry ICSN, CNRS 1.Avenue de la Terrasse 91190 Gf-sur- Yvette, France
  • 4. Laboratoire de Matrice Extracellulaire Dynamique Cellulaire, UMR CNRS 6237 Faculty of Pharmacy, Reims, France
  • 5. Laboratory of Organic Heterocyclic Chemistry, Faculty of Sciences, University Mohammed V-Agdal, Avenue Ibn Battouta 1014, Rabat, Morocco

Description

ABSTRACT

The present study consists at the chemical characterization, the structure elucidation and the in-vitro cytotoxic bioassay of some natural compounds isolated from Senecio leucanthemifolius poiret flowers growing in the Moroccan Western Middle Atlas mountains called Atlas of Beni- Mellal. The extraction by Soxhlet was carried out successively using the Ethyl Acetate and Methanol 90%. Each extract was fractionated using different chromatographic columns. The fractions and compounds obtained were purified by using HPLC semi-prevarative then analyzed by using HPLC, Mass Spectrometry (LC/MS; HRMS) and NMR 800Hz spectrometer. The isolated compounds were further subjected to antiprofliferative test on MCF7, HT1080, K562 and HL60 tumor cell lines. Four flavonoids were isolated and characterized: Isorhamnetin -3-O-β- glucose (7.0 mg) (Compound 1), Isorhamnetin, 3, 7-O- β-glucopyranoside (2.5 mg) (Compound 2); Quercitin-3-O- glucopyranoside (1.4mg) (Compound 3); Quercitin-7-O- β- glucopyranoside (1.2 mg) (Compound 4). Moreover, we could isolate one Caffeic acid (5.0 mg) (Compound 5) and two stereoisomers senecic acids (Compound 6) (Compound 7) respectively isolated with amounts of 1.4 mg and 1.0 mg. With the tested concentrations from 0.625 to 20 µM, compounds 1 and 2 highlighted a relative inhibition of the cell growth. However, compounds 5 and 6 showed a very moderate antiproliferative effect. These secondary metabolites are isolated and descripted for the first time from Senecio leucanthemifolius Poiret. According to the literature, it has been proved that there was no previous concerning their cytotoxic activity.

Keywords: Senecio, HRMS, NMR 800Hz , Flavonoids, cytotoxicy.

 

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