Oleanane-type triterpene saponins from Calendula stellata

Meryem Lehbili 1, 2 Abdulmagid Alabdul Magid 2 Ahmed Kabouche 1 Laurence Voutquenne-Nazabadioko 2 Amin Abedini 2, 3 Hamid Morjani 4 Thomas Sarazin 4 Sophie Gangloff 3 Zahia Kabouche 1
1 UMC - Université Mentouri Constantine [Algérie]
2 ICMR - Institut de Chimie Moléculaire de Reims - UMR 7312
3 BIOS - Biomatériaux et inflammation en site osseux - EA 4691
4 MEDyC - Matrice extracellulaire et dynamique cellulaire - UMR 7369
Abstract : Five previously undescribed bisdesmosidic triterpenoid saponins named calendustellatosides A-E, along with fifteen known compounds were isolated from the 70% ethanol whole plant extract of Calendula stellata Cav. (Asteraceae). Their structures were determined by 1D- and 2D-NMR spectroscopy as well as high resolution mass spectrometry and acid hydrolysis. The saponins comprised oleanolic acid, echinocystic acid, morolic acid or mesembryanthemoidigenic acid as the aglycones and saccharide moieties at C-3 and C-28. Like most Calendula saponins, the sugar moiety linked at C-3 was either β-d-glucose or β-d-glucuronic acid which could be substituted at C-3 by a β-d-galactose and/or C-2 by a supplementary β-d-galactose or a β-d-glucose. The sugar moiety linked to C-28 was determined as β-d-glucose. The antibacterial evaluation of compounds 1–20 by bioautography on Staphylococcus aureus followed by the determination of MIC values of active compounds by serial dilution technique against 5 bacteria revealed that; calendustellatoside D was the most active against Enterococcus faecalis with an antibacterial effect comparable to antibiotics. The cytotoxic activities of isolated compounds were evaluated against fibrosarcoma cell line (HT1080) and human lung cancer cell line (A549). Calendustellatosides B and D exhibited a low cytotoxic activity against HT1080 cell line with IC50 values of 47 ± 0.6 and 39 ± 0.5 μM, respectively.
Keywords : Calendula stellata Asteraceae Triterpenoid saponins Flavonoids Antibacterial activity Cytotoxic activity
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Journal articles
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https://hal.univ-reims.fr/hal-01834101
Contributor : Abdulmagid Alabdul Magid <>
Submitted on : Tuesday, July 10, 2018 - 11:22:50 AM
Last modification on : Wednesday, December 18, 2019 - 1:30:37 AM

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Meryem Lehbili, Abdulmagid Alabdul Magid, Ahmed Kabouche, Laurence Voutquenne-Nazabadioko, Amin Abedini, et al.. Oleanane-type triterpene saponins from Calendula stellata. Phytochemistry, Elsevier, 2017, 144, pp.33 - 42. ⟨10.1016/j.phytochem.2017.08.015⟩. ⟨hal-01834101⟩

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