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Triterpenoid saponins from corms of Crocus sativus: Localization, extraction and characterization |
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| Authors: | Ángela Rubio-Moraga Gerrit J Gerwig Maria Luisa Jimeno José-Antonio Fernández Johannis P Kamerling |
| Institution: | a Biotechnology Group, Institute for Regional Development (IDR), University of Castilla-La Mancha, Campus Universitario s/n, 02071 Albacete, Spain b Bijvoet Center, Department of Bio-Organic Chemistry, Utrecht University, Kruytgebouw Padualaan 8, NL 3584 CH Utrecht, The Netherlands c Centro Química Orgánica “Lora Tamayo” (CSIC), Juan de la Cierva, 3, Madrid 28006, Spain |
| Abstract: | A mixture of highly glycosilated triterpenoid saponins (CS5) isolated from the corm of Crocus sativus or saffron showed cytotoxic activity against HeLa tumoral cells. The main reverse phase HPLC fraction of this mixture (CS5-1) contains two new oleanane-type saponins, denominated Azafrine 1 (1) and Azafrine 2 (2). The bidesmosidic saponins were respectively characterized as (1) 3-O-β-d-glucopyranosiduronic acid echinocystic acid 28-O-β-D-galactopyranosyl-(1 → 2)-α-l-arabinopyranosyl-(1 → 2)-β-d-xylopyranosyl-(1 → 4)]-α-d-rhamnopyranosyl-(1 → 2)-4-O-di-α-L-rhamnopyranosyl-3,16-dihydroxy-10-oxo-hexadecanoyl]-α-D-fucopyranoside and (2) 3-O-β-D-galactopyranosiduronic acid echinocystic acid 28-O-β-D-galactopyranosyl-(1 → 2)-α-L-arabinopyranosyl-(1 → 2)-β-D-xylopyranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-4-O-di-α-L-rhamnopyranosyl-3,16-dihydroxy-10-oxo-hexadecanoyl]-β-D-fucopyranoside. The surfactant properties of saponins, probably involved in the cytotoxic activity of CS5 and their exclusive localization in the external part or the corm, indicate their possible role as phytoprotectans. The similarity of their structural compositions to that of other triterpenoid saponins which are of special use in the pharmaceutical industry suggest a new application for C. sativus crops through the exploitation of corm for saponin extraction. |
| Keywords: | Crocus sativus Saffron Corms Saponins Triterpenoids Galacturonic acid |
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