title: Effective isolation protocol for secondary metabolites from saffron: semi-preparative scale preparation of crocin-1 and trans-crocetin.
abstract: Extracts from saffron, the dried stigmata from Crocus sativus L. are recognized as valuable tools for pharmaceutical development in neuroprotection and antidepressive therapy. One major lead compound is crocin-1 (1), which gets metabolized to the C20-dicarboxylic acid trans-crocetin (2) being responsible for potential NMDA-antagonistic effects in the central nervous system. Neither crocin-1 nor crocetin are commercially available in sufficient quality and to a reasonable price. The following protocol describes effective methods to obtain both compounds from an EtOH-water extract (2:8) in good yields (about 43% related to the starting material). Crocin-1 (purity>90%) can be obtained from the extract by means of partition chromatography (FCPC) in a single run without fractionation of the mobile phase by using only the stationary phase and in yields of about 48%, related to the saffron extract. Trans-crocetin can be obtained from the EtOH-water extract by enzymatic deglycosylation of crocins using commercially available cheap glycosidase mixtures as e.g. Röhm Enzyme® or RohamentCL®. Further polishing can be achieved by flash chromatography on MCI® stationary phase with yields between 6 and 11%. The protocols described provide effective isolation of crocin-1 and trans-crocetin reference compounds for further preclinical and analytical studies with saffron extracts.
authors: University of Münster, Institute of Pharmaceutical Biology and Phytochemistry, Corrensstr. 48, D-48149 Münster, Germany.
authors: Marcus
authors: M
authors: Lautenschläger
authors: University of Münster, Institute of Pharmaceutical Biology and Phytochemistry, Corrensstr. 48, D-48149 Münster, Germany.
authors: Matthias
authors: M
authors: Lechtenberg
authors: University of Münster, Institute of Pharmaceutical Biology and Phytochemistry, Corrensstr. 48, D-48149 Münster, Germany.
authors: Jandirk
authors: J
authors: Sendker
authors: University of Münster, Institute of Pharmaceutical Biology and Phytochemistry, Corrensstr. 48, D-48149 Münster, Germany. Electronic address: ahensel@uni-muenster.de.
authors: Andreas
authors: A
authors: Hensel
mesh_terms: D000928:Antidepressive Agents / Q000302:isolation & purification*; D002338:Carotenoids / Q000302:isolation & purification*; D027622:Crocus / Q000737:chemistry*; D035264:Flowers / Q000737:chemistry*; D018696:Neuroprotective Agents / Q000302:isolation & purification*; D008517:Phytotherapy; D010936:Plant Extracts / Q000737:chemistry*; D064210:Secondary Metabolism; D014801:Vitamin A / Q000031:analogs & derivatives
chemical_list: D000928:Antidepressive Agents; D018696:Neuroprotective Agents; D010936:Plant Extracts; C487773:trans-sodium crocetinate; D014801:Vitamin A; D002338:Carotenoids; C029036:crocin
keywords: Crocetin; Crocin; Crocus sativus L; Isolation