Effective isolation protocol for secondary metabolites from Saffron: Semi-preparative scale preparation of crocin-1 and trans-crocetin
Effective isolation protocol for secondary metabolites from Saffron: Semi-preparative scale preparation of crocin-1 and trans-crocetin
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DOI：
10.1016/j.fitote.2013.11.014
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发表时间：
2014-01-01
期刊：
影响因子：
3.4
通讯作者：
Hensel, Andreas
中科院分区：
文献类型：
--
作者：
Lautenschlaeger, Marcus;Lechtenberg, Matthias;Hensel, Andreas
番红花的干燥柱头，番红花的提取物被认为是神经保护和抗抑郁治疗药物开发的有价值的工具。一种主要的先导化合物是藏红花素-1（1），其代谢为C-20-二羧酸加反式藏红花酸（2），负责中枢神经系统中的潜在NMDA拮抗作用。藏红花素-1和藏红花酸都不能以足够的质量和合理的价格商购获得。以下方案描述了从乙醇-水提取物（2：8）以良好收率（相对于起始材料约43%）获得两种化合物的有效方法。藏红花素-1（纯度> 90%）可以通过分配色谱法（FCPC）在单次运行中从提取物中获得，而无需通过仅使用固定相而分馏移动的相，并且产率为约48%（相对于藏红花提取物）。反式-藏红花酸可以从乙醇-水提取物中获得，通过使用市售的廉价糖苷酶混合物如RohmEnzyme（R）或RohamentCL（R）对藏红花进行酶促去糖基化。通过MCI（R）固定相上的快速色谱可以实现进一步的精制，产率在6%和11%之间。所描述的方案提供了藏红花素-1和反式藏红花酸参比化合物的有效分离，用于用藏红花提取物进行进一步的临床前和分析研究。(C)2013爱思唯尔有限公司版权所有。
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 C-20-dicarboxylic add 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. Rohm Enzyme (R) or RohamentCL (R). Further polishing can be achieved by flash chromatography on MCI (R) 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. (C) 2013 Elsevier B.V. All rights reserved.