Valorization of saffron waste as a natural source of 3-hydroxy-γ-butyrolactone, a valuable chiral building block for pharmaceutical applications

M. Corti , S. Princiotto , M. Zuccolo , G. Beretta , S. Dallavalle , A. Pinto , F. Annunziata , G. Borgonovo
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Abstract

Saffron is the most expensive spice, appreciated in the best cuisine all over the world. However, its production is connected to the generation of a high volume of waste, i.e. stamens, leaves, tepals, spathes, corm, and tunics. Several biologically active compounds and high value chemical have been identified in the saffron biomass extracts, among which is found 3-hydroxy-γ-butyrolactone (3-HBL), a chiral building block involved in the production of different active pharmaceutical ingredients. The development of the first green and scalable extractive methodology for the isolation of 3-HBL from saffron tepals and stamen could be of great interest for different chemical sectors. After the selection of the best extractive medium (ethyl acetate) and the optimization of the operative procedure to a two-step protocol, microwave assisted extraction and accelerated solvent extraction were compared. The results showed a 3.6 ± 0.2 % vs 2.1 ± 0.1 % w/w recovery and could be exploitable not only on a lab scale but also for a possible industrial application. An enantiomeric excess of 14 % of the (S)-(−) isomer was found.

Abstract Image

藏红花是最昂贵的香料,在世界各地的顶级美食中都备受青睐。然而,藏红花的生产过程中会产生大量的废弃物,如雄蕊、叶片、花被片、花盘、花茎和鳞茎。在藏红花生物质提取物中发现了多种生物活性化合物和高价值化学物质,其中包括 3-羟基-γ-丁内酯(3-HBL),这是一种手性结构单元,可用于生产不同的活性药物成分。开发第一种从藏红花花被片和雄蕊中分离 3-HBL 的绿色、可扩展萃取方法,对不同的化学领域具有重大意义。在选择了最佳萃取介质(乙酸乙酯)并将操作程序优化为两步法后,对微波辅助萃取和加速溶剂萃取进行了比较。结果显示,两者的湿重回收率分别为 3.6 ± 0.2 % 和 2.1 ± 0.1 %,不仅可用于实验室规模,也可用于工业应用。发现(S)-(-)异构体的对映体过量率为 14%。
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