Michelle Wiebel, Kathrin Bensberg, Luca Wende, Rebecca Grandrath, Kathrin Plitzko, Claudia Bohrmann-Linde, Stefan F. Kirsch and Nils Helge Schebb*,
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引用次数: 0
摘要
三萜酸(TA)是一类三萜类化合物,广泛分布于植物中的次级代谢产物。它们具有五环结构,并显示出高度的结构多样性。本研究介绍了一种从苹果皮中提取和检测 TA 衍生物的简单而高效的方法。该方法技术简单、稳健,可在本科生实验室、科学课或学校项目中实施:苹果皮(i)用乙酸乙酯提取,(ii)用环己烷脱脂,(iii)在乙醇中重组。提取物的产量约为 2.1 克/100 克苹果皮干重,其中 TA 占 70%(熊果酸(UA)56%,齐墩果酸(OA)10%)。用 KMnO4 溶液进行简单检测,即可通过薄层色谱法(TLC)对 TA 模式进行评估。通过在正相 TLC 板上分离不同的 TA 衍生物,可以了解化学结构对色谱分离的影响。整个过程需要 3-4 小时,不包括干燥步骤。TA 萃取是学生学习和讨论天然产品和植物次生代谢物的合适内容。通过这种方法还可以学习萃取的性能、天然产品的纯化以及色谱分离和检测的观察。使用这种简单的方法,可以从苹果皮中提取出高达 1 克/100 克干重的 UA。虽然实验中只使用了苹果皮,但其余的苹果果实都被学生们吃掉了。因此,该实验本身就展示了如何利用食品生产的副产品作为化合物的来源。
Efficient and Simple Extraction Protocol for Triterpenic Acids from Apples
Triterpenic acids (TA), a class of triterpenoids, are widely distributed as secondary metabolites in plants. They have a pentacyclic structure and show high structural diversity. In this work, a simple but efficient method for extraction and detection of TA derivatives from apple peels is described. The method is technically straightforward and robust and can be implemented in both undergraduate laboratories and science classes or projects in school: Apple peels are (i) extracted with ethyl acetate, (ii) degreased with cyclohexane, and (iii) reconstituted in ethanol. Yields of about 2.1 g of extract/100 g of dry weight apple peel were obtained, which consisted of >70% TA (56% ursolic acid (UA), 10% oleanolic acid (OA)). The TA pattern can be evaluated by thin layer chromatography (TLC) using simple detection with a KMnO4 solution. The separation of the different TA derivatives on normal phase TLC plates enables learning how the chemical structure affects the chromatographic separation. The whole procedure requires 3–4 h without the drying steps. The TA extraction represents suitable content for student education since they learn and discuss natural products and secondary plant metabolites. The performance of an extraction, purification of natural products, and observation of chromatographic separation and detection are also learned in this method. Using this simple procedure, up to 1 g/100 g of dry weight UA can be generated from apple peels. While only apple peel is used for the experiment, the rest of the apple fruit was eaten by the students. Thus, the experiment itself is a demonstration of how side streams of food production can be used as a source for chemical compounds.
期刊介绍:
The Journal of Chemical Education is the official journal of the Division of Chemical Education of the American Chemical Society, co-published with the American Chemical Society Publications Division. Launched in 1924, the Journal of Chemical Education is the world’s premier chemical education journal. The Journal publishes peer-reviewed articles and related information as a resource to those in the field of chemical education and to those institutions that serve them. JCE typically addresses chemical content, activities, laboratory experiments, instructional methods, and pedagogies. The Journal serves as a means of communication among people across the world who are interested in the teaching and learning of chemistry. This includes instructors of chemistry from middle school through graduate school, professional staff who support these teaching activities, as well as some scientists in commerce, industry, and government.