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伞形花内酯素作为蒿属植物植物化学物质库中的一种新成分

Umbelliprenin as a novel component of the phytochemical pool from Artemisia spp.

作者信息

Fiorito Serena, Genovese Salvatore, Palumbo Lucia, Scotti Luca, Ciulla Michele, di Profio Pietro, Epifano Francesco

机构信息

Dipartimento di Farmacia, Università "G. d'Annunzio" Chieti - Pescara, Via dei Vestini 31, 66100 Chieti Scalo, CH, Italy.

Dipartimento di Farmacia, Università "G. d'Annunzio" Chieti - Pescara, Via dei Vestini 31, 66100 Chieti Scalo, CH, Italy.

出版信息

J Pharm Biomed Anal. 2020 May 30;184:113205. doi: 10.1016/j.jpba.2020.113205. Epub 2020 Feb 24.

Abstract

Plants belonging to Artemisia spp. are known to biosynthesize a wide panel of 3,3-dimethylallyl- and sesquiterpenyl- substituted coumarins. In this short communication we applied a novel extraction methodology based on the use of subcritical butane under a counter-current mode to further characterize the presence of selected biologically active oxyprenylated phenylpropanoids, namely coumarins and ferulic acid derivatives, in extracts deriving from aerial parts of Artemisia vulgaris L. (commonly known as "common mugwort") (Asteraceae). In the mean time, we assessed the efficiency of the above mentioned extractive methodology with other routes like maceration and ultrasounds and microwaves-based methods using absolute EtOH as the solvents. UHPLC analysis coupled to UV/Vis detection revealed that, among the 5 pure chemical standard assayed, only umbelliprenin (7-farnesyloxycoumarin) was recorded, while boropinic acid, 4'-geranyloxyferulic acid, 7-isopentenyloxycoumarin, and auraptene were not detected. The best extractive yield (0.18 %) was obtained after extaction with subcritical butane. The presence of umbelliprenin in Artemisia plant species has been reported herein for the first time. This coumarin may represent the biosynthetic precursors of sesquiterpenyloxycoumarins with more complex structures typically found in this genus.

摘要

已知蒿属植物能生物合成多种3,3-二甲基烯丙基和倍半萜基取代的香豆素。在本简短通讯中,我们应用了一种基于逆流模式下使用亚临界丁烷的新型提取方法,以进一步表征从普通艾草(菊科)地上部分提取物中选定的具有生物活性的氧代异戊烯基化苯丙烷类化合物,即香豆素和阿魏酸衍生物的存在情况。同时,我们用其他方法评估了上述提取方法的效率,如浸渍法以及以无水乙醇为溶剂的基于超声和微波的方法。超高效液相色谱(UHPLC)分析结合紫外/可见检测显示,在所检测的5种纯化学标准品中,仅检测到伞形异戊烯基香豆素(7-法尼基氧基香豆素),而未检测到硼酸、4'-香叶氧基阿魏酸、7-异戊烯氧基香豆素和奥瑞潘。用亚临界丁烷提取后获得了最佳提取率(0.18%)。本文首次报道了艾草植物物种中存在伞形异戊烯基香豆素。这种香豆素可能是该属中通常发现的结构更复杂的倍半萜烯氧基香豆素的生物合成前体。

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