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Novel Piperidine and 3,4-dihydro-2H-pyrrole Alkaloids from Tilia platyphyllos and Tilia cordata Flowers
Planta Medica ( IF 2.1 ) Pub Date : 2021-01-12 , DOI: 10.1055/a-1340-0099
Nico Symma 1 , Marek Bütergerds 1 , Jandirk Sendker 1 , Frank Petereit 1 , Alexander Hake 1 , Martina Düfer 2 , Andreas Hensel 1
Affiliation  

Lime flowers, traditionally used for medical purposes for the treatment of symptoms of the common cold and mental stress, consist of the dried inflorescences including the floral bracts of Tilia cordata, Tilia platyphyllos, Tilia × vulgaris, or mixtures thereof. During phytochemical investigations, 6 different alkaloids - not described until now - were detected in T. cordata and T. platyphyllos flowers. They have been isolated and characterized as alkaloids with a dihydro-pyrrole and a piperidine substructure, respectively. Compounds 1A: and 1B: (tiliines A and B) are characterized as 2 diastereomers containing a 2-methyl-3,4-dihydro-2H-pyrrol-3-ol, connected via a C-10 alkyl chain to a O-glucosylated hydroquinone moiety. Compounds 2A: and 2B: (tiliamines A and B) are diastereomers of a 2-methyl-substituted piperidin-3-ol, coupled via a C-9 alkyl chain again to an O-glucosylated hydroquinone moiety. Compounds 3A: and 3B: (tilacetines A and B) are 3-O-acetylated derivatives of tiliamines. Quantification of the 6 alkaloids by HPLC-ESI-qTOF analysis indicated the presence of all alkaloids in T. cordata flowers and T. platyphyllos flowers, bracts, and leaves, with tiliines A and B and tilacetines A and B being the major compounds. Acetone/water turned out be the best extraction solvent for the alkaloids, but ethanol and ethanol/water mixtures also can be used for effective extraction. Furthermore, the alkaloids are found in hot water extracts, which are typically used in the traditional medicine.

中文翻译:

来自椴树和紫椴花的新型哌啶和 3,4-二氢-2H-吡咯生物碱

石灰花,传统上用于治疗普通感冒和精神压力症状的医学目的,由干燥的花序组成,包括 Tilia cordata、Tilia platyphyllos、Tilia × vulgaris 或其混合物的花苞。在植物化学研究期间,在 T. cordata 和 T. platyphyllos 花中检测到 6 种不同的生物碱 - 直到现在才被描述。它们已被分离并表征为分别具有二氢吡咯和哌啶亚结构的生物碱。化合物 1A: 和 1B: (tiliines A 和 B) 被表征为包含 2-methyl-3,4-dihydro-2H-pyrrol-3-ol 的 2 个非对映异构体,通过 C-10 烷基链连接到 O-葡萄糖基化氢醌部分。化合物 2A: 和 2B: (硫胺 A 和 B) 是 2-甲基取代的哌啶-3-醇的非对映异构体,通过 C-9 烷基链再次与 O-葡萄糖基化氢醌部分偶联。化合物3A:和3B:(替拉西汀A和B)是替拉胺的3-O-乙酰化衍生物。通过 HPLC-ESI-qTOF 分析对 6 种生物碱进行定量表明,所有生物碱均存在于 T. cordata 花和 T. platyphyllos 花、苞片和叶中,其中主要化合物为 tilines A 和 B 以及 tilacetines A 和 B。丙酮/水是生物碱的最佳提取溶剂,但乙醇和乙醇/水混合物也可用于有效提取。此外,生物碱存在于热水提取物中,通常用于传统药物。通过 HPLC-ESI-qTOF 分析对 6 种生物碱进行定量表明,所有生物碱均存在于 T. cordata 花和 T. platyphyllos 花、苞片和叶中,其中主要化合物为 tilines A 和 B 以及 tilacetines A 和 B。丙酮/水是生物碱的最佳提取溶剂,但乙醇和乙醇/水混合物也可用于有效提取。此外,生物碱存在于热水提取物中,通常用于传统药物。通过 HPLC-ESI-qTOF 分析对 6 种生物碱进行定量表明,所有生物碱均存在于 T. cordata 花和 T. platyphyllos 花、苞片和叶中,其中主要化合物为 tilines A 和 B 以及 tilacetines A 和 B。丙酮/水是生物碱的最佳提取溶剂,但乙醇和乙醇/水混合物也可用于有效提取。此外,生物碱存在于热水提取物中,通常用于传统药物。但乙醇和乙醇/水混合物也可用于有效提取。此外,生物碱存在于热水提取物中,通常用于传统药物。但乙醇和乙醇/水混合物也可用于有效提取。此外,生物碱存在于热水提取物中,通常用于传统药物。
更新日期:2021-01-12
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