Systematic evaluation of thymol derivatives possessing stereogenic or prostereogenic centers

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• 作者：Armando Talavera-Alemán ; Gabriela Rodríguez-García ; Yliana López…
• 关键词：Thymol ; Asteraceae ; 8 ; 9 ; Epoxythymol derivatives ; 8 ; 9 ; Dehydrothymol derivatives
• 刊名：Phytochemistry Reviews
• 出版年：2016
• 出版时间：April 2016
• 年：2016
• 卷：15
• 期：2
• 页码：251-277
• 全文大小：1,062 KB
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• 作者单位：Armando Talavera-Alemán (1)
  Gabriela Rodríguez-García (1)
  Yliana López (1)
  Hugo A. García-Gutiérrez (1)
  J. Martín Torres-Valencia (2)
  Rosa E. del Río (1)
  Carlos M. Cerda-García-Rojas (3)
  Pedro Joseph-Nathan (3)
  Mario A. Gómez-Hurtado (1)
  
  1. Instituto de Investigaciones Químico Biológicas, Universidad Michoacana de San Nicolás de Hidalgo, Ciudad Universitaria, 58030, Morelia, Michoacán, Mexico
  2. Área Académica de Química, Universidad Autónoma del Estado de Hidalgo, Km 4.5 Carretera Pachuca-Tulancingo, 42184, Mineral de la Reforma, Hidalgo, Mexico
  3. Departamento de Química, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Apartado 14-740, 07000, Mexico, D. F., Mexico
  
• 刊物类别：Biomedical and Life Sciences
• 刊物主题：Life Sciences
  Plant Sciences
  Biochemistry
  Organic Chemistry
  Chemistry
  
• 出版者：Springer Netherlands
• ISSN：1572-980X

文摘

Thymol (2-isopropyl-5-methylphenol) is an aromatic molecule typically distributed in the genera Thymus and Origanum, which possesses both pharmacological and industrial relevance. This review highlights thymol derivatives with a stereogenic or prostereogenic center, which are distributed in 42 genera of the Asteraceae family whose chemotaxonomy is also outlined. In order to achieve a systematic analysis, which includes a structural examination and accounts for the vegetal sources, the reviewed thymol derivatives were grouped into mono-, di-, and multisubstituted compounds. According to the substitution on the aromatic ring, as well as on the isopropyl residue, and considering the functional groups, an evaluation of the 1H NMR signals, including multiplicities, was carried out. Optical activity data compilation of thymol derivatives revealed that 21 molecules show no optical activity in spite of having a stereogenic center, while two groups of 16 and 15 compounds exhibit, respectively, levorotatory and dextrorotatory optical activity. In addition, two thymol derivatives showed different optical behavior depending on the vegetal source, and only in a single case, the absolute configuration of a thymol derivative is known. Some 10 % of the known functionalized thymol derivatives have been evaluated biologically as antibacterial, anti-inflammatory, antiprotozoal, antioxidant, cytotoxic, piscicidal or allelopathic agents, being the last biological activity the most assayed one.