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HPLC of Thiophenes for Phytochemical and Biochemical Research

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Part of the book series: Modern Methods of Plant Analysis ((MOLMETHPLANT,volume 5))

Abstract

Thiophene derivatives are known from either synthetic or natural sources. Their occurrence in the Asteraceae family and in certain fungi is well documented (Bohlmann et al. 1973). They may be roughly classified by subdivision into mono-, di-, and terthiophenes; thiophene ring systems of naturally occurring compounds are usually connected at the 2,2′-positions. By substitution with various functional groups to thiophenes, a high diversity of chemical characters can be obtained; the most striking feature about natural thiophenes is the substitution with acetylenic side chains. For these reasons, most different chemical characteristics regarding solubility (polarity), distinct spectral properties as well as a remarkable instability (see below) of most of these compounds may be explained.

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References

  • Arnason T, Towers GHN, Philogene BJR, Lambert JDH (1983) The role of natural photo-sensitizers in plant resistance to insects. ACS Symp Ser 208: 139–151

    Article  CAS  Google Scholar 

  • Bohlmann F, Grenz M (1970) Neue Isopentenyl-acetophenon-Derivate aus Helianthella uniflora. Chem Ber 103: 90–95

    Article  CAS  Google Scholar 

  • Bohlmann F, Herbst P (1962) Über die Inhaltsstoffe von Tagetes-Arten. Chem Ber 95: 2945–2955

    Article  CAS  Google Scholar 

  • Bohlmann F, Zdero C (1979) Über dimere Terpenketone aus Tagetes gracilis. Phytochemistry (Oxf) 18: 341–343

    Article  CAS  Google Scholar 

  • Bohlmann F, Kleine KM, Arndt C (1964) Über natürlich vorkommende Thiophenacetylenverbindungen. Chem Ber 97: 2125–2134

    Article  CAS  Google Scholar 

  • Bohlmann F, Arndt C, Kleine KM, Bornowski H (1965) Die Acetylenverbindungen der Gattung Echinops. Chem Ber 98: 155–163

    Article  CAS  Google Scholar 

  • Bohlmann F, Burkhardt T, Zdero C (1973) Naturally occurring acetylenes. Academic Press, New York

    Google Scholar 

  • Downum KR, Towers GHN (1983) Analysis of thiophenes in the tageteae (asteraceae) by hplc. J Natl Prod 46: 98–103

    Article  CAS  Google Scholar 

  • Pensl R, Sütfeld R (1985) Occurrence of 3,4-diacetoxybutinylbithiophene in Tagetes patula and its enzymatic conversion. Z Naturforsch Sect C Biosci 40: 3–7

    Google Scholar 

  • Sørensen NA (1977) Polyacetylenes and conversation of chemical characters in the compositae. In: Heywood VH, Harborne JB, Turner BL (eds) Biology and chemistry of the compositae. Academic Press, London, pp 385–409

    Google Scholar 

  • Sütfeld R (1982) Distribution of thiophene derivatives in different organs of Tagetes patula seedlings grown under various conditions. Planta (Berl) 156: 536–440

    Article  Google Scholar 

  • Sütfeld R (1984) Phytochemische and enzymologische Untersuchungen zum Metabolismus von sekundären Naturstoffen in Tagetes-Keimlingen. Habilitation Thesis, Westf Wilh Univ, Münster

    Google Scholar 

  • Sütfeld R, Towers GHN (1982) 5-(4-Acetoxy-l-butinyl)-2,2′-bithiophene: acetate esterase from Tagetes patula. Phytochemistry (Oxf) 21: 277–279

    Article  Google Scholar 

  • Sütfeld R, Balza F, Towers GHN (1985) A new benzofuran from Tagetes seedlings. Phytochemistry (Oxf) 24: 876–877

    Article  Google Scholar 

  • Towers GHN (1980) Photosensitizers from plants and their photodynamic action. In: Reinhold L, Harborne JB, Swain T (eds) Prog Phytochem, vol 6. Pergamon, Oxford, pp 183–202

    Google Scholar 

  • Zechmeister L, Sease J (1947) A blue fluorescing compound, terthienyl, isolated from marigolds. J Am Chem Soc 69: 273

    Article  PubMed  CAS  Google Scholar 

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© 1987 Springer-Verlag Berlin Heidelberg

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Sütfeld, R. (1987). HPLC of Thiophenes for Phytochemical and Biochemical Research. In: Linskens, HF., Jackson, J.F. (eds) High Performance Liquid Chromatography in Plant Sciences. Modern Methods of Plant Analysis, vol 5. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-82951-2_7

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  • DOI: https://doi.org/10.1007/978-3-642-82951-2_7

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-82953-6

  • Online ISBN: 978-3-642-82951-2

  • eBook Packages: Springer Book Archive

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