Abstract
The identification of secondary metabolites in lichens is a necessity for the correct determination of lichens in numerous groups, and the presence of substances is often mentioned in taxonomic keys. Numerous review papers have discussed the significance of secondary metabolites in lichen taxonomy (e.g., W Culberson 1969, 1970, 1986; WL Culberson and Culberson 1970; Hawksworth 1976; Brodo 1978, 1986; Leuckert 1985; CF Culberson 1986; Egan 1986; Rogers 1989; Lumbsch 1998a, b) and the chemistry of these substances (e.g., Asahina and Shibata 1954; Shibata 1963; Huneck 1968, 1971, 1973, 1984, 1991; Elix et al. 1984). Our knowledge of the biosynthesis of secondary metabolites in lichenized fungi has been summarised by (1969). The biological role of lichen substances was reviewed by (1986), and additional information regarding the ability of aromatic lichen substances to protect against irradiation can be found in (1995). Lichens may utilise secondary metabolites as chelating agents (Purvis et al. 1987), as inhibitors of lichenicolous fungi (Lawrey 1995), and to avoid saturation of the medulla by water (Armaleo 1993). Lists recording the distribution of secondary metabolites in different taxa have been compiled by Chicita Culberson and co-workers (CF Culberson 1969, 1970; CF Culberson et al. 1977). Some methods used in the identification of secondary metabolites in lichenized ascomycetes can be found in the literature cited below, but this chapter is restricted to examples of the two most commonly applied techniques, namely thin-layer chromatography (TLC), including high performance thin-layer chromatography (HPTLC) and high performance liquid chromatography (HPLC). Several publications deal with the identification of lichen substances, the most comprehensive being the recent book by Huneck and (1996). The reader is referred to this and the other publications for more detailed information and additional techniques used in lichen chemistry (Santesson 1973; Leuckert 1984; White and James 1985; CF Culberson and Elix 1989). Table 1 presents a list of the classes of secondary metabolites found in lichen-forming fungi.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Archer AW (1978) 3-Methyl-2-benzothiazolone hydrazone hydrochloride as a spray reagent for phenolic lichen compounds. J Chromatogr 152:290–292
Archer AW (1993) Identification of orcinol para-depsides in the lichen genus Pertusaria by thin layer chromatography. Mycotaxon 46:1–4
Armaleo D (1993) Why do lichens make secondary products? XV Int Bot Congr, Tokyo-Yokohama, Abstr, pp 11
Arup U, Ekman S, Lindblom L, Mattsson J-E (1993) High performance thin layer chromatography (HPTLC), an improved technique for screening lichen substances. Lichenologist 25:61–71
Asahina Y, Shibata S (1954) Chemistry of Lichen Substances. Jap Soc Prom Sci Tokyo
Brodo IM (1978) Changing concepts regarding chemical diversity in lichens. Lichenologist 10:1–11
Brodo IM (1986) Interpreting chemical variation in lichens for systematic purposes. Bryologist 89:132–138
Culberson CF (1969) Chemical and Botanical Guide to Lichen Products. Chapel Hill: Univ N Carolina Press
Culberson CF (1970) Supplement to Chemical and Botanical Guide to Lichen Products. Bryologist 73:177–377
Culberson CF (1972) Improved conditions and new data for the identification of lichen products by a standardized thin-layer Chromatographic method. J Chromatogr 72:113–125
Culberson CF (1986) Biogenetic relationships of the lichen substances in the framework of systematics. Bryologist 89:91–98
Culberson CF, Elix JA (1989) Lichen substances. In Harborne JB (ed): Methods in Plant Biochemistry Vol. 1. Plant Phenolics, pp 509–535. London, San Diego: Academic Press
Culberson CF, Johnson A (1976) A standardized two-dimensional thin-layer Chromatographie method for lichen products. J Chromatogr 128:253–259
Culberson CF, Kristinsson H (1970) A standardized method for the identification of lichen products. J Chromatogr 46:85–93
Culberson CF, Culberson WL, Johnson A (1977) Second Supplement to Chemical and Botanical Guide to Lichen Products. St. Louis: Am Bryol Lichenol Soc, Miss Bot Gard
Culberson CF, Culberson WL, Johnson A (1981) A standardized TLC analysis of ßorcinol depsidones. Bryologist 84:16–29
Culberson WL (1969) The use of chemistry in the systematics of the lichens. Taxon 18:152–166
Culberson WL (1970) Chemosystematics and ecology of lichen-forming fungi. Ann Rev Ecol Syst 1:153–170
Culberson WL (1986) Chemistry and sibling speciation in the lichen-forming fungi: ecological and biological considerations. Bryologist 89:123–131
Culberson WL, Culberson CF (1970) A phylogenetic view of chemical evolution in the lichens. Bryologist 73:1–31
Egan RS (1986) Correlations and non-correlations of chemical variation patterns with lichen morphology and geography. Bryologist 89:99–110
Elix JA, Whitton AA, Sargent MV (1984) Recent progress in the chemistry of lichen substances. Progr Chem Organ Nat Prod 45:103–234
Elix JA, Johnston J, Parker JL (1987) Mactabolites. Users Manual. 2nd edn. Canberra
Elix JA, Johnston J, Parker JL (1988) A computer program for the rapid identification of lichen substances. Mycotaxon 31:89–99
Esslinger TL (1994) On the chemistry and distribution of Cladonia petrophila. Mycotaxon 51:101–105
Feige GB, Lumbsch HT, Huneck S, Elix JA (1993) Identification of lichen substances by a standardized high-performance liquid Chromatographie method. J Chromatogr 646:417–427
Hanko B (1983) Die Chemotypen der Flechtengattung Vertusana in Europa. Bibl Lichenol 19:1–297
Hawksworth DL (1976) Lichen chemotaxonomy. In Brown DH, Hawksworth DL, Bailey RH (eds): Lichenology. Progress and problems, pp 139–184. London
Huneck S (1968) Lichen substances. In: Reinhold L and Liwschitz Y (ed): Progress in Phytochemistry. Vol 1, pp 223–346. Sydney: Intersci Publ, London, New York
Huneck S (1971) Chemie und Biosynthese der Flechtenstoffe. Fortschr Chem Organ Naturstoffe 29:209–306
Huneck S (1973) Nature of lichen substances. In: Ahmadjian V and Hale ME (ed): The Lichens, pp 495–522. New York and London: Academic Press
Huneck S (1984) Fortschritte der Chemie von Flechtenstoffen. Beih Nova Hedwigia 79:793–838
Huneck S (1991) New results in the chemistry of lichens. Symbiosis 11:225–248
Huneck S, Yoshimura I (1996) Identification of Lichen Substances. Berlin, Heidelberg: Springer-Verlag
Krog H, Östhagen H, Tönsberg T (1980) Lavflora. Norske busk-og bladlav. Oslo: Universitetsforlaget
Lawrey JD (1986) Biological role of lichen substances. Bryologist 89:111–122
Lawrey JD (1995) The chemical ecology of liehen mycoparasites. Can J Bot 73 (Suppl 1):S603–S608
Leuckert C (1984) Die Identifizierung von Flechtenstoffen im Rahmen chemotaxonomischer Routineanalysen. Beih Nova Hedwigia 79:839–869
Leuckert C (1985) Probleme der Flechten-Chemotaxonomie — Stoffkombinationen und ihre taxonomische Wertung. Ber Dtsch Bot Ges 98:401–408
Leuckert C, Knoph J-G (1992) European taxa of saxicolous Lecidella containing chloroxanthones: identification of patterns using thin layer chromatography. Lichenologist 24:383–397
Leuckert C, Dolling K, Wolters W (1979) Chemische Flechtenanalysen. Herzogia 5:181–185
Lumbsch HT (1998a) Taxonomic use of metabolic data in lichen-forming fungi. In: Frisvad JC, Bridge PD, Arora DK (eds): Chemical Fungal Taxonomy, pp 345–387. New York: Marcel Dekker
Lumbsch HT (1998b) The use of metabolic data in lichenology at the species and subspecific levels. Lichenologist 30:357–367
Mietzsch E, Lumbsch HT, Elix JA (1992) Wintabolites Users Manual. Essen
Mietzsch E, Lumbsch HT, Elix JA (1993) Notice: a new computer program for the identification of lichen substances. Mycotaxon 47:475–479
Moberg R, Holmsen I (1982) Lavar. En fälthandbok. Stockholm: Inetrpublishing
Mosbach K (1969) Zur Biosynthese von Flechtenstoffen, Produkten einer symbiotischen Lebensgemeinschaft. Angew Chem 81:233–244
Purvis OW, Elix JA, Broomhead JA, Jones GC (1987) The occurrence of copper-norstictic acid in lichens from cupriferous substrata. Lichenologist 19:193–203
Ramaut JL, Brouers MB, Serusiaux E, Corvisier M (1978) Separation of mixtures of atranorin and chloratranorin by thin-layer chromatography. J Chromatogr 155:450–453
Rikkinen J (1995) What’s behind the pretty colours? A study on the photobiology of lichens. Bryobrothera 4:1–239
Rogers RW (1989) Chemical variation and the species concept in lichenized ascomycetes. Bot J Linn Soc 101:229–239
Santesson J (1973) Identification and isolation of lichen substances. In Ahmadjian V and Hale ME (eds): The Lichens, pp 633–652. New York and London: Academic Press
Shibata S (1963) Lichen substances. In: Modern Methods of Plant Analysis. Vol VI, pp 155–193. Heidelberg: Springer-Verlag, Berlin
Steiner M (1955) Ein stabiles Diaminreagens für lichenologische Zwecke. Ber Dtsch Bot Ges 63:35–40
White FJ, James PW (1985) A new guide to microchemical techniques for the identification of lichen substances. Brit Lich Soc Bull 57:1–41
Yoshimura I. Kinoshita Y, Yamamoto Y, Huneck S, Yamada Y (1994) Analysis of secondary metabolites from lichen by high performance liquid chromatography with a photodiode array detector. Phytochem Anal 5:195–205
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2002 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Lumbsch, H.T. (2002). Analysis of Phenolic Products in Lichens for Identification and Taxonomy. In: Kranner, I.C., Beckett, R.P., Varma, A.K. (eds) Protocols in Lichenology. Springer Lab Manuals. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-56359-1_17
Download citation
DOI: https://doi.org/10.1007/978-3-642-56359-1_17
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-41139-0
Online ISBN: 978-3-642-56359-1
eBook Packages: Springer Book Archive