Download PDF
Planta Med 2001; 67(3): 199-208
DOI: 10.1055/s-2001-12012
Review

© Georg Thieme Verlag Stuttgart · New York

Polysaccharides from Lichens: Structural Characteristics and Biological Activity

Elin S. Olafsdottir*, Kristín Ingólfsdottir
  • Faculty of Pharmacy, University of Iceland, Reykjavik, Iceland
Further Information

Publication History

June 19, 2000

October 8, 2000

Publication Date:
31 December 2001 (online)

Also available at
   Permissions and Reprints

Abstract

Lichens have been used for medicinal purposes throughout the ages, and beneficial claims have to some extent been correlated with their polysaccharide content. Of 13,500 lichen species growing worldwide, less than 100 species have been investigated for polysaccharide content. Lichen polysaccharides are mainly of three different structural types: β-glucans, α-glucans, and galactomannans. In addition, a few complex heteroglycans have recently been described, such as thamnolan, a water-soluble, immunologically active heteroglycan with a novel rhamnopyranosylgalactofuranan type of structure. A number of investigations have been carried out on biological effects of lichen polysaccharides, most notably antitumour, immunomodulating, antiviral, and memory-enhancing effects. The current review summarizes present knowledge on the structural characteristics and biological activity of lichen polysaccahrides.

Key words

Lichens - polysaccharides - structural characteristics - antitumour activity - immunological activity - biological activity

References

  • 1 Huneck S, Yoshimura I. Identification of Lichen Substances. Berlin; Springer Verlag 1996
  • 2 Gorin P AJ, Baron M, Silva M LC, Teixeira A ZA, Iacomini M. Lichen carbohydrates.  Ciencia e Cultura (Journal of the Brazilian Association for the Advancement of Science). 1993;  45 27-36
    PubMedSearch in Google Scholar
  • 3 Barreto-Bergter E. Chemical Structure, Immunology and Application of Polysaccharides of Fungi and Lichens. In: Atta-ur-Rahman, editor Studies in Natural Products Chemistry Vol. 5, Structure Elucidation (Part B). Amsterdam; Elsevier 1989: 275-340
    Search in Google Scholar
  • 4 Gorin P AJ, Baron M, Iacomini M. Storage Products of Lichens. In: Galun M, editor CRC Handbook of Lichenology Vol. 3. Florida; CRC Press 1988: 9-23
    Search in Google Scholar
  • 5 Gorin P AJ, Barreto-Bergter E. The Chemistry of Polysaccharides of Fungi and Lichens. In: Aspinall GO, editor The Polysaccharides Vol. 2. New York; Academic Press 1983: 389-94
    Search in Google Scholar
  • 6 Olafsdottir E S, Omarsdottir S, Smestad Paulsen B, Jurcic K, Wagner H. Rhamnopyranosylgalactofuranan, a new immunologically active polysaccharide from Thamnolia subuliformis .  Phytomedicine. 1999;  6 (4) 273-9
    PubMedSearch in Google Scholar
  • 7 Iacomini M, Zanin S MW, Fontana J D. Isolation and characterization of β-D-glucan, heteropolysaccharide, and trehalose components of the Basidiomycetous lichen Cora pavonia .  Carbohydrate Research. 1987;  168 55-65
    CrossrefPubMedSearch in Google Scholar
  • 8 Common R S. The distribution and taxonomic significance of lichenan and isolichenan in the Parmeliaceae (lichenized Ascomycotina), as determined by iodine reactions. I. Introduction and methods. II. The genus Alectoria and associated taxa.  Mycotaxon. 1991;  XLI 67-112
    PubMedSearch in Google Scholar
  • 9 Teixeira A ZA, Iacomini M, Gorin P AJ. Chemotypes of mannose-containing polysaccharides of lichen mycobionts: a possible aid in classification and identification.  Carbohydrate Research. 1995;  266 309-14
    CrossrefPubMedSearch in Google Scholar
  • 10 Takahashi K, Takeda T, Shibata S. Polysaccharides of lichen symbionts.  Chemical & Pharmaceutical Bulletin. 1979;  27 (1) 238-41
    PubMedSearch in Google Scholar
  • 11 Konig J, Pevelung E. Cell wall of the phycobiont Trebouxia and Pseudotrebouxia: Constituents and their localization.  Lichenologist. 1984;  16 129-44
    PubMedSearch in Google Scholar
  • 12 Stone B A, Clarke A E. Chemistry and Biology of (1-3)-β-Glucans. Victoria, Australia; La Trobe University Press 1992: 60-75, 283 - 358
  • 13 Vartia K O. Antibiotics from Lichens. In: Ahmadjian V, Hale MS, editors The Lichens. New York; Academic Press 1973: 547
    Search in Google Scholar
  • 14 Ingólfsdóttir K. Bioactive Compounds in Iceland Moss. In: Smestad-Paulsen B, editor Bioactive Carbohydrate Polymers, Proceedings Phytochemical Society of Europe. Dordrecht; Kluwer Academic Publishers 2000: 25-36
    Search in Google Scholar
  • 15 Baron M, Iacomini M, Fanta E, Gorin P AJ. Galactomannan, lichenan and isolichenan from the polysaccharide-rich lichen Newropogon aurantiago-ater .  Phytochemistry. 1991;  30 3125-6
    CrossrefPubMedSearch in Google Scholar
  • 16 Smith A L. Lichens. Cambridge University Press 1921
    Search in Google Scholar
  • 17 Takeda T, Funatsu M, Shibata S, Fukuoka F. Polysaccharides of lichens and fungi V. Antitumor active polysaccharides of Evernia, pacroscyphus and Alectoria species.  Chemical & Pharmaceutical Bulletin. 1972;  20 2445-9
    PubMedSearch in Google Scholar
  • 18 Chanda N B, Hirst E L, Manners D J. A comparison of isolichenin and lichenin from Iceland moss (Cetraria islandica).  Journal of Chemical Society. 1957;  1951-8
    CrossrefPubMedSearch in Google Scholar
  • 19 Peat S, Whelan W J, Turvey J R, Morgan K. The structure of isolichenin.  Journal of Chemical Society. 1961;  623-9
    CrossrefPubMedSearch in Google Scholar
  • 20 Olafsdottir E S, Ingolfsdottir K, Barsett H, Smestad Paulsen B, Jurcic K, Wagner H. Immunologically active (1→3)-(1→4)-α-D-glucan from Cetraria islandica .  Phytomedicine. 1999;  6 (1) 33-9
    PubMedSearch in Google Scholar
  • 21 Ulander A, Tollens B. Untersuchungen über die Kohlenhydrate der Flechten.  Berichte der deutschen chemischen Gesellschaft. 1906;  39 401
    PubMedSearch in Google Scholar
  • 22 Preston J F, Gander J E. Isolation and partial characterization of the extracellular polysaccharides of Penicillium charlesii .  Archives of Biochemistry and Biophysics. 1968;  124 504-12
    CrossrefPubMedSearch in Google Scholar
  • 23 Prado S RT, Gorin P AJ, Stuelp P M, Honda N K, Iacomini M. An unusual juxtaposition of polysaccharide components of Collema leptosporum .  Carbohydrate Polymers. 1999;  40 271-6
    CrossrefPubMedSearch in Google Scholar
  • 24 Ingolfsdottir K, Jurcic K, Fischer B, Wagner H. Immunologically active polysaccharide from Cetraria islandica .  Planta Medica. 1994;  60 527-31
    PubMedSearch in Google Scholar
  • 25 Iacomini M, Schneider C L, Gorin P AJ. Comparative studies on the polysaccharides of Cladonia alphestris (Reindeer moss), Cladonia confusa and Cladonia amaurocraea .  Carbohydrate Research. 1985;  142 237-51
    CrossrefPubMedSearch in Google Scholar
  • 26 Shibata S. Polysaccharides of lichens.  Journal of the National Science Council of Sri Lanka. 1973;  1 183-8
    PubMedSearch in Google Scholar
  • 27 Woranovicz-Barreira S M, Gorin P AJ, Sassaki G L, Tischer C A, Ahti T, Iacomini M. Chemotyping glucans from lichens of the genus Cladonia .  Phytochemistry. 1999;  52 1069-74
    CrossrefPubMedSearch in Google Scholar
  • 28 Nishikawa Y, Ohki K, Takahashi K, Kurono G, Fukuoka F, Emori M. Studies on the water soluble constituents of lichens. II. Antitumor polysaccharides of Lasallia, Usnea and Cladonia Species.  Chemical & Pharmaceutical Bulletin. 1974;  22 2692-702
    PubMedSearch in Google Scholar
  • 29 Woranovicz-Barreira S M, Pinto B M, Gorin P AJ, Iacomini M. Novel structures in galactomannans of the lichens Cladonia substellata and Cladonia ibitipocae: Significance as chemotypes.  Phytochemistry. 1999;  51 395-402
    CrossrefPubMedSearch in Google Scholar
  • 30 Gorshkova R P, Nazarenko E L, Zubkov V A, Stepanenko L S, Isakov V V. Structural study of polysaccharides from Cetraria cucullata and Cetraria islandica lichens.  Russian Journal of Bioorganic Chemistry. 1997;  23 (2) 122-5
    PubMedSearch in Google Scholar
  • 31 Gorin P A, Iacomini M. Polysaccharides of the lichens Cetraria islandica and Ramalina usnea .  Carbohydr. Res.. 1984;  128 119-32
    CrossrefPubMedSearch in Google Scholar
  • 32 Mittal O P, Neelakantan S, Seshadri T R. Chemical investigations of Indian lichens. Part XIV.  Journal of Scientific and Industrial Research (India). 1952;  11B 386-7
    PubMedSearch in Google Scholar
  • 33 Yokota I, Shibata S, Saito H. A 13C-n.m.r. analysis of linkages in lichen polysaccharides: an approach to chemical taxonomy of lichens.  Carbohydrate Research. 1979;  69 252-8
    CrossrefPubMedSearch in Google Scholar
  • 34 Teixeira A ZA, Iacomini M, Gorin P AJ. An unusual glucomannan from Tornabenia incarnata .  Phytochemistry. 1992;  31 3467-70
    CrossrefPubMedSearch in Google Scholar
  • 35 Micovic V M, Hranisavljevic-Jakovljevic M, Miljkovic-Stojanovic J. Structural study of polysaccharides from the oak lichen Evernia prunastri (L.)  Ach. Carbohydrate Research. 1969;  10 525-33
    PubMedSearch in Google Scholar
  • 36 Iacomini M, Gorin P AJ, Baron M, Tulloch A P, Mazurek M. Novel D-glucans obtained by dimethyl sulphoxide extraction of the lichens Letharia vulpina, Actinogyra muehlenbergii and an Usnea sp.  Carbohydrate Research. 1988;  176 117-26
    CrossrefPubMedSearch in Google Scholar
  • 37 Gorin P AJ, Iacomini M. Structural diversity of galactomannan components isolated from lichens having Ascomycetous mycosymbionts.  Carbohydrate Research. 1985;  142 253-67
    CrossrefPubMedSearch in Google Scholar
  • 38 Takeda T, Nishikawa Y, Shibata S. A new α-glucan from the lichen Parmelia caperata (L.)  Ach. Chemical & Pharmaceutical Bulletin. 1970;  18 (5) 1074-5
    PubMedSearch in Google Scholar
  • 39 Smriga M, Saito H, Shibata S, Narui T, Okuyama T, Nishiyama N. PC-2, linear homoglucan with α-linkages, peripherally enhanches the hippocampal long-term potentiation.  Pharmaceutical Research. 1996;  13 (9) 1322-6
    CrossrefPubMedSearch in Google Scholar
  • 40 Olafsdottir E S. Unpublished results. 
  • 41 Nishikawa Y, Takeda T, Shibata S, Fukuoka F. Polysaccharides in lichens and fungi III. Further investigation on the structures and the antitumor activity of the polysaccharides from Gyrophora esculenta Miyoshi and Lasailla papulosa (Ach.) Llano.  Chemical & Pharmaceutical Bulletin. 1969;  17 1910-6
    PubMedSearch in Google Scholar
  • 42 Periera E C, Nascimento S C, Lima R C, Silva N H, Oliveira A F, Bandeira E, Boitard M, Beriel H, Vicente C, Legaz M E. Analysis of Usnea fasciata crude extracts with antineoplastic activity.  Tokai Journal of Experimental and Clinical Medicine. 1994;  19 47-52
    PubMedSearch in Google Scholar
  • 43 Mittal O P, Seshadri T R. Chemical investigation of Indian lichens XVI. Purification and composition of lichenin and isolichenin from Indian lichens.  Journal of Scientific and Industrial Research (India). 1954;  13B 244-5
    PubMedSearch in Google Scholar
  • 44 Shibata S, Nishikawa Y, Takeda T, Tanaka M, Fukuoka F, Nakanishi M. Studies on the chemical structures of the new glucans isolated from Gyrophora esculenta Miyoshi and Lasailla papulosa (Ach.) Llano and their inhibiting effect on implanted sarcoma 180 in mice.  Chemical & Pharmaceutical Bulletin. 1968;  16 1639-41
    PubMedSearch in Google Scholar
  • 45 Nishikawa Y, Tanaka M, Shibata S, Fukooka F. Polysaccharides of lichens and fungi IV. Antitumor active O-acetylated pustulan-type glucans from lichens of Umbilicaria species.  Chemical & Pharmaceutical Bulletin. 1970;  18 1431-4
    PubMedSearch in Google Scholar
  • 46 Lindberg B, McPherson J. Studies on the chemistry of lichens VI. The structure of pustulan.  Acta Chemica Scandinavica. 1954;  8 985
    PubMedSearch in Google Scholar
  • 47 Kjölberg O, Kvernheim A L. Studies on the polysaccharides III. The structure of alkali-soluble polysaccharides in Umbilicaria pustulata (L.) Hoffm. and Umbilicaria spodochroa (Arch.) Hoffm.  Acta Chemica Scandinavica. 1989;  43 280-5
    PubMedSearch in Google Scholar
  • 48 Stuelp P M, Carneiro Leao A MA, Gorin P AJ, Iacomini M. The glucans of Ramalina celastri: Relation with chemotypes of other lichens.  Carbohydrate Research. 1999;  40 101-6
    PubMedSearch in Google Scholar
  • 49 Miceno A M, Gorin P AJ, Iacomini M. Galactomannan and isolichenan components of the carbohydrate-rich lichen Ramalina ecklonii .  Agricultural and Biological Chemistry. 1991;  55 1391-2
    PubMedSearch in Google Scholar
  • 50 Takahashi K, Kon K, Yokota I, Shibata S. Chemotaxonomic studies on the polysaccharides of lichens.  Polysaccharides of Stereocaulaceous lichens.. Carbohydrate Research. 1981;  89 166-73
    PubMedSearch in Google Scholar
  • 51 Yokota I, Shibata S. A polysaccharide of the lichen Stereocaulon japonicum .  Chemical & Pharmaceutical Bulletin. 1978;  26 2668-70
    PubMedSearch in Google Scholar
  • 52 Hauan E, Kjölberg O. Studies on the polysaccharides of lichens. I. The structure of a water-soluble polysaccharide in Stereocaulon paschale (L.) Fr.  Acta Chemica Scandinavica. 1971;  25 2622-8
    PubMedSearch in Google Scholar
  • 53 Baron M, Gorin P, Iacomini M. Structural studies on the galactomannan isolated from the lichen Stereocaulon ramulosum .  Agricultural and Biological Chemistry. 1989;  53 1751-8
    PubMedSearch in Google Scholar
  • 54 Baron M, Gorin P AJ, Iacomini M. Isolation and identification of a linear (1→3)-linked β-D-glucan and other carbohydrate components of the lichen Stereocaulon ramulosum (Sw.) Rausch.  Carbohydrate Research. 1988;  177 235-9
    CrossrefPubMedSearch in Google Scholar
  • 55 Corradi da Silva M DL, Iacomini M, Jablonski E, Gorin P AJ. Carbohydrate, glycopeptide and protein components of the lichen Sticta sp. and effect of storage.  Phytochemistry. 1993;  33 547-52
    CrossrefPubMedSearch in Google Scholar
  • 56 Krämer P, Wincierz U, Grüber G, Tschakert J, Voelter W, Mayer H. Rational approach to fractionation, isolation and characterization of poylsaccharides from the lichen Cetraria islandica .  Arzneimittel - Forschung/Drug Research. 1995;  45 (I) 726-31
    PubMedSearch in Google Scholar
  • 57 Whistler R L, Bushway A A, Singh P P. Noncytotoxic, antitumour polysaccharides.  Advances in Carbohydrate Chemistry and Biochemistry. 1976;  32 235-75
    PubMedSearch in Google Scholar
  • 58 Wagner H. Immunomodulatory agents from plants. Progress in Inflammation Research. Parnham M, series editor Basel; Birkhauser Verlag 1999
  • 59 Franz G. Polysaccharides in pharmacy: Current applications and future concepts.  Planta Medica. 1989;  55 493-7
    PubMedSearch in Google Scholar
  • 60 Fukuoka F. et al. Polysaccharides in lichens and fungi. II. Antitumor activities on sarcoma-180 of the polysaccharide preparations from Gyrophora esculenta Miyoshi, Cetraria islandica (L.). Ach. var. Orientalis Asahina, and some other lichens.  GANN Japanese Journal of Cancer Research. 1968;  59 421-32
    PubMedSearch in Google Scholar
  • 61 Nishikawa Y, Ohno H. Studies on the water-soluble constituents of lichens. IV. Effect of antitumor lichen-glucans and related derivatives on the phagocytic activity of the reticuloendothelial system in mice.  Chemical & Pharmaceutical Bulletin. 1981;  29 (11) 3407-10
    PubMedSearch in Google Scholar
  • 62 Takahashi K, Takeda T, Shibata S, Inomata M, Fukuoka F. Polysaccharides of lichens and fungi. VI. Antitumour active polysaccharides of lichens of Stictaceae.  Chemical & Pharmaceutical Bulletin. 1974;  22 (2) 404-8
    PubMedSearch in Google Scholar
  • 63 Konopa J, Privett O S, Jenkin H M, Goldin A. Polysaccharides as stimulators of nonspecific immunological response against syngeneic tumors in mice. In: Sigienthaler W, Luthy R, editors Current Chemotherapy: Proceedings of the 10th International Congress of Chemotherapy. Washington D.C.; American Society for Microbiology 1978: 1095-7
    Search in Google Scholar
  • 64 Watanabe M, Iwai K, Shibata S, Takahashi K, Narui T, Tashiro T. Purification and characterization of mouse α1-acid glycoprotein and its possible role in the antitumor activity of some lichen polysaccharides.  Chemical & Pharmaceutical Bulletin. 1986;  34 (6) 2532-41
    PubMedSearch in Google Scholar
  • 65 Tokuzen R, Nakahara W, Fukuoka F, Shibata S, Nishikawa Y. Liver changes in mice treated with lichen polysaccharides.  Toxicology and Applied Pharmacology. 1970;  17 529-37
    CrossrefPubMedSearch in Google Scholar
  • 66 Ingólfsdóttir K, Jurcic K, Wagner H. Immunomodulating polysaccharides from aqueous extracts of Iceland moss.  Phytomedicine. 1998;  5 (5) 333-9
    PubMedSearch in Google Scholar
  • 67 Leao A MAC, Buchi D F, Iacomini M, Gorin P AJ, Oliveira M BM. Cytotoxic effect against HeLA cells of polysaccharides from the lichen Ramalina celastri .  Journal of Submicroscopic Cytology and Pathology. 1997;  29 (4) 503-9
    PubMedSearch in Google Scholar
  • 68 Stübler D, Buchenauer H. Antiviral activity of the glucan lichenan (poly-β-(1→3,1→4)-D-anhydroglucose). I. Biological activity in tobacco plants.  Journal of Phytopathology. 1996;  144 37-43
    PubMedSearch in Google Scholar
  • 69 Stübler D, Buchenauer H. Antiviral activity of the glucan lichenan (poly-β-(1→3,1→4)-D-anhydroglucose). II. Studies on the mode of action.  Journal of Phytopathology. 1996;  144 45-52
    PubMedSearch in Google Scholar
  • 70 Smriga M, Chen J, Zhang J-T, Narui T, Shibata S, Hirano E, Saito H. Isolichenan, an α-glucan isolated from the lichen Cetrariella islandica, repairs impaired learning behaviour and facilitates hippocampal synaptic plasticity.  Proceedings Japan Academie. 1999;  75, Ser. B 219-23
    PubMedSearch in Google Scholar
  • 71 Smriga M, Saito H. Effect of selected thallophytic glucans on learning behaviour and short-term potentiation.  Phytotherapy Research. 2000;  14 (3) 153-5
    CrossrefPubMedSearch in Google Scholar
  • 72 Nishikawa Y. et al. Studies on the water-soluble constituents of lichens. III. Changes in antitumor effect caused by modifications of pustulan- and lichenan-type glucans.  Chemical & Pharmaceutical Bulletin. 1979;  27 (9) 2065-72
    PubMedSearch in Google Scholar
  • 73 Hirabayashi K, Iwata S, Ito M, Shigeta S, Narui T, Mori T, Shibata S. Inhibitory effect of a lichen polysaccharide sulfate, GE-3-S, on the replication of human immuno-deficiency virus (HIV) in vitro .  Chemical & Pharmaceutical Bulletin. 1989;  37 (9) 2410-12
    PubMedSearch in Google Scholar
  • 74 Bohn J A, BeMiller J N. (1→3)-β-D-Glucans as biological response modifiers.  Carbohydrate Polymers. 1995;  28 3-14
    CrossrefPubMedSearch in Google Scholar
  • 75 Maeda Y Y, Chihara G. Lentinan and other antitumoural polysaccharides. In: Wagner H, editor Immunomodulatory Agents from Plants. Basel; Birkhauser Verlag 1999: 203-23
    Search in Google Scholar

Dr. E. S. Olafsdottir

Faculty of Pharmacy

University of Iceland

Hagi, Hofsvallagata 53

107 Reykjavik

Iceland

Email: elinsol@hi.is

Fax: +354 525 4071