Chemotaxonomy and evolution of Plantago L.

Plant Systematics and Evolution

Volumn 242, Issue 1-4, 2003, Pages 63-82

  Ronsted N ^a,c   Franzyk, H ^a,b   Molgaard P ^a   Jaroszewski, J W ^a   Jensen, S R ^b  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^c JODRELL LABORATORY   (United Kingdom)

Author keywords

2 4 ( D glucopyranosyloxy) phenyl acetic acid; Caffeoyl phenylethanoid glycosides; Chemotaxonomy; Iridoid glucosides; Plantaginaceae; Plantago; Sorbitol

Indexed keywords

CORONOPUS; PLANTAGINACEAE; PLANTAGO; PLANTAGO OVATA;

EID: 0346040173     PISSN: 03782697     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00606-003-0057-3     Document Type: Article

References (68)

1. Afifi M. S., Salama O. M., Maatooq G. T. (1990) Phytochemical study of two Plantago species. Part II: Iridoid glucosides. Mansouri J. Pharm. Sci. 6: 16-25.
2. Afifi M. S., Zaghloul M. G., Hassan M. A. (2000) Phytochemical investigation of the aerial parts of Plantago ovata. Mansouri J. Pharm. Sci. 16: 178-190.
3. Albach D., Soltis P. S., Soltis D. E. (2001) Patterns of embryological and biochemical evolution in the asterids. Syst. Bot. 26: 242-262.
4. Andary C., Motte-Florac M. E., Gargadennec A., Wylde R., Heitz A. (1988) Les esters caféiques du genre Plantago. Identification et valeur chimotaxonomique. Pl. Méd. Phyt. 22: 17-22.
5. Andary C., Ravn H., Wylde R., Heitz A., Motte-Florac E. (1989) Crassifolioside, a caffeic acid glycoside ester from Plantago crassifolia. Phytochemistry 28: 288-290.
6. Andrzejewska-Golec E. (1997) Taxonomic aspects of the iridoid glucosides occurring in the genus Plantago L. Acta Soc. Bot. Pol. 66: 201-205.
7. Andrzejewska-Golec E., Ofterdinger-Daegel S., Calis I., Swiatek L. (1993) Chemotaxonomic aspects of iridoids occurring in Plantago subg. Psyllium (Plantaginaceae). Plant Syst. Evol. 185: 85-89.
8. Andrzejewska-Golec E., Swiatek L. (1984) Chemotaxonomic studies on the genus Plantago. I. Analysis of the iridoid fraction. Herba Pol. 30: 9-16.
9. Bello M. A., Chase M. W., Olmstead R. G., Rønsted N., Albach D. C. (2002) The páramo endemic Aragoa is the sister genus of Plantago (Plantaginaceae, Lamiales): evidence from plastid rbcL and nuclear ribosomal ITS sequence data. Kew Bull. 57: 585-697.
10. Bianco A., Guiso M., Passacantilli P., Francesconi A. (1984) Iridoid and phenylpropanoid glycosides from new sources. J. Nat. Prod. 47: 901-902.
11. Damtoft S. (1983) Biosynthesis of the iridoids aucubin and antirrhinoside from 8-epi-deoxyloganic acid. Phytochemistry 22: 1929-1930.
12. Damtoft S., Falkesgaard E., Jensen S. R. (1994) Iridoid glucosides from Plantago hookeriana. Phytochemistry 35: 1367-1368.
13. Damtoft S., Hansen S. B., Jacobsen B., Jensen S. R., Nielsen B. J. (1984) Iridoid glucosides from Melampyrum. Phytochemistry 23: 2387-2389.
14. Damtoft S., Jensen S. R., Jessen C. U., Knudsen T. B. (1993) Late stages in the biosynthesis of aucubin in Scrophularia. Phytochemistry 33: 1089-1093.
15. 1H NMR spectroscopy as a tool in the configurational analysis of iridoid glucosides. Phytochemistry 20: 2717-2732.
16. Damtoft S., Jensen S. R., Nielsen B. J. (1985) Iridoid glucosides from Utricularia australis and Pinguicula vulgar is (Lentibulariaceae). Phytochemistry 24: 2281-2283.
17. Damtoft S., Jensen S. R., Nielsen B. J. (1992) Biosynthesis of iridoid glucosides in Lamium album. Phytochemistry 31: 135-137.
18. Decaisne M. J. (1852) Plantaginaceae. In: de Candolle A. C. (ed.) Prodromus Systematis Naturalis Regni Vegetabilis. Vol. 13 (I). Victoris Masson, Paris, pp. 693-737.
19. Dietrich H. (1975) Cytologische Untersuchungen innerhalb der Familie der Plantaginaceae II. Wiss. Zeit. F.-Sch.-Univ. Jena Math.-Natur. R. 24: 437-461.
20. Franzyk H., Husum T. L., Jensen S. R. (1998) A caffeoyl phenylethanoid glycoside from Plantago myosorus. Phytochemistry 47: 1161-1162.
21. Gorenflot R., Bourdu R. (1962) Criteres biochimiques et taxonomie experimentale du genre Plantago. Rev. Cytol. Biol. Végetales 25: 349-360.
22. Grayer R. J., Chase M. W., Simmonds M. S. J. (1999) A comparison between chemical and molecular characters for the determination of phylogenetic relationships among plant families: An appreciation of Hegnauer's "Chemotaxonomie der Pflanzen". Biochem. Syst. Ecol. 27: 369-393.
23. Handjieva N., Spassov S., Bodurova G., Saadi H., Popov S., Pureb O., Zamjansan J. (1991) Majoroside, an iridoid glucoside from Plantago major. Phytochemistry 30: 1317-1318.
24. Handjieva N., Taskova R., Popov S. (1993) 10-Hydroxymajoroside, an iridoid glucoside from Plantago cornuti Gouan L. Z. Naturforsch. 48c: 827-828.
25. Harborne J. B., Williams C. A. (1971) 6-Hydroxyluteolin and scutellarein as phyletic markers in higher plants. Phytochemistry 10: 367-378.
26. Jensen S. R. (1991) Plant iridoids, their biosynthesis and distribution in angiosperms. In: Harborne J. B., Tomas-Barberan F. A. (eds.) Annual Proceedings of the Phytochemical Society of Europe. Ecological Chemistry and Biochemistry of Plant Terpenoids. Oxford University Press, Oxford, pp. 133-158.
27. Jensen S. R. (2000) Chemical relationships of Polypremum procumbens, Tetrachondra hamiltonii and Peltanthera floribunda. Biochem. Syst. Ecol. 28: 45-51.
28. Jensen S. R., Kirk O., Nielsen B. J. (1989) Biosynthesis of the iridoid glucoside cornin in Verbena officinalis. Phytochemistry 28: 97-105.
29. Jensen S. R., Olsen C. E., Rahn K., Rasmussen J. H. (1996) Iridoid glucosides in Plantago alpina and P. altissima. Phytochemistry 42: 1633-1636.
30. Junior P. (1985) Weitere Iridoidglucoside aus Penstemon strictus. Planta Med. 51: 229-232.
31. Kawashty S. A., Gamal-El-Din E., Abdalla M. F., Saleh N. A. M. (1994) Flavonoids of Plantago species in Egypt. Biochem. Syst. Ecol. 22: 729-733.
32. Kim D. H., Kim B. R., Kim J. Y., Jeong Y. C. (2000) Mechanism of covalent adduct formation of aucubin to proteins. Tox. Lett. 114: 181-188.
33. Kitagawa S., Tsukamoto H., Hisada S., Nishibe S. (1984) Studies on the Chinese crude drug "Forsythiae Fructus" VII. A new caffeoyl glycoside from Forsythia viridissima. Chem. Pharm. Bull. 32: 1209-13.
34. Konno K., Hirayama C., Shinbo H. (1998) Glycine protects against strong protein-denaturing activity of oleuropein. A phenolic compound in privet leaves. J. Chem. Ecol. 24: 735-751.
35. Konno K., Hirayama C., Yasui H., Nakamura M. (1999) Enzymatic activation of oleuropein: A protein crosslinker used as a chemical defense in the privet tree. Proc. Natl. Acad. Sci. 96: 9159-9164.
36. Krammer G. E., Buttery R. G., Takeoka G. R. (1995) Studies on Tomato glycosides. In: Rouseff R. L., Leahy M. M. (eds.) Fruit flavours. Biogenesis, characterization and authentication. ACS Symposium Series 596. American Chemical Society. Washington, pp. 164-181.
37. Kraus C., Spiteller G. (1997) Comparison of phenolic compounds from galls and shoots of Picea glauca. Phytochemistry 44: 59-67.
38. Kuzmanov B., Evstatieva L., Marekov N., Popov S. (1984) Chemosystematic study on genus Plantago L. Fitologia 24: 29-34.
39. Lahloub M. F., El-Sekbakhy N., El-Grazouly M., Gross G.-A., Sticher O. (1985) Auroside, a new iridoid glucoside from Phlomis aurea. Acta Agronom. 34 (Suppl), 57.
40. Murai M., Tamayama Y., Nishibe S. (1995) Phenylethanoids in the herb of Plantago lanceolata and inhibitory effect on arachidonic acid-induced mouse ear edema. Planta Med. 61: 479-480.
41. Murai M., Takenaka T., Nishibe S. (1996) Iridoids from P. major. Natural Med. 50: 306.
42. Mølgaard P. (1986) Population genetics and geographical distribution of caffeic acid esters in leaves of Plantago major in Denmark. J. Ecol. 74: 1127-1137.
43. Mølgaard P., Skjøth L., Kaufmann U. (1980) A genetic investigation of the esters of caffeic acid with rhamnose or glucose in leaves of Plantago major. Biochem. Syst. Ecol. 8: 277-278.
44. Nishibe S., Murai M., Tamayama Y. (1995) Studies on the constituents of Plantaginis Herba 7. Flavonoids from Plantago asiatica and P. hostifolia. Natural Med. 49: 340-342.
45. Nishibe S., Sasahara M., Ying J., Lu Y. C., Tanaka T. (1993) Phenylethanoid glycosides from Plantago depressa. Phytochemistry 32: 975-977.
46. Nishibe S., Tamayama Y., Sasahara M., Andary C. (1995) A phenylethanoid glycoside from Plantago asiatica. Phytochemistry 38: 741-743.
47. Noro Y., Hisata Y., Okuda K., Kawamura T., Kasahara Y., Tanaka T., Sakai E., Nishibe S., Sasahara M. (1991) Pharmacognostical studies of Plantaginis herba (VII). On the phenylethanoid contents of Plantago spp. Shoyakugaku Zasshi 45: 24-28.
48. Pilger R. (1937) Plantaginaceae. In: Engler A. (ed.) Das Pflanzenreich IV 269 (102). Wilhelm Engelmann, Leipzig.
49. Rahn K. (1978) Nomenclatorial changes within the genus Plantago L. Infraspecific taxa and subdivisions of the genus. Bot. Tidsskr. 73: 106-111.
50. Rahn K. (1996) A phylogenetic study of the Plantaginaceae. Bot. J. Linn. Soc. 120: 145-198.
51. Ravn H., Nishibe S., Sasahara M., Xuebo L. (1990) Phenolic compounds from Plantago asiatica. Phytochemistry 29: 3627-3631.
52. Rimpler H. (1991) Sequestration of iridoids by insects. In: Harborne J. B., Tomas-Barberan F. A. (eds.) Annual Proceedings of the Phytochemical Society of Europe. Ecological Chemistry and Biochemistry of Plant Terpenoids. Oxford University Press, Oxford, pp. 314-330.
53. Rønsted N., Jensen S. R. (2002) Iridoid glucosides and caffeoyl phenylethanoid glycosides from Campylanthus salsaloides and Campylanthus glaber. Biochem. Syst. Ecol. 30: 1091-1095.
54. Rønsted N., Göbel E., Franzyk H., Jensen S. R., Olsen C. E. (2000) Chemotaxonomy of Plantago. Iridoid glucosides and caffeoyl phenylethanoid glycosides. Phytochemistry 55: 337-348.
55. Rønsted N., Chase M. W., Albach D. C., Bello M. A. (2002) Phylogenetic relationships within Plantago (Plantaginaceae): evidence from nuclear ribosomal ITS and plastid trnL-F sequence data. Bot. J. Linn. Soc. 139: 323-338.
56. Rønsted N., Bello M. A., Jensen S. R. (2003) Aragoside and iridoid glucosides from Aragoa cundinamarcensis. Phytochemistry 64: 529-533.
57. Saadi H., Handjieva N., Popov S., Evstatieva L. (1990) Iridoids from Plantago media. Phytochemistry 29: 3938-3939.
58. Swiatek L., Lehmann D., Chaudhuri R. K., Sticher O. (1981) Occurrence of melittoside in the seeds of Plantago media. Phytochemistry 20: 2023-2024.
59. Taskova R., Handjieva N., Evstatieva L., Popov S. (1999) Iridoid glucosides from Plantago cornuti, Plantago major and Veronica cymbalaria. Phytochemistry 52: 1443-1445.
60. Taskova R., Evstatieva L., Handjieva N., Popov S. (2002) Iridoid patterns of genus Plantago L. and their taxonomic significance. Z. Naturforsch. 57c: 42-50.
61. Tomas-Barberan F. A., Grayer-Barkmeijer R. J., Gil M. I., Harborne J. B. (1988) Distribution of 6-hydroxy-, 6-methoxy-and 8-hydroxyflavone glycosides in the Labiatae, the Scrophulariaceae and related families. Phytochemistry 28: 2631-2645.
62. Uesato S., Miyauchi M., Itoh H., Inouye H. (1986) Biosynthesis of iridoid glucosides in Galium mollugo, G. spurium var. echinospermon and Deutzia crenata. Intermediacy of deoxyloganic acid, loganin and iridodial glucoside. Phytochemistry 25: 2511-2521.
63. Ushiyama M., Asada Y., Yoshikawa T., Furuya T. (1989) Biotransformation of aromatic carboxylic acids by root culture of Panax ginseng. Phytochemistry 28: 1859-1869.
64. Velázquez-Fiz M. P., Diaz-Lanza A. M., Fernandez-Matellano L. (2000a) Polyphenolic compounds from Plantago lagopus L. Z. Naturforsch. 55c: 877-880.
65. Velázquez-Fiz M. P., Diaz-Lanza A. M., Fernandez-Matellano L. (2000b) Iridoids from Plantago lagopus. Pharm. Biol. 38: 268-270.
66. Wahlberg N. (2001) The phylogenetics and biochemistry of host-plant specialization in melitaeine butterflies (Lepidoptera: Nymphalidae). Evolution 55: 522-537.
67. Wallaart R. A. M. (1980) Distribution of sorbitol in the Rosaceae. Phytochemistry 19: 2603-2610.
68. Wallaart R. A. M. (1981) Acyclic polyols as taxonomic characters. P. K. Ned. Akad. Wetensc. Ser. C 84: 77-87.