Unusual iridoid glycosides in Veronica sects. Hebe and Labiatoides

Biochemical Systematics and Ecology

Volumn 36, Issue 3, 2008, Pages 207-215

  Jensen, Søren Rosendal ^a   Gotfredsen, Charlotte Held ^a   Grayer, Renée J ^b  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^b ROYAL BOTANIC GARDENS   (United Kingdom)

Author keywords

6 O Aucubin esters; 6 O Rhamnopyranosyl iridoids; Chemosystematics; Derwentia; Iridoid glucosides; Mannitol; Parahebe; Plantaginaceae; V. catarractae; V. perfoliata; Veronica derwentiana

Indexed keywords

ANGIOSPERM; CHEMOTAXONOMY; GEOGRAPHICAL DISTRIBUTION; IDENTIFICATION METHOD; NEW GENUS; NEW SPECIES; PHYLOGENETICS; SOUTHERN HEMISPHERE;

DERWENTIA; HEBE; PARAHEBE; PLANTAGINACEAE; VERONICA;

EID: 37748998922     PISSN: 03051978     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bse.2007.09.011     Document Type: Article

References (47)

1. Afifi-Yazar F.U., and Sticher O. Verproside, a new iridoid glucoside from Veronica officinalis L. (Scrophulariaceae). Helv. Chim. Acta 63 (1980) 1905-1907
2. Albach D.C., and Chase M.W. Paraphyly of Veronica (Veroniceae; Scrophulariaceae): evidence from the internal transcribed spacer (ITS) sequences of nuclear ribosomal DNA. J. Plant Res. 114 (2001) 9-18
3. Albach D.C., and Chase M.W. Incongruence in Veroniceae (Plantaginaceae): evidence from two plastid and a nuclear ribosomal DNA region. Mol. Phylogenet. Evol. 32 (2004) 183-197
4. Albach D.C., Martínez-Ortega M.M., Fischer M.A., and Chase M.W. A new classification of the tribe Veroniceae - problems and a possible solution. Taxon 53 (2004) 429-452
5. Albach D.C., Meudt H.M., and Oxelman B. Piecing together the "new" Plantaginaceae. Am. J. Bot. 92 (2005) 297-315
6. Albach D.C., Utteridge T., and Wagstaff S.J. Origin of Veroniceae (Plantaginaceae, formerly Scrophulariaceae) on New Guinea. Syst. Bot. 30 (2005) 412-423
7. APG (Angiosperm Phylogeny Group). An update of the Angiosperm Phylogeny Group classification for the orders and families of flowering plants: APG II. Bot. J. Linn. Soc. 141 (2003) 399-436
8. Bianco A., Guiso M., Iavarone C., Passacantilli P., and Trogolo C. Iridoids. XXIX. Sinuatol (6-O-α-l-rhamnopyranosylaucubin) from Verbascum sinuatum. Planta Med. 41 (1981) 75-79
9. Bianco A., Passacantilli P., Polidori G., Nicoletti M., and Messana I. NMR spectroscopy of epimeric pairs of glucosidic iridoids. Gazz. Chim. Ital. 113 (1983) 829-834
10. Bock K., and Pedersen C. Carbon-13 nuclear magnetic resonance spectroscopy of monosaccharides. Adv. Carbohydr. Chem. Biochem 41 (1983) 27-66
11. Briggs B.G., and Ehrendorfer F. New combinations in Parahebe. Taxon 17 (1968) 742
12. Briggs B.G., and Ehrendorfer F. A revision of the Australian species of Parahebe and Derwentia (Scrophulariaceae). Telopea 5 (1992) 241-287
13. Calis I., Kirmizibekmez H., Tasdemir D., Sticher O., and Ireland C.M. Sugar esters from Globularia orientalis. Z. Naturforsch. Sect. C Biosci. 57 (2002) 591-596
14. 1H NMR spectroscopy as a tool in the configurational analysis of iridoid glucosides. Phytochemistry 20 (1981) 2717-2732
15. Demuth H., Jensen S.R., and Nielsen B.J. Iridoid glucosides from Asystasia bella. Phytochemistry 28 (1989) 3361-3364
16. El-Naggar S., and Doskotch R.W. Specioside: a new iridoid glycoside from Catalpa speciosa. J. Nat. Prod. 43 (1980) 524-526
17. Garnock-Jones P.J., Albach D.C., and Briggs B.G. Botanical names in Southern Hemisphere Veronica (Plantaginaceae): sect. Detzneria, sect. Hebe, and sect. Labiatoides. Taxon 56 (2007) 571-582
18. Grayer-Barkmeijer R.J. A chemotaxonomic study of Veronica: iridoid glucosides. Biochem. Syst. 1 (1973) 101-110
19. Grayer-Barkmeijer R.J. Flavonoids in Parahebe and Veronica: a chemotaxonomic study. Biochem. Syst. Ecol. 6 (1978) 131-137
20. Grayer-Barkmeijer, R.J., 1979. Chemosystematic Investigations in Veronica L. (Scrophulariaceae) and Related Genera. Ph.D. thesis, University of Leiden, The Netherlands.
21. Flora of New South Wales, vol. 3. In: Harden G.J. (Ed) (1992), New South Wales University Press, Kensington
22. Harput U.S., Saracoglu I., Inoue M., and Ogihara Y. Phenylethanoid and iridoid glycosides from Veronica persica. Chem. Pharm. Bull. 50 (2002) 869-871
23. Helfrich E., and Rimpler H. Iridoid glycosides and phenolic glycosides from Holmskioldia sanguinea. Phytochemistry 50 (1999) 619-627
24. Jensen S.R., Albach D.C., Ohno T., and Grayer R.J. Veronica: Iridoids and cornoside as chemosystematic markers. Biochem. Syst. Ecol. 33 (2005) 1031-1047
25. Johansen M., Larsen T.S., Mattebjerg M.A., Gotfredsen C.H., and Jensen S.R. Chemical markers in Veronica sect. Hebe. Biochem. Syst. Ecol. 35 (2007) 614-620
26. Junior P. Iridoid glucosides and an acetophenone glucoside from Penstemon whippleanus. Planta Med. 50 (1984) 444-445
27. Junior P. Acetophenone glucosides from Penstemon pinifolius. Planta Med. 52 (1986) 218-220
28. Kapoor S.K., Kohli J.M., and Zaman A. Amphicoside. I. New bitter glycoside from Amphicome emodi. Tetrahedron Lett. (1971) 2839-2840
29. Olmstead R.G., and Reeves P.A. Polyphyletic origin of the Scrophulariaceae: evidence from rbcL and ndhF sequences. Ann. Missouri Bot. Gard. 82 (1995) 176-193
30. Olmstead R.G., DePamphilis C.W., Wolfe A.D., Young N.D., Elisons W.J., and Reeves P.A. Disintegration of the Scrophulariaceae. Am. J. Bot. 88 (2001) 348-361
31. Oxelman B., Kornhall P., Olmstead R.G., and Bremer B. Further disintegration of Scrophulariaceae. Taxon 54 (2005) 411-426
32. Ozipek M., Saracoglu I., Maruyama M., Takeda T., and Calis I. Iridoid glucosides from Veronica fuhsii. Hacettepe Univ. J. Fac. Pharm. 18 (1998) 9-14
33. Pedersen P., Gotfredsen C.H., Wagstaff S.J., and Jensen S.R. Chemical markers in Veronica sect. Hebe. II. Biochem. Syst. Ecol. 35 (2007) 777-784
34. Rønsted N., Göbel E., Franzyk H., Jensen S.R., and Olsen C.E. Chemotaxonomy of Plantago. Iridoid glucosides and caffeoyl phenylethanoid glycosides. Phytochemistry 55 (2000) 337-348
35. Stermitz F.R., Foderaro T.A., and Li Y.X. Chemistry of the Scrophulariaceae. Part 26. Iridoid glycoside uptake by Castilleja integra via root parasitism on Penstemon teucrioides. Phytochemistry 32 (1993) 1151-1153
36. Sticher O., and Afifi-Yazar F.U. Minecoside and verminoside, two new iridoid glucosides from Veronica officinalis L. (Scrophulariaceae). Helv. Chim. Acta 62 (1979) 535-539
37. Sticher O., Meier B., Lehmann D., and Swiatek L. Scrophularioside, a new iridoid glucoside from Scrophularia lateriflora. Planta Med. 38 (1980) 246-254
38. Strunz G.M., Giguere P., and Thomas A.W. Synthesis of pungenin, a foliar constituent of some spruce species, and investigation of its efficacy as a feeding deterrent for spruce budworm [Choristoneura fumiferana (Clem.)]. J. Chem. Ecol. 12 (1986) 251-260
39. Stuppner H., and Wagner H. Minor iridoid and phenol glycosides of Picrorhiza kurrooa. Planta Med. 55 (1989) 467-469
40. Sun X., Shen G., and Tian X. Chemical components of Scrofella chinensis (II). Acta Bot. Boreal. Occident. Sin. 26 (2006) 412-415
41. Taskova R., Handjieva N., Peev D., and Popov S. Iridoid glucosides from three Veronica species. Phytochemistry 49 (1998) 1323-1327
42. Taskova R.M., Gotfredsen C.H., and Jensen S.R. Chemotaxonomic markers in Digitalideae (Plantaginaceae). Phytochemistry 66 (2005) 1440-1447
43. Taskova R.M., Gotfredsen C.H., and Jensen S.R. Chemotaxonomy of Veroniceae and its allies in the Plantaginaceae. Phytochemistry 67 (2006) 286-301
44. Vesper T., and Seifert K. Iridoids and other glucosides from Penstemon acuminatus. Phytochemistry 37 (1994) 1087-1089
45. Wagstaff S.J., Bayly M.J., Garnock-Jones P.J., and Albach D.C. Classification, origin and diversification of the New Zealand hebes (Scrophulariaceae). Ann. Missouri Bot. Gard. 89 (2002) 38-63
46. Wang H., Sun Y., Ye W.-C., Xiong F., Wu J.-J., Yang C.-H., and Zhao S.-X. Antioxidative phenylethanoid and phenolic glycosides from Picrorhiza scrophulariiflora. Chem. Pharm. Bull. 52 (2004) 615-617
47. Yang X.-D., Yang L.-J., Yang S., Zhao J.-F., Zhang H.-B., and Li L. Two new iridoid glycosides from Lagotis yunnanensis. Z. Naturforsch. Sect. B Chem. Sci. 62 (2007) 749-752