Cyanogenic glycosides and menisdaurin from Guazuma ulmifolia, Ostrya virginiana, Tiquilia plicata, and Tiquilia canescens

Phytochemistry

Volumn 66, Issue 13, 2005, Pages 1567-1580

  Seigler, David S ^a   Pauli, Guido F ^b   Fröhlich, Roland ^c   Wegelius, Elina ^d   Nahrstedt, Adolf ^c   Glander, Kenneth E ^e   Ebinger, John E ^f  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^c UNIVERSITY OF MÜNSTER   (Germany)

^d UNIVERSITY OF JYVÄSKYLÄ   (Finland)

^e DUKE UNIVERSITY   (United States)

^f EASTERN ILLINOIS UNIVERSITY   (United States)

Author keywords

(2R) Taxiphyllin; (2S) Dhurrin; Betulaceae; Boraginaceae; Cyanogenic glycosides; Guazuma ulmifolia; Long range coupling; Menisdaurin; Nitrile glucosides; Ostrya virginiana; Sterculiaceae; Tiquilia canescens; Tiquilia plicata

Indexed keywords

BENZOFURAN DERIVATIVE; CYANOGENIC GLYCOSIDES; DHURRIN; GLUCOSIDE; GLYCOSIDE; MENISDAURIN; NITRILE;

ANGIOSPERM; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; CONFORMATION; ISOLATION AND PURIFICATION; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPECIES DIFFERENCE;

ANGIOSPERMS; BENZOFURANS; GLUCOSIDES; GLYCOSIDES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NITRILES; SPECIES SPECIFICITY;

BETULACEAE; BORAGINACEAE; GUAZUMA ULMIFOLIA; MALVACEAE; OSTRYA VIRGINIANA; TIQUILIA CANESCENS; TIQUILIA PLICATA;

EID: 21844470248     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2005.02.021     Document Type: Article

References (85)

1. K. Aikman, D. Bergman, J. Ebinger, and D. Seigler Variation of cyanogenesis in some plant species of the Midwestern United States Biochemical Systematics Ecology 24 1996 637 645
2. A. Ballester, A. Verwey, and J.C. Overeem 2-Hydroxyphenyl acetic acid and 2,4-dihydroxyphenyl acetonitrile from Erica scoparia Phytochemistry 14 1975 1667 1668
3. M. Barfield, and B. Chakrabarti Long-range proton spin-spin coupling Chemical Reviews 69 1969 757 778
4. Blessing, R.H., 1989. SORTAV Absorption Correction Data Program.
5. R.H. Blessing An empirical correction for absorption anisotropy Acta Crystallographica A 51 1995 33 37
6. R.H. Blessing Outlier treatment in data merging Journal Applied Crystallography 30 1997 421 426
7. L. Brimer, S.B. Christensen, P. Moelgaard, and F. Nartey Determination of cyanide and cyanogenic compounds by thin-layer chromatography. 1. A densitometric method for quantification of cyanogenic glycosides, employing enzyme preparations (β-glucosidase) from Helix pomatia and picrate-impregnated ion-exchange sheets Journal Agricultural Food Chemistry 31 1983 789 793
8. A.M. Brinker, and D.S. Seigler Methods for the detection and quantitative determination of cyanide in plant materials Phytochemical Bulletin 21 1989 24 31
9. A.M. Brinker, and D.S. Seigler Determination of cyanide and cyanogenic glycosides from plants H.F. Linskens J.F. Jackson Plant toxin analysis 1992 Springer Berlin 359 381
10. C.C. Chen, Y.P. Chen, H.Y. Hsu, H.H. Lee, S. Tani, and A.T. McPhail Bauhinin, a new nitrile glucoside from Bauhinia championii Journal of Natural Products 48 1985 933 937
11. Coll, J., Bowden, B., 1986. The application of vacuum liquid chromatography to the separation of terpene mixtures. Journal of Natural Products 934-936.
12. D. Dwuma-Badu, W.H. Watson, E.M. Gopalkrishna, T.U. Okarter, J.E. Knapp, and D.J. Slatkin Constituents of West African medicinal plants. XVI. Griffonin and griffonilide, novel constituents of Griffonia simplicifolia Lloydia 39 1976 385 390
13. C.A. Elliger, A.C. Waiss Jr., and R.E. Lundin Simmondsin, an unusual 2-cyanomethylenecyclohexyl glucoside from Simmondsia californica Journal of the Chemical Society, Perkin Trans. I 1973 2209 2212
14. C.A. Elliger, A.C. Waiss Jr., and R.E. Lundin Structure and stereochemistry of simmondsin Journal of Organic Chemistry 39 1974 2930 2931
15. F. Feigl, and V. Anger Replacement of benzidine by copper ethylacetoacetate and tetra base as spot-test reagent for hydrogen cyanide and cyanogen Analyst 91 1966 282 284
16. L.H. Fikenscher, and H.W.L. Ruijgrok Cyanogenese bei den Cormophyten. 13. Mitteilung. Die cyanogenen Glucoside von Platanus Sippen Planta Medica 31 1977 290 293
17. L.H. Fikenscher, and R. Hegnauer Die Verbreitung der Blausäure bei den Cormophyten. 17. Mitteilung. Taxiphyllin aus Magnolia sprengeri cv. "Diva" Journal of Natural Products 44 1981 710 712
18. R.D. Gibbs Chemotaxonomy of flowering plants vol. 4 1974 McGill-Queen's University Press Montreal
19. M.S. Gill, A.J. MacLeod, and M. Moreau Volatile components of cocoa with particular reference to glucosinolate products Phytochemistry 23 1984 1937 1942
20. K.E. Glander Habitat description and resource utilization: a preliminary report on mantled howling monkey ecology R.H. Tuttle Socioecology and psychology of primates 1975 Mouton The Hague 37 57
21. H.A. Gleason, and A. Cronquist Illustrated flora of the Northeastern United States and adjacent Canada second ed. 1991 New York Botanical Garden New York
22. R. Hegnauer Chemotaxonomie der Pflanzen vol. 3 1964 Birkhäuser Verlag Basel pp. 300-306
23. R. Hegnauer Chemotaxonomie der Pflanzen vol. 6 1973 Birkhäuser Verlag Basel pp. 467-469
24. R. Hegnauer Die cyanogenen Verbindungen der Liliatae und Magnoliatae: Zur systematischen Bedeutung des Merkmals der Cyanogenese Biochemical Systematics 1 1973 191 197
25. R. Hegnauer Cyanogenic compounds as systematic markers in Tracheophyta Plant Systematics Evolution Suppl. 1 1977 191 209
26. R. Hegnauer Chemotaxonomie der Pflanzen vol. 8 1989 Birkhäuser Verlag Basel p. 67, 152, 699
27. R. Hegnauer, and H.W.L. Ruijgrok Lilaea scilloides und Juncus bulbosus. Zwei neue cyanogene Pflanzen Phytochemistry 10 1971 2121 2124
28. M. Hör, M. Heinrich, and H. Rimpler Proanthocyanidin polymers with antisecretory activity and proanthocyanidin oligomers from Guazuma ulmifolia bark Phytochemistry 42 1996 109 119
29. Jaki, B., Chadwick, L., Seigler, D., Pauli, G., 2003. J-code cracking in the fingerprint dereplication of small molecules. In: Proceedings of SMASH 2003, Verona, Italy, September 2003.
30. D.H. Janzen Costa Rican natural history 1983 University of Chicago Chicago, IL
31. W.S. Judd, C.S. Campbell, E.A. Kellogg, P.F. Stevens, and M.J. Donoghue Plant systematics. A phylogenetic approach second ed. 2002 Sinauer Associates Sunderland, MA
32. Keller, E., 1997. SCHAKAL Graphics Program.
33. M. Lechtenberg, and A. Nahrstedt Cyanogenic glycosides R. Ikan Naturally occurring glycosides 1999 John Wiley Chichester, England 147 191
34. C.H. Mao, and L.J. Anderson Cyanogenesis in Sorghum vulgare: mechanism of the alkaloine hydrolysis of dhurrin Organic Chemistry 30 1965 603
35. Martínez, M., 1969. Plantas Medicinales de Mexico. Ediciones Botas. Mexico, D.F.
36. J.G. Millar Liquid Chromatography J.G. Millar K.F. Haynes Methods in chemical ecology Chemical methods vol. 1 1998 Chapman and Hall New York 38 83
37. Moerman, D.E., 1986. Medicinal Plants of Native America, 2 vols. University of Michigan, Museum of Anthropology, Technical Report 19, Ann Arbor.
38. B.L. Møller, and D.S. Seigler Biosynthesis of cyanogenic glucosides, cyanolipids, and related compounds B.J. Singh Plant amino acids 1999 Marcel Dekker New York 563 609
39. A. Murakami, H. Ohigashi, S. Tanaka, M. Hirota, R. Irie, N. Takeda, A. Tatematsu, and K. Koshimuzu Bitter cyanoglucosides from Lophira alata Phytochemistry 32 1993 1461 1466
40. A. Nahrstedt Triglochinin in Araceen Phytochemistry 14 1975 2627 2628
41. A. Nahrstedt, and S. Limmer Dhurrin, the cyanogenic glucoside of Cercocarpus ledifolius, Rosaceae-Rosoideae Phytochemistry 21 1982 2738
42. A. Nahrstedt, and V. Wray Structural revision of a putative cyanogenic glucoside from Ilex aquifolium Phytochemistry 29 1990 3934 3936
43. A. Nahrstedt, P. Proksch, and E.E. Conn Dhurrin, (-)-catechin, flavonol glycosides and flavones from Chamaebatia foliolosa (Rosaceae) Phytochemistry 26 1987 1546 1547
44. A. Nahrstedt, W. Hösel, and A. Walther Characterization of cyanogenic glucosides and β-glucosidases in Triglochin maritima seedlings Phytochemistry 18 1979 1137 1141
45. A. Nahrstedt, M. Lechtenberg, A. Brinker, D.S. Seigler, and R. Hegnauer 4-Hydroxymandelonitrile glucosides, dhurrin in Suckleya suckleyana and taxiphyllin in Girgensohnia oppositifolia (Chenopodiaceae) Phytochemistry 33 1993 847 850
46. A. Nahrstedt, J. Kant, and W. Hösel Aspects on the biosynthesis of the cyanogenic glucoside triglochinin in Triglochin maritima Planta Medica 40 1984 394 398
47. Nonius, B.V., 1998. COLLECT. Bruker, Delft, Netherlands.
48. Otwinowski, Z., 1997. Denzo-SMN Program.
49. Z. Otwinowski, and W. Minor Processing of X-ray diffraction data collected in oscillation mode Methods in Enzymology 276 1997 307 326
50. Pauli, G.F., 1993. Cardenolide aus Adonis aleppica Boiss. -Isolierung und Strukturaufklärung, PhD Thesis, University of Düsseldorf, Germany.
51. W. Pelletier, H. Chokshi, and H. Desai Separation of diterpenoid alkaloid mixtures using vacuum liquid chromatography Journal of Natural Products 49 1986 892 900
52. Perch Solutions, Perch NMR Software, Kuopio, Finland.
53. F. Petereit, M. Sakar, and A. Nahrstedt A. Flavan-di-O-gallates and further polyphenols from Sedum stoloniferum Pharmazie 53 1998 280 281
54. 1H NMR spectroscopy of tumor-promoting diterpene esters Journal of Natural Products 52 1989 186 190
55. Pittier, H., 1978 (reprinted). Manual de las Plantas Usuales de Venezuela. Fundación Eugenio Mendoza, Caracas.
56. Richardson, A., 1977. Monograph of the genus Tiquilia (Coldenia, sensu lato) Boraginaceae: Ehretioideae. Rhodora 79, 467-572.
57. L. Schnee Plantas Comunes de Venezuela 1973 Universidad Central de Venezuela Maracay
58. D.S. Seigler The naturally occurring cyanogenic glycosides L. Reinhold J.B. Harborne T. Swain Progress in phytochemistry vol. 4 1977 Pergamon Press London 83 120
59. D.S. Seigler, and A.M. Brinker Characterization of cyanogenic glycosides, cyanolipids, nitroglycosides, organic nitro compounds and nitrile glucosides from plants P.M. Dey J.B. Harborne Methods in plant biochemistry Alkaloids, sulphur compounds vol. 8 1993 Academic Press London 51 131
60. D.S. Seigler, G.P. Pauli, A. Nahrstedt, and R. Leen Cyanogenic allosides and glucosides from Passiflora edulis and Carica papaya Phytochemistry 60 2002 873 882
61. D. Sharples, M.S. Spring, and J.R. Stoker Biosynthesis of the major cyanogenic glycoside of Thalictrum aquilegifolium Phytochemistry 11 1972 2999 3002
62. G.M. Sheldrick Phase annealing in SHELX-90: direct methods for larger structures Acta Crystallographica A 46 1990 467 473
63. G.M. Sheldrick SHELXL-97 Structure Refinement Program 1997 Universität Göttingen
64. L.R. Simpol, H. Otsuka, K. Ohtani, R. Kasai, and K. Yamasaki Nitrile glucosidess and rosmarinic acid, the histamine inhibitor from Ehretia philippinensis Phytochemistry 36 1994 91 95
65. A. Sosa, F. Winternitz, R. Wylde, and A.A. Pavia Structure of a cyanoglucoside of Lithospermum purpureo-caeruleum Phytochemistry 16 1977 707 709
66. K. Takahashi, S. Matsuzawa, and M. Takani Studies on the constituents of medicinal plants. XX. The constituent of the vines of Menispermum dauricum Chemical Pharmaceutical Bulletin 26 1978 1677 1681
67. B. Tantisewie, H.W.L. Ruijgrok, and R. Hegnauer Die Verbreitung der Blausäure bei den Cormophyten. 5. Mitteilung: Über cyanogene Verbindungen bei den Parietales und bei einigen weiteren Sippen Pharm. Weekblad 104 1969 1341 1355
68. A.E. Tih, R.G. Tih, B.L. Sondengam, M.T. Martin, and B. Bodo Lanceolins A and B: nitrile glycoside estsers from Lophira lanceolata Phytochemistry 57 1994 971 974
69. L. Tjon Sie Fat Contribution to the knowledge of cyanogenesis in angiosperms. 8th Communication. Cyanogenesis in Commelinaceae Lloydia 41 1978 571 573
70. L. Tjon Sie Fat Contribution to the knowledge of cyanogenesis in angiosperms. 2. Communication. Cyanogenesis in Campanulaceae Proceedings Koninklijke Nederlandse Akademie van Wetenschappen, Ser. C 82 1978 126 131
71. L. Tjon Sie Fat Contribution to the knowledge of cyanogenesis in angiosperms. 11. Communication. Cyanogenesis in some grasses. The genus Cortaderia Proceedings Koninklijke Nederlandse Akademie van Wetenschappen, Ser. C 82 1978 165 170
72. L. Tjon Sie Fat Contribution to the knowledge of cyanogenesis in angiosperms. 7. Communication. Cyanogenesis in some grasses. III Proceedings Koninklijke Nederlandse Akademie van Wetenschappen, Ser. C 82 1978 347 354
73. L. Tjon Sie Fat Contribution to the knowledge of cyanogenesis in angiosperms. 12. Communication. Cyanogenesis in Ranunculaceae Proceedings Koninklijke Nederlandse Akademie van Wetenschappen, Ser. C 82 1979 197 209
74. L. Tjon Sie Fat, and F. van Valen Contribution to the knowledge of cyanogenesis in angiosperms. 5. Communication. Cyanogenesis in some grasses. II Proceedings Koninklijke Nederlandse Akademie van Wetenschappen, Ser. C 82 1978 204 210
75. K. Ueda, K. Yasutomi, and I. Mori Structure of a new cyanoglucoside from Ilex warburgii Loesn Chemistry Letters 1983 149 150
76. F. van Valen Contribution to the knowledge of cyanogenesis in angiosperms. 12. Communication. Cyanogenesis in Boraginaceae Proceedings Koninklijke Nederlandse Akademie van Wetenschappen, Ser. C. 82 1978 171 176
77. F. van Valen Contribution to the knowledge of cyanogenesis in angiosperms. 6. Communication. Cyanogenesis in Trochodendron aralioides Sieb. and Zucc Proceedings Koninklijke Nederlandse Akademie van Wetenschappen, Ser. C 81 1978 198 203
78. F. van Valen Contribution to the knowledge of cyanogenesis in angiosperms. 6. Communication. Cyanogenesis in some Magnoliidae Proceedings Koninklijke Nederlandse Akademie van Wetenschappen, Ser. C. 81 1978 355 362
79. F. van Valen Contribution to the knowledge of cyanogenesis in angiosperms. 10. Communication. Cyanogenesis in Euphorbiaceae Planta Medica 34 1978 408 413
80. F. van Valen Contribution to the knowledge of cyanogenesis in angiosperms. 8. Communication. Cyanogenesis in Papaverales Proceedings Koninklijke Nederlandse Akademie van Wetenschappen, Ser. C. 81 1978 492 499
81. vanValkenburg, J.L.C.H., Bunyaphrapha, N. (Eds.), 2001. Medicinal and poisonous plants 2. No. 12. Plant Resources of Southeast Asia. Backhuys Publishers, Leiden, pp. 286-288.
82. M. Veit, and G.F. Pauli Major flavonoids from Arabidopsis thaliana leaves Journal of Natural Products 62 1999 1301 1303
83. H. Wagner, S. Bladt, and E.M. Zgainski Plant drug analysis 1984 Springer Verlag Berlin
84. M. Willems A cyanogenic glucoside from Ilex aquifolium Phytochemistry 27 1988 1852 1853
85. J. Wu, E.H. Fairchild, J.L. Beal, T. Tomimatsu, and R.W. Doskotch Lithospermoside and dasycarponin, cyanoglucosides from Thalictrum Journal of Natural Products 42 1979 500 511