Constitutive polymorphic cyanogenesis in the Australian rainforest tree, Ryparosa kurrangii (Achariaceae)

Phytochemistry

Volumn 68, Issue 15, 2007, Pages 2068-2074

  Webber, Bruce L ^a   Miller, Rebecca E ^a   Woodrow, Ian E ^a  

^a UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

Achariaceae; Constitutive defence; Cyanogenesis; Cyanogenic glycoside; Gynocardin; Polymorphism; Ryparosa kurrangii; Tropical rainforest

Indexed keywords

GLYCOSIDE; NITRILE;

ANGIOSPERM; ARTICLE; AUSTRALIA; GROWTH, DEVELOPMENT AND AGING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; METABOLISM; NUCLEAR MAGNETIC RESONANCE; PLANT LEAF; SOLID PHASE EXTRACTION; TROPIC CLIMATE;

ANGIOSPERMS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLYCOSIDES; NITRILES; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANT LEAVES; QUEENSLAND; SOLID PHASE EXTRACTION; TROPICAL CLIMATE;

ACHARIACEAE; RYPAROSA;

EID: 34447539935     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2007.04.038     Document Type: Article

References (75)

1. Aikman K., Bergman D., Ebinger J., and Seigler D. Variation of cyanogenesis in some plant species of the Midwestern United States. Biochem. Syst. Ecol. 24 (1996) 637-645
2. Alborn H.T., Turlings T.C.J., Jones T.H., Stenhagen G., Loughrin J.H., and Tumlinson J.H. An elicitor of plant volatiles from beet armyworm oral secretion. Science 276 (1997) 945-949
3. Baldwin I.T., Karb M.J., and Ohnmeiss T.E. Allocation of N-15 from nitrate to nicotine - production and turnover of a damage-induced mobile defense. Ecology 75 (1994) 1703-1713
4. Baldwin I.T., and Ohnmeiss T.E. Swords into plowshares? Nicotiana sylvestris does not use nicotine as a nitrogen source under nitrogen-limited growth. Oecologia 98 (1994) 385-392
5. Bazin A., Blaise S., and Cartier D. Polymorphisme de deux mécanismes de défense ches Lotus corniculatus L. (Fabaceae); mise en relation avec des facteurs abiotiques. Acta Botanica Gallica 144 (1997) 433-442
6. Bede J.C., Musser R.O., Felton G.W., and Korth K.L. Caterpillar herbivory and salivary enzymes decrease transcript levels of Medicago truncatula genes encoding early enzymes in terpenoid biosynthesis. Plant Mol. Biol. 60 (2006) 519-531
7. Brinker A.M., and Seigler D.S. Methods for the detection and quantitative determination of cyanide in plant materials. Phytochem. Bull. 21 (1989) 24-31
8. Cabalion P., Fournet A., Mangeney P., and Bouquet A. Recherches chimiques préliminaires sur leas plantes de la république populaire du Congo. Fitoterapia 51 (1980) 89-111
9. Chase M.W., Zmarzty S., Lledo M.D., Wurdack K.J., Swensen S.M., and Fay M.F. When in doubt, put it in Flacourtiaceae: a molecular phylogenetic analysis based on plastidrbcL DNA sequences. Kew Bull. 57 (2002) 141-181
10. Clark D.B., and Clark D.A. Herbivores, herbivory, and plant phenology: patterns and consequences in a tropical rain-forest cycad. In: Price P.W., Lewinsohn T.M., Wilson Fernandes G.W., and Benson W.W. (Eds). Plant-Animal Interactions: Evolutionary Ecology in Tropical and Temperate Regions (1991), John Wiley and Sons, New York 209-225
11. Coburn R.A., and Long Jr. L. Gynocardin. J. Org. Chem. 31 (1966) 4312-4315
12. Coley P.D., and Aide T.M. Comparison of herbivory and plant defenses in temperate and tropical broad-leaved forests. In: Price P.W., Lewinsohn T.M., Fernandes G.W., and Benson W.W. (Eds). Plant-Animal Interactions: Evolutionary Ecology in Tropical and Temperate Regions (1991), John Wiley and Sons, New York 25-49
13. Coley P.D., and Barone J.A. Herbivory and plant defenses in tropical forests. Ann. Rev. Ecol. Syst. 27 (1996) 305-335
14. Cooper-Driver G., and Swain T. Cyanogenic polymorphism in bracken in relation to herbivore predation. Nature 260 (1976) 604
15. Dirzo R., and Harper J.L. Experimental studies on slug-plant interactions. III. Differences in the acceptability of individual plants of Trifolium repens to slugs and snails. J. Ecol. 70 (1982) 101-117
16. Ellis W.D., Keymer R.J., and Jones D.A. The effect of temperature on the polymorphism of cyanogenesis in Lotus corniculatus L. Heredity 38 (1977) 339-347
17. 2 alters the relationship between photosynthesis and defence in cyanogenic Eucalyptus cladocalyx F. Muell. Plant Cell Environ. 21 (1998) 12-22
18. Gleadow R.M., Vecchies A.C., and Woodrow I.E. Cyanogenic Eucalyptus nobilis is polymorphic for both prunasin and specific β-glucosidases. Phytochemistry 63 (2003) 699-704
19. Gleadow R.M., and Woodrow I.E. Temporal and spatial variation of cyanogenic glycosides in Eucalyptus cladocalyx. Tree Physiol. 20 (2000) 591-598
20. Gleadow R.M., and Woodrow I.E. Constraints on effectiveness of cyanogenic glycosides in herbivore defense. J. Chem. Ecol. 28 (2002) 1297-1309
21. Gleadow R.M., and Woodrow I.E. Defense chemistry of cyanogenic Eucalyptus cladocalyx seedlings is affected by water supply. Tree Physiol. 22 (2002) 939-945
22. Goodger J.Q.D., Capon R.J., and Woodrow I.E. Cyanogenic polymorphism in Eucalyptus polyanthemos Schauer subsp. vestita L. Johnson and K. Hill (Myrtaceae). Biochem. Syst. Ecol. 30 (2002) 617-630
23. Greshoff M. Tweede verslag van het onderzoek naar de plantenstoffen van Nederlandsch-Indië. Meded. Lands Plantent. XXV (1898) 1-194
24. Greshoff M. Sur la distribution de l'acide cyanhydrique dans le régne végétal. Bull. Sci. Pharm. 8 (1906) 589-602
25. Greshoff M. Ueber die verteilung der blausäure in dem pflanzenreiche. Arch. Pharm. 244 (1906) 665-672
26. Hayden K.J., and Parker I.M. Plasticity in cyanogenesis of Trifolium repens L.: inducibility, fitness costs and variable expresson. Evol. Ecol. Res. 4 (2002) 155-168
27. Hill E.F., and Henry P.F.P. Cyanide. In: Fairbrother A., Locke L.N., and Hoff G.L. (Eds). Noninfectious Diseases of Wildlife (1996), Iowa State University Press, Ames 219
28. Hruska A.J. Cyanogenic glucosides as defence compounds. A review of the evidence. J. Chem. Ecol. 14 (1988) 2213-2217
29. 13C-NMR of the cyanogenic glycosides. Arch. Pharm. 314 (1981) 609-617
30. Hughes M.A. The cyanogenic polymorphism in Trifolium repens L. (white clover). Heredity 66 (1991) 105-115
31. Jaroszewski J.W., Andersen J.V., and Billeskov I. Plants as a source of chiral cyclopentenes - taraktophyllin and epivolkenin, new cyclopentenoid cyanohydrin glucosides from Flacourtiaceae. Tetrahedron 43 (1987) 2349-2354
32. Jaroszewski J.W., Ekpe P., and Witt M. Cyclopentanoid cyanohydrin glucosides and amides of Lindackeria dentata. Planta Med. 70 (2004) 1001-1003
33. Jaroszewski J.W., and Olafsdottir E.S. Monohydroxylated cyclopentenone cyanohydrin glucosides of Flacourtiaceae. Phytochemistry 26 (1987) 3348-3349
34. Jensen S.R., and Nielsen B.J. Gynocardin in Ceratiosicyos laevis (Achariaceae). Phytochemistry 25 (1986) 2349-2350
35. Jones D.A. Cyanogenesis in animal-plant interactions. In: Evered D., and Harnett S. (Eds). Cyanide Compounds in Biology (1988), John Wiley & Sons, Chichester 151-170
36. Jones D.A. Why are so many food plants cyanogenic?. Phytochemistry 47 (1998) 155-162
37. Kakes P. The function of cyanogenesis in Cassava. Acta Hort. 375 (1994) 79-85
38. Kim H.S., Jeffery G.A., Panke D., Clapp R.C., Coburn R.A., and Long L.J. The X-ray crystallographic determination of the structure of gynocardin. J. Chem. Soc. D: Chem. Comm. 6 (1970) 381b-382b
39. Lambert J.L., Ramasamy J., and Paukstelis J.V. Stable reagents for the colourimetric determination of cyanide by modified König reactions. Anal. Chem. 47 (1975) 916-918
40. Lechtenberg M., and Nahrstedt A. Cyanogenic glycosides. In: Ikan R. (Ed). Naturally Occurring Glycosides (1999), John Wiley & Sons, Chichester 147-191
41. Leitner M., Boland W., and Mithöfer A. Direct and indirect defences induced by piercing-sucking and chewing herbivores in Medicago truncatula. New Phytol. 167 (2005) 597-606
42. McMahon J.M., White W.L.B., and Sayre R.T. Cyanogenesis in cassava (Manihot esculenta Crantz). J. Exp. Bot. 46 (1995) 731-741
43. Miller R.E., Gleadow R.M., and Woodrow I.E. Cyanogenesis in tropical Prunus turneriana: characterisation, variation and response to low light. Funct. Plant Biol. 31 (2004) 491-503
44. Miller R.E., Jensen R., and Woodrow I.E. Frequency of cyanogenesis in tropical rainforests of far north Queensland, Australia. Ann. Bot. 97 (2006) 1017-1044
45. Miller R.E., McConville M.J., and Woodrow I.E. Cyanogenic glycosides from the rare Australian endemic rainforest tree Clerodendrum grayi (Lamiaceae). Phytochemistry 67 (2006) 43-51
46. Møller B.L., and Seigler D.S. Biosynthesis of cyanogenic glycosides, cyanolipids, and related compounds. In: Singh B.K. (Ed). Plant Amino Acids: Biochemistry and Biotechnology (1999), Marcel Dekker, New York 563-609
47. Montgomery R.D. Cyanogens. In: Liener I.E. (Ed). Toxic Constituents of Plant Foodstuffs (1980), Academic Press, London 143-160
48. Nahrstedt A. Cyanogenic compounds as protecting agents for organisms. Plant. Syst. Evol. 150 (1985) 35-47
49. Okolie P.N., and Obasi B.N. Diurnal variation of cyanogenic glucosides, thiocyanate and rhodanese in Cassava. Phytochemistry 33 (1993) 775-778
50. Pederson G.A., Fairbrother T.E., and Greene S.L. Cyanogenesis and climatic relationships in U.S. white clover germplasm collection and core subset. Crop Sci. 36 (1996) 427-433
51. Poulton J.E. Cyanogenesis in plants. Plant Physiol. 94 (1990) 401-405
52. Power F.B., and Barrowcliff M. The constituents of the seeds of Gynocardia odorata. J. Chem. Soc. 87 (1905) 896-900
53. Power F.B., and Gornall F.H. Gynocardin, a new cyanogenetic glucoside. Proc. Chem. Soc. 19 (1904) 137
54. Power F.B., and Lees F.H. Gynocardin, a new cyanogenetic glucoside. J. Chem. Soc. 87 (1905) 349-357
55. Saupe S.G. Cyanogenic compounds and angiosperm phylogeny. In: Young D.A., and Seigler D.S. (Eds). Phytochemistry and Angiosperm Phylogeny (1981), Praeger, New York 80-116
56. Saupe S.G., Seigler D.S., and Escalante-Semerena J.C. Bacterial contamination as a cause of spurious cyanide tests. Phytochemistry 21 (1982) 2111-2112
57. Schappert P.J., and Shore J.S. Cyanogenesis in Turnera ulmifolia L. (Turneraceae). I. Phenotypic distribution and genetic variation for cyanogenesis on Jamaica. Heredity 74 (1995) 392-404
58. Seigler D.S. Isolation and characterization of naturally occurring cyanogenic compounds. Phytochemistry 14 (1975) 9-29
59. Seigler D.S. Plants of the northeastern United States that produce cyanogenic compounds. Econ. Bot. 30 (1976) 395-407
60. Seigler D.S. Cyanide and cyanogenic glycosides. In: Rosenthal G.A., and Berenbaum M.R. (Eds). Herbivores: Their Interactions with Secondary Plant Metabolites. The Chemical Participants vol.1 (1991), Academic Press, San Diego, CA 35-77
61. Seigler D.S., and Spencer K.C. Corrected structures of passicoriacin, epicoriacin and epitetraphyllin B and their distribution in the Flacourtiaceae and Passifloraceae. Phytochemistry 28 (1989) 931-932
62. Seigler D.S., Spencer K.C., Statler W.S., Conn E.E., and Dunn J.E. Tetraphyllin B and Epitetraphyllin B sulphates: novel cyanogenic glucosides from Passiflora caerulea and P. alato-caerulea. Phytochemistry 21 (1982) 2277-2285
63. Solís Neffa V.G., Faloci M.M., and Seijo J.G. Cyanogenesis variation in the Turnera sidoides L. polyploid complex (Turneraceae). Bot. J. Linn. Soc. 141 (2003) 85-94
64. Spencer K.C., and Seigler D.S. Cyanogenic glycosides and the systematics of the Flacourtiaceae. Biochem. Syst. Ecol. 13 (1985) 421-431
65. Spencer K.C., and Seigler D.S. Cyanogenic glycosides of Malesherbia. Biochem. Syst. Ecol. 13 (1985) 23-24
66. Spencer K.C., Seigler D.S., and Fraley S.W. Cyanogenic glycosides of the Turneraceae. Biochem. Syst. Ecol. 13 (1985) 433-435
67. Thomsen K., and Brimer L. Cyanogenic constituents in woody plants in natural lowland rainforest in Costa Rica. Bot. J. Linn. Soc. 124 (1997) 273-294
68. Thorne R.F. The classification and geography of the flowering plants: dicotyledons of the class Angiospermae (subclasses Magnoliidae, Ranunculidae, Caryophyllidae, Dilleniidae, Rosidae, Asteridae, and Lamiidae). Bot. Rev. 66 (2002) 441-647
69. Till I. Variability of expression of cyanogenesis in white clover (Trifolium repens L.). Heredity 59 (1987) 265-271
70. Treub M. Nouvelles recherches sur le rôle de l'acide cyanhydrique dans les plantes vertes II. Ann. Bot. Buitenzorg XXI VI (1907) 79-106
71. VanEtten H.D., Mansfield J.W., Bailey J.A., and Farmer E.E. Two classes of plant antibiotics: phytoalexins versus "phytoanticipins". Plant Cell 6 (1994) 1191-1192
72. Vetter J. Plant cyanogenic glycosides. Toxicon 38 (2000) 11-36
73. Webber, B.L., 2005. Plant-animal interactions and plant defence in the rainforest tree, Ryparosa. PhD Thesis. School of Botany, The University of Melbourne, Australia.
74. Webber B.L., and Woodrow I.E. Cassowary frugivory, seed defleshing and fruit fly infestation influence the transition from seed to seedling in the rare Australian rainforest tree, Ryparosa sp. nov. 1 (Achariaceae). Funct. Plant Biol. 31 (2004) 505-516
75. Webber B.L., and Woodrow I.E. Morphological analysis and a resolution of the Ryparosa javanica species complex (Achariaceae) from Malesian and Australian tropical rainforests. Aust. Syst. Bot. 19 (2006) 541-569