메뉴 건너뛰기




Volumn 206, Issue 3, 1998, Pages 443-451

Chemical diversity and variation of pyrrolizidine alkaloids of the senecionine type: Biological need or coincidence

Author keywords

Biosynthetic transformation; Diversification (chemical); Plant defence (constitutive) Pyrrolizidine alkaloid; Senecio; Senecionine N oxide

Indexed keywords

BIOSYNTHESIS; CHEMICAL ANALYSIS; HYDROXYLATION; OTONECINE; PUTRESCINE; PYRROLIZIDINE ALKALOID; RETRONECINE; SENECIONINE N OXIDE;

EID: 0031664299     PISSN: 00320935     EISSN: None     Source Type: Journal    
DOI: 10.1007/s004250050420     Document Type: Article
Times cited : (128)

References (37)
  • 1
    • 0001461995 scopus 로고
    • Poisonous alkaloids in the body tissue of the garden tiger moth (Arctia caja L.) and the cinnabar moth (Tyria jacobaeae L.) (Lepidopera)
    • de Vries A, Kochva E (eds). Gordon & Breach Sci Pub, New York
    • Aplin RT, Rothschild M (1972) Poisonous alkaloids in the body tissue of the garden tiger moth (Arctia caja L.) and the cinnabar moth (Tyria jacobaeae L.) (Lepidopera). In: de Vries A, Kochva E (eds) Toxins of animal and plant origin, vol 2. Gordon & Breach Sci Pub, New York, pp 579-595
    • (1972) Toxins of Animal and Plant Origin , vol.2 , pp. 579-595
    • Aplin, R.T.1    Rothschild, M.2
  • 2
    • 84940905874 scopus 로고
    • Genetics of secondary metabolism and herbivore resistance in plants
    • Rosenthal A Berenbaum MR (eds). Academic Press, San Diego
    • Berenbaum MR and Zangerl AR (1992) Genetics of secondary metabolism and herbivore resistance in plants. In: Rosenthal A Berenbaum MR (eds) Herbivores: their interactions with secondary plant metabolites, 2nd edn, vol 2. Academic Press, San Diego, pp 415-438
    • (1992) Herbivores: Their Interactions with Secondary Plant Metabolites, 2nd Edn , vol.2 , pp. 415-438
    • Berenbaum, M.R.1    Zangerl, A.R.2
  • 3
    • 0002725353 scopus 로고
    • Capillary gas chromatography/ positive and negative ion chemical ionization mass spectrometry on pyrrolizidine alkaloids of Senecio inaequidens using ammonia and hydroxyl ions as the reagent species
    • Bicchi C, Caniato R, Tabacchi R, Tsoupras G (1989) Capillary gas chromatography/ positive and negative ion chemical ionization mass spectrometry on pyrrolizidine alkaloids of Senecio inaequidens using ammonia and hydroxyl ions as the reagent species. J Nat Prod 52: 32-41
    • (1989) J Nat Prod , vol.52 , pp. 32-41
    • Bicchi, C.1    Caniato, R.2    Tabacchi, R.3    Tsoupras, G.4
  • 4
    • 0001643085 scopus 로고
    • Homospermidine synthase, the first pathway-specific enzyme in pyrrolizidine alkaloids biosynthesis
    • Böttcher F, Adolph RD, Hartmann T (1993) Homospermidine synthase, the first pathway-specific enzyme in pyrrolizidine alkaloids biosynthesis. Photochemistry 32: 679-689
    • (1993) Photochemistry , vol.32 , pp. 679-689
    • Böttcher, F.1    Adolph, R.D.2    Hartmann, T.3
  • 5
    • 0028316283 scopus 로고
    • Biosynthesis of pyrrolizidine alkaloids: Putrescine and spermidine are essential substrates of enzymatic homospermidine formation
    • Böttcher F, Ober D, Hartmann T (1994) Biosynthesis of pyrrolizidine alkaloids: putrescine and spermidine are essential substrates of enzymatic homospermidine formation. Can J Chem 72: 80-85
    • (1994) Can J Chem , vol.72 , pp. 80-85
    • Böttcher, F.1    Ober, D.2    Hartmann, T.3
  • 6
    • 0002517101 scopus 로고
    • Insect pharmacophagously utilizing defensive plant chemicals (pyrrolizidine alkaloids)
    • Boppré M (1986) Insect pharmacophagously utilizing defensive plant chemicals (pyrrolizidine alkaloids). Naturwissenschaften 73: 17-26
    • (1986) Naturwissenschaften , vol.73 , pp. 17-26
    • Boppré, M.1
  • 8
    • 0002237486 scopus 로고
    • Alkaloid N-oxides as transport and vacuolar storage compounds of pyrrolizidine alkaloids in Senecio vulgaris L
    • Ehmke A, von Borstel K, Hartmann T (1988) Alkaloid N-oxides as transport and vacuolar storage compounds of pyrrolizidine alkaloids in Senecio vulgaris L. Planta 176: 83-90
    • (1988) Planta , vol.176 , pp. 83-90
    • Ehmke, A.1    Von Borstel, K.2    Hartmann, T.3
  • 9
    • 84940904043 scopus 로고
    • The evolution of chemical ecology: Contributions from the study of herbivorous insects
    • Rosenthal A, Berenbaum MR (eds). Academic Press, San Diego
    • Feeny P (1992) The evolution of chemical ecology: contributions from the study of herbivorous insects. In: Rosenthal A, Berenbaum MR (eds) Herbivores: their interactions with secondary plant metabolites, 2nd edn, vol 2. Academic Press, San Diego, pp 1-44
    • (1992) Herbivores: Their Interactions with Secondary Plant Metabolites, 2nd Edn , vol.2 , pp. 1-44
    • Feeny, P.1
  • 10
    • 84940917762 scopus 로고
    • Evolution and coevolution of plants and phytophagous arthropods
    • Rosenthal A, Berenbaum MR (eds). Academic Press, San Diego
    • Futuyma DJ, Keese MC (1992) Evolution and coevolution of plants and phytophagous arthropods. In: Rosenthal A, Berenbaum MR (eds) Herbivores: their interactions with secondary plant metabolites, 2nd edn, vol 2. Academic Press, San Diego, pp 439-475
    • (1992) Herbivores: Their Interactions with Secondary Plant Metabolites, 2nd Edn , vol.2 , pp. 439-475
    • Futuyma, D.J.1    Keese, M.C.2
  • 11
    • 85051619153 scopus 로고
    • The cost of plant chemical defence against herbivory: A biochemical perspective
    • Bernays EA (ed). CRS press, Boca Raton
    • Gershenzon J (1994) The cost of plant chemical defence against herbivory: a biochemical perspective. In: Bernays EA (ed) insect-plant interactions, vol 5. CRS press, Boca Raton, pp 105-173
    • (1994) Insect-plant Interactions , vol.5 , pp. 105-173
    • Gershenzon, J.1
  • 12
    • 0030848185 scopus 로고    scopus 로고
    • Biosynthetic incorporation of the aminobutyl group of spermidine into pyrrolizidine alkaloids
    • Graser G, Hartmann T (1997) Biosynthetic incorporation of the aminobutyl group of spermidine into pyrrolizidine alkaloids. Phytochemistry 45: 1591-1595
    • (1997) Phytochemistry , vol.45 , pp. 1591-1595
    • Graser, G.1    Hartmann, T.2
  • 14
    • 0000363630 scopus 로고
    • Biochemistry of the formation of pyrrolizidine alkaloids in root cultures
    • Bajacj YPS (ed). Springer, Berlin
    • Hartmann T (1994) Biochemistry of the formation of pyrrolizidine alkaloids in root cultures. In Bajacj YPS (ed) Biotechnology in agriculture and forestry, vol 26. Springer, Berlin, pp 339-355
    • (1994) Biotechnology in Agriculture and Forestry , vol.26 , pp. 339-355
    • Hartmann, T.1
  • 15
    • 0029784144 scopus 로고    scopus 로고
    • Diversity and variability of plant secondary metabolism: A mechanistic view
    • Hartmann T (1996) Diversity and variability of plant secondary metabolism: a mechanistic view. Entomol Exp Appl 80: 177-188
    • (1996) Entomol Exp Appl , vol.80 , pp. 177-188
    • Hartmann, T.1
  • 16
    • 0000167086 scopus 로고
    • Senecionine N-oxide, the primary product of pyrrolizidine alkaloid biosynthesis in root cultures of Senecio vulgaris
    • Hartmann T, Toppel G (1987) Senecionine N-oxide, the primary product of pyrrolizidine alkaloid biosynthesis in root cultures of Senecio vulgaris. Phytochemistry 26: 1639-1643
    • (1987) Phytochemistry , vol.26 , pp. 1639-1643
    • Hartmann, T.1    Toppel, G.2
  • 17
    • 0000724877 scopus 로고
    • Pyrrolizidine alkaloids: Chemical, biological and chemoecological aspects
    • Pelletier SW (ed). Pergamon Press, Oxford
    • Hartmann T, Witte L (1995) Pyrrolizidine alkaloids: chemical, biological and chemoecological aspects. In Pelletier SW (ed) Alkaloids: chemical and biological perspectives, vol 9. Pergamon Press, Oxford, pp 155-233
    • (1995) Alkaloids: Chemical and Biological Perspectives , vol.9 , pp. 155-233
    • Hartmann, T.1    Witte, L.2
  • 18
    • 85022731989 scopus 로고
    • Organ-specific distribution and accumulation of pyrrolizidine alkaloids during the life history of two annual Senecio species
    • Hartmann T, Zimmer M (1986) Organ-specific distribution and accumulation of pyrrolizidine alkaloids during the life history of two annual Senecio species. J Plant Physiol 122: 67-80
    • (1986) J Plant Physiol , vol.122 , pp. 67-80
    • Hartmann, T.1    Zimmer, M.2
  • 19
    • 0002390706 scopus 로고
    • Metabolic links between the biosynthesis of pyrrolizidine alkaloids and polyamines in root cultures of Senecio vulgaris
    • Hartmann T, Sander H, Adolf RD, Toppel G (1988) Metabolic links between the biosynthesis of pyrrolizidine alkaloids and polyamines in root cultures of Senecio vulgaris. Planta 175: 82- 90
    • (1988) Planta , vol.175 , pp. 82-90
    • Hartmann, T.1    Sander, H.2    Adolf, R.D.3    Toppel, G.4
  • 20
    • 34249969791 scopus 로고
    • Sites of synthesis, translocation and accumulation of pyrrolizidine alkaloid N-oxides in Senecio vulgaris
    • Hartmann T, Ehmke A, Eilert U, von Borstel K, Theuring C (1989) Sites of synthesis, translocation and accumulation of pyrrolizidine alkaloid N-oxides in Senecio vulgaris. Planta 177: 98-107
    • (1989) Planta , vol.177 , pp. 98-107
    • Hartmann, T.1    Ehmke, A.2    Eilert, U.3    Von Borstel, K.4    Theuring, C.5
  • 22
    • 0001341561 scopus 로고    scopus 로고
    • Plant O-methyltransferase signatures
    • Ibrahim RK (1997) Plant O-methyltransferase signatures. Trends Plant Sci 2: 249-250
    • (1997) Trends Plant Sci , vol.2 , pp. 249-250
    • Ibrahim, R.K.1
  • 23
    • 0026380997 scopus 로고
    • On the evolution of plant secondary chemical diversity
    • Jones CG, Firn RD (1991) On the evolution of plant secondary chemical diversity. Phil Trans R Soc London Ser B 333: 273-280
    • (1991) Phil Trans r Soc London Ser B , vol.333 , pp. 273-280
    • Jones, C.G.1    Firn, R.D.2
  • 24
    • 0343012564 scopus 로고
    • 14C-labelled homospermidines and their incorporation into retronecine
    • 14C-labelled homospermidines and their incorporation into retronecine. J Chem Soc Perkin Trans 1: 819-824
    • (1985) J Chem Soc Perkin Trans , vol.1 , pp. 819-824
    • Khan, H.A.1    Robins, D.J.2
  • 25
    • 0028874083 scopus 로고
    • Alkaloid biosynthesis - The basis for metabolic engineering of medicinal plants
    • Kutchan TM (1995) Alkaloid biosynthesis - the basis for metabolic engineering of medicinal plants. Plant Cell 7: 1059-1070
    • (1995) Plant Cell , vol.7 , pp. 1059-1070
    • Kutchan, T.M.1
  • 26
    • 0030609856 scopus 로고    scopus 로고
    • The two faces of pyrrolizidine alkaloids: The role of the tertiary amine and its N-oxide in chemical defense of insects with acquired plant alkaloids
    • Lindigkeit R, Biller A, Buch M, Schiebel HM, Boppré M, Hartmann T (1997) The two faces of pyrrolizidine alkaloids: the role of the tertiary amine and its N-oxide in chemical defense of insects with acquired plant alkaloids. Eur J Biochem 245: 626-636
    • (1997) Eur J Biochem , vol.245 , pp. 626-636
    • Lindigkeit, R.1    Biller, A.2    Buch, M.3    Schiebel, H.M.4    Boppré, M.5    Hartmann, T.6
  • 27
    • 84982358134 scopus 로고
    • Medium for growth and bioassays with tobacco tissue cultures
    • Murashige T, Skoog F (1962) Medium for growth and bioassays with tobacco tissue cultures. Physiol Plant 15: 473-497
    • (1962) Physiol Plant , vol.15 , pp. 473-497
    • Murashige, T.1    Skoog, F.2
  • 28
    • 0029167813 scopus 로고
    • Relative unpalatability of leaf beetles with either biosynthesized or sequestered chemical defence
    • Rowell-Rahier M, Pasteels JM, Alonso-Mejia A, Brower LP (1995) Relative unpalatability of leaf beetles with either biosynthesized or sequestered chemical defence. Animal Behav 49: 709-714
    • (1995) Animal Behav , vol.49 , pp. 709-714
    • Rowell-Rahier, M.1    Pasteels, J.M.2    Alonso-Mejia, A.3    Brower, L.P.4
  • 29
    • 0002387365 scopus 로고
    • Site of synthesis, metabolism and translocation of senecionine N-oxide in cultures roots of Senecio erucifolius
    • Sander H, Hartmann T (1989) Site of synthesis, metabolism and translocation of senecionine N-oxide in cultures roots of Senecio erucifolius. Plant Cell Tissue and Organ Cult 18: 19-31
    • (1989) Plant Cell Tissue and Organ Cult , vol.18 , pp. 19-31
    • Sander, H.1    Hartmann, T.2
  • 30
    • 0001611244 scopus 로고
    • The strange fate of pyrrolizidine alkaloids
    • Chapman RF, Beranys EA, Stoffolano JG (eds). Springer, New York
    • Schneider D (1987) The strange fate of pyrrolizidine alkaloids. In: Chapman RF, Beranys EA, Stoffolano JG (eds) Perspectives in chemoreception and behavior. Springer, New York, pp 123- 142
    • (1987) Perspectives in Chemoreception and Behavior , pp. 123-142
    • Schneider, D.1
  • 31
    • 0010461496 scopus 로고
    • Alkaloid patterns and biosynthetic capacity of root cultures from some pyrrolizidine alkaloid producing Senecio species
    • Toppel G, Witte L, Riebesehl B, von Borstel K, Hartmann T (1987) Alkaloid patterns and biosynthetic capacity of root cultures from some pyrrolizidine alkaloid producing Senecio species. Plant Cell Rep 6: 466-469
    • (1987) Plant Cell Rep , vol.6 , pp. 466-469
    • Toppel, G.1    Witte, L.2    Riebesehl, B.3    Von Borstel, K.4    Hartmann, T.5
  • 32
    • 0003030122 scopus 로고    scopus 로고
    • Pyrrolizidine alkaloids: Different acquisition and use patterns in Apocynaceae and Solanaceae feeding ithomiine butterflies (Lepidoptera: Nymphalidae)
    • Trigo JR, Brown KS, Witte L, Hartmann T, Ernst L, Barata LES (1996) Pyrrolizidine alkaloids: different acquisition and use patterns in Apocynaceae and Solanaceae feeding ithomiine butterflies (Lepidoptera: Nymphalidae). Biol J Linn Soc 58: 99-123
    • (1996) Biol J Linn Soc , vol.58 , pp. 99-123
    • Trigo, J.R.1    Brown, K.S.2    Witte, L.3    Hartmann, T.4    Ernst, L.5    Barata, L.E.S.6
  • 33
    • 0000300513 scopus 로고
    • Pyrrolizidine alkaloid patterns in populations of Senecio vulgaris, S. vernalis and their hybrids
    • von Borstel K, Witte L. Hartmann T (1989) Pyrrolizidine alkaloid patterns in populations of Senecio vulgaris, S. vernalis and their hybrids. Phytochemistry 28: 1635-1638
    • (1989) Phytochemistry , vol.28 , pp. 1635-1638
    • Borstel, K.1    Witte, L.2    Hartmann, T.3
  • 34
    • 38249005504 scopus 로고
    • Genetic analysis of the concentration of pyrrolizidine alkaloids in Senecio jacobaea
    • Vrieling K, De Vos H, van Wijk CAM (1993) Genetic analysis of the concentration of pyrrolizidine alkaloids in Senecio jacobaea. Phytochemistry 32: 1141-1144
    • (1993) Phytochemistry , vol.32 , pp. 1141-1144
    • Vrieling, K.1    De Vos, H.2    Van Wijk, C.A.M.3
  • 35
    • 0020065292 scopus 로고
    • Reversed-phase ion-pair liquid chromatographic procedure for the simultaneous analysis of S-adenoslylmethionine, its metabolites and the natural polyamines
    • Wagner J, Danzin C, Mamont P (1982) Reversed-phase ion-pair liquid chromatographic procedure for the simultaneous analysis of S-adenoslylmethionine, its metabolites and the natural polyamines. J Chromatogr 227: 349-368
    • (1982) J Chromatogr , vol.227 , pp. 349-368
    • Wagner, J.1    Danzin, C.2    Mamont, P.3
  • 36
    • 0000010139 scopus 로고
    • Chemotypes of two pyrrolizidine alkaloid-containing Senecio species
    • Witte L, Ernst L, Adam H, Hartmann T (1992) Chemotypes of two pyrrolizidine alkaloid-containing Senecio species. Phytochemistry 31: 559-565
    • (1992) Phytochemistry , vol.31 , pp. 559-565
    • Witte, L.1    Ernst, L.2    Adam, H.3    Hartmann, T.4
  • 37
    • 44049111679 scopus 로고
    • Comparative analysis of pyrrolizidine alkaloids from natural sources by gas chromatography-mass spectrometry
    • Witte L, Rubiolo P, Bicchi C, Hartmann T (1993) Comparative analysis of pyrrolizidine alkaloids from natural sources by gas chromatography-mass spectrometry. Phytochemistry 32: 187-
    • (1993) Phytochemistry , vol.32 , pp. 187
    • Witte, L.1    Rubiolo, P.2    Bicchi, C.3    Hartmann, T.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.