Structure-activity analyses reveal the existence of two separate groups of active octadecanoids in elicitation of the tendril-coiling response of Bryonia dioica Jacq.

Planta

Volumn 207, Issue 3, 1999, Pages 470-479

  Blechert, S ^a   Bockelmann, C ^b   Fusslein M ^a   Schrader, T V ^a   Stelmach, B ^b   Niesel, U ^b   Weiler, E W ^b  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

^b RUHR UNIVERSITY BOCHUM   (Germany)

Author keywords

Bryonia; Jasmonate analogs; Jasmonate bioassay; Octadecanoids; Tendril coiling

Indexed keywords

12 OXO PHYTODIENOIC ACID; 3 OXO 2 ( 2' PENTENYL)CYCLOPENTANE 1 OCTANOIC ACID; BIOASSAY; CHEMICAL ANALYSIS; CORONAFACIC ACID; CORONATINE; JASMONIC ACID; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION; TENDRIL COILING;

BRYONIA DIOICA;

EID: 0032917707     PISSN: 00320935     EISSN: None     Source Type: Journal    
DOI: 10.1007/s004250050506     Document Type: Article

References (41)

1. Blechert S, Brodschelm W, Hölder S, Kammerer L, Kutchan TM, Mueller MJ, Xia Z-Q, Zenk MH (1995) The octadecanoic pathway: Signal molecules for the regulation of secondary pathways. Proc Natl Acad Sci USA 92: 4099-4105
2. Blechert S, Bockelmann C, Brümmer O, Füsslein M, Gundlach H, Haider G, Hölder S, Kutchan TM, Weiler EW, Zenk MH (1997) Structural separation of biological activities of jasmonates and related compounds. J Chem Soc Perkin Trans 1: 3549-3559
3. Brümmer O, Rückert A, Blechert S (1997) Olefin cross-metathesis with monosubstituted olefins. Chem Eur J 3: 441-446
4. Creelman RA, Mullet JE (1997) Biosynthesis and action of jasmonates in plants. Annu Rev Plant Physiol Plant Mol Biol 48: 355-381
5. Ehret R, Schab J, Weiler EW (1994) Lipoxygenases in Bryonia dioica Jacq. tendrils and cell cultures. J Plant Physiol 144: 175-182
6. Engelberth J, Wanner G, Groth B, Weiler EW (1995) Functional anatomy of the mechanoreceptor cells in tendrils of Bryonia dioica Jacq. Planta 196: 539-550
7. Falkenstein E, Groth B, Mithöfer A, Weiler EW (1991) Methyljasmonate and α-linolenic acid are potent inducers of tendril coiling. Planta 185: 316-322
8. Farmer EE, Ryan CA (1990) Interplant communication: airborne methyl jasmonate induces synthesis of proteinase inhibitors in plant leaves. Proc Natl Acad Sci USA 87: 7713-7716
9. Greulich F, Yoshihara T, Toshima H, Ichihara A (1993) Coronatine, a bacterial toxin, affects the regulation of the ethylene biosynthesis in the same way as methyl (+)-epijasmonate. XV Int Bot Congress, Yokohama, Abstr 4154 1: 388
10. Gundlach H, Müller MJ, Kutchan TM, Zenk MH (1992) Jasmonic acid is a signal transducer in elicitor-induced plant cell cultures. Proc Natl Acad Sci USA 89: 2389-2393
11. Holbrook L, Tung P, Ward K, Reid DM, Abrams S, Lamb N, Quail JW, Moloney MM (1997) Importance of the chiral centers of jasmonic acid in the responses of plants - activities and antagonism between natural and synthetic analogs. Plant Physiol 114: 419-428
12. Hölder S, Blechert S (1996) A concise synthesis of coronafacic acid via ring closing olefin metathesis. Synlett 505-506
13. Ishikawa A, Yoshihara T, Nakamura K (1994) Structure-activity relationships of jasmonates in the induction of expression of two proteinase inhibitor genes of potato. Biosci Biotechnol Biochem 58: 544-547
14. Kaiser I, Engelberth J, Groth B, Weiler EW (1994) Touch- and methyl jasmonate-induced lignification in tendrils of Bryonia dioica Jacq. Bot Acta 107: 24-29
15. Kiyota H, Saitoh M, Oritani T, Yoshihara T (1996) Synthesis and potato tuber-inducing activity of methyl 5′,5′,5′-trifluorojasmonate. Phytochemistry 42: 1259-1262
16. Klüsener B, Boheim G, Liß H, Engelberth J, Weiler EW (1995) Gadolinium-sensitive, voltage-dependent calcium release channels in the endoplasmic reticulum of a higher plant mechanoreceptor organ. EMBO J 14: 2708-2714
17. Koda Y, Kikuta Y, Kitahara T, Nishi T, Mori K (1992) Comparisons of various biological activities of stereoisomers of methyl jasmonate. Phytochemistry 31: 1111-1114
18. Koda Y (1997) Possible involvement of jasmonates in various morphogenic events. Physiol Plant 100: 639-646
19. Krumm T, Bandemer K, Boland W (1995) Induction of volatile biosynthesis in the Lima bean (Phaseolus lunatus) by leucine- and isoleucine conjugates of 1-oxo- and 1-hydroxyindan-4-carboxylic acid: evidence for amino acid conjugates of jasmonic acid as intermediates in the octadecanoid signalling pathway. FEBS Lett 377: 523-529
20. Krumm T, Boland W (1996) Leucine and isoleucine conjugales of 1-oxo-2,3-dihydro-indene-4-carboxylic acid: mimics of jasmonate type signals and the phytotoxin coronatine. Molecules 1: 23-26
21. Laudert D, Hennig P, Stelmach BA, Müller A, Andert L, Weiler EW (1997) Analysis of 12-oxo-phytodienoic acid enantiomers in biological samples by capillary gas chromatography-mass spectrometry using cyclodextrin stationary phases. Anal Biochem 246: 211-217
22. Laudert D, Weiler EW (1998) Allene oxide synthase: a major control point in Arabidopsis thaliana octadecanoid signalling. Plant J 15: 675-684
23. Nüske J, Bublitz F (1993) In vitro coronatine production by several Pseudomonas syringae pv. glycinea isolates. J Basic Microbiol 33: 241-246
24. Parchmann S, Gundlach H, Mueller MJ (1997) Induction of 12-oxo-phytodienoic acid in wounded plants and elicited plant cell cultures. Plant Physiol 115: 1057-1064
25. Quinkert G, Adam F, Dürner G (1982) Asymmetrische Synthese von Methyljasmonat. Angew Chem 94: 866-867
26. Sembdner G, Parthier B (1993) The biochemistry and the physiological and molecular actions of jasmonates. Annu Rev Plant Physiol Plant Mol Biol 44: 569-589
27. Stelmach BA, Müller A, Hennig P, Laudert D, Andert L, Weiler EW (1998) Quantitation of the octadecanoid 12-oxo-phytodienoic acid, a signalling compound in mechanotransduction. Phytochemistry 47: 539-546
28. Taapken T, Blechert S, Weiler EW, Zenk MH (1994) Stereoselective synthesis of 7-substituted jasmonic acid derivatives and investigation of their biological activity. J Chem Soc Perkin Trans I: 1439-1440
29. Tamogami S, Rakwal R, Kodama O (1997) Phytoalexin production by amino acid conjugates of jasmonic acid through induction of naringenin-7-O-methyltransferase, a key enzyme on phytoalexin biosynthesis in rice (Oryza sativa L.). FEBS Lett 401: 239-242
30. Vaughan JR (1951) Acylalkylcarbonates as acylating agents for the synthesis of peptides. J Am Chem Soc 73: 3547
31. Vick BA, Zimmerman DC (1984) Biosynthesis of jasmonic acid by several plant species. Plant Physiol 75: 458-461
32. Ward JL, Beale MH (1993) Synthesis and biological activity of stereochemically locked derivatives of jasmonic acid. J Chem Soc Perkin Trans I: 2379-2381
33. Ward JL, Gaskin P, Beale MH, Sessions R, Koda Y, Wasternack C (1997) Molecular modelling, synthesis and biological activity of methyl 3-methyljasmonate and related derivatives. Tetrahedron 53: 8181-8194
34. Wasternack C, Parthier B (1997) Jasmonate-signalled plant gene expression. Trends Plant Sci 2: 302-307
35. Weber H, Vick BA, Farmer EE (1997) Dinor-oxo-phytodienoic acid: a new hexadecanoid signal in the jasmonate family. Proc Natl Acad Sci USA 94: 10473-10478
36. Weiler EW, Albrecht T, Groth B, Xia Z-Q, Luxem M, Liss H, Andert L, Spengler P (1993) Evidence for the involvement of jasmonates and their octadecanoid precursors in the tendril coiling response of Bryonia dioica. Phytochemistry 32: 591-600
37. Weiler EW, Kutchan TM, Gorba T, Brodschelm W, Niesel U, Bublitz F (1994) The Pseudomonas phytotoxin coronatine mimics octadecanoid signalling molecules of higher plants. FEBS 345: 9-13
38. Weiler EW (1997) Octadecanoid-mediated signal transduction in higher plants. Naturwissenschaften 84: 340-349
39. Yamane H, Sugawara J, Suzuki Y, Shimamura E, Takahashi N (1980) Syntheses of jasmonic acid related compounds and their structure-activity relationships on the growth of rice seedlings. Agric Biol Chem 44: 2857-2864
40. Yoshihara T, Orner E-S, A., Koshino H, Sakamura S, Kikuta Y, Koda Y (1989) Structure of a tuber-inducing stimulus from potato leaves (Solanum tuberosum L.). Agric Biol Chem 53: 2835-2837
41. Zhang Z-P, Krumm T, Baldwin IT (1997) Structural requirements of jasmonates and mimics for nicotine induction in Nicotiana sylvestris. J Chem Ecol 23: 2777-2789