Retrobiosynthetic study of salicylic acid in Catharanthus roseus cell suspension cultures
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1 Retrobiosynthetic study of salicylic acid in Catharanthus roseus cell suspension cultures
2 Natali Rianika Mustafa Retrobiosynthetic study of salicylic acid in Catharanthus roseus cell suspension cultures. ISBN Printed by PrintPartners Ipskamp B. V., Amsterdam, The Netherlands Cover: Catharanthus roseus (artist: Kathleen O Ryan; source: Australian National Botanic Gardens).
3 Retrobiosynthetic study of salicylic acid in Catharanthus roseus cell suspension cultures PROEFSCHRIFT ter verkrijging van de graad van Doctor aan de Universiteit Leiden, op gezag van Rector Magnificus prof. mr. P. F. van der Heijden, volgens besluit van het College voor Promoties te verdedigen op woensdag 23 mei 2007 klokke uur door Natali Rianika Mustafa geboren te Palembang (Indonesia) in 1964
4 Promotiecommissie Promotor Prof. dr. R. Verpoorte Referent Prof. dr. J-P. Métraux (Université de Fribourg, Switzerland) Overige Leden Prof. dr. P. J. J. Hooykaas Prof. dr. C. A. M. J. J. van den Hondel Dr. H. K. Kim Dr. Y. H. Choi ii
5 Contents Abbreviations iv Chapter 1 General Introduction 1 Chapter 2 Chorismate-derived C6C1 compounds in plant (review) 5 Chapter 3 Phenolic compounds in Catharanthus roseus (review) 13 Chapter 4 Salicylic acid production in Catharanthus roseus cell suspension cultures elicited by Pythium aphanidermatum extract 35 Chapter 5 Single step purification of salicylic acid from Catharanthus roseus cell culture (plant material) by anion exchange for NMR analysis 47 Chapter 6 A retrobiosynthetic study of salicylic acid production in Catharanthus roseus cell suspension cultures 61 Chapter 7 Metabolic profiling of Catharanthus roseus cell suspension cultures elicited with salicylic acid 87 Summary 109 Samenvatting 113 References 118 Curriculum Vitae 127 Acknowledgements 128 iii
6 Abbreviations AcCN ADP AQ AS ATP BA C4H CC CM COSY CPL 2,4-D DAD = PDA 2,3-DHBA 2,3-DHBAG DMAPP DW DXR DXS E4P EMP EtOAc ESI FAB FW GA GABA GC G10H HBA HMBC HMGR HMQC HR IAA ICS acetonitrile adenosine diphosphate anthraquinones anthranilate synthase adenosine triphosphate benzoic acid cinnamate 4-hydroxylase column chromatography chorismate mutase correlated spectroscopy chorismate pyruvate-lyase 2,4-dichlorophenoxyacetic acid photodiode array detector 2,3-dihydroxybenzoic acid 2,3-dihydroxybenzoic acid glucoside dimethylallyl diphosphate dry weight 1-deoxy-D-xylulose 5-phosphate reductoisomerase 1-deoxy-D-xylulose 5-phosphate synthase erythrose-4-phosphate Embden-Meyerhof-Parnas ethylacetate electrospray ionization fast atom bombardment fresh weight gallic acid -amino butyric acid gas chromatography geraniol 10-hydroxylase hydroxybenzoic acid heteronuclear multiple bond correlation 3-hydroxy-3-methylglutaryl-CoA reductase heteronuclear multiple-quantum coherence hypersensitive reaction indole-3-acetic acid isochorismate synthase iv
7 IEC IPL IPP ISR JA MECS MeJA MeOH MEP MS M&S NAA NMR OMT ORCA PAL PC PCA PEP 3PGAL PP-ED PR protein RP-HPLC RT-PCR SA SAG SAR SH STR TDC TIA TLC TSP UV ion exchange chromatography isochorismate pyruvate-lyase isopentenyl diphosphate induced systemic resistance jasmonate 2C-methyl-D-erythritol 2,4-cyclodiphosphate synthase methyl jasmonate methanol methyl-erythritol phosphate mass spectrometry Murashige & Skoog 1-naphtaleneacetic acid nuclear magnetic resonance O-methyltransferase octadecanoid responsive Catharanthus AP2-domain phenylalanine ammonia-lyase paper chromatography principal component analysis phosphoenolpyruvate glyceraldehyde-3-phosphate pentose phosphate-entner-doudoroff pathogenesis related protein reversed phase high performance liquid chromatography reversed transcription-polymerase chain reaction salicylic acid salicylic acid glucoside systemic acquired resistance Schenk and Hildebrandt strictosidine synthase tryptophan decarboxylase terpenoid indole alkaloid thin layer chromatography trimethylsilyl propionic acid Na salt ultra violet v
8 vi
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