18 THOLL, et al. 45. AGREN, J., SCHEMSKE, D. W. , Outcrossing rate and inbreeding depression in 2 annual monoecious herbs, Begonia hirsuta and B semiovata, Evolution, 1993 , 47, 125- 135. 46. VAN POECKE, R. M. P. , POSTHUMUS, M. A., DICKE, M., Herbivore-induced volatile production by Arahidopsis thaliana leads to attraction of the parasitoid Cotesia ruhecula: Chemical, behavioral, and gene-expression analysis, J. Chem. Ecol., 2001 , 27, 1911 -1928. 47. KOCH, T., KRUMM, T., JUNG, V., ENGELBERTH, J. , BOLAND, W. , Differential induction of plant volatile biosynthesis in the lima bean by early and late intermediates of the octadecanoid-signaling pathway, Plant Physiol. , 1999, 121 , 153-162. 48. MARTIN, D., THOLL, D. , GERSHENZON, J., BOHLMANN, J. , Methyl jasmonate induces traumatic resin ducts, terpenoid resin biosynthesis, and terpenoid accumulation in developing xylem ofNorway spruce stems, Plant Physiol. , 2002, 129, 1003-1018 . 49. CHEN, F. , D' AURIA, J.C., THOLL, D. , ROSS, J.R., GERSHENZON, J. , NOEL, J.P. , PICHERSKY, E., An Arabidopsis thaliana gene for methy1salicy1ate biosynthesis, identified by a biochemical genomics approach, has a role in defense, Plant J., 2003 , 36, 577-588. 50. ENGELBERTH, J., KOCH, T. , SCHULER, G. , BACHMANN, N. , RECHTENBACH, J., BOLAND, W. , Ion channel-forming alamethicin is a potent elicitor of volatile biosynthesis and tendril coiling. Cross talk between jasmonate and salicylate signa li ng in lima bean, Plant Physiol., 200 I, 125, 369-377. 51. SCHIERUP, M.H., MABLE, B.K., AWADALLA, P., CHARLESWORTH, D. , Identification and characterization of a polymorphic receptor kinase gene linked to the self-incompatibility locus of Arabidopsis lyrata, Genetics, 2001 , 158, 387-399. 52. MITCHELL-OLDS, T. , Arahidopsis thaliana and its wild relatives: A model system for ecology and evolution, Trends Ecol. Evol., 200 l, 16, 693-700. 53 . BOHLMANN, J. , MARTIN, D., OLDHAM, N. J. , GERSHENZON, J., Terpenoid secondary metabolism in Arabidopsis thaliana: eDNA cloning, characterization, and functional expression of a synthase, Arch. Biochem. Biophys., 2000,375 , 262-269. 54. FALDT, J. , ARIMURA, G, l., GERSHENZON, J., TAKABAYASHI, J. , BOHLMANN, J., Functional identification of AtTPSOJ as (E)-beta-ocimene synthase: A new monoterpene synthase catalyzing jasmonate- and wound-induced volatile fonnation in Arabidopsis thaliana, Planta, 2003, 216, 745-751. Chapter Two THE BIOCHEMICAL AND MOLECULAR ORIGINS OF ALIPHATIC GLUCOSINOLATE DIVERSITY IN ARABIDOPSIS THALIANA Jim Tokuhisa, * Jan- Will em de Kraker , Susanne Textor, and Jonathan Gershenzon Max Planck Institute for Chemical Ecology Winzwerlaer Str. 10 07745 Jena, Germany * Authorfor correspondence: tokuhisa@ice.mpg.de Introduction ................................................. . ... ... ... . ....... . ........... . Glucosinolate Structure 20 Glucosinolate ·. ·. ·. ·. ·. ·. ·. ·. ·. ·. ·. ·. ·. ·. ·. ·.·. ·. · .·. ·. ·. ·. ·. ·. ·. ·.·. ·. ·. ·. ·.·. ·.·. ·.·.·. ·. ·. ·. ·. ·. ·. ·. ·. · ..... ... 21 Modification of the Amino Acid Precursors 24 20 Formation of Chain Elongated 25 Molecular Basis for Natural Variation in Chain Length . . . . . . . . . . . . . . . . . . . . . 27 Substrate Specificities in the Core Pathway of Glucosinolate Biosynthesis . . . . . . . 28 Cytochromes P450 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 29 Further Steps of the Core Pathway.. ..... ... .. .... . ... .. .. . ......... . ... ... .. .. 29 Further Oxidative Modifications 30 ::.· 31 Other Modifications 32 Summary and Future 33 19