Jasmonic acid

In fact, we observed the ability of cationic PO (pi 9.3) to bind with the purified cell walls of this pathogen (Fig. 8, A). This isoform was activated in the infected plants and under the influence of the stress hormone jasmonic acid, both individually and in combination with salicylic acid. 

Egg-deposition also can induce the host plant to emit volatiles that attract egg parasitoids. For example, egg deposition by the elm leaf beetle (Xantho-galeruca luteola) causes its host plant, the field elm (Ulmus minor), to release a blend of mostly terpenoids that attract the egg parasitoid Oomyzus galleru-cae (Eulophidae) [ 86]. Although the specific compounds that initiate the volatile emission and that attract the egg parasitoid are unknown, the host plant response can be induced with jasmonic acid. 

Exposure to volatile stress signals such as ethylene and jasmonic acid can induce the synthesis and accumulation of high levels of phenolic compounds. The effect is not readily apparent because the accumulated phenolic compounds remain sequestered in organelles within the induced cells. However, increased membrane permeability resulting from even a minor injury or stress can result in levels of discoloration that are abnormally high for that cultivar. 

Several papers have reported that, during germination, new LOXs are synthesized in the seedling and the cotyledons the LOX mRNAs synthesized during germination can also be found in the mature plant. Their levels were increased by the application of abscisic acid and jasmonic acid, or by stress such as wounding, pathogen infection, or water deficit (Porta and Rocha-Sosa 2002). 

DU, L., LYKKESFELDT, J, OLSEN, C.E., HALKIER, B.A., Involvement of cytochrome P450 in oxime production in glucosinolate biosynthesis as demonstrated by an in vitro microsomal enzyme system isolated from jasmonic acid-induced seedlings oiSinapis alba L, Proc. Natl. Acad. Sci. USA, 1995, 92, 12505-12509. 

Blechert and co-workers have also reported the application of cross-metathesis to the synthesis of jasmonic acid derivatives containing modified alkene side chains [28]. Molybdenum or ruthenium catalysed cross-metathesis of acetal 20 with various alkenes gave the desired cross-metathesis products in high yields (Eq. 21) (Table 2). 

The alcohol moiety is produced in a different manner from that of the acid moiety. The alcohol moiety resembles the plant hormone jasmonic acid (JA) (26) generated from linolenoyl moiety of lipids via (13,S )-hydroperoxy-linolenic acid (22), (12.13,S )-epoxylinolenic acid (23), and 12-oxo-cis-10.15-phytodienoic acid (24) by the oxylipin or octadecanoid pathway (Fig. 3) [31]. In fact, 13C was incorporated at pyrethrolone (1) carbon positions that agreed with those predicted to be labeled when the alcohol moiety is produced via the pathway (Fig. 3) [30]. Figure 3 illustrates that m-jasmone (25) is hydroxylated to yield jasmololone (4), which is then dehydrogenated to yield pyrethrolone (5). However, it has not yet been determined if this is actually the case. 

Fig. 3 Biosynthetic pathways to pyrethrins. The identified enzymes involved in biosynthesis are shown in orange. Note that green leaf volatiles and the plant hormone jasmonic acid share the oxylipin pathway. The phosphate moiety is indicated as P ...

Nerolidol synthases of non-homoterpene emitting plants are not shown. JA, jasmonic acid. 

Ament K, Van Schie CC, Bouwmeester HJ, Haring MA, Schumink RC (2006) Induction of a leaf specific geranylgeranyl pyrophosphate synthase and emission of (it -4,8,12-trimethyltrideca-l,3,7,ll-tetraene in tomato are dependent onboth jasmonic acid and salicylic acid signahng pathways. Planta 224 1197-1208... 

Hopke J, Donath J, Blechert S, Boland W (1994) Herbivore-induced volatiles - the emission of acyclic homoterpenes from leaves of Phaseolus lunatus and Zea mays can be triggered by a a-glucosidase and jasmonic acid. FEBS Lett 352 146-150... 

Farmer EE, Ryan CA, Octadecanoid precursors of jasmonic acid activate the synthesis of wound-inducible proteinase inhibitors, Plant G //4 129—134,1992. 

Gundlach H, Muller MJ, Kutchan TM, Zenk MH, Jasmonic acid is a signal transducer in elicitor-induced plant cell cultutes, Proc Natl Acad Sci USA 89 2389-2393, 1992. 

Muellet MJ, Brodschelm W, Spannagl E, Zenk MH, Signaling in the elicitation process is mediated through the octadecanoid pathway leading to jasmonic acid, Proc Natl Acad Sci 175/4 90 7490-7494, 1993. 

Meyer, A., O. Miersch, C. Buttner, W. Dathe, and G. Sembdner. Occurrence of the plant growth regulator jasmonic acid in plants. J Plant Growth Regul 1984 3 1-8. 

Curtin, C., Zhang, W., and Franco, C., Manipulating anthocyanin composition in Vitis vinifera suspension cultures by elicitation with jasmonic acid and light irradiation, Biotechnol Lett., 25, 1131, 2003. 

Munne-Bosch, S., Weiler, E. W., Alegre, L., Muller, M., Duchting, R, Falk, J. (2006). alpha-Tocopherol may influence cellular signaling by modulating jasmonic acid levels in plants. Planta. ... 

In plants the 13-hydroperoxide produced from linolenic acid by lipoxygenase (Sect. 23.4.1.2) can be converted to the allene oxide by allene oxide synthase followed by cyclisation, reduction and -oxidation to form jasmonic acid, an important plant growth factor the corresponding methyl jasmonate is a valuable flavour and fragrance compound that imparts a sweet-floral, jasmine-like note... 

Recently, a patent described the use of Diplodia gossypina ATCC 10936 for the production of natural jasmonic acid [47]. With submerged cultures, up to 1.5 g L" jasmonic acid was obtained after 11 days of incubation the addition of 10-oxo-8-fra s-decenoic acid, a hormone stimulating mycelial growth, proved to be advantageous methyl jasmonate was obtained by autoclaving the... 

Scheme 23.1 a Short-chain flavour acid production from natural alcohols by acetic acid bacteria b Jasmonic acid and methyl jasmonate production with Diploida gossypina... 

Boland, W., , J., Donath, J., Nuske, J. and Bublitz, F. (1995). Jasmonic acid and coronatin induce odor production in plants. Angewandte Chemie International Edition in English 34 1600-1602. 

Dicke, M., Gols, R Ludeking, D. and Posthumus, M. A. (1999). Jasmonic acid and herbivory differentially induce carnivore-attracting plant volatiles in lima bean plants. Journal of Chemical Ecology 25 1907-1922. 

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