Methyl Jasmonate application

Methyl Jasmonate Application to Mature Trees in the Field. 6... 

It is well established that 18 2 and 18 3 are the precursors of and C, aldehydes and alcohols by exogenous application of 18 2 or 18 3 and radiolabelled precursors, e.g. [93]. As for the hexyl and hexenyl esters, it is not clear if hexyl or hexenyl moieties of esters solely originate from C, aldehydes or alcohols. Incubation of apple fruits with hexanal or hexanol resulted in an increase in the formation of hexyl esters, e.g. [94], but increased levels of these esters at the ripe stage of apple fruits were much larger than the endogenous levels of aldehydes and alcohols [97]. Interestingly, methyl jasmonate application stimulated ester formation of the pre-climacteric apples, but had no effect on the ester formation of the post-climacteric fruits [17] however, it inhibited the hexyl ester formation in apples stored in a controlled atmosphere [96]. Fan et al. [17] speculated that the inhibitory effect found in the last report was owing to the toxic level of methyl jasmonate used. 

Application of these methods toward the preparation of natural products, such as (—)-methylenolactocin (41) or CK-methyl jasmonate (42), has been accomplished" (Scheme 17). 

Several applications in total syntheses exemplify the value of this methodology 11-oxoequiienin methyl ether (101 Scheme 38),105 107 (+)-a-cuparenone,109 (-)-podorhizon,112 (-)-methyl jasmonate (102 Scheme 39),114 (+)-estrone methyl ether,116 and the so called (+)-A-factor (103 Scheme 40)117 were all prepared in high enantiomeric purity. Other applications constitute preparations of 2-alkylchro-man-4-ones,118 and of 3-vinylcyclopentanones, highly valuable intermediates for steroid total synthesis.106,107... 

Application of Volatile Methyl Jasmonate to Headspace Flow. 50... 

A significant contribution was made to the science of plant cell culture production of paditaxel. Methyl jasmonate solutions that had been pipetted into cell suspension cultures caused transient increases in paditaxel production [27]. This was the first report of modeling that indicated ethylene and methyl jasmonate may participate in cross-talk signal transduction in plants. Other papers have subsequently appeared which demonstrate enhancement of paditaxel productivity by the application of methyl jasmonate to several Taxus species [87,88]. 

Scheme 5.43 illustrates three applications of this methodology to total synthesis. The first exeunple is taken from Posner s synthesis of estrone and estradiol [211], the second from Posner s synthesis of methyl jasmonate [212], and the third from Holton s synthesis of aphidicolin [213]. The latter is particularly noteworthy in that two contiguous quaternary centers are created in the asymmetric addition with excellent selectivity. In the estrone synthesis, the chirality sense of the product is consistent with the nonchelate model, but the other two examples adhere to a chelate model. Note that the difference is the degree of substitution at the a-position of the enolate. 

Scheme 5.43. Applications of sulfoxide Michael additions in natural product synthesis (a) estrone [and estradiol] [211], (b) methyl jasmonate [212], (c) aphidicolin [213], Stereocenters formed in the Michael addition are indicated ( ).

Wang, S.Y, and Zheng, W. Preharvest application of methyl jasmonate increases fruit quality and antioxidant capacity in raspberries. Int. J. Food Sci. Technol. 40, 187-195, 2005. 

Fig. 1.1 Induced anatomical defense responses in Norway spruce. (A, B) Formation of a ring of new, traumatic resin ducts (TD, arrowheads) in the xylem of 2-year-old Norway spruce saplings after application of methyl jasmonate. A large cortical resin duct (CD) can be observed in the phloem, but these ducts do not appear to respond to methyl jasmonate treatment. (C) Normal phloem and sapwood anatomy of an older tree, with concentric rings of polyphenolic parenchyma cells (PP) in the phloem above the cambium (X) and normal wood below. (D) After treatment with methyl jasmonate or fungal infection the PP cells increase greatly in size and traumatic resin ducts (arrowheads) forms in the wood.

Fig. 1.2 External resin flow on a ca. 30-year-old Norway spruce clone after application of methyl jasmonate (100 mM in 0.1% Tween 20) and subsequent inoculation with the blue stain fungus Ceratocystis polonica.

FRANCESCHI, V.R., KREKLING, T., CHRISTIANSEN, E., Application of methyl jasmonate on Picea abies (Pinaceae) stems induces defense-related responses in phloem and xylem., Amer. J. Bot., 2002, 89, 578-586. 

When methyl jasmonate was applied to the surface of tomato plants, the synthesis of a defensive proteinase inhibitor protein was induced, not only in the plant to which the application was made but also in nearby plants. In subsequent studies, this compound was shown to have a similar effect with plants of other families as well (Farmer and Ryan, 1990 Pearce et al., 1991). In a series of experiments, it was demonstrated that methyl jasmonate can be a component of interplant communication systems. Octadecanoid precursors of jasmonic acid were able to activate the synthesis of wound-inducible proteinase inhibitors (Crombie and Mistry, 1991 Farmer and Ryan, 1992). Jasmonic acid is a signal transducer in elicitor-induced plant cultures of Rauvolfia canescens and Eschscholtzia californica. Tissue cultures of 36 species of plants could be induced to accumulate second-... 

This isolated example which echoes the hydrazone work of Enders ( SAMP and RAMP ) no doubt illustrates a more widely applicable principle. Closely related organotin enamines afford the same product (172) with acrylates but usually in poorer chemical and optical yields.A first example of an asymmetric additive Pummerer rearrangement, (173)— (174), an uncommon reaction in its racemic form, is featured in a new route to the 6-keto-ester, (-)-methyl jasmonate (175), having ca. 20% enantiomeric purity (Scheme 13). 

Among the above-mentioned changes, application of exogenous methyl jasmonate has been shown to stimulate ethylene formation [15-17], carotene synthesis [18] and chlorophyll degradation [15,18] in tomato and/or apple fruits. In ripening tomato fruits, methyl jasmonate also increased the level of the precursor free 18 3 as well as aromatic compounds [19]. Methyl jasmonate is reported to have... 

As mentioned in ChaJ>ter 7, accumulation of many secondary products is stimulated by application of exogenous jasmonic acid/methyl jasmonate or related compounds, wounding or herbivory through the signal cascades in which jasmonins are involved. It may be repetitive to mention the effects of jasmonins on... 

Various biotic and abiotic elicitors have been used to increase colchicine production. Application of methyl jasmonate as a biotic elicitor in the media showed increase in growth of the root cultures of Gloriosa superba. Higher concentration of methyl jasmonate decreased growth but enhanced intracellular colchicine content of the root cultures. However, such treatments with methyl jasmonate did not release colchicine into the medium [22],... 

Activity Via the gas phase [ 10 nL ( )-( 1 )/L] it is a potent inducer of proteinase-inhibitor proteins in some species of Solanaceae and Fabaceae . After uptake in the cells it is presumably rapidly hydrolysed to jas-monic acid [C,2H,g03, Mr 210.27, viscous oil, bp. 125 °C (0.13 Pa)], a ubiquitous, intracellular, plant signal substance which stimulates the synthesis of special proteins and induces the plant s defensive reaction via a gene activation . De novo synthesis of (3/f,75)-(-t)-jasmonic acid and an increase in the intracellular concentration of (3/f,75)-(-F)-jasmonic acid from 1-10 ng/g (dry weight) by one to three orders of magnitude occur within a few minutes, e.g., after contact with microbial cell wallswounding, and in shoot spiralization Exogenous application of (methyl)jas-... 

Jasmonic acid (JA) and its methyl ester (MJA) are important members of the family of natural jasmonates. Exogenously adding MJA was shown to increase the production of secondary metabolites in a variety of plant species. Some synthetic elicitors have also been proven to be too. We describe a series of synthetic cell culture elicitors in Chapter 4, including MJA derivatives and benzothiadiazole (BTH) derivatives. Some of them display more potent activity in Taxus chinensis cell culture and Panax notoginseng cell culture than MJA, which reflects the full application of chemical bioengineering in plant cell culture. 

Filella, I., Penuelas, J., Llusia, J. (2006) Dynamics of the enhanced emissions of monoterpenes and methyl salicylate, and decreased uptake of formaldehyde, by Quercus ilex leaves after application of jasmonic acid. The New Phytologist, 169,135-144. 

Another useful reaction of these complexes is alkene insertion. This works well with electron-poor alkenes and may be drawn as a Michael addition. One application is in the synthesis of the perfumery compound, CM-jasmone 4.205 (Scheme 4.73). The initial acyl iron complex reacted with methyl vinyl ketone to give a 1,4-diketone 4.204, which underwent a subsequent intramolecular aldol reaction on treatment with a base. 

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