Methyl jasmonate, production

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... 

Jasmine. Jasmine is one of the most precious florals used ia perfumery. The concrete of jasmine is produced by hydrocarbon extraction of flowers from Jasminum officinale (var. GrandijJorum). The concrete is then converted to absolute by alcohoHc extraction. It is produced ia many countries, the most important of which is India, followed by Egypt. Jasmine products are rather expensive and are produced ia relatively small amounts compared with other materials. However, jasmine is particularly important ia perfume creation for its great power and aesthetic quaUties. Eour of the principal odor contributors to jasmine are OT-jasmone [488-10-8] (14), methyl jasmonate [91905-974-] (15), benzyl acetate [140-11 ], and iudole [120-72-9] (16). 

Orange Flower. Extraction of freshly picked flowers of the bitter orange tree, dims aurantium (subspecies amard) for the production of concrete is carried out mainly ia Morocco and Tunisia. Most of this material is processed further to give orange flower absolute, one of the most important absolutes used ia perfumes after rose and jasmine. It is highly valued ia perfumery, even when used at low levels, for its long-lasting, rich, warm, yet dehcate and fresh floralcy. The material is a complex mixture, to which methyl anthranilate [134-20-3] linalool (3), methyl jasmonate (15), and iadole (16) are important odor contributors. 

Ketchum, R.E.B., Rithner, C.D., Qiu, D. et al. (2003) Taxus metabolomics methyl jasmonate preferentially induces production of taxoids oxygenated at C-13 in Taxus x media cell cultures. Plant Metabolomics, 62, 901-909. 

Other assays have been used to evaluate the antioxidant activity against H202 of several plant-based products, namely, fruit juices from different cultivars of berries (Wang and Jiao 2000), fractions rich in phenolics isolated from the aqueous by-products obtained during the milling of oil palm fruits (Balasundram and others 2005), cherry laurel fruit and its concentrated juice (Liyana-Pathirana and others 2006), and strawberries and blackberries treated with methyl jasmonate, allyl isothiocyanate, essential oil of Melaleuca alternifolia, and ethanol (Chanjirakul and others 2007). 

Figure 11.3. Effect of natural product treatment (methyl jasmonate MJ 22 ptg/liter, ethanol ETOH 400 pl/liter, methyl jasmonate-ethanol (MJ-ETOH) on (I) total antho-cyanins (mg/100 g FW), (II) total phenols (mg/100 g FW), and (III) antioxidant capacity measured as ORAC (p.mol TE/g FW) of strawberry fruit (cv. Chandler) stored at 5°C. Bars show the final values after treatments. Different letters on top of the bars indicate statistical differences among treatments (p < 0.05).

Arnold TM, TargettNM, Tanner CE, Hatch WI, Ferrari KE (2001) Evidence for methyl jasmonate-induced phlorotannin production in Fucus vesiculosus (Phaeophyceae). J Phycol 37 1026-1029 Bemays EA, Chapman RF (1994) Host-plant selection by phytophagous insects. Chapman Hall, New York... 

Orozco-Cardenas ML, Narvaez-Vasquez J, Ryan CA (2001) Hydrogen peroxide acts as a second messenger for the induction of defense genes in tomato plants in response to wounding, systemin, and methyl jasmonate. Plant Cell 13 179-191 Palmer CJ, Anders TL, Carpenter LJ, Ktipper FC, McFiggans G (2005) Iodine and halocarbon response of Laminaria digitata to oxidative stress and links to atmospheric new particle production. Environ Chem 2 282-290... 

Peruvoside (Fig. 4) is one of the major terpenoids produced by Thevetia peruviana, a small tree commonly used as an ornamental plant. As a cardiac glucoside, this natural product has been used to treat heart failure patients who are allergic to the commercial drug digoxin. Success in obtaining peruvoside from T peruviana was recently reported. Production of approximately 9.0 mg of peruvoside/L was achieved by elicitation of cell cultures with 100-mg/L methyl jasmonate. ... 

Zabala MA, Angarita M, Restrepo JM, Caicedo LA, Perea M. (2009) Elicitation with methyl-jasmonate stimulates peruvoside production in cell suspension cultures of Thevetia peruviana. In Vitro Cell Dev Biol Plant 46 233-238. 

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... 

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

Decarboalkoxylation (9, 283).5 The a-methoxycarbonyl group of 1 is removed cleanly by Lil in boiling eollidine with concomitant hydrolysis of the ester group, possibly via an anhydride. The product (2) is a precursor to methyl jasmonate (3). 

The jasmonates are another class of disubstituted cyclopentanoid natural products very reminiscent of the prostaglandins. To efficiently assemble their main skeleton, Yamamoto and co-workers developed a clever three-component reaction methodology that was demonstrated by the total synthesis of both trans- and cis-methyl jasmonates 36 and 37 (Scheme 12.7) [25],... 

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]. 

Fig. 8. Seven-day ethylene production kinetics by 40 ml Taxus canadensis cultures, which were in 125-ml Erlenmeyer flasks closed with serum caps, following elicitation as follows ( ) methyl jasmonate (100 pM) ( ) control (a) combination of N-acetylchitohexaose (37 mg H) and methyl jasmonate (100 pM) ( ) N-acetylchitohexaose (37 mg H). Reprinted with the permission of Elsevier Science, Ireland Ltd. [103]...

The unsaturated ester (20) can be similarly converted to the endo-alcohol (23), which can be oxidized to the ketone (24 81.9% ee) with an overall yield of 8% (Scheme 6). These products ate potential intermediates for (-)-methyl jasmonate and natural prostaglandins. Here the microorganism is showing good discrimination between the two enantiotopic endo hydrogens on C-2 and C-3. 

Generation of the endocyclic double bond of cyclopentanoids has been accomplished frequently by rDA reaction of the appropriate cyclopentadiene. FVP has been used as the last step of the synthesis of the antibiotic ( )-pentenomycin (53) in 50% yield. " Other cyclopentanoid natural products that are synthesized by procedures based upon a nearly quantitative rDA reaction are jasmone (54) and alkyne (55), a precursor to methyl jasmonate. This same procedure has been applied to the synthesis of intermediates of prostaglandins such as (56). ... 

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