Easy Preparation of Methyl 7-<i>epi</i>-Jasmonate and Four Stereoisomers of Methyl Cucurbate, and Assessment of the Stereogenic Effect of Jasmonate on Phytohormonal Activities

Seto, Hideharu; Nomura, Emi; Fujioka, Shozo; Koshino, Hiroyuki; Suenaga, Toshiro; Yoshida, Shigeo

doi:10.1271/bbb.63.361

Cited by 23 publications

(13 citation statements)

References 26 publications

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“…The chemicals synthesis of some isomers of CA has also been reported (Dathe et al 1991;Miersch et al 1999a;Seto et al 1999; and their structurefunction relation in plants has been characterized, suggesting that the essential structural factors of this type of compound pointed to the cis configuration of C-1 and C-2 substituents, the free hydroxyl group at the C-3 position, alkenyl or alkyl group at the C-2 position (Seto et al 1999). Searching the literature no reports of CA synthesis and stereoisomers of this compound by biotransformation could be found and no reports have been found that account for the antitumor effect of CA and its stereoisomers.…”

Section: Biotransformation Experiments and Chemical Analysismentioning

confidence: 99%

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New stereoisomeric derivatives of jasmonic acid generated by biotransformation with the fungus Gibberella fujikuroi affect the viability of human cancer cells

Carvajal¹,

Espinoza²,

Caggia³

et al. 2011

Electro Journal of Biotech

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Background: Several studies have shown that (-)-Jasmonic acid, (+)-7-iso-Jasmonic acid and its methyl ester, methyl jasmonate, have anti-cancer activity in vitro and in vivo, exhibiting selective cytotoxicity towards cancer cells. The degree of activity of these molecules is strongly related to their stereochemistry. The biotransformation of known compounds, natural or synthesized, related to interesting biological activities, generates new molecules displaying new improved properties compared with the original ones, increasing its value and providing new more effective products. Therefore, based on the above rationales and observations, in this work a biotransformation protocol to modify the chemical structure of the plant hormone jasmonic acid by using the fungus Gibberella fujikuroi was established. Results: The three jasmonic acid derivatives obtained, 3(S)-Hydroxy-2(R)-(2Z-pentenyl)-cyclopentane-1(R)-acetic acid (1), 3(R)-Hydroxy-2(R)-(2Z-pentenyl)-cyclopentane-1(R)-acetic acid (2), 3-Hydroxy-2(S)-(2Z-pentenyl)-cyclopentane-1(S)-acetic acid (3), were tested for cell-growth inhibition activity towards the human cancer epithelial cell line, the oral squamous carcinoma cells (KB). The results obtained show that jasmonic acid derivatives (1-3) are active on human cancer cells examined in different concentration ranges, with IC50 value less than of 25 µM. The compound 3, with the same molecular structure of compounds 1 and 2, but with different stereochemistry, was more active confirming that the activity of jasmonate compounds is related to their stereochemistry and to substituents in the cyclopentane ring. In this study, we also tested the potential proapoptotic activity of compound 3, and our data suggest that it, as other jasmonate compounds, is able to trigger apoptotic death in cancer cells. This event may be correlated at an elevation of reactive oxygen species (ROS). Administration of N-acetylcysteine (NAC) prevented compound 3 cytotoxicity. Conclusions: This work shows for the by first time the production of hydroxylated derivatives of JA by biotransformation. The activity observed of these compounds in cancer cells is higher than the observed with JA and is strongly related to its stereochemistry.

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Section: Biotransformation Experiments and Chemical Analysismentioning

confidence: 99%

“…The structural determination of 1, 2 and 3was mainly accomplished by 1 H, 13 C, DEPT-135, gs-2D (HHCOSY, HSQC and HMBC) NMR techniques and compared with those previously reported (Seto et al 1999). …”

Section: Biotransformation Experiments and Chemical Analysismentioning

confidence: 99%

New stereoisomeric derivatives of jasmonic acid generated by biotransformation with the fungus Gibberella fujikuroi affect the viability of human cancer cells

Carvajal¹,

Espinoza²,

Caggia³

et al. 2011

Electro Journal of Biotech

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“…Briefly, 10 mg of trans-d 2 JA-Ile was reduced with NaBH 4 (4 equivalents) in methanol on ice-bath for 2 h. The reaction mixture was acidified with hydrochloric acid (HCl), extracted with chloroform (CHCl 3 ) and concentrated to yield quantitatively 6-epi-7-iso-d 2 CA-Ile (1) and 7-iso-d 2 CA-Ile (2). Non-deuterated compounds 6-epi-7-iso-CA-Ile (1 0 ) and 7-iso-CAIle (2 0 ) were independently prepared from natural 6-epi-7-iso-CA and 7-iso-CA (Seto et al, 1999) and Ile, and the compounds were utilized to identify the peaks 1 and 2 as 6-epi-7-iso-d 2 CA-Ile (1) (t R = 9.5 min) and 7-iso-d 2 CA-Ile (2) (t R = 10.5 min) in Fig. 3A, respectively, by co-injection with LC-MS/MS analysis.…”

Section: Reduction Of Trans-d 2 Ja-ile and Peak Identificationmentioning

confidence: 99%

An in planta technique for cis-/trans-stereochemical analysis of jasmonoyl isoleucine

Tamogami

Agrawal²,

Rakwal

2010

Journal of Plant Physiology

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“…To study the structureactivity relationship of JA analogues, we used racemic mixtures of JA ( Figure 2I; compounds 1 through 9 in Table 1) and dihydrojasmonic acid (DJA; Figure 2II; compounds 10 through 19 in Table 1) that contained less than 5% 3,7-cis-stereoisomers and that were provided by Zeon Corporation (Tokyo, Japan; Fujisawa et al 1999). Stereoisomers of cucurbic acid derivatives (Figure 2III; compounds 20 through 25 in Table 2) were prepared as described (Seto et al 1999).…”

Section: Chemicalsmentioning

confidence: 99%

Cloning of a cDNA-encoding ACC synthase and its mRNA expression during zygotic embryogenesis of chick-pea (Cicer arietinum L.) seeds

et al. 2006

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Plant hormones play many important roles in plant growth and development. We previously tried to control barley (Hordeum vulgare L.) flowering in ear cultures treated with plant hormones and related compounds, and found that anther extrusion from florets was reduced by treatment with 100 ppm methyl jasmonate (MJA). In the present study, we show that 10 ppm MJA also inhibits anther extrusion in barley ear cultures. Spraying field-grown barley ears with MJA clarified the efficacy of this chemical under field conditions, but higher concentrations (100 to 1000 ppm MJA) were required. In addition, we investigated the activity of jasmonic acid (JA) analogues and cucurbic acid analogues in barley ear cultures. Some esters of JA showed similar effects to that of MJA, but effects of 9,10-dihydrojasmonic acid (DJA) and cucurbic acid derivatives were lower than that of MJA. In light of these data, we discuss the structural requirements for increased inhibition of barley anther extrusion.

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Easy Preparation of Methyl 7-epi-Jasmonate and Four Stereoisomers of Methyl Cucurbate, and Assessment of the Stereogenic Effect of Jasmonate on Phytohormonal Activities

Cited by 23 publications

References 26 publications

New stereoisomeric derivatives of jasmonic acid generated by biotransformation with the fungus Gibberella fujikuroi affect the viability of human cancer cells

New stereoisomeric derivatives of jasmonic acid generated by biotransformation with the fungus Gibberella fujikuroi affect the viability of human cancer cells

An in planta technique for cis-/trans-stereochemical analysis of jasmonoyl isoleucine

Cloning of a cDNA-encoding ACC synthase and its mRNA expression during zygotic embryogenesis of chick-pea (Cicer arietinum L.) seeds

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