62653-85-4Relevant academic research and scientific papers
Facile preparation of optically active jasmonates and their biological activities in rice
Miyamoto, Koji,Matsumoto, Tomoharu,Yumoto, Emi,Sakazawa, Tomoko,Yokota, Takao,Yamane, Hisakazu,Uchida, Kenichi
, p. 876 - 881 (2019/06/19)
A facile and efficient method has been developed for the optical resolution of racemic jasmonic acid (JA) on a relatively large scale and was successfully utilized for the preparation of optically pure (+)-JA and (?)-JA. We indicated that (+)-JA has lower growth inhibitory activity than (?)-JA in the rice seedling growth test and confirmed in line with an earlier observation that their respective biologically-active forms, (+)-JA-Ile and (?)-JA-Ile, show comparable inhibitory activities. We compared the metabolism of (+)-JA and (?)-JA into (+)-JA-Ile and (?)-JA-Ile, respectively, in the JA-deficient rice cpm2, and found that the exogenously applied (+)-JA was metabolized to the corresponding Ile conjugate less efficiently as compared with (?)-JA. Such metabolic rate difference may cause a discrepancy between biological potencies of (+)-JA and (?)-JA in rice.
Strategy for synthesis of the isoleucine conjugate of epi-jasmonic acid
Ogawa, Narihito,Kobayashi, Yuichi
body text, p. 7124 - 7127 (2009/04/10)
The TES ether of 2-((1R,2S,3R)-3-hydroxy-2-((Z)-pent-2-enyl)cyclopentyl)acetic acid (5, equal to the reduction product of epi-jasmonic acid) derived from (1R,4S)-4-hydroxycyclopent-2-enyl acetate (19) in 13 steps was activated by using isobutyl chloroformate and was subjected to condensation with isoleucine at room temperature for 48 h. The product was desilylated and oxidized to the isoleucine conjugate of epi-jasmonic acid in 68% yield over three steps. Similarly, allo-isoleucine conjugate of epi-jasmonic acid and three isoleucine conjugates of ent-epi-jasmonic acid, jasmonic acid, and ent-jasmonic acid were synthesized.
Jasmonate biosynthesis in Arabidopsis thaliana requires peroxisomal β-oxidation enzymes - Additional proof by properties of pex6 and aim1
Delker, Carolin,Zolman, Bethany K.,Miersch, Otto,Wasternack, Claus
, p. 1642 - 1650 (2008/02/05)
Jasmonic acid (JA) is an important regulator of plant development and stress responses. Several enzymes involved in the biosynthesis of JA from α-linolenic acid have been characterized. The final biosynthesis steps are the β-oxidation of 12-oxo-phytoenoic
Preparation and biological activity of molecular probes to identify and analyze jasmonic acid-binding proteins
Jikumaru, Yusuke,Asami, Tadao,Seto, Hideharu,Yoshida, Shigeo,Yokoyama, Tadashi,Obara, Naomi,Hasegawa, Morifumi,Kodama, Osamu,Nishiyama, Makoto,Okada, Kazunori,Nojiri, Hideaki,Yamane, Hisakazu
, p. 1461 - 1466 (2007/10/03)
Several types of jasomonic acid (JA) derivatives, including JA-amino acid conjugates, a JA-biotin conjugate, a JA-dexamethasone heterodimer, and a JA-fluoresceine conjugate, were prepared as candidates for molecular probes to identify JA-binding proteins. These JA derivatives, excepting the JA-fluoresceine conjugate, exhibited significant biological activities in a rice seedling assay, a rice phytoalexin-inducing assay, and/or a soybean phenylalanine ammonia-lyase-inducing assay. These JA derivatives could therefore be useful probes for identifying JA-binding proteins. The activity spectra of the prepared compounds were different from each other, suggesting that different types of JA receptors were involved in the perception of JA derivatives in the respective bioassays.
Compositions comprising cyclopentane derivatives and their use
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Page 4, (2008/06/13)
Cosmetic or pharmaceutical compositions comprising compounds of formula (I) and the corresponding salts thereof: in which: —R1 is a radical chosen from —COOR′, —CONR′R″, —CH2OR′, —COR′, —CH2R′, —SO2OR′, —PO3R′R″ and —NHR′, wherein R′ and R,″ which may be identical or different, are chosen from a hydrogen atom and saturated and unsaturated, linear, branched and cyclic hydrocarbon radicals comprising from 1 to 18 carbon-atoms, which are optionally substituted by from 1 to 5 identical or different entities chosen from —OR′″, —OCOR′″, —SR′″, —SCOR′″, NR′″R″″, —NHCOR′″, halogen atoms, —CN, —COOR′″ and —COR′″, wherein R′″ and R″″, which may be identical or different, are chosen from a hydrogen atom, aryl radicals and saturated and unsaturated, linear and branched hydrocarbon radicals comprising from 1 to 4 carbon atoms; —R2 is a radical chosen from linear, branched and cyclic hydrocarbon radicals comprising at least one unsaturation and comprising from 2 to 18 carbon atoms, which are optionally substituted by from 1 to 5 identical or different entities chosen from —OR′″, —OCOR′″, —SR′″, —SCOR′″, NR′″R″″, —NHCOR′″, halogen atoms, —CN, —COOR′″ and —COR′″, wherein R′″ and R″″, which may be identical or different, are chosen from a hydrogen atom, aryl radicals and saturated and unsaturated, linear and branched hydrocarbon radicals comprising from 1 to 4 carbon atoms as well as the use of these compounds, for example, to promote skin desquamation, to stimulate epidermal renewal and/or to combat the signs of skin ageing.
Purification and partial amino acid sequences of an esterase from tomato
Stuhlfelder, Christiane,Lottspeich, Friedrich,Mueller, Martin J.
, p. 233 - 240 (2007/10/03)
Screening of 18 suspension plant cell cultures of taxonomically distant species revealed that a methyl jasmonate hydrolysing enzyme activity (0.21-5.67 pkat/mg) occurs in all species so far analysed. The methyl jasmonate hydrolysing esterase was purified from cell cultures of Lycopersicon esculentum using a five-step procedure including anion-exchange chromatography, gel-filtration and chromatography on hydroxylapatite. The esterase was purified 767-fold to give an almost homogenous protein in a yield of 2.2%. The native enzyme exhibited a Mr of 26 kDa (gel-filtration chromatography), which was similar to the Mr determined by SDS-PAGE and MALDI-TOF analysis (Mr of 28547 kDa). Enzyme kinetics revealed a Km value of 15 μM and a Vmax value of 7.97 nkat/mg, an pH optimum of 9.0 and a temperature optimum of 40 °C. The enzyme also efficiently hydrolyzed methyl esters of abscisic acid, indole-3-acetic acid, and fatty acids. In contrast, methyl esters of salicylic acid, benzoic acid and cinnamic acid were only poor substrates for the enzyme. N-Methylmaleimide, iodacetamide, bestatin and pepstatin (inhibitors of thiol-, metal- and carboxyproteases, respectively) did not inactivate the enzyme while a serine protease inhibitor, phenylmethylsulfonyl fluoride, at a concentration of 5 mM led to irreversible and complete inhibition of enzyme activity. Proteolysis of the pure enzyme with endoproteinase LysC revealed three peptide fragments with 11-14 amino acids. N-Terminal sequencing yielded an additional peptide fragment with 10 amino acids. Sequence alignment of these fragments showed high homologies to certain plant esterases and hydroxynitrile lyases that belong to the α/β hydrolase fold protein superfamily.
Novel three-component coupling using aluminum tris(2,6-diphenylphenoxide) (ATPH): The same synthetic strategy leads to trans- and cis-jasmonates
Saito, Susumu,Yamazaki, Satoko,Yamamoto, Hisashi
, p. 3613 - 3617 (2007/10/03)
A one-pot three-component coupling involving organolithium reagents, ATPH·cyclopentenone complex, and dihydrofuran·BCl3 complex (see scheme) gives moderate to good yields of the products with selective formation of either the 2,3-cis or 2,3-trans isomer, depending on the nature of the lithium reagent.
COMPARISONS OF VARIOUS BIOLOGICAL ACTIVITIES OF STEREOISOMERS OF METHYL JASMONATE
Koda, Yasunori,Kikuta, Yoshio,Kitahara, Takeshi,Nishi, Tsunehiro,Mori, Kenji
, p. 1111 - 1114 (2007/10/02)
Stereoisomers of methyl jasmonate (JA-Me) showed different biological activities in four bioassay systems.Growth of soybean callus was inhibited strongly by (1R,2S)- and (1R,2R)-JA-Me.By contrast, (1S,2R)- and (1S,2S)-JA-Me had very low inhibitory effect on it, suggesting that the activity is dependent largely on the (1R)-configuration.With regard to potato tuber-induction and the senescence-promotion of oat leaves, although the highest activities were found in (1R,2S)-JA-Me, isomers which have the (1S)-configuration showed considerable activities. (1R,2S)- and (1S,2R)-JA-Me equally inhibited straight growth of oat coleoptiles.These results suggest that requirements of the absolute configurations of the two side chains with respect to the plane of the cyclopentanone ring for each activity are different, and that there are different receptors which trigger reactions leading to the individual activity. Key Word Index - Solanum tuberosum; Solanaceae, Glycine max; Leguminosae; Avena sativa; Gramineae, potato tuberization, soybean callus growth; leaf senescence; coleoptile growth; optically pure enantiomers; methyl jasmonate.
Chemistry and Stereochemistry of Iridoids, XIII. - Synthesis of Enantiomerically Pure Methyl (1R,2S,2''Z)-(+)-Jasmonate Starting from Catalpol
Weinges, Klaus,Lernhardt, Ulrich
, p. 751 - 754 (2007/10/02)
Enantiomerically pure methyl (1R,2S,2''Z)(+)-jasmonate (2), which was recognized as a component of the fragrance of the jasmine flower oil, was synthesized starting from catalpol (3). 2 is easily epimerized to 1.Thus, it is necessary to use very mild conditions in the course of the synthesis and purification.These results raise the question whether 2 exists as a natural product in the flower of jasmine and 1 arises during the isolation.
SYNTHESIS OF N-(JASMONOYL)AMINO ACID CONJUGATES
Kramell, R.,Schmidt, J.,Schneider, G.,Sembdner, G.,Schreiber, K.
, p. 5791 - 5808 (2007/10/02)
Both racemic jasmonic acid and the naturally occurring (-)-enantiomer have been reacted with aliphatic, aromatic as well as acidic amino acids to form amide-linked derivatives.The diastereoisomeric products of (+/-)-jasmonic acid with S-Val, S-Leu, S-Ile, S-Phe, S-Trp, R-Val, and R-Phe could be separated by silica gel chromatography.The synthesized N-(jasmonoyl)-conjugates have been structurally characterized by MS, (1)H NMR, IR and ORD.
