12-Hydroxyjasmonic acid - CAS 140631-27-2
Catalog number: 140631-27-2
Not Intended for Therapeutic Use. For research use only.
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12-Hydroxyjasmonic acid isolated from the herbs of Stephania japonica.
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1.Biochemical and molecular characterization of a hydroxyjasmonate sulfotransferase from Arabidopsis thaliana.
Gidda SK;Miersch O;Levitin A;Schmidt J;Wasternack C;Varin L J Biol Chem. 2003 May 16;278(20):17895-900. Epub 2003 Mar 10.
12-Hydroxyjasmonate, also known as tuberonic acid, was first isolated from Solanum tuberosum and was shown to have tuber-inducing properties. It is derived from the ubiquitously occurring jasmonic acid, an important signaling molecule mediating diverse developmental processes and plant defense responses. We report here that the gene AtST2a from Arabidopsis thaliana encodes a hydroxyjasmonate sulfotransferase. The recombinant AtST2a protein was found to exhibit strict specificity for 11- and 12-hydroxyjasmonate with K(m) values of 50 and 10 microm, respectively. Furthermore, 12-hydroxyjasmonate and its sulfonated derivative are shown to be naturally occurring in A. thaliana. The exogenous application of methyljasmonate to A. thaliana plants led to increased levels of both metabolites, whereas treatment with 12-hydroxyjasmonate led to increased level of 12-hydroxyjasmonate sulfate without affecting the endogenous level of jasmonic acid. AtST2a expression was found to be induced following treatment with methyljasmonate and 12-hydroxyjasmonate. In contrast, the expression of the methyljasmonate-responsive gene Thi2.1, a marker gene in plant defense responses, is not induced upon treatment with 12-hydroxyjasmonate indicating the existence of independent signaling pathways responding to jasmonic acid and 12-hydroxyjasmonic acid.
2.Synthesis and bioactivity of potassium beta-D-glucopyranosyl 12-hydroxy jasmonate and related compounds.
Nakamura Y;Miyatake R;Inomata S;Ueda M Biosci Biotechnol Biochem. 2008 Nov;72(11):2867-76. Epub 2008 Nov 7.
Albizzia saman, a leguminous plant, is known to open its leaves in the daytime and sleep at night with the leaves folded. beta-D-Glucopyranosyl 12-hydroxyjasmonate (1) was isolated as an endogenous chemical factor controlling this leafmovement. We developed a concise synthesis of optically pure (-)-1 in 9 steps from (+)-2 with a total yield of 58%. Similarly, such analogs of 1 as epi-LCF (13), enantiomer (14), and galactoside (19) were synthesized for a structure activity relationship (SAR) study. The results of this SAR study strongly suggest that the mechanism for the leaf-closing activity of 1 would be different from that of methyl jasmonate, and also suggest the involvement of a different kind of target protein which recognizes the trans-isomer of a jasmonate derivative.
3.Depsides and other polar constituents from Origanum dictamnus L. and their in vitro antimicrobial activity in clinical strains.
Chatzopoulou A;Karioti A;Gousiadou C;Lax Vivancos V;Kyriazopoulos P;Golegou S;Skaltsa H J Agric Food Chem. 2010 May 26;58(10):6064-8. doi: 10.1021/jf904596m.
Phytochemical investigation of the polar extracts of the aerial parts of Origanum dictamnus afforded 15 secondary metabolites. One new depside was isolated, to which the trivial name salvianolic acid P (1) was given, in addition to the known depsides rosmarinic acid (2) and rosmarinic acid methyl ester (3), as well as two monoterpenes, thymoquinone (4) and thymoquinol 2-O-beta-glucopyranoside (5); two simple phenolic acids, oresbiusin A (6) and E-caffeic acid (7); six flavonoids, namely, apigenin (8), kaempferol (9), quercetin (10), eriodictyol (11), taxifolin (12), naringenin (13); and two alicyclic derivatives, that is, 12-hydroxyjasmonic acid (14) and its 12-O-beta-d-glucoside (15). The structures of all isolated compounds were established by spectroscopic methods, mainly 1D and 2D NMR, as well as HPLC-DAD-MS and HR-MS spectrometric analyses. The absolute configuration of compound 1 was determined by CD measurements as 7'R, 7''S, 8''S. Compound 1 is interesting as it contains a benzodioxane ring, which is unusual in natural products. Moreover, it has been proved to be active against the Gram-negative clinical strains Acinetobacter hemolyticus , Empedobacter brevis , Pseudomonas aeruginosa , and Klebsiella pneumoniae .
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