6894-38-8Relevant academic research and scientific papers
Lasiojasmonates A-C, three jasmonic acid esters produced by Lasiodiplodia sp., a grapevine pathogen
Andolfi, Anna,Maddau, Lucia,Cimmino, Alessio,Linaldeddu, Benedetto T.,Basso, Sara,Deidda, Antonio,Serra, Salvatorica,Evidente, Antonio
, p. 145 - 153 (2014)
In this study, a strain (BL 101) of a species of Lasiodiplodia, not yet formally described, which was isolated from declining grapevine plants showing wedge-shaped cankers, was investigated for its ability to produce in vitro bioactive secondary metabolites. From culture filtrates of this strain three jasmonic acid esters, named lasiojasmonates A-C and 16-O- acetylbotryosphaerilactones A and C were isolated together with (1R,2R)-jasmonic acid, its methyl ester, botryosphaerilactone A, (3S,4R,5R)-4-hydroxymethyl-3,5- dimethyldihydro-2-furanone and (3R,4S)-botryodiplodin. The structures of lasiojasmonates A-C were established by spectroscopic methods as (1R *,2R*,3′S*, 4′R*,5′R*)-4-hydroxymethyl-3,5- dimethyldihydro-2-furanone, (1R*,2R*, 3′S*,4′R*,5′R *,10′R*,12′R*, 13′R*,14′S*) and (1R *,2R*,3′S*, 4′R*,5′R*,10′S *,12′R*,13′R*, 14′S*)-4-(4-hydroxymethyl-3,5-dimethyltetrahydro-furan-2- yloxymethyl)-3,5-dimethyldihydro-2-furanones jasmonates (1, 4 and 5). The structures of 16-O-acetylbotryosphaerilactones A and C were determined by comparison of their spectral data with those of the corresponding acetyl derivatives obtained by acetylation of botryosphaerilactone A. The metabolites isolated, except 4 and 5, were tested at 1 mg/mL on leaves of grapevine cv. Cannonau and cork oak using the leaf puncture assay. They were also tested on detached grapevine leaves at 0.5 mg/mL and tomato cuttings at 0.1 mg/mL. In all phytotoxic assays only jasmonic acid was found to be active. All metabolites were inactive in the zootoxic assay at 50 μg/mL.
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.
Synthesis of novel methyl jasmonate derivatives and evaluation of their biological activity in various cancer cell lines
Sucu, Bilgesu Onur,Ipek, Ozgecan Savlug,Kurtulus, Sukran Ozdatli,Yazici, Busra Emine,Karakas,Guzel, Mustafa
, (2019/08/06)
Warburg hypothesized that the energy consumption of cancer cells is different than the normal cells. When compared to normal conditions, cancer cells do not undergo tricarboxylic acid (TCA) cycle therefore resulting in more lactate in the cells. Glycolysis pathway is a way of cancer cells to provide energy. The first step in glycolysis is the phosphorylation of glucose to glucose-6-phosphate. This reaction is catalyzed by the hexokinase-II enzyme (HK-II) which is known to be overexpressed in tumor cells. The feeding of cancer cells can be prevented by inhibiting the hexokinase-II enzyme in the first step of aerobic glycolysis. In literature, Methyl Jasmonate (MJ) is known as a Hexokinase-II inhibitor since it disposes VDAC and HK-II interaction on mitochondrial membrane. In our study, we aimed to increase the activity by synthesizing the novel MJ analogues with appropriate modifications. Here we report Hexokinase-2 enzyme and cell viability study results in different cancer cells. Based on the three different cancer cell lines we investigated, our novel MJ analogues proved to be more potent than the original molecule. Thus this research may provide more efficacious/novel HK-II inhibitors and may shed light to develop new anti-cancer agents.
3 - Alkyl -2 - ethoxy carbonyl substituted cyclic conjugated enone asymmetric catalytic hydrogenation and its application (by machine translation)
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, (2018/12/13)
The invention relates to 3 - alkyl - 2 - ethoxy carbonyl substituted cyclic conjugated enone asymmetric catalytic hydrogenation and its application. The chiral spiro pyridine [...] ligand iridium catalyst, in the presence of alkali, to 3 - alkyl - 2 - ethoxy carbonyl substituted cyclic conjugated enone proceeding asymmetric catalytic hydrogenation, to obtain a certain optical purity contains three continuous chiral center ring-like mellow. The method is a high-efficiency, high selectivity, economic, the operability is good, environment friendly, and is suitable for the industrial production of the new method. Can be at a relatively low consumption of catalyst under very high enantioselectivity and yield obtaining optical active contains three continuous chiral center ring-like mellow. The obtained by the method can be used as chiral key chiral raw materials for drug Rocha the forefront of (-) - jasmonic alcohols of the asymmetric synthesis of optical isomers. (by machine translation)
In vitro stability and in vivo anti-inflammatory efficacy of synthetic jasmonates
Dang, Hung The,Lee, Yoon Mi,Kang, Gyeoung Jin,Yoo, Eun Sook,Hong, Jongki,Lee, Sun Mee,Lee, Sang Kook,Pyee, Yuna,Chung, Hwa-Jin,Moon, Hyung Ryong,Kim, Hyung Sik,Jung, Jee H.
scheme or table, p. 4109 - 4116 (2012/09/22)
A chlorinated methyl jasmonate analog (J7) was elaborated as an in vitro anti-inflammatory lead. However, its in vitro efficacy profile was not reproduced in a subsequent in vivo evaluation, presumably due to its rapid enzymatic hydrolysis in a biological system. In an attempt to improve the metabolic stability of the lead J7 by replacement of its labile methyl ester with reasonable ester groups, several analogs resistant to enzymatic hydrolysis were synthesized. In vivo evaluation of the stability-improved analogs showed that these compounds displayed higher efficacy than the lead J7, suggesting that these new jasmonate analogs may serve as potential anti-inflammatory leads.
Stereoselective synthesis of epi-jasmonic acid, tuberonic acid, and 12-oxo-PDA
Nonaka, Hisato,Ogawa, Narihito,Maeda, Noriaki,Wang, Yong-Gang,Kobayashi, Yuichi
experimental part, p. 5212 - 5223 (2010/12/25)
epi-Jasmonic acid (epi-JA) and tuberonic acid (TA) were synthesized from the key aldehyde, all cis-2-(2-hydroxy-5-vinylcyclopentyl)acetaldehyde (14), which was in turn prepared stereoselectively from the (1R)-acetate of 4-cyclopentene-1,3-diol (10) through SN2-type allylic substitution with CH2CHMgBr followed by Mitsunobu inversion, Eschenmoser-Claisen rearrangement, and regioselective Swern oxidation of the corresponding bis-TES ether (13). Wittig reaction of the aldehyde 14 with [Ph3P(CH 2)Me]+Br- followed by oxidation afforded epi-JA (3) stereoselectivity over the trans isomer. Similarly, TA (5) was synthesized. Furthermore, the above findings were applied successfully to improve the total efficiency of the previous synthesis of 12-oxo-PDA (1).
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
Asymmetric total synthesis of enantiopure (-)-methyl jasmonate via catalytic asymmetric intramolecular cyclopropanation of α-diazo-β-keto sulfone
Takeda, Hiroyuki,Watanabe, Hideaki,Nakada, Masahisa
, p. 8054 - 8063 (2007/10/03)
A new asymmetric total synthesis of enantiopure (-)-methyl jasmonate is described. This synthesis was accomplished starting from the new enantiopure building block prepared via the catalytic asymmetric intramolecular cyclopropanation (IMCP) of the α-diazo-β-keto 1-naphthyl sulfone, which was devised to give good selectivity both in the IMCP reaction and in the C-alkynylation of the intermediate required for the total synthesis of enantiopure (-)-methyl jasmonate.
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.
