Cucurbic acid and its 6,7-stereoisomers

Dathe, W.; Schindler, Christiane; Schneider, G.; Schmidt, Jürgen; Porzel, Andrea; Jensen, Einar; Yamaguchi, Isomaro

doi:10.1016/0031-9422(91)85038-2

Cited by 36 publications

(21 citation statements)

References 19 publications

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“…It is a large family of natural organic compounds widespread in plants and some fungi [3,9,13,22,24,35]. Up to now, jasmonates have been found in 206 plant species that belong to 160 families.…”

Section: Introductionmentioning

confidence: 99%

“…First of all, jasmonates act as endogenous growth regulators that control plant development, including seed germination, pollen development, ethylene synthesis, senescence, and tuber formation, through regulation of many physiological processes on the morphological, molecular, and cellular levels [11,29,30,34]. Furthermore, they play a significant cell-signalling role in the defence responses of plants and can be involved in intra-and inter-plant communication [5,9,12,20,32]. Jasmonates modulate expression of numerous genes encoding proteins with stressrelated and protective functions, e.g.…”

Section: Introductionmentioning

confidence: 99%

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Enantioselective Microbial Hydroxylation as a Useful Tool in the Production of Jasmonate Derivatives with Aphid Deterrent Activity

2015

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Microbial transformations of two natural compounds dihydrojasmone (1) and cis-jasmone (3) in the growing cultures of selected twenty strains have been investigated. The studies have demonstrated a biocatalytic potential of tested microorganisms for the enantioselective hydroxylation of jasmonates. The substrates underwent an effective regio- and stero-selective hydroxylation at the allylic position in the cyclopentenone ring, and the corresponding optically pure keto-alcohols (2, 4) were obtained. The process of biohydroxylation depended on the composition of reaction medium. In the studied cultures, (+)-(R)-4-hydroxydihydrojasmone (2) and (+) and (-)-4-hydroxyjasmone (4a, 4b) were produced in good yields and high enantiomeric excesses. Moreover, the introduction of the hydroxy group into the molecule of jasmonate ketones 1 and 3 leads to biologically active derivatives 2 and 4 that regulate the behaviour of aphids Myzus persicae by termination of their feeding.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Enantioselective Microbial Hydroxylation as a Useful Tool in the Production of Jasmonate Derivatives with Aphid Deterrent Activity

2015

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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%

“…The hydroxylated molecules generated here (1, 2 and 3) by means of the enzymatic action of G. fujikuroi correspond to the molecule cucurbic acid (CA) and some of its stereoisomers, a metabolic derivative of JA, whose presence has been detected in both higher plants and fungi in low contents (Dathe et al 1991;. 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).…”

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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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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“…Although the resolution process could give the products with > 95% ee on average, we tried further purification. The resolved alcohol of natural configuration, i.e., (þ)-7 [14], was converted to its 3,5-dinitrobenzoyl (DNB) derivative (þ)-8, which was recrystallized from hexane/AcOEt to be enantiomerically pure ( > 99.8% ee). Selective hydrolysis of the DNB group and the resulting alcohol (þ)-7 was oxidized to give pure (À)-MJA ((À)-2).…”

mentioning

confidence: 99%

Synthesis and Odor Description of Both Enantiomers of Methyl 4,5-Didehydrojasmonate, a Component of Jasmin Absolute

Asamitsu

Nakamura

Ueda

et al. 2006

C&B

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Synthesis of both enantiomers of methyl 4,5-didehydrojasmonate (1, D 4,5 -MJA; > 99.8% ee), a constituent of jasmin absolute, established the absolute configuration of the natural product, and their odor quality was evaluated. The fragrance of the natural (3S,7R)-enantiomer (a fresh natural, sweet floral fruity odor, reminiscent of Jasmin and Ylang Ylang flower, more intensive and tenacious) was superior to that of the unnatural (3R,7S)-enantiomer (a floral green odor with slight metallic green aspect, less intensive than the natural form) and the racemate (green-floral note, having weak and less volume than methyl jasmonate). Odor difference between natural and unnatural enantiomers of methyl jasmonate (2) is also reported.

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Cucurbic acid and its 6,7-stereoisomers

Cited by 36 publications

References 19 publications

Enantioselective Microbial Hydroxylation as a Useful Tool in the Production of Jasmonate Derivatives with Aphid Deterrent Activity

Enantioselective Microbial Hydroxylation as a Useful Tool in the Production of Jasmonate Derivatives with Aphid Deterrent Activity

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

Synthesis and Odor Description of Both Enantiomers of Methyl 4,5-Didehydrojasmonate, a Component of Jasmin Absolute

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