ArticleLipids2006
Synthesis of 3-oxalinolenic acid and beta-oxidation-resistant 3-oxa-oxylipins.
Article in Lipids, 2006. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
2 citing papers in PubMed, 14 citations in OpenAlex.
- The Physcomitrella patens unique alpha-dioxygenase participates in both developmental processes and defense responses.BMC plant biology · 2015Article
- Oxylipins in moss development and defense.Frontiers in plant science · 2015Review
Corrections and comments
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Authors and funding
6 authors at 5 institutions in 4 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
3-Oxalinolenic acid (3-oxa-9(Z),12(Z),15(Z)-octadecatrienoic acid or (6(Z),9(Z),12(Z)-pentadecatrienyloxy)acetic acid) was synthesized from 5(Z),8(Z),11(Z),14(Z),17(Z)-eicosapentaenoic acid by a sequence involving the C15 aldehyde 3(Z),6(Z),9(Z),12(Z)-pentadecatetraenal as a key intermediate. Conversion of the aldehyde by isomerization and two steps of reduction afforded 6(Z),9(Z),12(Z)-pentadecatrienol, which was coupled to bromoacetate to afford after purification by HPLC >99%-pure 3-oxalinolenic acid in 10-15% overall yield. 3-Oxalinolenic acid was efficiently oxygenated by soybean lipoxygenase-1 into 3-oxa-13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoic acid, and this hydroperoxide could be further converted chemically into 3-oxa-13(S)-hydroxy-9(Z),11 (E),15(Z)-octadecatrienoic acid and 3-oxa-13-oxo-9(Z),11 (E),15(Z)-octadecatrienoic acid. The 3-oxa-hydroperoxide also served as the substrate for the plant enzymes allene oxide synthase, divinyl ether synthase, and hydroperoxide lyase to produce 3-oxa-12-oxo-10,15(Z)-phytodienoic acid and other 3-oxa-oxylipins that were characterized by MS. 3-Oxalinolenic acid was not oxygenated by 9-lipoxygenase from tomato but was converted at a slow rate into 3-oxa-9(S)-hydroperoxy-10(E),12(Z),15(Z)-octadecatrienoic acid by recombinant maize 9-lipoxygenase. Recombinant alpha-dioxygenase-1 from Arabidopsis thaliana catalyzed the conversion of 3-oxalinolenic acid into a 2-hydroperoxide, which underwent spontaneous degradation into a mixture of 6,9,12-pentadecatrienol and 6,9,12-pentadecatrienyl formate. A novel alpha-dioxygenase from the moss Physcomitrella patens was cloned and expressed and was found to display the same activity with 3-oxalinolenic acid as Arabidopsis thaliana alpha-dioxygenase-1. Lipoxygenase-generated 3-oxa-oxylipins are resistant toward beta-oxidation and have the potential for displaying enhanced biological activity in situations where activity is limited by metabolic degradation.
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