Reference - Detail
| RRC ID | 52864 |
|---|---|
| Author | Maynard D, Müller SM, Hahmeier M, Löwe J, Feussner I, Gröger H, Viehhauser A, Dietz KJ. |
| Title | One-pot synthesis of bioactive cyclopentenones from α-linolenic acid and docosahexaenoic acid. |
| Journal | Bioorg Med Chem |
| Abstract |
Oxidation products of the poly-unsaturated fatty acids (PUFAs) arachidonic acid, α-linolenic acid and docosahexaenoic acid are bioactive in plants and animals as shown for the cyclopentenones prostaglandin 15d-PGJ2 and PGA2, cis-(+)-12-oxophytodienoic acid (12-OPDA), and 14-A-4 neuroprostane. In this study an inexpensive and simple enzymatic multi-step one-pot synthesis is presented for 12-OPDA, which is derived from α-linolenic acid, and the analogous docosahexaenoic acid (DHA)-derived cyclopentenone [(4Z,7Z,10Z)-12-[[-(1S,5S)-4-oxo-5-(2Z)-pent-2-en-1yl]-cyclopent-2-en-1yl] dodeca-4,7,10-trienoic acid, OCPD]. The three enzymes utilized in this multi-step cascade were crude soybean lipoxygenase or a recombinant lipoxygenase, allene oxide synthase and allene oxide cyclase from Arabidopsis thaliana. The DHA-derived 12-OPDA analog OCPD is predicted to have medicinal potential and signaling properties in planta. With OCPD in hand, it is shown that this compound interacts with chloroplast cyclophilin 20-3 and can be metabolized by 12-oxophytodienoic acid reductase (OPR3) which is an enzyme relevant for substrate bioactivity modulation in planta. |
| Volume | 26(7) |
| Pages | 1356-1364 |
| Published | 2018-4-1 |
| DOI | 10.1016/j.bmc.2017.07.061 |
| PII | S0968-0896(17)30971-9 |
| PMID | 28818464 |
| MeSH | Cyclopentanes / chemical synthesis* Cyclopentanes / chemistry Docosahexaenoic Acids / chemistry* Molecular Structure Stereoisomerism alpha-Linolenic Acid / chemistry* |
| IF | 3.073 |
| Times Cited | 6 |
| Altmetric score |
オルトメトリクス指標項目
|
| The most frequently cited source | X(Twitter) |
| Total number of mentions | 1 |
| Altmetric score changes over past 6months | 0.0 |
| Resource | |
| Arabidopsis / Cultured plant cells, genes | pda07177 |