One-pot synthesis of bioactive cyclopentenones from α-linolenic acid and docosahexaenoic acid

Maynard D, Müller S, Hahmeier M, Löwe J, Feussner I, Gröger H, Viehhauser A, Dietz K-J (2017)
Bioorganic & Medicinal Chemistry.

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Abstract
Oxidation products of the poly-unsaturated fatty acids (PUFAs) arachidonic acid, alpha-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 alpha-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. Copyright © 2017 Elsevier Ltd. All rights reserved.
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Maynard D, Müller S, Hahmeier M, et al. One-pot synthesis of bioactive cyclopentenones from α-linolenic acid and docosahexaenoic acid. Bioorganic & Medicinal Chemistry. 2017.
Maynard, D., Müller, S., Hahmeier, M., Löwe, J., Feussner, I., Gröger, H., Viehhauser, A., et al. (2017). One-pot synthesis of bioactive cyclopentenones from α-linolenic acid and docosahexaenoic acid. Bioorganic & Medicinal Chemistry. doi:10.1016/j.bmc.2017.07.061
Maynard, D., Müller, S., Hahmeier, M., Löwe, J., Feussner, I., Gröger, H., Viehhauser, A., and Dietz, K. - J. (2017). One-pot synthesis of bioactive cyclopentenones from α-linolenic acid and docosahexaenoic acid. Bioorganic & Medicinal Chemistry.
Maynard, D., et al., 2017. One-pot synthesis of bioactive cyclopentenones from α-linolenic acid and docosahexaenoic acid. Bioorganic & Medicinal Chemistry.
D. Maynard, et al., “One-pot synthesis of bioactive cyclopentenones from α-linolenic acid and docosahexaenoic acid”, Bioorganic & Medicinal Chemistry, 2017.
Maynard, D., Müller, S., Hahmeier, M., Löwe, J., Feussner, I., Gröger, H., Viehhauser, A., Dietz, K.-J.: One-pot synthesis of bioactive cyclopentenones from α-linolenic acid and docosahexaenoic acid. Bioorganic & Medicinal Chemistry. (2017).
Maynard, Daniel, Müller, Sara, Hahmeier, Monika, Löwe, Jana, Feussner, Ivo, Gröger, Harald, Viehhauser, Andrea, and Dietz, Karl-Josef. “One-pot synthesis of bioactive cyclopentenones from α-linolenic acid and docosahexaenoic acid”. Bioorganic & Medicinal Chemistry (2017).
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