An alternative pathway to leukotriene B4 enantiomers involving a 
1,8-diol-forming reaction of an algal oxylipin

Jagusch, Hans; Werner, Markus; Okuno, Toshiaki; Yokomizo, Takehiko; Werz, Oliver; Pohnert, Georg

doi:10.1021/acs.orglett.9b01554

Item

ITEM ACTIONSEXPORT

Add to Basket

Local TagsRelease HistoryDetailsSummary

Released

Journal Article

An alternative pathway to leukotriene B4 enantiomers involving a 1,8-diol-forming reaction of an algal oxylipin

MPS-Authors

There are no MPG-Authors in the publication available

External Resource

No external resources are shared

Fulltext (restricted access)

There are currently no full texts shared for your IP range.

Fulltext (public)

There are no public fulltexts stored in PuRe

Supplementary Material (public)

There is no public supplementary material available

Citation

Jagusch, H., Werner, M., Okuno, T., Yokomizo, T., Werz, O., & Pohnert, G. (2019). An alternative pathway to leukotriene B4 enantiomers involving a 1,8-diol-forming reaction of an algal oxylipin. Organic Letters, 21(12), 4667-4670. doi:10.1021/acs.orglett.9b01554.

Cite as: https://hdl.handle.net/21.11116/0000-0003-CEA6-A

Abstract

Oxidized lipids function as tissue hormones in mammals. An important class of
these oxylipins are the immunomodulatory leukotrienes (LTs). Besides mammals, marine
algae produce bioactive oxylipins, including LTs. The novel acid-labile oxylipin, (5R,8S)-
dihydroxy eicosatetraenoic acid, from the edible alga Gracilaria vermiculophylla rearranges via a
1,8-diol-forming mechanism to inflammatory LTB4 enantiomers that exhibit an enantiospecific
potency toward LTB4 receptor 1. This alternative pathway to a well-known
leukotriene may explain food poisoning after Gracilaria consumption.