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

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.

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Item Permalink: https://hdl.handle.net/21.11116/0000-0003-CEA6-A Version Permalink: https://hdl.handle.net/21.11116/0000-0009-3C57-3
Genre: Journal Article

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EXT659s1.pdf (Supplementary material), 3MB
 
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 Creators:
Jagusch, Hans, Author
Werner, Markus, Author
Okuno, Toshiaki, Author
Yokomizo, Takehiko, Author
Werz, Oliver, Author
Pohnert, Georg1, Author           
Affiliations:
1External Organizations, ou_persistent22              

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 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.

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 Dates: 2019-06-1320192019
 Publication Status: Issued
 Pages: -
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 Table of Contents: -
 Rev. Type: -
 Identifiers: Other: EXT659
DOI: 10.1021/acs.orglett.9b01554
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Title: Organic Letters
  Other : Org. Lett.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 21 (12) Sequence Number: - Start / End Page: 4667 - 4670 Identifier: ISSN: 1523-7060
CoNE: https://pure.mpg.de/cone/journals/resource/954925626338