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Issue 1, 2018
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Polyunsaturated fatty acid amides from the Zanthoxylum genus – from culinary curiosities to probes for chemical biology

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Abstract

Covering up to February 2017

The pericarps of several species from the Zanthoxylum genus, a.k.a. the “prickly ash”, have long been used for culinary purposes throughout Asia, most notably in the Sichuan (previously Szechuan) cuisine of Southwestern China, due to the unique tingling and numbing orosensations arising from a collection of polyunsaturated fatty acid amide (alkamide) constituents. The past decade has experienced dramatically increased academic and industrial interest in these pungent Zanthoxylum-derived alkamides, with a concomitant explosion in studies aimed at elucidating the specific biochemical mechanisms behind several medically-relevant biological activities exhibited by the natural products. This rapid increase in interest is partially fueled by advances in organic synthesis reported within the past few years that finally have allowed for the production of diastereomerically-pure Zanthoxylum alkamides and related analogs in multigram quantities. Herein is a comprehensive review of the discovery, total synthesis, and biological evaluation of Zanthoxylum-derived polyunsaturated fatty acid amides and synthetic analogues. Critical insights into how chemical synthesis can further benefit future chemical biology efforts in the field are also provided.

Graphical abstract: Polyunsaturated fatty acid amides from the Zanthoxylum genus – from culinary curiosities to probes for chemical biology

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Publication details

The article was received on 31 Aug 2017 and first published on 04 Jan 2018


Article type: Review Article
DOI: 10.1039/C7NP00044H
Citation: Nat. Prod. Rep., 2018,35, 54-74
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    Polyunsaturated fatty acid amides from the Zanthoxylum genus – from culinary curiosities to probes for chemical biology

    J. J. Chruma, D. J. Cullen, L. Bowman and P. H. Toy, Nat. Prod. Rep., 2018, 35, 54
    DOI: 10.1039/C7NP00044H

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