Key Laboratory of Green Chemistry & Technology (MOE), College of Chemistry, Sino-British Materials Research Institute, College of Physical Science & Technology, Sichuan University, No. 29, Wangjiang Road, Chengdu, Sichuan 610064, P. R. China.
Nat Prod Rep. 2018 Jan 25;35(1):54-74. doi: 10.1039/c7np00044h.
Covering up to February 2017The 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.
涵盖至 2017 年 2 月，几种花椒属（又名“花椒”）的种皮长期以来一直被亚洲各地用于烹饪，尤其是在中国西南部的四川（原称四川）菜系，这是因为它们独特的刺痛和麻木的味觉感受来自于一系列多不饱和脂肪酸酰胺（烷酰胺）成分。过去十年，学术界和工业界对这些辛辣的花椒衍生烷酰胺的兴趣显著增加，同时也有大量研究旨在阐明天然产物所表现出的几种与医学相关的生物活性背后的具体生化机制。这种兴趣的迅速增加部分是由于过去几年报道的有机合成方面的进展，这些进展最终使得能够以多克数量生产非对映纯的花椒烷酰胺和相关类似物。本文综述了花椒衍生的多不饱和脂肪酸酰胺和合成类似物的发现、全合成和生物学评价。还提供了有关化学合成如何进一步有益于该领域未来化学生物学研究的重要见解。
