Sarker Satyajit D, Nahar Lutfun
Medicinal Chemistry and Natural Products Research Group, School of Pharmacy and Biomolecular Sciences, Faculty of Science, Liverpool John Moores University, Byrom Street, Liverpool, L3 3AF, UK.
Prog Chem Org Nat Prod. 2017;106:241-304. doi: 10.1007/978-3-319-59542-9_3.
Coumarins are the largest group of 1-benzopyran derivatives found in plants. The initial member of this group of compounds, coumarin (2H-1-benzopyran-2-one), a fragrant colorless compound, was first isolated from the Tonka bean (Dipteryx odorata, family Fabaceae) in 1820. The name coumarin comes from a French term for the tonka bean, coumarou. Since the discovery of coumarin, several of its derivatives, with umbelliferone (7-hydroxycoumarin) being the most common one, have been reported from various natural sources. The families Apiaceae, Asteraceae, and Rutaceae are the three major plant sources of coumarins.Generally, these plant secondary metabolites may be classified into simple, simple prenylated, simple geranylated, furano, pyrano, sesquiterpenyl and oligomeric coumarins. Using this standard classification, this chapter aims to present an account on the advances of the chemistry of naturally occurring coumarins, as reported in the literature during the period 2013-2015.In Sect. 1, the coumarins are introduced and their generic biosynthetic route discussed briefly. In Sect. 2, the largest of the three sections, various classes of natural coumarins are detailed, with their relevant structures and the citation of appropriate references. In a concluding section, it is highlighted that during the last 3 years, more than 400 coumarins have been reported in the literature. Many of these coumarins have been re-isolations of known compounds from known or new sources, most often associated with various biological activities. However, a substantial number of coumarins bearing new skeletons, especially dimers, prenylated furanocoumarins, sesquiterpenyl, and some unusual coumarins were also reported during the period of 2013-2015.Coumarin chemistry remains one of the major interest areas of phytochemists, especially because of their structural diversity and medicinal properties, along with the wide-ranging bioactivities of these compounds, inclusive of analgesic, anticoagulant anti-HIV, anti-inflammatory, antimicrobial, antineoplastic, antioxidant, and immunomodulatory effects. Despite significant advancements in the extraction, isolation, structure elucidation and bioactivity testing of naturally occurring coumarins, only a marginal advancement has been observed recently in relation to the study of their biosynthesis.
香豆素是植物中发现的最大一类1-苯并吡喃衍生物。这类化合物的首个成员香豆素（2H-1-苯并吡喃-2-酮）是一种有香味的无色化合物，于1820年首次从零陵香豆（豆科植物零陵香豆）中分离出来。香豆素这个名字来源于零陵香豆的一个法语名称coumarou。自从发现香豆素以来，已从各种天然来源报道了它的几种衍生物，其中伞形花内酯（7-羟基香豆素）最为常见。伞形科、菊科和芸香科是香豆素的三大主要植物来源。一般来说，这些植物次生代谢产物可分为简单香豆素、简单异戊烯基化香豆素、简单香叶基化香豆素、呋喃香豆素、吡喃香豆素、倍半萜基香豆素和聚合香豆素。基于这种标准分类，本章旨在介绍2013 - 2015年期间文献报道的天然香豆素化学进展。在第1节中，介绍了香豆素并简要讨论了其一般生物合成途径。在第2节（三个部分中篇幅最长的），详细介绍了各类天然香豆素，给出了它们的相关结构并引用了适当的参考文献。在结论部分，强调了在过去3年里，文献报道了400多种香豆素。其中许多香豆素是从已知或新来源重新分离出的已知化合物，大多与各种生物活性相关。然而，在2013 - 2015年期间也报道了大量带有新骨架的香豆素，特别是二聚体、异戊烯基化呋喃香豆素、倍半萜基香豆素以及一些不寻常的香豆素。香豆素化学仍然是植物化学家主要关注的领域之一，尤其是因为它们的结构多样性和药用特性，以及这些化合物广泛的生物活性，包括镇痛、抗凝、抗HIV、抗炎、抗菌、抗肿瘤、抗氧化和免疫调节作用。尽管在天然香豆素的提取、分离、结构解析和生物活性测试方面取得了显著进展，但最近在其生物合成研究方面仅取得了微小进展。
