Progress in the Chemistry of Naturally Occurring Coumarins.

Abstract

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.