Pterocarpans: interesting natural products with antifungal activity and other biological properties

Abstract

Among the phytoalexins with the highest antifungal activity is the isoflavonoid based group of pterocarpans. Here, we present a comprehensive inventory of the structures and sources of pterocarpans, and summarize some of their most interesting biological activities.

Glycosylation of (–)-maackiain byBeauveria bassianaandCunninghamella echinulatavar.elegans

“…As the second largest group of isoflavonoids, naturally occurring pterocarpans have been investigated extensively (Jiménez-González et al 2008). Their antimicrobial (Jiménez-González et al 2008), anticancer (Militao et al 2005), anti-HIV (Engler et al 1993), antiinflammatory (Selvam et al 2004), antiparasitic (Salem & Werbovetz 2006), kidney acylase I inhibition (Stocker et al 2005) and neuraminidase inhibition activities (Ryu et al 2008) as well as synthesis (Engler et al 1999) have been reported.…”

LC-ESI–MS/MS method for bioanalytical determination of osteogenic phytoalexin, medicarpin, and its application to preliminary pharmacokinetic studies in rats

“…Medicarpin is an active constituent found in its stem bark that has shown potent antifungal [1]and antiosteoporotic activities [3][4][5]. It is a pterocarpan-type phytoalexin possessing a tetracyclic benzofuran-benzopyran ring system, structurally resembling isoflavones [6]. Phytoalexins are secondary plant metabolites that form one of the components of plant's induced defense mechanism [7].…”

“…These low molecular weight phytochemicals are synthesized denovo by plants on exposure to microorganisms or abiotic agents and get accumulated at the site of infection [8,9]. The largest group of phytoalexins is the pterocarpan type phytoalexins found mainly in Leguminosae family and have shown to possess numerous pharmacological effects [6,[10][11][12].…”

“…Medicarpin (Figure 1) is one such phytoalexin that is found in various leguminous plants [6]such as chickpea [13,14], peanut [15], alfa-alfa [16], red clover [17].In a study conducted in ovariectomized (OVx) mice, it was shown that medicarpin reduced osteoclastogenesis in bone marrow cells while increasing the formation of osteoprogenitor cells. This bone sparing action was observed even at a low concentration of 10 -10 M of medicarpin [3].…”

A pterocarpan from the seeds of Bituminaria morisiana

“…Pterocarpans from B. morisiana also exert powerful antioxidant activities [4]. Because of the promising biological profile shown by pterocarpans, covering antifungal, antibacterial, antifeedant, anti-HIV and cytotoxic effects [5], we decided to study the phytochemical composition of the seeds of B. morisiana. The phytochemical investigation led to the isolation of a new prenylated pterocarpan 1, as well as one known pterocarpan and two known furocoumarins (2-4, Fig.…”