Analgesic and anti-inflammatory activities evaluation of (-)-O-acetyl, (-)-O-methyl, (-)-O-dimethylethylamine cubebin and their preparation from (-)-cubebin

Antimycobacterial Activity of Natural and Semi-Synthetic Lignans

“…The cubebin-rich fractions [hexane/dichloromethane (1:1) and 100% dichloromethane] were submitted to repeated crystallization from n-hexane/ acetone to furnish crystalline cubebin (37 g). Its chemical structure was confi rmed by comparison of its 1 H NMR and IR data with those published in the literature (Koul et al, 1988;Souza et al, 2004). The purity of 1 was estimated to be 99% by both HPLC and spectral data analysis.…”

“…Lignans, one of the oldest classes of natural products, have attracted much interest over the years on account of their broad range of biological activities, including antileishmanial (Da Silva Filho et al, 2008b), trypanocidal (Da Silva Filho et al, 2004b;Souza et al, 2005), and anti-infl ammatory Souza et al, 2004;Da Silva Filho et al, 2004c) activities. Cubebin, a dibenzylbutyrolactolic lignan, and its semi-synthetic derivatives have been investigated for their antiprotozoal and antibacterial activities (Andrade et al, 2009;Souza et al, 2005).…”

Green Oxidation Reactions of Drugs Catalyzed by Bio-inspired Complexes as an Efficient Methodology to Obtain New Active Molecules

“…Considering its promising biological activities, as well as its potential use as trypanocidal drug, large quantities of (-)-hinokinin are needed. (-)-Hinokinin and (-)-cubebin co-occur in P. cubeba, where they are among the major components of the biomass (Souza et al, 2004;Silva et al, 2007). In a traditional process, the oxidation of (-)-cubebin, catalyzed by pyridinium chlorochromate, PCC, can produce additional quantities of (-)-hinokinin.…”

“…Thus, lignans are biosynthesized by dimerization, via oxidative coupling of phenylpropanoids units (C6C3), forming a variety of structurally distinct subclasses. An example of these substances is cubebin (Figure 9a), a dibenzylbutyrolactone lignan obtained from the seeds of Piper cubeba (Piperaceae), which has anti-inflammatory (Souza et al, 2004;Silva et al,2005); and trypanocidal (Bastos et al, 2001) activities. Neolignans are dimers derived from condensation by oxidative coupling of allyl and /or propenyl phenols and, unlike lignans, are free of oxidation in the γ carbon atom.…”

“…(-)-Hinokinin, Figure 12, a dibenzylbutyrolactone lignan, possesses antileishmanial, antiinflammatory, antigenotoxic (Souza et al,2004 ;Medola et al, 2007), and significant in vitro and in vivo trypanocidal activities against Trypanosoma cruzi, the etiologic agent of Chagas` disease . Considering its promising biological activities, as well as its potential use as trypanocidal drug, large quantities of (-)-hinokinin are needed.…”