Targeted discovery of bioactive natural products using a pharmacophoric deconvolution strategy: Proof of principle with eleganolone from Bifurcaria bifurcata R. Ross

Current Research on the Bioprospection of Linear Diterpenes from Bifurcaria bifurcata: From Extraction Methodologies to Possible Applications

“…This brown macroalga lives in rock pools on the lower and middle tidal, needing shores for its settlement, and is distributed along the coast of the Northern Atlantic, between Morocco and Northwestern Ireland [17]. About 56% of the published (and here reviewed) studies concerning the linear diterpenes fraction of B. bifurcata use samples from the coast of France (Figure 1), which may be associated with the high abundance of this macroalga on that area [8,17,18,19,20,21,22,23,24,25,26,27,28,29,30,31,32,33,34,35,36,37].…”

“…In fact, eleganediol ( 9 ) [19,23,24,26,28,29,31,33,36,37], bifurcane ( 10) [29,30,31,36], and eleganolone ( 15 ) [20,21,22,23,24,26,27,28,30,31,36,37] have been described in several studies concerning B. bifurcata from France, together with other linear diterpenes, namely formyleleganolone ( 35 ) and bibifuran ( 36 ) [34]. The highest eleganediol ( 9 ) and bifurcane ( 10 ) contents (1.12% and 0.37% of dw, respectively) were described by Maréchal et al [36].…”

“…Sample drying and milling are the first steps in the analysis of active compounds from plant raw materials. Macroalgae sample drying is a preliminary step that is often carried out prior to milling and extraction steps, and could be done by air drying (in the shade or not) [23,24,26,31,36,37,44,46,49,52] or by freeze-drying [8,19,20,21,22,27,28,29,30,34,35,38,43,50,51,53,54,55]. Notwithstanding, Semmak et al have obtained linear diterpenes from freshly collected B. bifurcata [47].…”

“…The milling step could also have an important influence in the extraction, specifically in the compounds diffusion from the matrix to the solvent, since by decreasing the particles size, the surface area increases, improving the compounds diffusion [56,57]. Thus, the biomass is often ground prior to extraction [8,21,22,23,24,27,29,31,34,35,36,37,38,43,44,45,46,51,54,55,58,59]. Extraction is considered one of the most relevant steps, being a mass transport phenomenon, where components are transferred from the plant matrix to a solvent up to their equilibrium concentration [56].…”

“…Conventional solid–liquid extraction with continuous stirring (maceration) has been amongst the most used extraction methodology to obtain linear diterpenes from B. bifurcata [19,20,21,22,23,24,26,27,28,29,30,31,32,33,34,36,37,43,44,45,46,47,48,49,50,51]. The extraction yields (EY) obtained by maceration ranged from 0.95% to 9.06% ( w / w ) [21,23,24,27,28,29,31,34,36,37,43,44,45,46,47,49,50,51].…”