New alk(en)ylhydroxycyclohexanes with tyrosinase inhibition potential from Harpephyllum caffrum Bernh. gum exudate

Abstract

This work presents the first report on the phytochemical investigation of Harpephyllum caffrum Bernh. gum exudate. A known cardanol, 3-heptadec-120-Z-enyl phenol (1) and three new alk(en)ylhydroxycyclohexanes, namely, (1R,3R)-1,3-dihydroxy-3-[heptadec-120(Z)-enyl]cyclohexane (2) (1S,2S,3S,4S,5R)-1,2,3,4,5-pentahydroxy-5-[octadec-130(Z)-enyl]cyclohexane (3) and (1R,2S,4R)- 1,2,4-trihydroxy-4-[heptadec-120(Z)-enyl]cyclohexane (4) were isolated from the gum. The structures of the compounds were determined by extensive 1D and 2D NMR spectroscopy and HR-ESI-MS data. The ethanolic extract of the gum was found to be the most potent tyrosinase inhibitor with IC50 of 11.32 g/mL while compounds 2 and 3, with IC50 values of 24.90 and 26.99 g/mL, respectively, were found to be potential anti-tyrosinase candidates from the gum. Gum exudate may be a potential source for non-destructive harvesting of selective pharmacologically active compounds from plants. The results also provide evidence that H. caffrum gum may find application in cosmetics as a potential anti-tyrosinase agent.