4.6 Article

New Alk(en)ylhydroxycyclohexanes with Tyrosinase Inhibition Potential from Harpephyllum caffrum Bernh. Gum Exudate

Journal

MOLECULES
Volume 27, Issue 12, Pages -

Publisher

MDPI
DOI: 10.3390/molecules27123839

Keywords

Harpephyllum caffrum; H-1 NMR; cardanols; cyclohexanol; anti-tyrosinase

Funding

  1. University of KwaZulu-Natal
  2. University of Johannesburg
  3. University of South Africa

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This study presents the first report on the phytochemical investigation of Harpephyllum caffrum Bernh. gum exudate, and identifies a known compound and three new compounds from the gum. The ethanolic extract of the gum is found to be a potent tyrosinase inhibitor, suggesting its potential application in cosmetics.
This work presents the first report on the phytochemical investigation of Harpephyllum caffrum Bernh. gum exudate. A known cardanol, 3-heptadec-12 '-Z-enyl phenol (1) and three new alk(en)ylhydroxycyclohexanes, namely, (1R,3R)-1,3-dihydroxy-3-[heptadec-12 '(Z)-enyl]cyclohexane (2) (1S,2S,3S,4S,5R)-1,2,3,4,5-pentahydroxy-5-[octadec-13 '(Z)-enyl]cyclohexane (3) and (1R,2S,4R)-1,2,4-trihydroxy-4-[heptadec-12 '(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 mu g/mL while compounds 2 and 3, with IC50 values of 24.90 and 26.99 mu 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.

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