Bodede, OlusolaMore, Garland K.Moodley, RoshilaSteenkamp, PaulBaijnath, HimansuMaharaj, Vinesh J.Prinsloo, Gerhard2023-09-272023-09-272022-06-15Bodede, O.; More, G.K.; Moodley, R.; Steenkamp, P.; Baijnath, H.; Maharaj, V.; Prinsloo, G. New Alk(en)ylhydroxycyclohexanes with Tyrosinase Inhibition Potential from Harpephyllum caffrum Bernh. Gum Exudate. Molecules 2022, 27, 3839. https://DOI.org/10.3390/molecules27123839.1420-3049 (online)10.3390/molecules27123839http://hdl.handle.net/2263/92427SUPPLEMENTARY MATERIALS : FIGURE S1 to S36 containing 1D and 2D NMR spectra, FT-IR, ECD spectra and high-resolution mass spectra of compounds 1–4.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.en© 2022 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license.Harpephyllum caffrum1H NMRCardanolsCyclohexanolAnti-tyrosinaseArticle