New alk(en)ylhydroxycyclohexanes with tyrosinase inhibition potential from Harpephyllum caffrum Bernh. gum exudate
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Date
Authors
Bodede, Olusola
More, Garland K.
Moodley, Roshila
Steenkamp, Paul
Baijnath, Himansu
Maharaj, Vinesh J.
Prinsloo, Gerhard
Journal Title
Journal ISSN
Volume Title
Publisher
MDPI
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.
Description
SUPPLEMENTARY MATERIALS : FIGURE S1 to S36 containing 1D and 2D NMR spectra, FT-IR, ECD spectra and high-resolution mass spectra of compounds 1–4.
Keywords
Harpephyllum caffrum, 1H NMR, Cardanols, Cyclohexanol, Anti-tyrosinase
Sustainable Development Goals
Citation
Bodede, 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.