Tyrosinase inhibitors from the fruits of Madhuca latifolia

Shazia Khan*, Mahmud Tareq Hassan Khan, M. Nadeem Kardar

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Tyrosinase is a copper-containing enzyme that catalyzes melanin synthesis in skin melanocytes by oxidation. Eighteen compounds of different classes, i.e., pentacyclic triterpenes, flavonoids, steroids, aromatics, mono and triglycerides and straight chain hydrocarbons were isolated from the fruit pulp and seeds of Madhuca latifolia and were identified as betulinic acid 3-β-caprylate (1), stigmasterol (2), ursolic acid (3), p-hydroxyacetophenone (4), hydroquinone (5), 4-hydroxymethylbenzoate (6), quercetin (7), taxifolin (8), hexadecenoic acid (9), β-amyrin acetate (10), triglyceride of stearo-oleo-palmitin (11), erythrodiol 3-β-caprylate (12), oleanolic acid 3-β-caprylate (13), monoglyceride of oleic acid (14), nonacosane (15), madhushazone (16), madhusalmone (17), madhucic acid (18). Structural characterizations of these were made by comparison of 1H and 13C NMR spectra with those reported in the literatures. The tyrosinase inhibitory potency of these compounds has been evaluated and attempts to justify their structure-acitivity relationships have been made in the present work. The compounds 3, 4, 5, 6a (acetyle derivative of 6), 7, 8a (acetyl derivative of 8), 16, 17, and 18 exhibited much better potency than the reference inhibitor kojic acid, whereas compound 3 was the most active among them.

Original languageEnglish
Pages (from-to)31-36
Number of pages6
JournalCurrent Bioactive Compounds
Volume10
Issue number1
DOIs
Publication statusPublished - 2014

Keywords

  • Madhuca latifolia
  • Madhucic acid
  • Madhusalmone
  • Madhushazone
  • Tyrosinase inhibition
  • Ursolic acid

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