Planta Med 2008; 74 - PB17
DOI: 10.1055/s-0028-1084363

Tyrosinase inhibitors and acylated sesquiterpene diglycosides from Guioa crenulata and G. villosa

L Voutquenne-Nazabadioko 1, A Alabdul Magid 1, M Litaudon 2, C Lavaud 1
  • 1Groupe Isolement-Structure, CNRS UMR 6229, IFR 53 Biomolécules, Bât. 18, BP 1039, 51687 Reims Cedex 2, France
  • 2Institut de Chimie des Substances Naturelles du CNRS, Bât. 27, avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France

As new-Caledonian Guioa gracillis extracts are used in cosmetic and pharmaceutical preparations for the treatment of skin aging [1], we investigated the tyrosinase inhibitory activity of two Caledonian Guioa sp., G. crenulata and G. villosa. Through a bioassay-guided phytochemical investigation involving mushroom tyrosinase inhibitory activity, seven new acylated farnesyl diglycosides (Crenulatosides A-G) (1-7), five flavonoids (8-12), one trimeric proanthocyanidin (13), two triterpenes (14-15), and one cerebroside (16), were isolated from the leaves of G. crenulata [2] and G. villosa [3]. The sesquiterpene diglycosides isolated form the active EtOAc extract showed no inhibitory activity, whereas betulin (14), lupeol (15) and soyacerebroside I (16) demonstrated a potent tyrosinase inhibitory activity [3].

Structures of isolated compounds were established by means of 1D and 2D NMR experiments as well as HR-ESI-MS.

The ethanol and ethyl acetate extracts of the leaves were tested in a preliminary biological screening, but exhibited no cytotoxic activity, no inhibition of acetylcholinesterase, and no activity in the tubulin test and on topoisomerase I.

References: 1. Renimel et al. (1998) FR Patent 199961220

2. Alabdul Magid et al. (2005) Phytochemistry 66:2714–8

3. Alabdul Magid et al. (2008) Planta Med 74:55–60