Abstract
Through a bioassay-guided phytochemical investigation involving mushroom tyrosinase
inhibitory activity, seven farnesyl diglycosides (1 - 7), five flavonoids (8 - 12), one trimeric proanthocyanidin (13), two triterpenes (14 and 15), and one cerebroside (16), were isolated from the leaves of Caledonian Guioa villosa. Among them, crenulatosides E, F and G (1 - 3) were new acyclic sesquiterpene diglycosides. The sesquiterpene diglycosides isolated
from the active EtOAc extract showed no inhibitory activity, whereas betulin (14), lupeol (15) and soyacerebroside I (16) demonstrated a potent tyrosinase inhibitory activity.
Key words
Guioa villosa
- Sapindaceae - terpenoids - tyrosinase inhibitor
- 1
Kim J -Y, Uyama H.
Tyrosinase inhibitors from natural and synthetic sources: Structure, inhibition mechanism
and perspective for the future.
Cell Mol Life Sci.
2005;
62
1707-23
- 2
Kim D, Park J, Kim J, Han C, Yoon J, Kim N. et al .
Flavonoids as mushroom tyrosinase inhibitors: A fluorescence quenching study.
J Agric Food Chem.
2006;
54
935-41
- 3
Van Welzen P C.
Guioa Cav. (Sapindaceae): Taxonomy, phylogeny, and historical biogeography.
Leiden Bot Ser.
1989;
12
1-315
- 4 Renimel I, Olivier M, André P. Use of Guioa plant extract in cosmetic and pharmaceutical compositions for the treatment of skin
aging. FR Patent 19961220 1998
- 5
Alabdul Magid A, Voutquenne-Nazabadioko L, Litaudon M, Lavaud C.
Acylated farnesyl diglycosides from Guioa crenulata.
.
Phytochemistry.
2005;
66
2714-8
- 6
Yoshizaki M, Fujino H, Masuyama M, Arisawa M, Morita N.
A chemotaxonomic study of flavonoids in the leaves of six Trichosanthes species.
Phytochemistry.
1987;
26
2557-8
- 7
Teng R, Xie H, Li H Z, Liu X, Wang D, Yang C.
Two new acylated flavonoid glycosides from Morina nepalensis var. alba Hand-Mazz.
Magn Reson Chem.
2002;
40
415-20
- 8
Lu Y, Sun Y, Foo L Y, McNabb W C, Molan A L.
Phenolic glycosides of forage legume Onobrychis viciifolia.
.
Phytochemistry.
2000;
55
67-75
- 9
Dini I, Carlo Tenore G, Dini A.
Phenolic constituents of Kancolla seeds.
Food Chem.
2004;
84
163-8
- 10
Nonaka G I, Morimoto S, Nishioka I.
Tannins and related compounds. Part 13. Isolation and structures of trimeric, tetrameric,
and pentameric proanthocyanidins from cinnamon.
J Chem Soc [Perkin I].
1983;
9
2139-45
- 11
Mahato S B, Kundu A P.
Review article number 98: 13C NMR spectra of pentacyclic triterpenoids, a compilation and some salient feature.
Phytochemistry.
1994;
37
1517-75.
- 12
Reynolds W F, McLean S, Poplawski J, Enriquez R G, Escobar L I, Leon I.
Total assignment of 13C and 1H spectra of three isomeric triterpenol derivatives by 2 D NMR: an investigation of
the potential utility of 1H chemical shifts in structural investigations of complex natural products.
Tetrahedron.
1986;
42
3419-28
- 13
Voutquenne L, Lavaud C, Massiot G, Sevenet T, Hadi H A.
Cytotoxic polyisoprenes and glycosides of long-chain fatty alcohols from Dimocarpus fumatus.
.
Phytochemistry.
1999;
50
63-9
- 14
Wong W -H, Kasai R, Choshi W, Nakagawa Y, Mizutani K, Ohtani K. et al .
Acyclic sesquiterpene oligoglycosides from pericarps of Sapindus delavayi.
.
Phytochemistry 1991; 30: 2699 - 702 [and Erratum in Phytochemistry.
1991;
30
4212] and references cited therein
- 15
Agrawal P K.
NMR spectroscopy in the structural elucidation of oligosaccharides and glycosides.
Phytochemistry.
1992;
31
3307-30
- 16
Xie L -P, Chen Q -X, Huang H, Wang H -Z, Zhang R -Q.
Inhibitory effects of some flavonoids on the activity of mushroom tyrosinase.
Biochemistry (Moscow).
2003;
68
487-91
- 17
Kim D -S, Kim S -Y, Moon S -J, Chung J -H, Kim K -H, Cho K -H. et al .
Ceramide inhibits cell proliferation through Akt/PKB inactivation and decreases melanin
synthesis in Mel-Ab cells.
Pigm Cell Res.
2001;
14
110-5
- 18
Shoji T, Masumoto S, Moriichi N, Kobori M, Kanda T, Shinmoto H. et al .
Procyanidin trimers to pentamers fractionated from apple inhibit melanogenesis in
B16 mouse melanoma cells.
J Agric Food Chem.
2005;
53
6105-11
- 19 Kobayashi A, Ouchi A, Kusuoru H, Shibuya Y. Dihydrolupeol derivatives for the promotion
of melanin production. JP Patent 2002003381 2002
- 20 Kuno N, Shinokara G. External preparation for the skin and beautifying agents. WO
Patent 20010330; PCT Int Appl 2001
- 21
Kim D -S, Park S -H, Kwon S -B, Park E -S, Huh C -H, Youn S -W. et al .
Sphingosylphosphorylcholine-induced ERK activation inhibits melanin synthesis in human
melanocytes.
Pigm Cell Res.
2006;
19
146-53
- 22
Adesanya S, Martin M T, Hill B, Dumontet V, Van Tri M, Sévenet T. et al .
Rubiginoside, a farnesyl glycoside from Lepisanthes rubiginosa.
.
Phytochemistry.
1999;
51
1039-41
- 23
Delaude C.
Les Sapindaceae et leurs saponines.
Bull Soc R Sci Liège.
1993;
62
93-120
Dr. Laurence Voutquenne-Nazabadioko
Laboratoire de Pharmacognosie
FRE CNRS 2715
Bât. 18
BP 1039
51687 Reims Cedex 2
France
Phone: +33-3-2691-8208
Fax: +33-3-2691-3596
Email: laurence.voutquenne@univ-reims.fr