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.
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
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
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
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
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
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
