Abstract
From the MeOH extract of the flowers of Chrysanthemum sinense, a new flavone glucoside, acacetin 7-O-(3-O-acetyl-β-D-glucopyranoside) (1), has been isolated together with 27 known compounds including flavonoids, caffeoylquinic acid derivatives, phenolics, and a monoterpenoid glucoside. Their structures were elucidated on the basis of spectroscopic data. Compounds 1 - 15, 20 - 24, and 27 displayed significant xanthine oxidase inhibitory activity in a concentration-dependent manner, and compounds 2 - 11 and 22 showed more potent inhibitory activity, with IC50 values ranging from 0.13 to 2.31 μM, than that of a positive control allopurinol (IC50 = 2.50 μM). The kinetic study indicated that 1 - 15 and 20 - 24 displayed competitive-type inhibition like that of allopurinol, while 27 displayed a mixed-type inhibition.
Key words
Chrysanthemum sinense
- Asteraceae - acacetin 7-O-(3-O-acetyl-β-D-glucopyranoside) - flavonoids - caffeoylquinic acid - phenolics - Xanthine oxidase inhibition
References
-
1
Oettl K, Reibnegger G.
Pteridines as inhibitors of xanthine oxidase: structural requirements.
Biochim Biophys Acta.
1999;
1430
387-95
-
2
Ishibuchi S, Morimoto H, Oe T, Ikebe T, Inoue H, Fukunari A. et al .
Synthesis and structure-activity relationships of 1-phenylpyrazoles as xanthine oxidase inhibitors.
Bioorg Med Chem Lett.
2001;
11
879-82
-
3
Cos P, Ying L, Calomme M, Hu J P, Cimanga K, Van Poel B. et al .
Structure-activity relationship and classification of flavonoids as inhibitors of xanthine oxidase and superoxide scavengers.
J Nat Prod.
1998;
61
71-6
-
4 Do T L. Vietnamese Medicinal Plants. Hanoi; Medicine Publisher 2001: p 604
-
5
Nguyen M TT, Awale S, Tezuka Y, Tran L Q, Watanabe H, Kadota S.
Xanthine oxidase inhibitory activity of Vietnamese medicinal plants.
Biol Pharm Bull.
2004;
27
1414-21
-
6 Harborne J B, Mabry T J. The flavonoids: advances in research, 1st Edition. Cambridge; Cambridge University Press 1982: pp 52-130
-
7
Wollenweber E, Vetschera K M, Ivancheva S, Kuzmanov B.
Flavonoid aglycones from the leaf surfaces of some Achillea species.
Phytochemistry.
1987;
26
181-2
-
8
Marco J A, Barbera O, Rodriguez S, Domingo C, Adell J.
Flavonoids and other phenolics from Artemisia hispanica
.
Phytochemistry.
1988;
27
3155-9
-
9
Martinez-Vazquez M, Garcia H MV, Toscano R A, Perez G E.
Methylated flavones from Conoclidium greggii
.
J Nat Prod.
1993;
56
1410-3
-
10
Mues R, Timmermann B N, Ohno N, Mabry T J.
6-Methoxyflavonoids from Brickellia californica
.
Phytochemistry.
1979;
18
1379-83
-
11
Sanchez A R, Vazquez P.
Quinic acid ester from Isertia haenkeana
.
Phytochemistry.
1991;
30
311-3
-
12
Pauli G , Poetsch F, Nahrstedt A.
Structure assignment of natural quinic acid derivatives using proton nuclear magnetic resonance techniques.
Phytochem Anal.
1998;
9
177-85
-
13
Saleh N AM, Elnegoumy S I, Abouzaid M M.
Flavonoids of Artemisia judaica, A. monosperma and A. herba-alba
.
Phytochemistry.
1987;
26
3059-64
-
14
Gongora L, Giner R M, Manez S, Recio M C, Rios J L.
Phagnalon rupestre as a source of compounds active on contact hypersensitivity.
Planta Med.
2002;
68
561-4
-
15
Basnet P, Matsushige K, Hase K, Kadota S, Namba T.
Four di-O-caffeoyl quinic acid derivatives from propolis. Potent hepatoprotective activity in experimental liver injury model.
Biol Pharm Bull.
1996;
19
1479-84
-
16
Guz N R, Stermitz F R.
Synthesis and structures of regioisomeric hydnocarpin-type flavonolignans.
J Nat Prod.
2000;
63
1140-5
-
17
Pauli G F, Kuczkowiak U, Nahrstedt A.
Solvent effects in the structure dereplication of caffeoyl quinic acids.
Magn Reson Chem.
1999;
37
827-36
-
18
Silva F AM, Borges F, Guimaraes C, Lima J LMC, Matos C, Reis S.
Phenolic acids and derivatives: studies on the relationship among structure, radical scavenging activity, and physicochemical parameters.
J Agric Food Chem.
2000;
48
2122-6
-
19
Mpondo E M, Garcia J, Chulia A J, Mariotte A M.
A new C13 glycoside from Gentiana pneumonanthe
.
Planta Med.
1989;
55
492
-
20
Hara S, Okabe H, Mihashi K.
Gas-liquid chromatography separation of aldose enantiomers as trimethylsilyl ethers of methyl 2-(polyhydroxyalkyl)-thiazolidine-4(R)-carboxylates.
Chem Pharm Bull.
1987;
35
501-6
-
21
Noro T, Oda Y, Miyase T, Ueno A, Fukushima S.
Inhibitors of xanthine oxidase from the flowers and buds of Daphne genkwa
.
Chem Pharm Bull.
1983;
31
3984-7
-
22
Borges F, Fernandes E, Roleira F.
Progress towards the discovery of xanthine oxidase inhibitors.
Curr Med Chem.
2002;
9
195-217
Prof. Dr. Shigetoshi Kadota
Institute of Natural Medicine
Toyama Medical and Pharmaceutical University
2630 Sugitani
Toyama 930-0194
Japan
Phone: +81-76-434-7625
Fax: +81-76-434-5059
Email: kadota@ms.toyama-mpu.ac.jp