Identification and quantification of the sedative and anticonvulsant flavone glycoside from Chrysanthemum boreale

다국어 초록 (Multilingual Abstract)

The flowers or leaves of Chrysanthemumboreale (Compositae) have been traditionally used as herbtea to reduce anxiety, insomnia, and stress. Sedative andanticonvulsant activities were evaluated in mice usingpentobarbital-induced sleeping assay and pentylenetetrazole(PTZ)-induced convulsion assay. The flower extractexhibited more potent activities than the extracts of theleaves and stems, and chromatographic isolation yieldedthe five compounds acacetin, linarin, acacetin 7-O-b-Dglucopyranosyl-(1 ? 2)[a-L-rhamnopyranosyl-(1 ? 6)]-b-D-glucopyranoside, chlorogenic acid, and 3,5-di-O-caffeoylquinic acid. These compounds were simultaneouslyanalyzed by HPLC, and the method was validated. Thecontents of linarin, which were shown to be most abundant inC. boreale, were observed in the order of leaf (11.93 mg/g)[flower (8.50 mg/g)[stem (5.60 mg/g). Linarin and itsaglycone, acacetin, exhibited sedative and anticonvulsantactivities in the present in vivo assays. It can be consideredthat linarin is one of the active compounds effective againstanxiety, insomnia, and stress, with acacetin as its activemoiety.

참고문헌 (Reference)

1 Dutar, P., "The septohippocampal pathway : Structure and function of a central cholinergic system" 75 : 393-427, 1995

2 Song, H. J., "The protective effect of eupatilin on indomethacin-induced cell damage in cultured feline ileal smooth muscle cells : Involvement of HO-1 and ERK" 118 : 94-101, 2008

3 Kavvadias, D., "The flavones hispidulin, a benzodiazepine receptor ligand with positive allosteric properties, traverses the blood–brain barrier and exhibits anticonvulsive effects" 142 : 811-820, 2004

4 Crawford, J. M, "The effect upon mice if intraventricular injection of excitant and depressant amino acids" 12 : 1443-1444, 1963

5 Ren, A. N., "Study on bacteriostasis and antivirotic of flowers Chrysanthemum indicum" 6 : 241-244, 1999

6 Do, J. C., "Studies on the constituents of Lycopuslucidus(II)" 22 : 166-170, 1991

7 Ferna´ndez, S., "Sedative and sleep-enhancing properties of linarin, a flavonoidisolated from Valeriana officinalis" 77 : 399-404, 2004

8 Monforte, M. T., "Protective effect of Calamintha officinalis Moench leaves against alcohol-induced gastric mucosa injury in rats. Macroscopic, histologic and phytochemical analysis" 26 : 839-844, 2012

9 Yoo, Y. M., "Pectolinarin and pectolinarigenin of Cirsium setidens prevent the rat hepatic injury caused by D-galactosamine via antioxidant mechanism" 31 : 760-764, 2008

10 Lee, J. R., "New guaianolides from leaves and stems of Chrysanthemum boreale" 69 : 880-882, 2003

11 Ma, Y., "Methanol extract of Longanae Arillus augments modification of GABAergic system" 122 : 245-250, 2009

12 Kim, T. J., "Korean resources plants" The Publication Department of Seoul National University 202-326, 1996

13 Shin, K. H., "Isolation of aldose reductase inhibitors from the flowers of Chrysanthemum boreale" 18 : 65-68, 1995

14 Koo, B. S., "Inhibitory effects of the fragrance inhalation of essential oil from Acorus gramineuson central nervous system" 26 : 978-982, 2003

15 Ribe´reau-Gayon, G., "In vitro and in vivo effects of alpha-acetylenicDOPAand alpha-vinylDOPAon aromaticL-amino acid decarboxylase" 28 : 1331-1335, 1979

16 Lin, L. C., "Immunomodulatory principles of Dichrocephala bicolor" 62 : 405-408, 1999

17 Veitch, N. C., "Flavonoid glycosides of the black locust tree, Robinapseudoacacia(Leguminosae)" 71 : 479-486, 2010

18 Nazaruk, J., "Flavonoid compounds from the flowers of Cirsium rivulare(Jacq. )All" 60 : 87-89, 2003

19 Bouskeia, E., "Effects of oral administration of purified micronized flavonoid fraction on increased microvascular permeability induced by various agents and on ischemia/ reperfusion in diabetic hamsters" 15 : 293-300, 1995

20 Hong, Y. G., "Effect of cumambrin A treatment on blood pressure in spontaneously hypertensive rats" 30 : 226-230, 1999

21 Vogel, H. G., "Drug discovery and evaluation-pharmacological assays" Springer 422-423, 2001

22 Lee, K. D., "Cytotoxicity activity and structural analogues of guaianolide derivatives from the flower of Chrysanthemum boreale L" 46 : 29-32, 2003

23 Cheon, M. S., "Chrysanthemum indicum Linne extract inhibits the inflammatory response by suppressing NF-jB and MAPKs activation in lipopolysaccharide-induced RAW264. 7 macrophages" 122 : 473-477, 2009

24 Kim, Y., "Chrysanthemum boreale Makino extracts on the expression of inducible nitric oxide synthase in RAW264. 7 macrophages" 131 : 550-554, 2010

25 Hee-Juhn Park, "Chemistry and Pharmacological Action of Caffeoylquinic Acid Derivatives and Pharmaceutical Utilization of Chwinamul (Korean Mountainous Vegetable)" 대한약학회 33 (33): 1703-1720, 2010

26 Ja¨ger, A. K., "Bioassayguided isolation of apigenin with GABA-benzodiazepine activity from Tanacetum parthenium" 23 : 1642-1644, 2009

27 Coleta, M., "Assessment of luteolin(3, 4, 5, 7-tetrahydroxyflavone)neuropharmacological activity" 189 : 75-82, 2008

28 Baughman, R. W., "Aspartate and glutamate as possible neurotransmitters of cells in layer 6 of the visual cortex" 287 : 848-850, 1980

29 Croucher, M. J., "Anticonvulsant action of excitation amino acids antagonists" 216 : 899-901, 1982

30 Kim, K. J., "Antibacterial activity and chemical composition of essential oil of Chrysanthemum boreale" 69 : 274-277, 2003

31 Nam, S. H., "Antibacterial activities of extracts from Chrysanthemum boreale M" 38 : 269-272, 1995

32 Lim, H., "Anti-inflammatory activity of pectolinarin isolated from Cirsium chanroenicum" 31 : 2063-2067, 2008

33 Hu, C. Q., "Anti-AIDS agents, 10. Acacetin-7-O-b-D-galactopyranoside, an anti-HIV principle from Chrysanthemum morifolium and a structure-activity correlation with some related flavonoids" 57 : 42-51, 1994

34 Wang, W. P., "Agmatine protects against cell damage induced by NMDA and glutamate in cultured hippocampal neuron" 1084 : 210-216, 2006

35 Pan, M. H., "Acacetin suppressed LPS-induced up-expression of iNOS and COX-2 in murine macrophages and TPA-induced tumor promotion in mice" 72 : 1293-1303, 2006

36 Park, K. H., "A new cytotoxic guaianolide from Chrysanthemum boreale" 80 : 54-56, 2009