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DOI: 10.1055/s-0029-1240911
© Georg Thieme Verlag KG Stuttgart · New York
Chemical Constituents of Alnus firma and Their Inhibitory Activity on Lipopolysaccharide-Induced Nitric Oxide Production in BV2 Microglia
Publikationsverlauf
received October 16, 2009
revised January 13, 2010
accepted January 19, 2010
Publikationsdatum:
01. März 2010 (online)
Abstract
A methanolic extract of Alnus firma barks (Betulaceae) significantly attenuated nitric oxide production in lipopolysaccharide-stimulated BV2 microglia. Two new compounds, characterized as 4-hydroxy-2,6-dimethoxyphenyl 6′-O-syringoyl-β-D-glucopyranoside (1) and 4-hydroxy-2,6-dimethoxyphenyl 6′-O-vanilloyl-β-D-glucopyranoside (2), were isolated from the barks of A. firma using bioactivity-guided fractionation, together with two known phenolic glycosides (3, 4) and 11 known diarylheptanoids (5–15). Among these compounds, 1–4 and 6–11 showed significant inhibitory effect on lipopolysaccharide-induced nitric oxide production in BV2 microglial cells at concentrations ranging from 10 µM to 100 µM.
Key words
Alnus firma (Betulaceae) - phenolic glycosides - diarylheptanoids - nitric oxide - BV2 microglia - lipopolysaccharide
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References
- 1 Bredt D S, Snyder S H. Nitric oxide: a physiologic messenger molecule. Annu Rev Biochem. 1994; 63 175-195
- 2 Bubgon O, Schaad N C, Schorderet M. Nitric oxide modulates endogenous dopamine release in bovine retina. Neuroreport. 1994; 5 401-404
- 3 Bolaños J P, Almedia A, Stewart V, Peuchen S, Land J M, Clark J B, Heales S J. Nitric oxide-mediated mitochondrial damage in the brain: mechanisms and implications for neurodegenerative diseases. J Neurochem. 1997; 68 2227-2240
- 4 Fernández-Viazarra P, Fernández A P, Castro-Blanco S, Encinas J M, Serrano J, Bentura M L, Muñoz P, Martínez-Murillo R, Rodrigo J. Expression of nitric oxide system in clinically evaluated cases of Alzheimer's disease. Neurobiol Dis. 2004; 15 287-305
- 5 Ischiropoulos H, Beckman J S. Oxidative stress and nitration in neurodegeneration: cause, effect, or association. J Clin Invest. 2003; 111 163-169
- 6 Moncada S, Higgs E A. Molecular mechanisms and therapeutic strategies related to nitric oxide. FASEB J. 1995; 9 1319-1330
- 7 Kim T J. Korean resources plants, Vol. 1. Seoul; Seoul National University Press 1996: 94
- 8 Yu Y B, Miyashiro H, Nakamura N, Hattori M, Park J C. Effects of triterpenoids and flavonoids isolated from Alnus firma on HIV-1 viral enzymes. Arch Pharm Res. 2007; 30 820-826
- 9 Asakawa Y. Chemical constituents of Alnus firma (Betulaceae). I. Phenyl propane derivatives isolated from Alnus firma. Bull Chem Soc Jpn. 1970; 43 2223-2229
- 10 Hiltunen E, Pakkanen T T, Alvila L. Phenolic compounds in silver birch (Betula pendula Roth) wood. Holzforschung. 2006; 60 519-527
- 11 Yang X W, Wang J S, Ma Y L, Xiao H T, Zuo Y Q, Lin H, He H P, Li L, Hao X J. Bioactive phenols from the leaves of Baccaurea ramiflora. Planta Med. 2007; 73 1415-1417
- 12 Kuroyanagi M, Shimomae M, Nagashima Y, Muto N, Okuda T, Kawahara N, Nakane T, Sano T. New diarylheptanoids from Alnus japonica and their antioxidative activity. Chem Pharm Bull. 2005; 53 1519-1523
- 13 Sunnerheim-Sjöberg K, Knutsson P. Platyphylloside: metabolism and digestibility reduction in vitro. J Chem Ecol. 1995; 21 1339-1347
- 14 Sunnerheim K, Palo R T, Theander O, Knutsson P G. Chemical defense in birch. Platyphylloside: a phenol from Betula pendula inhibiting digestibility. J Chem Ecol. 1988; 14 549-560
- 15 Šmite E, Lundgren L N, Andersson R. Arylbutanoid and diarylheptanoid glycosides from inner bark of Betula pendula. Phytochemistry. 1993; 32 365-369
- 16 Giang P M, Son P T, Matsunami K, Otsuka H. New diarylheptanoids from Amomum muricarpum Elmer. Chem Pharm Bull. 2006; 54 139-140
- 17 Wada H, Tachibana H, Fuchino H, Tanaka N. Three new diarylheptanoid glycosides from Alnus japonica. Chem Pharm Bull. 1998; 46 1054-1055
- 18 Gonzalez-laredo R F, Chen J, Karchesy Y M, Karchesy J J. Four new diarylheptanoid glycosides from Alnus rubra bark. Nat Prod Lett. 1999; 13 75-80
- 19 De Leo M, Braca A, De Tommasi N, Norscia I, Morelli I, Battinelli L, Mazzanti G. Phenolic compounds from Baseonema acuminatum leaves: isolation and antimicrobial activity. Planta Med. 2004; 70 841-846
- 20 Kim S H, Jang S D, Lee K Y, Sung S H, Kim Y C. Chemical constituents isolated from Polygala japonica leaves and their inhibitory effect on nitric oxide production in vitro. J Enzyme Inhib Med Chem. 2009; 24 230-233
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