Planta Medica, Inhaltsverzeichnis Planta Med 2010; 76(10): 1007-1010DOI: 10.1055/s-0029-1240911 Natural Product Chemistry Letters © 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 Min A. Lee1 , Hee Kyoung Lee2 , Seung Hyun Kim2 , Young Choong Kim1 , Sang Hyun Sung1 1College of Pharmacy and Research Institute of Pharmaceutical Science, Seoul National University, Seoul, Korea 2Institute for Life Science, ElcomScience Co., Ltd., Seoul, Korea Artikel empfehlen Abstract Artikel einzeln kaufen Erratum zu diesem Artikel: Erratum for: Chemical Constituents of Alnus firma and Their Inhibitory Activity on Lipopolysaccharide-Induced Nitric Oxide Production in BV2 MicrogliaPlanta Med 2010; 76(10): E3-E3DOI: 10.1055/s-0030-1249808 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 Volltext Referenzen 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 Prof. Dr. Sang Hyun Sung College of Pharmacy and Research Institute of Pharmaceutical SciencesSeoul National University 599 Gwanak-ro Gwanak-gu Seoul 151–742 Korea Telefon: + 82 28 80 78 59 Fax: + 82 28 77 78 59 eMail: shsung@snu.ac.kr Zusatzmaterial Zusatzmaterial www.thieme-connect.de/ejournals/toc/plantamedica