Download PDF
Planta Med 2007; 73(8): 782-786
DOI: 10.1055/s-2007-981551
Natural Product Chemistry
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

Inhibitory Constituents of Euscaphis japonica on Lipopolysaccharide-Induced Nitric Oxide Production in BV2 Microglia

Mi Kyeong Lee1 , Hee Young Jeon1 , Ki Yong Lee1 , Seung Hyun Kim1 , Choong Je Ma1 , Sang Hyun Sung1 , Heum-Sook Lee2 , Mi Jung Park3 , Young Choong Kim1
  • 1College of Pharmacy and Research Institute of Pharmaceutical Science, Seoul National University, Seoul, Korea
  • 2Department of Food Science and Technology, Seoul National University of Technology, Seoul, Korea
  • 3Department of Visual Optics, Seoul National University of Technology, Seoul, Korea
Further Information

Publication History

Received: February 1, 2007 Revised: May 17, 2007

Accepted: May 21, 2007

Publication Date:
05 July 2007 (online)

Also available at
    Permissions and Reprints

Abstract

Bioactivity-guided fractionation of the methanolic extract of the aerial parts of Euscaphis japonica (Tunb.) Kantiz (Staphyleaceae), afforded a new compound, p-coumaroyl-D-malic acid 1-methyl ester (1), together with twelve known compounds, 3,7-dihydro-5-octanolide (2), blumenol A (3), megastigmane (4), gallic acid (5), stenophyllin H1 (6), methyl 5,7-dihydroxyoctanoate (7), trans-phytol (8), α-tocopherol (9), kaempferol (10), kaempferol 3-O-β-D-glucopyranoside (11), quercetin (12) and quercetin 3-O-β-D-glucopyranoside (13). Among them, compounds 1 - 5 and 8 - 13 significantly inhibited lipopolysacchride-induced nitric oxide production in murine BV2 microglial cells. Especially, compounds 5, 8, 10 and 12 exerted potent inhibitory activity comparable to that of NAME, used as positive control.

Key words

Euscaphis japonica - p-coumaroyl-D-malic acid 1-methyl ester - Staphyleaceae - nitric oxide - BV2 microglia - anti-inflammatory

References

  • 1 Bredt D S, Snyder S H. Nitric oxide: a physiological messenger molecule.  Annu Rev Biochem. 1994;  63 175-95.
    CrossrefPubMedGoogle Scholar
  • 2 Iadecola C, Delligrino D A, Moskowitz M A, Lassen N A. Nitric oxide synthase inhibition and cerebrovascular regulation.  J Cereb Blood Flow Metab. 1994;  14 175-92.
    CrossrefPubMedGoogle Scholar
  • 3 Contestabile A. Roles of NMDA receptor activity and nitric oxide production in brain development.  Brain Res Brain Res Rev. 2000;  32 476-509.
    CrossrefPubMedGoogle Scholar
  • 4 Bolanos J P, Almeida A, Stewart V, Peuchen S, Land J M, Clark J B. et al . Nitric oxide-mediated mitochondrial damage in the brain: mechanisms and implications for neurodegenerative diseases.  J Neurochem. 1997;  68 2227-40.
    PubMedGoogle Scholar
  • 5 Beckman J S, Crow J P. Pathological implications of nitric oxide, superoxide and peroxynitrite formation.  Biochem Soc Trans. 1993;  21 330-4.
    PubMedGoogle Scholar
  • 6 Felts P A, Woolstone A M, Fernando H B, Asquith S, Gregson N A, Mizzi O J. et al . Inflammation and primary demyelination induced by the intraspinal injection of lipopolysaccharide.  Brain. 2005;  128 1649-66.
    CrossrefPubMedGoogle Scholar
  • 7 Ischiropoulos H, Beckman J S. Oxidative stress and nitration in neurodegeneration: Cause, effect, or association.  J Clin Invest. 2003;  111 63-9.
    PubMedGoogle Scholar
  • 8 Wu D C, Jackson-Lewis V, Vila M, Tieu K, Teismann P, Vadseth C. et al . Blockade of microglial activation is neuroprotective in the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine mouse model of Parkinson disease.  J Neurosci. 2002;  22 763-71.
    PubMedGoogle Scholar
  • 9 Moncada S, Higgs E A. Molecular mechanisms and therapeutic strategies related to nitric oxide.  FASEB J. 1995;  9 1319-30.
    PubMedGoogle Scholar
  • 10 Ishikura N. Flavonol glucosides of Euscaphis japonica .  Phytochemistry. 1971;  10 3332-3.
    CrossrefPubMedGoogle Scholar
  • 11 Konishi T, Otani Y, Kiyosawa S, Fujiwara Y. Constituents of the capsules of Euscaphis japonica (Thunb.) Kantiz.  Chem Pharm Bull. 1996;  44 863-4.
    PubMedGoogle Scholar
  • 12 Takeda Y, Okada Y, Masuda T, Hirata E, Shinzato T, Takushi A. et al . New megastigmane and tetraketide from the leaves of Euscaphis japonica .  Chem Pharm Bull. 2000;  48 752-4.
    CrossrefPubMedGoogle Scholar
  • 13 Kim S H, Sung S H, Choi S Y, Chung Y K, Kim J, Kim Y C. Idesolide: a new spiro compound from Idesia polycarpa .  Org Lett. 2005;  7 3275-7.
    CrossrefPubMedGoogle Scholar
  • 14 Da Cunha F M, Duma D, Assreuy J, Buzzi F C, Niero R, Campos M M. et al . Caffeic acid derivatives: in vitro and in vivo anti-inflammatory properties.  Free Radic Res. 2004;  38 241-53.
    CrossrefPubMedGoogle Scholar
  • 15 Lu Y, Foo L Y. The polyphenol constituents of grape pomace.  Food Chem. 1999;  65 1-8.
    CrossrefPubMedGoogle Scholar
  • 16 Hahn R, Nahrstedt A. High content of hydroxycinnamic acids esterified with (+)-D-malic acid in the upper parts of Fumaria officinalis .  Planta Med. 1993;  59 189-90.
    Article in Thieme ConnectPubMedGoogle Scholar
  • 17 Hahn R, Nahrstedt A. Hydroxycinamic acid derivatives, caffeoylmalic and new caffeoylaldonic acid esters, from Chelidonium majus .  Planta Med. 1993;  59 71-5.
    Article in Thieme ConnectPubMedGoogle Scholar
  • 18 Mori Y, Kageyama H, Suzuki M. Synthesis of (-)-tarchonanthuslactone, a syn-1,3-polyol-derived unsaturated lactone.  Chem Pharm Bull. 1990;  38 2574-6.
    CrossrefPubMedGoogle Scholar
  • 19 Gonzalez A G, Guillermo J A, Ravelo A G, Jimenez I A. 4,5-dihydroblumenol A, new nor-isoprenoid from Perrottetia multiflora .  J Nat Prod. 1994;  57 400-2.
    CrossrefPubMedGoogle Scholar
  • 20 Tian G, Zhang T, Yang F, Ito Y. Separation of gallic acid form Cornus officinalis Sieb. et Zucc by high-speed counter-current chromatography.  J Chromatogr. 2000;  886 309-12.
    CrossrefPubMedGoogle Scholar
  • 21 Tanaka N, Tanaka T, Fujioka T, Fujii H, Mihashi K, Shimomura K. et al . An ellagic compound and iridoids form Cornus capitata root cultures.  Phytochemistry. 2001;  57 1287-91.
    CrossrefPubMedGoogle Scholar
  • 22 Stritzke K, Schulz S, Nishida R. Absolute configuration and synthesis of β- and α-lactones represent in the pheromone system of the giant white butterfly Idea lueconone .  Eur J Org Chem. 2002;  2002 3884-92.
    CrossrefPubMedGoogle Scholar
  • 23 Crownstein A, Burton G W, Hughes L, Ingold K U. Chiral effects on the 13C resonances of α-tocopherol and related compounds - a novel illustration of Newman's ”Rule of six.”  J Org Chem. 1989;  54 560-9.
    CrossrefPubMedGoogle Scholar
  • 24 Arawal P K, Bansal M C, Foo L Y, Markham K R, Porter L J, Thakur R S. Carbon-13 NMR of flavonoid. St. Louis; Elsevier 1989: 152-344.
    Google Scholar
  • 25 Kim H Y, Moon B H, Lee H J, Choi D H. Flavonol glycosides from the leaves of Eucommia ulmoides O. with glycation inhibitory activity.  J Ethnopharmacol. 2004;  93 227-30.
    CrossrefPubMedGoogle Scholar
  • 26 Kim H P, Son K H, Chang H W, Kang S S. Anti-inflammatory plant flavonoids and cellular action mechanisms.  J Pharmacol Sci. 2004;  96 229-45.
    CrossrefPubMedGoogle Scholar
  • 27 Chen Y C, Shen S C, Chen L G, Lee T J, Yang L L. Wogonin, baicalin and baicalein inhibition of inducible nitric oxide synthase and cyclooxygenase-2 gene expression induced by nitric oxide synthase inhibitors and lipopolysaccharide.  Biochem Pharmacol. 2001;  61 1417-27.
    CrossrefPubMedGoogle Scholar
  • 28 Lee M H, Kim J Y, Ryu J H. Prenylflavones from Psoralea corylifolia inhibit nitric oxide synthase expression through the inhibition of IκB-α degradation in activated microglial cells.  Biol Pharm Bull. 2005;  28 2253-57.
    CrossrefPubMedGoogle Scholar
  • 29 Chen Y C, Shen S C, Lee W R, Hou W C, Yang L L, Lee T J. Inhibition of nitric oxide synthase inhibitors and lipopolysaccharide induced inducible NOS and cyclooxygenase-2 gene expression by rutin, quercetin, and quercetin pentacetate in RAW 264.7 macrophages.  J Cell Biochem. 2001;  82 537-48.
    PubMedGoogle Scholar
  • 30 Raso G M, Meli R, Di Carlo G, Pacilio M, Di Carlo R. Inhibition of inducible nitric oxide synthase and cyclooxygenase-2 expression by flavonoids in macrophage J774A. 1.  Life Sci. 2001;  68 921-31.
    CrossrefPubMedGoogle Scholar
  • 31 Fang S H, Rao Y K, Tzeng Y M. Inhibitory effects of flavonol glycosides from Cinnamomum osmophloeum on inflammatory mediators in LPS/INF-gamma-activated murine macrophages.  Bioorg Med Chem. 2005;  13 2381-8.
    CrossrefPubMedGoogle Scholar

Prof. Young Choong Kim

College of Pharmacy and Research Institute of Pharmaceutical Science

Seoul National University

San 56-1

Sillim-Dong

Gwanak-Gu

Seoul 151-742

Korea

Phone: +82-2-880-7842

Fax: +82-2-888-2933

Email: youngkim@snu.ac.kr

    www.thieme-connect.de/ejournals/toc/plantamedica