Download PDF
Planta Med 2009; 75(8): 843-847
DOI: 10.1055/s-0029-1185376
Natural Product Chemistry
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

Isolation of Two New Prenylflavonols from Epimedium brevicornum and their Effects on Cytokine Production in vitro

Guo-Jun Luo1 , Xin-Xin Ci2 , Rong Ren1 , Zhao-Yuan Wu1 , Hong-Mei Li1 , Hai-Zhou Li1 , Rong-Tao Li1 , Xu-Ming Deng2
  • 1College of Life Science and Technology, Kunming University of Science and Technology, Kunming, Yunnan, P. R. China
  • 2Department of Veterinary Pharmacology, College of Animal Science and Veterinary Medicine, Jilin University, Changchun, Jilin, P. R. China
Further Information

Publication History

received Nov. 6, 2008 revised January 12, 2009

accepted January 18, 2009

Publication Date:
25 February 2009 (online)

    Permissions and Reprints

Abstract

In an attempt to search for bioactive natural products, two new prenylflavonols, 2′′-hydroxy-3′′-en-anhydroicaritin (1) and 2′′-hydroxy-β-anhydroicaritin (2), were isolated from the Chinese medicinal herb Epimedium brevicornum. Their structures were determined by 1D and 2D NMR spectroscopic analysis. The effects of compounds 1 and 2 on cytokine production in vitro were investigated. Compound 1 could significantly downregulate tumor necrosis factor-α (TNF-α) production and increase interleukin-10 (IL-10) production. These results suggested that compound 1 may have anti-inflammatory activity in lipopolysaccharide (LPS)-stimulated mouse macrophages. In addition, the biogenetic relationships among compounds 1 and 2 are discussed.

Key words

Epimedium brevicornum - Berberidaceae - prenylflavonol - anti‐inflammatory - biogenetic relationship

References

  • 1 Delectis Florae Reipublicae Popularis Sinicae Agendae Academiae Sinicae .Flora reipublicae popularis sinicae. Beijing; Science Press 2001: 262
    Google Scholar
  • 2 Zhang Y F, Yu Q H. The anti-inflammatory effects of total flavonoids of epimedium.  J Shengyang Pharm Univ. 1999;  16 122-124
    PubMedGoogle Scholar
  • 3 Yap S P, Shen P, Butler M S, Gong Y, Loy C J, Yong E L. New estrogenic prenylflavone from Epimedium brevicornum inhibits the growth of breast cancer cells.  Planta Med. 2005;  71 114-119
    Article in Thieme ConnectPubMedGoogle Scholar
  • 4 Pan Y, Zhang W Y, Xia X, Kong L D. Effects of icariin on hypothalamic-pituitary-adrenal axis and cytokine levels in stressed Sprague-Dawley rats.  Biol Pharm Bull. 2006;  29 2399-2403
    CrossrefPubMedGoogle Scholar
  • 5 Wu B, Yan S, Lin Y, Wang Q, Yang Y, Yang G J, Shen Z Y, Zhang W D. Metabonomic study on ageing: NMR-based investigation into rat urinary metabolites and the effect of the total flavone of Epimedium.  Mol Biosyst. 2008;  4 855-861
    CrossrefPubMedGoogle Scholar
  • 6 Cai W J, Zhang X M, Huang J H. Effects of epimedium flavonoids in retarding aging of C. elegans.  Zhongguo Zhong Xi Yi Jie He Za Zhi. 2008;  28 522-525
    PubMedGoogle Scholar
  • 7 Meng F H, Li Y B, Xiong Z L, Jiang Z M, Li F M. Osteoblastic proliferative activity of Epimdium brevicornum Maxim.  Phytomedicine. 2005;  12 189-193
    CrossrefPubMedGoogle Scholar
  • 8 Chung B H, Kim J D, Kim C K. Icariin stimulates angiogenenesis by activating the MEK/ERK- and P13K/AKt/eNOS-dependent signal pathways in human endothelial cells.  Biochem Biophys Res Commun. 2008;  376 404
    CrossrefPubMedGoogle Scholar
  • 9 Mizuno M, Iinuma M, Tanaka T. Flavonol glycosides in the roots of Epimedium diphyllum.  Phytochemistry. 1988;  27 3645
    CrossrefPubMedGoogle Scholar
  • 10 Ding P L, Chen D F, Bastow K F, Nyarko A K, Wang X, Lee K H. Cytotoxic isoprenylated flavonoids from the roots of Sophora flavescens.  Helv Chim Acta. 2004;  87 2574-2580
    CrossrefPubMedGoogle Scholar
  • 11 Guo B L, Li W K, Yu J G, Xiao P G. Brevicornin, a flavonol from Epimedium brevicornum.  Phytochemistry. 1996;  41 991-992
    CrossrefPubMedGoogle Scholar
  • 12 Tian X M, Chen S Z, Li T, Tu P F. Three new isoflavonoids from the aerial parts of Ammopiptanthus mongolicus.  Helv Chim Acta. 2008;  91 1015-1022
    CrossrefPubMedGoogle Scholar
  • 13 Tahara S, Ingham I L, Miztani J. Identification of an epoxy-intermediate resulting from the fungal metabolism of a prenylated isoflavone.  Phytochemistry. 1989;  28 2079-2084
    CrossrefPubMedGoogle Scholar
  • 14 Tanaka M, Tahara S. Fad-dependent epoxidase as a key enzyme in fungal metabolism of prenylated flavonoids.  Phytochemistry. 1997;  46 433-439
    CrossrefPubMedGoogle Scholar
  • 15 Wang H, Liao H, Ochani M, Justiniani M, Lin X C, Yang L H, Wang H C, Metz C. Cholinergic agonists inhibit HMGB1 release and improve survival in experimental sepsis.  Nat Med. 2004;  10 1216-1221
    CrossrefPubMedGoogle Scholar
  • 16 Reimold A M. TNF-alpha as therapeutic target: new drugs, more applications.  Curr Drug Targets Inflamm Allergy. 2002;  1 377-392
    CrossrefPubMedGoogle Scholar
  • 17 Dinarello C A. Anti-cytokine therapeutics and infections.  Vaccine. 2003;  21 24-34
    CrossrefPubMedGoogle Scholar
  • 18 Gérard C, Bruyns C, Marchant A, Abramowicz D, Vandenabeele P, Delvaux A, Fiers W, Goldman M, Velu T. Interleukin 10 reduces the release of tumor necrosis factor and prevents lethality in experimental endotoxemia.  J Exp Med. 1993;  177 547-550
    CrossrefPubMedGoogle Scholar
  • 19 Ertel W, Keel M, Steckholzer U, Trentz O. Interleukin-10 attenuates the release of proinflammatory cytokines but depresses splenocyte functions in murine endotoxemia.  Arch Surg. 1996;  131 51-56
    PubMedGoogle Scholar
  • 20 Grutz G. New insights into the molecular mechanism of interleukin-10-mediated immunosuppression.  J Leukoc Biol. 2005;  77 3-15
    PubMedGoogle Scholar

Prof. Rong-Tao Li
Xu-Ming Deng

College of Life Science and Technology
Kunming University of Science and Technology

Kunming

Yunnan 650224

People's Republic of China

Phone: + 86 8 71 38 01 01 82 01

Fax: + 86 87 13 80 11 91

Email: rongtaolikm@yahoo.cn

      >