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Two prenylated and C-methylated flavonoids from Tripterygium wilfordii.

Abstract

Two unusual prenylated and C-methylated flavanones, (±)-5,4'-dihydroxy-2'-methoxy-6',6''- dimethypyrano-(2'',3'':7,8)-6-methyflavanone ( 1) and (2 S)-5,7,4'-trihydroxy-2'-methoxy-8,5'- di(3-methyl-2-butenyl)-6-methyflavanone ( 2), and 10 known compounds were isolated from the stems and roots of TRIPTERYGIUM WILFORDII. Their structures were elucidated based on spectroscopic analyses including 1- and 2-D NMR, HR-ESI-MS, CD, and x-ray crystallography. The anti-inflammatory, antiproliferative, and antibacterial activities of compounds 1 and 2 were investigated. Compound 2 had an inhibitory effect on lipopolysaccharides (LPS)-triggered RAW cell nitric oxide (NO) production, with an IC (50) value of 15.0 ± 0.7  µM. Both compounds showed moderate antiproliferative activity against the tumor cell lines HT-29 and ZR-75-1.

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  • Publisher Full Text
  • Authors+Show Affiliations

    ,

    School of Pharmaceutical Sciences, Peking University, Beijing, People's Republic of China.

    , , , , , ,

    Source

    Planta medica 76:14 2010 Oct pg 1596-9

    MeSH

    Anti-Bacterial Agents
    Anti-Inflammatory Agents
    Cell Line, Tumor
    Cell Proliferation
    Crystallography, X-Ray
    Escherichia coli
    Flavanones
    Flavonoids
    HT29 Cells
    Humans
    Microbial Sensitivity Tests
    Nuclear Magnetic Resonance, Biomolecular
    Plant Roots
    Plant Stems
    Spectrometry, Mass, Electrospray Ionization
    Tripterygium

    Pub Type(s)

    Letter
    Research Support, Non-U.S. Gov't

    Language

    eng

    PubMed ID

    20309799

    Citation

    TY - JOUR T1 - Two prenylated and C-methylated flavonoids from Tripterygium wilfordii. AU - Zeng,Feng, AU - Wang,Wei, AU - Wu,Yunshan, AU - Dey,Moul, AU - Ye,Min, AU - Avery,Mitchell A, AU - Khan,Ikhlas A, AU - Guo,De-an, Y1 - 2010/03/22/ PY - 2010/3/24/entrez PY - 2010/3/24/pubmed PY - 2011/2/23/medline SP - 1596 EP - 9 JF - Planta medica JO - Planta Med. VL - 76 IS - 14 N2 - Two unusual prenylated and C-methylated flavanones, (±)-5,4'-dihydroxy-2'-methoxy-6',6''- dimethypyrano-(2'',3'':7,8)-6-methyflavanone ( 1) and (2 S)-5,7,4'-trihydroxy-2'-methoxy-8,5'- di(3-methyl-2-butenyl)-6-methyflavanone ( 2), and 10 known compounds were isolated from the stems and roots of TRIPTERYGIUM WILFORDII. Their structures were elucidated based on spectroscopic analyses including 1- and 2-D NMR, HR-ESI-MS, CD, and x-ray crystallography. The anti-inflammatory, antiproliferative, and antibacterial activities of compounds 1 and 2 were investigated. Compound 2 had an inhibitory effect on lipopolysaccharides (LPS)-triggered RAW cell nitric oxide (NO) production, with an IC (50) value of 15.0 ± 0.7  µM. Both compounds showed moderate antiproliferative activity against the tumor cell lines HT-29 and ZR-75-1. SN - 1439-0221 UR - https://www.unboundmedicine.com/medline/citation/20309799/Two_prenylated_and_C_methylated_flavonoids_from_Tripterygium_wilfordii_ L2 - http://www.thieme-connect.com/DOI/DOI?10.1055/s-0029-1241017 ER -