Planta Med 2010; 76 - P42
DOI: 10.1055/s-0030-1251804

Two Prenylated and C-methylated Flavonoids from Tripterygium wilfordii Hook. F. (Celastraceae)

F Zeng 1, W Wang 2, YS Wu 3, M Ye 1, MA Avery 3, IA Khan 2, DA Guo 1, 4
  • 1School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100083, P. R. China
  • 2Sino-US TCM Research Center, National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, University of Mississippi, University, MS 38677, USA
  • 3Department of Medicinal Chemistry, University of Mississippi, University, MS 38677, USA
  • 4Shanghai Research Center for Modernization of TCM, Shanghai Institute of Materia Medica, CAS, Guo Shoujing Road 199, Shanghai 201203, P. R. China

Tripterygium wilfordii Hook. F. (Celastraceae) grows mainly in the southern part of China. The debarked stem plus roots of T. wilfordii, named as „Lei gong teng“, is famous for its anti-inflammatory and immune system regulating activities. „Lei gong teng“ has been used clinically against autoimmune system disease such as rheumatoid arthritis (RA), systemic lupus erythematosus (SLE), multiple sclerosis, Crohn's Disease and lupus in China [1–3]. Previous photochemical investigations reported that many sesquiterpenes, diterpenes and tripterpenes were isolated from Tripterygium species with anti-inflammatory, anti-tumor, anti-fertility, insecticidal and anti neurodegenerative activities [4]. Our ongoing phytochemical study on T. wilfordii resulted in the isolation of two unusual prenylated and C-methylated flavonones (±)-5,4′-dihydroxy-2′-methoxy-6′,6((Prime))-dimethypyrano-(2((Prime)),3((Prime)):7,8)-6-methyflavanone (1) and (2S)-5,7,4′-trihydroxy-2′-methoxy-8,5′-di(3-methyl-2-butenyl)-6-methyflavanone (2), along with 10 known compounds, namely, friedelin, betulinic acid, β-amyrin, oleanolic acid, kaempferol and β-sitosterol, n-hexadecanoic acid, methy hexadecanoate, n-octadecanoicacid and n-tritriacontanoic acid were isolated. Their structures were elucidated based on the spectroscopic analyses including 1, 2-D NMR, HRESI-MS, CD and X-ray crystallography.

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Acknowledgements: This work was supported by program for Changjiang Scholars and Innovation Team in University (No. 985–2-063–112) and the Cultivation Fund of the Key Scientific and Technical Innovation Project, Ministry of Education of China (No. 104218). Fellowship from the Chinese Scholarship Council is gratefully acknowledged. Reference: [1] Tao X, Lipsky PE (2000) Rheum Dis Clin North Am 26: 29–50. [2] Sylvester J, Liacini A, et al. (2001) Mol Pharmacol 59: 1196–205. [3] Ren JA, Tao QS, et al. (2007) Dig Dis Sci 52: 1790–1797. [4] Brinker AM, Ma J, et al. (2007) Phytochem 68: 732–766.