Download PDF
Planta Med 2011; 77(16): 1811-1817
DOI: 10.1055/s-0030-1271185
Natural Product Chemistry
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Flavonoids from the Roots of Campylotropis hirtella

Qing Tan1 , Sheng Zhang1 , Zhengwu Shen1 , 2
  • 1School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai, People's Republic of China
  • 2Basilea Pharmaceutica China Ltd., Haimen, Jiangsu, People's Republic of China
Further Information

Publication History

received April 7, 2011 revised May 10, 2011

accepted May 11, 2011

Publication Date:
15 June 2011 (online)

Also available at
    Permissions and Reprints

Abstract

Eight new flavonoids, including three pterocarpene derivatives, hirtellanines C–E, two flavanones, hirtellanines F and G, three isoflavanones, hirtellanines H–J, as well as four known compounds were isolated from the roots of Campylotropis hirtella. The structures of the new compounds were elucidated by spectroscopic analyses, including 2D-NMR techniques. Pharmacological investigation indicated that the new compounds, particularly hirtellanines D and G, possessed potent immunosuppressive activities and low relative cytotoxicities.

Key words

Leguminosae - hirtellanines - roots of Campylotropis hirtella - flavonone - isoflavone - pterocarpene - immunosuppressive activities

Supporting Information

References

  • 1 Jiangsu New Medical College .Dictionary of Chinese Materia Medica [M]. Shanghai: Shanghai Scientific and Technic Publishers; 2001: 2396
    Search in Google Scholar
  • 2 Pharmacopoeia Committee of the People's Republic of China Edita .Chinese Materia Medica. Pharmacopoeia of the People's Republic of China. Beijing: People's Hygiene Press; 1978: 30-31
    Search in Google Scholar
  • 3 Qin L, Chen X M, Chen W X. Study on tannins from Campylotropis hirtella.  Nat Prod Res Dev. 1991;  3 31-34
    PubMedSearch in Google Scholar
  • 4 Lu X Z, Xu W B, Shen J X, Han G Q. Chemical studies on Campylotropis hirtella.  Chin J Chin Mater Med. 1997;  22 680-682
    PubMedSearch in Google Scholar
  • 5 Wen P, Han H Y, Wang N L. C-Glycosylfavones and aromatic glycosides from Campylotropis hirtella (Franch.) Schindl.  Asian J Tradit Med. 2007;  2 149-153
    PubMedSearch in Google Scholar
  • 6 Wen P, Han H Y, Wang N L, Yao X S. Studies on chemical constituents of Campylotropis hitella.  Chin Tradit Herb Drugs. 2008;  39 1143-1145
    PubMedSearch in Google Scholar
  • 7 Han H Y, Liu H W, Yao X S. Sesquilignans and dilignans from Campylotropis hitella (Franch.) Schindl.  Nat Prod Res. 2008;  22 990-995
    CrossrefPubMedSearch in Google Scholar
  • 8 Wen P, Han H Y, Wang N L, Yao X S. Flavonoids from Campylotropis hitella (Franch.) Schindl. and their bioactivities.  J Shenyang Pharm Univ. 2008;  25 448-453
    PubMedSearch in Google Scholar
  • 9 Han H Y, Wen P, Liu H W, Wang N L, Yao X S. Coumarins from Campylotropis hirtella (Franch) Schindl. and their inhibitory activity on prostate specific antigen secreted from LNCaP Cells.  Chem Pharm Bull. 2008;  56 1338-1341
    CrossrefPubMedSearch in Google Scholar
  • 10 Han H Y, Wang X H, Wang N L. Lignans isolated from Campylotropis hitella (Franch.) Schindl. decreased prostate specific antigen and androgen receptor expression in LNCaP Cells.  J Agric Food Chem. 2008;  56 6928-6935
    CrossrefPubMedSearch in Google Scholar
  • 11 Shou Q Y, Tan Q, Shen Z W. Hirtellanines A and B, a pair of isomeric isoflavonoid derivatives from Campylotropis hirtella and their immunosuppressive activities.  Bioorg Med Chem Lett. 2009;  19 3389-3391
    CrossrefPubMedSearch in Google Scholar
  • 12 Shou Q Y, Tan Q, Shen Z W. Isoflavonoids from the roots of Campylotropis hirtella.  Planta Med. 2009;  75 1-6
    Thieme ConnectPubMedSearch in Google Scholar
  • 13 Shou Q Y, Fu R Z, Tan Q, Shen Z W. Geranylated flavonoids from the roots of Campylotropis hirtella and their immunosuppressive activities.  J Agric Food Chem. 2009;  57 6712-6719
    CrossrefPubMedSearch in Google Scholar
  • 14 Shibano Y, Henmi A, Matsumoto Y, Kusano G, Mayase T, Hatakeyama Y. Studies on the index compounds for HPLC analysis of Glycyrrhiza uralensis.  Heterocycles. 1997;  45 2053-2060
    CrossrefPubMedSearch in Google Scholar
  • 15 Asai T, Hara N, Kobayashi S, Kohshima S, Fujimoto Y. Geranylated flavanones from the secretion on the surface of the immature fruits of Paulownia tomentosa.  Phytochemistry. 2008;  69 1234-1241
    CrossrefPubMedSearch in Google Scholar
  • 16 Gaffield W. Circular dichroism, optical rotatory dispersion and absolute configuration of flavanones, 3-hydroxyflavanones and their glycosides.  Tetrahedron. 1970;  26 4093-4108
    CrossrefPubMedSearch in Google Scholar
  • 17 Chen L, Jiang W, Hou A J. Novel 2-arylbenzofuran derivatives from Artocarpus petelotii.  Helv Chim Acta. 2008;  89 1000-1007
    PubMedSearch in Google Scholar
  • 18 Annabel S L, Alban A, Nataly B S, Christophe C, Bernard B. Meroterpenes from the ascidian Aplidium aff. densum.  J Nat Prod. 2005;  68 1412-1415
    CrossrefPubMedSearch in Google Scholar
  • 19 He J, Chen L, Heber D, Shi W Y, Lu Q Y. Antibacterial compounds from Glycyrrhiza uralensis.  J Nat Prod. 2006;  69 121-124
    CrossrefPubMedSearch in Google Scholar
  • 20 Osawa K, Yasuda H, Maruyama T, Morita H, Takeya K, Itokawa H. Isoflavanones from the heartwood of Swartzia polyphylla and their antibacterial activity against cariogenic bacteria.  Chem Pharm Bull. 1992;  40 2970-2974
    CrossrefPubMedSearch in Google Scholar
  • 21 Li X C, Joshi A S, ElSohly H N, Khan S I. Fatty acid synthase inhibitors from plants: isolation, structure elucidation and SAR studies.  J Nat Prod. 2002;  65 1909-1914
    CrossrefPubMedSearch in Google Scholar
  • 22 Brink A J, Ral G J H, Engelbrecht J P. Phenolic neorautanenia isoflavanoids the isolation and structures of neoraufurane, three novel isoflavanoids from Neorautanenia edulis.  Tetrahedron. 1974;  30 311-314
    CrossrefPubMedSearch in Google Scholar

Prof. Dr. Zheng-Wu Shen

School of Pharmacy Shanghai
University of Traditional Chinese Medicine

1200 Cailun Road

Shanghai 201203

People's Republic of China

Phone: +86 51 3 82 19 80 01

Fax: +86 51 3 82 19 80 03

Email: jeff_shen_1999@yahoo.com