Hirtellanines A and B, a pair of isomeric isoflavonoid derivatives from Campylotropis hirtella and their immunosuppressive activities

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 13, 2009, Pages 3389-3391

  Shou, Qing Yao ^a   Tan, Qing ^a   Shen, Zheng Wu ^a,b  

^a SHANGHAI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE   (China)

^b Basilea Pharmaceutica China Ltd   (China)

Author keywords

Campylotropis hirtella (Franch.) Schindl.; Hirtellanine A; Hirtellanine B; Immunosuppressive activity

Indexed keywords

CAMPYLOTROPIS HIRTELLA EXTRACT; CYCLOSPORIN A; HIRTELLANINE A; HIRTELLANINE B; ISOFLAVONOID; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; B LYMPHOCYTE; CAMPYLOTROPIS HIRTELLA; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG POTENCY; IC 50; IMMUNE DEFICIENCY; IMMUNOSUPPRESSIVE TREATMENT; MEDICINAL PLANT; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PLANT ROOT; STRUCTURE ACTIVITY RELATION; T LYMPHOCYTE;

B-LYMPHOCYTES; FABACEAE; IMMUNOSUPPRESSIVE AGENTS; ISOFLAVONES; PLANT ROOTS; T-LYMPHOCYTES;

CAMPYLOTROPIS; HIRTELLA;

EID: 66349116679     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.05.043     Document Type: Article

References (17)

1. Pharmacopoeia Committee of the People's Republic of China Edit. Pharmacopoeia of the People's Republic of China (1977), People's Hygiene Press, Beijing pp 30-31
2. He X.H., and Xi X.X. Immunology of Traditional Chinese Medicine (2002), People's Military Medical Press, Beijing pp 37-40
3. Ye M., Xie W.D., Lei F., Meng Z., Zhao Y.N., Su H., and Du L.J. Int. Immunopharmacol. 6 (2006) 426
4. Lu X.Z., Xu W.B., and Shen J.X. Zhongguo Zhongyao Zazhi 22 (1997) 680
5. Qin L., Chen X.M., Chen W.X., Yang L., and Zhang C.K. Tianran Chanwu Yanjiu Yu Kaifa 3 (1991) 31
6. Han H.Y., Wang X.H., Wang N.L., Ling M.T., Wong Y.C., and Yao X.S. J. Agric. Food. Chem. 56 (2008) 6928
7. Wen P., Han H.Y., Wang N.L., and Yao X.S. J. Shenyang Pharm. Univ. 25 (2008) 448
8. Han H.Y., Wen P., Liu H.W., Wang N.L., and Yao X.S. Chem. Pharm. Bull. 56 (2008) 1338
9. Isolation of Hirtellanines A and B: The roots of Campylotropis hirtella (Franch.) Schindl. were collected from Yunnan province, China, and authenticated by Professor Zhou Xiujia of Shanghai University of TCM. A voucher specimen had been deposited in the herbarium of the Shanghai University of TCM. The air-dried and comminuted roots of C. hirtella (2 kg) were extracted with 95% EtOH. The EtOH extracts were evaporated under reduced pressure to give a residue (387 g), which was suspended in distilled water and partitioned successively with petroleum ether, EtOAc, and n-BuOH. The EtOAc extract was applied to a silica gel column, eluting with petroleum ether containing increasing amounts of EtOAc. After repeated column chromatography over silica gel eluted with petroleum ether/acetone, petroleum ether/ethyl acetate, and Pharmadex LH-20 eluted with methanol, Hirtellanines A (16 mg), and B (12 mg) were obtained.
10. +.
11. Ferrari F., Messana I., and Goulart Sant'Ana A.E. J. Nat. Prod. 54 (1991) 597
12. Ghirtis K., Pouli N., Marakos P., Skaltsounis A., Leonce S., Caignard D., and Atassi G. Heterocycles 53 (2000) 93
13. +.
14. Rao P.P., and Srimannarayana G. Phytochemistry 19 (1980) 1272
15. Wagner H., Geyer B., Kiso Y., Hikino H., and Rao G.S. Planta Med. 5 (1986) 370
16. Darbarwar M., Sundaramurthy V., and Rao N.V.S. J. Sci. Ind. Res. 35 (1976) 297
17. The two compounds were dissolved in pure dimethyl sulfoxide (DMSO) as a stock solution, and stored at 4 °C. The stock solution was diluted to the needed concentrations with RPMI-1640 supplemented with 10% FBS. The final concentration of DMSO in the culture medium was less than 0.01%, which had no influence on the assays. Splenic lymphocytes were cultured for 48 h with 5 μg/mL of ConA or 10 μg/mL of LPS plus Hirtellanines A and B and Cyclosporin A. Cells were pulsed with 0.5 μCi/well of [3H]-thymidine for 8 h and harvested onto glass filters. The incorporated radioactivity was then counted using a Beta Scintillation Counter (MicroBeta Trilux, PerkinElmer Life Sciences, Boston, MA). Cytotoxicity was assessed by the MTT assay. Briefly, splenic lymphocytes were cultured for 48 h with Hirtellanines A and B and Cyclosporin A. The cells cultured with media alone were used as controls. MTT (5 mg/mL) reagent was added 4 h before the end of culture, and the supernatants were discarded, then cells were lysed with dimethyl sulfoxide (DMSO). O.D. values were read at 570 nm, and the percentage of cell death was calculated.