Bioactivity-guided isolation of polyacetylenes with inhibitory activity against NO production in LPS-activated RAW264.7 macrophages from the rhizomes of Atractylodes macrocephala

Journal of Ethnopharmacology

Volumn 151, Issue 2, 2014, Pages 791-799

  Yao, Chun Mei ^a   Yang, Xiu Wei ^a  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

Author keywords

3 (4 5 Dimethyl 2 thiazolyl) 2 5 diphenyl 2H tetrazolium bromide; 1H 1H correlated spectroscopy; 1H 1H COSY; Abbreviations; AMR; AO I; AO III; atractylenolide I; atractylenolide III; Atractylodis Macrocephalae Rhizoma; BuOH; CC; CHX; column chromatography; cyclohexane; ethanol; ethyl acetate; EtOAc; EtOH; heteronuclear multiple bond correlation; heteronuclear single quantum correlation; high performance liquid chromatography; high resolution electric spray ion mass spectrum; HMBC; HPLC; HRESIMS; HSQC; IND; indomethacin; L N6 (1 iminoethyl) lysine; L NIL; lipopolysaccharides; LPS; MTT; n butanol; nitric oxide; NMR; NO; nuclear magnetic resonance

Indexed keywords

(1)H-(1)H CORRELATED SPECTROSCOPY; (1)H-(1)H COSY; 14-ACETOXY-12-SENECIOYLOXYTETRADECA-2E,8E,10E-TRIEN-4,6-DIYN-1-OL (PUBCHEM CID: 14448076); 14-ACETOXY-12-Α-METHYLBUTYRYLTETRADECA-2E,8E,10E-TRIEN-4,6-DIYNE-1-OL (PUBCHEM CID: 5319529); 14-ACETOXY-12-Α-METHYLBUTYRYLTETRADECA-2E,8Z,10E-TRIEN-4,6-DIYNE-1-OL (PUBCHEM CID: 5319530); 14-ACETOXY-12-Β-METHYLBUTYRYLTETRADECA-2E,8E,10E-TRIEN-4,6-DIYNE-1-OL (PUBCHEM CID: 14586258); 14-Α-METHYLBUTYRYLTETRADECA-2E,8E,10E-TRIEN-4,6-DIYNE-1-OL (PUBCHEM CID: 5319531); 14-Β-METHYLBUTYRYLTETRADECA-2E,8E,10E-TRIEN-4,6-DIYNE-1-OL (PUBCHEM CID: 11544212); 3-(4,5-DIMETHYL-2-THIAZOLYL)-2,5-DIPHENYL-2H-TETRAZOLIUM BROMIDE; AMR; ANTI-INFLAMMATORY; AO-I; AO-III; ATRACTYLENOLIDE I; ATRACTYLENOLIDE III; ATRACTYLODES MACROCEPHALA; ATRACTYLODIS MACROCEPHALAE RHIZOMA; BUOH; CC; CHX; COLUMN CHROMATOGRAPHY; COMPOSITAE; CYCLOHEXANE; ETHANOL; ETHYL ACETATE; ETOAC; ETOH; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR SINGLE QUANTUM CORRELATION; HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH-RESOLUTION ELECTRIC SPRAY ION MASS SPECTRUM; HMBC; HPLC; HRESIMS; HSQC; IND; INDOMETHACIN; L-N(6)-(1-IMINOETHYL)-LYSINE; L-NIL; LIPOPOLYSACCHARIDES; LPS; MTT; N-BUTANOL; NITRIC OXIDE; NMR; NO; NUCLEAR MAGNETIC RESONANCE; POLYACETYLENES;

ANIMALS; ANTI-INFLAMMATORY AGENTS; ATRACTYLODES; CELL LINE; CELL SURVIVAL; LIPOPOLYSACCHARIDES; MACROPHAGES; MICE; NITRIC OXIDE; PLANT EXTRACTS; POLYACETYLENES; RHIZOME;

EID: 84895077265     PISSN: 03788741     EISSN: 18727573     Source Type: Journal    
DOI: 10.1016/j.jep.2013.10.005     Document Type: Article

References (35)

1. Y.H. Chang, C.T. Kim, M.H. Jung, Y.H. Lim, S.H. Lee, and S.J. Kang Inhibition of melanogenesis by selina-4(14),7(11)-dien-8-one isolated from atractylodis rhizoma alba Biol. Pharm. Bull. 30 2007 719 723
2. Z.L. Chen The acetylenes from Atractylodes macrocephala Planta Med. 53 1987 493 494
3. Z.L. Chen Chemical constituents of Atractylodes macrocephala. II. α-Methylbutyryl derivatives of atractylentriol Acta Chim. Sin. 47 1989 1022 1024
4. H.J. Choi, S.J. Bae, N.D. Kim, J.H. Jung, and Y.H. Choi Induction of apoptosis by dideoxypetrosynol A, a polyacetylene from the sponge petrosia sp.; in human skin melanoma cells Int. J. Mol. Med. 14 2004 1091 1096
5. H.Y. Dong, Y.L. Dong, L.C. He, and W.J. Pei Studies on constituents and anti-inflammatory activity of Rhizoma Atractylodis macrocephalae Chin. Pharm. J. 42 2007 1055 1058
6. H.Y. Dong, L.C. He, M. Huang, and Y.L. Dong Anti-inflammatory components isolated from Atractylodes macrocephala Koidz Nat. Prod. Res. 22 2008 1418 1427
7. 15N]nitrate in biological fluids Anal. Biochem. 126 1982 131 138
8. F. Herrmann, R. Hamoud, F. Sporer, A. Tahrani, and M. Wink Carlina oxide - a natural polyacetylene from Carlina acaulis (Asteraceae) with potent antitrypanosomal and antimicrobial properties Planta Med. 77 2011 1905 1911
9. B.S. Huang, J.S. Sun, and Z.L. Chen Isolation and identification of atractylenolide IV from Atractylodes macrocephala Koidz Acta Bot. Sin. 34 1992 614 617
10. H. Jiang, J. Shi, and Y.Y. Li Screening for compounds with aromatase inhibiting activities from Atractylodes macrocephala Koidz Molecules 16 2011 3146 3151
11. T.H. Kang, J.Y. Bang, M.H. Kim, I.C. Kang, H.M. Kim, and H.J. Jeong Atractylenolide III, a sesquiterpenoid, induces apoptosis in human lung carcinoma A549 cells via mitochondria-mediated death pathway Food Chem. Toxicol. 49 2011 514 519
12. C.K. Kim, M.H Kim, S.D. Oh, S.M. Lee, B. Sun, G.S. Choi, S.K. Kim, H.S. Bae, C.H. Kang, and B.I. Min Effects of Atractylodes macrocephala Koidzumi rhizome on 3T3-L1 adipogenesis and an animal model of obesity J. Ethnopharmacol. 137 2011 396 402
13. J. Kitajima, A. Kamoshita, T. Ishikawa, A. Takano, T. Fukuda, S. Isoda, and Y. Ida Glycosides of Atractylodes ovata Chem. Pharm. Bull. 51 2003 1106 1108
14. Y.C. Kuo, Y.L. Lin, C.P. Huang, J.W. Shu, and W.J. Tsai A tumor cell growth inhibitor from Saposhnikovae divaricata Cancer Investig. 20 2002 955 964
15. J.C. Lee, K.Y. Lee, Y.O. Son, K.C. Choi, J. Kim, S.H. Kim, G.H. Chung, and Y.S. Jang Stimulating effects on mouse splenocytes of glycoproteins from the herbal medicine A. macrocephala Phytomedicine 14 2007 390 395
16. C.Q. Li, L.C. He, H.Y. Dong, and J.Q. Jin Screening for the anti-inflammatory activity of fractions and compounds from Atractylodes macrocephala Koidz J. Ethnopharmacol. 114 2007 212 217
17. C.Q. Li, L.C. He, and J.Q. Jin Atractylenolide I and atractylenolide III inhibit lipopolysaccharide-induced TNF-α and NO production in macrophages Phytother. Res. 21 2007 347 353
18. H.X. Li, T. O'Neill, D. Webster, J.A. Johnson, and C.A. Gray Anti-mycobacterial diynes from the canadian medicinal plant Aralia nudicaulis J. Ethnopharmacol. 140 2012 141 144
19. B.T. Metzger, D.M. Barnes, and J.D. Reed Purple carrot (Daucus carota L.) polyacetylenes decrease lipopolysaccharide-induced expression of inflammatory proteins in macrophage and endothelial cells J. Agric. Food Chem. 56 2008 3554 3560
20. T. Mosmann Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J. Immunol. Methods 65 1983 55 63
21. Y. Nakai, I. Sakakibara, K. Hirakura, S. Terabayashi, and S. Takeda A new acetylenic compound from the rhizomes of Atractylodes chinensis and its absolute configuration Chem. Pharm. Bull. 53 2005 1580 1581
22. B.M. Nie, X.Y. Jiang, J.X. Cai, S.L. Fu, L.M. Yang, L. Lin, Q. Hang, P.L. Lu, and Y. Lu Panaxydol and panaxynol protect cultured cortical neurons against Aβ25-35-induced toxicity Neuropharmacology 54 2008 845 853
23. B.M. Nie, L.M. Yang, S.L. Fu, X.Y. Jiang, P.H. Lu, and Y. Lu Protective effect of panaxydol and panaxynol on sodium nitroprusside-induced apoptosis in cortical neurons Chemico-Biol. Interact. 160 2006 225 231
24. T. Sakurai, H. Yamada, K.I. Saito, and Y. Kano On the evaluation of the preparation of Chinese medicinal prescriptions. III. Comparative studies on the acetylenes in Atractylodes Rizomes by 3D-HPLC Nat. Med. 48 1994 291 296
25. K.S. Sin, H.P. Kim, W.C. Lee, and P. Pachaly Pharmacological activities of the constituents of Atractylodes rhizomes Arch. Pharm. Res. 12 1989 236 238
26. C.J. Tsai, J.W. Liang, and H.R. Lin Sesquiterpenoids from Atractylodes macrocephala act as farnesoid X receptor and progesterone receptor modulators Bioorgan. Med. Chem. Lett. 22 2012 2326 2329
27. K.T. Wang, L.G. Chen, C.H. Wu, C.C. Chang, and C.C. Wang Gastroprotective activity of atractylenolide III from Atractylodes ovata on ethanol-induced gastric ulcer in vitro and in vivo J. Pharm. Pharmacol. 62 2010 381 388
28. J. Yamahara, T. Sawada, T. Tani, T. Nishino, and I. Kitagawa Pharmacological evaluation of the crude drug "zhu" Yakugaku Zasshi 97 1977 873 879
29. Z.H. Yan, R.L. Yang, Y. Jiang, Z.H. Yang, J.R. Yang, Q. Zhao, and Y. Lu Induction of apoptosis in human promyelocytic leukemia HL60 cells by panaxynol and panaxydol Molecules 16 2011 5561 5573
30. M.C. Yang, H.C. Kwon, Y.J. Kim, K.R. Lee, and H.O. Yang Oploxynes A and B, polyacetylenes from the stems of Oplopanax elatus J. Nat. Prod. 73 2010 801 805
31. X.J. Yao, Z.Q. Ding, Y.F. Xia, Z.F. Wei, Y.B. Luo, C. Feleder, and Y. Dai Inhibition of monosodium urate crystal-induced inflammation by scopoletin and underlying mechanisms Int. Immunopharmacol. 14 2012 454 462
32. Y. Ye, G.X. Chou, W. Hui, J.H. Chu, W.F. Fong, and Z.L. Yu Effects of sesquiterpenes isolated from largehead atractylodes rhizome on growth, migration, and differentiation of B16 melanoma cells Integr. Cancer Ther. 10 2011 92 100
33. L. Yin, Y.H. Yang, M.Y. Wang, X. Zhang, and J.A. Duan Effects of syringin from Phellodendron chinensis on monosodium urate crystal-induced inflammation and intercellular adhesion molecule-1 (ICAM-1) expression Afr. J. Pharm. Pharmacol. 6 2012 1515 1519
34. M.Y. Yoon, G.J. Chio, Y.H. Choi, K.S. Jang, B. Cha, and J.C. Kim Antifungal activity of polyacetylenes isolated from cirsium japonicum roots against various phytopathogenic fungi Ind. Crops Prod. 34 2011 882 887
35. J.J. Zhou, X.F. Yue, J.X. Han, and W.Y. Yang Improved MTT assay for activity of antitumor agents Chin. J. Pharm. 24 1993 455 457