Anti-inflammatory phenanthrene derivatives from stems of Dendrobium denneanum

Phytochemistry

Volumn 95, Issue , 2013, Pages 242-251

  Lin, Yuan ^a,b,c   Wang, Fei ^a   Yang, Li Juan ^a   Chun, Ze ^a   Bao, Jin Ku ^b   Zhang, Guo Lin ^a  

^a CHENGDU INSTITUTE OF BIOLOGY   (China)

^b SICHUAN UNIVERSITY   (China)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

ANTI INFLAMMATORY ACTIVITY; CYTOTOXIC; DENDROBIUM DENNEANUM; INOS; MAPKS; NFB; ORCHIDACEAE PHENANTHRENE; RAW264.7 CELL

Indexed keywords

DENDROBIUM; ORCHIDACEAE;

ANTIINFLAMMATORY AGENT; GLYCOSIDE; I KAPPA B; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INDUCIBLE NITRIC OXIDE SYNTHASE; LIPOPOLYSACCHARIDE; MITOGEN ACTIVATED PROTEIN KINASE P38; NF KAPPAB INHIBITOR ALPHA; NF-KAPPAB INHIBITOR ALPHA; NITRIC OXIDE; PHENANTHRENE DERIVATIVE; PLANT EXTRACT; STRESS ACTIVATED PROTEIN KINASE;

ANIMAL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; BIOSYNTHESIS; CHEMICALLY INDUCED DISORDER; CHEMISTRY; CYTOTOXIC; DENDROBIUM; DENDROBIUM DENNEANUM; DRUG EFFECT; HELA CELL LINE; HEPG2 CELL LINE; HUMAN; IC 50; INFLAMMATION; INOS; ISOLATION AND PURIFICATION; MACROPHAGE; MAPKS; METABOLISM; MOUSE; NF-ΚB; ORCHIDACEAE PHENANTHRENE; PHOSPHORYLATION; PHYTOTHERAPY; PLANT STEM; RAW264.7 CELL;

ANTI-INFLAMMATORY ACTIVITY; CYTOTOXIC; DENDROBIUM DENNEANUM; INOS; MAPKS; NF-ΚB; ORCHIDACEAE PHENANTHRENE; RAW264.7 CELL;

ANIMALS; ANTI-INFLAMMATORY AGENTS; DENDROBIUM; GLYCOSIDES; HELA CELLS; HEP G2 CELLS; HUMANS; I-KAPPA B PROTEINS; INFLAMMATION; INHIBITORY CONCENTRATION 50; JNK MITOGEN-ACTIVATED PROTEIN KINASES; LIPOPOLYSACCHARIDES; MACROPHAGES; MICE; NF-KAPPA B; NITRIC OXIDE; NITRIC OXIDE SYNTHASE TYPE II; P38 MITOGEN-ACTIVATED PROTEIN KINASES; PHENANTHRENES; PHOSPHORYLATION; PHYTOTHERAPY; PLANT EXTRACTS; PLANT STEMS;

EID: 84893795122     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2013.08.008     Document Type: Article

References (43)

1. Adriána, K., Andrea, V., Judit, H., 2008. Natural phenanthrenes and their biological activity. Phytochemistry 69, 1084-1110.
2. Antonov, A.S., Avilov, S.A., Kalinovsky, A., Anastyuk, S.D., Dmitrenok, P.S., Kalinin, V.I., Taboada, S., Bosh, A., Avila, C., Stonik, V., 2009. Triterpene glycosides from antarctic sea cucumbers. 2. Structure of achlioniceosides A1, A2 and A3 from the sea cucumber Achlionice wiolaecuspidata (=Rhipidothuria racowitzai). J. Nat. Prod. 72, 33-38.
3. Badger, A.M., Cook, M.N., Lark, M.W., Newman-Tarr, T.M., Swift, B.A., Nelson, A.H., Barone, F.C., Kumar, S., 1998. SB 203580 inhibits p38 mitogen-activated protein kinase, nitric oxide production, and inducible nitric oxide synthase in bovine cartilage-derived chondrocytes. J. Immunol. 161, 467-473. (Pubitemid 28285556)
4. Bennett, B.L., Sasaki, D.T., Murray, B.W., Sakata, S.T., Xu, W., Leisten, J.C., Motiwala, A., Pierce, S., Satoh, Y., Bhagwat, S.S., Manning, A.M., Anderson, D.W., 2001. SP600125, an anthrapyrazolone inhibitor of Jun N-terminal kinase. Proc. Natl. Acad. Sci. USA 98, 13681-13686. (Pubitemid 33115958)
5. Chen, C.C., Wang, J.K., Lin, S.B., 1998. Antisense oligonucleotides targeting protein kinase C-α, -βl, or -δ but not -η inhibit lipopolysaccharide-induced nitric oxide synthase expression in RAW 264.7 macrophages: involvement of a nuclear factor κB-dependent mechanism. J. Immunol. 161, 6206-6214.
6. Datla, P., Kalluri, M.D., Basha, K., Bellary, A., Kshirsagar, R., Kanekar, Y., Upadhyay, S., Singh, S., Rajagopal, V., 2010. 9,10-Dihydro-2,5- dimethoxyphenanthrene-1,7- diol, from Eulophia ochreata, inhibits inflammatory signalling mediated by Tolllike receptors. Br. J. Pharmacol. 160, 1158-1170.
7. Devkota, H.P., Watanabe, M., Watanabe, T., Yahara, S., 2012. Diplomorphanins A and B: new C-methyl flavonoids from Diplomorpha canescens. Chem. Pharm. Bull. 60, 554-556.
8. Fan, C., Wang, W., Wang, Y., Qin, G., Zhao, W., 2001. Chemical constituents from Dendrobium densiflorum. Phytochemistry 57, 1255-1258. (Pubitemid 32681505)
9. Guzik, T.J., Korbut, R., Adamek-Guzik, T., 2003. Nitric oxide and superoxide in inflammation and immune regulation. J. Physiol. Pharmacol. 54, 469-487. (Pubitemid 38029745)
10. Ito, M., Matsuzaki, K., Wang, J., Daikonya, A., Wang, N., Yao, X., Kitanaka, S., 2010. New phenanthrenes and stilbenes from Dendrobium loddigesii. Chem. Pharm. Bull. 58, 628-633.
11. Karin, M., 1995. The regulation of AP-1 activity by mitogen-activated protein kinases. J. Biol. Chem. 270, 16483-16486.
12. Khan, S., Shin, E.M., Choi, R.J., Jung, Y.H., Kim, J., Tosun, A., Kim, Y.S., 2011. Suppression of LPS-induced inflammatory and NF-κB responses by anomalin in RAW 264.7 macrophages. J. Cell. Biochem. 112, 2179-2188.
13. Khurelbat, D., Densmaa, D., Sanjjav, T., Gotov, C., Kitamura, C., Shibuya, H., Ohashi, K., 2010. Artemisioside, a new monoterpene glucoside from the aerial parts of Artemisia ordosica (Asteraceae). J. Nat. Med. 64, 203-205.
14. Klyne, W., 1950. The configuration of the anomeric carbon atomsinsome cardiac glycosides. Biochem. J. 47, Xii-XIii.
15. Korhonen, R., Lahti, A., Kankaanranta, H., Moilanen, E., 2005. Nitric oxide production and signaling in inflammation. Curr. Drug Targets 4, 471-479. (Pubitemid 41052412)
16. Lee, J.C., Laydon, J.T., McDonnell, P.C., Gallagher, T.F., Kumar, S., Green, D., McNulty, D., Blumenthal, M.J., Heys, R.J., Landvatter, S.W., Strickler, J.E., McLaughlin, M.M., Siemens, I.R., Fisher, S.M., Livi, G.P., White, J.R., Adams, J.L., Young, P.R., 1994. A protein kinase involved in the regulation of inflammatory cytokine biosynthesis. Nature 372, 739-746.
17. Lee, Y.H., Park, J.D., Baek, N.I., Kim, S.I., Ahn, B.Z., 1995. In vitro and in vivo antitumoral phenanthrenes from the aerial parts of Dendrobium nobile. Planta Med. 61, 178-180.
18. Lee, C.L., Chang, F.R., Yen, M.H., Yu, D., Liu, Y.N., Bastow, K.F., Susan, L., Morris, N., Wu, Y.C., Lee, K.H., 2009. Cytotoxic phenanthrenequinones and 9,10- dihydrophenanthrenes from Calanthe arisanensis. J. Nat. Prod. 72, 210-213.
19. Li, Y., Wang, C.L., Wang, Y.J., Guo, S.X., Yang, J.S., Chen, X.M., Xiao, P.G., 2009. Three new bibenzyl derivatives from Dendrobium candidum. Chem. Pharm. Bull. 57, 218-219.
20. Lin, T.H., Chang, S.J., Chen, C.C., Wang, J.P., Tsao, L.T., 2001. Two phenanthraquinones from Dendrobium moniliforme. J. Nat. Prod. 64, 1084-1086.
21. Liu, Y., Jiang, J.H., Zhang, Y., Chen, Y.G., 2009. Chemical constituents of Dendrobium aurantiacum var. denneanum. Chem. Nat. Compd. 45, 525-527.
22. Mendes, S.D.S., Candi, A., Vansteenbrugge, M., Pignon, M.R., Bult, H., Boudjeltia, K.Z., Munaut, C., Raes, M., 2009. Microarray analyses of the effects of NF-kappaB or PI3K pathway inhibitors on the LPS-induced gene expression profile in RAW264.7 cells: synergistic effects of rapamycin on LPS-induced MMP9-overexpression. Cell. Signalling 21, 1109-1122.
23. Okamura, N., Nohara, T., Yagi, A., Nishioka, I., 1981. Studies on the constituents of Zizyphi fructus. III. Structures of dammarane-type saponins. Chem. Pharm. Bull. 29, 676-683. (Pubitemid 11124652)
24. Ono, K., Han, J., 2000. The p38 signal transduction pathway activation and function. Cell. Signalling 12, 1-13. (Pubitemid 30017963)
25. Quivy, V., Lint, C.V., 2004. Regulation at multiple levels of NF-κB-mediated transactivation by protein acetylation. Biochem. Pharmacol. 68, 1221-1229. (Pubitemid 39094288)
26. Resnick, S.M., Gibson, D.T., 1996. Regio- and stereospecific oxidation of fluorene, dibenzofuran, and dibenzothiophene by naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816-4. Appl. Environ. Microbiol. 62, 4073-4080. (Pubitemid 26371508)
27. Shu, Y., Guo, S.X., Chen, X.M., Wang, C.L., Yang, J.S., 2004. On the chemical constituents of Dendrobium nobil. Chin. Pharm. J. 6, 421-422.
28. Sung, M.J., Davaatseren, M., Kim, W., Park, S.K., Kim, S., Hur, H.J., Kim, M.S., Kim, Y., Kwon, D.Y., 2009. Vitisin A suppresses LPS-induced NO production by inhibiting ERK, p38, and NF-kappaB activation in RAW 264.7 cells. Int. Immunopharmacol. 9, 319-323.
29. Takayanagi, T., Ishikawa, T., Kitajima, J., 2003. Sesquiterpene lactone glucosides and alkyl glycosides from the fruit of cumin. Phytochemistry 63, 479-484. (Pubitemid 36648111)
30. Thirunavukkarasu, C., Watkins, S.C., Gandhi, C.R., 2006. Mechanisms of endotoxin induced NO, IL-6, and TNF-a production in activated rat hepatic stellate cells: role of p38 MAPK. Hepatology 44, 389-398. (Pubitemid 44214878)
31. Wang, H.K., Zhao, T.F., 1985. Dendrobine and 3-hydroxy-2-oxodendrobine from Dendrobium nobile. J. Nat. Prod. 48, 796-801.
32. Wang, X.Y., Ke, C.Q., Tang, C.P., Yuan, D., Ye, Y., 2009. 9,10-Dihydrophenanthrenes and -henanthrenes from Juncus setchuensis. J. Nat. Prod. 72, 1209-1212.
33. Yang, L., Qin, L.H., Annie Bligh, S.W., Bashall, A., Zhang, C.F., Zhang, M., Wang, Z.T., Xu, L.S., 2006a. A new phenanthrene with a spirolactone from Dendrobium chrysanthum and its anti-inflammatory activities. Bioorg. Med. Chem. 14, 3496-3510.
34. Yang, L., Wang, Z., Xu, L., 2006b. Phenols and a triterpene from Dendrobium aurantiacum var. denneanum (Orchidaceae). Biochem. Syst. Ecol. 34, 658-660. (Pubitemid 44202237)
35. Yang, H., Sung, S.H., Kim, Y.C., 2007a. Antifibrotic phenanthrenes of Dendrobium nobile stems. J. Nat. Prod. 70, 1925-1929.
36. Yang, L., Wang, Y., Zhang, G., Zhang, F., Zhang, Z., Wang, Z., Xu, L., 2007b. Simultaneous quantitative and qualitative analysis of bioactive phenols in Dendrobium aurantiacum var. denneanum by high-performance liquid chromatography coupled with mass spectrometry and diode array detection. Biomed. Chromatogr. 21, 687-694. (Pubitemid 47073118)
37. Yang, L.J., Chen, Q.F., Wang, F., Zhang, G.L., 2011. Antiosteoporotic compounds from seeds of Cuscuta chinensis. J. Ethnopharmacol. 135, 553-560.
38. Yoshikawa, K., Ito, T., Iseki, K., Baba, C., Imagawa, H., Yagi, Y., Morita, H., Asakawa, Y., Kawano, S., Hashimoto, T., 2012. Phenanthrene derivatives from Cymbidium great flower marie laurencin and their biological activities. J. Nat. Prod. 75, 605-609.
39. Zhang, G.N., Bi, Z.M., Wang, Z.T., Xu, L.S., Xu, G.J., 2003. Advances in studies on chemical constitutents from plants of Dendrobium Sw. Chin. Tradit. Herbal Drugs 34, S5-S8.
40. Zhang, G.N., Zhong, L.Y., Bligh, S.W.A., Guo, Y.L., Zhang, C.F., Zhang, M., Wang, Z.T., Xu, L.S., 2005. Bi-bicyclic and bi-tricyclic compounds from Dendrobium thyrsiflorum. Phytochemistry 66, 1113-1120. (Pubitemid 40728304)
41. Zhang, X., Xu, J.K., Wang, J., Wang, N.L., Hiroshi, K., Sumumu, K., Yao, X.S., 2007. Bioactive bibenzyl derivatives and fluorenones from Dendrobium nobile. J. Nat. Prod. 70, 24-28.
42. Zhang, X., Tu, F.J., Yu, H.Y., Wang, N.L., Wang, Z., Yao, X.S., 2008. Copacamphane, picrotoxane and cyclocopacamphane sesquiterpenes from Dendrobium nobile. Chem. Pharm. Bull. 56, 854-857. (Pubitemid 351872258)
43. Zhao, W., Ye, Q., Tan, X., Jiang, H., Li, X., Chen, K., Kinghorn, A.D., 2001. Three new sesquiterpene glycosides from Dendrobium nobile with immunomodulatory activity. J. Nat. Prod. 64, 1196-1200. (Pubitemid 32937891)