Abstract
A new cembranoid, discrepanolide A (1), along with four known cembranoids 2–5 were isolated from the Formosan soft coral Sinularia discrepans. The structures of these compounds were determined by analysis of spectroscopic data and by comparison of NMR data with those of known compounds. None of these compounds were found to be cytotoxic towards a limited panel of cancer cell lines. Compounds 3–5 were found to display significant in vitro anti-inflammatory activity in LPS-stimulated RAW264.7 macrophage cells by inhibiting the expression of the iNOS protein. Compound 5 also significantly inhibited the accumulation of pro-inflammatory COX-2 protein.
Similar content being viewed by others
References
Alley, M. C., Scudiero, D. A., Monks, A., Hursey, M. L., Czerwinski, M. J., Fine, D. L., Abbott, B. J., Mayo, J. G., Shoemaker, R. H., and Boyd, M. R., Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay. Cancer Res., 48, 589–601 (1988).
Ahmed, A. F., Tai, S. H., Wen, Z. H., Su, J. H., Wu, Y. C., Hu, W. P., and Sheu, J. H., A C-3 methylated isocembranoid and 10-oxocembranoids from a formosan soft coral, Sinularia grandilobata. J. Nat. Prod., 71, 946–951 (2008a).
Ahmed, A. F., Wen, Z. H., Su, J. H., Hsieh, Y. T., Wu, Y. C., Hu, W. P., and Sheu, J. H., Oxygenated cembranoids from a Formosan soft coral Sinularia gibberosa. J. Nat. Prod., 71, 179–185 (2008b).
Duh, C. Y. and Hou, R. S., Cytotoxic cembranoids from the Formosan soft corals Sinularia gibberosa and Sarcophyton trocheliophorum. J. Nat. Prod., 59, 595–598 (1996).
Duh, C. Y., Wang, S. K., Tseng, H. K., and Sheu, J. H., A novel cytotoxic biscembranoid from the Formosan soft coral Sinularia flexibilis. Tetrahedron Lett., 39, 7121–7122 (1998).
Duh, C. Y., Wang, S. K., Tseng, H. K., Sheu, J. H., and Chiang, M. Y., Novel cytotoxic cembranoids from the soft coral Sinularia flexibilis. J. Nat. Prod., 61, 844–847 (1998).
Hou, R. S., Duh, C. Y., Chiang, M. Y., and Lin, C. N., Sinugibberol, a new cytotoxic cembranoid diterpene from the soft coral Sinularia gibberosa. J. Nat. Prod., 58, 1126–1130 (1995).
Hsieh, P. W., Chang, F. R., McPhail, A. T., Lee, K. H., and Wu, Y. C., New cembranolide analogues from the formosan soft coral Sinularia flexibilis and their cytotoxicity. Nat. Prod. Res., 17, 409–418 (2003).
Lin, Y. S., Chen, C. H., Liaw, C. C., Chen, Y. C., Kuo, Y. H., and Shen, Y. C., Cembrane diterpenoids from the Taiwanese soft coral Sinularia flexibilis. Tetrahedron, 65, 9157–9164 (2009).
Lo, K. L., Khalil, A. T., Kuo, Y. H., and Shen, Y. C., Sinuladiterpenes A-F, new cembrane diterpenes from Sinularia flexibilis. Chem. Biodivers., 6, 2227–2235 (2009).
Lo, K. L., Khalil, A. T., Kuo, Chen, M. H., and Shen, Y. C., New cembrane diterpenes from Taiwanese soft coral Sinularia flexibilis. Helv. Chim. Acta, 93, 1329–1335 (2010).
Lu, Y., Huang, C. Y., Lin, Y. F., Wen, Z. H., Su, J. H., Kuo, Y. H., Chiang, M. Y., and Sheu, J. H., Anti-inflammatory cembranoids from the soft corals Sinularia querciformis and Sinularia granosa. J. Nat. Prod., 71, 1754–1759 (2008).
Lu, Y., Su, J. H., Huang, C. Y., Liu, Y. C., Kuo, Y. H., Wen, Z. H., Hsu, C. H., and Sheu, J. H., Cembranoids from the soft corals Sinularia granosa and Sinularia querciformis. Chem. Pharm. Bull., 58, 464–466 (2010).
Jean, Y. H., Chen, W. F., Duh, C. Y., Huang, S. Y., Hsu, C. H. Lin, C. S., Sung, C. S., Chen, I. M., and Wen, Z. H., Inducible nitric oxide synthase and cyclooxygenase-2 participate in anti-inflammatory and analgesic effects of the natural marine compound lemnalol from Formosan soft coral Lemnalia cervicorni. Eur. J. Pharmacol., 578, 323–331 (2008).
Jean, Y. H., Chen, W. F., Sung, C. S., Duh, C. Y., Huang, S. Y., Lin, C. S., Tai, M. H., Tzeng, S. F., and Wen, Z. H., Capnellene, a natural marine compound derived from soft coral, attenuates chronic constriction injury-induced neuropathic pain in rats. Br. J. Pharmacol., 158, 713–725 (2009).
Scudiero, D. A., Shoemaker, R. H., Paull, K. D., Monks, A., Tierney, S., Nofziger, T. H., Currens, M. J., Seniff, D., and Boyd, M. R., Evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines. Cancer Res., 48, 4827–4833 (1988).
Su, J. H., Ahmed, A. F., Sung, P. J., Chao, C. H., Kuo, Y. H., and Sheu, J. H., Manaarenolides A-I, diterpenoids from the soft coral Sinularia manaarensis. J. Nat. Prod., 69, 1134–1139 (2006).
Su, J. H., Lin, Y. F., Lu, Y., Yeh, H. C., Wang, W. H., Fan, T. Y., and Sheu, J. H., Oxygenated cembranoids from the cultured and wild-type soft corals Sinularia flexibilis. Chem. Pharm. Bull., 57, 1189–1192 (2009).
Su, J., Yang, R., Kuang, Y., and Zeng, L., A new cembranolide from the soft coral Sinularia capillosa. J. Nat. Prod., 63, 1543–1545 (2000).
Tixier-Durivault, A., Les octocoralliaires de Nha-Trang (Viet-Nam). Cahiers du Pacifique, 14, 115–236 (1970).
Wen, T., Ding, Y., Deng, Z., van Ofwegen, L., Proksch, P., and Lin, W., Sinulaflexiolides A-K, cembrane-type diterpenoids from the Chinese soft coral Sinularia flexibilis. J. Nat. Prod., 71, 1133–1140 (2008).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Lu, Y., Su, HJ., Chen, YH. et al. Anti-inflammatory cembranoids from the Formosan soft coral Sinularia discrepans . Arch. Pharm. Res. 34, 1263–1267 (2011). https://doi.org/10.1007/s12272-011-0804-x
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-011-0804-x