Abstract
This study investigated the 70% aqueous acetone extract of the fruits of Schisandra rubriflora which led to the isolation of eight lignans, including a new isolate, rubrisandrin C (1), and seven known lignans (2–8). The structure of 1 was established by extensive 1D and 2D NMR spectroscopy and its absolute stereochemistry was determined by CD spectrum. Compounds 1–5 and 7–8 were evaluated for their anti-HIV-1 activity that showed inhibitory activity on HIV-1IIIB induced syncytium formation with EC50 values in the range of 2.26∼20.4 μg/mL. Compounds 1 and 7 exerted their obvious protection of HIV-1IIIB inducted MT-4 host cells lytic effects with a selectivity index of 15.4 and 24.6, respectively.
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Achenbach, H., Grob, J., Dominguez, X. A., Cano, G., Star, J. V., Del Carmen Brussolo, L., Muñoz, G., Salgado, F., and Lóez, L., Lignans neolignans and norneolignans from Krameria cystisoides. Phytochemistry, 26, 1159–1166 (1987).
Chen, D. F., Zhang, S. X., Wang, H. K., Zhang, S. Y., Sun, Q. Z., Cosentino, L. M., and Lee, K. H., Novel anti-HIV lancilactone C and related triterpenes from Kadsura lancilimba. J. Nat. Prod., 62, 94–97 (1999).
Chen, M., Kilgore, N., Lee, K. H., and Chen, D. F., Rubrisandrins A and B, lignans and related anti-HIV compounds from Schisandra rubriflora. J. Nat. Prod., 69, 1697–1701 (2006).
Chen, Y. G., Ping, W., Lin, Z. W., Sun, H. D., Qin, G. W., and Xie, Y. Y., Dibenzocyclooctadiene lignans from Kadsura angustifolia. Phytochemistry, 48, 1059–1062 (1998).
Chen, Y. G., Xie, Y. Y., Cheng, K. F., Cheung, K. K., and Qin, G. W., Compounds from Kadsura ananosma. Phytochemistry, 58, 1277–1280 (2001).
Choi, Y. W., Takamatsu, S., Khan, S. I., Srinivas, P. V., Ferreira, D., Zhao, J., and Khan, I. A., Schisandrene, a dibenzocyclooctadiene lignan from Schisandra chinensis: structure-antioxidant activity relationships of dibenzocyclooctadiene lignans. J. Nat. Prod., 69, 356–359 (2006).
Ikeya, Y., Sugama, K., Okada, M., and Mitsuhashi, H., Two lignans from Schisandra sphenanthera. Phytochemistry, 30, 975–980 (1991).
Ikeya, Y., Taguchi, H., and Yosioka, I., The Constituents of Schizandra chinensis BAILL. The structures of two new lignans, pre-gomisin and gomisin J. Chem. Pharm. Bull., 26, 682–684 (1978).
Ikeya, Y., Taguchi, H., Yosioka, I., and Kobayashi, H., The constituents of Schizandra chinensis Baill. VIII. the structures of two new lignans, tigloylgomisin P and angeloylgomisin P. Chem. Pharm. Bull., 28, 3357–3361 (1980).
Ikeya, Y., Taguchi, H., Yosioka, I., and Kobayashi, H., The constituents of Schizandra chinensis Baill. I. Isolation and structure determination of five new lignans, gomisin A, B, C, F and G, and the absolute structure of schizandrin. Chem. Pharm. Bull., 27, 1383–1394 (1979).
Kuo, Y. H., Kuo, L. M., and Chen, C. F., Four new C19 homolignans, schiarisanrins A, B, and D and cytotoxic schiarisanrin C, from Schizandra arisanensis. J. Org. Chem., 62, 3242–3245 (1997).
Li, G. P., Zhao, J. F., Tu, Y. Q., Yang, X. D., Zhang, H. B., and Li, L., Chemical constituents of Schisandra rubriflora Rehd. et Wils. J. Integr. Plant Biol., 47, 362–367 (2005).
Li, G., Zhao, J., Tu, Y., Yang, X., Zhang, H., and Li, L., Two new lignan glycosides from Schisandra rubriflora. Heterocycles, 63, 1437–1441 (2004a).
Li, H. M., Luo, Y. M., Pu, J. X., Li, X. N., Lei, C., Wang, R. R., Zheng, Y. T., Sun, H. D., and Li, R. T., Four new dibenzocyclooctadiene lignans from Schisandra rubriflora. Helv. Chim. Acta, 91, 1053–1062 (2008).
Li, L., Ren, H. Y., Yang, X. D., Zhao, J. F., Li, G. P., and Zhang, H. B., Rubriflorin A and B, two novel partially saturated dibenzocyclooctene lignans from Schisandra rubriflora. Helv. Chim. Acta, 87, 2943–2947 (2004b).
Liu, J. S., Tao, Y., and Huang, M. F., Studies on the constituents of schisandra henryi V: The structures of wulignan A1, A2, epiwulignan A1 and epischisandrone. Huaxue Xuebao, 46, 483–488 (1988).
Sun, H. D., Qiu, S. X., Lin, L. Z., Wang, Z. Y., Lin, Z. W., Pengsuparp, T., Pezzuto, J. M., Fong, H. H., Cordell, G. A., and Farnsworth, N. R., Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase. J. Nat. Prod., 59, 525–527 (1996).
Wang, H. J. and Chen, Y. Y., Studies of lignans from Schisandra rubriflora Rhed et Wils. Yao Xue Xue Bao, 20, 832–841 (1985).
Wang, J. H., Tam, S. C., Huang, H., Ouyang, D.Y., Wang, Y. Y., and Zheng, Y. T., Site-directed PEGylation of trichosanthin retained its anti-HIV activity with reduced potency in vitro. Biochem. Biophys. Res. Commun., 317, 965–971 (2004a).
Wang, Q., Ding, Z. H., Liu, J. K., and Zheng, Y. T., Xanthohumol, a novel anti-HIV-1 agent purified from Hops Humulus lupulus. Antiviral. Res., 64, 189–194 (2004b).
Xiao, W. L., Li, X. L., Wang, R. R., Yang, L. M., Li, L. M., Huang, S. X., Pu, J. X., Zheng, Y. T., Li, R. T., and Sun, H. D., Triterpenoids from Schisandra rubriflora. J. Nat. Prod., 70, 1056–1059 (2007a).
Xiao, W. L., Pu, J. X., Wang, R. R., Yang, L. M., Li, X. L., Li, S. H., Li, R. T., Huang, S. X., Zheng, Y. T., and Sun, H. D., Isolation and structure elucidation of nortriterpenoids from Schisandra rubriflor. Helv. Chim. Acta, 90, 1505–1513 (2007b).
Xiao, W. L., Yang, L. M., Gong, N. B., Wu, L., Wang, R. R., Pu, J. X., Li, X. L., Huang, S. X., Zheng, Y. T., Li, R. T., Lu, Y., Zheng, Q. T., and Sun, H. D., Rubriflordilactones A and B, two novel bisnortriterpenoids from Schisandra rubriflora and their biological activities. Org. Lett., 8, 991–994 (2006).
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Xiao, WL., Wang, RR., Zhao, W. et al. Anti-HIV-1 activity of lignans from the fruits of Schisandra rubriflora . Arch. Pharm. Res. 33, 697–701 (2010). https://doi.org/10.1007/s12272-010-0508-7
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DOI: https://doi.org/10.1007/s12272-010-0508-7