Published April 30, 2020
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Highly oxygenated and rearranged limonoids from the stem barks of Entandrophragma utile
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Hu, Ya-Lin, Tian, Xiao-Meng, Wang, Cheng-Cheng, Olga, Quasie, Yan, Dan, Tang, Peng-Fei, Zhang, Li-Na, Luo, Jun, Kong, Ling-Yi (2020): Highly oxygenated and rearranged limonoids from the stem barks of Entandrophragma utile. Phytochemistry (112282) 172: 1-10, DOI: 10.1016/j.phytochem.2020.112282, URL: http://dx.doi.org/10.1016/j.phytochem.2020.112282
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- urn:lsid:plazi.org:pub:CC76FFAAFFA6FF9AFF8EFFA1FFCBD56D
References
- Adejumo, O.E., Kolapo, I.O.A.A., Ayoola, M.D., 2011. Phytochemical and antisickling activities of Entandrophragma utile, chenopodium ambrosioides and petiveria alliacea. J. Med. Plants Res. 5, 1531-1535.
- An, F.L., Sun, D.M., Wang, R.Z., Yang, M.H., Luo, J., Kong, L.Y., 2018. Trijugin- and mexicanolide-type limonoids from the fruits of Heynea trijuga that reverse multidrug resistance in MCF-7/DOX cells. Phytochemistry 151, 42-49.
- Bracher, F., Eisenreich, W.J., Muhlbacher, J., Dreyer, M., Bringmann, G., 2004. Saludimerines A and B, novel-type dimeric alkaloids with stereogenic centers and configurationally semistable biaryl axes. J. Org. Chem. 69, 8602-8606.
- Champagne, D.E., Koul, O., Isman, M.B., Scudder, G.E., Towers, G.H.N., 1992. Biological activity of limonoids from the rutales. Phytochemistry 31, 377-394.
- Cui, J.X., Deng, Z.W., Li, J., Fu, H.Z., Proksh, P., Lin, W.H., 2005. Phragmalin-type limonoids from the mangrove plant Xylocarpus granatum. Phytochemistry 66, 2334-2339.
- Daniewski, W.M., Gumulka, M., Danikiewicz, W., Gluzinski, P., Krajewski, J., Pankowska, E., Szafranski, F., 1993. Utilin B, a tetranortriterpenoid of the mexicanolide group from bark of Entandrophragma utile. Phytochemistry 33, 1534-1536.
- Daniewski, W.M., Gumulka, M., Danikiewicz, W., Gluzinski, P., Krajewski, J., Sitkowski, J., Szafranski, F., 1994. A tetranortriterpenoid from the bark of Entandrophragma utile. Phytochemistry 36, 1001-1003.
- Daniewski, W.M., Gumulka, M., Danikiewicz, W., Sitkowski, J., Jacobsson, U., Norin, T., 1995. Entilin D, a heptanortriterpenoids from the bark of Entandrophragma utile. Phytochrmistry 40, 903-905.
- Hay, A.E., Ioset, J.R., Ahua, K.M., Diallo, D., Brun, R., Hostettmann, K., 2007. Limonoids orthoacetates and antiprotozoal compounds from the roots of Pseudocedrela kotschyi. J. Nat. Prod. 70, 9-13.
- John, T.A., Onabanjo, A.O., 1990a. Gastroprotective effects of an aqueous extract of Entandrophragma utile bark in experimental ethanol-induced peptic ulceration in mice and rats. J. Ethnopharmacol. 29, 87-93.
- John, T.A., Onabanjo, A.O., 1990b. Palazzo die Congressi. Italy, Florence.
- John, T.A., 1994. PhD Thesis University of Lagos, Lagos, Nigeria.
- John, T.A., Onabanjo, A.O., 2010. Effect of an aqueous extract of Entandrophragma utile bark on gastric acid secretion in rat and isolated ileum contractility in Guinea pig. Afr. J. Biomed. Res. 13, 197-206.
- Lin, B.D., Zhang, C.R., Yang, S.P., Wu, Y., Yue, J.M., 2011. Phragmalin-Type limonoid orthoesters from the twigs of Swietenia macrophylla. Chem. Pharm. Bull. 59, 458-465.
- Liu, H.B., Zhang, H., Li, P., Wu, Y., Gao, Z.B., Yue, J.M., 2012. Kv1.2 potassium channel inhibitors from Chukrasia tabularis. Org. Biomol. Chem. 10, 1448-1458.
- Luo, J., Tian, X.M., Zhang, H.J., Zhou, M.M., Li, J.H., Kong, L.Y., 2016. Two rare limonoids from the stem barks of Entandrophragma utile. Tetrahedron Lett. 57, 5334-5337.
- Mellor, H.R., Callaghan, R., 2008. Resistance to chemotherapy in cancer: a complex and integrated cellular response. Pharmacology 81, 275-300.
- Narender, T., Tanvir, K., Shweta, 2008. 13C NMR spectroscopy of D and B, D-ring secolimonoids of Meliaceae family. Nat. Prod. Res. 22, 763-800.
- Quasie, O., Li, H., Luo, J., Kong, L.Y., 2017. Two new phragmalin-type limonoids orthoesters from Entandrophragma candollei. Chin. J. Nat. Med. 15 0680-0683.
- Roy, A., Saraf, S., 2006. Limonoids: overview of significant bioactive triterpenes distributed in plants kingdom. Biol. Pharm. Bull. 29, 191-201.
- Steven, M.A., David, A.T., 1988. Limonoids from the seed of Entandrophragma caudatum. Phytochemistry 27, 1218-1220.
- Silva, M.N., Arruda, M.S.P., Castro, K.C.F., Silva, M.F.G.F., Fernandes, J.B., Vieira, P.C., 2008. Limonoids of the phragmalin type from Swietenia macrophylla and their chemotaxonomic significance. J. Nat. Prod. 71, 1983-1987.
- Tchouankeu, J.C., Tsamo, E., Sondengam, B.L., Connolly, J.D., Rycroft, D.S., 1990. Entilins A and B, two novel heptanortriterpenoid derivatives from Entandrophragma utile (meliaceae): structural elucidation using 2D NMR long-range δ C/δ H correlation experiments. Tetrahedron Lett. 31, 4505-4508.
- Tchouankeu, J.C., Nyasse, B., Tsamo, E., Sondengam, B.L., Morin, C., 1992. An ergostane derivative from the bark of Entandrophragma utile. Phytochemistry 31, 704-705.
- Tchouankeu, J.C., Nyasse, B., Tsamo, E., Connolly, J.D., 1996. 7α, 20(S)-Dihydroxy-4, 24(28)-ergostadien-3-one from Entandrophragma utile. J. Nat. Prod. 59, 958-959.
- Wang, X.N., Yin, S., Fan, C.Q., Wang, F.D., Lin, L.P., Ding, J., Yue, J.M., 2006. Turrapubesins A (I) and B (II), first examples of halogenated and maleimide-bearing limonoids in nature from Turraea pubescens. Org. Lett. 8, 3845-3848.
- Yin, S., Fan, C.Q., Wang, X.N., Lin, L.P., Ding, J., Yue, J.M., 2006. Xylogranatins A-D: novel tetranortriterpenoids with an unusual 9,10-seco scaffold from marine mangrove Xylocarpus grantum. Org. Lett. 8, 4935-4938.
- Zhang, F., Zhang, C.R., Tao, X., Wang, J., Chen, W.S., Yue, J.M., 2014. Phragmalin-type limonoids with NF-ҡB inhibition from Chukrasia tabularis var. velutina. Bioorg. Med. Chem. Lett 24, 3791-3796.
- Zhang, Q., Zheng, Q.H., Sang, Y.S., Sung, H.H.Y., Min, Z.D., 2018. New limonoids isolated from the bark of Melia toosendan. Chin. J. Nat. Med. 16 0946-0950.