Published April 30, 2021
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HRESIMS-guided isolation of aspidosperma-scandine type bisindole alkaloids from Melodinus cochinchinensis and their anti-inflammatory and cytotoxic activities
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- 1. * & Faculty of Agriculture and Food, Kunming University of Science and Technology, Kunming, 650500, China
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Li, Fang-Ru, Liu, Lu, Liu, Ya-Ping, Wang, Jin-Tang, Yang, Mei-Lian, Khan, Afsar, Qin, Xu-Jie, Wang, Yu-Dan, Cheng, Gui-Guang (2021): HRESIMS-guided isolation of aspidosperma-scandine type bisindole alkaloids from Melodinus cochinchinensis and their anti-inflammatory and cytotoxic activities. Phytochemistry (112673) 184: 1-7, DOI: 10.1016/j.phytochem.2021.112673, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112673
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- urn:lsid:plazi.org:pub:FFB9A567D038FF988427EC0E9D44FF8B
References
- Attar, U.R., Malik, S., Albert, K., 1986. Structural studies on vindolinine. Z. Naturforsch. B Chem. Sci.: Anorg. Chem., Org. Chem. 41, 386-392. https://doi.org/10.1515/znb- 1986-0316.
- Bruhn, T., Schaumloffel, A., Hemberger, Y., Bringmann, G., 2013. SpecDis: quantifying the comparison of calculated and experimental electronic circular dichroism spectra. Chirality 25, 243-249. https://doi.org/10.1002/chir.22138.
- Cai, X.H., Jiang, H., Li, Y., Cheng, G.G., Liu, Y.P., Feng, T., Luo, X.D., 2011. Cytotoxic indole alkaloids from Melodinus fusiformis and M. morsei. Chin. J. Nat. Med. 9, 259-263. https://doi.org/10.1016/S1875-5364(11)60061-7.
- Cai, X.H., Li, Y., Liu, Y.P., Li, X.N., Bao, M.F., Luo, X.D., 2012. Alkaloids from Melodinus yunnanensis. Phytochemistry 83, 116-124. https://doi.org/10.1016/j. phytochem.2012.06.013.
- Cheng, G.G., Zhao, Y.L., Zhang, Y., Lunga, P.K., Hu, D.B., Li, Y., Gu, J., Song, C.W., Sun, W.B., Liu, Y.P., Luo, X.D., 2014. Indole alkaloids from cultivated Vinca major. Tetrahedron 70, 8723-8729. https://doi.org/10.1016/j.tet.2014.09.026.
- Cheng, G.G., Li, D., Hou, B., Li, X.N., Liu, L., Chen, Y.Y., Lunga, P.K., Khan, A., Liu, Y.P., Zuo, Z.L., Luo, X.D., 2016. Melokhanines A-J, bioactive monoterpenoid indole alkaloids with diverse skeletons from Melodinus khasianus. J. Nat. Prod. 79, 2158-2166. https://doi.org/10.1021/acs.jnatprod.6b00011.
- Daudon, M., Mehri, M.H., Plat, M., Hagaman, E.W., Wenkert, E., 1976. Carbon-13 nuclear magnetic resonance spectroscopy of naturally occurring substances. 48. Dimeric quinolinic Melodinus alkaloids. J. Org. Chem. 41, 3275-3278. https://doi. org/10.1021/jo00905a017.
- Feng, T., Li, Y., Wang, Y.Y., Cai, X.H., Liu, Y.P., Luo, X.D., 2010. Cytotoxic indole alkaloids from Melodinus tenuicaudatus. J. Nat. Prod. 73, 1075-1079. https://doi. org/10.1021/np100086x.
- Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Keith, T., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, O., Foresman, J.B., Ortiz, J.V., Cioslowski, J., Fox, D.J., 2013. Gaussian 09, Revision E. 01. Gaussian, Inc., Wallingford CT.
- Fu, Y.H., Di, Y.T., He, H.P., Li, S.L., Zhang, Y., Hao, X.J., 2014. Angustifonines A and B, cytotoxic bisindole alkaloids from Bousigonia angustifolia. J. Nat. Prod. 77 https:// doi.org/10.1021/np4005823, 57-56.
- Giddings, L.-A., Liscombe, D.K., Hamilton, J.P., Childs, K.L., Della Penna, D., Buell, C.R., O' Connor, S.E., 2011. A Stereoselective hydroxylation step of alkaloid biosynthesis by a unique cytochrome P450 in Catharanthus roseus. J. Biol. Chem. 286, 16751-16757. https://doi.org/10.1074/jbc.M111.225383, 2011.
- Guo, L.W., Zhou, Y.L., 1993. Alkaloids from Melodinus hemsleyanus. Phytochemistry 34, 563-566. https://doi.org/10.1016/0031-9422(93)80046-U.
- Hunger, S.P., Mullighan, C.G., 2015. Acute lymphoblastic leukemia in children. N. Engl. J. Med. 373, 1541-1552. https://doi.org/10.1111/j.1755-3768.2012.4667.x.
- Iqbal, M., Marshall, E., Green, J.A., 2000. Ten-year survival in advanced malignant melanoma following treatment with interferon and vindesine. Ann. Oncol. 11, 483-485. https://doi.org/10.1023/A:1008341310927.
- Jabbour, E., O' Brien, S., Konopleva, M., Kantarjian, H., 2015. New insights into the pathophysiology and therapy of adult acute lymphoblastic leukemia. Cancer 121, 2517-2528. https://doi.org/10.1002/cncr.29383.
- Jiang, J.H., Zhang, W.D., Chen, Y.G., 2015. Phytochemical and pharmacological properties of the genus Melodinus - a review. Trop. J. Pharmaceut. Res. 14, 2325-2344. https://doi.org/10.4314/tjpr.v14i12.25.
- Jordan, M.A., Kamath, K., 2007. How do microtubule-targeted drugs work? An overview. Curr. Cancer Drug Targets 7, 730-742. https://doi.org/10.2174/ 156800907783220417.
- Kam, T.S., Lim, T.M., Subramaniam, G., Tee, Y.M., Yoganathan, K., 1999. 17-α- hydroxy- 14,15
- Li, F.R., Wang, Y.D., He, S.Y., Khan, A., Xue, Q.W., Cui, Q.M., Liu, L., Liu, Y.P., Cheng, G. G., 2020. Targeted isolation of terpenoid indole alkaloids from Melodinus cochinchinensis (Lour.) Merr. using molecular networking and their biological activities. Ind. Crop. Prod. 157, 112922. https://doi.org/10.1016/j. indcrop.2020.112922.
- Liu, Y.P., Li, Y., Cai, X.H., Li, X.Y., Kong, L.M., Cheng, G.G., Luo, X.D., 2012. Melodinines M-U, cytotoxic alkaloids from Melodinus suaveolens. J. Nat. Prod. 75, 220-224. https://doi.org/10.1021/np2009169.
- Liu, Y.P., Zhao, Y.L., Feng, T., Cheng, G.G., Zhang, B.H., Li, Y., Cai, X.H., Luo, X.D., 2013. Melosuavines A-H, cytotoxic bisindole alkaloid derivatives from Melodinus suaveolens. J. Nat. Prod. 76, 2322-2329. https://doi.org/10.1021/np4007469.
- Liu, Y.P., Yue, G. G. Lee, Lee, J.K.M., Feng, T., Zhao, Y.l., Li, Y., Lau, C.B.S., Luo, X.D., 2016. Melodinine V, an antitumor bisindole alkaloid with selective cytotoxicity from Melodinus henryi. Bioorg. Med. Chem. Lett 26, 4895-4898. https://doi.org/10.1016/ j.bmcl.2016.09.023.
- Lu, Y., Khoo, T.J., Wiart, C., 2014. The genus Melodinus (Apocynaceae): chemical and pharmacological perspectives. Pharmacol. Pharm. 5, 540-550. https://doi.org/ 10.4236/pp.2014.55064.
- O' Connor, S.E., Maresh, J.J., 2006. Chemistry and biology of monoterpene indole alkaloid biosynthesis. Nat. Prod. Res. 23, 532-547. https://doi.org/10.1002/ chin.200642260.
- Plat, M., Men, J.L., Janot, M.M., Wilson, J.M., Budzikiewicz, H., Durham, L.J., Nakagawa, Y., Djerassi, C., 1962. Mass spectrometry in structural and stereochemical problems. IX. Tabersonine alkaloids of Amsonia tabernaemontana. Tetrahedron Lett. 3, 271-276. https://doi.org/10.1016/S0040-4039(00)70865-3.
- Reed, L.J., Muench, H., 1938. A simple method of estimating fifty percent endpoints. Am. J. Epidemiol. 27, 493-497. https://doi.org/10.1093/oxfordjournals.aje.a118408.
- Saxton, J.E., 1997. Recent progress in the chemistry of the monoterpenoid indole alkaloids. Nat. Prod. Rep. 14, 559-590. https://doi.org/10.1039/np9971400559.
- Shao, S., Zhang, H., Yuan, C.M., Zhang, Y., Cao, M.M., Zhang, H.Y., Feng, Y., Ding, X., Zhou, Q., Zhao, Q., He, H.P., Hao, X.J., 2015. Cytotoxic indole alkaloids from the fruits of Melodinus cochinchinensis. Phytochemistry 116, 367-373. https://doi.org/ 10.1016/j.phytochem.2015.02.028.
- Sim, D.S., Navanesan, S., Sim, K.S., Gurusamy, S., Lim, S., Low, Y., Kam, T., 2019. Conolodinines A-D, Aspidosperma-aspidosperma bisindole alkaloids with antiproliferative activity from Tabernaemontana corymbosa. J. Nat. Prod. 82, 850-858. https://doi.org/10.1021/acs.jnatprod.8b00919.
- Tanaka, H., Matsushima, H., Nishibu, A., Clausen, B.E., Takashima, A., 2009. Dual therapeutic efficacy of vinblastine as a unique chemotherapeutic agent capable of inducing dendritic cell maturation. Can. Res. 69, 6987-6994. https://doi.org/ 10.1158/0008-5472.CAN-09-1106.
- Wang, L., He, H.P., Di, Y.T., Zhang, Y., Hao, X.J., 2012. Catharoseumine, a new monoterpenoid indole alkaloid possessing a peroxy bridge from Catharanthus roseus. Tetrahedron Lett. 53, 1576-1578. https://doi.org/10.1016/j.tetlet.2012.01.060.
- Wang, J.T., Liang, L.W., Li, F.R., Khan, A., Liu, L., Cao, J.X., Cheng, G.G., Zhao, T.R., 2019a. Chemical constituents of Melodinus hemsleyanus diels. Biochem. Systemat. Ecol. 84, 71-74. https://doi.org/10.1016/j.bse.2019.04.007.
- Wang, Z.Y., Jiang, M.J., Khan, A., Cai, S.B., Li, X.N., Liu, J.Q., Kai, G.Y., Zhao, T.R., Cheng, G.G., Cao, J.X., 2019b. Epigynumgenane-type pregnane glycosides from Epigynum cochinchinensis and their immunosuppressive activity. Phytochemistry 168, 112-127. https://doi.org/10.1016/j.phytochem.2019.112127.
- Xu, H.B., Ma, Y.B., Huang, X.Y., Geng, C.A., Wang, H., Zhao, Y., Yang, T.H., Chen, X.L., Yang, C.Y., Zhang, X.M., Chen, J.J., 2015. Bioactivity-guided isolation of antihepatitis B virus active sesquiterpenoids from the traditional Chinese medicine: rhizomes of Cyperus rotundus. J. Ethnopharmacol. 171, 131-140. https://doi.org/ 10.1016/j.jep.2015.05.040.
- Yang, M.L., Wang, Y.D., Patel, G., Xue, Q.W., Singor Njateng, G.S., Cai, S.B., Cheng, G.G., Kai, G.Y., 2020. In vitro and in vivo anti-inflammatory effects of different extracts from Epigynum auritum through down-regulation of NF-κB and MAPK signaling pathways. J. Ethnopharmacol. 113105. https://doi.org/10.1016/j.jep.2020.113105.
- Zhang, B.J., Liu, C., Bao, M.F., Zhong, X.H., Ni, L., Wu, J., Cai, X.H., 2017. Novel monoterpenoid indole alkaloids from Melodinus yunnanensis. Tetrahedron 73, 5821-5826. https://doi.org/10.1016/j.tet.2017.08.008.
- Zhang, Y., Ding, X., Shao, S., Guo, L.L., Zhao, Q., Hao, X.J., He, H.P., Melocochines, A. and B., 2019. Two alkaloids from the fruits of Melodinus cochinchinensis. Org. Lett. 21, 9272-9275. https://doi.org/10.1021/acs.orglett.9b03785.
- Zhao, Y., Geng, C.A., Ma, Y.B., Huang, X.Y., Chen, H., Cao, T.W., He, K., Wang, H., Zhang, X.M., Chen, J.J., 2014. UFLC/MS-IT-TOF guided isolation of anti-HBV active chlorogenic acid analogues from Artemisia capillaris as a traditional Chinese herb for the treatment of hepatitis. J. Ethnopharmacol. 156, 147-154. https://doi.org/ 10.1016/j.jep.2014.08.043.
- Zhao, Y.L., Cao, J., Shang, J.H., Liu, Y.P., Khan, A., Wang, H.S., Qian, Y., Liu, L., Ye, M., Luo, X.D., 2017. Airways antiallergic effect and pharmacokinetics of alkaloids from Alstonia Scholaris. Phytomedicine 27, 63-72. https://doi.org/10.1016/j. phymed.2017.02.002.
- Zhou, J., Feng, J.H., Fang, L., 2017. A novel monoterpenoid indole alkaloid with anticancer activity from Melodinus khasianus. Bioorg. Med. Chem. Lett 27, 893-896. https://doi.org/10.1016/j.bmcl.2017.01.005.