Review: Indole Alkaloids and Antimalarial Activity in the Tabernaemontana Species
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Background: Malaria, caused by Plasmodium parasites, is a highly prevalent and lethal illness that shows persistent ability to develop resistance. Antiplasmodial compounds that are indole-based prevent hemozoin formation, exhibiting efficacy against chloroquine-resistant Plasmodium strains. Tabernaemontana is a member of the genus comprised to the Apocynaceae family and has long been known for its efficacy in traditional and herbal tribal medicine. Apocynaceae can be recognized by the existence of indole alkaloids, and Tabernaemontana spp. is widely identifiable for its ability to synthetize a wide variety of indole alkaloids. Objective: This literature review seeks to provide a comprehensive summary of indole alkaloid compounds from Tabernaemontana spp. and the effectiveness of Tabernaemontana spp. as antimalarials. Methods: Preferred Reporting Items for Systematic Reviews and Meta-Analyses (PRISMA) protocols were followed to explore the PubMed, Sage Journal, ScienceDirect, and Wiley Library databases. Results: 23 publications on the antimalarial activity and indole alkaloids of several species of the genus Tabernaemontana were discovered. Conclusion: Various species of Tabernaemontana contain indole alkaloids, and extracts of the plant or parts of the plant and isolates have weak to strong antimalarial activity.
Amelia, P., Eko, A., Yusuke, N., Toshio, H., Takahiro, K., & Toshihiro, T. (2021). Two new bisindole alkaloids from Tabernaemontana macrocarpa Jack. Journal of Natural Medicines, 0123456789. https://doi.org/10.1007/s11418-021-01510-4
Amelia, P., Nugroho, A. E., Hirasawa, Y., Kaneda, T., Tougan, T., Horii, T., & Morita, H. (2019). Two new sarpagine-type indole alkaloids and antimalarial activity of 16-demethoxycarbonylvoacamine from Tabernaemontana macrocarpa Jack. Journal of Natural Medicines, 73(4), 820–825. https://doi.org/10.1007/s11418-019-01317-4
Appiah-Opong, R., Agyemang, K., Dotse, E., Atchoglo, P., Owusu, K. B. A., Aning, A., Sakyiamah, M., Adegle, R., Ayertey, F., Appiah, A. A., & Nyarko, A. K. (2022). Anti-plasmodial, Cytotoxic and Antioxidant Activities of Selected Ghanaian Medicinal Plants. Journal of Evidence-Based Integrative Medicine, 27, 1–8. https://doi.org/10.1177/2515690X211073709
Athipornchai, A. (2018). A review on tabernaemontana spp.: Multipotential medicinal plant. Asian Journal of Pharmaceutical and Clinical Research, 11(5), 45–53. https://doi.org/10.22159/ajpcr.2018.v11i5.11478
Bagnaresi, P., Markus, R. P., Hotta, C. T., Pozzan, T., & S. Garcia, C. R. (2008). Desynchronizing Plasmodium Cell Cycle Increases Chloroquine Protection at Suboptimal Doses. The Open Parasitology Journal, 2(1), 55–58. doi: 10.2174/1874421400802010055
Bapela, M. J., Heyman, H., Senejoux, F., & Meyer, J. . M. (2018). 1H NMR-based metabolomics of antimalarial plant species traditionally used by Vha-Venda people in Limpopo Province, South Africa and isolation of antiplasmodial compounds. Journal of Ethnopharmacology. doi: 10.1016/j.jep.2018.07.022
Bitombo, A. N., Zintchem, A. A. A., Atchadé, A. D. T., Mbabi Nyemeck, N., Bikobo, D. S. N., Pegnyemb, D. E., & Bochet, C. G. (2021). Antiplasmodial activities of indole alkaloids from Tabernaemontana penduliflora K. Schum (Apocynaceae). Fitoterapia, 153(April), 1–9. https://doi.org/10.1016/j.fitote.2021.104941
Cai, Y. S., Sarotti, A. M., Zhou, T. L., Huang, R., Qiu, G., Tian, C., Miao, Z. H., Mándi, A., Kurtán, T., Cao, S., & Yang, S. P. (2018). Flabellipparicine, a Flabelliformide-Apparicine-Type Bisindole Alkaloid from Tabernaemontana divaricata. Journal of Natural Products, 81(9), 1976–1983. https://doi.org/10.1021/acs.jnatprod.8b00191
Duru, C. M., & Mbata, T. I. (2010). The Antimicrobial Activities and Phytochemical Screening of Ethanolic Leaf Extracts of Hedranthera barteri Hook and Tabernaemontana pachysiphon Stapf . Journal of Developmental Biology and Tissue Engineering, 2(June), 1–4.
Ekawati, A. R., Supriningrum, R., Handayani, F., Tinggi, S., Kesehatan, I., Brig, J., Abdul, J., Sjahranie, W., & Air, N. (2023). KARAKTERISASI EKSTRAK ETANOL DAUN SELUTUI PUKA. Jurnal Ilmu Farmasi Dan Farmasi Klinik, 20(1), 43–52.
Federici, E., Palazzino, G., Nicoletti, M., & Galeffi, C. (2000). Antiplasmodial activity of the alkaloids of Peschiera fuchsiaefolia. Planta Medica, 66(1), 93–95. https://doi.org/10.1055/s-0029-1243122
Forkuo, A. D., Ansah, C., Mensah, K. B., Annan, K., Gyan, B., Theron, A., Mancama, D., & Wright, C. W. (2017). In vitro anti-malarial interaction and gametocytocidal activity of cryptolepine. Malaria Journal, 16(1), 1–9. https://doi.org/10.1186/s12936-017-2142-z
Foudjo Melacheu, G. L., Mfotie Njoya, E., Jouda, J. B., Wakeu Kweka, B. N., Djama Mbazoa, C., Wang, F., & Wandji, J. (2019). Two new indole alkaloids from Tabernaemontana contorta Stapf. Phytochemistry Letters, 30(September 2018), 116–119. doi: 10.1016/j.phytol.2019.01.028
Gopalan, R. C., Emerce, E., Wright, C. W., Karahalil, B., Karakaya, A. E., & Anderson, D. (2011). Effects of the anti-malarial compound cryptolepine and its analogues in human lymphocytes and sperm in the Comet assay. Toxicology Letters, 207(3), 322–325. https://doi.org/10.1016/j.toxlet.2011.09.010
Health Organization, W. (2023). World malaria report 2023 -- spread view. https://www.who.int/about/licensing.
Hirasawa, Y., Yasuda, R., Minami, W., Hirata, M., Nugroho, A. E., Tougan, T., Uchiyama, N., Hakamatsuka, T., Horii, T., & Morita, H. (2021). Divaricamine A, a new anti-malarial trimeric monoterpenoid indole alkaloid from Tabernaemontana divaricata. Tetrahedron Letters, 83, 153423. https://doi.org/10.1016/j.tetlet.2021.153423
Ingkaninan, K., Changwijit, K., & Suwanborirux, K. (2006). Vobasinyl-iboga bisindole alkaloids, potent acetylcholinesterase inhibitors from Tabernaemontana divaricata root. Journal of Pharmacy and Pharmacology, 58(6), 847–852. https://doi.org/10.1211/jpp.58.6.0015
Kam, T. S., & Sim, K. M. (2002). Five new iboga alkaloids from Tabernaemontana corymbosa. Journal of Natural Products, 65(5), 669–672. https://doi.org/10.1021/np0105432
Kemenkes. (2022). Laporan Tahunan 2022 Malaria. Kemenkes RI, 1–51. https://www.bca.co.id/-/media/Feature/Report/File/S8/Laporan-Tahunan/20230216-bca-ar-2022-indonesia.pdf
Kgokong, J. L., Smith, P. P., & Matsabisa, G. M. (2005). 1,2,4-Triazino-[5,6b]indole derivatives: Effects of the trifluoromethyl group on in vitro antimalarial activity. Bioorganic and Medicinal Chemistry, 13(8), 2935–2942. https://doi.org/10.1016/j.bmc.2005.02.017
Lim, K. H., Raja, V. J., Bradshaw, T. D., Lim, S. H., Low, Y. Y., & Kam, T. S. (2015). Ibogan, tacaman, and cytotoxic bisindole alkaloids from Tabernaemontana. Cononusine, an iboga alkaloid with unusual incorporation of a pyrrolidone moiety. Journal of Natural Products, 78(5), 1129–1138. https://doi.org/10.1021/acs.jnatprod.5b00117
Marinho, F. F., Simões, A. O., Barcellos, T., & Moura, S. (2016). Brazilian Tabernaemontana genus: Indole alkaloids and phytochemical activities. Fitoterapia, 114, 127–137. https://doi.org/10.1016/j.fitote.2016.09.002
Masuda, K., Akiyama, T., Taki, M., Takaishi, S., Iijima, Y., Yamazaki, M., Aimi, N., Jato, J., & Waterman, P. G. (2000). Isolation of 10-hydroxycoronaridine from Tabernaemontana penduliflora and its estrogen-like activity. Planta Medica, 66(2), 169–171. https://doi.org/10.1055/s-2000-11132
Milner, D. A. (2018). Malaria pathogenesis. Cold Spring Harbor Perspectives in Medicine, 8(1), 1–11. https://doi.org/10.1101/cshperspect.a025569
Naidoo, C. M., Naidoo, Y., Dewir, Y. H., Murthy, H. N., El-hendawy, S., & Al-suhaibani, N. (2021). Major Bioactive Alkaloids and Biological Activities of Tabernaemontana Species (Apocynaceae). 1–27.
Nge, C. E., Chong, K. W., Thomas, N. F., Lim, S. H., Low, Y. Y., & Kam, T. S. (2016). Ibogan, Aspidosperman, Vincamine, and Bisindole Alkaloids from a Malayan Tabernaemontana corymbosa: Iboga Alkaloids with C-20α Substitution. Journal of Natural Products, 79(5), 1388–1399. https://doi.org/10.1021/acs.jnatprod.6b00129
Noguchi, Y., Hirose, T., Ishiyama, A., Iwatsuki, M., Otoguro, K., Sunazuka, T., & Ōmura, S. (2016). Synthesis and stereochemical determination of an antiparasitic pseudo-aminal type monoterpene indole alkaloid. Journal of Natural Medicines, 70(3), 302–317. https://doi.org/10.1007/s11418-016-1012-2
Omar, F., Tareq, A. M., Alqahtani, A. M., Dhama, K., Sayeed, M. A., Emran, T. Bin, & Simal-Gandara, J. (2021). Plant-based indole alkaloids: A comprehensive overview from a pharmacological perspective. Molecules, 26(8). https://doi.org/10.3390/molecules26082297
Passemar, C., Saléry, M., Soh, P. N., Linas, M. D., Ahond, A., Poupat, C., & Benoit-Vical, F. (2011). Indole and aminoimidazole moieties appear as key structural units in antiplasmodial molecules. Phytomedicine, 18(13), 1118–1125. https://doi.org/10.1016/j.phymed.2011.03.010
Pereira, P. S., França, S. D. C., De Oliveira, P. V. A., Breves, C. M. D. S., Pereira, S. I. V., Sampaio, S. V., Nomizo, A., & Dias, D. A. (2008). Chemical constituents from Tabernaemontana catharinensis root bark: A brief NMR review of indole alkaloids and in vitro cytotoxicity. Quimica Nova, 31(1), 20–24. https://doi.org/10.1590/S0100-40422008000100004
Perera, P., Sandberg, F., Van Beek, T. A., & Verpoorte, R. (1984). Tertiary indole alkaloids from fruits of Tabernaemontana dichotoma. Planta Medica, 50(3), 251–253. https://doi.org/10.1055/s-2007-969691
Qu, Y., Simonescu, R., & De Luca, V. (2016). Monoterpene Indole Alkaloids from the Fruit of Tabernaemontana litoralis and Differential Alkaloid Composition in Various Fruit Components. Journal of Natural Products, 79(12), 3143–3147. https://doi.org/10.1021/acs.jnatprod.6b00405
Ramalhete, C., Lopes, D., Mulhovo, S., Rosario, E. V., & Jose, F. U. M. (2008). Antimalarial Activity of Some Plants Traditionally Used in Mozambique. 1–9.
Silveira, D., de Melo, A. M. M. F., Magalhães, P. O., & Fonseca-Bazzo, Y. M. (2017). Tabernaemontana Species: Promising Sources of New Useful Drugs. In Studies in Natural Products Chemistry (Vol. 54, Issue 1984). doi: 10.1016/B978-0-444-63929-5.00007-3
Sim, D. S. Y., Chong, K. W., Nge, C. E., Low, Y. Y., Sim, K. S., & Kam, T. S. (2014). Cytotoxic vobasine, tacaman, and corynanthe-tryptamine bisindole alkaloids from Tabernaemontana and structure revision of tronoharine. Journal of Natural Products, 77(11), 2504–2512. https://doi.org/10.1021/np500589u
Simões, A. O. andr. O., Endress, M. E., & Conti, E. (2010). Systematics and character evolution of Tabernaemontaneae (Apocynaceae, Rauvolfioideae) based on molecular and morphological evidence. Taxon, 59(3), 772–790. doi: 10.1002/tax.593009
Spillman, N. J., & Kirk, K. (2015). The malaria parasite cation ATPase PfATP4 and its role in the mechanism of action of a new arsenal of antimalarial drugs. International Journal for Parasitology: Drugs and Drug Resistance, 5(3), 149–162. doi: 10.1016/j.ijpddr.2015.07.001
Surur, A. S., Huluka, S. A., Mitku, M. L., & Asres, K. (2020). Indole: The after next scaffold of antiplasmodial agents? Drug Design, Development and Therapy, 14, 4855–4867. doi: 10.2147/DDDT.S278588
Titanji, V. P. ., Zofou, D., & Ngemenya, M. N. (2008). Review Paper THE ANTIMALARIAL POTENTIAL OF MEDICINAL PLANTS USED FOR THE TREATMENT. African Journal of Tradtional Complementary and Alternative Medicine, 5, 302–321.
Van Beek, T. ., Verpoorte, R., Svendsen, A. B., Leeuwenberg, A. J. ., & Bisset, N. . (1984). Tabernaemontana L.: a Reviem of Its Taxonomy, Phytochemistry, Ethnobotany and Pharcology. Journal of Ethnopharmacology, 10, 113–138.
World Health Organization. (2023). World malaria report 2022 (double page version). In American Journal of Tropical Medicine and Hygiene (Vol. 9, Issue 1). https://www.wipo.int/amc/en/%0Awww.thelancet.com
Xu, J., Qu, W., Cao, W. Y., Wang, Y., Zheng, K. J., Luo, S. Z., Wu, M. Y., Liu, W. Y., Feng, F., & Zhang, J. (2019). Chemical Constituents from Tabernaemontana bufalina Lour. Chemistry and Biodiversity, 16(1), 12–17. doi: 10.1002/cbdv.201800491
Yu, Y., Bao, M. F., Wu, J., Chen, J., Yang, Y. R., Schinnerl, J., & Cai, X. H. (2019). Tabernabovines A-C: Three Monoterpenoid Indole Alkaloids from the Leaves of Tabernaemontana bovina. Organic Letters, 21(15), 5938–5942. doi: 10.1021/acs.orglett.9b02060
Yuwen, H., Yuan, Y., Hao, X., He, H., & Zhang, Y. (2019). Two new monoterpenoid indole alkaloids from Tabernaemontana divaricata. Natural Product Research, 33(15), 2139–2144. doi: 10.1080/14786419.2018.1488707
Zaima, K., Koga, I., Iwasawa, N., Hosoya, T., Hirasawa, Y., Kaneda, T., Ismail, I. S., Lajis, N. H., & Morita, H. (2013). Vasorelaxant activity of indole alkaloids from Tabernaemontana dichotoma. Journal of Natural Medicines, 67(1), 9–16. doi: 10.1007/s11418-012-0638-y
Zhang, B. J., Teng, X. F., Bao, M. F., Zhong, X. H., Ni, L., & Cai, X. H. (2015). Cytotoxic indole alkaloids from Tabernaemontana officinalis. Phytochemistry, 120, 46–52. doi: 10.1016/j.phytochem.2014.12.025
Zhang, H., Wang, X. N., Lin, L. P., Ding, J., & Yue, J. M. (2007). Indole alkaloids from three species of the Ervatamia Genus: E. officinalis, E. divaricata, and E. divaricata Gouyahua. Journal of Natural Products, 70(1), 54–59. doi: 10.1021/np060344o
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