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Research Article

Cytotoxic tirucallanes from Dysoxylum alliaceum stem barks in human cancer and normal cells lines

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Pages 171-186 | Received 19 Jan 2024, Accepted 18 Apr 2024, Published online: 30 Apr 2024

References

  • Afzal, A., Oriqat, G., Akram Khan, M., Jose, J., Afzal, M. (2013). Chemistry and biochemistry of terpenoids from Curcuma and related species. J. Biol. Active Prod. Nature. 3(1):1-55.
  • Naini, A.A., Mayanti, T., Supratman, U. (2022). Triterpenoids from Dysoxylum genus and their biological activities. Arch. Pharm. Res. 45(2): 63-89. doi: 10.1007/s12272-022-01371-9
  • Lakshmi, V., Pandey, K., Agarwal, S.K. (2009). Bioactivity of the compounds in genus Dysoxylum. Acta Ecol. Sin. 29(1): 30-44. doi: 10.1016/j.chnaes.2009.04.005
  • Hu, J., Song, Y., Li, H., Yang, B., Mao, X., Zhao, Y., Shi, X. (2014). Cytotoxic and anti-inflammatory tirucallane triterpenoids from Dysoxylum binectariferum. Fitoterapia. 99: 86-91. doi: 10.1016/j.fitote.2014.09.010
  • Chen, J.L., Kernan, M.R., Jolad, S.D., Stoddart, C.A., Bogan, M., Cooper, R. (2007). Dysoxylins A-D, Tetranortriterpenoids with Potent Anti-RSV Activity from Dysoxylum gaudichaudianum. J. Nat. Prod. 70(2): 312-315. doi: 10.1021/np060398y
  • Riyadi, S.A., Naini, A.A., Supratman, U. (2023). Sesquiterpenoids from Meliaceae Family and Their Biological Activities. Molecules. 28(12): 4874. doi: 10.3390/molecules28124874
  • Naini, A.A., Mayanti, T., Maharani, R., Fajriah, S., Kabayama, K., Shimoyama, A., Manabe, Y., Fukase, K., Jungsuttiwong, S., Supratman, U. (2023). Dysoticans F–H: three unprecedented dimeric cadinanes from Dysoxylum parasiticum (Osbeck) Kosterm. stem bark. RSC. Adv. 13(14): 9370-9376. doi: 10.1039/D3RA01085F
  • Kautsari, A., Naini, A.A., Mayanti, T., Nurlelasari, Harneti, D., Farabi, K., Maharani, R., Harizon, Azmi, M.N., Supratman, U. (2024). Excelxylin A: a new seco A-ring tirucal-lane triterpenoid from the stem bark of Dysoxylum excelsum. J. Asian Nat. Prod. Res. 1-7. doi: 10.1080/10286020.2024.2329726
  • Naini, A.A., Mayanti, T., Maharani, R., Harneti, D., Nurlelasari., Farabi, K., Fajriah, S., Hilmayanti, E., Kabayama, K., Shimoyama, A., Manabe, Y., Fukase, K., Jungsuttiwong, S. (2024). Paraxylines A-G: Highly oxygenated preurianin-type limonoids with immunomodulatory TLR4 and cytotoxic activities from the stem bark of Dysoxylum parasiticum. Phytochemistry. 20: 114009. doi: 10.1016/j.phytochem.2024.114009
  • Jain, S.K., Meena, S., Qazi, A.K., Hussain, A., Bhola, S.K., Kshirsagar, R., Pari, K., Khajuria, A., Hamid, A., Shaanker, R.U., Bharate, S.B. (2013). Isolation and biological evaluation of chromone alkaloid dysoline, a new regioisomer of rohitukine from Dysoxylum binectariferum. Tetrahedron Lett. 54(52):7140-7143. doi: 10.1016/j.tetlet.2013.10.096
  • Suwardi, A.B., Navia, Z.I., Harmawan, T., Seprianto, S., Syamsuardi, S., Mukhtar, E. (2022). Diversity of wild edible fruit plant species and their threatened status in the Aceh Province, Indonesia. Biodiversitas. 23(3): 1310-1318.
  • Nishizawa, M., Inoue, A., Sastrapradja, S., Hayashi, Y. (1983). (+)-8-Hydroxycalamenene: A fish-poison principle of Dysoxylum acutan-gulum and D. Alliaceum. Phytochemistry. 22(9): 2083-2085. doi: 10.1016/0031-9422(83)80052-1
  • Nishizawa, M., Yamada, H., Sastrapradja, S., Hayashi, Y. (1985). Structure and synthesis of bicalamenene. Tetrahedron Lett. 26(12): 1535-1536. doi: 10.1016/S0040-4039(00)98545-9
  • Riyadi, S.A., Naini, A.A., Mayanti, T., Lesmana, R., Azmi, M.N., Fajriah, S., Jungsuttiwong, S., Supratman, U. (2024). Alliaxylines A–E: five new mexicanolides from the stem barks of Dysoxylum alliaceum (Blume) Blume ex A. Juss. J. Nat. Med. 1-10
  • Hu, J.M., Chen, H.Q., Dong, X., Wang, H., Dai, H.F., Gai, C.J., Wei, Y.M., Cheng, Z.A., Zhuo, Z.H., Liu, S.B., Mei, W.L. (2021). Three new tirucallane triterpenoids from the fruits of Chukrasia tabularis and their biological activities. Phytochem. Lett. 43: 70-74. doi: 10.1016/j.phytol.2021.03.013
  • Zhao, W.Y., Chen, J.J., Zou, C.X., Zhang, Y.Y., Yao, G.D., Wang, X.B., Huang, X.X., Lin, B., Song, S.J. (2019). New tirucallane triterpenoids from Picrasma quassioides with their potential antiproliferative activities on hepatoma cells. Bioorg. Chem. 84: 309-318. doi: 10.1016/j.bioorg.2018.11.049
  • Wang, S.Y., Huang, C., Sun, R.K., Lu, L.N., Liang, H.G., Gao, L., Huang, J., Wang, J.H. Yang, B.F. (2019). New tirucallane triterpenoids from the dried latex of Euphorbia resinifera. Phytochem. lett. 29: 220-224. doi: 10.1016/j.phytol.2018.12.012
  • Wang, J.R., Liu, H.L., Kurtán, T., Mándi, A., Antus, S., Li, J., Zhang, H.Y., Guo, Y.W. (2011). Protolimonoids and norlimonoids from the stem bark of Toona ciliata var. pubescens. Org. Biomol. Chem. 9(22): 7685-7696. doi: 10.1039/c1ob06150j
  • Gray, A.I., Bhandari, P., Waterman, P.G. (1988). New protolimonoids from the fruits of Phellodendron chinense. Phytochemistry. 27(6): 1805-1808. doi: 10.1016/0031-9422(88)80448-5
  • Yang, M.H., Wang, J.S., Luo, J.G., Wang, X.B., Kong, L.Y. (2012). Four new triterpenoids from Chisocheton paniculatus and their anti-inflammatory activities. Can. J. Chem. 90(2): 199-204. doi: 10.1139/v11-147
  • Xu, G.H., Kim, J.A., Kim, S.Y., Ryu, J.C., Kim, Y.S., Jung, S.H., Kim, M.K., Lee, S.H. (2008). Terpenoids and coumarins isolated from the fruits of Poncirus trifoliata. Chem. Pharm. Bull. 56(6): 839-842. doi: 10.1248/cpb.56.839
  • Jolad, S.D., Hoffmann, J.J., Cole, J.R., Tempesta, M.S., Bates, R.B. (1980). Constituents of Trichilia hispida (Meliaceae) A new triterpenoid, hispidone, and bourjotinolone A. J. Org. Chem. 45(15): 3132-3135. doi: 10.1021/jo01303a044
  • Happi, G.M., Kemayou, G.P., Stammler, H.G., Neumann, B., Ismail, M., Kouam, S.F., Wansi, J.D., Tchouankeu, J.C., Frese, M., Lenta, B.N., Sewald, N. (2021). Three phragmalin-type limonoids orthoesters and the structure of odoratone isolated from the bark of Entandrophragma candollei (Meliaceae). Phytochemistry. 181: 112537. doi: 10.1016/j.phytochem.2020.112537
  • Luo, X.D., Wu, S.H., Ma, Y.B., Wu, D.G. (2000). A new triterpenoid from Azadirachta indica. Fitoterapia. 71(6): 668-672. doi: 10.1016/S0367-326X(00)00230-6
  • Naini, A.A., Mayanti, T., Harneti, D., Maharani, R., Farabi, K., Herlina, T., Supratman, U., Fajriah, S., Kuncoro, H., Azmi, M.N., Shiono, Y., Jungsuttiwong, S. (2023). Sesquiterpenoids and sesquiterpenoid dimers from the stem bark of Dysoxylum parasiticum (osbeck) kosterm. Phytochemistry. 205: 113477. doi: 10.1016/j.phytochem.2022.113477
  • Sinaga, E.S., Mayanti, T., Naini, A.A., Harneti, D., Nurlelasari., Maharani, R., Farabi, K., Supratman, U., Fajriah, S., Azmi, M.N. (2022). Sesquiterpenoids from the stem bark of Lansium domesticum corr. cv. kokossan and their cytotoxic activity against MCF-7 breast cancer cell lines. Indones. J. Chem. 22(4): 1035-1042.
  • Zhang, Y., Wang, J., Wei, D., Wang, X., Luo, J., Luo, J., Kong, L. (2010). Cytotoxic tirucallane C26 triterpenoids from the stem barks of Aphanamixis grandifolia. Phytochemistry. 71(17-18): 2199-2204. doi: 10.1016/j.phytochem.2010.08.017
  • Chang, S.S., Huang, H.T., Lin, Y.C., Chao, C.H., Liao, G.Y., Lin, Z.H., Huang, H.C., Kuo, J.C.L., Liaw, C.C., Tai, C.J., Kuo, Y.H. (2022). Neritriterpenols AG, euphane and tirucallane triterpenes from Euphorbia neriifolia L. and their bioactivity. Phytochemistry. 199: 113199. doi: 10.1016/j.phytochem.2022.113199

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