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Natural Product Research
Formerly Natural Product Letters
Volume 38, 2024 - Issue 12
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Swietenolide isolated from Swietenia macrophylla King in Hook seeds shows in vitro anti-colorectal cancer activity through inhibition of mouse double minute 2 (MDM2) homolog

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Pages 2097-2104 | Received 10 Sep 2022, Accepted 30 Jun 2023, Published online: 14 Jul 2023

References

  • Arumugasamy K, Latha K, Kumar N. 2004. Studies on some pharmacognostic profiles of Swietenia macrophylla king. Anc Sci Life. 24(2):97–102.
  • Bourdy G, DeWalt SJ, Chávez De Michel LR, Roca A, Deharo E, Muñoz V, Balderrama L, Quenevo C, Gimenez A. 2000. Medicinal plants uses of the Tacana, an Amazonian Bolivian ethnic group. J Ethnopharmacol. 70(2):87–109. doi: 10.1016/S0378-8741(99)00158-0.
  • Chakrabartty T, Connolly JD, McCrindle R, Overton KH, Schwarz JCP. 1968. Tetranortriterpenoids-VI. [Bicyclononanolides IV] swietenolide – the functional groups. Tetrahedron. 24(3):1503–1506. doi: 10.1016/0040-4020(68)88103-7.
  • Chen LC, Liao HR, Chen PY, Kuo WL, Chang TH, Sung PJ, Wen ZH, Chen JJ. 2015. Limonoids from the seeds of Swietenia macrophylla and their anti-inflammatory activities. Molecules. 20(10):18551–18564. doi: 10.3390/molecules201018551.
  • Connolly JD, McCrindle R, Overton KH, Warnock WDC. 1965. Swietenolide. Tetrahedron Lett. 6(33):2937–2940. doi: 10.1016/S0040-4039(00)90240-5.
  • Dewanjee S, Maiti A, Das AK, Mandal SC, Dey SP. 2009. Swietenine: a potential oral hypoglycemic from Swietenia macrophylla seed. Fitoterapia. 80(4):249–251. doi: 10.1016/j.fitote.2009.02.004.
  • Falah S, Suzuki T, Katayama T. 2008. Chemical constituents from Swietenia macrophylla bark and their antioxidant activity. Pak J Biol Sci. 11(16):2007–2012. doi: 10.3923/pjbs.2008.2007.2012.
  • Goh BH, Chan CK, Kamarudin MNA, Abdul Kadir H. 2014. Swietenia macrophylla King induces mitochondrial-mediated apoptosis through p53 upregulation in HCT116 colorectal carcinoma cells. J Ethnopharmacol. 153(2):375–385. doi: 10.1016/j.jep.2014.02.036.
  • Goh BH, Kadir HA. 2011. In vitro cytotoxic potential of Swietenia macrophylla King seeds against human carcinoma cell lines. J Med Plants Res. 5(8):1395–1404.
  • Govindachari TR, Suresh G, Banumathy B, Masilamani S, Gopalakrishnan G, Krishna Kumari GN. 1999. Antifungal activity of some B,D-seco limonoids from two meliaceous plants. J Chem Ecol. 25(4):923–933. doi: 10.1023/A:1020809204288.
  • Graham JG, Quinn ML, Fabricant DS, Farnsworth NR. 2000. Plants used against cancer – an extension of the work of Jonathan Hartwell. J Ethnopharmacol. 73(3):347–377. doi: 10.1016/S0378-8741(00)00341-X.
  • Guha Sircar SS, Chakravarty T. 1951. The chemical investigation of the seeds of Swietenia macrophylla. Part I. The non-bitter principle. J Indian Chem Soc. 25(4):207–210. doi: 10.5281/ZENODO.6565555.
  • Kadota S, Marpaung L, Kikuchi T, Ekimoto H. 1990. Constituents of the seeds of Swietenia mahagoni Jacq: II: structures of Swietemahonin A, B, C, D, E, F, and G and Swieternahonolide. Chem Pharm Bull. 38(4):894–901. doi: 10.1248/cpb.38.894.
  • Kipassa NT, Iwagawa T, Okamura H, Doe M, Morimoto Y, Nakatani M. 2008. Limonoids from the stem bark of Cedrela odorata. Phytochemistry. 69(8):1782–1787. doi: 10.1016/J.PHYTOCHEM.2007.12.015.
  • Ma YQ, Jiang K, Deng Y, Guo L, Wan YQ, Tan CH. 2018. Mexicanolide-type limonoids from the seeds of Swietenia macrophylla. J Asian Nat Prod Res. 20(4):299–305. doi: 10.1080/10286020.2017.1335715.
  • Maiti A, Dewanjee S, Kundu M, Mandal SC. 2009. Evaluation of antidiabetic activity of the seeds of Swietenia macrophylla in diabetic rats. Pharm Biol. 47(2):132–136. doi: 10.1080/13880200802436703.
  • Moghadamtousi SZ, Goh BH, Chan CK, Shabab T, Kadir HA. 2013. Biological activities and phytochemicals of Swietenia macrophylla King. Molecules. 18(9):10465–10483. doi: 10.3390/molecules180910465.
  • Mootoo BS, Ali A, Motilal R, Pingal R, Ramlal A, Khan A, Reynolds WF, McLean S. 1999. Limonoids from Swietenia macrophylla and S. aubrevilleana. J Nat Prod. 62(11):1514–1517. doi: 10.1021/NP990199X.
  • Mulholland DA, Parel B, Coombes PH. 2000. The chemistry of the meliaceae and ptaeroxylaceae of southern and eastern Africa and Madagascar. COC. 4(10):1011–1054. doi: 10.2174/1385272003375941.
  • Muñoz V, Sauvain M, Bourdy G, Callapa J, Rojas I, Vargas L, Tae A, Deharo E. 2000. The search for natural bioactive compounds through a multidisciplinary approach in Bolivia. Part II. Antimalarial activity of some plants used by Mosetene Indians. J Ethnopharmacol. 69(2):139–155. doi: 10.1016/S0378-8741(99)00096-3.
  • Paiva ÉAS, Lemos-Filho JP, Oliveira DMT. 2006. Inhibition of Swietenia macrophylla (Meliaceae) seeds: the role of stomata. Ann Bot. 98(1):213–217. doi: 10.1093/AOB/MCL090.
  • Pennington TD. 2002. Mahogany carving a future. Biologist (London). 49(5):204–208.
  • Rahman AKMS, Chowdhury AKA, Ali HA, Raihan SZ, Ali MS, Nahar L, Sarker SD. 2009. Antibacterial activity of two limonoids from Swietenia mahagoni against multiple-drug-resistant (MDR) bacterial strains. J Nat Med. 63(1):41–45. doi: 10.1007/s11418-008-0287-3.
  • Rastogi RP, Mehrotra BN, editors. 1990. Compendium of Indian medicinal plants. New Delhi, Lucknow: Central Drug Research Institute and Publications & Information Directorate (India).
  • Segura-Correa R, Mata R, Anaya AL, Hernandez-Bautista B, Villena R, Soriano-Garcia M, Bye R, Lianares E. 1993. New Tetranortriterpenoids from Swietenia humilis. J Nat Prod. 56(9):1567–1574. doi: 10.1021/np50099a016.
  • Shakibaei M, Mobasheri A, Lueders C, Busch F, Shayan P, Goel A. 2013. Curcumin enhances the effect of chemotherapy against colorectal cancer cells by inhibition of NF-κB and Src protein kinase signaling pathways. PLoS One. 8(2):e57218. doi: 10.1371/journal.pone.0057218.
  • Shao K, Shen L, Wu J. 2015. Limonoids from Indian mangrove, seeds of Xylocarpus moluccensis. Chin Tradit Herb Drugs. 46(15):2198–2205. doi: 10.7501/J.ISSN.0253-2670.2015.15.003.
  • Solomon KA, Malathi R, Rajan SS, Narasimhan S, Nethaji M. 2003. Swietenine. Acta Crystallogr E Struct Rep Online. 59(10):o1519–o1521. doi: 10.1107/S1600536803020476.
  • Sondengam BL, Kamga CS, Connolly JD. 1980. Proceranolide, a novel tetranortriterpenoid from Carapa procera [seeds]. Phytochemistry. 19(11):2488–2488. doi: 10.1016/S0031-9422(00)91064-1.
  • Taylor ARH, Taylor DAH. 1983. Limonoid extractives from Swietenia macrophylla. Phytochemistry. 22(12):2870–2871. doi: 10.1016/S0031-9422(00)97721-5.
  • Wu SF, Lin CK, Chuang YS, Chang FR, Tseng CK, Wu YC, Lee JC. 2012. Anti-hepatitis C virus activity of 3-hydroxy caruilignan C from Swietenia macrophylla stems. J Viral Hepat. 19(5):364–370. doi: 10.1111/j.1365-2893.2011.01558.x.
  • Cheng YB, Chien YT, Lee JC, Tseng CK, Wang HC, Lo IW, Wu YH, Wang SY, Wu YC, Chang FR. 2014. Limonoids from the seeds of Swietenia macrophylla with inhibitory activity against dengue virus 2. J Nat Prod. 77(11):2367–2374. doi: 10.1021/np500282910.1021/np5002829.

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