Ergosterol Peroxide and Stigmasterol from The Stembark of Aglaia simplicifolia (Meliaceae) and Their Cytotoxic against HeLa Cervical Cancer Cell Lines
Abstract
Two steroid compounds, ergosterol peroxide (1) and stigmasterol (2) have been isolated from the stembark of Aglaia simplicifolia belong to Meliaceae family. The chemical structures of 1 and 2 were identified based on spectroscopic evidence including UV, IR, 1D NMR, 2D NMR as well as mass spectra and by comparison with those previously reported spectra data. Both compounds were evaluated for their cytotoxic effects against cervical cancer HeLa cells in vitro. Compounds 1 and 2 showed cytotoxicity activity against HeLa cervical cancer cells with IC50 values of 0.80 and 26.42 µM, respectively.
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References
Awang K, Loong XM, Leong KH, Supratman U, Litaudon M, Mukhtar MR, Mohamad K. 2012. Triterpenes and steroids from the leaves of Aglaia exima (Meliaceae). Fitoterapia 83:1391-1395.
Cai X, Wang Y, Zhao P, Li Y, Luo X. 2010. Dolabellane diterpenoids from Aglaia odorata. Phytochemistry. 71:1020–1024.
Cayme J, Ragasa C. 2004. Structure elucidation of -stigmasterol and - sitosterol from Sesbania grandiflora (Linn). Pers and -carotene from Heliotropium indicum Linn by NMR spectroscopy. Journal Kimika. 20:5-12.
Farabi K, Harneti D, Nurlelasari, Maharani R., Hidayat AC, Awang K., Supratman U, Shiono Y. 2017. New cytotoxic protolimonoids from the stem bark of Aglaia argentea (Meliaceae). Phytochemistry Letters. 21:211-215.
Harneti D, Supratman U. 2021. Phytochemistry and biological activities of Aglaia species. Phytochemistry 181:112540
Harneti D, Supriadin A, Ulfah M, Safari A, Supratman U, Awang K, Hayashi H. 2014. Cytotoxic constituents from the bark of Aglaia eximia (Meliaceae). Phytochem. Lett. 8:28–31.
Harneti D, Tjokronegoro R, Safari A, Supratman U, Loong XM, Mukhtar MR, Mohamad K, Awang K, Hayashi H. 2012. Cytotoxic triterpenoids from the bark of Aglaiasmithii. Phytochemistry Letters. 5:496–499.
Heyne K. 1982. The Useful Indonesian Plants. Jakarta: Ministry of Forestry.
Hidayat AT, Farabi K, Harneti D, Nurlelasari, Maharani R, Mayanti T, Supratman U, Shiono Y. 2017a. A Cytotoxic Rocaglate Compound from The Stembark of Aglaia argentea (Meliaceae). Molekul. 2:146-152.
Hidayat AT, Farabi K, Harneti D, Maharani R, Darwati, Nurlelasari, Mayanti T, Arlette SSAS, Supratman U, Shiono Y. 2017b. Cytotoxicity and Structure Activity Relationship of Dammarane-TypeTriterpenoids from the Bark of Aglaia elliptica against P-388 Murine Leukemia Cells. Natural Product Sciences. 4:291-298.
Joycharat N, Plodpai P, Panthong K, Yingyongnarongkul B, Voravuthikunchai SP. 2010. Terpenoid constituents and antifungal activity of Aglaia forbesii seed against phytopathogens. Canadian Journal of Chemistry. 88:937–944.
Kurniasih N, Milawati H, Fajar M, Hidayat AT, Abdulah R, Harneti D, Supratman U, Azmi MN. 2018. Sesquiterpenoid Compounds from The Stembark of Aglaia minahassae (Meliaceae). Molekul. 13 (1):56-62.
Kurniasih N, Supriadin A, Fajar M, Abdulah R, Harneti D, Supratman U, Azmi MN. 2019. Cytotoxic sesquterpenoid compound from the stembark of Aglaia simplicifolia (Meliaceae). J. Phys.: Conf. Ser. 1402 055037
Leong KH, Looi CY, Loong XW, Cheah FK, Supratman U, Litaudon M, Mohd Rais Mustafa MR, Awang K. 2016. Cycloart-24-ene-26-ol-3-one, a New Cycloartane Isolated from Leaves of Aglaia exima Triggers Tumour Necrosis Factor- Receptor 1-Mediated Caspase-Dependent Apoptosis in Colon Cancer Cell Line. PLOS ONE. 4:1-17.
Liu S, Liu SB, Zuo W, Guo Z, Mei W, Dai H. 2014. New sesquiterpenoids from Aglaia odorata var. microphyllina and their cytotoxic activity. Fitoterapia. 92:93–99.
Nowak R, Drozd M, Mendyk E, Lemieszek M, Krakowiak O, Kisiel W, Rzeski W, Szewczyk K, 2016. A New Method for the Isolation of Ergosterol and Peroxyergosterol as Active Compounds of Hygrophoropsis aurantiaca and in Vitro Antiproliferative Activity of Isolated Ergosterol Peroxide. Molecules. 21: 946
Nugroho BW, Edrada RA, Wray V, Witte L, Bringmann G, Gehling M, Proksch P. 1999. An insectisidal rocaglamida derivates and related compounds from Aglaia odorata (Meliaceae). Phytochemistry. 51:367-376.
Pan L, Kardono LBS, Riswan S, Chai H, Carcache de Blanco EJ, Pannell CM, Soejarto DD, McCloud TG, Newman DJ, Kinghorn AD. 2010. Isolation and characterization of minor analogues of silvestrol and other constituents from a large-scale re-collection of Aglaia foveolata. Journal of Natural Products. 4: 1873–1878.
Sianturi J, Harneti D, Darwati, Mayanti T, Supratman U, Awang K. 2016. A New(–)-5′,6-dimethoxyisolariciresinol-(3′′,4′′-dimethoxy)-3α-O-β-glucopyranoside from the bark of Aglaia eximia (Meliaceae). Natural Products Research. 30:2204-2208.
Sittampalam GS, Coussens NP, Brimacombe K, Grossman A, Arkin M, Auld D, Austin C, Baell J, Bejcek B, Caaveiro JMM, Chung TDY, Dahlin JL, Devanaryan V, Foley TL, Glicksman M, Hall MD, Haas JV, Inglese J, Iversen PW, Kahl SD, Kales SC, Lal-Nag M, Li Z, McGee J, McManus O, Riss T, Trask Jr O J, Weidner JR, Wildey MJ, Xia M, Xu X. 2018. Assay Guidance Manual. Eli Lilly & Company and the National Center for Advancing Translational Sciences Bethesda (MD).
Su B, Chai H, Mi Q, Riswan S, Kardono LBS, Afriastini JJ, Santarsiero BD, Mesecar AD, Fransworth NR, Cordell GA, Swanson SM, Kinghorn D. 2006. Activity-guided isolation of cytotoxic constituents from the bark of Aglaiacrassinervia collected in Indonesia. Bioorganic and Medicinal Chemistry. 14:960-972.
Wood D L, Silverstain R M & Nakajima M. 1970. Control of Insects Behavior by Natural Product. New York: Academic Press.
Wu HY, Yang FL, Li LH, Rao YK, Ju TC, Wong WT, Hsieh CY , Pivkin MV, Hua KF, Wu SH. 2018. Ergosterol peroxide from marine fungus Phoma sp. induces ROS-dependent apoptosis and autophagy in human lung adenocarcinoma cells. Scientific Reports 8:17956
Xie BJ, Yang SP, Chen HD, Yue JM. 2007. Triterpenoids from Aglaia duperreana. Journal of Natural Products. 70:1532-1535.
Yodsaoue O, Sonprasit J, Karalai C, Ponglimanont C, Tewtrakul S, Chantrapromma S. 2012. Diterpenoids and triterpenoids with potential anti-inflammatory activity from the leaves of Aglaia odorata. Phytochemistry. 76:83-91.
Zhang F, Wang JS, Gu YC, Kong LY. 2010. Triterpenoids from Aglaia abbreviata and their cytotoxic activities. Journal of Natural Products. 73:2042-2046.
Zhang F, Zhu Y, Li Q, Cen J. 2016. Four New Pregnane Steroids from Aglaia abbreviate and Their Cytotoxic Activities. Helv. Chim. Acta. 99:73-77.
DOI: 10.15408/jkv.v7i1.20068
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