skip to main content

Isolation, Structure Determination, and Cytotoxic Activity of Steroid Compound from The Stem Bark of Aglaia cucullata (Meliaceae)

1Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jatinangor 45363, Indonesia

2Central Laboratory, Universitas Padjadjaran, Jatinangor 45363, Indonesia

Received: 12 Jul 2023; Revised: 30 Aug 2023; Accepted: 31 Aug 2023; Published: 30 Sep 2023.
Open Access Copyright 2023 Jurnal Kimia Sains dan Aplikasi under http://creativecommons.org/licenses/by-sa/4.0.

Citation Format:
Cover Image
Abstract
Steroids are one of the secondary metabolite groups that are abundant in many organisms. In plants, this type of compound is called phytosterols. Phytosterols have been widely known to show many potential bioactivities such as anti-inflammatory, induced apoptosis, cytotoxic, anti-diabetic, angiogenic, and antioxidant. One of the sources of phytosterol compounds is the genus Aglaia. As the largest genus in the Meliaceae family, the genus Aglaia contains many bioactive compounds, including steroids. This research reported the isolation, structural determination, and cytotoxic activity of steroid compounds from the stem bark of Aglaia cucullata, one of the members of the Aglaia genus. Pure isolated steroid was obtained after maceration of dried stem bark with ethanol and partitioned based on difference polarity, continued by column chromatography. Spectroscopic methods, including HRMS, FTIR, 1D and 2D NMR, were used for structural determination. The compound structure identified as stigmast-5-en-3β-ol-3β-oleate was first isolated from this species. MCF-7 breast cancer cell, B16-F10 melanoma cell, and CV-1 normal fibroblast kidney cell were used to evaluate its cytotoxicity. Stigmast-5-en-3β-ol-3β-oleate displayed low cytotoxicity against those two cancer cells and a normal cell.
Fulltext View|Download
Keywords: Steroid; Aglaia; Aglaia cucullata; cytotoxic activity
Funding: Universitas Padjadjaran under contract No. 2203/UN6.3.1/PT.00/2023

Article Metrics:

  1. Francesco Di Gioia, Spyridon A. Petropoulos, Phytoestrogens, phytosteroids and saponins in vegetables: Biosynthesis, functions, health effects and practical applications, in: Advances in Food and Nutrition Research, Elsevier, 2019, https://doi.org/10.1016/bs.afnr.2019.02.004
  2. Ronda F. Greaves, Ganesh Jevalikar, Jacqueline K. Hewitt, Margaret R. Zacharin, A guide to understanding the steroid pathway: new insights and diagnostic implications, Clinical Biochemistry, 47, 15, (2014), 5-15 https://doi.org/10.1016/j.clinbiochem.2014.07.017
  3. Soodabeh Saeidnia, Azadeh Manayi, Ahmad R. Gohari, Mohammad Abdollahi, The Story of Beta-sitosterol- A Review, European Journal of Medicinal Plants, 4, 5, (2014), 590-609 https://doi.org/10.9734/EJMP/2014/7764
  4. Tamilselvam Rajavel, Pandian Packiyaraj, Venkatesan Suryanarayanan, Sanjeev Kumar Singh, Kandasamy Ruckmani, Kasi Pandima Devi, β-Sitosterol targets Trx/Trx1 reductase to induce apoptosis in A549 cells via ROS mediated mitochondrial dysregulation and p53 activation, Scientific Reports, 8, (2018), 2071 https://doi.org/10.1038/s41598-018-20311-6
  5. Kai Qian, Xue-Xia Zheng, Chen Wang, Wen-Guang Huang, Xiao-Bao Liu, Shu-Di Xu, Dan-Kai Liu, Min-Ying Liu, Chang-Song Lin, β-Sitosterol inhibits rheumatoid synovial angiogenesis through suppressing VEGF signaling pathway, Frontiers in Pharmacology, 12, (2022), 816477 https://doi.org/10.3389/fphar.2021.816477
  6. Pei-Chun Liao, Ming-Hoang Lai, Kuang-Ping Hsu, Yueh-Hsiung Kuo, Jie Chen, Ming-Chih Tsai, Chun-Xiang Li, Xi-Jiang Yin, Narumon Jeyashoke, Louis Kuo-Ping Chao, Identification of β-sitosterol as in vitro anti-inflammatory constituent in Moringa oleifera, Journal of Agricultural and Food Chemistry, 66, 41, (2018), 10748-10759 https://doi.org/10.1021/acs.jafc.8b04555
  7. M. K. Radika, P. Viswanathan, C. V. Anuradha, Nitric oxide mediates the insulin sensitizing effects of β-sitosterol in high fat diet-fed rats, Nitric Oxide, 32, (2013), 43-53 https://doi.org/10.1016/j.niox.2013.04.007
  8. Peng Zhang, Naicheng Liu, Mingyang Xue, Mengjie Zhang, Wei Liu, Chen Xu, Yuding Fan, Yan Meng, Qinghua Zhang, Yong Zhou, Anti-Inflammatory and Antioxidant Properties of β-Sitosterol in Copper Sulfate-Induced Inflammation in Zebrafish (Danio rerio), Antioxidants, 12, 2, (2023), 391 https://doi.org/10.3390/antiox12020391
  9. Bahare Salehi, Cristina Quispe, Javad Sharifi-Rad, Natalia Cruz-Martins, Manisha Nigam, Abhay Prakash Mishra, Dmitryi Alexeevich Konovalov, Valeriya Orobinskaya, Ibrahim M. Abu-Reidah, Wissam Zam, Farukh Sharopov, Tommaso Venneri, Raffaele Capasso, Wirginia Kukula-Koch, Anna Wawruszak, Wojciech Koch, Phytosterols: From preclinical evidence to potential clinical applications, Frontiers in Pharmacology, 11, (2021), 1819 https://doi.org/10.3389/fphar.2020.599959
  10. R. Priya, P. Sowmiya, M. S. Muthuraman, An overview on the biological perspectives of Aglaia species, Asian Journal of Pharmaceutical and Clinical Research, 11, 9, (2018), 42-45 https://doi.org/10.22159/ajpcr.2018.v11i9.26436
  11. Desi Harneti, Unang Supratman, Phytochemistry and biological activities of Aglaia species, Phytochemistry, 181, (2021), 112540 https://doi.org/10.1016/j.phytochem.2020.112540
  12. Kindi Farabi, Desi Harneti, Darwati, Tri Mayanti, Nurlelasari, Rani Maharani, Aprilia Permata Sari, Tati Herlina, Ace Tatang Hidayat, Unang Supratman, Sofa Fajriah, Mohamad Nurul Azmi, Yoshihito Shiono, Dammarane-Type Triterpenoid from the Stem Bark of Aglaia elliptica (Meliaceae) and Its Cytotoxic Activities, Molecules, 27, 19, (2022), 6757 https://doi.org/10.3390/molecules27196757
  13. Wijarn Meepol, Gordon S. Maxwell, Sonjai Havanond, Aglaia cucullata: A little-known mangrove with big potential for research, ISME/GLOMIS Electron Journal, 18, 1, (2020), 4-9
  14. Firoj Ahmed, Kazufumi Toume, Samir K. Sadhu, Takashi Ohtsuki, Midori A. Arai, Masami Ishibashi, Constituents of Amoora cucullata with TRAIL resistance-overcoming activity, Organic & Biomolecular Chemistry, 8, 16, (2010), 3696-3703 https://doi.org/10.1039/C004927A
  15. Robert A. DeFilipps, Gary A. Krupnick, The medicinal plants of Myanmar, PhytoKeys, 102, (2018), 1-341 https://doi.org/10.3897/phytokeys.102.24380
  16. Parinuch Chumkaew, Shigeru Kato, Kan Chantrapromma, Potent cytotoxic rocaglamide derivatives from the fruits of Amoora cucullata, Chemical and Pharmaceutical Bulletin, 54, 9, (2006), 1344-1346 https://doi.org/10.1248/cpb.54.1344
  17. Ni Putu Ermi Hikmawanti, Sofia Fatmawati, Anindita Wulan Asri, The effect of ethanol concentrations as the extraction solvent on antioxidant activity of Katuk (Sauropus androgynus (L.) Merr.) leaves extracts, IOP Conference Series: Earth and Environmental Science, 2021 https://doi.org/10.1088/1755-1315/755/1/012060
  18. Kindi Farabi, Desi Harneti, Maharani R. Nurlelasari, A. C. Hidayat, Unang Supratman, Khalijah Awang, Yoshihito Shiono, Cytotoxic steroids from the bark of Aglaia argentea (Meliaceae), Chiang Mai University Journal of Natural Sciences, 16, 4, (2017), 293-306 https://doi.org/10.12982/CMUJNS.2017.0024
  19. Aprilia Permata Sari, Nurlelasari, Azmi Azhari, Desi Harneti, Rani Maharani, Tri Mayanti, Kindi Farabi, Darwati, Unang Supratman, Sofa Fajriah, Mohamad Nurul Azmi, Yoshihito Shiono, New Ergostane-Type Sterol Produced by an Endophytic Fungus Fusarium phaseoli Isolated from Chisocheton macrophyllus (Meliaceae), Records of Natural Products, 16, 6, (2022), 614-621 http://doi.org/10.25135/rnp.334.2203.2387
  20. Isil Gazioglu, Sevcan Semen, Ozden Ozgun Acar, Ufuk Kolak, Alaattin Sen, Gulacti Topcu, Triterpenoids and steroids isolated from Anatolian Capparis ovata and their activity on the expression of inflammatory cytokines, Pharmaceutical Biology, 58, 1, (2020), 925-931 https://doi.org/10.1080/13880209.2020.1814356
  21. Leslie D. Field, Alison M. Magill, Hsiu Liao Li, Instructor's Guide and Solutions Manual to Organic Structures from 2D NMR Spectra, John Wiley & Sons, 2015,

Last update:

No citation recorded.

Last update: 2024-12-27 12:15:39

No citation recorded.