DOI: https://doi.org/10.14710/jksa.27.7.307-315

A Cycloartane Triterpenoid and Steroid from The Leaves of Aglaia shawiana Merr. (Meliaceae)

1Department of Chemistry, Faculty of Mathematics and Natural Sciences, Nusa Bangsa University, Bogor 16166, Indonesia

2Research Center for Pharmaceutical Ingredients and Traditional Medicine, National Research, and Innovation Agency (BRIN), Kawasan Sains dan Teknologi (KST) B.J Habibie (PUSPIPTEK) Serpong, South Tangerang, Banten, Indonesia

Received: 13 Apr 2024; Revised: 10 Jun 2024; Accepted: 25 Jun 2024; Published: 31 Jul 2024.
Open Access Copyright 2024 Jurnal Kimia Sains dan Aplikasi under http://creativecommons.org/licenses/by-sa/4.0.

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Abstract
Natural products and their structural analogs are the main sources of pharmacotherapy. Various Aglaia species have been investigated since the 1960s for their phytochemical constituents and biological properties. This research focuses on isolating the terpenoid group from Aglaia shawiana, to provide a basis for further research to identify lead compounds for drug development. The hexane extract of Aglaia shawiana leaves was isolated using vacuum liquid chromatography and gravity column chromatography, employing solvents with varying polarities. The isolation process yielded two compounds: compound 1 and compound 2. A total of 15 mg of a pure isolate was obtained for compound 1, and 4.5 mg for compound 2. Their structures were characterized using 1D NMR (¹H, 13C, DEPT 135) and 2D NMR (HMQC, HMBC, 1H-1H COSY) and by comparing them with previously reported spectral data. It was concluded that compound 1 has the molecular formula C30H50O3, is a triterpenoid type cycloartane, and is named cycloartan-3β,29-diol-24-one, while compound 2 has the molecular formula C30H52O, is a steroid compound, and is named 23a-homostigmast-5en-3β-ol. These compounds were discovered for the first time in this species.
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Keywords: glaia shawiana; Elucidation; Isolation; Natural; Meliaceae
Funding: National Research and Innovation Agency (BRIN) IndonesiaI64/II/HK/2022

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Section: Research Articles
Language : EN
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  1. Ngoc T. N. Ngo, Ngan T. D. D. T. Lai, Hao C. Le, Le-Thu T. Nguyen, Binh T. D. Trinh, Hiep D. Nguyen, Phuoc D. Pham, Son V. Dang, Lien-Hoa D. Nguyen, Chemical constituents of Aglaia elaeagnoidea and Aglaia odorata and their cytotoxicity, Natural Product Research, 36, 6, (2022), 1494-1502 https://doi.org/10.1080/14786419.2021.1893723
  2. Desi Harneti, Unang Supratman, Phytochemistry and biological activities of Aglaia species, Phytochemistry, 181, (2021), 112540 https://doi.org/10.1016/j.phytochem.2020.112540
  3. Hisashi Kato-Noguchi, Masahiko Suzuki, Kazutaka Noguchi, Osamu Ohno, Kiyotake Suenaga, Chamroon Laosinwattana, A Potent Phytotoxic Substance in Aglaia odorata Lour, Chemistry & Biodiversity, 13, 5, (2016), 549-554 https://doi.org/10.1002/cbdv.201500175
  4. Desi Harneti, Roekmiati Tjokronegoro, Agus Safari, Unang Supratman, Xe-Min Loong, Mat Ropi Mukhtar, Khalit Mohamad, Khalijah Awang, Hideo Hayashi, Cytotoxic triterpenoids from the bark of Aglaia smithii (Meliaceae), Phytochemistry Letters, 5, 3, (2012), 496-499 https://doi.org/10.1016/j.phytol.2012.04.013
  5. Desi Harneti, Asep Supriadin, Mariam Ulfah, Agus Safari, Unang Supratman, Khalijah Awang, Hideo Hayashi, Cytotoxic constituents from the bark of Aglaia eximia (Meliaceae), Phytochemistry Letters, 8, (2014), 28-31 https://doi.org/10.1016/j.phytol.2014.01.005
  6. Ace Tatang Hidayat, Kindi Farabi, Desi Harneti, Nurlelasari Nurlelasari, Rani Maharani, Ida Nurfarida, Unang Supratman, Yoshihito Shiono, Cytotoxic Triterpenoids from the Stembark of Aglaia argentea (Meliaceae), Indonesian Journal of Chemistry, 18, 1, (2018), 35-42 https://doi.org/10.22146/ijc.25052
  7. Ricson P. Hutagaol, Desi Harneti, Ace T. Hidayat, Nurlelasari Nurlelasari, Rani Maharani, Dewa Gede Katja, Unang Supratman, Khalijah Awang, Yoshihito Shiono, (22E,24S)-24-Propylcholest-5en-3α-acetate: A New Steroid from the Stembark Aglaia angustifolia (Miq.) (Meliaceae), Molbank, 2020, 1, (2020), M1112 https://doi.org/10.3390/M1112
  8. Ricson Pemimpin Hutagaol, Ihsan Rahadian, Desi Harneti, Ace Tatang Hidayat, Khalijah Awang, Yoshihito Shiono, Srikandi Srikandi, Unang Supratman, A Nortriterpenoid and Steroid from the Stem Bark of Aglaia angustifolia Miq (Meliaceae), Jurnal Kimia Valensi, 8, 1, (2022), 106-112 https://doi.org/10.15408/jkv.v8i1.23011
  9. Kindi Farabi, Desi Harneti, Darwati, Nurlelasari, Tri Mayanti, Rani Maharani, Unang Supratman, Sofa Fajriah, Hadi Kuncoro, Mohamad Nurul Azmi, Yoshihito Shiono, New dammarane-type triterpenoids from Aglaia elliptica (C.DC.) blume, Natural Product Research, 38, 2, (2024), 227-235 https://doi.org/10.1080/14786419.2022.2114472
  10. Pei-Qi Huang, Jie-Wen Deng, Yang Li, Zi-Bin Liao, E. Zhao, Yun-Cai Tian, Yi-Dong Tu, Dong-Li Li, Jing-Wei Jin, Chang-Xin Zhou, Ri-Hui Wu, Li-She Gan, Terpenoids from the twigs and leaves of Aglaia elaeagnoidea and their chemotaxonomic significance, Biochemical Systematics and Ecology, 103, (2022), 104427 https://doi.org/10.1016/j.bse.2022.104427
  11. Keying Liu, Jue Yang, Yunyan Tang, Yanan Li, Zhanxing Hu, Xiaojiang Hao, Ping Yi, Chunmao Yuan, Bioassay-guided isolation of anti-leukemic steroids from Aglaia abbreviata by inducing apoptosis, Bioorganic Chemistry, 144, (2024), 107147 https://doi.org/10.1016/j.bioorg.2024.107147
  12. Afrezza Lukman Rosyid, Enny Fachriyah, Dewi Kusrini, Isolasi, Identifikasi dan Uji Aktivitas Senyawa Triterpenoid Rimpang Bengle (Zingiber cassumunar Roxb.) sebagai Antibakteri, Jurnal Kimia Sains dan Aplikasi, 19, 1, (2016), 1-6 https://doi.org/10.14710/jksa.19.1.1-6
  13. Surya Dewi Marliyana, Fajar Rakhman Wibowo, Desi Suci Handayani, Triana Kusumaningsih, Venty Suryanti, Maulidan Firdaus, Ema Nur Annisa, Stigmasterol and Stigmasterone from Methanol Extract of Calophyllum soulattri Burm. F. Stem Bark, Jurnal Kimia Sains dan Aplikasi, 24, 4, (2021), 108-113 https://doi.org/10.14710/jksa.24.4.108-113
  14. Bongani Sicelo Dlamini, Chiy-Rong Chen, Ya-Lin Chang, Pei-Hsuan Ho, Chia-Ho Chao, Chi- I. Chang, Characterization of four new cycloartane triterpenoids from Swietenia macrophylla and their angiotensin-I-converting enzyme inhibitory activity, Fitoterapia, 174, (2024), 105862 https://doi.org/10.1016/j.fitote.2024.105862
  15. Sibei Wang, Zhaoyu Shi, Han Zhang, Jiantong Hou, Dongho Lee, Jing Xu, Yuanqiang Guo, Cycloartane-type triterpenoids and steroids from Trichilia connaroides and their multidrug resistance reversal activities, Phytochemistry, 216, (2023), 113867 https://doi.org/10.1016/j.phytochem.2023.113867
  16. Akira Inada, Hiroko Murayta, Yuka Inatomi, Tsutomu Nakanishi, Dedy Darnaedi, Cycloartane Triterpenes from the Leaves of Aglaia harmsiana, Journal of Natural Products, 58, 7, (1995), 1143-1146 https://doi.org/10.1021/np50121a030
  17. Anne-Marie Nyemba, Theophile Ngando Mpondo, Joseph D. Connolly, David S. Rycroft, Cycloartane derivatives from Garcinia lucida, Phytochemistry, 29, 3, (1990), 994-997 https://doi.org/10.1016/0031-9422(90)80067-Q
  18. Mohammad Ataullah Khan, Shaikh Sirajuddin Nizami, Muhammad Najmul Islam Khan, Syed Wasif Azeem, Zaheer Ahmed, New Triterpenes from Mangifera indica, Journal of Natural Products, 57, 7, (1994), 988-991 https://doi.org/10.1021/np50109a018
  19. Ishrat Naz, Saifullah, M. R. Khan, Nematicidal Activity of Nonacosane-10-ol and 23a-Homostigmast-5-en-3β-ol Isolated from the Roots of Fumaria parviflora (Fumariaceae), Journal of Agricultural and Food Chemistry, 61, 24, (2013), 5689-5695 https://doi.org/10.1021/jf401309r
  20. Miguel Martínez, Bonifacia Benítez, Sandra Alvarez, Rebeca Prieto, Mónica Rolón, Gil Valdo José Da Silva, José A. Bravo, José L. Vila, Determination of An Active Principle of Polygonum Punctatum Elliot; Full NMR Spectra of Stigmast-5-En-3β-Ol (500/125 Mhz), Revista Boliviana de Química, 34, 1, (2017), 14-27
  21. Jan-Michael C. Cayme, Consolacion Y. Ragasa, Structure elucidation of β-stigmasterol and β-sitosterol from Sesbania grandifora [Linn.] Pers. and β-carotene from Heliotropium indicum Linn. by NMR spectroscopy, KIMIKA, 20, 1, (2004), 5-12

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