Cytotoxic Steroids From The Stembak of Chisocheton celebicus KOORD

Dewa Gede Katja, Desi Harneti, Tri Mayanti, Nurlelasari Nurlelasari, Rani Maharani, Yoshihito Shiono, Unang Supratman

Abstract


In the course of our continuing search for anticancer compounds from Chisocheton species, three steroids, stigmast-5-en-3β-ol (1), stigmast-5-en-3β-ol-3-O-β-D-glucopyranoside (2) and stigmast-5,22-dien-3β-ol-3-O-β-D-glucopyranoside (3), were obtained from the stembark of Chisocheton celebicus. The structures of compound 1-3 were identified with spectroscopic data including IR, 1D-NMR, 2D-NMR and TOF-MS, as well as by comparing with those spectral data previously. Compounds 1-3, were evaluated for their cytotoxic effects against P-388 murine leukemia cells and displayed the cytotoxicity activity with IC50 values of 12.45 ± 0.050, 52.27 ± 0.031 and 62.52 ± 0.076 µg/mL, respectively.


Keywords


Chisocheton celebicus koord; cytotoxic activity; Meliaceae; P-388 murine leukemia cells; steroid

References


Alley MC, Scudiero DA, Monks A, Hursey ML, Czerwinski MJ, Fine DL, Abbott BJ, Mayo JG, Shoemaker RH, Boyd MR. 1988. Feasibility of drug screening with panels of tumor cell lines using a microculturetetrazolium assay. Cancer Research. 48: 589-601

Cayme J, Ragasa C. 2004. Structure elucidation of β-stigmasterol and β-sitosterol from Sesbania grandiflaora (Linn). Pers. and β-carotene from Heliotropium indicum Linn by NMR spectroscopy. J. Kimika. 20: 5-12.

Chaturvedula VSP, Prakash I. 2012. Isolation of stigmasterol and -sitosterol from the dichloromethane extract of Rubus suavissimus. Int. Curr. Pharm. J. 1: 239-242.

Farabi K, Harneti D, Nurlelasari, Maharani R, Hidayat AC, Supratman U, Awang K, Shiono Y. 2017. Cytotoxic steroids from the bark of aglaia argentea (Meliaceae). CMU J. Nat. Sci. 16(4): 293-306.

Hakim EH, Achmad SA, Juliawaty LD, Makmur L, Syah YM, Aimi A, Kitajima M, Takayama H, Ghisalberti EL. 2007. Prenylated flavonoids and related compounds of the Indonesian Artocarpus (Moraceae). J. of Nat. Med. 61(2): 229-236.

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.

Inada A, Sukemawa M, Murata H, Nakanishi T, Tokuda H, Nishino H, Iwashima, Darnaedi DJ, Murata J. 1993. Phytochemical studies on Maleaceous plant. part VIII. structures and inhibitory effects on Epstein-Barr virus activation of triterpenoid from leaves of Chisocheton macrophyllus King. Chem. Pharm. Bull. 41(3): 617-619.

Katja DG, Farabi K, Nurlelasari, Harneti D, Mayanti T, Supratman U, Awang K, Hayashi H. 2017a. Cytototoxic constituents from the bark of Chisocheton cumingianus (Meliaceae). Journal of Asian Natural Products Research. 6: 1-5.

Katja DG, Farabi K, Nurlelasari, Harneti D, Maharani R, Julaeha E, Hidayat AT, Mayanti T, Supratman U. 2017b. cytotoxic steroids from the stem bark of chisocheton cumingianus (Meliaceae). Molekul. 12(1): 1-7.

Laphookhieo S, Maneerat W, Koysomboon S, Kiattansakul R, Chantrapromma K, Syers JK. 2008. A novel limonoid from the seeds of Chisocheton siamensis. Can. J. Chem. 86: 205-208.

Maneerat W, Laphoohiero S, Koysomboon S, Chantrapromma K. 2008. Antimalarial, antimycobacterial and cytotoxic limonoid from Chisocheton siamensis. Phytomedicine. 15: 1130-1134.

Mohamad K, Hirasawa Y, Litaudon M, Awang K, Hamid A, Takeya K, Ekasari W, Widyawaruyanti A, Zaini NC, Morita H. 2009. Ceramicines B-D, new antiplasmodial limonoids from Chisocheton ceramicus. Bioorganic & Medicinal Chemistry. 17: 727-730.

Najmuldeen IA, Hadi AHA, Awang K, Mohamad K, Ketuly KA, Mukhtar MR, Chong SL, Chan G, Nafiah MA, Weng NS, Shirota O, Hosoya T, Nugroho A, Morita H. 2011. Chisomicines A-C, limonoids from Chisocheton ceramicus. J. Nat. Prod. 74: 1313-1317.

Nurlelasari, Katja DG, Harneti D, Wardayo MM, Supratman U, Awang K. 2017. limonoids from the seeds of Chisocheton macrophyllus. Chemistry of Natural Compounds: 53(1): 83-87.

Phongmaykin J, Kumamoto T, Ishikawa T, Suttisri R, Saifah E. 2008. A New sesquiterpene and other terpenoid constituents of Chisocheton penduliflorus. Arch Pharm Res. 31: 21-27.

Supriatno, Nurlelasari, Herlina T, Harneti D, Maharani R, Hidayat AT, Mayanti T, Supratman U, Azmi MN, Shiono Y. 2018. A new limonoid from stem bark of Chisocheton pentandrus (Meliaceae). Natural Products Research. 1: 1-6.

Supratman U, Naibaho W, Salam S, Maharani R, Hidayat AT, Harneti D, Nurlelasari, Shiono Y. 2019. Cytotoxic triterpenoids from the bark of Chisocheton patens Blume (Meliaceae). Phytochemistry Letters. 30: 81-87.

Vossen VD, Umali BE. (Editors). 2002. Plant resources of south-east Asia no. 14 vegetable oils and fats, Prosea Foundation, Bogor, Indonesia. 150.

Yang MH, Wang JG, Luo JG, Wang XB, Kong LY. 2011. Chisopanins A-K, 11 new protolimonoids from Chisocheton paniculatus and their anti-inflammatory activities. Bioorganic & Medicinal Chemistry. 19: 1409-1417.

Yang MH, Wang JS, Luo JG, Wang XB, Kong LY. 2009. Tetranortriterpenoids from Chisocheton Paniculatus. J. Nat. Prod. 70: 1532-1532.

Wong CP, Shimada M, Nagakura Y, Nugroho AE, Hirasawa Y, Kaneda T, Awang K, Hamid A, Hadi A, Mohamad K, Shio M, Morita H. 2011. Ceramicines E-I, new limonoids from Chisocheton ceramicus. Chem. Farm. Bull. 59: 407-411

Zhang F, Feng HE, Bin W, Sheningg C, Mian Y. 2012. New apotirucallane type triterpenoid from Chisocheton paniculatus. Nat. Prod. Bioprospect. 2: 235-239.


Full Text: PDF

DOI: 10.15408/jkv.v5i2.12132

Refbacks

  • There are currently no refbacks.


Copyright (c) 2019 Dewa Gede Katja

Creative Commons License
This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.