Sains Malaysiana 49(5)(2020): 989-994

http://dx.doi.org/10.17576/jsm-2020-4905-03

 

 

Cytotoxic Triterpenoids from the Stem Barks of Dysoxylum arborescensand Dysoxylum excelsum against MCF-7 Breast Cancer Cell

 

(Triterpenoid Sitotoksik daripada Kulit Batang Dysoxylum arborescens dan Dysoxylum excelsum terhadap Sel Kanser Payudara MCF-7)

 

ACHMAD ZAINUDDIN1, SYLVIA RACHMAWATI MEILANIE1, DARWATI1, KURNIAWAN1, NURLELASARI1, TATI HERLINA1, ADRIAN RIZKY SAPUTRA1, JAMALUDIN AL ANSHORI1,2 & TRI MAYANTI1*

 

1Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km 21 Jatinangor 45363, Indonesia

 

2Laboratory of Applied Chemistry and Services, Faculty of Mathematics and Natural Sciences

Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km 21 Jatinangor 45363, Indonesia

 

Received: 11 February 2019/Accepted: 19 January 2020

 

ABSTRACT

Three triterpenoids, taraxerone (1) and 18-epi-taraxerol (2), and masticadienolic acid (3) were isolated for the first time from the stem barks of Dysoxylum arborescens and Dysoxylum excelsum, respectively. Isolation of the compounds was achieved by various extraction and chromatography column techniques, while their chemical structures were elucidated based on spectroscopic data and literature comparison. Compounds 1, 2, and 3 were found to show inhibitory activity against MCF-7 breast cancer cells with IC50 values 792.9, 59.6, and 3.5 µM correspondingly.

Keywords: Dysoxylum arborescens; Dysoxylum excelsum; MCF-7; triterpenoids

 

 

ABSTRAK

Tiga triterpenoid, tarakseron (1) dan 18-epi-tarakserol (2), asid mastikadienolat (3) telah dipisahkan daripada kulit batang Dysoxylum excelsum dan Dysoxylum arborescens buat pertama kali. Sebatian 1, 2 dan 3 dipencilkan menggunakan pelbagai teknik lajur ektraksi dan kromatografi, sementara penentuan strukturnya menggunakan bantuan data spektroskopi dan perbandingan dengan sebatian yang pernah dilaporkan sebelumnya. Aktiviti sitotoksik sebatian 1, 2 dan 3 terhadap sel kanser payudara MCF-7 menunjukkan perencatan dengan nilai IC50 masing-masing 792.9, 59.6 dan 3.5 µM.

Kata kunci: Dysoxylum arborescens; Dysoxylum excelsum; MCF-7; triterpenoid

 

REFERENCES

Duh, C.Y., Wang, S.K. & Chen, I.S. 2000. Cytotoxic prenyludesmane diterpenes from the fruits of Dysoxylum kuskusense. Journal of Natural Products 63(11): 1546-1547.

Fujioka, T., Yamamoto, M., Kashiwada, Y., Fuji, H., Mihashi, K., Ikeshiro, Y., Chen, I. & Lee, K. 1998. Novel cytotoxic diterpenes from the stem of Dysoxylum kuskusense. Tetrahedron Letters 8: 3479-3482.

Han, M.L., Zhao, J.X., Liu, H.C., Ni, G., Ding, J., Yang, S.P. & Yue, J.M. 2015. Limonoids and triterpenoids from Dysoxylum mollissimum var glaberrimum. Journal of Natural Products 78(4): 754-761.

Hu, J., Song, Y., Li, H., Mao, X., Zhao, Y., Shi, X. & Yang, B. 2014. Antibacterial and cytotoxic triterpenoids from the ethanol extract of Dysoxylum densiflorum (Blume) Miq. Phytochemistry Letters 10: 219-223.

Kurimoto, S.I., Kashiwada, Y., Lee, K.H. & Takaishi, Y. 2011. Triterpenes and a triterpene glucoside from Dysoxylum cumingianum. Phytochemistry 72: 2205-2211.

Lakshmi, V., Pandey, K. & Agarwal, S.K. 2009. Bioactivity of the compounds in genus Dysoxylum. Acta Ecologica Sinica 29: 30-44.

Liu, H., Heilmann, J., Rali, T. & Sticher, O. 2001. New tirucallane-type triterpenes from Dysoxylum variabile. Journal of Natural Products 64: 159-163.

Luo, X., Wu, S., Ma, Y. & Wu, D. 2000. Tirucallane triterpenoids from Dysoxylum hainanense. Phytochemistry 54(8): 801-805.

Mabberley, D.J. 2008. 14. Dysoxylum Blume, Bijdr. 172. 1825. China. Fl. China 11: 125-129.

Makino, M., Motegi, T. & Fujimoto, Y. 2003. Tirucallane-type triterpenes from Juliania adstringens. Phytochemistry 65: 891-896.

Mejin, M. 2009. Isolation, structural elucidation and antibacterial activity of the chemical constituents of Scaevola spinescens. Theses MSc. The University of Adelaide. Adelaide, South Australia (Unpublished).

Mohammad, K., Martin, M.T., Litaudon, M., Gaspard, C., Sévenet, T. & Païs, M. 1999. Tirucallane triterpenes from Dysoxylum macranthum. Phytochemistry 52: 1461-1468.

Mosmann, T. 1983. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. Journal of Immunological Methods 65(1-2): 55-63.

Morita, H., Nugroho, A.E., Nagakura, Y., Hirasawa, Y., Yoshida, H., Kaneda, T., Shirota, O. & Ismail, I.S. 2014. Chrotacumines A-D, chromone alkaloids from Dysoxylum acutangulum with osteoclast differentiation inhibitory activity. Bioorganic & Medicinal Chemistry Letter 24: 2437-2439.

Nugroho, A.E., Sugiura, R., Momota, T., Hirasawa, Y., Wong, C.P., Kaneda, T., Hadi, A.H.A. & Morita, H. 2015. Dysosesquiflorins A and B, sesquiterpenoids from Dysoxylum densiflorum. Journal of Natural Medicines 69(3): 411-415.

Prakash, O., Ahmad, A., Tripathi, V.K., Tandon, S. & Pant, A.B. 2014. In silico assay development for screening of tetracyclic triterpenoids as anticancer agents against human breast cancer cell line MCF7. PLoS ONE 9(11): e111049.

Ragasa, C.Y., Ebajo Jr., V.D., Antonio, S., Ng, M.M., De Los, R. & Shen, C.C. 2014. Chemical constituents of Strongylodon macrobotrys. Der Pharma Chemica 6(6): 366-373.

Shibahara, Y., Miki, Y., Onodera, Y., Hata, S. & Chan, M.S. 2012. Aromatase inhibitor treatment of breast cancer cells increases the expression of let-7f, amicroRNA targeting CYP19A1. The Journal of Pathology 227: 357-366.

Unang, S., Wiro, N., Supriatno, S., Rani, M., Ace, T.H., Desi, H., Nurlelasari. & Yoshihito, S. 2019. Cytotoxic triterpenoids from the bark of Chisocheton patens Blume (Meliaceae). Phytochemistry Letters 30: 81-87.

Wah, L.K., Abas, F., Cordell, G.A., Ito, H. & Ismail, I.S. 2013. Steroids from Dysoxylum grande (Meliaceae) leaves. Steroids 78: 210-219.

Zhou, B., Shen, Y., Wu, Y., Leng, Y. & Yue, J.M. 2015. Limonoids with 11β-hydroxysteroid dehydrogenase type 1 inhibitory activities from Dysoxylum mollisimum. Journal of Natural Products 78(8): 2116-2122.

 

*Corresponding author; email: t.mayanti@unpad.ac.id

 

 

 

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