Sesquiterpenoids from the Stem Bark of Lansium domesticum Corr. Cv. Kokossan and Their Cytotoxic Activity against MCF-7 Breast Cancer Cell Lines

https://doi.org/10.22146/ijc.72742

Siska Elisahbet Sinaga(1), Tri Mayanti(2), Al Arofatus Naini(3), Desi Harneti(4), Nurlelasari Nurlelasari(5), Rani Maharani(6), Kindi Farabi(7), Unang Supratman(8*), Sofa Fajriah(9), Mohamad Nurul Azmi(10)

(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(4) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(5) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(6) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia; Central Laboratory of Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(7) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(8) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia; Central Laboratory of Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(9) Research Center for Raw Materials for Medicine and Traditional Medicine, National Research and Innovation Agency (BRIN), Tangerang Selatan, Banten 15314, Indonesia
(10) School of Chemical Sciences, Universiti Sains Malaysia, 11800 Minden, Penang, Malaysia
(*) Corresponding Author

Abstract


The n-hexane fraction from the stem bark of Lansium domesticum Corr. Cv. Kokosan afforded 3 sesquiterpenoids, namely eudesm-4(15),7-dien-1β-ol (1), eudesm-4(15)-ene-1β,6α-diol (2), and octahydro-4-hydroxy-3a-methyl-7-methylene-a-(1-methylethyl)-1H-indene-1-methanol (3). These three compounds were discovered in the Lansium genus for the first time. Their chemical structures were determined based on data generated from various spectroscopic methods, including one- and two-dimensional NMR, as well as mass spectroscopy. Sesquiterpenoid compounds (1-3) have also been evaluated on MCF-7 breast cancer cell lines and the compound 1 showed the strongest activity with an IC50 value of 17.97 µg/mL while compounds 2 and 3 showed moderate and weak activity with IC50 values of 121.65 and 201.57 µg/mL, respectively. The implication of the findings of these compounds is as an illustration that one of these sesquiterpenoids has potential as an anticancer with the presence of double bond which played important role in the cytotoxic activity that can be studied for new drug discovery.


Keywords


cytotoxic activity; Lansium domesticum Corr. Cv. Kokosan; MCF-7 cell lines; sesquiterpenoid



References

[1] Chappell, J., and Coates, R.M., 2010, “Sesquiterpenes” in Comprehensive Natural Products II, vol. 1. Eds. Mandler, L., and Liu, H.W., Elsevier, Kidlington, United Kingdom, 609–641.

[2] Talapatra, S.K., and Talapatra, B, 2015, Chemistry of Plant Natural Products: Stereochemistry, Conformation, Synthesis, Biology, and Medicine, Springer-Verlag, Berlin Heidelberg.

[3] Gong, D.Y., Chen, X.Y., Guo, S.X., Wang, B.C., and Li, B., 2021, Recent advances and new insights in biosynthesis of dendrobine and sesquiterpenes, Appl. Microbiol. Biotechnol., 105 (18), 6597–6606.

[4] Zhao, W.Y., Yan, J., Liu, T.T., Gao, J., Huang, H.L., Sun, C.P., Huo, X.K., Deng, S., Zhang, B.J., and Ma, X.C., 2020, Natural sesquiterpenoid oligomers: A chemical perspective, Eur. J. Med. Chem., 203, 112622.

[5] Jaeger, R., and Cuny, E., 2016, Terpenoids with special pharmacological significance: A review, Nat. Prod. Commun., 11 (9), 1373–1390.

[6] Nangmo, K.P., Tsamo, T.A., Zhen, L., Mkounga, P., Akone, S.H., Tsabang, N., Müller, W.E.G., Marat, K., Proksch, P., and Mkengfack, A.E., 2018, Chemical constituents from leaves and root bark of Trichilia monadelpha (Meliaceae), Phytochem. Lett., 23, 120–126.

[7] Hou, L., Tang, G.H., Zhang, Y., Hao, X.J., Zhao, Q., and He, H.P., 2013, A new carotane sesquiterpene from Walsura robusta, Chin. J. Nat. Med., 11 (1), 84–86.

[8] Fu, L.R., Ma, Q.Y., Huang, S.Z., Dai, H.F., Guo, Z.K., Yu, Z.F., and Zhao, Y.X., 2014, Terpenoids and their anti-feedant activity from Cipadessa cinerascens, J. Asian Nat. Prod. Res., 16 (11), 1054–1059.

[9] Nugroho, A.E., Sugiura, R., Momota, T., Hirasawa, Y., Wong, C.P., Kaneda, T., Hadi, A.H.A., and Morita, H., 2015, Dysosesquiflorins A and B, sesquiterpenoids from Dysoxylum densiflorum, J. Nat. Med., 69 (3), 411–415.

[10] Huang, P.Q., Deng, J.W., Li, Y., Liao, Z.B., Zhao, E., Tian, Y.C., Tu, Y.D., Li, D.L., Jin, J.W., Zhou, C.X., Wu, R.H., and Gan, L.S., 2022, Terpenoids from the twigs and leaves of Aglaia elaeagnoidea and their chemotaxonomic significance, Biochem. Syst. Ecol., 103, 104427.

[11] Fadhilah, K., Wahyuono, S., and Astuti, P., 2021, Fractions and isolated compounds from Lansium domesticum fruit peel exhibited cytotoxic activity against T-47D and HepG2 cell lines, Biodiversitas, 22 (9), 3743–3748.

[12] Fadhilah, K., Wahyuono, S., and Astuti, P., 2020, A bioactive compound isolated from duku (Lansium domesticum Corr) fruit peels exhibits cytotoxicity against T47D cell line, F1000Res., 9, 3.

[13] Fadhilah, K., Wahyuono, S., and Astuti, P., 2020, A sesquiterpene aldehyde isolated from ethyl acetate extract of Lansium Domesticum fruit peel, Indones. J. Pharm., 3 (2), 394–398.

[14] Naini, A.A., Mayanti, T., Nurlelasari, Harneti, D., Maharani, R., Safari, A., Hidayat, A.T., Farabi, K., Lesmana, R., Supratman, U., and Shiono, Y., 2022, Cytotoxic sesquiterpenoids from Dysoxylum parasiticum (Osbeck) Kosterm. stem bark, Phytochem. Lett., 47, 102–106.

[15] Milawati, H., Sukmawati, W., Harneti, D., Maharani, R., Nurlelasari, N., Hidayat, A.T., Darwati, D., Supratman, U., and Shiono, Y., 2020, Cytotoxic sesquiterpenoids from the stem bark of Aglaia harmsiana (Meliaceae), Indones. J. Chem., 20 (6), 1448–1454.

[16] Milawati, H., Harneti, D., Maharani, R., Nurlelasari, N., Hidayat, A.T., Azmi, M.N., Shiono, Y., and Supratman, U., 2019, Caryophyllene-type sesquiterpenoids from the stembark of Aglalia harmsiana and their cytotoxic activity against MCF-7 breast cancer cells, Molekul, 14 (2), 126–132.

[17] Lubis, M.F., Hasibuan, P.A., Syahputra, H., and Astyaka, R., 2022, A Review on phytochemicals and pharmacological activities as ethnomedicinal uses of duku (Lansium domesticum Corr.), Open Access Maced. J. Med. Sci., 10 (F), 57–65.

[18] Mayanti, T., Apriantini Y.P., Soidah, S., Sianturi, J., Darneti, D., Julaeha, E., Sumiarsa, D., Nurlelasari, and Maharani, R., 2018, Antibacterial triterpenoids from the barks and leaves of Lansium domesticum Corr cv. Kokossan (Meliaceae), J. Chem., 12 (1), 54–58.

[19] Soares, L.R., de Queiroz e Silva, A.C., Freire, T.V., Garcez, F.R., and Garcez, W.S., 2012, Sesquiterpenos de sementes de Guarea guidonia (Meliaceae), Quim. Nova, 35 (2), 323–326.

[20] Zhang, H.J., Tan, G.T., Santarsiero, B.D., Mesecar, A.D., Van Hung, N., Cuong, N.M., Soejarto, D.D., Pezzuto, J.M., and Fong, H.H.S., 2003, New sesquiterpenes from Litsea verticillata, J. Nat. Prod., 66 (5), 609–615.

[21] Xu, M., McCanna, D.J., and Sivak, J.G., 2015, Use the viability reagent PrestoBlue in comparison with alamarBlue and MTT to assess the viability of human corneal epithelial cells, J. Pharmacol. Toxicol. Methods, 71, 1–7.

[22] Azizi, K., Hamedi, A., Azarpira, N., Shahini, M., and Pasdaran, A., 2021, A new cytotoxic sesquiterpene lactone from Euphorbia microsphaera Boiss against human breast cancer (MCF-7) and human fibrosarcoma (HT1080) cells, Toxicon, 202, 60–66.



DOI: https://doi.org/10.22146/ijc.72742

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