Cytotoxic Sesquiterpenoids from the Stem Bark of  Aglaia harmsiana  (Meliaceae)

Hersa Milawati; Winda Sukmawati; Desi Harneti; Rani Maharani; Nurlelasari Nurlelasari; Ace Tatang Hidayat; Darwati Darwati; Unang Supratman; Yoshihito Shiono

doi:10.22146/ijc.47808

Cytotoxic Sesquiterpenoids from the Stem Bark of Aglaia harmsiana (Meliaceae)

https://doi.org/10.22146/ijc.47808

Hersa Milawati⁽¹⁾, Winda Sukmawati⁽²⁾, Desi Harneti⁽³⁾, Rani Maharani⁽⁴⁾, Nurlelasari Nurlelasari⁽⁵⁾, Ace Tatang Hidayat⁽⁶⁾, Darwati Darwati⁽⁷⁾, Unang Supratman^(8*), Yoshihito Shiono⁽⁹⁾

(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; Central Laboratory of 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) Department of Food, Life, and Environmental Science, Faculty of Agriculture, Yamagata University, Tsuruoka, Yamagata 997-8555, Japan
(*) Corresponding Author

Abstract

Three aromadendrane-type sesquiterpenoids, spathulenol (1), 4β,10α-dihydroxyaromadendrane (2), and 4α,10α-dihydroxyaromadendrane (3) were isolated from the stem bark of Aglaia harmsiana (Meliaceae). Compound 3 was isolated for the first time from Aglaia genus. The chemical structures of isolated compounds were elucidated by various spectroscopic methods, including one and two-dimensional NMR, as well as mass spectroscopy analysis. These sesquiterpenoids 1-3 were evaluated for their cytotoxic activity against MCF-7 breast cancer cell lines. The IC₅₀ value of compound 1-3 were 31.65 ± 0.1, 8.41 ± 0.04 and 2.80 ± 0.02 µM, respectively. Among the aromadendrane-type sesquiterpenoids, compounds 2 and 3, which do not have a double bond, showed higher activity than compound 1. Whereas, compound 3 showed the strongest activity indicate that α configuration of hydroxyl group increases the cytotoxic activity.

Keywords

Aglaia harmsiana; cytotoxic activity; aromadendrane-type sesquiterpenoid; MCF-7 cell lines

Full Text:

Full Text PDF Full Text PDF-Suppl. Data

References

[1] Ludwiczuk, A., Skalicka-Woźniak, K., and Georgiev, M.I., 2017, “Terpenoids” in Pharmacognosy, Eds. Badal, S., and Delgoda, R., Academic Press, London, United Kingdom, 233–266.

[2] Connolly, J.D., and Hill, R.A., 1991, Dictionary of Terpenoids, Chapman & Hall, London.

[3] Durán-Peña, M.J., Botubol Ares, J.M., Hanson, J.R., Collado, I.G., and Hernández-Galán, R., 2015, Biological activity of natural sesquiterpenoids containing a gem-dimethylcyclopropane unit, Nat. Prod. Rep., 32 (8), 1236–1248.

[4] Joycharat, N., Plodpai, P., Panthong, K., Yingyongnarongkul, B., and Voravuthikunchai, S.P., 2010, Terpenoid constituents and antifungal activity of Aglaia forbessi seed against phytopathogens, Can. J. Chem., 88 (9), 937–944.

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

[6] Harneti, D., Supriadin, A., Ulfah, M., Safari, A., Supratman, U., Awang, K., and Hayashi, H., 2014, Cytotoxic constituents from the bark of Aglaia eximia (Meliaceae), Phytochem. Lett., 8, 28–31.

[7] Sianturi, J., Purnamasari, M., Darwati, Harneti, D., Mayanti, T., Supratman, U., Awang, K., and Hayashi, H., 2015, New bisamide compounds from the bark of Aglaia eximia (Meliaceae), Phytochem. Lett., 13, 297–301.

[8] Awang, K., Loong, X.M., Leong, K.H., Supratman, U., Litaudon, M., Mukhtar, M.R., and Mohamad, K., 2012, Triterpenes and steroids from the leaves of Aglaia exima (Meliaceae), Fitoterapia, 83 (8), 1391–1395.

[9] Hidayat, A.C., Farabi, K., Harneti, D., Nurlelasari, Maharani, R., Nurfarida, I., Supratman, U., and Shiono, Y., 2018, Cytotoxic triterpenoids from the stembark of Aglaia argentea (Meliaceae), Indones. J. Chem., 18 (1), 35–42.

[10] Farabi, K., Harneti, D., Nurlelasari, Maharani, R., Hidayat, A.T., Awang, K., Supratman, U., and Shiono, Y., 2017, New cytotoxic protolimonoids from the stem bark of Aglaia argentea (Meliaceae), Phytochem. Lett., 21, 211–215.

[11] Inada, A., Murayta, H., Inatomi, Y., Nakanishi, T., and Darnaedi, D., 1995, Cycloartane triterpenes from the leaves of Aglaia harmsiana, J. Nat. Prod., 58 (7), 1143–1146.

[12] Inada, A., Ohtsuki, S., Sorano, T., Murata, H., Inatomi, Y., Darnaedi, D., and Nakanishi, T., 1997, Cycloartane triterpenoids from Aglaia harmsiana, Phytochemistry, 46 (2), 379–381.

[13] Nugroho, B.W., Gussregen, B., Wray, V., Witte, L., Bringmann, G., and Proksch, P., 1997, Insecticidal rocaglamida derivative from Aglaia elliptica and A. harmsiana, Phytochemistry, 45 (8), 1579–1585.

[14] Kurniasih, N., Milawati, H., Fajar, M., Hidayat, A.T., Abdullah, R., Harneti, D., Supratman, U., and Azmi, M.N., 2018, Sesquiterpenoids compounds from the stembark of Aglaia minahassae (Meliaceae), Molekul, 13 (1), 56–62.

[15] Inada, A., Shono, K., Murata, H., Inatomi, Y., Darnaedi, D., and Nakanishi, T., 2000, Three putrescine bisamides from the leaves of Aglaia grandis, Phytochemistry, 53 (8), 1091–1095.

[16] Liu, S., Liu, S.B., Zuo, W.J., Guo, Z.K., Mei, W.L., and Dai, H.F., 2014, New sesquiterpenoids from Aglaia odorata var. microphyllina and their cytotoxic activity, Fitoterapia, 92, 93–99.

[17] Vieira, I.J.C., Figueiredo, E.R., Freitas, V.R., Mathias, L., Braz-Filho, R., and Araujo, R.M., 2010, A new sesquiterpene from Trichilia casaretii (Meliaceae), Am. J. Anal. Chem., 2, 70–72.

[18] Camarillo, I.G., Xiao, F., Madhivanan, S., Salameh, T., Nichols, M., Reece, L.M., Leary, J.F., Otto, K.J., Natarajan, A., Ramesh, A., and Sundararajan, R., 2014, “Low and high voltage electrochemotherapy for breast cancer: An in vitro model study” in Electroporation-Based Therapies for Cancer, Eds. Sundararajan, R., Woodhead Publishing, Cambridge, United Kingdom, 55–102.

[19] Machana, S., Weerapreeyakul, N., Barusrux, S., Nonpunya, A., Sripanidkulchai, B., and Thitimetharoch, T., 2011, Cytotoxic and apoptotic effect of six herbal plants against the human hepatocarcinoma (HepG2) cell line, Chin. Med., 6 (39), 1–8.

[20] 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.

DOI: https://doi.org/10.22146/ijc.47808