Isolation of Artonin E from the root bark of Artocarpus rigida, synthesis of Artonin E acetate and evaluation of anticancer activity

Tati Suhartati, Hernawan Hernawan, Jhons F. Suwandi, Yandri Yandri, Sutopo Hadi

Abstract


Artonin E was isolated from the root bark of A. rigida. The isolated compound was then esterified using a known procedure by the addition of acetic anhydride with pyridine catalyst. The structure of the synthesized compound was carefully determined by physical and spectroscopic techniques and compared to the data in the literature. The anticancer activity test against murine leukemia cancer cells P-388 showed that the ester compound has good activity with an IC50 of 2.79 μg/mL and much better stability during storage compared to Artonin E itself.


Keywords


A. rigida; artonin E acetate; esterification; anticancer activity

Full Text:

PDF

References


T. Nomura, S.Hano, M.Aida, Isoprenoid-Substituted Flavonoid from Artocarpus Plants (Moraceae), Heterocycles, 47, 1179-1205 (1998).

B.N. Su, M.Cuendet, M.E. Hawthorne, L.B.S.Kardono, S.Riswan, H.H.S. Fong, R.G. Mehta, J.M.Pezzuto, A.D. Kinghorn, Constituents of the bark and twigs of Artocarpus dadah with cyclooxygenase inhibitory activity, J. Nat. Prod., 65, 163 –169 (2002).

A.R. Han , Y.J. Kang, T. Wibowo, S.K. Lee, E.K. Seo, Prenylated flavonoids from the heartwood of Artocarpus communis with inhibitory activity on lipopolysaccharide induced nitric oxide production, J. Nat. Prod.,69, 719-721 (2006).

Y. Ren, L.B.S. Kardono, S. Riswwan, H. Chai, N.R. Farnsworth, D.D. Soerjarto, E.J. de Blanco, A.D. Kinghorn, Cytotoxic and NF-κB inhibitory constituents of Artocarpus rigida, J. Nat. Prod., 75, 949-955 (2010).

M.T.T. Nguyen, T.H. Le, H.X. Nguyen, P.H. Dang, T.N.V. Do, M. Abe, R. Takagi, N.T. Nguyen, Artocarmins G-M, Prenylated 4-Chromenones from the Stems of Artocarpusrigida and Their Tyrosinase Inhibitory Activities, J. Nat. Prod., 80, 3172-3178 (2017)

T. Suhartati, A. Wulandari, J.F. Suwandi, Yandri, S. Hadi, Artonin O, a Xanthone Compound from Root Wood of Artocarpus rigida, Orient. J. Chem., 32 (5), 2777-2784, (2016).

T. Suhartati, Yandri, S. Hadi, The Bioactivity Test of Artonin E from the Bark of Artocarpus rigida Blume, Eur. J. Sci. Res., 23, 330 – 337 (2008).

T. Suhartati, Yandri, J.F Suwandi, S. Hadi, In vitro and in vivo antiplasmodial activity of oxyresveratrol and artonin E isolated frm two Artocarpus plants in Indonesia,. Orient. J. Chem., 26 (3), 825 – 830 (2010).

Y. Hano, Y. Yamagami,M. Kobayashi, R. Isohata, T. Nomura,Artonins E and F, Two New Prenylflavones From The Bark of Artocarpus communis Forst, Heterocycles, 31, 877 – 882 (1990).

T. Suhartati,S.A. Achmad, N. Aimi, E.H. Hakim, M. Kitajima, H. Takayama, K. Takeya,.Artoindonesianin L, a new prenylated flavone with cytotoxicity activity from Artocarpus rotunda, Fitoterapia, 72, 912-918 (2001).

S. Boonphong, A. Baramee, P. Kittakoop, and P. Puangsombat, Antitubercular and Antiplasmodial prenylated flavones from the roots of Artocarpus altilis, Chiang Mai J. Sci., 34(3), 339-344 (2007).

I. Etti, R. Abdullah, N. M. Hashim, A. Kadir, A. B. Abdul, C. Etti, I. Malami, P. Waziri and C. Wun, How Artonin E and Structural Analogs from Artocarpus Species Abrogates Estrogen Receptor Signaling in Breast Cancer, Molecules, 21(7), 839 – 856 (2016).

M.C Alley, D.A. Scudiero, A. Monks, M.L. Hursey, M.J. Czerwinski, D.L. Fine, B.J. Abbott, J.G. Mayo, R.H. Shoemaker, M.R. Boyd,Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay,Cancer Res., 48, 589-601 (1988).

E. Breitmaier, Structure Elucidation by NMR In Organic Chemistry. A Practical Guide. Third Revised Edition. John Wiley & Sons Ltd. England, 2002. 258 p.

F.A. Settle, Handbook of Instrumental Techniques for Analytical Chemistry. Prentice-Hall, Inc. New Jersey. 1997. p. 25-30; 247-252; 309-311; 481-485.

T.J. Mabry, K.R Markham, M.B. Thomas, The Systematic Identification of Flavonoid. Spinger-Verlag, New York. 1970. p. 3-56, 165-171.




DOI: http://dx.doi.org/10.20450/mjcce.2018.1406

Refbacks

  • There are currently no refbacks.


Bookmark and Share


Copyright (c) 2018 Sutopo Hadi, Tati Suhartati, Hernawan Hernawan, Jhons F. Suwandi, Yandri Yandri

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