Chemical Constituents of Goniothalamus elegans Leaves and their Anticancer Activity

Jirawan Noichan; Thanaset Senawong; Sarawut Tontapha; Vitttaya Amornkitbumrung; Natcha P. Suchaichit; Panawan Moosophon

doi:10.14233/ajchem.2024.30575

Issue

Vol. 36 No. 1 (2024): Vol 36 Issue 1, 2024

Issue Published : December 31, 2023

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

Chemical Constituents of Goniothalamus elegans Leaves and their Anticancer Activity

https://doi.org/10.14233/ajchem.2024.30575

Jirawan Noichan

Natural Products Research Unit, Center of Excellence for Innovation in Chemistry, Department of Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002, Thailand

https://orcid.org/0009-0003-6645-4638

Thanaset Senawong

Department of Biochemistry, Khon Kaen University, Khon Kaen 40002, Thailand

https://orcid.org/0000-0001-8788-5291

Sarawut Tontapha

Integrated Nanotechnology Research Centre, Department of Physics, Faculty of Science, Khon Kaen University, Khon Kaen, 40002, Thailand

https://orcid.org/0000-0002-8648-2375

Vitttaya Amornkitbumrung

Integrated Nanotechnology Research Centre, Department of Physics, Faculty of Science, Khon Kaen University, Khon Kaen, 40002, Thailand

Natcha P. Suchaichit

Department of Applied Chemistry, Faculty of Science and Liberal Arts, Rajamangala University of Technology Isan, Nakhon Ratchasima, 30000, Thailand

https://orcid.org/0000-0001-7725-2626

Panawan Moosophon

Natural Products Research Unit, Center of Excellence for Innovation in Chemistry, Department of Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002, Thailand

https://orcid.org/0000-0002-3565-1597

Corresponding Author(s) : Panawan Moosophon

mpanaw@kku.ac.th

Asian Journal of Chemistry, Vol. 36 No. 1 (2024): Vol 36 Issue 1, 2024
Article Published : December 31, 2023

Abstract

The methanol extract from the Goniothalamus elegans leaves showed potent antiproliferative effect on human cancer cells. After purification, goniothalamin (1), goniomicin C (2), pinocembirn (3), stigmasterol (4), trans-cinnamic acid (5), and benzoic acid (6) were isolated from the extract. Their structures were elucidated by spectroscopic analysis and comparison with literature data. The antiproliferative activity of compounds on cancer cell lines were determined by MMT assay and found that 1 displayed strong cytotoxicity towards human colon (HCT116), cervical (HeLa), and breast (MCF-7) cancer cells (IC₅₀ 0.35-2.36 µg/mL). The extract and compound 1 showed stronger inhibitory effect on three cancer cells than standard drug cisplatin, while, their antiproliferation on non-cancer cells showed close. Moreover, compound 2 showed cytotoxicity to MCF-7 cells without showing cytotoxicity against non-cancer cells. These results reveal that the extract and compound 2 are potent human cancer cells proliferation and needed further investigations the mechanism as chemotherapeutic agents.

Keywords

Goniothalamus elegans goniomicin C goniothalamin anticancer

Noichan, J., Senawong, T., Tontapha, S., Amornkitbumrung, V., P. Suchaichit, N., & Moosophon, P. (2023). Chemical Constituents of Goniothalamus elegans Leaves and their Anticancer Activity. Asian Journal of Chemistry, 36(1), 104–108. https://doi.org/10.14233/ajchem.2024.30575

Download Citation

References

A.M. Alabsi, R. Ali, A.M. Ali, S.A.R. Al-Dubai, K. Ganasegeran, H. Harun, M.A. Alshagga, S.D. Salem and N.H.B.A. Kasim, Asian Pac. J. Cancer Prev., 14, 6273 (2013); https://doi.org/10.7314/APJCP.2013.14.11.6273
R.M.K. Saunders and P. Chalermglin, Bot. J. Linn. Soc., 156, 355 (2008); https://doi.org/10.1111/j.1095-8339.2007.00762.x
M.A. Seyed, I. Jantan and S.N.A. Bukhari, Biomed Res Int., 2014, 536508 (2014); https://doi.org/10.1155/2014/536508
X. Fang, J.E. Anderson, C. Chang, P.E. Fanwick and J.L. McLaughlin, J. Chem. Soc., Perkin Trans. 1, 1655 (1990); https://doi.org/10.1039/p19900001655
R. Kampong, W. Pompimon, P. Meepowpan, S. Sukdee, P. Sombutsiri, N. Nantasaen and S. Krachodnok, Int. J. Chem. Sci., 11, 1234 (2013).
R. Kim, V. Bihud, K. Bin-Mohamad, K. Leong, J. Bin-Mohamad, F. Bin-Ahmad, H. Hazni, N. Kasim, S. Halim and K. Awang, Molecules, 18, 128 (2012); https://doi.org/10.3390/molecules18010128
Y.-H. Lan, F.-R. Chang, J.-H. Yu, Y.-L. Yang, Y.-L. Chang, S.-J. Lee and Y.-C. Wu, J. Nat. Prod., 66, 487 (2003); https://doi.org/10.1021/np020441r
S. Omar, C.L. Chee, F. Ahmad, J.X. Ni, H. Jaber, J. Huang and T. Nakatsu, Phytochemistry, 31, 4395 (1992); https://doi.org/10.1016/0031-9422(92)80493-X
V. Seidel, F. Bailleul and P.G. Waterman, Phytochemistry, 55, 439 (2000); https://doi.org/10.1016/S0031-9422(00)00346-0
N. Soonthornchareonnon, K. Suwanborirux, R. Bavovada, C. Patarapanich and J.M. Cassady, J. Nat. Prod., 62, 1390 (1999); https://doi.org/10.1021/np990197c
A. de Fátima, L.V. Modolo, L.S. Conegero, R.A. Pilli, C.V. Ferreira, L.K. Kohn and J.E. de Carvalho, Curr. Med. Chem., 13, 3371 (2006); https://doi.org/10.2174/092986706779010298
N. Suchaichit, K. Kanokmedhakul, N. Panthama, K. Poopasit, P. Moosophon and S. Kanokmedhakul, Fitoterapia, 103, 206 (2015); https://doi.org/10.1016/j.fitote.2015.04.005
T. Senawong, S. Misuna, S. Nuchadomrong, P. Sawatsitang, C. Phaosiri, S. Khaopha, A. Surapaitoon and B. Sripa, BMC Complement. Altern. Med., 13, 232 (2013); https://doi.org/10.1186/1472-6882-13-232
D. Hughes and ý H. Mehmet, Cell Proliferation and Apoptosis, BIOS Scientific Publishers, Oxford (2003).
J. Pospíšil and I.E. Markó, Tetrahedron Lett., 47, 5933 (2006); https://doi.org/10.1016/j.tetlet.2006.06.054
R.-H. Liu, X.-C. Wen, F. Shao, P.-Z. Zhang, H.-L. Huang and S. Zhang, Chin. Herb. Med., 8, 89 (2016); https://doi.org/10.1016/S1674-6384(16)60014-X
P. Forgo and K.E. Kövér, Steroids, 69, 43 (2004); https://doi.org/10.1016/j.steroids.2003.09.012
T. Fukuyama, M. Arai, H. Matsubara and I. Ryu, J. Org. Chem., 69, 8105 (2004); https://doi.org/10.1021/jo049028+
L.-Q. Cui, K. Liu and C. Zhang, Org. Biomol. Chem., 9, 2258 (2011); https://doi.org/10.1039/c0ob00722f
A. Terakita, H. Matsunaga, T. Ueda, T. Eguchi, M. Echigoya, K. Umemoto and M. Godo, Chem. Pharm. Bull., 52, 546 (2004); https://doi.org/10.1248/cpb.52.546

References

A.M. Alabsi, R. Ali, A.M. Ali, S.A.R. Al-Dubai, K. Ganasegeran, H. Harun, M.A. Alshagga, S.D. Salem and N.H.B.A. Kasim, Asian Pac. J. Cancer Prev., 14, 6273 (2013); https://doi.org/10.7314/APJCP.2013.14.11.6273

R.M.K. Saunders and P. Chalermglin, Bot. J. Linn. Soc., 156, 355 (2008); https://doi.org/10.1111/j.1095-8339.2007.00762.x

M.A. Seyed, I. Jantan and S.N.A. Bukhari, Biomed Res Int., 2014, 536508 (2014); https://doi.org/10.1155/2014/536508

X. Fang, J.E. Anderson, C. Chang, P.E. Fanwick and J.L. McLaughlin, J. Chem. Soc., Perkin Trans. 1, 1655 (1990); https://doi.org/10.1039/p19900001655

R. Kampong, W. Pompimon, P. Meepowpan, S. Sukdee, P. Sombutsiri, N. Nantasaen and S. Krachodnok, Int. J. Chem. Sci., 11, 1234 (2013).

R. Kim, V. Bihud, K. Bin-Mohamad, K. Leong, J. Bin-Mohamad, F. Bin-Ahmad, H. Hazni, N. Kasim, S. Halim and K. Awang, Molecules, 18, 128 (2012); https://doi.org/10.3390/molecules18010128

Y.-H. Lan, F.-R. Chang, J.-H. Yu, Y.-L. Yang, Y.-L. Chang, S.-J. Lee and Y.-C. Wu, J. Nat. Prod., 66, 487 (2003); https://doi.org/10.1021/np020441r

S. Omar, C.L. Chee, F. Ahmad, J.X. Ni, H. Jaber, J. Huang and T. Nakatsu, Phytochemistry, 31, 4395 (1992); https://doi.org/10.1016/0031-9422(92)80493-X

V. Seidel, F. Bailleul and P.G. Waterman, Phytochemistry, 55, 439 (2000); https://doi.org/10.1016/S0031-9422(00)00346-0

N. Soonthornchareonnon, K. Suwanborirux, R. Bavovada, C. Patarapanich and J.M. Cassady, J. Nat. Prod., 62, 1390 (1999); https://doi.org/10.1021/np990197c

A. de Fátima, L.V. Modolo, L.S. Conegero, R.A. Pilli, C.V. Ferreira, L.K. Kohn and J.E. de Carvalho, Curr. Med. Chem., 13, 3371 (2006); https://doi.org/10.2174/092986706779010298

N. Suchaichit, K. Kanokmedhakul, N. Panthama, K. Poopasit, P. Moosophon and S. Kanokmedhakul, Fitoterapia, 103, 206 (2015); https://doi.org/10.1016/j.fitote.2015.04.005

T. Senawong, S. Misuna, S. Nuchadomrong, P. Sawatsitang, C. Phaosiri, S. Khaopha, A. Surapaitoon and B. Sripa, BMC Complement. Altern. Med., 13, 232 (2013); https://doi.org/10.1186/1472-6882-13-232

D. Hughes and ý H. Mehmet, Cell Proliferation and Apoptosis, BIOS Scientific Publishers, Oxford (2003).

J. Pospíšil and I.E. Markó, Tetrahedron Lett., 47, 5933 (2006); https://doi.org/10.1016/j.tetlet.2006.06.054

R.-H. Liu, X.-C. Wen, F. Shao, P.-Z. Zhang, H.-L. Huang and S. Zhang, Chin. Herb. Med., 8, 89 (2016); https://doi.org/10.1016/S1674-6384(16)60014-X

P. Forgo and K.E. Kövér, Steroids, 69, 43 (2004); https://doi.org/10.1016/j.steroids.2003.09.012

T. Fukuyama, M. Arai, H. Matsubara and I. Ryu, J. Org. Chem., 69, 8105 (2004); https://doi.org/10.1021/jo049028+

L.-Q. Cui, K. Liu and C. Zhang, Org. Biomol. Chem., 9, 2258 (2011); https://doi.org/10.1039/c0ob00722f

A. Terakita, H. Matsunaga, T. Ueda, T. Eguchi, M. Echigoya, K. Umemoto and M. Godo, Chem. Pharm. Bull., 52, 546 (2004); https://doi.org/10.1248/cpb.52.546

Issue

Vol. 36 No. 1 (2024): Vol 36 Issue 1, 2024

Chemical Constituents of Goniothalamus elegans Leaves and their Anticancer Activity

Corresponding Author(s) : Panawan Moosophon

Abstract

Keywords

Full Article

Download Citation

References

Table Of Contents