Copyright (c) 2023 CHARISSE T. TUGAHAN
This work is licensed under a Creative Commons Attribution 4.0 International License.
Chemical Constituents of Macaranga grandifolia
Corresponding Author(s) : CHARISSE T. TUGAHAN
Asian Journal of Chemistry,
Vol. 35 No. 9 (2023): Vol 35 Issue 9, 2023
Abstract
The chemical analysis of dichloromethane (DCM) extract of Macaranga grandifolia (Blanco) Merr. resulted in the isolation and identification of several compounds. From the leaves, vedelianin (1), squalene (2), β-carotene (3) and polyprenol (4) were isolated. The barks contained a mixture of stigmasterol (5a) and β-sitosterol (5b). Additionally, the fruits yielded saturated fatty acid (6). The elucidation of structure 1 was accomplished through the utilization of comprehensive 1D and 2D NMR spectroscopic techniques. The identification of the structures of compounds 2-6 was achieved through a comparative analysis of their nuclear magnetic resonance (NMR) data with the literature data.
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- T. Péresse, G. Jézéquel, P.M. Allard, V.C. Pham, D.T. Huong, F. Blanchard, J. Bignon, H. Lévaique, J.-L. Wolfender, M. Litaudon and F. Roussi, J. Nat. Prod., 80, 2684 (2017); https://doi.org/10.1021/acs.jnatprod.7b00409
- P.A. Segun, O.O. Ogbole, F.M. Ismail, L. Nahar, A.R. Evans, E.O. Ajaiyeoba and S.D. Sarker, Fitoterapia, 134, 151 (2019); htps://doi.org/10.1016/j.fitote.2019.02.019
- J.M. Joseph, J. Med. Plants Res., 8, 489 (2014); https://doi.org/10.5897/JMPR2014.5396
- L.T.N. Vu, T.B. Ngan, L.T. Phuong, D.T.M. Huong, M. Litaudon, N. Van Hung, T.D. Thach and P. Van Cuong, Vietnam J. Chem., 56, 516 (2018); https://doi.org/10.1002/vjch.201800040
- L.T.N. Vu, L.T. Anh, N.T. Cuc, N.X. Nhiem, B.H. Tai, P. Van Kiem and P. Van Cuong, Nat. Prod. Res., 35, 2123 (2019); https://doi.org/10.1080/14786419.2019.1662007
- D.T.M. Huong, N.T. Linh, T.T.T. Van, M. Litaudon, F. Roussi, V. Van Nam and P. Van Cuong, Vietnam J. Chem., 58, 338 (2020); https://doi.org/10.1002/vjch.2019000182
- Binunga Macaranga tanarius (Linn.) Muell.-Arg. Downloaded from www.stuartxchange.org/Binunga.html
- Binuñgang-malapad Macaranga grandifolia (Blanco) Merr. Downloaded from www.stuartxchange.org/Binungang-malapad.html
- E. Marliana, R. Ruga, R. Hairani, T.S. Tjahjandarie and M. Tanjung, J. Phys. Conf. Ser., 1277, 012014 (2019); https://doi.org/10.1088/1742-6596/1277/1/012014
- E. Marliana, R. Hairani, T.S. Tjahjandarie and M. Tanjung, IOP Conf. Ser. Earth Environ. Sci., 144, 012011 (2018); https://doi.org/10.1088/1755-1315/144/1/012011
- T.M.H. Doan, T.L. Nguyen, T.T.V. Trinh, V.N. Vu, T.D. Phi, M. Litaudon and V.C. Pham, J. Anal. Methods Chem., 2019, 2917032 (2019); https://doi.org/10.1155/2019/2917032
- P. Hendra, O.A. Jamil, D.A. Maharani, M.A. Suhadi, C.Y. Putri and J.J. Fenty, Asian J. Pharm. Clin. Res., 10, 239 (2017).
- M.D. Suba, A.H. Arriola, and G.J. D. Alejandro, Biodiversitas, 20, 1034 (2019).
- V.D. Ebajo Jr., R. Brkljaèa, S. Urban and R.Y. Ragasa, J. Appl. Pharm. Sci., 5, 69 (2015); https://doi.org/10.7324/JAPS.2015.501111
- C.Y. Ragasa, M.P. Medecilo and C.C. Shen, Der Pharm. Chem., 7, 395 (2015).
- V.D. Ebajo Jr., C.C. Shen and C.Y. Ragasa, Res. J. Appl. Pharm. Sci., 5, 33 (2015).
- C.Y. Ragasa, O.B. Torres, J.M.P. Gutierrez, H.P.B.C. Kristiansen and C.C. Shen, J. Appl. Pharm. Sci., 5, 94 (2015); https://doi.org/10.7324/JAPS.2015.50416
- O. Thoison, E. Hnawia, F. Guiéritte-Voegelein and T. Sévenet, Phytochemistry, 31, 1439 (1992); https://doi.org/10.1016/0031-9422(92)80315-6
- B.J. Yoder, S. Cao, A. Norris, J.S. Miller, F. Ratovoson, J. Razafitsalama, R. Andriantsiferana, V.E. Rasamison and D.G.I. Kingston, J. Nat. Prod., 70, 342 (2007); https://doi.org/10.1021/np060484y
- J.A. Beutler, R.H. Shoemaker, T. Johnson and M.R. Boyd, J. Nat. Prod., 61, 1509 (1998); https://doi.org/10.1021/np980208m
- J.J. Topczewski and D.F. Wiemer, Tetrahedron Lett., 52, 1628 (2011); https://doi.org/10.1016/j.tetlet.2011.01.137
- Z.R. Huang, Y.K. Lin and J.Y. Fang, Molecules, 14, 540 (2009); https://doi.org/10.3390/molecules14010540
- F.E. Günes, J. Marmara Univ. Institute Health Sci., 3, 1 (2013); https://doi.org/10.5455/musbed.20131213100404
- J.M. Lou-Bonafonte, R. Martínez-Beamonte, T. Sanclemente, J.C. Surra, L.V. Herrera-Marcos, J. Sanchez-Marco, C. Arnal and J. Osada, Mol. Nutr. Food Res., 62, 1800136 (2018); https://doi.org/10.1002/mnfr.201800136
- R. Cioncada, M. Maddaluno, H.T.M. Vo, M. Woodruff, S. Tavarini, C. Sammicheli, M. Tortoli, A. Pezzicoli, E. De Gregorio, M.C. Carroll, U. D’Oro and D. Piccioli, PLoS One, 12, e0185843 (2017); https://doi.org/10.1371/journal.pone.0185843
- J.M.C. Cayme and C.Y. Ragasa, Kimika, 20, 5 (2004); https://doi.org/10.26534/kimika.v20i1.5-12
- L. Bogacz-Radomska and J. Harasym, Food Qual. Saf., 2, 69 (2018); https://doi.org/10.1093/fqsafe/fyy004
- R. Tao, C. Wang, J. Ye, H. Zhou and H. Chen, BioMed Res. Int., 2016, 4191938 (2016); https://doi.org/10.1155/2016/4191938
- I. Vanaga, J. Gubernator, I. Nakurte, U. Kletnieks, R. Muceniece and B. Jansone, Molecules, 25, 1801 (2020); https://doi.org/10.3390/molecules25081801
- J. Hu, P. Li and T. Zhang, Phytother. Res., 32, 1450 (2018); https://doi.org/10.1002/ptr.6096
- X.X. Zhuang, X. Zang, G.Y. Zheng, N. Hua, Y. Sun, Y.H. Hu and L. He, Phytotherapy Res., 32, 1098 (2018).
- L. Yang, C. Wang, J. Ye and H. Li, Fitoterapia, 82, 834 (2011); https://doi.org/10.1016/j.fitote.2011.04.009
- H. Yuan, H. Shen, Y. Yan, C. Zhang and C. Wang, Chem. Ind. Forest Prod., 42, 5 (2022).
- H. Yuan, C. Zhang, P. Zhou, X. Yang, R. Tao, J. Ye and C. Wang, Arab. J. Chem., 16, 104679 (2023); https://doi.org/10.1016/j.arabjc.2023.104679
- M.M. Mailafiya, A.J. Yusuf, M.I. Abdullahi, G.A. Aleku, I.A. Ibrahim, M. Yahaya and C.O. Alebiosu, J. Med. Plants Econ. Dev., 2, 1 (2018); https://hdl.handle.net/10520/EJC-df2f206df
- N. Kaur, J. Chaudhary, A. Jain and L. Kishore, Int. J. Pharm. Sci. Res., 2, 2259 (2011).
- K. Rashed, J. Sci. Innov. Technol, 9, 208 (2020).
- A.A. Baskar, S. Ignacimuthu, G.M. Paulraj and K.S. Al Numair, BMC Complement. Altern. Med., 10, 24 (2010); https://doi.org/10.1186/1472-6882-10-24
- A.A. Baskar, K.S. Al Numair, M. Gabriel Paulraj, M.A. Alsaif, M.A. Muamar and S. Ignacimuthu, J. Med. Food, 15, 335 (2012); https://doi.org/10.1089/jmf.2011.1780
References
T. Péresse, G. Jézéquel, P.M. Allard, V.C. Pham, D.T. Huong, F. Blanchard, J. Bignon, H. Lévaique, J.-L. Wolfender, M. Litaudon and F. Roussi, J. Nat. Prod., 80, 2684 (2017); https://doi.org/10.1021/acs.jnatprod.7b00409
P.A. Segun, O.O. Ogbole, F.M. Ismail, L. Nahar, A.R. Evans, E.O. Ajaiyeoba and S.D. Sarker, Fitoterapia, 134, 151 (2019); htps://doi.org/10.1016/j.fitote.2019.02.019
J.M. Joseph, J. Med. Plants Res., 8, 489 (2014); https://doi.org/10.5897/JMPR2014.5396
L.T.N. Vu, T.B. Ngan, L.T. Phuong, D.T.M. Huong, M. Litaudon, N. Van Hung, T.D. Thach and P. Van Cuong, Vietnam J. Chem., 56, 516 (2018); https://doi.org/10.1002/vjch.201800040
L.T.N. Vu, L.T. Anh, N.T. Cuc, N.X. Nhiem, B.H. Tai, P. Van Kiem and P. Van Cuong, Nat. Prod. Res., 35, 2123 (2019); https://doi.org/10.1080/14786419.2019.1662007
D.T.M. Huong, N.T. Linh, T.T.T. Van, M. Litaudon, F. Roussi, V. Van Nam and P. Van Cuong, Vietnam J. Chem., 58, 338 (2020); https://doi.org/10.1002/vjch.2019000182
Binunga Macaranga tanarius (Linn.) Muell.-Arg. Downloaded from www.stuartxchange.org/Binunga.html
Binuñgang-malapad Macaranga grandifolia (Blanco) Merr. Downloaded from www.stuartxchange.org/Binungang-malapad.html
E. Marliana, R. Ruga, R. Hairani, T.S. Tjahjandarie and M. Tanjung, J. Phys. Conf. Ser., 1277, 012014 (2019); https://doi.org/10.1088/1742-6596/1277/1/012014
E. Marliana, R. Hairani, T.S. Tjahjandarie and M. Tanjung, IOP Conf. Ser. Earth Environ. Sci., 144, 012011 (2018); https://doi.org/10.1088/1755-1315/144/1/012011
T.M.H. Doan, T.L. Nguyen, T.T.V. Trinh, V.N. Vu, T.D. Phi, M. Litaudon and V.C. Pham, J. Anal. Methods Chem., 2019, 2917032 (2019); https://doi.org/10.1155/2019/2917032
P. Hendra, O.A. Jamil, D.A. Maharani, M.A. Suhadi, C.Y. Putri and J.J. Fenty, Asian J. Pharm. Clin. Res., 10, 239 (2017).
M.D. Suba, A.H. Arriola, and G.J. D. Alejandro, Biodiversitas, 20, 1034 (2019).
V.D. Ebajo Jr., R. Brkljaèa, S. Urban and R.Y. Ragasa, J. Appl. Pharm. Sci., 5, 69 (2015); https://doi.org/10.7324/JAPS.2015.501111
C.Y. Ragasa, M.P. Medecilo and C.C. Shen, Der Pharm. Chem., 7, 395 (2015).
V.D. Ebajo Jr., C.C. Shen and C.Y. Ragasa, Res. J. Appl. Pharm. Sci., 5, 33 (2015).
C.Y. Ragasa, O.B. Torres, J.M.P. Gutierrez, H.P.B.C. Kristiansen and C.C. Shen, J. Appl. Pharm. Sci., 5, 94 (2015); https://doi.org/10.7324/JAPS.2015.50416
O. Thoison, E. Hnawia, F. Guiéritte-Voegelein and T. Sévenet, Phytochemistry, 31, 1439 (1992); https://doi.org/10.1016/0031-9422(92)80315-6
B.J. Yoder, S. Cao, A. Norris, J.S. Miller, F. Ratovoson, J. Razafitsalama, R. Andriantsiferana, V.E. Rasamison and D.G.I. Kingston, J. Nat. Prod., 70, 342 (2007); https://doi.org/10.1021/np060484y
J.A. Beutler, R.H. Shoemaker, T. Johnson and M.R. Boyd, J. Nat. Prod., 61, 1509 (1998); https://doi.org/10.1021/np980208m
J.J. Topczewski and D.F. Wiemer, Tetrahedron Lett., 52, 1628 (2011); https://doi.org/10.1016/j.tetlet.2011.01.137
Z.R. Huang, Y.K. Lin and J.Y. Fang, Molecules, 14, 540 (2009); https://doi.org/10.3390/molecules14010540
F.E. Günes, J. Marmara Univ. Institute Health Sci., 3, 1 (2013); https://doi.org/10.5455/musbed.20131213100404
J.M. Lou-Bonafonte, R. Martínez-Beamonte, T. Sanclemente, J.C. Surra, L.V. Herrera-Marcos, J. Sanchez-Marco, C. Arnal and J. Osada, Mol. Nutr. Food Res., 62, 1800136 (2018); https://doi.org/10.1002/mnfr.201800136
R. Cioncada, M. Maddaluno, H.T.M. Vo, M. Woodruff, S. Tavarini, C. Sammicheli, M. Tortoli, A. Pezzicoli, E. De Gregorio, M.C. Carroll, U. D’Oro and D. Piccioli, PLoS One, 12, e0185843 (2017); https://doi.org/10.1371/journal.pone.0185843
J.M.C. Cayme and C.Y. Ragasa, Kimika, 20, 5 (2004); https://doi.org/10.26534/kimika.v20i1.5-12
L. Bogacz-Radomska and J. Harasym, Food Qual. Saf., 2, 69 (2018); https://doi.org/10.1093/fqsafe/fyy004
R. Tao, C. Wang, J. Ye, H. Zhou and H. Chen, BioMed Res. Int., 2016, 4191938 (2016); https://doi.org/10.1155/2016/4191938
I. Vanaga, J. Gubernator, I. Nakurte, U. Kletnieks, R. Muceniece and B. Jansone, Molecules, 25, 1801 (2020); https://doi.org/10.3390/molecules25081801
J. Hu, P. Li and T. Zhang, Phytother. Res., 32, 1450 (2018); https://doi.org/10.1002/ptr.6096
X.X. Zhuang, X. Zang, G.Y. Zheng, N. Hua, Y. Sun, Y.H. Hu and L. He, Phytotherapy Res., 32, 1098 (2018).
L. Yang, C. Wang, J. Ye and H. Li, Fitoterapia, 82, 834 (2011); https://doi.org/10.1016/j.fitote.2011.04.009
H. Yuan, H. Shen, Y. Yan, C. Zhang and C. Wang, Chem. Ind. Forest Prod., 42, 5 (2022).
H. Yuan, C. Zhang, P. Zhou, X. Yang, R. Tao, J. Ye and C. Wang, Arab. J. Chem., 16, 104679 (2023); https://doi.org/10.1016/j.arabjc.2023.104679
M.M. Mailafiya, A.J. Yusuf, M.I. Abdullahi, G.A. Aleku, I.A. Ibrahim, M. Yahaya and C.O. Alebiosu, J. Med. Plants Econ. Dev., 2, 1 (2018); https://hdl.handle.net/10520/EJC-df2f206df
N. Kaur, J. Chaudhary, A. Jain and L. Kishore, Int. J. Pharm. Sci. Res., 2, 2259 (2011).
K. Rashed, J. Sci. Innov. Technol, 9, 208 (2020).
A.A. Baskar, S. Ignacimuthu, G.M. Paulraj and K.S. Al Numair, BMC Complement. Altern. Med., 10, 24 (2010); https://doi.org/10.1186/1472-6882-10-24
A.A. Baskar, K.S. Al Numair, M. Gabriel Paulraj, M.A. Alsaif, M.A. Muamar and S. Ignacimuthu, J. Med. Food, 15, 335 (2012); https://doi.org/10.1089/jmf.2011.1780