Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Phytochemical Constituents of Annona reticulata and their Cytotoxic Activity

Author(s): Ty Viet Pham, Thang Quoc Le , Anh Tuan Le , Hung Quoc Vo and Duc Viet Ho*

Volume 17, Issue 3, 2020

Page: [206 - 210] Pages: 5

DOI: 10.2174/1570178616666190724123004

Price: $65

Abstract

A phytochemical investigation of the leaves of Annona reticulata led to the isolation and structural determination of β-sitosterol (1), ent-pimara-8(14),15-dien-19-oic acid (2), ent-pimara- 8(14),15-dien-19-ol (3), quercetin (4), quercetin 3-O-α-L-arabinopyranoside (5), and a mixture of quercetin 3-O-β-D-galactopyranoside (6a) and quercetin 3-O-β-D-glucopyranoside (6b). Of these, compounds 2 and 3 were isolated from the genus Annona for the first time. Compound 3 showed strong cytotoxicity against SK-LU-1 and SW626 cell lines with IC50 values of 17.64 ± 1.07 and 19.79 ± 1.41 μg mL-1, respectively.

Keywords: Annona reticulata, Annonaceae, pimarane-type diterpene, flavonoid, cytotoxicity, SK-LU-1, SW626.

« Previous Next »
Graphical Abstract

[1]
World Health Organization - PRESS RELEASE, 2018. N° 263..
[2]
Forman, D.; Ferlay, J. World Cancer Report, 2014, 2014, 16-53.
[3]
Thomford, N.E.; Senthebane, D.A.; Rowe, A.; Munro, D.; Seele, P.; Maroyi, A.; Dzobo, K. Int. J. Mol. Sci., 2018, 19, 1578.
[http://dx.doi.org/10.3390/ijms19061578]
[4]
Saad, J.M.; Hui, Y.H.; Rupprecht, J.K.; Anderson, J.E.; Kozlowski, J.F.; Zhao, G-X.; Wood, K.V.; McLaughlin, J.L. Tetrahedron, 1991, 47, 2751-2756.
[http://dx.doi.org/10.1016/S0040-4020(01)87082-4]
[5]
Chavan, S.S.; Shamkuwar, P.B.; Damale, M.G.; Pawar, D.P. Int. J. Pharm. Sci. Res., 2014, 5, 45-50.
[6]
Jamkhande, P.G.; Wattamwar, A.S. J. Tradit. Complement. Med., 2015, 5(3), 144-152.
[http://dx.doi.org/10.1016/j.jtcme.2015.04.001] [PMID: 26151026]
[7]
Quílez, A.M.; Fernández-Arche, M.A.; García-Giménez, M.D.; De la Puerta, R. J. Ethnopharmacol., 2018, 225, 244-270.
[http://dx.doi.org/10.1016/j.jep.2018.06.014] [PMID: 29933016]
[8]
Tam, V.T.; Hieu, B.C.; Chappe, B. Planta Med., 1993, 59(6), 576-576.
[http://dx.doi.org/10.1055/s-2006-959771] [PMID: 17230372]
[9]
Tam, V.T.; Chi Hieu, P.Q.; Chappe, B.; Roblot, F.; Laprévote, O.; Figadere, B.; Cavé, A. Nat. Prod. Lett., 1994, 4, 255-262.
[http://dx.doi.org/10.1080/10575639408043915]
[10]
Thang, T.D.; Kuo, P.C.; Huang, G.J.; Hung, N.H.; Huang, B.S.; Yang, M.L.; Luong, N.X.; Wu, T.S. Molecules, 2013, 18(4), 4477-4486.
[http://dx.doi.org/10.3390/molecules18044477] [PMID: 23591927]
[11]
Kovganko, N.V.; Kashkan, Z.N.; Borisov, E.V.; Batura, E.V. Chem. Nat. Compd., 1999, 35, 646-649.
[http://dx.doi.org/10.1007/BF02236293]
[12]
Kang, O.H.; Chae, H.S.; Choi, J.G.; Oh, Y.C.; Lee, Y.S.; Kim, J.H.; Seung, M.J.; Jang, H.J.; Bae, K.H.; Lee, J.H.; Shin, D.W.; Kwon, D.Y. Eur. J. Pharmacol., 2008, 601(1-3), 179-185.
[http://dx.doi.org/10.1016/j.ejphar.2008.10.012] [PMID: 18938152]
[13]
Matsuo, A.; Uto, S.; Nakayama, M.; Hayashi, S.; Yamasaki, K.; Kasai, R.; Tanaka, O. Tetrahedron Lett., 1976, 17, 2451-2454.
[http://dx.doi.org/10.1016/0040-4039(76)90017-4]
[14]
Liu, H.; Mou, Y.; Zhao, J.; Wang, J.; Zhou, L.; Wang, M.; Wang, D.; Han, J.; Yu, Z.; Yang, F. Molecules, 2010, 15(11), 7933-7945.
[http://dx.doi.org/10.3390/molecules15117933] [PMID: 21060300]
[15]
Fraisse, D.; Heitz, A.; Carnat, A.; Carnat, A.P.; Lamaison, J.L. Fitoterapia, 2000, 71(4), 463-464.
[http://dx.doi.org/10.1016/S0367-326X(00)00145-3] [PMID: 10925029]
[16]
Pereira, C.; Kuster, C.B.B.J.R.M.; Simas, N.K.; Sakuragui, C.M.; Wessjohann, A.P.L. Quim. Nova, 2012, 35, 1123-1126.
[http://dx.doi.org/10.1590/S0100-40422012000600010]
[17]
Jeong, S.I.; Han, W.S.; Yun, Y.H. Phytother. Res., 2006, 20, 511-514.
[http://dx.doi.org/10.1002/ptr.1894] [PMID: 16619343]
[18]
Sharma, E.; Arora, B.S.; Khajuria, A.; Sidiq, T.; Kishore, D.; Vishwakarma, R.A. IJPSR, 2011, 2, 2183-2189.
[19]
Aponte, J.C.; Jin, Z.; Vaisberg, A.J.; Castillo, D.; Málaga, E.; Leis, W.H.; Sauvain, M.; Gilman, R.H.; Hammond, G.B. Planta Med., 2011, 77(14), 1597-1599.
[http://dx.doi.org/10.1055/s-0030-1270960] [PMID: 21472652]
[20]
Meragelman, T.L.; Silva, G.L.; Mongelli, E.; Gil, R.R. Phytochemistry, 2003, 62(4), 569-572.
[http://dx.doi.org/10.1016/S0031-9422(02)00611-8] [PMID: 12560027]
[21]
Monks, A.; Scudiero, D.; Skehan, P.; Shoemaker, R.; Paull, K.; Vistica, D.; Hose, C.; Langley, J.; Cronise, P.; Vaigro-Wolff, A.; Gray-Goodrich, M.; Campbell, H.; Mayo, J.; Boyd, M. J. Natl. Cancer Inst., 1991, 83(11), 757-766.
[http://dx.doi.org/10.1093/jnci/83.11.757] [PMID: 2041050]
[22]
Ho, D.V.; Kodama, T.; Le, H.T.B.; Phan, K.V.; Do, T.T.; Bui, T.H.; Le, A.T.; Win, N.N.; Imagawa, H.; Ito, T.; Morita, H.; Nguyen, H.T. Bioorg. Med. Chem. Lett., 2015, 25(16), 3246-3250.
[http://dx.doi.org/10.1016/j.bmcl.2015.05.066] [PMID: 26077495]
[23]
Souiei, S.; Bousejra-Elgarah, F.; Belkacem, M.A.; Znati, M.; Bouajila, J.; Ben Jannet, H. Turk. J. Chem., 2018, 1-11.
[24]
Lee, I.S.; Jin, W.; Zhang, X.; Hung, T.M.; Song, K.S.; Seong, Y.H.; Bae, K. Arch. Pharm. Res., 2006, 29(7), 548-555.
[http://dx.doi.org/10.1007/BF02969263] [PMID: 16903073]
[25]
Seo, C.S.; Li, G.; Kim, C.H.; Lee, C.S.; Jahng, Y.; Chang, H.W.; Son, J.K. Arch. Pharm. Res., 2007, 30(11), 1404-1409.
[http://dx.doi.org/10.1007/BF02977364] [PMID: 18087808]
[26]
Arora, B.S.; Sharma, E.; Agrawal, S.K.; Agrawal, M. Indian J. Pharm. Sci., 2015, 77(6), 792-795.
[http://dx.doi.org/10.4103/0250-474X.174980] [PMID: 26997711]
[27]
Yang, C.T.; Hou, S.Q.; Tian, K.; Hu, Q.F.; Huang, X.Z.; Jiang, Z.Y. Helv. Chim. Acta, 2016, 99, 220-224.
[http://dx.doi.org/10.1002/hlca.201500221]
[28]
Kawaii, S.; Tomono, Y.; Katase, E.; Ogawa, K.; Yano, M. Biosci. Biotechnol. Biochem., 1999, 63(5), 896-899.
[http://dx.doi.org/10.1271/bbb.63.896] [PMID: 10380632]
[29]
Manthey, J.A.; Guthrie, N. J. Agric. Food Chem., 2002, 50(21), 5837-5843.
[http://dx.doi.org/10.1021/jf020121d] [PMID: 12358447]
[30]
Wang, Y.; Han, A.; Chen, E.; Singh, R.K.; Chichester, C.O.; Moore, R.G.; Singh, A.P.; Vorsa, N. Int. J. Oncol., 2015, 46(5), 1924-1934.
[http://dx.doi.org/10.3892/ijo.2015.2931] [PMID: 25776829]
[31]
Son, Y.O.; Lee, K.Y.; Kook, S.H.; Lee, J.C.; Kim, J.G.; Jeon, Y.M.; Jang, Y.S. Eur. J. Pharmacol., 2004, 502(3), 195-204.
[http://dx.doi.org/10.1016/j.ejphar.2004.09.012] [PMID: 15476745]

Rights & Permissions Print Cite
Article Metrics
20
© 2024 Bentham Science Publishers | Privacy Policy