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Letters in Organic Chemistry

Editor-in-Chief

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

Research Article

Cytotoxic Prenyl and Geranyl Coumarins from the Stem Bark of Casimiroa edulis

Author(s): Khun Nay Win Tun, Nanik Siti Aminah*, Alfinda Novi Kristanti, Rico Ramadhan and Yoshiaki Takaya

Volume 17, Issue 9, 2020

Page: [680 - 687] Pages: 8

DOI: 10.2174/1570178616666191019121437

Price: $65

Abstract

Phytochemical investigation of the methanolic extract of the stem bark of Casimiroa edulis afforded four coumarins. Various spectroscopic experiments were used to characterize the isolated coumarins. The structures were identified as auraptene (K-1), suberosin (K-2), 5-geranyloxypsoralen (bergamottin) (K-3), and 8-geranyloxypsoralen (K-4), based on the chemical and spectral analysis. Among these compounds, suberosin (K-2) and 5-geranyloxypsoralen (bergamottin) (K-3) were isolated for the first time from this genus, and auraptene (K-1) was isolated from this plant for the first time. Cytotoxicity of pure compound K-4 and sub-fraction MD-3 was evaluated against HeLa and T47D cell lines and moderate activity was found with an IC50 value in the range 17.4 to 72.33 μg/mL.

Keywords: Casimiroa edulis, coumarins, HeLa, spectroscopic experiments, stem bark, T47D.

Graphical Abstract

[1]
Khazir, J.; Riley, D.L.; Pilcher, L.A.; De-Maayer, P.; Mir, B.A. Nat. Prod. Commun., 2014, 9(11), 1655-1669.
[http://dx.doi.org/10.1177/1934578X1400901130] [PMID: 25532303]
[2]
Queiroz, E.F.; Alfattani, A.; Afzan, A.; Marcourt, L.; Guillarme, D.; Wolfender, J-L. J. Chromatogr. A, 2019, 1598, 85-91.
[http://dx.doi.org/10.1016/j.chroma.2019.03.042] [PMID: 30926257]
[3]
Xie, T.; Song, S.; Li, S.; Ouyang, L.; Xia, L.; Huang, J.; Huang, J. Cell Prolif., 2015, 48(4), 398-404.
[http://dx.doi.org/10.1111/cpr.12190] [PMID: 26009974]
[4]
Bucar, F.; Wube, A.; Schmid, M. Nat. Prod. Rep., 2013, 30(4), 525-545.
[http://dx.doi.org/10.1039/c3np20106f] [PMID: 23396532]
[5]
Munakata, R.; Inoue, T.; Koeduka, T.; Sasaki, K.; Tsurumaru, Y.; Sugiyama, A.; Uto, Y.; Hori, H.; Azuma, J.; Yazaki, K. Biosci. Biotechnol. Biochem., 2012, 76(7), 1389-1393.
[http://dx.doi.org/10.1271/bbb.120192] [PMID: 22785469]
[6]
Cho, J-Y.; Hwang, T-L.; Chang, T-H.; Lim, Y-P.; Sung, P-J.; Lee, T-H.; Chen, J-J. Food Chem., 2012, 135, 17-23.
[http://dx.doi.org/10.1016/j.foodchem.2012.04.025]
[7]
Erzincan, P.; Saçan, M.T.; Yüce-Dursun, B.; Danış, Ö.; Demir, S.; Erdem, S.S.; Ogan, A. SAR QSAR Environ. Res., 2015, 26(7-9), 721-737.
[http://dx.doi.org/10.1080/1062936X.2015.1088571] [PMID: 26470736]
[8]
Numonov, S.; Bobakulov, K.; Numonova, M.; Sharopov, F.; Setzer, W.N.; Khalilov, Q.; Begmatov, N.; Habasi, M.; Aisa, H.A. Nat. Prod. Res., 2018, 32(19), 2325-2332.
[http://dx.doi.org/10.1080/14786419.2017.1413558] [PMID: 29224384]
[9]
Tan, N.; Yazıcı-Tütünis, S.; Bilgin, M.; Tan, E.; Miski, M. Molecules, 2017, 22, 1098/1-1098/8.
[10]
Selim, Y.A.; Ouf, N.H. Org. Med. Chem. Lett., 2012, 2(1), 1-4.
[http://dx.doi.org/10.1186/2191-2858-2-1] [PMID: 22373472]
[11]
Golfakhrabadi, F.; Abdollahi, M.; Ardakani, M.R.S.; Saeidnia, S.; Akbarzadeh, T.; Ahmadabadi, A.N.; Ebrahimi, A.; Yousefbeyk, F.; Hassanzadeh, A.; Khanavi, M. Pharm. Biol., 2014, 52(10), 1335-1340.
[http://dx.doi.org/10.3109/13880209.2014.892140] [PMID: 25017518]
[12]
Feng, S.; Xu, L.; Wu, M.; Hao, J.; Qiu, S.X.; Wei, X. Fitoterapia, 2010, 81(6), 472-474.
[http://dx.doi.org/10.1016/j.fitote.2009.12.009] [PMID: 20060440]
[13]
Dreyer, D.L. J. Org. Chem., 1968, 33, 3577-3582.
[http://dx.doi.org/10.1021/jo01273a049]
[14]
Ito, A.; Shamon, L.A.; Yu, B.; Mata-Greenwood, E.; Lee, S.K.; Mehta, R.G.; Farnsworth, N.R.; Fong, H.H.S.; Pezzuto, J.M.; Kinghorn, A.D. J. Agric. Food Chem., 1998, 46, 3509-3516.
[http://dx.doi.org/10.1021/jf9802373]
[15]
Awaad, A.S.; Al-Jaber, N.A.; Soliman, G.A.; Al-Outhman, M.R.; Zain, M.E.; Moses, J.E.; El-Meligy, R.M. Phytother. Res., 2012, 26(3), 452-457.
[PMID: 22173732]
[16]
Nagai, H.; Tanaka, T.; Goto, T.; Kusudo, T.; Takahashi, N.; Kawada, T. Biosci. Biotechnol. Biochem., 2014, 78(2), 296-300.
[http://dx.doi.org/10.1080/09168451.2014.877821] [PMID: 25036684]
[17]
Heneka, B.; Rimpler, H.; Ankli, A.; Sticher, O.; Gibbons, S.; Heinrich, M. Phytochemistry, 2005, 66(6), 649-652.
[http://dx.doi.org/10.1016/j.phytochem.2004.12.005] [PMID: 15771884]
[18]
Bertin, R.; Chen, Z.; Martínez-Vázquez, M.; García-Argaéz, A.; Froldi, G. Phytomedicine, 2014, 21(5), 586-594.
[http://dx.doi.org/10.1016/j.phymed.2013.10.030] [PMID: 24309287]
[19]
Xu, Y.M.; Ramirez-Ahumada, M.C.; Valeriote, F.A.; Gunatilaka, L. Chin. J. Nat. Med., 2011, 9, 334-337.
[20]
Ubaldo-Suárez, D.; Estrada Reyes, R. De la Rosa - Sierra, R.; Martínez-Vázquez. M. Nat. Prod. Res., 2019, 33, 2526-2530.
[21]
Askari, M.; Sahebkar, A.; Iranshahi, M. Iran. J. Basic Med. Sci., 2009, 12, 63-69.
[22]
Siridechakorn, I.; Laphookhieo, S. Chem. Nat. Compd., 2012, 48, 308-309.
[http://dx.doi.org/10.1007/s10600-012-0231-3]
[23]
Dikpinar, T.; Süzgeç-Selçuk, S.; Çelik, B.Ö.; Uruşak, E.A. Ind. Crops Prod., 2018, 123, 762-767.
[http://dx.doi.org/10.1016/j.indcrop.2018.06.072]
[24]
Kawaii, S.; Tomono, Y.; Katase, E.; Ogawa, K.; Yano, M. J. Agric. Food Chem., 1999, 47(10), 4073-4078.
[http://dx.doi.org/10.1021/jf990155u] [PMID: 10552768]
[25]
Sandoval-Montemayor, N.E.; García, A.; Elizondo-Treviño, E.; Garza-González, E.; Alvarez, L.; del Rayo Camacho-Corona, M. Molecules, 2012, 17(9), 11173-11184.
[http://dx.doi.org/10.3390/molecules170911173] [PMID: 22992784]
[26]
Nam, V.D.; Teruhisa, F.; Hirofumi, T.; Hiroshi, K.; Nguyen, M.K.; Dung, L.V.; Ha, D.T.; Hiroshi, H. Nat. Prod. Sci., 2016, 22, 35-40.
[http://dx.doi.org/10.20307/nps.2016.22.1.35]
[27]
Anwar, C.; Prasetyo, Y.D.; Matsjeh, S.; Haryadi, W.; Sholikhah, E.N.; Nendrowati, N. Indones. J. Chem., 2018, 18, 102-107.
[http://dx.doi.org/10.22146/ijc.26864]
[28]
Venugopala, K.N.; Rashmi, V.; Odhav, B. Biomed. Res. Int, 2013, p. 963248, 14.
[29]
Lacy, A.; O’Kennedy, R. Curr. Pharm. Des., 2004, 10(30), 3797-3811.
[http://dx.doi.org/10.2174/1381612043382693] [PMID: 15579072]
[30]
Mishra, G.; Sachan, N.; Chawla, P. Lett. Org. Chem., 2015, 12, 429-455.
[http://dx.doi.org/10.2174/1570178612666150424235603]
[31]
Pinto, D.C.G.A.; Silva, A.M.S. Curr. Top. Med. Chem., 2017, 17(29), 3190-3198.
[PMID: 29243581]
[32]
Wang, X-B.; Li, G-H.; Li, L.; Zheng, L-J.; Huang, R.; Zhang, K-Q. Nat. Prod. Res., 2008, 22(8), 666-671.
[http://dx.doi.org/10.1080/14786410701766463] [PMID: 18569707]
[33]
Razavi, S.M.; Zahri, S.; Nazemiyeh, H.; Zarrini, G.; Mohammadi, S.; Abolghassemi-Fakhri, M-A. Nat. Prod. Res., 2009, 23(16), 1522-1527.
[http://dx.doi.org/10.1080/14786410802691909] [PMID: 19844826]
[34]
Almahy, H.A.; Alagimi, A.A. Arab. J. Chem., 2012, 5, 241-244.
[http://dx.doi.org/10.1016/j.arabjc.2011.03.019]
[35]
Nakamura, M.; Suzuki, T.; Takagi, M.; Tamura, H.; Masuda, T. Nat. Prod. Commun., 2014, 9(10), 1491-1494.
[http://dx.doi.org/10.1177/1934578X1400901021] [PMID: 25522543]
[36]
Iranshahi, M.; Kalategi, F.; Rezaee, R.; Shahverdi, A.R.; Ito, C.; Furukawa, H.; Tokuda, H.; Itoigawa, M. Planta Med., 2008, 74(2), 147-150.
[http://dx.doi.org/10.1055/s-2008-1034293] [PMID: 18240102]
[37]
Razavi, S.M.; Imanzadeh, G.; Davari, M. Eurasia. J. Biosci., 2010, 4, 17-22.
[38]
Curini, M.; Cravotto, G.; Epifano, F.; Giannone, G. Curr. Med. Chem., 2006, 13(2), 199-222.
[http://dx.doi.org/10.2174/092986706775197890] [PMID: 16472213]
[39]
Liu, Y.; Ren, C.; Cao, Y.; Wang, Y.; Duan, W.; Xie, L.; Sun, C.; Li, X. Molecules, 2017, 22, 1227/1-1227/13.
[40]
Figueroa, M.; Rivero-Cruz, I.; Rivero-Cruz, B.; Bye, R.; Navarrete, A.; Mata, R. J. Ethnopharmacol., 2007, 113(1), 125-131.
[http://dx.doi.org/10.1016/j.jep.2007.05.015] [PMID: 17582715]
[41]
Golfakhrabadi, F.; Abdollahi, M.; Ardakani, M.R.S.; Saeidnia, S.; Akbarzadeh, T.; Ahmadabadi, A.N.; Ebrahimi, A.; Yousefbeyk, F.; Hassanzadeh, A.; Khanavi, M. Pharm. Biol., 2014, 52(10), 1335-1340.
[http://dx.doi.org/10.3109/13880209.2014.892140] [PMID: 25017518]
[42]
Karakaya, S.; Gözcü, S.; Güvenalp, Z.; Özbek, H.; Yuca, H.; Dursunoğlu, B.; Kazaz, C.; Kılıç, C.S. Pharm. Biol., 2018, 56(1), 18-24.
[http://dx.doi.org/10.1080/13880209.2017.1414857] [PMID: 29233045]
[43]
Tavakoli, S.; Delnavazi, M-R.; Hadjiaghaee, R.; Jafari-Nodooshan, S.; Khalighi-Sigaroodi, F.; Akhbari, M.; Hadjiakhoondi, A.; Yassa, N. Nat. Prod. Res., 2018, 32(22), 2724-2728.
[http://dx.doi.org/10.1080/14786419.2017.1375915] [PMID: 28954543]

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