Login Register Cart 0
Generic placeholder image

Mini-Reviews in Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1389-5575
ISSN (Online): 1875-5607

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

A Review on Classification and Biological Activities of Alkaloids from the Genus Zanthoxylum Species

Author(s): Wen-Jun Wei, Xiao-Hui Chen, Tao Guo*, Xiao-Qian Liu*, Yi Zhao, Li-Li Wang, Jin-Xu Lan, Han-Wei Li, Yan-Po Si and Zhi-Min Wang

Volume 21, Issue 3, 2021

Published on: 09 September, 2020

Page: [336 - 361] Pages: 26

DOI: 10.2174/1389557520666200910091905

Price: $65

Abstract

Many plants in the genus Zanthoxylum, belonging to the Rutaceae family, are used as folk medicines for the treatment of various diseases, which have gained much attention for their phytochemical and pharmacological activity investigations. Alkaloids are the largest secondary metabolites with structurally diverse types found in this genus and they demonstrate a wide range of biological activities. The aim of this review is to provide a summary on the isolation, classification, and biological properties of alkaloids from Zanthoxylum species, which also will bring more attention to other researchers for further biological study on alkaloids for the new drug development.

Keywords: Zanthoxylum, alkaloid, quinoline, isoquinoline, classification, biological activities

« Previous Next »
Graphical Abstract

[1]
Zhang, D.X.; Thomas, G.H. In Flora of China; Science Press: Beijing, 2008, Vol. 11, pp. 53-66.
[2]
Bhattacharya, S.; Zaman, M.K. Pharmacognostical evaluation of Zanthoxylum nitidum bark. Int. J. Pharm. Tech. Res., 2009, 1(2), 292-298.
[3]
Zhu, L.J.; Ren, M.; Yang, T.C.; Qiao, C.; Chen, B.B.; Han, Z.Z.; Wang, S.H.; Wen, P.; Zhang, X. Four new alkylamides from the roots of Zanthoxylum nitidum. J. Asian Nat. Prod. Res.,, 2015, 17(7), 711-716.
[http://dx.doi.org/10.1080/10286020.2015.1049161] [PMID: 26096179]
[4]
Liu, H.; Feng, J.; Feng, K.; Lai, M. Optimization of the extraction conditions and quantification by RP-LC analysis of three alkaloids in Zanthoxylum nitidum roots. Pharm. Biol., 2014, 52(2), 255-261.
[http://dx.doi.org/10.3109/13880209.2013.826244] [PMID: 24074362]
[5]
Guetchueng, S.T.; Nahar, L.; Ritchie, K.J.; Ismail, F.M.; Evans, A.R.; Sarker, S.D. Zanthoamides G−I: Three new alkamides from Zanthoxylum zanthoxyloides. Phytochem. Lett., 2018, 26, 125-129.
[http://dx.doi.org/10.1016/j.phytol.2018.05.031]
[6]
Bhatt, V.; Kumar, N.; Sharma, U.; Singh, B. Comprehensive metabolic profiling of Zanthoxylum armatum and Zanthoxylum acanthopodium leaves, bark, flowers and fruits using ultra high performance liquid chromatography. Sep. Sci. Plus, 2018, 1(5), 311-324.
[http://dx.doi.org/10.1002/sscp.201800004]
[7]
Costa, R.S.; Souza Filho, O.P.; Dias Júnior, O.; Silva, J.J.; Hyaric, M.L.; Santos, M.A.; Velozo, E.S. In vitro antileishmanial and antitrypanosomal activity of compounds isolated from the roots of Zanthoxylum tingoassuiba. Rev. Bras. Farmacogn., 2018, 28(5), 551-558.
[http://dx.doi.org/10.1016/j.bjp.2018.04.013]
[8]
Nguyen, P.H.; Zhao, B.T.; Kim, O.; Lee, J.H.; Choi, J.S.; Min, B.S.; Woo, M.H. Anti-inflammatory terpenylated coumarins from the leaves of Zanthoxylum schinifolium with α-glucosidase inhibitory activity. J. Nat. Med., 2016, 70(2), 276-281.
[http://dx.doi.org/10.1007/s11418-015-0957-x] [PMID: 26753624]
[9]
Chen, J.J.; Chung, C.Y.; Hwang, T.L.; Chen, J.F. Amides and benzenoids from Zanthoxylum ailanthoides with inhibitory activity on superoxide generation and elastase release by neutrophils. J. Nat. Prod., 2009, 72(1), 107-111.
[http://dx.doi.org/10.1021/np800689b] [PMID: 19128011]
[10]
Guo, T.; Tang, X.F.; Chang, J.; Wang, Y. A new lignan glycoside from the stems of Zanthoxylum armatum DC. Nat. Prod. Res., 2017, 31(1), 16-21.
[http://dx.doi.org/10.1080/14786419.2016.1205064] [PMID: 27438679]
[11]
Thuy, T.T.; Porzel, A.; Ripperger, H.; Van Sung, T.; Adam, G. Bishordeninyl terpene alkaloids from Zanthoxylum avicennae. Phytochemistry, 1999, 50(5), 903-907.
[http://dx.doi.org/10.1016/S0031-9422(98)00612-8]
[12]
Ross, S.A.; Al-Azeib, M.A.; Krishnaveni, K.S.; Fronczek, F.R.; Burandt, C.L. Alkamides from the leaves of Zanthoxylum syncarpum. J. Nat. Prod., 2005, 68(8), 1297-1299.
[http://dx.doi.org/10.1021/np0580558] [PMID: 16124784]
[13]
Cheng, M.J.; Lee, K.H.; Tsai, I.L.; Chen, I.S. Two new sesquiterpenoids and anti-HIV principles from the root bark of Zanthoxylum ailanthoides. Bioorg. Med. Chem., 2005, 13(21), 5915-5920.
[http://dx.doi.org/10.1016/j.bmc.2005.07.050] [PMID: 16140017]
[14]
Wine-Show, S.; Ian-Lih, T.; Che-Ming, T.; Ih-Sheng, C. Nor-neolignan and phenyl propanoid from Zanthoxylum ailanthoides. Phytochemistry, 1994, 36(1), 213-215.
[http://dx.doi.org/10.1016/S0031-9422(00)97039-0]
[15]
Cheng, M.J.; Tsai, I.L.; Chen, I.S. Chemical constituents from the root bark of Formosan Zanthoxylum ailanthoides. J. Chin. Chem. Soc.-. Taip, 2003, 50(6), 1241-1246.
[16]
Tian, Y.; Zhang, C.; Guo, M. Comparative study on alkaloids and their anti-proliferative activities from three Zanthoxylum species. BMC Complement. Altern. Med., 2017, 17(1), 460.
[http://dx.doi.org/10.1186/s12906-017-1966-y] [PMID: 28899423]
[17]
Liu, J.; Zhang, Q.; Ye, Y.; Li, W.; Qiu, J.; Liu, J.; Zhan, R.; Chen, W.; Yu, Q. Angoline: a selective IL-6/STAT3 signaling pathway inhibitor isolated from Zanthoxylum nitidum. Phytomedicine, 2014, 21(8-9), 1088-1091.
[http://dx.doi.org/10.1016/j.phymed.2014.04.001] [PMID: 24863036]
[18]
Luo, X.; Pires, D.; Aínsa, J.A.; Gracia, B.; Duarte, N.; Mulhovo, S.; Anes, E.; Ferreira, M.J.U. Zanthoxylum capense constituents with antimycobacterial activity against Mycobacterium tuberculosis in vitro and ex vivo within human macrophages. J. Ethnopharmacol., 2013, 146(1), 417-422.
[http://dx.doi.org/10.1016/j.jep.2013.01.013] [PMID: 23337743]
[19]
Rahman, M.M.; Gray, A.I.; Khondkar, P.; Islam, M.A. Antimicrobial activities of alkaloids and lignans from Zanthoxylum budrunga. Nat. Prod. Commun., 2008, 3(1), 45-47.
[http://dx.doi.org/10.1177/1934578X0800300110]
[20]
Halstead, C.W.; Forster, P.I.; Waterman, P.G. Alkaloids from the stem bark of an Australian population of Zanthoxylum ovalifolium. Nat. Prod. Res., 2006, 20(10), 940-945.
[http://dx.doi.org/10.1080/14786410500462710] [PMID: 16854723]
[21]
Bodede, O.; Shaik, S.; Singh, M.; Moodley, R. Phytochemical analysis with antioxidant and cytotoxicity studies of the bioactive principles from Zanthoxylum capense (Small knobwood). Anti- Cancer Agent. Me., 2017, 17(4), 627-634.
[22]
Krane, B.D.; Fagbule, M.O.; Shamma, M.; Gözler, B. The benzophenanthridine alkaloids. J. Nat. Prod., 1984, 47(1), 1-43.
[http://dx.doi.org/10.1021/np50031a001]
[23]
Patiño, L.; Cuca, S. Chemical constituents of the wood from Zanthoxylum quinduense Tul. (Rutaceae). Quim. Nova, 2010, 33(5), 1019-1021.
[http://dx.doi.org/10.1590/S0100-40422010000500002]
[24]
Facundo, V.A.; Silveira, A.S.P.D.; Braz Filho, R.; Pinto, A.C.; Rezende, C.M. Constituintes químicos de Zanthoxylum ekmanii (URB.). Alain. Quim. Nova, 2005, 28, 224-225.
[http://dx.doi.org/10.1590/S0100-40422005000200010]
[25]
Moody, J.O.; Sofowora, A. Leaf alkaloids of Zanthoxylum rubescens. Planta Med., 1984, 50(1), 101-103.
[http://dx.doi.org/10.1055/s-2007-969634] [PMID: 17340264]
[26]
Rahman, M.M.; Islam, M.A.; Khondkar, P.; Gray, A.I. Alkaloids and lignans from Zanthoxylum budrunga (Rutaceae). Biochem. Syst. Ecol., 2005, 33(1), 91-96.
[http://dx.doi.org/10.1016/j.bse.2004.04.016]
[27]
Cheng, M.J.; Lin, C.F.; Chang, H.S.; Chen, I.S. Chemical constituents from the stem bark of Zanthoxylum scandens. J. Chil. Chem. Soc., 2008, 53(3), 1631-1634.
[http://dx.doi.org/10.4067/S0717-97072008000300019]
[28]
Tavares, Lde. C.; Zanon, G.; Weber, A.D.; Neto, A.T.; Mostardeiro, C.P.; Da Cruz, I.B.; Oliveira, R.M.; Ilha, V.; Dalcol, I.I.; Morel, A.F. Structure-activity relationship of benzophenanthridine alkaloids from Zanthoxylum rhoifolium having antimicrobial activity. PLoS One, 2014, 9(5)e97000
[http://dx.doi.org/10.1371/journal.pone.0097000] [PMID: 24824737]
[29]
Sandjo, L.P.; Kuete, V.; Tchangna, R.S.; Efferth, T.; Ngadjui, B.T. Cytotoxic benzophenanthridine and furoquinoline alkaloids from Zanthoxylum buesgenii (Rutaceae). Chem. Cent. J., 2014, 8(1), 61.
[http://dx.doi.org/10.1186/s13065-014-0061-4] [PMID: 25349626]
[30]
Li, W.; Yang, S.Y.; Yan, X.T.; Sun, Y.N.; Song, S.B.; Kang, H.K.; Kim, Y.H. NF-κB inhibitory activities of glycosides and alkaloids from Zanthoxylum schinifolium stems. Chem. Pharm. Bull. (Tokyo), 2014, 62(2), 196-202.
[http://dx.doi.org/10.1248/cpb.c13-00759] [PMID: 24492590]
[31]
Zhao, L.N.; Guo, X.X.; Liu, S.; Feng, L.; Bi, Q.R.; Wang, Z.; Tan, N.H. (±)-Zanthonitidine A, a pair of enantiomeric furoquinoline alkaloids from Zanthoxylum nitidum with antibacterial activity. Nat. Prod. Bioprospect., 2018, 8(5), 361-367.
[http://dx.doi.org/10.1007/s13659-018-0169-7] [PMID: 29855857]
[32]
Ngoumfo, R.M.; Jouda, J.B.; Mouafo, F.T.; Komguem, J.; Mbazoa, C.D.; Shiao, T.C.; Choudhary, M.I.; Laatsch, H.; Legault, J.; Pichette, A.; Roy, R. In vitro cytotoxic activity of isolated acridones alkaloids from Zanthoxylum leprieurii Guill. et Perr. Bioorg. Med. Chem., 2010, 18(10), 3601-3605.
[http://dx.doi.org/10.1016/j.bmc.2010.03.040] [PMID: 20413315]
[33]
Wouatsa, V.N.; Misra, L.; Kumar, S.; Prakash, O.; Khan, F.; Tchoumbougnang, F.; Venkatesh, R.K. Aromatase and glycosyl transferase inhibiting acridone alkaloids from fruits of Cameroonian Zanthoxylum species. Chem. Cent. J., 2013, 7(1), 125.
[http://dx.doi.org/10.1186/1752-153X-7-125] [PMID: 23866063]
[34]
Wang, C.; Wan, J.; Mei, Z.; Yang, X. Acridone alkaloids with cytotoxic and antimalarial activities from Zanthoxylum simullans Hance. Pharmacogn. Mag., 2014, 10(37), 73-76.
[http://dx.doi.org/10.4103/0973-1296.126669] [PMID: 24696549]
[35]
Wansi, J.D.; Tcho, A.T.; Toze, F.A.A.; Nahar, L.; Martin, C.; Sarker, S.D. Cytotoxic acridone and indoloquinazoline alkaloids from Zanthoxylum poggei. Phytochem. Lett., 2016, 17, 293-298.
[http://dx.doi.org/10.1016/j.phytol.2016.08.010]
[36]
Chen, I.S.; Wu, S.J.; Leu, Y.L.; Tsai, I.W.; Wu, T.S. Alkaloids from root bark of Zanthoxylum simulans. Phytochemistry, 1996, 42(1), 217-219.
[http://dx.doi.org/10.1016/0031-9422(95)00856-X] [PMID: 8588867]
[37]
Yang, Z.D.; Zhang, D.B.; Ren, J.; Yang, M.J. Skimmianine, a furoquinoline alkaloid from Zanthoxylum nitidum as a potential acetylcholinesterase inhibitor. Med. Chem. Res., 2012, 21(6), 722-725.
[http://dx.doi.org/10.1007/s00044-011-9581-9]
[38]
Tarus, P.K.; Coombes, P.H.; Crouch, N.R.; Mulholland, D.A. Benzo[c]phenanthridine alkaloids from stem bark of the Forest Knobwood, Zanthoxylum davyi (Rutaceae). S. Afr. J. Bot., 2006, 72(4), 555-558.
[http://dx.doi.org/10.1016/j.sajb.2006.03.014]
[39]
de Moura, N.F.; Morel, A.F.; Dessoy, E.C.; Zanatta, N.; Bürger, M.M.; Ahlert, N.; Porto, G.P.; Baldisserotto, B. Alkaloids, amides and antispasmodic activity of Zanthoxylum hyemale. Planta Med., 2002, 68(6), 534-538.
[http://dx.doi.org/10.1055/s-2002-32550] [PMID: 12094298]
[40]
Arruda, M.S.; Fernandes, J.B.; da Silva, M.F.D.G.; Vieira, P.C.; Pirani, J.R. Quinolone alkaloids from Zanthoxylum acutifolium. Phytochemistry, 1992, 31(10), 3617-3619.
[http://dx.doi.org/10.1016/0031-9422(92)83738-K]
[41]
Brader, G.; Wurz, G.; Greger, H.; Hofer, O. Novel prenylated 2-quinolinones from east Asian Zanthoxylum species. Liebigs Ann. Chem., 1993, 1993(4), 355-358.
[http://dx.doi.org/10.1002/jlac.199319930160]
[42]
Ahmad, M.U.; Rahman, M.A.; Huq, E.; Chowdhury, R. Alkaloids of Zanthoxylum budrunga Fitoterapia,., 2003, 74(1-2), 191-193.
[http://dx.doi.org/10.1016/S0367-326X(02)00286-1] [PMID: 12628423]
[43]
Tangjitjaroenkun, J.; Chantarasriwong, O.; Chavasiri, W. Chemical constituents of the stems of Zanthoxylum limonella Alston. Phytochem. Lett., 2012, 5(3), 443-445.
[http://dx.doi.org/10.1016/j.phytol.2012.04.001]
[44]
Nguyen, T.H.V.; Tran, T.T.; Cam, T.I.; Pham, M.Q.; Pham, Q.L.; Vu, D.H.; Nguyen, X.N.; Chau, V.M.; Van, K.P. Alkaloids from Zanthoxylum nitidum and their cytotoxic activity. Nat. Prod. Commun., 2019, 14(5), 1-5.
[http://dx.doi.org/10.1177/1934578X19844133]
[45]
Chen, I.S.; Tsai, I.W.; Teng, C.M.; Chen, J.J.; Chang, Y.L.; Ko, F.N.; Lu, M.C.; Pezzuto, J.M. Pyranoquinoline alkaloids from Zanthoxylum simulans. Phytochemistry, 1997, 46(3), 525-529.
[http://dx.doi.org/10.1016/S0031-9422(97)00280-X]
[46]
Shwu-Jen, W.; Ih-Sheng, C. Alkaloids from Zanthoxylum simulans. Phytochemistry, 1993, 34(6), 1659-1661.
[http://dx.doi.org/10.1016/S0031-9422(00)90870-7]
[47]
Ih-Sheng, C.; Shwu-Jen, W.; Yuh-Chwen, L.; Ian-Lih, T.; Seki, H.; Feng-Nien, K.; Che-Ming, T. Dimeric 2-quinolone alkaloid and antiplatelet aggregation constituents of Zanthoxylum simulans. Phytochemistry, 1994, 36(1), 237-239.
[http://dx.doi.org/10.1016/S0031-9422(00)97045-6] [PMID: 7765612]
[48]
Zhao, L.N.; Wang, J.; Wang, Z.; Tan, N.H. Chemical and cytotoxic constituents of Zanthoxylum nitidum. Zhongguo Zhongyao Zazhi, 2018, 43(23), 4659-4664.
[PMID: 30717555]
[49]
Ahsan, M.; Haque, M.R.; Hossain, M.B.; Islam, S.N.; Gray, A.I.; Hasan, C.M. Cytotoxic dimeric quinolone-terpene alkaloids from the root bark of Zanthoxylum rhetsa. Phytochemistry, 2014, 103, 8-12.
[http://dx.doi.org/10.1016/j.phytochem.2014.03.008] [PMID: 24768324]
[50]
Chen, J.J.; Chen, P.H.; Liao, C.H.; Huang, S.Y.; Chen, I.S. New phenylpropenoids, bis(1-phenylethyl)phenols, bisquinolinone alkaloid, and anti-inflammatory constituents from Zanthoxylum integrifoliolum. J. Nat. Prod., 2007, 70(9), 1444-1448.
[http://dx.doi.org/10.1021/np070186g] [PMID: 17822293]
[51]
Cho, J.Y.; Hwang, T.L.; Chang, T.H.; Lim, Y.P.; Sung, P.J.; Lee, T.H.; Chen, J.J. New coumarins and anti-inflammatory constituents from Zanthoxylum avicennae. Food Chem., 2012, 135(1), 17-23.
[http://dx.doi.org/10.1016/j.foodchem.2012.04.025]
[52]
Van, N.T.H.; Tuyen, T.T.; Quan, P.M.; Long, P.Q.; Nhiem, N.X.; Tai, B.H.; Inh, C.T.; Hoang, V.D.; Kiem, P.V.; Min, C.V.; Park, S.J.; Kim, S.H.; Park, S. Alkaloid glycosides and their cytotoxic constituents from Zanthoxylum nitidum. Phytochem. Lett., 2019, 32, 47-51.
[http://dx.doi.org/10.1016/j.phytol.2019.04.022]
[53]
Martin, M.T.; Rasoanaivo, L.H.; Raharisololalao, A. Phenanthridine alkaloids from Zanthoxylum madagascariense. Fitoterapia, 2005, 76(6), 590-593.
[http://dx.doi.org/10.1016/j.fitote.2005.04.003] [PMID: 16000237]
[54]
Wang, C.F.; Fan, L.; Tian, M.; Du, S.S.; Deng, Z.W.; Feng, J.B.; Wang, Y.Y.; Su, X. Cytotoxicity of benzophenanthridine alkaloids from the roots of Zanthoxylum nitidum (Roxb.) DC. var. fastuosum How ex Huang. Nat. Prod. Res., 2015, 29(14), 1380-1383.
[http://dx.doi.org/10.1080/14786419.2014.1002090] [PMID: 25647513]
[55]
Wang, C.F.; You, C.X.; Yang, K.; Guo, S.S.; Geng, Z.F.; Fan, L.; Dua, S.S.; Deng, Z.W.; Wang, Y.Y. Antifeedant activities of methanol extracts of four Zanthoxylum species and benzophenanthridines from stem bark of Zanthoxylum schinifolium against Tribolium castaneum. Ind. Crops Prod., 2015, 74, 407-411.
[http://dx.doi.org/10.1016/j.indcrop.2015.05.045]
[56]
Chen, J.J.; Fang, H.Y.; Duh, C.Y.; Chen, I.S. New indolopyridoquinazoline, benzo[c]phenanthridines and cytotoxic constituents from Zanthoxylum integrifoliolum. Planta Med., 2005, 71(5), 470-475.
[http://dx.doi.org/10.1055/s-2005-864144] [PMID: 15931588]
[57]
de Moura, N.F.; Ribeiro, H.B.; Machado, E.C.; Ethur, E.M.; Zanatta, N.; Morel, A.F. Benzophenanthridine alkaloids from Zanthoxylum rhoifolium. Phytochemistry, 1997, 46(8), 1443-1446.
[http://dx.doi.org/10.1016/S0031-9422(97)00498-6]
[58]
He, W.; Van Puyvelde, L.; De Kimpe, N.; Verbruggen, L.; Anthonissen, K.; Van der Flaas, M.; Bosselaers, J.; Mathenge, S.G.; Mudida, F.P. Chemical constituents and biological activities of Zanthoxylum usambarense. Phytother. Res., 2002, 16(1), 66-70.
[http://dx.doi.org/10.1002/ptr.849] [PMID: 11807969]
[59]
Liang, M.; Zhang, W.; Hu, J.; Liu, R.; Zhang, C. Simultaneous analysis of alkaloids from Zanthoxylum nitidum by high performance liquid chromatography-diode array detector-electrospray tandem mass spectrometry. J. Pharm. Biomed. Anal., 2006, 42(2), 178-183.
[http://dx.doi.org/10.1016/j.jpba.2006.03.031] [PMID: 16730156]
[60]
Cui, X.G.; Zhao, Q.J.; Chen, Q.L.; Xu, L.; Song, Y.; Jin, Y.S.; Xu, D.F. Two new benzophenanthridine alkaloids from Zanthoxylum nitidum. Helv. Chim. Acta, 2008, 91(1), 155-158.
[http://dx.doi.org/10.1002/hlca.200890006]
[61]
de A Gonzaga. W.; Weber, A.D.; Giacomelli, S.R.; Dalcol, I.I.; Hoelzel, S.C.; Morel, A.F. Antibacterial alkaloids from Zanthoxylum rhoifolium. Planta Med., 2003, 69(04), 371-374.
[62]
Yang, S.H.; Liu, Y.Q.; Wang, J.F.; Wang, Y.H.; Pan, W.W.; Sheng, W.B.; Cai, R.; Zhou, X.J. Isoquinoline alkaloids from Zanthoxylum simulans and their biological evaluation. J. Antibiot. (Tokyo), 2015, 68(4), 289-292.
[http://dx.doi.org/10.1038/ja.2014.139] [PMID: 25269466]
[63]
Chen, I.S.; Wu, S.J.; Tsai, I.L.; Wu, T.S.; Pezzuto, J.M.; Lu, M.C.; Chai, H.; Suh, N.; Teng, C.M. Chemical and bioactive constituents from Zanthoxylum simulans. J. Nat. Prod., 1994, 57(9), 1206-1211.
[http://dx.doi.org/10.1021/np50111a003] [PMID: 7798955]
[64]
Hu, J.; Zhang, W.D.; Liu, R.H.; Zhang, C.; Shen, Y.H.; Li, H.L.; Liang, M.J.; Xu, X.K. Benzophenanthridine alkaloids from Zanthoxylum nitidum (Roxb.) DC, and their analgesic and anti-inflammatory activities. Chem. Biodivers., 2006, 3(9), 990-995.
[http://dx.doi.org/10.1002/cbdv.200690108] [PMID: 17193331]
[65]
Nissanka, A.P.; Karunaratne, V.; Bandara, B.M.; Kumar, V.; Nakanishi, T.; Nishi, M.; Inada, A.; Tillekeratne, L.M.V.; Wijesundara, D.S.A.; Gunatilaka, A.A.L.; Gunatilaka, A.L. Antimicrobial alkaloids from Zanthoxylum tetraspermum and caudatum. Phytochemistry, 2001, 56(8), 857-861.
[http://dx.doi.org/10.1016/S0031-9422(00)00402-7] [PMID: 11324918]
[66]
Fernandes, C.C.; Vieira, P.C.; Silva, V.C.D.; Dall’Oglio, E.L.; Silva, L.E.D.; Sousa, P.T.D., Jr 6-Acetonyl-N-methyl-dihydrodecarine, a new alkaloid from Zanthoxylum riedelianum. J. Brazil. Chem. Soc., 2009, 20(2), 379-382.
[67]
Luo, X.; Pedro, L.; Milic, V.; Mulhovo, S.; Duarte, A.; Duarte, N.; Ferreira, M.J.U. Antibacterial benzofuran neolignans and benzophenanthridine alkaloids from the roots of Zanthoxylum capense. Planta Med., 2012, 78(2), 148-153.
[http://dx.doi.org/10.1055/s-0031-1280289] [PMID: 22002848]
[68]
Tane, P.; Wabo, H.K.; Connolly, J.D. A new benzophenanthridine alkaloid from Zanthoxylum buesgenii. Fitoterapia, 2005, 76(7-8), 656-660.
[http://dx.doi.org/10.1016/j.fitote.2005.08.018] [PMID: 16242267]
[69]
Ladino, O.J.P.; Suárez, L.E.C. Isoquinoline alkaloids of Zanthoxylum quinduense (Rutaceae). Biochem. Syst. Ecol., 2010, 38(4), 853-856.
[http://dx.doi.org/10.1016/j.bse.2010.07.016]
[70]
Rodríguez-Guzmán, R.; Fulks, L.C.J.; Radwan, M.M.; Burandt, C.L.; Ross, S.A. Chemical constituents, antimicrobial and antimalarial activities of Zanthoxylum monophyllum. Planta Med., 2011, 77(13), 1542-1544.
[http://dx.doi.org/10.1055/s-0030-1270782] [PMID: 21341176]
[71]
Yang, G.; Chen, D. Alkaloids from the roots of Zanthoxylum nitidum and their antiviral and antifungal effects. Chem. Biodivers., 2008, 5(9), 1718-1722.
[http://dx.doi.org/10.1002/cbdv.200890160] [PMID: 18816524]
[72]
Yao-Kouassi, P.A.; Caron, C.; Ramiarantsoa, H.; Prost, É.; Harakat, D.; Le Magrex-Debar, É.; Zèches-Hanrot, M. New nitro-benzo[c]phenanthridine and indolopyridoquinazoline alkaloids from Zanthoxylum atchoum. C. R. Chim., 2015, 18(8), 891-897.
[http://dx.doi.org/10.1016/j.crci.2015.01.005]
[73]
Wu, S.J.; Chen, I.S.; Teng, C.M.; Wu, T.S. Structure and synthesis of simulansamide, a platelet aggregation inhibitor from Zanthoxylum simulans. J. Chin. Chem. Soc.-. Taip., 1996, 43(2), 195-198.
[74]
Hu, J.; Zhang, W.D.; Shen, Y.H.; Zhang, C.; Xu, L.; Liu, R.H.; Xu, X.K. Alkaloids from Zanthoxylum nitidum (Roxb.) DC. Biochem. Syst. Ecol., 2007, 2(35), 114-117.
[http://dx.doi.org/10.1016/j.bse.2006.10.001]
[75]
Wangensteen, H.; Ho, G.T.T.; Tadesse, M.; Miles, C.O.; Moussavi, N.; Mikolo, B.; Malterud, K.E. A new benzophenanthridine alkaloid and other bioactive constituents from the stem bark of Zanthoxylum heitzii. Fitoterapia, 2016, 109, 196-200.
[http://dx.doi.org/10.1016/j.fitote.2016.01.012] [PMID: 26802607]
[76]
Fan, M.; Tian, Y.; Chen, G.; Sarker, S.D.; Nahar, L.; Wu, J.; Li, N.; Guo, M. Enrichment and analysis of quaternary alkaloids from Zanthoxylum simulans using weak cation exchange solid-phase extraction coupled with LC-MS. Phytochem. Anal., 2019, 30(6), 727-734.
[http://dx.doi.org/10.1002/pca.2860] [PMID: 31317605]
[77]
Queiroz, E.F.; Hay, A.E.; Chaaib, F.; van Diemen, D.; Diallo, D.; Hostettmann, K. New and bioactive aromatic compounds from Zanthoxylum zanthoxyloides. Planta Med., 2006, 72(8), 746-750.
[http://dx.doi.org/10.1055/s-2006-941504] [PMID: 16783692]
[78]
Bongui, J.B.; Blanckaert, A.; Elomri, A.; Seguin, E. Constituents of Zanthoxylum heitzii (Rutaceae). Biochem. Syst. Ecol., 2005, 8(33), 845-847.
[http://dx.doi.org/10.1016/j.bse.2004.12.019]
[79]
Kato, A.; Moriyasu, M.; Ichimaru, M.; Nishiyama, Y.; Juma, F.D.; Nganga, J.N.; Mathenge, S.G.; Ogeto, J.O. Isolation of alkaloidal constituents of Zanthoxylum usambarense and Zanthoxylum chalybeum using ion-pair HPLC. J. Nat. Prod., 1996, 59(3), 316-318.
[http://dx.doi.org/10.1021/np960183w]
[80]
Penali, L.; Mulholland, D.A.; Tano, K.D.; Cheplogoi, P.K.; Randrianarivelojosia, M. Low antiplasmodial activity of alkaloids and amides from the stem bark of Zanthoxylum rubescens (Rutaceae). Parasite, 2007, 14(2), 161-164.
[http://dx.doi.org/10.1051/parasite/2007142161] [PMID: 17645189]
[81]
Cai, M.; Zhou, Y.; Wang, X.; Li, R.; Liao, X.; Ding, L. Rapid structural characterization of isomeric benzo[c]phenanthridine alkaloids from the roots of Zanthoxylum nitidium by liquid chromatography combined with electrospray ionization tandem mass spectrometry. Rapid Commun. Mass Spectrom., 2007, 21(12), 1931-1936.
[http://dx.doi.org/10.1002/rcm.3045] [PMID: 17510939]
[82]
Yang, C.H.; Cheng, M.J.; Chiang, M.Y.; Kuo, Y.H.; Wang, C.J.; Chen, I.S. Dihydrobenzo[c]phenanthridine alkaloids from stem bark of Zanthoxylum nitidum. J. Nat. Prod., 2008, 71(4), 669-673.
[http://dx.doi.org/10.1021/np700745f] [PMID: 18303853]
[83]
Yang, C.H.; Cheng, M.J.; Lee, S.J.; Yang, C.W.; Chang, H.S.; Chen, I.S. Secondary metabolites and cytotoxic activities from the stem bark of Zanthoxylum nitidum. Chem. Biodivers., 2009, 6(6), 846-857.
[http://dx.doi.org/10.1002/cbdv.200800107] [PMID: 19551734]
[84]
Cheng, M.J.; Wu, C.C.; Tsai, I.L.; Chen, I.S. Chemical and antiplatelet constituents from the stem of Zanthoxylum beecheyanum. J. Chin. Chem. Soc.-. Taip., 2004, 51(5A), 1065-1072.
[85]
Samita, F.N.; Sandjo, L.P.; Ndiege, I.O.; Hassanali, A.; Lwande, W. Zanthoxoaporphines A-C: Three new larvicidal dibenzo[de,g]quinolin-7-one alkaloids from Zanthoxylum paracanthum (Rutaceae). Beilstein J. Org. Chem., 2013, 9(1), 447-452.
[http://dx.doi.org/10.3762/bjoc.9.47] [PMID: 23504306]
[86]
Simeray, J.; Chaumont, J.P.; Pusset, J.; Bévalot, F.; Vaquette, J. Plants from New Caledonia: Constituents of Zanthoxylum sarasinii. Planta Med., 1988, 54(2), 189-190.
[http://dx.doi.org/10.1055/s-2006-962398] [PMID: 17265248]
[87]
Binutu, O.A.; Cordell, G.A. Constituents of Zanthoxylum sprucei. Pharm. Biol., 2000, 38(3), 210-213.
[http://dx.doi.org/10.1076/1388-0209(200007)3831-SFT210] [PMID: 21214464]
[88]
Patiño, O.J.; Cuca, L.E. Monophyllidin, a new alkaloid L-proline derivative from Zanthoxylum monophyllum. Phytochem. Lett., 2011, 4(1), 22-25.
[http://dx.doi.org/10.1016/j.phytol.2010.10.002]
[89]
Rios, M.Y.; Córdova-Albores, L.C.; Ramírez-Cisneros, M.Á.; King-Díaz, B.; Lotina-Hennsen, B.; León Rivera, I.; Miranda-Sánchez, D. Phytotoxic potential of Zanthoxylum affine and its major compound linarin as a possible natural herbicide. ACS Omega, 2018, 3(11), 14779-14787.
[http://dx.doi.org/10.1021/acsomega.8b02020] [PMID: 30555988]
[90]
Hu, J.; Zhang, W.D.; Shen, Y.H.; Zhang, C.; Liu, R.H.; Xu, X.K.; Wang, B. Two novel alkaloids from Zanthoxylum nitidum. Helv. Chim. Acta, 2007, 90(4), 720-722.
[http://dx.doi.org/10.1002/hlca.200790071]
[91]
Chen, J.J.; Lin, Y.H.; Day, S.H.; Hwang, T.L.; Chen, I.S. New benzenoids and anti-inflammatory constituents from Zanthoxylum nitidum. Food Chem., 2011, 125(2), 282-287.
[http://dx.doi.org/10.1016/j.foodchem.2010.09.069]
[92]
Hu, J.; Shi, X.; Mao, X.; Chen, J.; Li, H. Cytotoxic mannopyranosides of indole alkaloids from Zanthoxylum nitidum. Chem. Biodivers., 2014, 11(6), 970-974.
[http://dx.doi.org/10.1002/cbdv.201300381] [PMID: 24934682]
[93]
Krohn, K.; Cludius-Brandt, S.; Schulz, B.; Sreelekha, M.; Shafi, P.M. Isolation, structure elucidation, and biological activity of a new alkaloid from Zanthoxylum rhetsa. Nat. Prod. Commun., 2011, 6(11), 1595-1596.
[http://dx.doi.org/10.1177/1934578X1100601110] [PMID: 22224269]
[94]
Rivero, I.A.; Espinoza, K.; Somanathan, R. Syntheses of quinazoline-2,4-dione alkaloids and analogues from Mexican Zanthoxylum species. Molecules, 2004, 9(7), 609-616.
[http://dx.doi.org/10.3390/90700609] [PMID: 18007461]
[95]
Banerjee, H.; Pal, S.; Adityachaudhury, N. Occurrence of rutaecarpine in Zanthoxylum budrunga. Planta Med., 1989, 55(4), 403-403.
[http://dx.doi.org/10.1055/s-2006-962049] [PMID: 17262449]
[96]
Sheen, W.S.; Tsai, I.L.; Teng, C.M.; Ko, F.N.; Chen, I.S. Indolopyridoquinazoline alkaloids with antiplatelet aggregation activity from Zanthoxylum integrifoliolum. Planta Med., 1996, 62(2), 175-176.
[http://dx.doi.org/10.1055/s-2006-957846] [PMID: 8657756]
[97]
Samad, A.; Badshah, S.; Khan, D.; Ali, F.; Amanullah, M.; Hanrahan, J. New prenylated carbazole alkaloids from Zanthoxylum armatum. J. Asian Nat. Prod. Res., 2014, 16(12), 1126-1131.
[http://dx.doi.org/10.1080/10286020.2014.967228] [PMID: 25355272]
[98]
Ferreira, M.E.; Rojas de Arias, A.; Torres de Ortiz, S.; Inchausti, A.; Nakayama, H.; Thouvenel, C.; Hocquemiller, R.; Fournet, A. Leishmanicidal activity of two canthin-6-one alkaloids, two major constituents of Zanthoxylum chiloperone var. angustifolium. J. Ethnopharmacol., 2002, 80(2-3), 199-202.
[http://dx.doi.org/10.1016/S0378-8741(02)00025-9] [PMID: 12007711]
[99]
Ferreira, M.E.; Nakayama, H.; de Arias, A.R.; Schinini, A.; de Bilbao, N.V.; Serna, E.; Lagoutte, D.; Soriano-Agatón, F.; Poupon, E.; Hocquemiller, R.; Fournet, A. Effects of canthin-6-one alkaloids from Zanthoxylum chiloperone on Trypanosoma cruzi-infected mice. J. Ethnopharmacol., 2007, 109(2), 258-263.
[http://dx.doi.org/10.1016/j.jep.2006.07.028] [PMID: 16949231]
[100]
Chakthong, S.; Ampaprom, R.; Inparn, S.; Phetkul, U.; Chusri, S.; Limsuwan, S.; Voravuthikunchai, S.P. New alkylamide from the stems of Zanthoxylum nitidum. Nat. Prod. Res., 2019, 33(2), 153-161.
[http://dx.doi.org/10.1080/14786419.2018.1440218] [PMID: 29457506]
[101]
Yang, Y.P.; Cheng, M.J.; Teng, C.M.; Chang, Y.L.; Tsai, I.L.; Chen, I.S. Chemical and anti-platelet constituents from Formosan Zanthoxylum simulans. Phytochemistry, 2002, 61(5), 567-572.
[http://dx.doi.org/10.1016/S0031-9422(02)00268-6] [PMID: 12409024]
[102]
Rodríguez-Guzmán, R.; Radwan, M.M.; Burandt, C.L.; Williamson, J.S.; Ross, S.A. Xenobiotic biotransformation of 4-methoxy-N-methyl-2-quinolone, isolated from Zanthoxylum monophyllum. Nat. Prod. Commun., 2010, 5(9), 1463-1464.
[http://dx.doi.org/10.1177/1934578X1000500923] [PMID: 20923009]
[103]
Tantapakul, C.; Phakhodee, W.; Ritthiwigrom, T.; Yossathera, K.; Deachathai, S.; Laphookhieo, S. Antibacterial compounds from Zanthoxylum rhetsa. Arch. Pharm. Res., 2012, 35(7), 1139-1142.
[http://dx.doi.org/10.1007/s12272-012-0703-9] [PMID: 22864735]
[104]
Ross, S.A.; Sultana, G.N.; Burandt, C.L.; ElSohly, M.A.; Marais, J.P.; Ferreira, D. Syncarpamide, a new antiplasmodial (+)-norepinephrine derivative from Zanthoxylum syncarpum. J. Nat. Prod., 2004, 67(1), 88-90.
[http://dx.doi.org/10.1021/np030417t] [PMID: 14738394]
[105]
Goodman, C.D.; Austarheim, I.; Mollard, V.; Mikolo, B.; Malterud, K.E.; McFadden, G.I.; Wangensteen, H. Natural products from Zanthoxylum heitzii with potent activity against the malaria parasite. Malar. J., 2016, 15(1), 481.
[http://dx.doi.org/10.1186/s12936-016-1533-x] [PMID: 27649682]
[106]
Hu, J.; Shi, X.; Mao, X.; Chen, J.; Zhu, L.; Zhao, Q. Antinociceptive activity of Rhoifoline A from the ethanol extract of Zanthoxylum nitidum in mice. J. Ethnopharmacol., 2013, 150(3), 828-834.
[http://dx.doi.org/10.1016/j.jep.2013.04.035] [PMID: 23669135]
[107]
Talontsi, F.M.; Matasyoh, J.C.; Ngoumfo, R.M.; Chepkorir, R. Mosquito larvicidal activity of alkaloids from Zanthoxylum lemairei against the malaria vector Anopheles gambiae. Pestic. Biochem. Physiol., 2011, 99(1), 82-85.
[http://dx.doi.org/10.1016/j.pestbp.2010.11.003]
[108]
Garcez, W.S.; Garcez, F.R.; da Silva, L.M.; Hamerski, L. Larvicidal activity against Aedes aegypti of some plants native to the West-Central region of Brazil. Bioresour. Technol., 2009, 100(24), 6647-6650.
[http://dx.doi.org/10.1016/j.biortech.2009.06.092] [PMID: 19664915]
[109]
Ferreira, M.E.; de Arias, A.R.; Yaluff, G.; de Bilbao, N.V.; Nakayama, H.; Torres, S.; Schinini, A.; Guy, I.; Heinzen, H.; Fournet, A. Antileishmanial activity of furoquinolines and coumarins from Helietta apiculata. Phytomedicine, 2010, 17(5), 375-378.
[http://dx.doi.org/10.1016/j.phymed.2009.09.009] [PMID: 19879121]
[110]
Östan, I.; Saglam, H.; Limoncu, M.E.; Ertabaklar, H.; Toz, S.Ö.; Özbel, Y.; Özbilgin, A. In vitro and in vivo activities of Haplophyllum myrtifolium against Leishmania tropica. New Microbiol., 2007, 30(4), 439-445.
[PMID: 18080680]

Rights & Permissions Print Cite
Article Metrics
34
© 2024 Bentham Science Publishers | Privacy Policy