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Current Bioactive Compounds

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ISSN (Print): 1573-4072
ISSN (Online): 1875-6646

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Review Article

Health Benefits of Ipecac and Cephaeline: their Potential in Health Promotion and Disease Prevention

Author(s): Kanika Patel and Dinesh K. Patel*

Volume 17, Issue 3, 2021

Published on: 09 June, 2020

Page: [206 - 213] Pages: 8

DOI: 10.2174/1573407216999200609130841

Price: $65

Abstract

Background: Cephaelis ipecacuanha and Cephaelis acuminate commonly called Ipecac are the important medicinal plants of Cephaelis species belonging to Rubiaceae family. Ipecac is cultivated throughout the world due to their vast of therapeutic applications in gastrointestinal disorders and poisoning cases.

Methods: In the present review paper medicinal importance of Ipecac and their main active phytoconstituents cephaeline have been discussed and presented in concise manner to explore their hidden potential. Phytochemical aspects of Ipecac and overview of cephaeline have been also discussed in the present paper. However important Pharmacological activities of cephaeline on gastrointestinal tract, cardiovascular system, Zika virus, Ebola virus, leishmania and malaria have been mainly focused in the present paper. Further important analytical techniques of detection and separation of cephaeline have also been presented in the present paper. Present paper also contains information of Tissue culture techniques of Ipecac for the better production of cephaeline to fulfil the industrial demands.

Results: Cephaeline is colourless crystalline active compound of Ipecac plant which is having chemical formula C28H38O4N2. Claimed pharmacological activities of Ipecac such as diaphoretic, expectorant and anti-amoebic are mainly due to the presence of alkaloidal class chemical emetine and cephaeline. Result also revealed that ethanol extract of Ipecac has been used as emetic agents. Phytochemical analysis of the Ipecac revealed the presence of emetine, cephaeline, protoemetine, psychotrine, emetamine, O-methylpsychotrine and psychotrine methyl ether. Pharmacologically cephaeline induces vomiting through acting on stomach lining but it is more toxic and irritant compared to the emetine.

Conclusion: The presented information will be beneficial to the scientific communities to know the importance of Ipecac and their main active phytoconstituents cephaeline for the treatment of numerous health related complication.

Keywords: Analytical techniques, cephaeline, Cephaelis acuminate, Cephaelis ipecacuanha, emesis, Ipecac, pharmacological activity.

Graphical Abstract

[1]
Patel, K.; Kumar, V.; Rahman, M.; Verma, A.; Patel, D.K. New insights into the medicinal importance, physiological functions and bioanalytical aspects of an important bioactive compound of foods ‘Hyperin’: Health benefits of the past, the present, the future. Beni-Suef. Univ. J. Basic Appl. Sci., 2018, 7, 31-42.
[http://dx.doi.org/10.1016/j.bjbas.2017.05.009]
[2]
Patel, K.; Kumar, V.; Rahman, M.; Verma, A.; Patel, D.K. Rhamnazin: A systematic review on ethnopharmacology, pharmacology and analytical aspects of an important phytomedicine. Curr. Tradit. Med., 2018, 4, 120-127.
[http://dx.doi.org/10.2174/2215083804666180416124949]
[3]
Patel, K.; Kumar, V.; Verma, A.; Rahman, M.; Patel, D.K. β-sitosterol: Bioactive compounds in foods, their role in health promotion and disease prevention “a concise report of its phytopharmaceutical importance”. Curr. Tradit. Med., 2017, 3, 168-177.
[http://dx.doi.org/10.2174/2215083803666170615111759]
[4]
Patel, K.; Kumar, V.; Verma, A.; Rahman, M.; Patel, D.K. Amarogentin as topical anticancer and anti-infective potential: Scope of lipid based vesicular in its effective delivery. Recent Pat. Antiinfect. Drug Discov., 2018, 14(1), 7-15.
[5]
Patel, K.; Patel, D.K. Medicinal importance, pharmacological activities, and analytical aspects of hispidulin: A concise report. J. Tradit. Complement. Med., 2016, 7(3), 360-366.
[http://dx.doi.org/10.1016/j.jtcme.2016.11.003] [PMID: 28725632]
[6]
Patel, K.; Patel, D.K. Medicinal significance, pharmacological activities, and analytical aspects of ricinine: A concise report. J. Coast. Life Med., 2016, 4, 663-667.
[http://dx.doi.org/10.12980/jclm.4.2016J6-96]
[7]
Patel, K.; Mishra, R.; Patel, D.K. A review on phytopharmaceutical importance of asiaticoside. J. Coast. Life Med., 2016, 4, 1000-1007.
[http://dx.doi.org/10.12980/jclm.4.2016J6-161]
[8]
Rout, G.; Samantaray, S.; Das, P. In vitro somatic embryogenesis from callus cultures of Cephaelis ipecacuanha A. Richard. Sci. Hortic. (Amsterdam), 2000, 86, 71-79.
[http://dx.doi.org/10.1016/S0304-4238(00)00130-8]
[9]
Queiroz, Cde.S.; Batista, F.R.; de Oliveira, L.O. Evolution of the 5.8S nrDNA gene and internal transcribed spacers in Carapichea ipecacuanha (Rubiaceae) within a phylogeographic context. Mol. Phylogenet. Evol., 2011, 59(2), 293-302.
[http://dx.doi.org/10.1016/j.ympev.2011.01.013] [PMID: 21300163]
[10]
Alves Garcia, R.M.; de Oliveira, L.O.; Alves Moreira, M.; Silva Barros, W. Variation in emetine and cephaeline contents in roots of wild Ipecac (Psychotria ipecacuanha). Biochem. Syst. Ecol., 2005, 33, 233-243.
[http://dx.doi.org/10.1016/j.bse.2004.08.005]
[11]
Lee, M.R. Ipecacuanha: the South American vomiting root. J. R. Coll. Physicians Edinb., 2008, 38(4), 355-360.
[PMID: 19227966]
[12]
Itoh, A.; Ikuta, Y.; Baba, Y.; Tanahashi, T.; Nagakura, N. Ipecac alkaloids from Cephaelis acuminata. Phytochemistry, 1999, 52(6), 1169-1176.
[http://dx.doi.org/10.1016/S0031-9422(99)00361-1] [PMID: 10643674]
[13]
de Oliveira, L.O.; Rossi, A.A.B.; Martins, E.R.; Batista, F.R.D.C.; Silva, R.S. Molecular phylogeography of Carapichea ipecacuanha, an amphitropical shrub that occurs in the understory of both semideciduous and evergreen forests. Mol. Ecol., 2010, 19(7), 1410-1422.
[http://dx.doi.org/10.1111/j.1365-294X.2010.04591.x] [PMID: 20298468]
[14]
Kornpointner, C.; Berger, A.; Fischer, I.M.; Popl, L.; Groher, C.; Valant-Vetschera, K. Revisiting Costa Rican Carapichea affinis (Rubiaceae: Palicoureeae): A source of bioactive dopamine-iridoid alkaloids. Phytochem. Lett., 2018, 26, 164-169.
[http://dx.doi.org/10.1016/j.phytol.2018.05.004]
[15]
Berger, A.; Fasshuber, H.; Schinnerl, J.; Robien, W.; Brecker, L.; Valant-Vetschera, K. Iridoids as chemical markers of false ipecac (Ronabea emetica), a previously confused medicinal plant. J. Ethnopharmacol., 2011, 138(3), 756-761.
[http://dx.doi.org/10.1016/j.jep.2011.10.024] [PMID: 22041104]
[16]
Manno, B.R.; Manno, J.E. Toxicology of ipecac: A review. Clin. Toxicol., 1977, 10(2), 221-242.
[http://dx.doi.org/10.3109/15563657708987968] [PMID: 15766]
[17]
Qing, Z-X.; Yang, P.; Tang, Q.; Cheng, P.; Liu, X-B.; Zheng, Y. Isoquinoline alkaloids and their antiviral, antibacterial, and antifungal activities and structure-activity relationship. Curr. Org. Chem., 2017, 21.
[http://dx.doi.org/10.2174/1385272821666170207114214]
[18]
Asano, T.; Sadakane, C.; Ishihara, K.; Yanagisawa, T.; Kimura, M.; Kamei, H. High-performance liquid chromatographic assay with fluorescence detection for the determination of cephaeline and emetine in human plasma and urine. J. Chromatogr. B Biomed. Sci. Appl., 2001, 757(2), 197-206.
[http://dx.doi.org/10.1016/S0378-4347(01)00170-0] [PMID: 11417863]
[19]
Syrup of Ipecac Still Number One Choice. Am. Pharm., 1981, 21, 46.
[20]
Fisher, H.H. Origin and uses of ipecac. Econ. Bot., 1973, 27, 231-234.
[http://dx.doi.org/10.1007/BF02872992]
[21]
Qing, Z-X.; Huang, J-L.; Yang, X-Y.; Liu, J-H.; Cao, H-L.; Xiang, F.; Cheng, P.; Zeng, J.G. Anticancer and reversing multidrug resistance activities of natural isoquinoline alkaloids and their structure-activity relationship. Curr. Med. Chem., 2018, 25(38), 5088-5114.
[http://dx.doi.org/10.2174/0929867324666170920125135] [PMID: 28933285]
[22]
Mishra, B.B.; Kale, R.R.; Singh, R.K.; Tiwari, V.K. Alkaloids: Future prospective to combat leishmaniasis. Fitoterapia, 2009, 80(2), 81-90.
[http://dx.doi.org/10.1016/j.fitote.2008.10.009] [PMID: 19015012]
[23]
Freitas, C.S.; Baggio, C.H.; Mayer, B.; dos Santos, A.C.; Twardowschy, A.; Santos, C.A.; Marques, M.C. Inhibition of gastric H+, K(+)-ATPase activity by compounds from medicinal plants. Nat. Prod. Commun., 2011, 6(9), 1253-1254.
[http://dx.doi.org/10.1177/1934578X1100600911] [PMID: 21941891]
[24]
Yang, S.; Xu, M.; Lee, E.M.; Gorshkov, K.; Shiryaev, S.A.; He, S.; Sun, W.; Cheng, Y.S.; Hu, X.; Tharappel, A.M.; Lu, B.; Pinto, A.; Farhy, C.; Huang, C.T.; Zhang, Z.; Zhu, W.; Wu, Y.; Zhou, Y.; Song, G.; Zhu, H.; Shamim, K.; Martínez-Romero, C.; García-Sastre, A.; Preston, R.A.; Jayaweera, D.T.; Huang, R.; Huang, W.; Xia, M.; Simeonov, A.; Ming, G.; Qiu, X.; Terskikh, A.V.; Tang, H.; Song, H.; Zheng, W. Emetine inhibits Zika and Ebola virus infections through two molecular mechanisms: Inhibiting viral replication and decreasing viral entry. Cell Discov., 2018, 4, 31.
[http://dx.doi.org/10.1038/s41421-018-0034-1] [PMID: 29872540]
[25]
Kratz, J.M.; Mair, C.E.; Oettl, S.K.; Saxena, P.; Scheel, O.; Schuster, D.; Hering, S.; Rollinger, J.M. hERG channel blocking ipecac alkaloids identified by combined in silico-In vitro screening. Planta Med., 2016, 82(11-12), 1009-1015.
[http://dx.doi.org/10.1055/s-0042-105572] [PMID: 27145237]
[26]
Muhammad, I.; Dunbar, D.C.; Khan, S.I.; Tekwani, B.L.; Bedir, E.; Takamatsu, S.; Ferreira, D.; Walker, L.A. Antiparasitic alkaloids from Psychotria klugii. J. Nat. Prod., 2003, 66(7), 962-967.
[http://dx.doi.org/10.1021/np030086k] [PMID: 12880315]
[27]
Hasegawa, M.; Sasaki, T.; Sadakane, K.; Tabuchi, M.; Takeda, Y.; Kimura, M.; Fujii, Y. Studies for the emetic mechanisms of ipecac syrup (TJN-119) and its active components in ferrets: Involvement of 5-hydroxytryptamine receptors. Jpn. J. Pharmacol., 2002, 89(2), 113-119.
[http://dx.doi.org/10.1254/jjp.89.113] [PMID: 12120752]
[28]
Endo, T.; Nemoto, M.; Ogawa, T.; Tamakai, H.; Hamaue, N.; Hirafuji, M.; Takeda, Y.; Hasegawa, M.; Fugii, Y.; Minami, M. Pharmacological aspects of ipecac syrup (TJN-119)-induced emesis in ferrets. Res. Commun. Mol. Pathol. Pharmacol., 2000, 108(3-4), 187-200.
[PMID: 11913711]
[29]
Adeyemi, O.S.; Awakan, O.J.; Adeyanju, A.A.; Otohinoyi, D.A. Cytotoxic and apoptotic action of nonactin and cephaeline. HBr precludes alteration of redox status. Nat. Prod. J., 2019, 9, 295-302.
[http://dx.doi.org/10.2174/2210315508666181010143636]
[30]
Asano, T.; Watanabe, J.; Sadakane, C.; Ishihara, K.; Hirakura, K.; Wakui, Y.; Yanagisawa, T.; Kimura, M.; Kamei, H.; Yoshida, T.; Fujii, Y.; Yamashita, M. Biotransformation of the ipecac alkaloids cephaeline and emetine from ipecac syrup in rats. Eur. J. Drug Metab. Pharmacokinet., 2002, 27(1), 29-35.
[http://dx.doi.org/10.1007/BF03190402] [PMID: 11996324]
[31]
Moran, D.M.; Crouch, D.J.; Finkle, B.S. Absorption of ipecac alkaloids in emergency patients. Ann. Emerg. Med., 1984, 13(12), 1100-1102.
[http://dx.doi.org/10.1016/S0196-0644(84)80332-7] [PMID: 6150666]
[32]
Yamashita, M.; Yamashita, M.; Azuma, J. Urinary excretion of ipecac alkaloids in human volunteers. Vet. Hum. Toxicol., 2002, 44(5), 257-259.
[PMID: 12361104]
[33]
Asano, T.; Ishihara, K.; Wakui, Y.; Yanagisawa, T.; Kimura, M.; Kamei, H.; Yoshida, T.; Kuroiwa, Y.; Fujii, Y.; Yamashita, M.; Kuramochi, T.; Tomisawa, H.; Tateishi, M. Absorption, distribution and excretion of 3H-labeled cephaeline- and emetine-spiked ipecac syrup in rats. Eur. J. Drug Metab. Pharmacokinet., 2002, 27(1), 17-27.
[http://dx.doi.org/10.1007/BF03190401] [PMID: 11996323]
[34]
Scharman, E.J.; Hutzler, J.M.; Rosencrance, J.G.; Tracy, T.S. Single dose pharmacokinetics of syrup of ipecac. Ther. Drug Monit., 2000, 22(5), 566-573.
[http://dx.doi.org/10.1097/00007691-200010000-00011] [PMID: 11034262]
[35]
Teshima, D.; Suzuki, A.; Otsubo, K.; Higuchi, S.; Aoyama, T.; Shimozono, Y.; Saita, M.; Noda, K. Efficacy of emetic and United State pharmacopoeia ipecac syrup in prevention of drug absorption. Chem. Pharm. Bull. (Tokyo), 1990, 38(8), 2242-2245.
[http://dx.doi.org/10.1248/cpb.38.2242] [PMID: 1980639]
[36]
Asano, T.; Kushida, H.; Sadakane, C.; Ishihara, K.; Wakui, Y.; Yanagisawa, T.; Kimura, M.; Kamei, H.; Yoshida, T. Metabolism of ipecac alkaloids cephaeline and emetine by human hepatic microsomal cytochrome P450s, and their inhibitory effects on P450 enzyme activities. Biol. Pharm. Bull., 2001, 24(6), 678-682.
[http://dx.doi.org/10.1248/bpb.24.678] [PMID: 11411558]
[37]
Yoshimatsu, K.; Shimomura, K.; Yamazaki, M.; Saito, K.; Kiuchi, F. Transformation of ipecac (Cephaelis ipecacuanha) with Agrobacterium rhizogenes. Planta Med., 2003, 69(11), 1018-1023.
[http://dx.doi.org/10.1055/s-2003-45149] [PMID: 14735440]
[38]
Yoshimatsu, K.; Shimomura, K. Efficient shoot formation on internodal segments and alkaloid formation in the regenerates of Cephaelis ipecacuanha A. Richard. Plant Cell Rep., 1991, 9(10), 567-570.
[http://dx.doi.org/10.1007/BF00232333] [PMID: 24220713]
[39]
Teshima, D.; Ikeda, K.; Satake, M.; Aoyama, T.; Shimomura, K. Production of emetic alkaloid by in vitro culture of Cephaelis ipecacuanha A. Richard. Plant Cell Rep., 1988, 7(4), 278-280.
[http://dx.doi.org/10.1007/BF00272542] [PMID: 24241766]
[40]
Xun, Z.; Liu, D.; Huang, R.; He, S.; Hu, D.; Guo, X.; Xian, Y. Simultaneous determination of eight alkaloids and oleandrin in herbal cosmetics by dispersive solid-phase extraction coupled with ultra-high performance liquid chromatography and tandem mass spectrometry. J. Sep. Sci., 2017, 40(9), 1966-1973.
[http://dx.doi.org/10.1002/jssc.201601427] [PMID: 28317265]
[41]
Lei, S. Rapid detection of alkaloids in ipecac by direct analysis in real time tandem mass spectrometry (DART-MS/MS). China J. Chinese Mater. Medica, 2012, 37(10), 1426-130.
[http://dx.doi.org/10.4268/cjcmm20121017]
[42]
Zhang, W.; Bah, J.; Wohlfarth, A.; Franzén, J. A stereodivergent strategy for the preparation of corynantheine and ipecac alkaloids, their epimers, and analogues: efficient total synthesis of (-)-dihydrocorynantheol, (-)-corynantheol, (-)-protoemetinol, (-)-corynantheal, (-)-protoemetine, and related natural and nonnatural compounds. Chemistry, 2011, 17(49), 13814-13824.
[http://dx.doi.org/10.1002/chem.201102012] [PMID: 22052788]
[43]
Itoh, A.; Ikuta, Y.; Tanahashi, T.; Nagakura, N. Two alangium alkaloids from Alangium lamarckii. J. Nat. Prod., 2000, 63(5), 723-725.
[http://dx.doi.org/10.1021/np0000163] [PMID: 10843602]
[44]
Elvidge, D.A.; Johnson, G.W.; Harrison, J.R. Selective, stability-indicating assay of the major ipecacuanha alkaloids, emetine and cephaeline, in pharmaceutical preparations by high-performance liquid chromatography using spectrofluorimetric detection. J. Chromatogr. A, 1989, 463(1), 107-118.
[http://dx.doi.org/10.1016/S0021-9673(01)84457-5] [PMID: 2715231]
[45]
Crouch, D.J.; Moran, D.M.; Finkle, B.S.; Peat, M.A. Quantitative analysis of emetine and cephaeline by reversed-phase high performance liquid chromatography with fluorescence detection. J. Anal. Toxicol., 1984, 8(2), 63-65.
[http://dx.doi.org/10.1093/jat/8.2.63] [PMID: 6716976]
[46]
Davidson, A.G.; Hassan, S.M. The simultaneous assay of emetine and cephaeline in ipecacuanha and its preparations by spectrofluorimetry. J. Pharm. Biomed. Anal., 1984, 2(3-4), 441-448.
[http://dx.doi.org/10.1016/0731-7085(84)80047-3] [PMID: 16867724]
[47]
Frei, R.W.; Santi, W.; Thomas, M. Liquid chromatography of dansyl derivatives of some alkaloids and the application to the analysis of pharmaceuticals. J. Chromatogr. A, 1976, 116(2), 365-377.
[http://dx.doi.org/10.1016/S0021-9673(00)89907-0] [PMID: 1245578]
[48]
Chakraborty, M.; Mukhopadhyay, S. Angustinine-A new benzopyridoquinolizine alkaloid from Alangium lamarckii. Nat. Prod. Commun., 2012, 7(9), 1169-1170.
[http://dx.doi.org/10.1177/1934578X1200700915] [PMID: 23074898]
[49]
Jha, S.; Jha, T.B. Micropropagation of Cephaelis ipecacuanha rich. Plant Cell Rep., 1989, 8(8), 437-439.
[http://dx.doi.org/10.1007/BF00269043] [PMID: 24233523]
[50]
Cheong, B.E.; Takemura, T.; Yoshimatsu, K.; Sato, F. Molecular cloning of an O-methyltransferase from adventitious roots of Carapichea ipecacuanha. Biosci. Biotechnol. Biochem., 2011, 75(1), 107-113.
[http://dx.doi.org/10.1271/bbb.100605] [PMID: 21228475]
[51]
Nomura, T.; Kutchan, T.M. Three new O-methyltransferases are sufficient for all O-methylation reactions of ipecac alkaloid biosynthesis in root culture of Psychotria ipecacuanha. J. Biol. Chem., 2010, 285(10), 7722-7738.
[http://dx.doi.org/10.1074/jbc.M109.086157] [PMID: 20061395]

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