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Combinatorial Chemistry & High Throughput Screening

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ISSN (Print): 1386-2073
ISSN (Online): 1875-5402

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Mini-Review Article

Peganum harmala L.: A Review of Botany, Traditional Use, Phytochemistry, Pharmacology, Quality Marker, and Toxicity

Author(s): Ling-Na Li*

Volume 27, Issue 6, 2024

Published on: 17 July, 2023

Page: [797 - 822] Pages: 26

DOI: 10.2174/1386207326666230622164243

Price: $65

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Abstract

Background: Peganum harmala L. is a perennial herb of Peganum in Zygophyllaceae family. It has been used as a national medicinal herb with the efficacy of strengthening muscle, warming stomach, dispelling cold, and removing dampness in Chinese folk. Clinically, it is mainly used to treat diseases such as weak muscles and veins, joint pain, cough and phlegm, dizziness, headache, and irregular menstruation.

Methods: The relevant information about P. harmala L. in this review is based on online databases, including Elsevier, Willy, Web of Science, PubMed, ScienceDirect, SciFinder, SpringLink, Google Scholar, Baidu Scholar, ACS publications, SciHub, Scopus, and CNKI. The other information was acquired from ancient books and classical works about P. harmala L.

Results: P. harmala L. is an important medicinal plant with a variety of traditional uses according to the theory of Chinese medicine. Phytochemical research revealed that P. harmala L. contained alkaloids, volatile oils, flavonoids, triterpenoids, coumarins, lignins, anthraquinones. Modern studies showed P. harmala L. possessed multiple bioactivities, including anti-cancer, neuroprotective, anti-bacterial, anti-inflammatory, hypoglycemic, anti-hypertensive, anti-asthmatic, and insecticidal activities. Furthermore, the contents of the quality marker and toxicity of P. harmala L. were summarized and analyzed in this review.

Conclusion: The botany, traditional use, phytochemistry, pharmacology, quality marker, and toxicity of P. harmala L. were reviewed in this paper. It will not only provide an important clue for further studying P. harmala L., but also supply an important theoretical basis and valuable reference for in-depth research and exploitations of this plant in the future.

Keywords: Peganum harmala L., botany, traditional use, phytochemistry, pharmacology, quality marker, toxicity.

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[1]
Li, H.; Shi, K.H.; Wu, K.X.; Zhou, J.H.; Mao, G.G.M. Research progress in chemical constituents, pharmacological effects and toxicity of Peganum harmala L. Zhongchengyao, 2022, 44, 3936-3943.
[2]
Moustafa, N.E.; Alomari, A.A. Green synthesis and bactericidal activities of isotropic and anisotropic spherical gold nanoparticles produced using Peganum harmala L leaf and seed extracts. Biotechnol. Appl. Biochem., 2019, 66(4), 664-672.
[http://dx.doi.org/10.1002/bab.1782] [PMID: 31141208]
[3]
Wang, N.N.; Wu, Y.Y.; Yang, Z.G. Research progress of Peganum harmala L. and prediction and analysis of quality markers. Zhong Yao Cai, 2022, 45, 1532-1537.
[4]
Wang, J.L.; Wei, L.; Bao, H.Q. Research progress in pharmacological mechanism of anti-inflammatory and immune regulation of alkaloids from Peganum harmala L. Shanghai J. Tradit. Chin. Med., 2019, 53, 97-100.
[5]
Javad, S.R.; Cristina, Q.; Jesus, H.B.; Prabhakar, S.; Sakshi, P.; Beraat, O.; Furkan, E.H.; Shabnum, S.; Surjit, S.; Krishnendu, A.; Marjan, A.; Carla, M.S.C.; Maria, D.L.; Mauricio, S.; Miquel, M.; Tamar, G.; Ahmed, A.H.; Ahmed, A.R.; Manoj, K.; Hafiz, A.R.S.; William, C.C. Peganum spp.: A comprehensive review on bioactivities and health-enhancing effects and their potential for the formulation of functional foods and pharmaceutical drugs. Oxid. Med. Cell. Longev., 2021, 2021, 5900422.
[6]
Cheng, L.; Chen, J.X.; Li, Y.L.; Wang, Y.G.; Zhou, Y.T.; Zhang, Y.Y. Diversity of bacterial communities in rhizosphere soil of Peganum harmala L. in desert steppe. Ganhanqu Yanjiu, 2018, 35, 977-983.
[7]
Guo, X.X.; Yue, P.; Li, X.Y.; Qiao, J.J.; Hu, Y.; Zuo, X.A. Effect of precipitation on above ground biomass of Peganum harmala L. in desert grassland. J. Desert Res., 2022, 42, 164-172.
[8]
Niroumand, M.C.; Farzaei, M.H.; Amin, G. Medicinal properties of Peganum harmala L. in traditional Iranian medicine and modern phytotherapy: A review. J. Tradit. Chin. Med., 2015, 35(1), 104-109.
[http://dx.doi.org/10.1016/S0254-6272(15)30016-9] [PMID: 25842736]
[9]
Zhang, K.X.; Bao, F.; Yang, Z.G. Medicinal plant resources in Pakistan. Asia-Pacific Tradit. Med., 2019, 15, 1-8.
[10]
Zhao, T.; Wang, C.H.; Wang, Z.T. Research progress on chemical constituents and pharmacological activities of alkaloids from Peganum harmala L. J. Int. Pharm. Res, 2010, 37, 333-339.
[11]
Wang, N.N.; Wei, G.H.; Zhang, Z.J.; Fang, J.G. Chemical constituents in Pegannum harmala L. based on UHPLC-QTOF-MS/MS and its neuroprotective activities. Chin. Tradit. Herbal Drugs, 2022, 53, 1688-1696.
[12]
Khashimov, K.N.; Telezhenetskaya, M.V.; Rashkes, Y.V.; Yunusov, S.Y. Pegamine: A new alkaloid fromPeganum harmala. Chem. Nat. Compd., 1970, 6(4), 462-464.
[http://dx.doi.org/10.1007/BF00564251]
[13]
Yan, P.S.; Song, Y.; Sakuno, E.; Nakajima, H.; Nakagawa, H.; Yabe, K. Cyclo(L-leucyl-L-prolyl) produced by Achromobacter xylosoxidans inhibits aflatoxin production by Aspergillus parasiticus. Appl. Environ. Microbiol., 2004, 70(12), 7466-7473.
[http://dx.doi.org/10.1128/AEM.70.12.7466-7473.2004] [PMID: 15574949]
[14]
Harwood, D.T. Urban, S.; Blunt, J.W.; Munro, M.H.G. β-carboline alkaloids from a New Zealand marine bryozoan, Cribricellina cribraria. Nat. Prod. Res., 2003, 17(1), 15-19.
[http://dx.doi.org/10.1080/1057563021000001063] [PMID: 12674137]
[15]
Plugar, V.N.; Abdullaev, N.D.; Rashkes, Y.V.; Yagudaev, M.R.; Tulyaganov, N. Structure of the products of the metabolism of deoxypeganine and of deoxyvasicinone. Chem. Nat. Compd., 1983, 19(6), 720-727.
[http://dx.doi.org/10.1007/BF00575179]
[16]
Zheng, X.; Zhang, Z.; Chou, G.; Wu, T.; Cheng, X.; Wang, C.; Wang, Z. Acetylcholinesterase inhibitive activity-guided isolation of two new alkaloids from seeds of Peganum nigellastrum Bunge by an In vitro TLC- bioautographic assay. Arch. Pharm. Res., 2009, 32(9), 1245-1251.
[http://dx.doi.org/10.1007/s12272-009-1910-x] [PMID: 19784581]
[17]
Werstiuk, N.H.; Ju, C. Protium-deuterium exchange of substituted pyridines in neutral D2O at elevated temperatures. ChemInform, 1989, 20(25), 94.
[http://dx.doi.org/10.1002/chin.198925094]
[18]
Tao, M.H.; Chen, Y.C.; Wei, X.Y.; Tan, J.W.; Zhang, W.M. Chemical constituents of the endophytic fungus phomopsissp. A240 isolated from Taxus chinensisvar. mairei. Helv. Chim. Acta, 2014, 97(3), 426-430.
[http://dx.doi.org/10.1002/hlca.201300367]
[19]
Yang, Y.; Cheng, X.; Liu, W.; Han, Z.; Chou, G.; Wang, Y.; Sun, D.; Wang, Z.; Wang, C. Peganumine B-I and two enantiomers: New alkaloids from the seeds of Peganum harmala Linn. and their potential cytotoxicity and cholinesterase inhibitory activities. RSC Advances, 2016, 6(19), 15976-15987.
[http://dx.doi.org/10.1039/C6RA00086J]
[20]
Dobronravova, E.K.; Telezhenetskaya, M.V.; Shakirov, T.T. A polarographic investigation of the alkaloids of Peganum harmala. Chem. Nat. Compd., 1976, 12(3), 316-317.
[http://dx.doi.org/10.1007/BF00567805]
[21]
Sassoui, D.; Seridi, R.; Azin, K.; Usai, M. Evaluation of phytochemical constituents by GC-MS and antidepressant activity of Peganum harmala L. seeds extract. Asian Pac. J. Trop. Dis., 2015, 5(12), 971-974.
[http://dx.doi.org/10.1016/S2222-1808(15)60967-7]
[22]
Subba Reddy, B.V.; Venkateswarlu, A.; Madan, C.; Vinu, A. Cellulose-SO3H: An efficient and biodegradable solid acid for the synthesis of quinazolin-4(1H)-ones. Tetrahedron Lett., 2011, 52(16), 1891-1894.
[http://dx.doi.org/10.1016/j.tetlet.2011.02.030]
[23]
Shakhidoyatov, K.M.; Barakat, Y.; Levkovich, M.G.; Abdullaev, N.D. 1-Acyl-and 1,2-dihydro-1H(acyl)deoxyvasicinones. Synthesis and chemical transformations. Chem. Nat. Compd., 2007, 43(4), 429-436.
[http://dx.doi.org/10.1007/s10600-007-0155-5]
[24]
Baker, B.R.; Almaula, P.I. Nonclassical antimetabolites. X. 1,2 a facile synthesis of 4-quinazolone-2-carboxylic acid and the structure of bogert’s ammonium salt. J. Org. Chem., 1962, 27(12), 4672-4674.
[http://dx.doi.org/10.1021/jo01059a524]
[25]
Balsells, R.E.; Frasca, A.R. Photochemical dimerization of β-carboline alkaloids. Tetrahedron, 1983, 39(1), 33-39.
[http://dx.doi.org/10.1016/S0040-4020(01)97626-4]
[26]
Siddiqui, S.; Yusuf Khan, O.; Faizi, S.; Shaheen Siddiqui, B. Studies in the chemical constituents of the seeds of Peganum harmala: Isolation and structure elucidation of two β-carboline lactams-harmalanine and harmalacidine. Heterocycles, 1988, 27(6), 1401-1410.
[http://dx.doi.org/10.3987/COM-88-4490]
[27]
Begum, S.; Zubair, F.; Nawazish Ali, S.; Shaheen Siddiqui, B. An efficient, mild and solvent-free synthesis of benzene ring acylated harmalines. Molecules, 2009, 15(1), 68-82.
[http://dx.doi.org/10.3390/molecules15010068] [PMID: 20110872]
[28]
Duan, J.D.; Che, Z.T.; Zhou, R.H.; Zhao, S.X.; Wang, M.S. Studies on the chemical constituents of Peganum multisectum Maxim II.flavonoids and alkaloids from aerial part of plant. Zhongguo Yaoke Daxue Xuebao, 1998, 29, 100-104.
[29]
Hashimoto, Y.; Kawanishi, K. New organic bases from amazonian Banisteriopsis caapi. Phytochemistry, 1975, 14(7), 1633-1635.
[http://dx.doi.org/10.1016/0031-9422(75)85365-9]
[30]
Yang, Y.; Cheng, X.; Liu, W.; Chou, G.; Wang, Z.; Wang, C. Potent AChE and BChE inhibitors isolated from seeds of Peganum harmala Linn by a bioassay-guided fractionation. J. Ethnopharmacol., 2015, 168, 279-286.
[http://dx.doi.org/10.1016/j.jep.2015.03.070] [PMID: 25862961]
[31]
Jyothi, P.; Yellamma, K. Molecular docking studies on the therapeutic targets of Alzheimer disease (AChE and BChE) using natural bioactive alkaloids. Int. J. Pharm. Pharm. Sci., 2016, 8(12), 108-112.
[http://dx.doi.org/10.22159/ijpps.2016v8i12.14833]
[32]
Zhang, Q.; Zan, Y.H.; Yang, H.G.; Yang, M.Y.; Liu, F.S.; Li, S.G.; Peng, X.H.; Lin, B.; Li, Z.L.; Li, D.H.; Hua, H.M. Anti-tumor alkaloids from Peganum harmala. Phytochemistry, 2022, 197, 113107.
[http://dx.doi.org/10.1016/j.phytochem.2022.113107] [PMID: 35121215]
[33]
Nomura, T.; Ma, Z-Z.; Hano, Y.; Chen, Y.J. Two new quinazoline-quinoline alkaloids from Peganum nigellastrum. Heterocycles, 1999, 51(8), 1883-1889.
[http://dx.doi.org/10.3987/COM-99-8595]
[34]
Ma, Z.; Hano, Y.; Nomura, T.; Chen, Y. Novel quinazoline–quinoline alkaloids with cytotoxic and DNA topoisomerase II inhibitory activities. Bioorg. Med. Chem. Lett., 2004, 14(5), 1193-1196.
[http://dx.doi.org/10.1016/j.bmcl.2003.12.048] [PMID: 14980663]
[35]
Sultana, N.; Anwar, M.A.; Ali, Y.; Afza, N. Phytochemical studies on Adhatoda vasica. Pak. J. Sci. Ind. Res., 2005, 48, 249-256.
[36]
Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L.; Pace, P. Palladium-catalysed hydroarylation and hydrovinylation of 3,3-dialkoxy-1-aryl-1-propynes. An approach to 3-aryl- and 3-vinylquinolines. Tetrahedron, 1996, 52(30), 10225-10240.
[http://dx.doi.org/10.1016/0040-4020(96)00557-1]
[37]
Joshi, G.; Wani, A.A.; Sharma, S.; Bhutani, P.; Bharatam, P.V.; Paul, A.T.; Kumar, R. Unanticipated cleavage of 2-nitrophenyl-substituted N-formyl pyrazolines under Bechamp conditions: Unveiling the synthesis of 2-aryl quinolines and their mechanistic exploration via DFT studies. ACS Omega, 2018, 3(12), 18783-18790.
[http://dx.doi.org/10.1021/acsomega.8b02682] [PMID: 31458441]
[38]
Corbally, R.P.; Mehta, L.K.; Parrick, J.; Short, E.L. Experimental and calculated13C chemical shifts for α-, β-, γ- and δ-carbolines. Magn. Reson. Chem., 2000, 38(12), 1034-1036.
[http://dx.doi.org/10.1002/1097-458X(200012)38:12<1034:AID-MRC783>3.0.CO;2-M]
[39]
Anouhe, J.B.S.; Adima, A.A.; Niamké, F.B.; Stien, D.; Amian, B.K.; Blandinières, P.A.; Virieux, D.; Pirat, J.L.; Kati-Coulibaly, S.; Amusant, N. Dicorynamine and harmalan-N-oxide, two new β-carboline alkaloids from Dicorynia guianensis Amsh heartwood. Phytochem. Lett., 2015, 12, 158-163.
[http://dx.doi.org/10.1016/j.phytol.2015.03.012]
[40]
Dassonneville, B.; Witulski, B.; Detert, H. Cycloadditions of alkynylynamides-a total synthesis of perlolyrine and the first total synthesis of “Isoperlolyrine”. Eur. J. Org. Chem., 2011, 2011(15), 2836-2844.
[http://dx.doi.org/10.1002/ejoc.201100121]
[41]
Wang, X.; Geng, Y.; Wang, D.; Shi, X.; Liu, J. Separation and purification of harmine and harmaline from Peganum harmala using pH-zone-refining counter-current chromatography. J. Sep. Sci., 2008, 31(20), 3543-3547.
[http://dx.doi.org/10.1002/jssc.200800322] [PMID: 18844206]
[42]
Li, K.; Fu, X.; Zhao, Y.; Gao, W.; Li, Y. A facile synthesis of novel pyrrolo[3,4-b]quinolin-1-one derivatives. Res. Chem. Intermed., 2016, 42(5), 4273-4287.
[http://dx.doi.org/10.1007/s11164-015-2273-1]
[43]
Gao, J.; Zhang, Y.L.; Miao, X.Z.; Zhang, X.; Yuan, J.; Wang, J.L.; Zhen, C.M.; Liu, Y.G.; Tan, P. Identification of alkaloids in seeds of Peganumharmala Linn and analysis of their fragmentation pathways by LTQ-Qrobitrap MS. J. Chin. Mass Spectrom. Soc., 2017, 38, 89-96.
[44]
Huang, W.P.; Liu, J.L.; Wang, C.L. Progress in the synthesis of natural product luotonin A and its derivatives. Youji Huaxue, 2009, 29, 1533-1543.
[45]
Zhao, T.; Wang, C.H.; Wang, Z.T. Research progress on alkaloids and pharmacological activities of Peganum plants. J. Int. Pharm. Res., 2010, 37, 333-339.
[46]
Wang, K.B.; Li, D.H.; Bao, Y.; Cao, F.; Wang, W.J.; Lin, C.; Bin, W.; Bai, J.; Pei, Y.H.; Jing, Y.K.; Yang, D.; Li, Z.L.; Hua, H.M. Structurally diverse alkaloids from the seeds of Peganum harmala. J. Nat. Prod., 2017, 80(2), 551-559.
[http://dx.doi.org/10.1021/acs.jnatprod.6b01146] [PMID: 28128938]
[47]
Wang, C.; Zhang, Z.; Wang, Y.; He, X. Cytotoxic indole alkaloids against human leukemia cell lines from the toxic plant Peganum harmala. Toxins, 2015, 7(11), 4507-4518.
[http://dx.doi.org/10.3390/toxins7114507] [PMID: 26540074]
[48]
Wang, K.B.; Hu, X.; Li, S.G.; Li, X.Y.; Li, D.H.; Bai, J.; Pei, Y.H.; Li, Z.L.; Hua, H.M. Racemic indole alkaloids from the seeds of Peganum harmala. Fitoterapia, 2018, 125, 155-160.
[http://dx.doi.org/10.1016/j.fitote.2018.01.008] [PMID: 29355750]
[49]
Zhu, Z.; Zhao, S.; Wang, C. Antibacterial, antifungal, antiviral, and antiparasitic activities of Peganum harmala and its ingredients: A review. Molecules, 2022, 27(13), 4161.
[http://dx.doi.org/10.3390/molecules27134161] [PMID: 35807407]
[50]
Moloudizargari, M.; Mikaili, P.; Aghajanshakeri, S.; Asghari, M.; Shayegh, J. Pharmacological and therapeutic effects of Peganum harmala and its main alkaloids. Pharmacogn. Rev., 2013, 7(14), 199-212.
[http://dx.doi.org/10.4103/0973-7847.120524] [PMID: 24347928]
[51]
Monsef, H.R.; Ghobadi, A.; Iranshahi, M.; Abdollahi, M. Antinociceptive effects of Peganum harmala L. alkaloid extract on mouse formalin test. J. Pharm. Pharm. Sci., 2004, 7(1), 65-69.
[PMID: 15144736]
[52]
Jalali, A.; Dabaghian, F.; Zarshenas, M.M. Alkaloids of Peganum harmala: Anticancer biomarkers with promising outcomes. Curr. Pharm. Des., 2021, 27(2), 185-196.
[http://dx.doi.org/10.2174/18734286MTExhODEu4] [PMID: 33238864]
[53]
Apostolico, I.; Aliberti, L.; Caputo, L.; De Feo, V.; Fratianni, F.; Nazzaro, F.; Souza, L.; Khadhr, M. Chemical composition, antibacterial and phytotoxic activities of Peganum harmala seed essential oils from five different localities in Northern Africa. Molecules, 2016, 21(9), 1235.
[http://dx.doi.org/10.3390/molecules21091235] [PMID: 27649128]
[54]
Li, S.; Cheng, X.; Wang, C. A review on traditional uses, phytochemistry, pharmacology, pharmacokinetics and toxicology of the genus Peganum. J. Ethnopharmacol., 2017, 203, 127-162.
[http://dx.doi.org/10.1016/j.jep.2017.03.049] [PMID: 28359849]
[55]
Şanli, A.; Karadoğan, T. Geographical impact on essential of endemic Kundmannia anatolica Hub.-Mor. (Apiaceae). Afr. J. Tradit. Complement. Altern. Med., 2016, 14(1), 131-137.
[http://dx.doi.org/10.21010/ajtcam.v14i1.14] [PMID: 28480390]
[56]
Gioffrè, G.; Ursino, D.; Labate, M.L.C.; Giuffrè, A.M. The peel essential oil composition of bergamot fruit (Citrus bergamia, Risso) of Reggio Calabria (Italy): A review. Emir. J. Food Agric., 2020, 32, 835-845.
[http://dx.doi.org/10.9755/ejfa.2020.v32.i11.2197]
[57]
Giuffre, A.; Nobile, R. Citrus bergamia, Risso: The peel, the juice and the seed oil of the bergamot fruit of Reggio Calabria (South Italy). Emir. J. Food Agric., 2020, 32, 522-532.
[58]
Chatterjee, S.; Gupta, S.; Variyar, P.S. Comparison of essential oils obtained from different extraction techniques as an aid in identifying aroma significant compounds of nutmeg (Myristica fragrans). Nat. Prod. Commun., 2015, 10(8), 1934578X1501000.
[http://dx.doi.org/10.1177/1934578X1501000833] [PMID: 26434138]
[59]
Yang, G.; Liao, Z.; Xu, Z.; Zhang, H.; Chen, D. Antimitotic and antifungal C-3/C-3′'-biflavanones from Stellera chamaejasme. Chem. Pharm. Bull., 2005, 53(7), 776-779.
[http://dx.doi.org/10.1248/cpb.53.776] [PMID: 15997133]
[60]
Sharaf, M.; El-Ansari, M.A.; Matlin, S.A.; Saleh, N.A.M. Four flavonoid glycosides from Peganum harmala. Phytochemistry, 1997, 44(3), 533-536.
[http://dx.doi.org/10.1016/S0031-9422(96)00531-6] [PMID: 9014375]
[61]
Avula, B.; Wang, Y.H.; Rumalla, C.S.; Smillie, T.J.; Khan, I.A. Simultaneous determination of alkaloids and flavonoids from aerial parts of Passiflora species and dietary supplements using UPLC-UV-MS and HPTLC. Nat. Prod. Commun., 2012, 7(9), 1934578X1200700.
[http://dx.doi.org/10.1177/1934578X1200700918] [PMID: 23074901]
[62]
Wang, C.; Zhang, Z.; Wang, Y.; He, X. Cytotoxic constituents and mechanism from Peganum harmala. Chem. Biodivers., 2016, 13(7), 961-968.
[http://dx.doi.org/10.1002/cbdv.201500384] [PMID: 27273342]
[63]
Li, H.; Wang, Z.; Wang, Y.; Xu, J.; He, X. Triterpenoids with anti-proliferative effects from the seeds of Peganum harmala L. Phytochemistry, 2020, 174, 112342.
[http://dx.doi.org/10.1016/j.phytochem.2020.112342] [PMID: 32172018]
[64]
Ma, Z.Z.; Hano, Y.; Qiu, F.; Shao, G.; Chen, Y.J.; Nomura, T. Triterpenoids from Peganum nigellastrum. J. Asian Nat. Prod. Res., 2007, 9(6), 575-578.
[http://dx.doi.org/10.1080/10286020701611636] [PMID: 17885848]
[65]
Ma, Z.Z.; Hano, Y.; Nomura, T.; Chen, Y.J. Three new triterpenoids from Peganum nigellastrum. J. Nat. Prod., 2000, 63(3), 390-392.
[http://dx.doi.org/10.1021/np990227b] [PMID: 10757727]
[66]
Reisch, J.; Rosenthal, B.H.W. Naturstoffchemie. 108. Mitt. Synthese des 7,7?-Oxy-dicumarins, dem moglichen Prakursor vom Lasioerin und Gnidicumarin. Monatsh. Chem., 1987, 118(6-7), 871-874.
[http://dx.doi.org/10.1007/BF00809238]
[67]
Heleno, V.C.G.; Silva, R.; Pedersoli, S.; Albuquerque, S.; Bastos, J.K.; Silva, M.L.A.; Donate, P.M.; Silva, G.V.J.; Lopes, J.L.C. Detailed 1H and 13C NMR structural assignment of three biologically active lignan lactones. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2006, 63(1), 234-239.
[http://dx.doi.org/10.1016/j.saa.2005.04.047] [PMID: 16344252]
[68]
Wu, M.; Tang, J.; Zhou, X.; Lei, D.; Zeng, C.; Ye, H.; Cai, T.; Zhang, Q. Isolation of dibutyl phthalate-degrading bacteria and its coculture with citrobacter freundii CD-9 to degrade fenvalerate. J. Microbiol. Biotechnol., 2022, 32(2), 176-186.
[http://dx.doi.org/10.4014/jmb.2110.10048] [PMID: 35058397]
[69]
Pitre, S.; Srivastava, S. Two new anthraquinones from the Seeds of Peganum harmala. Planta Med., 1987, 53(1), 106-107.
[http://dx.doi.org/10.1055/s-2006-962639] [PMID: 17268980]
[70]
Liu, W.; Wang, Y.; He, D.; Li, S.; Zhu, Y.; Jiang, B.; Cheng, X.; Wang, Z.; Wang, C. Antitussive, expectorant, and bronchodilating effects of quinazoline alkaloids (±)-vasicine, deoxyvasicine, and (±)-vasicinone from aerial parts of Peganum harmala L. Phytomedicine, 2015, 22(12), 1088-1095.
[http://dx.doi.org/10.1016/j.phymed.2015.08.005] [PMID: 26547531]
[71]
Mokhtar, M.M.; Shaban, H.M.; Hegazy, M.E.F.; Ali, S.S. Evaluating the potential cancer chemopreventive efficacy of two different solvent extracts of Seriphidium herba-alba In vitro. Bull. Fac. Pharm. Cairo Univ., 2017, 55(1), 195-201.
[http://dx.doi.org/10.1016/j.bfopcu.2017.03.002]
[72]
He, Z.Q.; Li, Y.H.; Zhang, J. Study on anti-cancer effect of harmine. Pract. Oncol. J., 2000, 14, 8-9.
[73]
Wang, M.L.; Niu, J.L.; Gao, Y.; Wang, Y.P.; Zhang, L.F.; Zhang, Y.; Wang, P. The Effect of dehydroharmaline on the proliferation, migration and invasion of MCF7 cells. Zhong Yao Cai, 2018, 41, 1702-1706.
[74]
Zhang, T.; Sun, W.H.; Jiang, S.Y.; Jing, X.X.; Zhang, W.W.; Yu, N.; Li, X.L.; Zhu, G.Q.; Zhou, Y.C.; Shao, Y. Study on the effects and mechanisms of harmine on proliferation and apoptosis of gastric cancer cells. Clin. J. Gastroenterol., 2018, 23, 221-225.
[75]
Liu, S.L. Inhibitory effect and molecular mechanism of harmine on cervical cancer. Master's Thesis Nanchang University, Nanchang., 2018.
[76]
Li, C. Study on mechanism of autophagy and apoptosis of human gastric cancer cells MGC-803 and SGC-7901 induced by dehydroharmine. Master's Thesis Guangdong Pharm. University, Guangzhou., 2017.
[77]
Li, H.Y.; Zhang, Z.S.; Wang, J. Camelbine affects the proliferation, apoptosis, migration, and invasion of ovarian cancer cell line CAOV3 through LOXL1-AS1. Chin. J. Cell Biol., 2021, 43, 385-393.
[78]
Xirenayi, X.R.P.; Lei, X.Y.; Zhang, Y.; Yiliyasi, A.S.; Mutalipu, A.M.T.; Chen, Q.; Feng, X.Z.; Li, F.; Mi, N. Effects of harmine hydrochloride on apoptosis and autophagy in human neuroblastoma SH-SY5Y cells. Chin. J. Pharm. Toxicol, 2020, 34, 825-831.
[79]
He, D.D.; Zhang, L.; Liu, L.; Wu, X.J.; Cheng, X.M.; Wang, C.H. The total alkaloids of Peganum harmala L. improve learning and memory ability in mice. Zhongchengyao, 2015, 37, 478-482.
[80]
Zhang, X.S.; Sun, J.N.; Yu, H.L. The effect of total alkaloids from Peganum harmala L. on learning and memory in vascular dementia rats. Zhong Yao Cai, 2015, 38(11), 2353-2357.
[PMID: 27356391]
[81]
Fu, J.R.; Teng, L.; Dai, X.Y.; Yu, F.S. Study on the extraction and purification process of total alkaloids from Peganum harmaceum and its effect on dementia mice induced by Aluminum. Zhongchengyao, 2011, 33, 975-979.
[82]
Lei, X.Y.; Yiliyasi, A.S.; Zhang, Y.; Chen, Q.; Feng, X.Z.; Xirenayi, X.R.P.; Mi, N. Degradation of Tau protein by total alkaloids of Peganum harmala L. Xinjiang Yike Daxue Xuebao, 2021, 44, 615-619.
[83]
Quan, Q.H.; Gao, Z.P.; Ji, R.F.; Yuan, J.; Wang, J.L.; Liu, Y.B.; Zhou, Y.; Guo, X.Y.; Zhang, J.M.; Liu, Y.G. Extraction of polysaccharides from Peganum harmala L. and its effect on the aggregation toxicity of polyglutamine in Cryptomeria elegans. J. Beijing Univ. Tradit. Chin. Med., 2017, 40, 954-959.
[84]
Herraiz, T. González, D.; Ancín-Azpilicueta, C.; Arán, V.J.; Guillén, H. β-Carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO). Food Chem. Toxicol., 2010, 48(3), 839-845.
[http://dx.doi.org/10.1016/j.fct.2009.12.019] [PMID: 20036304]
[85]
Saleem, A.; Engström, M.; Wurster, S.; Savola, J.M.; Pihlaja, K. Interaction of folk medicinal plant extracts with human alpha2-adrenoceptor subtypes. Z. Naturforsch. C J. Biosci., 2002, 57(3-4), 332-338.
[http://dx.doi.org/10.1515/znc-2002-3-423] [PMID: 12064736]
[86]
Osman, N.N.; Alanbari, K.H.; Al-Shreef, H.A. Evaluation of the possinle antioxidant effects of Peganum harmala and Ginkgo biloba in ameliorating Alzheimer’s disease in rat model. Int. J. Pharm. Sci. Res., 2018, 9, 3189-3198.
[87]
Xue, L.G.; Zhao, G.L.; Zhang, B.Q.; Tang, D.P. Extraction and anti-bacterial alkaloids of Peganum harmala. J. Tradit. Chin. Vet. Med., 2007, 3, 16-19.
[88]
Zhao, T.; Ding, K.; Zhang, L.; Cheng, X.; Wang, C.; Wang, Z. Acetylcholinesterase and butyrylcholinesterase inhibitory activities of β-carboline and quinoline alkaloids derivatives from the plants of genus peganum. J. Chem., 2013, 2013, 1-6.
[http://dx.doi.org/10.1155/2013/717232]
[89]
Djarmouni, M.; Boumerfeg, S.; Baghiani, A.; Boussoualim, N.; Zerargui, F.; Trabsa, H.; Belkhiri, F.; Khennouf, S.; Arrar, L. Evaluation of antioxidant and antibacterial properties of Peaganum harmala seed extracts. Res. J. Pharm. Biol. Chem. Sci., 2018, 3, 1109-1119.
[90]
Khalid, R.; Jaffar, Q.; Tayyeb, A.; Qaisar, U. Peganum harmalapeptides (PhAMP) impede bacterial growth and biofilm formation in burn and surgical wound pathogens. Pak. J. Pharm. Sci., 2018, 31(6), 2597-2605.
[PMID: 30587467]
[91]
Nenaah, G. Antibacterial and antifungal activities of (β)-carboline alkaloids of Peganum harmala (L) seeds and their combination effects. Fitoterapia, 2010, 81(7), 779-782.
[http://dx.doi.org/10.1016/j.fitote.2010.04.004] [PMID: 20398742]
[92]
Bensalem, S.; Soubhye, J.; Aldib, I.; Bournine, L.; Nguyen, A.T.; Vanhaeverbeek, M.; Rousseau, A.; Boudjeltia, K.Z.; Sarakbi, A.; Kauffmann, J.M.; Nève, J.; Prévost, M.; Stévigny, C.; Maiza-Benabdesselam, F.; Bedjou, F.; Van Antwerpen, P.; Duez, P. Inhibition of myeloperoxidase activity by the alkaloids of Peganum harmala L. (Zygophyllaceae). J. Ethnopharmacol., 2014, 154(2), 361-369.
[http://dx.doi.org/10.1016/j.jep.2014.03.070] [PMID: 24746482]
[93]
Chen, W.R.; Zhang, H.R.; Zhang, Y.; Feng, Y.J. Anti-inflammatory, analgesic and anti-pruritic effects of harmine. Tianjin Yi Yao, 2004, 32, 681-683.
[94]
Niu, X.; Yao, Q.; Li, W.; Zang, L.; Li, W.; Zhao, J.; Liu, F.; Zhi, W. Harmine mitigates LPS-induced acute kidney injury through inhibition of the TLR4-NF-κB/NLRP3 inflammasome signalling pathway in mice. Eur. J. Pharmacol., 2019, 849, 160-169.
[http://dx.doi.org/10.1016/j.ejphar.2019.01.062] [PMID: 30716318]
[95]
Liu, X.; Li, M.; Tan, S.; Wang, C.; Fan, S.; Huang, C. Harmine is an inflammatory inhibitor through the suppression of NF-κB signaling. Biochem. Biophys. Res. Commun., 2017, 489(3), 332-338.
[http://dx.doi.org/10.1016/j.bbrc.2017.05.126] [PMID: 28551404]
[96]
Kumar, M.; Joshi, S.; Kulkarni, V.; Savant, C. Phytochemical screening and evaluation of analgesic, anti-inflammatory activities of Peganum harmala Linn., seeds in rodents. J. Appl. Pharm. Sci., 2015, 5, 052-055.
[http://dx.doi.org/10.7324/JAPS.2015.50510]
[97]
Mahajna, S.; Azab, M.; Zaid, H.; Farich, B.; Battah, F.; Mashner, S.; Saad, B. In vitro evaluations of cytotoxicity and anti-inflammatory effects of Peganum harmala L. seed extracts in THP-1-derived macrophages. European J. Med. Plants, 2015, 5(2), 165-175.
[http://dx.doi.org/10.9734/EJMP/2015/13267]
[98]
Poorbarkhordari, E.; Fooladsaz, K.; Hosseini, S.H.; Danafar, H.; Ramazani, A. The hypoglycemic effects of an ethanol extract of Peganum harmala L. in streptozotocin-induced diabetic rats. Iran. J. Pharm. Res., 2014, 10, 47-54.
[99]
Waki, H.; Park, K.W.; Mitro, N.; Pei, L.; Damoiseaux, R.; Wilpitz, D.C.; Reue, K.; Saez, E.; Tontonoz, P. The small molecule harmine is an antidiabetic cell-type-specific regulator of PPARgamma expression. Cell Metab., 2007, 5(5), 357-370.
[http://dx.doi.org/10.1016/j.cmet.2007.03.010] [PMID: 17488638]
[100]
Liu, W.; Cheng, X.M.; Wang, Z.T.; Wang, C.H. Research progress on resources, pharmacological activity, toxicity, pharmacokinetics, and analytical methods of vasicine. J. Int. Pharm. Res, 2013, 40, 386-395.
[101]
Abedi Gaballu, F.; Abedi Gaballu, Y.; Moazenzade Khyavy, O.; Mardomi, A.; Ghahremanzadeh, K.; Shokouhi, B.; Mamandy, H. Effects of a triplex mixture of Peganum harmala, Rhus coriaria, and Urtica dioica aqueous extracts on metabolic and histological parameters in diabetic rats. Pharm. Biol., 2015, 53(8), 1104-1109.
[http://dx.doi.org/10.3109/13880209.2014.960943] [PMID: 25612773]
[102]
Wang, Z.L.; Song, Y.L.; Xing, W.; Wu, Y.; Wang, W.; Han, J. The regulatory effect and mechanism of water extract of Peganum harmala on retinal vascular endothelial cells under high glucose exposure. J. Beijing Univ. Tradit. Chin. Med., 2018, 41, 738-743.
[103]
Miraj, S. A review study of therapeutic effects of Peganum harmala. Pharm. Lett., 2016, 8, 161-166.
[104]
Liu, F.; Li, G.H. Preliminary study on the pharmacological effects of alkaloids from Peganum harmala. Xinjiang Yike Daxue Xuebao, 1980, 3, 143-148.
[105]
Berrougui, H.; Martíncordero, C.; Khalil, A.; Hmamouchi, M.; Ettaib, A.; Marhuenda, E.; Herrera, M. Vasorelaxant effects of harmine and harmaline extracted from Peganum harmala L. seed’s in isolated rat aorta. Pharmacol. Res., 2006, 54(2), 150-157.
[http://dx.doi.org/10.1016/j.phrs.2006.04.001] [PMID: 16750635]
[106]
Xu, X.; Zhao, Z. Anti-tussive and anti-asthmatic effects of Peganum harmala on isolated trachea. Xibei Yaoxue Zazhi, 1991, 6, 15-17.
[107]
Liu, W.; Yang, Y.; Cheng, X.; Gong, C.; Li, S.; He, D.; Yang, L.; Wang, Z.; Wang, C. Rapid and sensitive detection of the inhibitive activities of acetyl- and butyryl-cholinesterases inhibitors by UPLC–ESI-MS/MS. J. Pharm. Biomed. Anal., 2014, 94, 215-220.
[http://dx.doi.org/10.1016/j.jpba.2014.02.004] [PMID: 24631841]
[108]
Zhao, X.M.; Zeng, Z.H. The research of the pesticidal activity on different Peganum harmala extractions. Zhongguo Nongxue Tongbao, 2005, 21, 278-279.
[109]
Chen, B.; Gao, H.J.; Gong, Y.H.; Wen, L.M.; Lu, S.; Wang, J.H.; Zhao, J. The Effect of dehydroharmaline on Th1/Th2 cytokines in peripheral blood of mice infected with Echinococcus granulosus. J. Pathog. Biol., 2019, 14, 1038-1043.
[110]
Gong, Y.H.; Gao, H.J.; Lu, S.; Zheng, X.; Wen, L.M.; Chen, B.; Zhao, J.; Wang, J.H. Detection and analysis of caspase-3 and anti-oxidant enzyme activities during the induction of apoptosis in the protoscolex of echinococcus granulosus In vitro by dehydropalmatine. J. Pathog. Biol., 2018, 13, 1207-1210.
[111]
Shang, X.; Guo, X.; Li, B.; Pan, H.; Zhang, J.; Zhang, Y.; Miao, X. Microwave-assisted extraction of three bioactive alkaloids from Peganum harmala L. and their acaricidal activity against Psoroptes cuniculi In vitro. J. Ethnopharmacol., 2016, 192, 350-361.
[http://dx.doi.org/10.1016/j.jep.2016.07.057] [PMID: 27452655]
[112]
Cheng, X.M.; Liu, Y.Q.; Xie, H.D.; Wang, C.H.; Wang, Z.T. HPLC-fluorescence detection of dehydroharmaline and harmaline in the seeds of Peganum harmala L. Carol. J. Pharm., 2008, 39, 443-446.
[113]
Zhao, X. Accumulation patterns of amino acid components in Peganum harmala L. and its effects on acute toxicity and pharmacokinetics of vasicine. Master's Thesis Xinjiang Med. University, Urumqi, 2015.
[114]
Yin, Q.N.; Chen, X.L.; Xiao, H.T. Research on pharmacological research of dehydroharmaline. Chin. J. Clin. Pharmacol., 2019, 35, 594-596.
[115]
Deng, G. Study on the improvement of learning and memory by deoxypeganine and its pharmacokinetics. Master's Thesis Shanghai Univ. Tradit. Chin. Med. University, Shanghai., 2019.
[116]
Ran, X.; Gao, H.J.; Li, Y.L.; Chen, B.; Chen, G.R.; Teng, L. Pharmacokinetic study of different doses of harmine in rats after single administration based on UPLC-MS/MS. Chin. J. Clin. Pharmacol., 2019, 35, 3095-3100.
[117]
Yuan, J.; Ji, R.F.; Quan, Q.H.; Wang, J.L.; Guo, X.Y.; Zhang, J.M.; Tan, P.; Han, J.; Liu, Y.G. Metabolism of dehydroharmaline in the body of Cryptomeria elegans. J. Chin. Mass Spectrom. Soc., 2017, 38, 478-485.
[118]
Shi, X.Y.; Liu, W.; Zhang, L.; Li, S.P.; Cheng, X.M.; Xi, Y.; Wang, C.H. Pharmacokinetic studies on peganine and dehydrogenase of Peganum harmala L. and their metabolites in rats. Zhongchengyao, 2014, 36, 1169-1175.
[119]
Deng, G.; Liu, W.; Ma, C.; Rong, X.; Zhang, Y.; Wang, Y.; Wu, C.; Cao, N.; Ding, W.; Guan, H.; Cheng, X.; Wang, C. In vivo and In vitro metabolism and pharmacokinetics of cholinesterase inhibitor deoxyvasicine from aerial parts of Peganum harmala Linn in rats via UPLC-ESI-QTOF-MS and UPLC-ESI-MS/MS. J. Ethnopharmacol., 2019, 236, 288-301.
[http://dx.doi.org/10.1016/j.jep.2019.03.020] [PMID: 30872168]
[120]
Li, L.; Li, Y.; Wang, T.Y. Establishment of qualitative discriminative model of Peganum harmala L. from different habitats based on near-infrared spectroscopy. Zhongguo Zhongyao Zazhi, 2015, 40, 2862-2865.
[PMID: 26666040]
[121]
Kartal, M.; Altun, M.L.; Kurucu, S. HPLC method for the analysis of harmol, harmalol, harmine and harmaline in the seeds of Peganum harmala L. J. Pharm. Biomed. Anal., 2003, 31(2), 263-269.
[http://dx.doi.org/10.1016/S0731-7085(02)00568-X] [PMID: 12609665]
[122]
Wen, F.F.; Zheng, L.M.; Li, X.J.; Li, Y.; Zhang, L.; Cheng, X.M.; Wang, C.H.; Wang, Z.T. Study on the quality standards of Uyghur medicine Peganum harmala L. Zhongguo Zhongyao Zazhi, 2012, 37, 2971-2976.
[PMID: 23270245]
[123]
Gao, J. Study on the processing of Peganum harmala L. and the synthesis and activity evaluation of halfenone. Master's Thesis Beijing Univ. Tradit. Chin. Med. University, Beijing. 2018.
[124]
Miao, X.Z. Study on the toxic effects and mechanisms of different processed products of Peganum harmala L. based on the model of Elegant cryptorhabditis. Master's Thesis Beijing Univ. Tradit. Chin. Med. University, Beijing, 2019.
[125]
Moradi, M.T.; Karimi, A.; Fotouhi, F.; Kheiri, S.; Torabi, A. In vitro and In vivo effects of Peganum harmala L. seeds extract against influenza A virus. Avicenna J. Phytomed., 2017, 7(6), 519-530.
[PMID: 29299435]
[126]
Abderrahman, S.M.; Soliman, S.; Mohammad, M. Genotoxic effects of Peganum harmala L. in relation to traditional use. J. Pharmacogn. Phytother., 2018, 10, 167-173.
[127]
Mahmoudian, M.; Jalilpour, H.; Salehian, P. Toxicity of Peganum harmala: Review and a case report. Iranian J. Pharmacol. Ther, 2002, 1, 1-4.
[128]
Pan, Q.C.; Yang, X.P. Study on the pharmacological effects of total alkaloids from Peganum harmala L. J. Sun Yat-sen Med. Univ, 1997, 18, 165-167.

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