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β-Carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO)
Abstract
Peganum harmala L. is a multipurpose medicinal plant increasingly used for psychoactive recreational purposes (Ayahuasca analog). Harmaline, harmine, harmalol, harmol and tetrahydroharmine were identified and quantified as the main beta-carboline alkaloids in P. harmala extracts. Seeds and roots contained the highest levels of alkaloids with low levels in stems and leaves, and absence in flowers. Harmine and harmaline accumulated in dry seeds at 4.3% and 5.6% (w/w), respectively, harmalol at 0.6%, and tetrahydroharmine at 0.1% (w/w). Roots contained harmine and harmol with 2.0% and 1.4% (w/w), respectively. Seed extracts were potent reversible and competitive inhibitors of human monoamine oxidase (MAO-A) with an IC(50) of 27 microg/l whereas root extracts strongly inhibited MAO-A with an IC(50) of 159 microg/l. In contrast, they were poor inhibitors of MAO-B. Inhibition of MAO-A by seed extracts was quantitatively attributed to harmaline and harmine whereas inhibition by root extracts came from harmine with no additional interferences. Stems and leaves extracts were poor inhibitors of MAO. The potent inhibition of MAO-A by seed and root extracts of P. harmala containing beta-carbolines should contribute to the psychopharmacological and toxicological effects of this plant and could be the basis for its purported antidepressant actions.
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“Here we address the other important active agents of ayahuasca, the β-carboline alkaloids, which act as selective, reversible MAO-A inhibitors (McKenna and Towers, 1984; dos Santos, 2010) with almost no effect on MAO-B (Herraiz et al., 2010).”
From The therapeutic potentials of Ayahuasca: possible effects against various diseases of civilization (2016) · cites this paper as Herraiz et al., 2010
Citations
Cites
The therapeutic potential of monoamine oxidase inhibitors
Youdim, M. B. H., Edmondson, D. E., & Tipton, K. F. (2006) · Nature reviews. Neuroscience · doi:10.1038/nrn1883 · Cited by 1,401
MONOAMINE OXIDASE: From Genes to Behavior
Shih, J. C., Chen, K., & Ridd, M. J. (1999) · Annual Review of Neuroscience · doi:10.1146/annurev.neuro.22.1.197 · Cited by 1,235
Clinical Pharmacology of MAO Inhibitors: Safety and Future
Yamada, M. (2003) · NeuroToxicology · doi:10.1016/s0161-813x(03)00097-4 · Cited by 325
McKenna, D. J. (2004) · Pharmacology & Therapeutics · doi:10.1016/j.pharmthera.2004.03.002 · Cited by 321
Pharmacokinetics of Hoasca alkaloids in healthy humans
Callaway, J. C., McKenna, D. J., Grob, C. S., Brito, G. S., Raymon, L. P., Poland, R. E., Andrade, E. O., Andrade, E. O., & Mash, D. C. (1999) · Journal of Ethnopharmacology · doi:10.1016/s0378-8741(98)00168-8 · Cited by 318
Herraiz, T., & Chaparro, C. (2004) · Biochemical and Biophysical Research Communications · doi:10.1016/j.bbrc.2004.11.033 · Cited by 258
Inhibition of Monoamine Oxidase A by β-Carboline Derivatives
Kim, H., Sablin, S. O., & Ramsay, R. R. (1997) · Archives of Biochemistry and Biophysics · doi:10.1006/abbi.1996.9771 · Cited by 252
Monoamine oxidase and cigarette smoking
Fowler, J. S., Logan, J., Wang, G.-J., & Volkow, N. D. (2003) · NeuroToxicology · doi:10.1016/s0161-813x(02)00109-2 · Cited by 251
Farouk, L., Laroubi, A., Aboufatima, R., Ahmed Benharref, A., & Chait, A. (2007) · Journal of Ethnopharmacology · doi:10.1016/j.jep.2007.10.014 · Cited by 188
Kartal, M., Altun, M. L., & Kurucu, S. (2003) · Journal of Pharmaceutical and Biomedical Analysis · doi:10.1016/s0731-7085(02)00568-x · Cited by 181
Specific inhibition of cyclin-dependent kinases and cell proliferation by harmine
Song, Y., Kesuma, D., Wang, J., Deng, Y., Duan, J., Wang, J. H.-C., & Qi, R. Z. (2004) · Biochemical and Biophysical Research Communications · doi:10.1016/j.bbrc.2004.03.019 · Cited by 180
Antidepressant-like effect of harmane and other β-carbolines in the mouse forced swim test
Farzin, D., & Mansouri, N. (2006) · European Neuropsychopharmacology · doi:10.1016/j.euroneuro.2005.08.005 · Cited by 171
Youdim, M. B. H. (2003) · NeuroToxicology · doi:10.1016/s0161-813x(03)00103-7 · Cited by 160
Toxicity of Peganum harmala: Review and a Case Report
Mahmoudian, M., Jalilpour, H., & Salehian, P. (2002) · TSpace (University of Toronto) · Cited by 156
Elevation of blood β-carboline alkaloids in essential tremor
Louis, E. D., Zheng, W., Jurewicz, E. C., Watner, D., Chen, J., Factor-Litvak, P. R., & Parides, M. K. (2002) · Neurology · doi:10.1212/01.wnl.0000038385.60538.19 · Cited by 148
Alkaloids from the seeds of Peganum harmala showing antiplasmodial and vasorelaxant activities
Astulla, A., Zaima, K., Matsuno, Y., Hirasawa, Y., Ekasari, W., Widyawaruyanti, A., Zaini, N. C., & Morita, H. (2008) · Journal of Natural Medicines · doi:10.1007/s11418-008-0259-7 · Cited by 146
Herraiz, T., & Chaparro, C. (2005) · Life Sciences · doi:10.1016/j.lfs.2005.05.074 · Cited by 144
Pieroni, A., Muenz, H., Akbulut, M., Başer, K. H. C., & Durmuşkahya, C. (2005) · Journal of Ethnopharmacology · doi:10.1016/j.jep.2005.05.018 · Cited by 144
Pharmahuasca: Human Pharmacology of Oral DMT Plus Harmine
Ott, J. (1999) · Journal of Psychoactive Drugs · doi:10.1080/02791072.1999.10471741 · Cited by 140
Madadkar‐Sobhani, A., Ebrahimi, S.-A., & Mahmoudian, M. (2002) · PubMed · Cited by 132
beta-Carbolines, psychoactive compounds in the mammalian body. Part II: Effects.
Airaksinen, M. M., & Karí, I. (1981) · PubMed · Cited by 127
Antinociceptive effects of Peganum harmala L. alkaloid extract on mouse formalin test.
Monsef, H., Ghobadi, A., Iranshahi, M., & Abdollahi, M. R. (2004) · PubMed · Cited by 126
β-carboline binding to imidazoline receptors
Husbands, S. M., Glennon, R. A., Gorgerat, S., Gough, R., Tyacke, R. J., Crosby, J. C., Nutt, D., Lewis, J. W., & Hudson, A. L. (2001) · Drug and Alcohol Dependence · doi:10.1016/s0376-8716(01)00123-5 · Cited by 126
Yu, A., Idle, J. R., Krausz, K. W., Kupfer, A., & Gonzalez, F. J. (2003) · Journal of Pharmacology and Experimental Therapeutics · doi:10.1124/jpet.102.047050 · Cited by 123
Monoamine Oxidase Inhibitor Poisoning Resulting from Internet Misinformation on Illicit Substances
Brush, D. E., Bird, S. B., & Boyer, E. W. (2004) · Journal of Toxicology Clinical Toxicology · doi:10.1081/clt-120030949 · Cited by 120
A case of β-carboline alkaloid intoxication following ingestion of Peganum harmala seed extract
Frison, G., Favretto, D., Zancanaro, F., Fazzin, G., & Ferrara, S. D. (2008) · Forensic Science International · doi:10.1016/j.forsciint.2008.05.003 · Cited by 118
Harman (1-methyl-β-carboline) is a natural inhibitor of monoamine oxidase type A in rats
Rommelspacher, H., May, T., & Salewski, B. (1994) · European Journal of Pharmacology · doi:10.1016/0014-2999(94)90574-6 · Cited by 113
Monoamine Oxidase and Mitochondrial Respiration
Cohen, G., & Kesler, N. (1999) · Journal of Neurochemistry · doi:10.1046/j.1471-4159.1999.0732310.x · Cited by 113
Screening for endogenous substrates reveals that CYP2D6 is a 5-methoxyindolethylamine O-demethylase.
Yu, A., Idle, J. R., Herraiz, T., Kupfer, A., & Gonzalez, F. J. (2003) · PubMed · doi:10.1097/01.fpc.0000054094.48725.b7 · Cited by 111
Phytochemical Analyses ofBanisteriopsis CaapiandPsychotria Viridis
Callaway, J. C., Brito, G. S., & Neves, E. S. (2005) · Journal of Psychoactive Drugs · doi:10.1080/02791072.2005.10399795 · Cited by 92
Antitumour principles from Peganum harmala seeds.
Lamchouri, F., Settaf, A., Cherrah, Y., Zemzami, M., Lyoussi, B., Zaïd, A., Atif, N., & Hassar, M. (1999) · PubMed · Cited by 89
Harmane Induces Anxiolysis and Antidepressant‐Like Effects in Rats
Arıcıoğlu, F., & Altunbas, H. (2003) · Annals of the New York Academy of Sciences · doi:10.1196/annals.1304.024 · Cited by 83
Various Alkaloid Profiles in Decoctions of Banisteriopsis Caapi
Callaway, J. C. (2005) · Journal of Psychoactive Drugs · doi:10.1080/02791072.2005.10399796 · Cited by 77
Miralles, A., Esteban, S., Sastre-Coll, A., Moranta, D., Asensio, V. J., & Garcı́a-Sevilla, J. A. (2005) · European Journal of Pharmacology · doi:10.1016/j.ejphar.2005.06.023 · Cited by 76
Hypothermic effect of harmala alkaloid in rats: Involvement of serotonergic mechanism
Abdel-Fattah, A.-F. M., Matsumoto, K., Gammaz, H. A., & Watanabe, H. (1995) · Pharmacology Biochemistry and Behavior · doi:10.1016/0091-3057(95)00131-f · Cited by 73
Hemmateenejad, B., Abbaspour, A., Maghami, H., Miri, R., & Panjehshahin, M. R. (2006) · Analytica Chimica Acta · doi:10.1016/j.aca.2006.05.093 · Cited by 73
Occurence and partition of the β-carboline norharman in rat organs
Fekkes, D., & Bode, W. T. (1993) · Life Sciences · doi:10.1016/0024-3205(93)90689-z · Cited by 71
Boeira, J. M., Viana, A. F., Picada, J. N., & Henriques, J. A. P. (2002) · Mutation research. Fundamental and molecular mechanisms of mutagenesis · doi:10.1016/s0027-5107(01)00294-9 · Cited by 70
Adell, A., Biggs, T. A. G., & MYERS, R. D. (1996) · Neuropharmacology · doi:10.1016/s0028-3908(96)00043-3 · Cited by 70
Peganum harmala L: a poisonous plant of North Africa.
Bahri, L. E., & Chemli, R. (1991) · PubMed · Cited by 63
Web Sites with Misinformation about Illicit Drugs
Boyer, E. W., Shannon, M., & Hibberd, P. L. (2001) · New England Journal of Medicine · doi:10.1056/nejm200108093450619 · Cited by 61
Herraiz, T., & Chaparro, C. (2005) · Journal of Chromatography A · doi:10.1016/j.chroma.2005.12.009 · Cited by 59
Herraiz, T., Guillén, H., & Arán, V. J. (2008) · Chemical Research in Toxicology · doi:10.1021/tx8002565 · Cited by 59
Wu, C., Jiang, X.-L., Shen, H.-W., & Yu, A. (2009) · Biochemical Pharmacology · doi:10.1016/j.bcp.2009.05.011 · Cited by 50
Long-term retention of neurotoxic ?-carbolines in brain neuromelanin
stergren, A. X. D., Annas, A., Skog, K. I., Lindquist, N. G., & Brittebo, E. B. (2004) · Journal of Neural Transmission · doi:10.1007/s00702-003-0080-0 · Cited by 49
Im, J., Jin, Y.-R., Lee, J., Yu, J., Han, X., Im, S.-H., Hong, J. T., Yoo, H., Pyo, M., & Yun, Y. (2008) · Vascular Pharmacology · doi:10.1016/j.vph.2008.11.008 · Cited by 47
Berrougui, H., Isabelle, M., Cloutier, M., Hmamouchi, M., & Khalil, A. (2006) · Journal of Pharmacy and Pharmacology · doi:10.1211/jpp.58.7.0012 · Cited by 40
Harmane and Harmalan Are Bioactive Components of Classical Clonidine-Displacing Substance
Parker, C. A., Anderson, N. J., Robinson, E. S. J., Price, R., Tyacke, R. J., Husbands, S. M., Dillon, M. P., Eglen, R. M., Hudson, A. L., Nutt, D., et al. (2004) · Biochemistry · doi:10.1021/bi048584v · Cited by 38
Herraiz, T., Guillén, H., Arán, V. J., Idle, J. R., & Gonzalez, F. J. (2006) · Toxicology and Applied Pharmacology · doi:10.1016/j.taap.2006.06.003 · Cited by 36
Pimpinella, G., & Palmery, M. (1995) · Neuroscience Letters · doi:10.1016/0304-3940(95)11469-d · Cited by 35
Pulpati, H., Biradar, Y. S., & Rajani, M. (2008) · Journal of AOAC International · doi:10.1093/jaoac/91.5.1179 · Cited by 34
Tsuchiya, H., Hayashi, H., Satô, M., Shimizu, H., & Iinuma, M. (1999) · Phytochemical Analysis · doi:10.1002/(sici)1099-1565(199909/10)10:5 · Cited by 27
Antimicrobial and cytotoxicity potential of Peganum harmala smoke
Shahverdi, A. R., Ostad, S. N., Khodaee, S., Bitarafan, L., Monsef-Esfahani, H. R., Jamalifar, H., Nickavar, B., & Mohseni, M. (2008) · Pharmacognosy Magazine · Cited by 22
Antimicrobial Principles from In Vitro Tissue Culture of Peganum harmala
Harsh, M. L., & Nag, T. N. (1984) · Journal of Natural Products · doi:10.1021/np50032a022 · Cited by 20
Using monoamine oxidase type B inhibitors in Parkinson's disease
Ben‐Shlomo, Y., & Bhatia, K. (2004) · BMJ · doi:10.1136/bmj.329.7466.581 · Cited by 18
Herraiz, T., Arán, V. J., & Guillén, H. (2009) · Free Radical Research · doi:10.1080/10715760903159170 · Cited by 16
[A case of overdose with Peganum harmala L].
Ben Salah, N., Amamou, M., Jerbi, Z., Ben Salah, F., & Yacoub, M. (1986) · PubMed · Cited by 12
Martins, C. P. B., Awan, M. A., Freeman, S., Herraiz, T., Alder, J. F., & Brandt, S. D. (2008) · Journal of Chromatography A · doi:10.1016/j.chroma.2008.09.036 · Cited by 11
Research works printed but not linked: 4
- Airaksinen, 1981, β-Carbolines, psychoactive compounds in the mammalian body. 2. Effects, Med. Biol., 59, 190
- Ben Salah, 1986, Aspects cliniques, pharmacologiques et toxicologiques du surdosage par une plante medicinale: le harmel, Essaydali Scientifique, 21, 13
- Kusmenoglu, 1996, The plant Peganum harmala L. and its biologically active constitutents, FABAD J. Pharm. Sci., 21, 71
- McKenna, 1998, The sciencific investigation of Ayahuasca: a review of past and current research, Heffter Rev. Psychedelic Res., 1, 65
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“harmala has been used among societies to treat some nervous system disorders such as Parkinson`s disease,[19] in psychiatric conditions[7] such as nervosity,[20] and to relieve rigorous pain.”
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“Here we address the other important active agents of ayahuasca, the β-carboline alkaloids, which act as selective, reversible MAO-A inhibitors (McKenna and Towers, 1984; dos Santos, 2010) with almost no effect on MAO-B (Herraiz et al., 2010).”
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“In humans, they can reversibly block the activity of subtype A of the monoamine-oxidase (MAO) enzyme (Undenfriend et al., 1958; Buckholtz and Boggan, 1977a, Wang et al., 2010; Herraiz et al., 2010).”
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Metadata
- Authors
- Herraiz, T., González, D., Ancín-Azpilicueta, C., Arán, V. J., & Guillén, H.
- Affiliations
- Consejo Superior de Investigaciones Científicas (ES)
- Instituto de Química Médica (ES)
- Corresponding author
- Herraiz, T.
- Venue
- Food and Chemical Toxicology
- Publisher
- Elsevier BV
- Published
- 2010-03
- Volume
- 48
- Issue
- 3
- Pages
- 839-845
- ISSN
- 0278-6915 (ISSN-L)
- OpenAlex
- W2169624105
- Cited by
- 357
- References
- 59
- Citations by year
- 2026: 31 · 2025: 24 · 2024: 16 · 2023: 25 · 2022: 27 · 2021: 25 · 2020: 26 · 2019: 26 · 2018: 18 · 2017: 19 · 2016: 21 · 2015: 18 · 2014: 23 · 2013: 23 · 2012: 12
- FWCI
- 4.69
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Food and Chemical Toxicology (publishedVersion)
- PubMed (publishedVersion)
- DIGITAL.CSIC (Spanish National Research Council (CSIC)) (submittedVersion)
- Funders
- Spanish government (AGL2006-02414)
- CSIC (200470E658)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis and bioactivity of alkaloids
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmacology › Alkaloids: synthesis and pharmacology
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Toxicology › Forensic Toxicology and Drug Analysis
- Keywords
- Peganum harmala, β-carbolines, harmine, harmaline, harmol, tetrahydroharmine, harmalol, monoamine oxidase A inhibition, monoamine oxidase B inhibition, seeds, roots, antidepressant effects, psychopharmacology, toxicology
- MeSH terms
- Carbolines, Chromatography, High Pressure Liquid, Harmaline, Harmine, Humans, Kinetics, Monoamine Oxidase, Monoamine Oxidase Inhibitors, Plant Extracts, Seeds, Spectrophotometry, Ultraviolet, Plant Roots, Spectrometry, Mass, Electrospray Ionization, Peganum
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