Cited by 362Synthesis and bioactivity of alkaloidsAlkaloids: synthesis and pharmacologyForensic Toxicology and Drug Analysis

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β-Carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO)

Herraiz, T., González, D., Ancín-Azpilicueta, C., Arán, V.J., Guillén, H.·2010·Food and Chemical Toxicology

DOI 10.1016/j.fct.2009.12.019

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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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Szmulewicz, A., Valerio, M. P., & Smith, J. M. (2015) · International Journal of Bipolar Disorders · doi:10.1186/s40345-014-0020-y · Cited by 45
Facile synthesis of silver nanoparticles using harmala alkaloids and their insecticidal and growth inhibitory activities against the khapra beetle
Almadiy, A. A., Nenaah, G. E., & Shawer, D. (2017) · Journal of Pest Science · doi:10.1007/s10340-017-0924-2 · Cited by 45
“These β-carbolines can easily cross the blood–brain barrier altering the neurotransmitter concentrations, exerting a variety of neurophysiological and toxicological effects (Herraiz et al. 2010).”
Background
Peripheral modulation of antidepressant targets MAO-B and GABAAR by harmol induces mitohormesis and delays aging in preclinical models
Costa‐Machado, L. F., García-Domínguez, E., McIntyre, R. L., López-Aceituno, J. L., Ballesteros-Gonzalez, Á., Tapia-Gonzalez, A., Fabregat‐Safont, D., Eisenberg, T., Gómez, J., Plaza, A., et al. (2023) · Nature Communications · doi:10.1038/s41467-023-38410-y · Cited by 47
“As a positive control, we used harmine, another β -carboline previously described as a pan-MAO inhibitor 41 that we also detected in our initial screen (Fig.”
Harmine suppresses the proliferation of pancreatic cancer cells and sensitizes pancreatic cancer to gemcitabine treatment
Wu, L., Zhang, J., Rao, M., Zhang, Z., Zhu, H., & Zhang, C. (2019) · OncoTargets and Therapy · doi:10.2147/ott.s205097 · Cited by 44
Improving health benefits with considering traditional and modern health benefits of Peganum harmala
Shahrajabian, M. H., Sun, W., & Cheng, Q. (2021) · Clinical Phytoscience · doi:10.1186/s40816-021-00255-7 · Cited by 44
Harmaline and harmalol inhibit the carcinogen-activating enzyme CYP1A1 via transcriptional and posttranslational mechanisms
Gendy, M. A. M. E., Soshilov, A. A., Denison, M. S., & El‐Kadi, A. O. S. (2011) · Food and Chemical Toxicology · doi:10.1016/j.fct.2011.10.052 · Cited by 44
“Harmaline and harmalol are common dihydro-β-carbolines that widely distributed in the environment including alcoholic beverages and several plants such as Peganum harmala (Zygophyllaceae) (Herraiz et al., 2010; Park et al., 2010).”
BackgroundInfluential
Harmol promotes α-synuclein degradation and improves motor impairment in Parkinson’s models via regulating autophagy-lysosome pathway
Xu, J., Ao, Y., Huang, C., Song, X., Zhang, G., Cui, W., Wang, Y., Zhang, X., & Zhang, Z. (2022) · npj Parkinson s Disease · doi:10.1038/s41531-022-00361-4 · Cited by 43
Synthesis and antitumor activity of novel N-substituted tetrahydro-β-carboline–imidazolium salt derivatives
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Analysis of monoamine oxidase (MAO) enzymatic activity by high-performance liquid chromatography-diode array detection combined with an assay of oxidation with a peroxidase and its application to MAO inhibitors from foods and plants
Herraiz, T., Flores, A., & Fernández, L. (2017) · Journal of Chromatography B · doi:10.1016/j.jchromb.2017.12.004 · Cited by 43
Hydroxamic Acid Derivatives of β-Carboline/Hydroxycinnamic Acid Hybrids Inducing Apoptosis and Autophagy through the PI3K/Akt/mTOR Pathways
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Eco-friendly liquid chromatographic separations based on the use of cyclodextrins as mobile phase additives
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Cytotoxic Indole Alkaloids against Human Leukemia Cell Lines from the Toxic Plant Peganum harmala
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“Recently, much research has revealed that β-carboline and quinazoline alkaloids are important ingredients, accounting for many of the pharmacological and therapeutic effects, such as analgesic [4], antibacterial [5], antiparasitic [6], strong reversible inhibition activity of monoamine oxidase [7], cytotoxic and antit…”
Background
Mechanism-based pharmacokinetics-pharmacodynamics studies of harmine and harmaline on neurotransmitters regulatory effects in healthy rats: Challenge on monoamine oxidase and acetylcholinesterase inhibition
Jiang, B., Meng, L., Zou, N., Wang, H., Li, S., Huang, L., Cheng, X. M., Wang, Z., Chen, W., & Wang, C. (2019) · Phytomedicine · doi:10.1016/j.phymed.2019.152967 · Cited by 42
Harmine derivatives: a comprehensive quantum chemical investigation of the structural, electronic (FMO, NBO, and MEP), and spectroscopic (FT-IR and UV–Vis) properties
Serdaroğlu, G. (2019) · Research on Chemical Intermediates · doi:10.1007/s11164-019-04020-x · Cited by 42
Computational & experimental evaluation of the structure/activity relationship of β-carbolines as DYRK1A inhibitors
Drung, B., Scholz, C., Barbosa, V. A., Nazari, A., Sarragiotto, M. H., & Schmidt, B. (2014) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/j.bmcl.2014.08.054 · Cited by 41
The Therapeutic Prospects of Naturally Occurring and Synthetic Indole Alkaloids for Depression and Anxiety Disorders
Munir, S., Shahid, A., Aslam, B., Ashfaq, U. A., Akash, M. S. H., Ali, M. A., Almatroudi, A., Allemailem, K. S., Rajoka, M. S. R., & Khurshid, M. (2020) · Evidence-based Complementary and Alternative Medicine · doi:10.1155/2020/8836983 · Cited by 42
Toxicity and growth inhibitory activities of methanol extract and the β-carboline alkaloids of Peganum harmala L. against two coleopteran stored-grain pests
Nenaah, G. E. (2011) · Journal of Stored Products Research · doi:10.1016/j.jspr.2011.04.004 · Cited by 40
Inhibition of monoamine oxidase (MAO) by β-carbolines and their interactions in live neuronal (PC12) and liver (HuH-7 and MH1C1) cells
Santillo, M. F., Liu, Y., Ferguson, M. S., Vohra, S., & Wiesenfeld, P. L. (2014) · Toxicology in Vitro · doi:10.1016/j.tiv.2013.12.006 · Cited by 38
N-methyltetrahydropyridines and pyridinium cations as toxins and comparison with naturally-occurring alkaloids
Herraiz, T. (2016) · Food and Chemical Toxicology · doi:10.1016/j.fct.2016.08.009 · Cited by 39
Cross‐Cultural Analysis of Medicinal Plants commonly used in Ethnoveterinary Practices at South Waziristan Agency and Bajaur Agency, Federally Administrated Tribal Areas (FATA), Pakistan
Aziz, M. A., Adnan, M., Khan, A. H., Sufyan, M., & Khan, S. N. (2017) · Journal of Ethnopharmacology · doi:10.1016/j.jep.2017.09.007 · Cited by 39
Identification, occurrence and activity of quinazoline alkaloids in Peganum harmala
Herraiz, T., Guillén, H., Arán, V. J., & Salgado, A. (2017) · Food and Chemical Toxicology · doi:10.1016/j.fct.2017.03.010 · Cited by 38
Anticancer Potential of β‐Carboline Alkaloids: An Updated Mechanistic Overview
Tshikhudo, P. P., Mabhaudhi, T., Koorbanally, N. A., Mudau, F. N., Cáceres, E. A., Popa, D. G., Călina, D. C., & Sharifi‐Rad, J. (2023) · Chemistry & Biodiversity · doi:10.1002/cbdv.202301263 · Cited by 37
Voltammetric determination of harmaline in natural food products using boron-doped diamond electrode
Švorc, Ĺ., Cinková, K., Samphao, A., Stanković, D. M., Mehmeti, E., & Kalcher, K. (2015) · Journal of Electroanalytical Chemistry · doi:10.1016/j.jelechem.2015.03.004 · Cited by 37
Jimson weed (Datura stramonium L.) alkaloid extracts modulate cholinesterase and monoamine oxidase activities in vitro: possible modulatory effect on neuronal function
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“Furthermore, plant extracts such as from Syrian rue (Peganum harmala) (Herraiz et al. 2010) and Passion flower (Passiflora incarnata) (Dhawan et al.”
Background
Design, synthesis and biological evaluation of hybrids of β-carboline and salicylic acid as potential anticancer and apoptosis inducing agents
Xu, Q., Chen, X., Feng, J., Miao, J., Liu, J., Liu, F.-T., Niu, B.-X., Cai, J., Huang, C., Zhang, Y., et al. (2016) · Scientific Reports · doi:10.1038/srep36238 · Cited by 37
Climatic Zone and Soil Properties Determine the Biodiversity of the Soil Bacterial Communities Associated to Native Plants from Desert Areas of North-Central Algeria
Bona, E., Massa, N., Toumatia, O., Novello, G., Cesaro, P., Todeschini, V., Boatti, L., Mignone, F., Titouah, H., Zitouni, A., et al. (2021) · Microorganisms · doi:10.3390/microorganisms9071359 · Cited by 37
Harmine treatment enhances short-term memory in old rats: Dissociation of cognition and the ability to perform the procedural requirements of maze testing
Mennenga, S. E., Gerson, J. E., Dunckley, T. L., & Bimonte‐Nelson, H. A. (2014) · Physiology & Behavior · doi:10.1016/j.physbeh.2014.09.001 · Cited by 36
Peganumine B-I and two enantiomers: new alkaloids from the seeds of Peganum harmala Linn. and their potential cytotoxicity and cholinesterase inhibitory activities
Yang, Y.-D., Cheng, X.-M., Liu, W., Han, Z.-Z., Chou, G., Wang, Y., Sun, D., Wang, Z., & Wang, C. (2016) · RSC Advances · doi:10.1039/c6ra00086j · Cited by 36
Inhibition of the bioactivation of the neurotoxin MPTP by antioxidants, redox agents and monoamine oxidase inhibitors
Herraiz, T., & Guillén, H. (2011) · Food and Chemical Toxicology · doi:10.1016/j.fct.2011.04.026 · Cited by 38
Evaluation of Antidiabetic and Antihyperlipidemic Effects of Peganum harmala Seeds in Diabetic Rats
Komeili, G., Hashemi, M. M., & Bameri-Niafar, M. (2016) · Cholesterol · doi:10.1155/2016/7389864 · Cited by 36
Synthesis, biological evaluation and molecular modeling studies of imidazo[1,2- a ]pyridines derivatives as protein kinase inhibitors
Lawson, M., Rodrigo, J., Baratte, B., Robert, T., Delehouzé, C., Lozach, O., Ruchaud, S., Bach, S., Brion, J., Alami, M., et al. (2016) · European Journal of Medicinal Chemistry · doi:10.1016/j.ejmech.2016.07.040 · Cited by 36
Alkaloids of Peganum harmala: Anticancer Biomarkers with Promising Outcomes
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Antitumor quinazoline alkaloids from the seeds ofPeganum harmala
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Pharmacological and Phytochemical Appraisal of Selected Medicinal Plants from Jordan with Claimed Antidiabetic Activities
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“ACE-inhibitory activity [367, 368] and inhibition of human monoamine oxidase (MAO) [369].”
Background
Analytical techniques for the determination of tryptamines and β‐carbolines in plant matrices and in psychoactive beverages consumed during religious ceremonies and neo‐shamanic urban practices
Gaujac, A., Navickiene, S., Collins, M. I., Brandt, S. D., & de Andrade, J. B. (2012) · Drug Testing and Analysis · doi:10.1002/dta.1343 · Cited by 40
Design, synthesis, and biological evaluation of harmine derivatives as topoisomerase I inhibitors for cancer treatment
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Stimulation, protection and regeneration of dopaminergic neurons by 9-methyl-β-carboline: a new anti-Parkinson drug?
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Desmodeleganine, a new alkaloid from the leaves of Desmodium elegans as a potential monoamine oxidase inhibitor
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“Monoamine oxidase (MAO) is a mitochondrial enzyme that catalyzes the oxidative deamination of biogenic amines and neurotransmitters [1].”
Background
Alkaloids as Potential Multi-Target Drugs to Treat Alzheimer's Disease
Lima, J. A., & Hamerski, L. (2018) · Studies in natural products chemistry · doi:10.1016/b978-0-444-64183-0.00008-7 · Cited by 34
Peganum spp.: A Comprehensive Review on Bioactivities and Health‐Enhancing Effects and Their Potential for the Formulation of Functional Foods and Pharmaceutical Drugs
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Mineral composition, content of phenolic compounds and in vitro antioxidant and antibacterial activities of aqueous and organic extracts of the seeds of Peganum harmala L.
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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.
ORCID: Herraiz, T.
Arán, V.J.
Guillén, H.
Venue: Food and Chemical Toxicology
Publisher: Elsevier BV
Published: 2010-03
Volume: 48
Issue: 3
Pages: 839-845
ISSN: 0278-6915 (ISSN-L)
DOI: 10.1016/j.fct.2009.12.019
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
Licence: www.elsevier.com/tdm/userlicense/1.0/ (tdm)
www.elsevier.com/legal/tdmrep-license (tdm)
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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β-Carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO)

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