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.

doi:10.1016/j.fct.2009.12.019

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

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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The β-carboline alkaloids of ayahuasca act as selective, reversible MAO-A inhibitors with almost no effect on MAO-B.
“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

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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: Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › 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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