The DOI matches its Crossref record; 58 of the 59 references it cites were found in a registry or an index.
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.
Overview
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
In the citing paper
“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
Flagged first, then by citations
1 of the 59 references couldn’t be matched to a known paper.
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
Cited by
Sorted by citations
Pharmacological and therapeutic effects of Peganum harmala and its main alkaloids
Moloudizargari, M., Mikaili, P., Aghajanshakeri, S., Asghari, M. H., & Shayegh, J. (2013) · Pharmacognosy Reviews/Bioinformatics Trends/Pharmacognosy review · doi:10.4103/0973-7847.120524 · Cited by 384
“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.”
BackgroundInfluentialPatel, K., Gadewar, M. M., Tripathi, R. K. P., Prasad, S., & Patel, D. K. (2012) · Asian Pacific Journal of Tropical Biomedicine · doi:10.1016/s2221-1691(12)60116-6 · Cited by 267
The therapeutic potentials of Ayahuasca: possible effects against various diseases of civilization
Frecska, E., Bokor, P., & Winkelman, M. (2016) · Frontiers in Pharmacology · doi:10.3389/fphar.2016.00035 · Cited by 242
“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).”
BackgroundAyahuasca: pharmacology, neuroscience and therapeutic potential
Domínguez-Clavé, E., Soler, J., Elices, M., Pascual, J. C., Álvarez, E., de la Fuente Revenga, M., Friedlander, P., Feilding, A., & Riba, J. (2016) · Brain Research Bulletin · doi:10.1016/j.brainresbull.2016.03.002 · Cited by 226
“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).”
BackgroundDai, J., Dan, W., Schneider, U., & Wang, J. (2018) · European Journal of Medicinal Chemistry · doi:10.1016/j.ejmech.2018.08.027 · Cited by 181
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
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
