☆ 4.2 Review

Alkaloids from the entheogenic plant Peganum harmala

AUSTRALIAN JOURNAL OF CHEMISTRY (2023)

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New β-carboline alkaloids from the seeds of Peganum harmala

Ying Xu et al.

Summary: Two new beta-carboline alkaloids, peganuharmines A and B (1 and 2), along with three known ones (3-5), were isolated from Peganum harmala seeds. The structures and absolute configurations were determined through extensive spectroscopic analyses and quantum chemistry calculations. Alkaloids 1-2 exhibited moderate cytotoxicity against A549 and MCF-7 cell lines.

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ACS CHEMICAL NEUROSCIENCE (2023)

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Agata Zieba et al.

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Psychedelics for the treatment of depression, anxiety, and existential distress in patients with a terminal illness: a systematic review

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Article Clinical Neurology

The epidemiology of mescaline use: Pattern of use, motivations for consumption, and perceived consequences, benefits, and acute and enduring subjective effects

Malin Vedoy Uthaug et al.

Summary: The study found that the majority of English-speaking adults use mescaline infrequently for spiritual exploration or to connect with nature, with low potential for abuse and positive effects on mental health. Most respondents reported improvements in their psychiatric conditions following their most memorable mescaline experience.

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Nan-Xi Li et al.

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Psychedelics: Alternative and Potential Therapeutic Options for Treating Mood and Anxiety Disorders

Henry Lowe et al.

Summary: The word psychedelic originated from ancient Greek and has been used in spiritual and religious rituals in Central and South American cultures for thousands of years. However, with the globalization of these drugs in the 1960s, Western countries implemented strict drug control laws, leading to the criminalization and negative perception of psychedelics. In recent years, there has been growing evidence to suggest the therapeutic potential of psychedelics in treating mood and anxiety disorders, making them an alternative option to traditional treatments.

MOLECULES (2022)

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Article Biochemistry & Molecular Biology

Anti-tumor alkaloids from Peganum harmala

Qin Zhang et al.

Summary: The study isolated over 20 alkaloids from Peganum harmala L., with 3-(4-hydroxyphenyl)quinoline showing potent antiproliferative activity against HepG-2 cell lines.

PHYTOCHEMISTRY (2022)

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Article Plant Sciences

In vitro and in silico inhibition of COX-2 and 5-LOX by beta-carboline alkaloids from the seeds of Peganum harmala L.

Fatma M. Abdel Bar et al.

Summary: Phytochemical investigation of the methanol extract of P. harmala seeds led to the discovery of two new alkaloids and a new semisynthetic derivative, as well as the identification of four known derivatives. These compounds exhibited anti-inflammatory activity and interacted with key residues of specific enzymes.

SOUTH AFRICAN JOURNAL OF BOTANY (2022)

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Article Microbiology

The Antimicrobial Activity and Characterization of Bioactive Compounds in Peganum harmala L. Based on HPLC and HS-SPME-GC-MS

Ningning Wang et al.

Summary: Peganum harmala L. is a perennial herb belonging to the Tribulus family, with its seeds showing higher concentrations of harmine and harmaline compared to aerial parts. The study identified 94 volatile organic compounds in the plant for the first time and found that methanol extracts of seeds exhibited strong antimicrobial activities against various bacterial strains and phytopathogenic fungi. The alkaloids from P. harmala were suggested to be responsible for the antimicrobial activity and could potentially be developed into new antimicrobial drugs.

FRONTIERS IN MICROBIOLOGY (2022)

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Review Neurosciences

The neural basis of psychedelic action

Alex C. Kwan et al.

Summary: This review focuses on the basic neurobiology of the action of psychedelic drugs. It covers the chemistry and potency of psychoactive molecules, the role of serotonin receptors and their signaling pathways, the impact on neuronal spiking dynamics, transcriptional changes, and structural plasticity. This review also summarizes neuroimaging results that highlight the effects on association cortices and thalamocortical functional connectivity, providing insights into the neural mechanisms responsible for the acute and enduring effects of psychedelics on behavior.

NATURE NEUROSCIENCE (2022)

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Article Chemistry, Organic

(±)-Pheharmines A-B, two pairs of racemic alkaloids with a morpholino[4,3,2-hi]β-carboline core, from the roots of Peganum harmala

Sheng-Ge Li et al.

Summary: Two pairs of novel beta-carboline-phenylpropanoid alkaloids with a unique chemical structure and moderate cytotoxic activity were isolated from the roots of Peganum harmala. The structures and configurations were determined by spectroscopic analyses and calculations.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

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Article Medicine, General & Internal

Fatal poisoning of pregnant women by peganum harmala L.: A case reports

El Aidouni Ghizlane et al.

Summary: This case report describes a 20-year-old woman who suffered from acute kidney injury, cerebral ischemia, and bleeding due to intoxication with Peganum harmala L. The patient received early treatment, including intubation, ventilation, symptomatic treatment, and hemodialysis, leading to a favorable outcome with discharge after one and a half months. Doctors should be aware of the signs of P. harmala toxicity and initiate prompt and adequate management to improve prognosis.

ANNALS OF MEDICINE AND SURGERY (2021)

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Article Chemistry, Multidisciplinary

Peganum harmala Alkaloids Self-Assembled Supramolecular Nanocapsules with Enhanced Antioxidant and Cytotoxic Activities

Sherif Ashraf Fahmy et al.

Summary: Amphiphilic macrocycles like p-sulfonatocalix[6]arenes have shown potential in designing synthetic nanovesicles. These nanovesicles can improve drug solubility, stability, and biological activity. Encapsulation of harmala alkaloid-rich fraction (HARF) in p-SC6 nanocapsules significantly increased antioxidant and cytotoxic activities.

ACS OMEGA (2021)

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Extraction and Identification of Chemical Compounds of Peganum harmala L. Seed Essential Oil by HS-SPME and GC-MS Methods

Reza Asadzadeh et al.

Traditional and Integrative Medicine (2021)

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Review Cell Biology

Peganum spp.: A Comprehensive Review on Bioactivities and Health-Enhancing Effects and Their Potential for the Formulation of Functional Foods and Pharmaceutical Drugs

Javad Sharifi-Rad et al.

Summary: The genus Peganum consists of four widely distributed species with Peganum harmala L. being the most studied for its botanical features, geographical distribution, and bioactivities. While these plants are considered to have health-promoting effects, adverse effects have also been noted, requiring further research and exploration.

OXIDATIVE MEDICINE AND CELLULAR LONGEVITY (2021)

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Article Chemistry, Medicinal

Naturalistic Use of Mescaline Is Associated with Self-Reported Psychiatric Improvements and Enduring Positive Life Changes

Gabrielle Agin-Liebes et al.

Summary: Mescaline, a naturally occurring psychoactive alkaloid, has shown potential for mental health benefits with users reporting improvements in conditions like depression, anxiety, PTSD, AUD, and DUD. Those with acute psychological insights during mescaline experiences were more likely to report improvements in mental health conditions like depression, anxiety, AUD, and DUD. Further research is needed to confirm these findings and investigate mescaline's efficacy for psychiatric treatment in controlled clinical trials.

ACS PHARMACOLOGY & TRANSLATIONAL SCIENCE (2021)

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Article Chemistry, Applied

Peganum harmala and its Alkaloids as Dopamine Receptor Antagonists: in Silico Study

Mohammad Rizki Fadhil Pratama et al.

Summary: The study aimed to determine the alkaloid from P. harmala with the highest potential as a dopamine receptor antagonist. Among the known alkaloids, dipegine, harmalanine, and harmalacinine showed the highest potency in terms of both free energy of binding and similarity of ligand-receptor interactions. The investigation anticipates that some alkaloids from P. harmala have the potential as a dopamine receptor antagonist.

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Article Chemistry, Multidisciplinary

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Felix Blei et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

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Article Plant Sciences

Orthoscuticellines A-E, β-Carboline Alkaloids from the Bryozoan Orthoscuticella ventricosa Collected in Australia

Guy Kleks et al.

JOURNAL OF NATURAL PRODUCTS (2020)

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Article Biochemistry & Molecular Biology

A Fast and Reliable UHPLC-MS/MS-Based Method for Screening Selected Pharmacologically Significant Natural Plant Indole Alkaloids

Danuse Tarkowska

MOLECULES (2020)

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Article Chemistry, Organic

β-Carboline Alkaloids from the Seeds of Peganum harmala and Their Anti-HSV-2 Virus Activities

Zhong-Nan Wu et al.

ORGANIC LETTERS (2020)

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Article Chemistry, Organic

Pegaharmols A-B, Axially Chiral β-Carboline-quinazoline Dimers from the Roots of Peganum harmala

Sheng-Ge Li et al.

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Review Biochemistry & Molecular Biology

Understanding Central Nervous System Effects of Deliriant Hallucinogenic Drugs through Experimental Animal Models

Andrey D. Volgin et al.

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Exploration of Indole Alkaloids from Marine Fungus Pseudallescheria boydii F44-1 Using an Amino Acid-Directed Strategy

Mei-Xiang Yuan et al.

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Cytotoxic quinazoline alkaloids from the seeds of Peganum harmala

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Article Chemistry, Medicinal

Racemic indole alkaloids from the seeds of Peganum harmala

Kai-Bo Wang et al.

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Analysis of alkaloids from Peganum harmala L. sequential extracts by liquid chromatography coupled to ion mobility spectrometry

Zhiyan Wang et al.

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Study of Methanol Extracts from Different Parts of Peganum harmala L. Using 1H-NMR Plant Metabolomics

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(±)-Peharmaline A: A Pair of Rare β-Carboline-Vasicinone Hybrid Alkaloid Enantiomers from Peganum harmala

Kai-Bo Wang et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2017)

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Identification, occurrence and activity of quinazoline alkaloids in Peganum harmala

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A review on traditional uses, phytochemistry, pharmacology, pharmacokinetics and toxicology of the genus Peganum

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Structurally Diverse Alkaloids from the Seeds of Peganum harmala

Kai-Bo Wang et al.

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Anti-inflammatory bioactive equivalence of combinatorial components β-carboline alkaloids identified in Arenaria kansuensis by two-dimensional chromatography and solid-phase extraction coupled with liquid-liquid extraction enrichment technology

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Cytotoxic Constituents and Mechanism from Peganum harmala

Chunhua Wang et al.

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Chemical Composition, Antibacterial and Phytotoxic Activities of Peganum harmala Seed Essential Oils from Five Different Localities in Northern Africa

Ida Apostolico et al.

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A Series of β-Carboline Alkaloids from the Seeds of Peganum harmala Show G-Quadruplex Interactions

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Peganumine B-I and two enantiomers: new alkaloids from the seeds of Peganum harmala Linn. and their potential cytotoxicity and cholinesterase inhibitory activities

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Antitumor quinazoline alkaloids from the seeds of Peganum harmala

Chun-Hua Wang et al.

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Potent AChE and BChE inhibitors isolated from seeds of Peganum harmala Linn by a bioassay-guided fractionation

Yadi Yang et al.

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Antitussive, expectorant, and bronchodilating effects of quinazoline alkaloids (±)-vasicine; deoxyvasicine, and (±)-vasicinone from aerial parts of Peganum harmala L

Wei Liu et al.

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Peganumine A, a β-Carboline Dimer with a New Octacyclic Scaffold from Peganum harmala

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Pegaharmalines A and B, two novel beta-carboline alkaloids with unprecedented carbon skeletons from Peganum harmala

Kai-Bo Wang et al.

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Characterization and Determination of Trace Alkaloids in Seeds Extracts from Peganum harmala Linn. Using LC-ESI-MS and HPLC

L. Liu et al.

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Composition and anti-oxidant, anti-cancer and anti-inflammatory activities of Artemisia herba-alba, Ruta chalpensis L. and Peganum harmala L.

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

T. Herraiz et al.

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A case of β-carboline alkaloid intoxication following ingestion of Peganum harmala seed extract

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Alkaloids from the seeds of Peganum harmala showing antiplasmodial and vasorelaxant activities

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