Phenylpentenylamines from Catha edulis

Brenneisen, Rudolf; Geisshüsler, S.

doi:10.1021/np50054a041

Cited by 20 publications

(4 citation statements)

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“…[ 7 ] Apart from the main effect, it also holds effects on the cardiovascular system including augmentation of blood pressure, vasoconstriction, and an increase in heart rate. [ 8 9 ] Khat has been found to increase the body temperature and has analgesic properties and antimicrobial activity. Apart from these pharmacological properties, khat also exerts some toxicological or adverse effects such as producing central nervous system-related hallucinations, increased states of paranoia, aggression, and dependence.…”

Section: Introductionmentioning

confidence: 99%

Catha edulis extract induces H9c2 cell apoptosis by increasing reactive oxygen species generation and activation of mitochondrial proteins

et al. 2016

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Background:Catha edulis (Khat) is an evergreen shrub or small tree, traditionally used by various peoples of the Arabian Peninsula and Africa as an integral component of the socioeconomic traditions. It is believed that the psychostimulant nature and toxic nature of khat is primarily due to the presence of cathinone and cathine respectively. Studies have shown that khat chewing is closely associated with cardiac complications, especially myocardial infarction. Hence in this study, we exposed cathine-rich khat extract in a cardiomyoblast H9c2 (2-1) cell line to check the cell death mechanism.Materials and Methods:Extraction of Catha edulis leaves was done and the presence of cathine was confirmed with LC-MS-MS. The anti-proliferative activity was assayed using MTT and apoptosis detection by acridine orange/propidium iodide assay. The expression of Bcl-2 and Bax protein and caspase-3/7 expression were analyzed. The level of reactive oxygen species generation was also evaluated.Results:The khat extract showed an IC50 value of 86.5 μg/ml at 48 hours treatment. We have observed significant early apoptosis events by intervened acridine orange within the fragmented DNA with bright green fluorescence upon treatment. The Bcl-2 expression in the treatment with IC50 concentration of khat extract for 24, 48 and 72 hours of incubation significantly decreased with increase in bax level. The increased activation of caspase-3/7 was significantly observed upon treatment together with significant increase of ROS was detected at 24 and 48 hours treatment.Conclusion:Collectively, our results provide insight into the mechanisms by which Catha edulis leaves mediate cell death in cardiomyocytes.SUMMARY Catha edulis (Khat) is an evergreen psychotropic shrub or small treeExtraction of khat leaves was done and the presence of cathine was confirmed with liquid chromatography-mass spectrometry-mass spectrometryThe khat extract showed an IC50 value of 86.5 μg/ml at 48 h treatment in H9c2 (2–1) cell lineThe observed cell death was associated with increased expression of Bcl2 and caspase-3Significant increase of reactive oxygen species was also detected in the cell with treatment. Abbreviations used: CNS: central nervous system; AMI: acute myocardial infarction; TLC: thin layer chromatography; ESI: electrospray ionization; FBS: fetal bovine serum; DMSO: dimethylsulfoxide; AO; acridine orange; PI; propidium iodide; HRP: horseradish peroxidase; HBSS: hank's balanced salt solution; DCFH-DA: 2’,7’-dichlorofluorescin diacetate; NAC, 10 mM: NAC: N-acetyl cysteine; ROS: reactive oxygen species.

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Section: Introductionmentioning

confidence: 99%

Catha edulis extract induces H9c2 cell apoptosis by increasing reactive oxygen species generation and activation of mitochondrial proteins

et al. 2016

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“…When the leaves are dried, the process is accelerated. As a result, only freshly picked khat leaves are fully efficacious (6,7). Fresh khat contains 36-343 mg of cathinone on average (8,9), as well as 83-120 mg of cathine and 8-47 mg of norephedrine per 100 g of leaves (8).…”

Section: Chemical Composition Of Khatmentioning

confidence: 99%

“…The OSSS-3 consists of three questions that inquire about the number of close confidants, the sensation of care from others, and the connection with neighbors, with an emphasis on the availability of practical assistance. The sum scores were categorized as poor (3)(4)(5)(6)(7)(8), moderate (9)(10)(11) and strong (12-14). The OSSS-3 has good predictive and convergent validity (68).…”

Section: Social Supportmentioning

confidence: 99%

Individual and community-level factors associated with khat (Catha edulis) use among women of reproductive age in Halaba zone, South Ethiopia: a multilevel mixed effect analysis

Wogayehu,

Demissie,

Wolka

et al. 2024

Front. Psychiatry

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IntroductionThere is a paucity of data on factors associated with khat chewing among women of reproductive age using multilevel analysis. Furthermore, the effects of some potential factors like stressful life events, knowledge about and attitude toward the effects of khat have been given little attention and are not well understood. Therefore, this study aimed to examine the prevalence and multilevel factors associated with khat use among women of reproductive age in Halaba zone, South Ethiopia.MethodsA community-based cross sectional study was conducted in Halaba zone from February to July, 2023. Systematic random sampling technique was used to include 1573 study participants. The dependent variable was current khat use, which is operationalized as using khat within 30 days preceding the study. An interviewer administered questionnaire was used for the data collection.ResultsThe prevalence of current khat use among women of reproductive age was 65.9% [95%CI (63.5-68.2%)]. Factors significantly associated with khat use were; ages of women 35 and above years [Adjusted Odds Ratio (AOR) = 6.35, 95% CI: (3.62, 11.13)], ever married [AOR = 2.41, 95% CI: (1.10, 5.31)], secondary and above education [AOR = 0.28, 95% CI: (0.15, 0.49)], belong to richer household [AOR = 1.75, 95% CI: (1.12, 2.75)], mass media use [AOR = 3.12, 95% CI: (1.85, 4.81)], low knowledge about khat effects [AOR = 3.12, 95% CI: (1.85, 5.24)], positive attitude towards khat use [AOR = 11.55, 95% CI: (6.76, 19.71)], and strong social support [AOR = 0.43, 95% CI: (0.28, 0.64)] and non-user friend [AOR = 0.31, 95% CI: (0.20, 0.48)]. From the community level variables: rural residence [AOR = 5.06, 95% CI: (1.82, 14.09)] was significantly associated with khat use.ConclusionKhat use among women of reproductive age was found to be very high. From individual-level factors: advanced ages of women, secondary and above education, live in the richer wealth quintile, mass media exposure, low knowledge on khat effects, positive attitude towards khat use, strong social support, and from community-level variables: residing in rural area were significantly associated with khat use. Khat use screening for all women of childbearing age, as well as referral to substance use disorder centers for those women identified as having khat use disorder, should become a standard of care in all health facilities.

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“…During chewing, over 90% of the alkaloids are released from Khat 15 and can be well absorbed through the oral mucosa with absorption efficiencies of 60% and 80% for cathinone and cathine, respectively. 21 In addition to these major principles, other classes of alkaloids can be also detected, notably merucathinone (5), pseudomerucathine (6), merucathine (7) 22 and the complex cathedulin alkaloids. 23 Related to Khat natural products are the synthetic cathinone analogues, notably methylone (8), methcathinone (9), mephedrone (4-methylmethcathinone) (10) and methedrone (4methoxymethcathinone) (11).…”

Section: Introductionmentioning

confidence: 99%

Natural product ‘legal highs’

Arunotayanun¹,

Gibbons²

2012

Nat. Prod. Rep.

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The last five years have seen a dramatic increase in the global popularity of 'Legal Highs', often referred to as Novel Psychoactive Substances (NPS). These materials are single chemicals, plant or fungal materials or their extracts, which may be purchased and possessed without legal restriction in certain countries. The single chemical entity drugs are often closely structurally related to existing controlled drugs of abuse from, for example, the amphetamine (phenethylamine), cannabinoid-mimetic or tryptamine classes, whereas the natural products are from plant or fungal materials that have a long history of pharmacognosy. These natural product legal highs are by their very nature highly chemically complex, and in the clear majority of cases, chemical studies were conducted some considerable time ago. Their pharmacology and toxicology generally focuses on the major active principles with few studies detailing the potentially highly complicated and multiple effects of their extracts. This complexity, coupled with the inherent natural product variability of plant and fungal species, adds a further dimension to the potential harms associated with natural product legal high use. This review encompasses the most popular current legal highs and describes their basic chemistry, usage and preparation, pharmacology, toxicology and discusses the issues surrounding the complexity of these materials, and how this can impact on the evaluation of their harms.

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Phenylpentenylamines from Catha edulis

Cited by 20 publications

References 3 publications

Catha edulis extract induces H9c2 cell apoptosis by increasing reactive oxygen species generation and activation of mitochondrial proteins

Catha edulis extract induces H9c2 cell apoptosis by increasing reactive oxygen species generation and activation of mitochondrial proteins

Individual and community-level factors associated with khat (Catha edulis) use among women of reproductive age in Halaba zone, South Ethiopia: a multilevel mixed effect analysis

Natural product ‘legal highs’

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