Employing Two‐stage Derivatisation and GC–MS to Assay for Cathine and Related Stimulant Alkaloids across the Celastraceae

Tembrock, Luke R.; Broeckling, Corey D.; Heuberger, Adam L.; Simmons, Mark P.; Stermitz, Frank R.; Uvarov, Jessica M.

doi:10.1002/pca.2671

Cited by 8 publications

(4 citation statements)

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“…The biosynthesis of cathinone and similar stimulant alkaloids is rare among green plants, known only in Catha edulis and several Asian species of Ephedra [ 8 ]. In addition, Celastraceae species produce numerous unique phytochemicals of potential pharmaceutical value [ 9 ]. Chloroplast transformations of qat and related species may prove useful for the production of cathinone related alkaloids and/or novel drugs.…”

Section: Introductionmentioning

confidence: 99%

The Complete Chloroplast Genome of Catha edulis: A Comparative Analysis of Genome Features with Related Species

Tembrock

Zheng³

et al. 2018

IJMS

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Qat (Catha edulis, Celastraceae) is a woody evergreen species with great economic and cultural importance. It is cultivated for its stimulant alkaloids cathine and cathinone in East Africa and southwest Arabia. However, genome information, especially DNA sequence resources, for C. edulis are limited, hindering studies regarding interspecific and intraspecific relationships. Herein, the complete chloroplast (cp) genome of Catha edulis is reported. This genome is 157,960 bp in length with 37% GC content and is structurally arranged into two 26,577 bp inverted repeats and two single-copy areas. The size of the small single-copy and the large single-copy regions were 18,491 bp and 86,315 bp, respectively. The C. edulis cp genome consists of 129 coding genes including 37 transfer RNA (tRNA) genes, 8 ribosomal RNA (rRNA) genes, and 84 protein coding genes. For those genes, 112 are single copy genes and 17 genes are duplicated in two inverted regions with seven tRNAs, four rRNAs, and six protein coding genes. The phylogenetic relationships resolved from the cp genome of qat and 32 other species confirms the monophyly of Celastraceae. The cp genomes of C. edulis, Euonymus japonicus and seven Celastraceae species lack the rps16 intron, which indicates an intron loss took place among an ancestor of this family. The cp genome of C. edulis provides a highly valuable genetic resource for further phylogenomic research, barcoding and cp transformation in Celastraceae.

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Section: Introductionmentioning

confidence: 99%

The Complete Chloroplast Genome of Catha edulis: A Comparative Analysis of Genome Features with Related Species

Tembrock

Zheng³

et al. 2018

IJMS

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“…The main phenylalkylamines are phenylpropylamines consisting of (−)‐cathinone [(S)‐α‐aminopropiophenone] and the two diastereoisomers, (+)‐cathine [(1S) (2S)‐norpseudoephedrine] and (−)‐norephedrine [(1R) (2S)‐norephedrine]. These alkaloids appear to be unique to khat, as they were not detected in about 43 Celastraceae species investigated (Tembrock et al, ). In addition, two oxazolidine derivatives, 2, 4‐dimethyl‐5‐phenyloxazolidine and 4‐methyl‐2‐(trans‐1‐pentenyl)‐5‐phenyloxazolidine have also been identified (Krizevski et al, ).…”

Section: Chemical Constituents Of Khatmentioning

confidence: 99%

Pharmacological and Toxicological Effects of Catha edulis F. (Khat)

Engidawork

2017

Phytotherapy Research

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Khat chewing is deeply rooted in the culture and tradition of communities in khat belt countries, and its consumption is spread to other countries through the suitcase trade. The aim of this article is to review current knowledge on the chemistry, social, pharmacology and toxicology of khat and its use. Khat produces effect invariably in every system, which is harmful or beneficial in some instances. Harmful effects are observed in heavy users, although firm evidence is lacking. Chewing khat acutely elicits states of euphoria, which is followed by low mood. Khat contains alkaloids with psychostimulant properties, but the effect cannot be totally explained by these alkaloids. It is also not clear whether the effect produced in some organs like liver could be attributed to khat or pesticides sprayed during farming. Although the evidence indicates that khat has adverse effects in most organs, our understanding of the complex interaction between use and effect is incomplete, and causal relationships have not yet been described. Moreover, khat has positioned itself well in the social, economic and political arena. Thus, a multidisciplinary research is required to understand the different dimensions and come up with ways that maximize the benefit while minimizing the risk. Copyright © 2017 John Wiley & Sons, Ltd.

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“…Khat leaves contain many various compounds: alkaloids, flavonoids, tannins, glycosides, vitamins, terpenoids, minerals, and more than ten amino acids [12]. Both cathinone and cathine are the most important psychoactive amphetamine-like alkaloids in khat, with the predominant of cathinone in fresh leaves and twigs [13]. The chemical structures of the two alkaloids are shown in Figure 3.…”

Section: Introductionmentioning

confidence: 99%

Khat Chewing and Lipid Profile in Human and Experimental Animals

Al-Duais

Al-Awthan

2021

BioMed Research International

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Background. Catha edulis, also known as khat or qat, is a plant that grows in East Africa and southern Arabia. Several millions of people chew the leaves and twigs of khat plant for their central stimulating amphetamine-like effects. Khat chewing is becoming more common in Europe and the United States, owing to worldwide migration. Objective. This review examines the khat ingredients, global prevalence, and legal status as well as its effects on lipid profile. Methodology. A literature search was performed using PubMed, Scopus, and Google Scholar to collect information within articles published up to April 2021 with the goal of identifying relevant studies. The proposed mechanisms of cathinone effects on total cholesterol and triglyceride were also discussed. Conclusion. The khat chewing habit is considered as a serious economic and health issue that needs specialized programs to assist those people to quit or reducing this habit.

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Employing Two‐stage Derivatisation and GC–MS to Assay for Cathine and Related Stimulant Alkaloids across the Celastraceae

Abstract: These results indicate that cathine is unique to Catha edulis, and not the compound responsible for the stimulant properties reported in related Celastraceae species. Copyright © 2017 John Wiley & Sons, Ltd.

Cited by 8 publications

References 56 publications

The Complete Chloroplast Genome of Catha edulis: A Comparative Analysis of Genome Features with Related Species

The Complete Chloroplast Genome of Catha edulis: A Comparative Analysis of Genome Features with Related Species

Pharmacological and Toxicological Effects of Catha edulis F. (Khat)

Khat Chewing and Lipid Profile in Human and Experimental Animals

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