Identification of Pavinane Alkaloids in the Genera Argemone and Eschscholzia by GC-MS

Cahlíková, Lucie; Kučera, Radim; Hošťálková, Anna; Klimeš, Jiřı́; Opletal, Lubomı́r

doi:10.1177/1934578x1200701008

Cited by 5 publications

(3 citation statements)

References 13 publications

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“…Column chromatography (CC) and subsequent preparative thin-layer chromatography (TLC) led to the isolation of seven compounds ( 1 – 7 ) belonging to pavine, protopine and benzylisoquinoline structural types. The chemical structures of the isolated alkaloids were elucidated by means of optical rotation, spectroscopic ( 1 H- and 13 C-NMR) and spectrometric (GC-MS, ESI) analyses and by comparison of the obtained data with those in the literature [ 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 38 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 ]. The compounds were determined as (+)-laudanosine ( 1 ), protopine ( 2 ), (–)-argemonine ( 3 ), allocryptopine ( 4 ), (–)-platycerine ( 5 ), (–)-munitagine ( 6 ) and (–)-norargemonine ( 7 ) ( Figure 1 ).…”

Section: Resultsmentioning

confidence: 99%

Cholinesterase and Prolyl Oligopeptidase Inhibitory Activities of Alkaloids from Argemone platyceras (Papaveraceae)

et al. 2017

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Alzheimer’s disease is an age-related, neurodegenerative disorder, characterized by cognitive impairment and restrictions in activities of daily living. This disease is the most common form of dementia with complex multifactorial pathological mechanisms. Many therapeutic approaches have been proposed. Among them, inhibition of acetylcholinesterase, butyrylcholinesterase, and prolyl oligopeptidase can be beneficial targets in the treatment of Alzheimer’s disease. Roots, along with aerial parts of Argemone platyceras, were extracted with ethanol and fractionated on an alumina column using light petrol, chloroform and ethanol. Subsequently, repeated preparative thin-layer chromatography led to the isolation of (+)-laudanosine, protopine, (–)-argemonine, allocryptopine, (–)-platycerine, (–)-munitagine, and (–)-norargemonine belonging to pavine, protopine and benzyltetrahydroisoquinoline structural types. Chemical structures of the isolated alkaloids were elucidated by optical rotation, spectroscopic and spectrometric analysis (NMR, MS), and comparison with literature data. (+)-Laudanosine was isolated from A. platyceras for the first time. Isolated compounds were tested for human blood acetylcholinesterase, human plasma butyrylcholinesterase and recombinant prolyl oligopeptidase inhibitory activity. The alkaloids inhibited the enzymes in a dose-dependent manner. The most active compound (–)-munitagine, a pavine alkaloid, inhibited both acetylcholinesterase and prolyl oligopeptidase with IC50 values of 62.3 ± 5.8 µM and 277.0 ± 31.3 µM, respectively.

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Section: Resultsmentioning

confidence: 99%

Cholinesterase and Prolyl Oligopeptidase Inhibitory Activities of Alkaloids from Argemone platyceras (Papaveraceae)

et al. 2017

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“…(106) Six structural types (pavinane, protopine, benzylisoquinoline, benzophenanthridine, aporphine and protoberberine) were identified in 3 Argemone and 4 Eschscholtzia species. (107) Protoberberine and quaternary benzo[c]phenanthridine BIAs were identified from Chelidonium, (108,109) as well as lignanamides. Besides the above alkaloids, gypsogenin containing pentacyclic triterpene saponin, flavonoids, and megastigmoids were isolated from Hylomecon.…”

Section: P a P A V E R O I D E A E : C H E L I D O N I E A E G L A U...mentioning

confidence: 99%

Mining Therapeutic Efficacy from Treasure Chest of Biodiversity and Chemodiversity: Pharmacophylogeny of Ranunculales Medicinal Plants

Hao

Zheng

et al. 2022

Chin. J. Integr. Med.

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Ranunculales is an order of angiosperms, containing 7 families, i.e., Ranunculaceae (at least 50 genera, >2,000 species), Berberidaceae (17 genera, 650 species), Menispermaceae (65 genera, >350 species), Lardizabalaceae (9 genera, 50 species), Circaeasteraceae (2 species), Papaveraceae (38 genera, >700 species), and Eupteleaceae (2 species, Appendix 1). Ranunculales belongs to the basal eudicots, in which it is the most basal clade; its widely known members include poppies, barberries, monseed, akebia and buttercupss. The chemodiversity of Ranunculaceae, the fl agship family of Ranunculales, and their correlation with the biodiversity and pharmacotherapy, have been systematically reviewed by us in the context of pharmacophylogeny. (1) In recent years, the research enthusiasm for the other 4 major Ranunculales families has been growing rapidly, as plants of these families also meet human needs for food, fl avours, fragrances, and not the least, medicines during long history. Ranunculales plants form the basis of sophisticated traditional medicine systems, e.g., Chinese medicine (CM) and Ayurveda medical system. (2) These systems of medicine give rise to some important Ranunculalesbased drugs still in use today. (3,4) According to incomplete statistics, 573 Ranunculaceae and 308 Berberidaceae species were in medicinally hot nodes; (4) the therapeutic efficacy of 2 families differed substantially. For instance, up to 361 Chinese Ranunculaceae species are used against musculoskeletal diseases, followed by 321 against hepatic diseases, 242 against circulatory diseases, and 210 against skin diseases, etc.; in contrast, as many as 251 Chinese Berberidaceae species are used against eyesight diseases, followed by 249 against hepatic diseases, 242 against digestive diseases and 90 against oral diseases, etc. Nevertheless, except Ranunculaceae, the

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“…Ambas plantas fueron descritas por Carlos Linneo, botánico sueco. En la planta están presentes alcaloides isoquinolínicos 9,13 como la sanguinarina 14 .…”

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Risks of herbalism: a case report of Mexican poppy (Argemone mexicana L) induced liver toxicity

Meléndez¹

2013

Medwave

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The increasing consumption of alternative medicines has lead to a greater awareness about the deleterious effects and interactions that these products can induce. Consequently, medical literature reports liver toxicity from Aloe, Camellia sinensis (green tea), Rhammus purshianus, Aesculus hippocastanum (buckeye) and Valeriana officinalis (valerian), among others. This article reports a female patient who twice consumed Mexican poppy (Argemone mexicana L) with a one-year interval between ingestions. Both times she developed diarrhea, jaundice and general malaise with impaired liver function tests. Other causes of liver disease were ruled out. Questionnaires were used to assess the possibility of drug-induced liver damage. Clinical information was collected from the patient’s medical record and the literature on the subject was reviewed. We conclude that, at least in this case, the most likely cause of liver toxicity was Argemone mexicana L consumption

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Identification of Pavinane Alkaloids in the Genera Argemone and Eschscholzia by GC-MS

Cited by 5 publications

References 13 publications

Cholinesterase and Prolyl Oligopeptidase Inhibitory Activities of Alkaloids from Argemone platyceras (Papaveraceae)

Cholinesterase and Prolyl Oligopeptidase Inhibitory Activities of Alkaloids from Argemone platyceras (Papaveraceae)

Mining Therapeutic Efficacy from Treasure Chest of Biodiversity and Chemodiversity: Pharmacophylogeny of Ranunculales Medicinal Plants

Risks of herbalism: a case report of Mexican poppy (Argemone mexicana L) induced liver toxicity

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