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            ‐Anatabin, ein neues Tabakalkaloid (XI. Mitteil. über Tabak‐Basen)

Späth, Ernst; Kesztler, Friederike

doi:10.1002/cber.19370700215

Cited by 18 publications

(4 citation statements)

References 8 publications

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“…36 , 48 This alkaloid was first isolated from the leaves of N. tabacum by Spath and Kesztler in 1937, who also established the chemical structure through total synthesis. 49 Anatabine is a pyridine-dihydropyridine structurally related to anabasine. 48 Subsequent studies reported that anatabine exists as an 85:15 scalemic mixture of (−)- and (+)-enantiomers in Nicotiana species.…”

Section: Plant-derivedmentioning

confidence: 99%

Pyridine alkaloids with activity in the central nervous system

Lin

Curtis

Sperry

2020

Bioorganic & Medicinal Chemistry

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Section: Plant-derivedmentioning

confidence: 99%

Pyridine alkaloids with activity in the central nervous system

Lin

Curtis

Sperry

2020

Bioorganic & Medicinal Chemistry

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“…Complete concentration-response curves for the stimulation of human α4β2 nAChRs are shown in Figure 2. Table 1 provides efficacy (current response, Imax) and potency (EC50, the concentration Over a century ago, anatabine was isolated from tobacco leaves, and its structure reported by Spath's laboratory [32]. It is the most abundant minor alkaloid in tobacco, representing about 4% of the alkaloids present in tobacco leaves; nicotine represents >90% of the alkaloids present [33].…”

Section: Experiments With Human Nachrs Expressed In Xenopus Oocytesmentioning

confidence: 99%

A Pharmacological Comparison of Two Isomeric Nicotinic Receptor Agonists: The Marine Toxin Isoanatabine and the Tobacco Alkaloid Anatabine

et al. 2020

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Many organisms possess "secondary" compounds to avoid consumption or to immobilize prey. While the most abundant or active compounds are initially investigated, more extensive analyses reveal other "minor" compounds with distinctive properties that may also be of biomedical and pharmaceutical significance. Here, we present an initial in vitro investigation of the actions of two isomeric tetrahydropyridyl ring-containing anabasine analogs: isoanatabine, an alkaloid isolated from a marine worm, and anatabine, a relatively abundant minor alkaloid in commercial tobacco plants. Both compounds have a double bond that is distal to the piperidine ring nitrogen of anabasine. Racemic isoanatabine and anatabine were synthesized and their S-and R-enantiomers were isolated by chiral high pressure liquid chromatography (HPLC). Both isoanatabines displayed higher efficacies at α4β2 nicotinic acetylcholine receptors (nAChRs) relative to the anatabines; R-isoanatabine was most potent. Radioligand binding experiments revealed similar α4β2 nAChR binding affinities for the isoanatabines, but R-anatabine affinity was twice that of S-anatabine. While the two anatabines and S-isoanatabine were highly efficacious agonists at α7 nAChRs, R-isoanatabine was only a weak partial agonist. The four compounds share an ability to stimulate both α4β2 and α7 nAChRs, a property that may be useful in developing more efficacious drugs to treat neurodegenerative and other medical disorders.

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“…It is thought that nicotimine must have been an impure specimen, since of all the alkaloids so far isolated, none has properties resembling those of this substance. One of the bases into which nicotein had been separated was similar to anatabine (3', 4'-dehydroanabasine), also isolated later from an extract of tobacco (321), and it was shown that nicotein was, in fact, a mixture of nornicotine and anatabine (315). A specimen of nicotelline (205) was shown by semimicro oxidation and paper chromatography to be 2,4-di(3-pyridyl)pyridine ( 146), the investigators being of the opinion that the original was not a laboratory artefact, since 4,3' linkages are absent in the other tobacco alkaloids.…”

Section: Phenols Of Tobacco Smokementioning

confidence: 99%