Tropane alkaloids

Fodor, G.; Dharanipragada, R.

doi:10.1039/np9910800603

Nat. Prod. Rep.

1991

DOI: 10.1039/np9910800603

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Tropane alkaloids

G. Fodor¹,

R. Dharanipragada²

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Cited by 15 publications

(3 citation statements)

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“…The tropane alkaloids occur mainly in the plant families Convolvulaceae, Erythroxylaceae, Proteaceae, Rhizophoraceae, and Solanaceae and occasionally have been reported from plants in the Brassicaceae, Euphorbiaceae, and Olacaceae . Many biological and pharmacological reports on the tropane alkaloids have appeared, particularly concerning the neurochemical and physiological effects of cocaine. , The protective property of atropine against organophosphorus compounds is also well documented . In addition, the therapeutic uses of atropine sulfate as an antisialogogue adjuvant in surgery and as a gastrointestinal antispasmodic are well-known .…”

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“…1 Many biological and pharmacological reports on the tropane alkaloids have appeared, particularly concerning the neurochemical and physiological effects of cocaine. 2,3 The protective property of atropine against organophosphorus compounds is also well documented. 3 In addition, the therapeutic uses of atropine sulfate as an antisialogogue adjuvant in surgery and as a gastrointestinal antispasmodic are well-known.…”

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“…6 In the present follow-up study, the stems of the Caribbean shrub Erythroxylum rotundifolium Lunan (Erythroxylaceae), collected in the Dominican Republic, were investigated. In this paper, we report the cytotoxicity and in vitro multidrug-resistance properties of six tropane alkaloids (1)(2)(3)(4)(5)(6) isolated from this species. Three new alkaloids, 7β-hydroxy-6β- (3,4,5trimethoxybenzoyloxy)-3R-(E)- (3,4,5-trimethoxycinnamoyloxy)tropane ( 1), 6β-benzoyloxy-3R-(Z)- (3,4,5-trimethoxycinnamoyloxy)tropane (2), and the levorotatory enantiomer (-)-6β-benzoyloxy-3R-hydroxytropane (3), were elucidated using spectroscopic methods, together with three known tropane alkaloids identified by comparison with published spectroscopic data, as 6β-benzoyloxy-3R-(E)- (3,4,5-trimethoxycinnamoyloxy)tropane (4), 7,8 6β-benzoyloxy-3R-(E)- (3,4,5trimethoxycinnamoyloxy)tropane-7β-ol (5), 7 and 7β-acetoxy-6β-benzoyloxy-3R-(E)- (3,4,5-trimethoxycinnamoyloxy)tropane (6).…”

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Reversal of Multidrug Resistance by Tropane Alkaloids from the Stems of Erythroxylum rotundifolium

et al. 2002

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Six tropane alkaloid esters were isolated from the stems of Erythroxylum rotundifolium. The structures of three new tropane esters, 7beta-hydroxy-6beta-(3,4,5-trimethoxybenzoyloxy)-3alpha-(E)-(3,4,5-trimethoxycinnamoyloxy)tropane (1), 6beta-benzoyloxy-3alpha-(Z)-(3,4,5-trimethoxycinnamoyloxy)tropane (2), and (-)-6beta-benzoyloxy-3alpha-hydroxytropane (3), were established by spectroscopic techniques. When alkaloids 1-6 were evaluated against a panel of human cancer cell lines, the new compound 6beta-benzoyloxy-3alpha-(Z)-(3,4,5-trimethoxycinnamoyloxy)tropane (2) and three known compounds, 6beta-benzoyloxy-3alpha-(3,4,5-trimethoxycinnamoyloxy)tropane (4), 6beta-benzoyloxy-3alpha-(E)-(3,4,5-trimethoxycinnamoyloxy)tropane-7beta-ol (5), and 7beta-acetoxy-6beta-benzoyloxy-3alpha-(E)-(3,4,5-trimethoxycinnamoyloxy)tropane (6), demonstrated greatest activity with multidrug-resistant oral epidermoid carcinoma (KB-V1) cells incubated in the presence of vinblastine. Thus, tropane esters of this type can reverse the multidrug-resistance phenotype, presumably by interacting with P-glycoprotein.

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Reversal of Multidrug Resistance by Tropane Alkaloids from the Stems of Erythroxylum rotundifolium

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The Distorted Tropane of Scopoline

et al. 2013

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The structural isomerization of scopine into scopoline (oscine) has been observed in a supersonic jet expansion using microwave spectroscopy. The rotational spectrum evidences a single structure in the gas phase, providing a first description of the (three-ring) structurally distorted tropane in scopoline. The absence of rotational signatures of any scopine conformation suggests a practically quantitative isomerization at the vaporization temperatures of the experiment (ca. 90 °C). The determined rotational parameters of scopoline reveal the structural consequences of the intramolecular cyclation of scopine, which breaks the original epoxy group and creates a new ether bridge and a 7β-hydroxytropane configuration. The hydroxy group further stabilizes the molecule by an O-H⋅⋅⋅N intramolecular hydrogen bond, which, in turn, forces the N-methyl group to the less stable axial form. Supporting ab initio (MP2) and DFT (B3LYP, M06-2X) calculations are included.

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Scopine Isolated in the Gas Phase

et al. 2016

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The rotational spectrum of the tropane alkaloid scopine has been detected by Fourier transform microwave spectroscopy in a pulsed supersonic jet. A non-conventional method for bringing the molecules intact into the gas phase was used, mixing scopine syrup with solid glycine powder and vaporizing the solid mixture with an UV ultrafast laser beam. Laser vaporization prevented the easy isomerization to scopoline previously observed when conventional heating. A single conformer was unambiguously observed in the supersonic jet, which corresponds to the energetically most stable species according to quantum chemistry calculations. Rotational and centrifugal distortion constants have been accurately determined. The spectrum reveals hyperfine splittings due to the combined effect of hindered rotation of the methyl group and the presence of a quadrupolar nucleus ( 14 N).This additional information allowed determining the angle of N-methyl inversion between the N-CH3 bond and the bicyclic C-N-C plane (135º), as well as the internal rotation barrier of the methyl group (6.24(1) kJ mol -1 ).

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Tropane alkaloids

Cited by 15 publications

References 23 publications

Reversal of Multidrug Resistance by Tropane Alkaloids from the Stems of Erythroxylum rotundifolium

Reversal of Multidrug Resistance by Tropane Alkaloids from the Stems of Erythroxylum rotundifolium

The Distorted Tropane of Scopoline

Scopine Isolated in the Gas Phase

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