Tropane alkaloids from a Brazilian bark traded as "Catuaba"

Sabine Glasl,Ernst Haslinger,Armin Presser,Johann Jurenitsch,Ingrid Werner

doi:10.3797/scipharm.aut-03-12

Sabine Glasl, Ernst Haslinger + Show 3 more

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https://doi.org/10.3797/scipharm.aut-03-12

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Abstract

Dichloromethane extracts of a Brazilian bark assigned as Anemopaegma mirandum contained four tropane alkaloids. MS-, UV-, IR-, 1H NMR-data and specific optical rotation allowed the identification of catuabin C and its 7-exo-hydroxy-20-methyl-derivative. As no alkaloids are described for Anemopaegma these results indicate heterogeneity for the investigated drug and require a further review.

Highlights

The Brazilian bark Catuaba is known as tonic, stimulant and aphrodisiac
Tropane alkaloids are described for several families (Solanaceae, Erythroxylaceae, Proteaceae, Euphorbiaceae, Rhizophoraceae, Convolvulaceae, Cruciferae) [4]
Catuabin C is known for Erythroxylum vacciniifolium [5,6] and the investigation of "Erythroxylum catuaba" showed similar alkaloids [7]

Summary

Introduction

The Brazilian bark Catuaba is known as tonic, stimulant and aphrodisiac. Its long tradition in folk medicine and the increasing popularity in Europe raise the question concerning the active compounds. Stationary phase: ~ i ~ h r o s ~ h e r @ 1 0 0 - ~ ~ 8 5pm (4x250mm); mobile phase: methanol-water, start from 20% up to 80% methanol in 90 minutes, rate: O,G%/min, flow: Iml/min; UV spectra were recorded on-line in methanol-water by diode array detection during the HPLC runs. CImode: ion source: 180°C, 200eV; reactant gas: ammonia 2.6 (compound I ) , isobutane 3.5 (compound 2), pre-pressure: 2 bar; vacuum: 5 x torr; scan: 4050012s; heating rate of sample vial: 8O0C1min. 'H NMR (400 MHz, acetone-d~)3: .313.35 (m, H-1), 5.17 (t, J = 5.1 Hz, H-3), 3.25 (s br, H-5), 5.77 (dd, J = 7.5, 3.1 Hz, H6), 2.20-2.27 (m, H-7,), 2.68 (dd, J = 13.8, 7.5 Hz, H-7,,,do), 2.53 (s, CH3-8), 3.94 (s, CH3-14), 10.91 (s br, H-20). Rel. int.): 264 [MI' (14.9), 249 [M- CH3]' (11.9), 220 (4.3), 140 [M-(N-CH3-pyrrolCOO)]' (25.4), 137 (9.2), 122 (5.2), 113 (12.7), 110 [pyrrol-COO]' (4.9), 108 [NCH3-pyrrol-CO]' (17.3), 94 [pyrrol-CO]' (100.0), 81 [N-CH3-pyrrol]'(5.2)

Results

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Conclusion