Luminescence spectra of yohimbine, reserpine and related alkaloids

Savory, B.; Turnbull, J. H.

doi:10.1016/0047-2670(83)80059-8

Cited by 15 publications

(10 citation statements)

References 6 publications

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“…1 Two major classes of alkaloids can be identified in such plants: reserpine-like and yohimbine-like indole alkaloids. 2 Reserpine and rescinnamine are the two principal components of the reserpine class, and are known to have potent transquilizer, sedative and antihypertensive actions. 3 Yohimbine and its stereoisomers have important selective α-adrenergic blocker properties, and have been employed for the treatment of male impotency and arteriosclerosis.…”

Section: Introductionmentioning

confidence: 99%

Spectrophotometric Determination of Rauwolfia Alkaloids: Estimation of Reserpine in Pharmaceuticals

2004

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Section: Introductionmentioning

confidence: 99%

Spectrophotometric Determination of Rauwolfia Alkaloids: Estimation of Reserpine in Pharmaceuticals

2004

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“…The reaction under blue LED irradiation proceeded more slowly,w ith 83 %c onversion after 150 min, and with as ignificant shift of selectivity towards 7 (Table 1, entry 5). If we employedt he longwave-absorbing 9,10-anthraquinones A-D as photocatalystsi nt he reaction, we were pleased to observe ag eneral increase in selectivity in favor of desired product 6 (Table 1, entries [6][7][8][9][10][11][12]. We identified 1,5-diaminoanthraquinone C as the optimal catalyst, and by using blue LED irradiation for 150 min with catalyst quantities of 1-3 mol %i nM eCN, compound 6 was isolated in yields of 60-63 %a fter chromatography,a sasingle stereoisomer ( Table 1, entries 11 and 12).…”

Section: Resultsmentioning

confidence: 99%

Visible‐Light Catalytic Photooxygenation of Monoterpene Indole Alkaloids: Access to Spirooxindole‐1,3‐oxazines

Drathen

Hoffmann

Brasholz

2018

Chemistry A European J

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Few natural oxindole alkaloids possess an exceptional spiro-[(1,3)oxazinan-3,6'-oxindole] core structure, which results from an unusual oxidative indole rearrangement. The Rauvolfia alkaloid reserpine can be converted into the spirooxindole-1,3-oxazines dioxyreserpine and trioxyreserpine through efficient visible-light catalytic photooxygenation with anthraquinone photocatalysts. A mechanistic investigation sheds new light on the photooxidative rearrangement of reserpine and related monoterpene indole alkaloids, and the spirooxindole-1,3-oxazine products can be valorized by reductive ring opening, to obtain cis-decahydroisoquinolines as new enantiopure synthetic building blocks, as demonstrated for dioxyreserpine.

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“…In view of their pharmaceutical and therapeutic value, the attention paid these natural compounds has increased. Significant indole alkaloids include the antihypertensive drugs deserpidine and reserpine (Kossover and Goldman 1962;Leon, Belle, and Halpern 1962;Savory and Turnbull 1983) and the vasodilating agent ajmalicine. Ajmalicine is used to combat heart arrhythmias and to improve blood circulation in the brain (Almagro, López Perez, and Pedreno 2011), and also can be used as a precursor of other drugs (Forni 1979).…”

Section: Introductionmentioning

confidence: 99%

Determination of Indole Alkaloids by High-Performance Liquid Chromatography with Resonance Rayleigh Scattering Detection

Peng

Tang

et al. 2015

Analytical Letters

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A novel resonance Rayleigh scattering (RRS) detection approach combined with highperformance liquid chromatography (HPLC) was developed for the determination of reserpine, deserpidine, and ajmalicine. The resonance Rayleigh scattering signal increased when the analytes were bound to diiodofluorescein in Britton-Robinson buffer (pH 4.2). Separation was performed using a C18 column with a mobile phase consisting of acetonitrile-5 millimolar ammonium acetate buffer at pH 4.2 (44:56, volume by volume). Resonance Rayleigh scattering was measured at excitation and emission wavelengths of 320 nanometers. The experimental parameters affecting the separation and the scattering intensity were carefully optimized. Possible mechanisms for the resonance Rayleigh scattering enhancement of the indole alkaloid-diiodofluorescein system were explored by scanning electron microscopy, nuclear magnetic resonance, and ultraviolet-visible absorption spectroscopy. The method was employed for the determination of the analytes in human urine and pharmaceutical tablets.

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Luminescence spectra of yohimbine, reserpine and related alkaloids

Cited by 15 publications

References 6 publications

Spectrophotometric Determination of Rauwolfia Alkaloids: Estimation of Reserpine in Pharmaceuticals

Spectrophotometric Determination of Rauwolfia Alkaloids: Estimation of Reserpine in Pharmaceuticals

Visible‐Light Catalytic Photooxygenation of Monoterpene Indole Alkaloids: Access to Spirooxindole‐1,3‐oxazines

Determination of Indole Alkaloids by High-Performance Liquid Chromatography with Resonance Rayleigh Scattering Detection

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