Structure of brevicolline

Vember, P. A.; Terent'eva, I. V.; Lazur'evskii, G. V.

doi:10.1007/bf00564117

Cited by 3 publications

(10 citation statements)

References 3 publications

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“…1 H NMR, and IR data of our alkaloid match exactly with those reported earlier for 1c [14][15][16]. The melting point and optical rotation, however, differ slightly from literature data.…”

Section: Resultssupporting

confidence: 89%

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Facile and Convenient One-Pot Process for the Synthesis of Spirooxindole Derivatives in High Optical Purity Using (−)-(S)-Brevicolline as an Organocatalyst

et al. 2011

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Abstract:The paper presents an application of the asymmetry approach to spirooxindoles via Brevicolline, Cinchonidine or Cinchonine catalyzed one-pot multicomponent synthesis. Brevicolline, in comparison with Cinchonidine or Cinchonine, catalyzes the reaction of isatins, acetylacetone/ethyl 3-oxobutanoate and malononitrile, with the formation of spiro [oxindole-3,4'-4'H-pirane] derivatives in an optically active form in very good to excellent yields.

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“…1 H NMR, and IR data of our alkaloid match exactly with those reported earlier for 1c [14][15][16]. The melting point and optical rotation, however, differ slightly from literature data.…”

Section: Resultssupporting

confidence: 89%

“…Brevicolline was extracted from Carex brevicollis and purified by crystallization according to [14][15][16]. Dichloromethane was dried and distilled before using.…”

Section: General Datamentioning

confidence: 99%

Facile and Convenient One-Pot Process for the Synthesis of Spirooxindole Derivatives in High Optical Purity Using (−)-(S)-Brevicolline as an Organocatalyst

et al. 2011

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“…Brevicolline possesses the core nicotine structure (Wagner and Comins, 2006) and the base peak (m/e 84; Fig. 2.1) also is observed in the fragmentation of nicotine (Vember et al, 1967). The presence of brevicarine was supported by the findings of Terenteva et al (1969), who located its molecular ion in the mass spectrum at m/e 267.…”

Section: Discussionsupporting

confidence: 52%

“…As standards of brevicolline and brevicarine were not found, and considering that these alkaloids are derivative of harmane (Vember et al, 1967), their quantification was performed using the commercial standard harmaline hydrocloride dihydrate (Sigma). A stock solution of 1 mg harmaline/1 ml methanol was prepared to perform the calibration curve.…”

Section: Methodsmentioning

confidence: 99%

Phenological Changes in the Concentration of Alkaloids of Carex brevicollis in an Alpine Rangeland

et al. 2010

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Carex brevicollis (Cyperaceae) is a plant of mesic grasslands in calcareous mountains of southern Europe. It contains two different β-carboline alkaloids, brevicolline and brevicarine, the first of which is thought to produce abortions in mammals. In the rangeland of Aliva, within the Picos de Europa massif in northern Spain, the abundance of Carex brevicollis has been linked with the occurrence of teratogenesis in early gestating cows grazing in early summer. The concentration of alkaloids was measured in the summers of 2007 and 2008, at intervals of 2 weeks, at different altitudes within the rangeland (1,350, 1,600, and 1,850 m) and from different parts of the sedge (leaves, reproductive stems, and inflorescences). Estimated growing degree days were related to the flowering phenology of Carex brevicollis and were used to analyse its relation with the concentration of alkaloids. Brevicarine concentration was higher in inflorescences and brevicolline in leaves. Although it also depended on the zone and year, the concentrations of both alkaloids were related one to another in leaves and inflorescences but not in stems. Both alkaloids decreased with growing degree days in the inflorescences and showed no response in leaves. Our findings suggest that brevicarine, not brevicolline, could be the teratogen in pregnant cattle in this region. This hypothesis is supported by the observed frequent consumption of inflorescences and scarce consumption of leaves of Carex brevicollis by grazing livestock, and also by the coincidence of the toxicity in early pregnant cows with the flowering time of the sedge.

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“…The β-carboline alkaloid brevicolline ( 1 ), the major alkaloid of the plant Carex brevicollis DC (Cyperacee), belongs to a group of pharmacologically interesting compounds and was isolated, , determined, and chemically modified 30 years ago. Since that time, syntheses of racemic 1 were carried out, for example, by Winterfeldt or Leete, both using tryptamine as starting compound.…”

mentioning

confidence: 99%