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Isolation and identification of alkaloids from fruits of Berberis thunbergii DC.

B. BRÁZDOVlCOVÁ, Daniela Košťálová, J. Tomko, Hwang Yang Jin

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Abstract

Two major bisbenzylisoquinoline alkaloids, isotetrandrine and berbamine and three protoberberine type alkaloids berberine, palmatine, and jatrorrhizine were isolated from seeds of Berberis thunbergii DC. Berberine and oxyberberine, which is not present in the seeds, were isolated from the pericarp. Identity of the isolated substances was verified by spectral means (i.r., u.V., and mass spectrometry), optical rotation, and comparison with specimens. Из семян растения Berberis thunbergii DC. выделены два главных алкалоида бйсбензилизохинолиновой группы изотетрандрин и бербамин. Из околоплоднико в выделен основной алкалоид третичной фракции оксиберберин, который отсутствует в семенах этого растения и берберин. Из четвертичных оснований выделены из семян берберин, пальматин и ятроррицин. Основания идентифицированы сравнением с истинными образцами и на основании спектральных данных и оптического вращения. Berberine, jatrorrhizine, and aporfine alkaloid magnoflorine were isolated from the underground and aerial parts of this plant together with tertiary bases oxyberberine, berbamine, oxyacanthine, and isotetrandrine [1,2]. The presence of alkaloids in fruits has not been tested so far. From the chemotaxonomic point of view it is important to ascertain the presence of secondary metabolites in the individual parts of the plant and therefore we studied their occurrence in fruits. Alkaloids berberine, berbamine, palmatine, oxyacanthine, jatrorrhizine, magnoflo­ rine, and columbamine are present in most species of the genus Berberis L. Six species, B. vulgaris, B. tschonoskyana , B. lamina, B. laurica, B. amurensis, B. baluchistanica, contain new isoquinoline alkaloids [3]. It has been found that roots and stems of B. oblonga and B. integerrima contain alkaloids in an approximately equal ratio, which is not the case with leaves [4, 5]. Oblongamine, a new type of monoquaternary oxyacanthine type [4] phenolic alkaloid and 2'-N-methylberbamine [5] were found in the portion of tertiary alkaloids from roots of B. oblonga; 2'-N-methylberbamine is the first monoquaternary phenolic bisbenzylisoquinoline base. Seeds and pericarps of B. thunbergii DC. growing in this country were

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Two major bisbenzylisoquinoline alkaloids, isotetrandrine and berbamine and three protoberberine type alkaloids berberine, palmatine, and jatrorrhizine were isolated from seeds of Berberis thunbergii DC. Berberine and oxyberberine, which is not present in the seeds, were isolated from the pericarp. Identity of the isolated substances was verified by spectral means (i.r., u.V., and mass spectrometry), optical rotation, and comparison with specimens. Из семян растения Berberis thunbergii DC. выделены два главных алкалоида бйсбензилизохинолиновой группы изотетрандрин и бербамин. Из околоплоднико в выделен основной алкалоид третичной фракции оксиберберин, который отсутствует в семенах этого растения и берберин. Из четвертичных оснований выделены из семян берберин, пальматин и ятроррицин. Основания идентифицированы сравнением с истинными образцами и на основании спектральных данных и оптического вращения. Berberine, jatrorrhizine, and aporfine alkaloid magnoflorine were isolated from the underground and aerial parts of this plant together with tertiary bases oxyberberine, berbamine, oxyacanthine, and isotetrandrine [1,2]. The presence of alkaloids in fruits has not been tested so far. From the chemotaxonomic point of view it is important to ascertain the presence of secondary metabolites in the individual parts of the plant and therefore we studied their occurrence in fruits. Alkaloids berberine, berbamine, palmatine, oxyacanthine, jatrorrhizine, magnoflo­ rine, and columbamine are present in most species of the genus Berberis L. Six species, B. vulgaris, B. tschonoskyana , B. lamina, B. laurica, B. amurensis, B. baluchistanica, contain new isoquinoline alkaloids [3]. It has been found that roots and stems of B. oblonga and B. integerrima contain alkaloids in an approximately equal ratio, which is not the case with leaves [4, 5]. Oblongamine, a new type of monoquaternary oxyacanthine type [4] phenolic alkaloid and 2'-N-methylberbamine [5] were found in the portion of tertiary alkaloids from roots of B. oblonga; 2'-N-methylberbamine is the first monoquaternary phenolic bisbenzylisoquinoline base. Seeds and pericarps of B. thunbergii DC. growing in this country were

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Available abstract

Two major bisbenzylisoquinoline alkaloids, isotetrandrine and berbamine and three protoberberine type alkaloids berberine, palmatine, and jatrorrhizine were isolated from seeds of Berberis thunbergii DC. Berberine and oxyberberine, which is not present in the seeds, were isolated from the pericarp. Identity of the isolated substances was verified by spectral means (i.r., u.V., and mass spectrometry), optical rotation, and comparison with specimens. Из семян растения Berberis thunbergii DC. выделены два главных алкалоида бйсбензилизохинолиновой группы изотетрандрин и бербамин. Из околоплоднико в выделен основной алкалоид третичной фракции оксиберберин, который отсутствует в семенах этого растения и берберин. Из четвертичных оснований выделены из семян берберин, пальматин и ятроррицин. Основания идентифицированы сравнением с истинными образцами и на основании спектральных данных и оптического вращения. Berberine, jatrorrhizine, and aporfine alkaloid magnoflorine were isolated from the underground and aerial parts of this plant together with tertiary bases oxyberberine, berbamine, oxyacanthine, and isotetrandrine [1,2]. The presence of alkaloids in fruits has not been tested so far. From the chemotaxonomic point of view it is important to ascertain the presence of secondary metabolites in the individual parts of the plant and therefore we studied their occurrence in fruits. Alkaloids berberine, berbamine, palmatine, oxyacanthine, jatrorrhizine, magnoflo­ rine, and columbamine are present in most species of the genus Berberis L. Six species, B. vulgaris, B. tschonoskyana , B. lamina, B. laurica, B. amurensis, B. baluchistanica, contain new isoquinoline alkaloids [3]. It has been found that roots and stems of B. oblonga and B. integerrima contain alkaloids in an approximately equal ratio, which is not the case with leaves [4, 5]. Oblongamine, a new type of monoquaternary oxyacanthine type [4] phenolic alkaloid and 2'-N-methylberbamine [5] were found in the portion of tertiary alkaloids from roots of B. oblonga; 2'-N-methylberbamine is the first monoquaternary phenolic bisbenzylisoquinoline base. Seeds and pericarps of B. thunbergii DC. growing in this country were

Key concepts: Jatrorrhizine, Berberine, Berberis, Palmatine, Berberidaceae, Alkaloid, Isoquinoline, Chemistry

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Isolation and identification of alkaloids from fruits of Berberis thunbergii DC. — Research Paper | ScholarLens