The influence of deoxyribonucleic acid on ultraviolet and visible light absoption of berberine

Klimek, M.; Hnilica, Lubomir S.

doi:10.1016/0003-9861(59)90179-1

Cited by 15 publications

(4 citation statements)

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“…Since it has been reported that berberine forms complexes with duplex, triplex, and quadruplex DNA (Klímek and Hnilica 1959; Yamagishi 1962; Kley and Hahn 1969; Lee et al 1993; Ren and Chaires 1999; Franceschin et al 2006), we attempted to treat as1 and as2 mutant plants with one of the DNA intercalators, N -methylmesoporphyrin IX (NMM), which has been known as a major quadruplex DNA ligand (Arthanari et al 1998). NMM treatment severely inhibited growth of plants at 10 μM and plants rarely germinated at 25 μM (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…It has been reported that Arabidopsis plants might not produce berberine (Facchini et al 2004); nevertheless, effects of berberine on A. thaliana have not been reported. For a half century, it has been known that berberine interacts with DNA and RNA (Klímek and Hnilica 1959; Yamagishi 1962; Kley and Hahn 1969; Wolfe et al 1972). Berberine is used in biochemical research as a fluorescent probe of DNA and RNA (Hirakawa et al 2005; Islam and Kumar 2008; Islam et al 2009).…”

Section: Introductionmentioning

confidence: 99%

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Berberine enhances defects in the establishment of leaf polarity in asymmetric leaves1 and asymmetric leaves2 of Arabidopsis thaliana

et al. 2012

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Leaves develop as flat lateral organs from the indeterminate shoot apical meristem. The establishment of polarity along three-dimensional axes, proximal–distal, medial–lateral, and adaxial–abaxial axes, is crucial for the growth of normal leaves. The mutations of ASYMMETRIC LEAVES1 (AS1) and AS2 of Arabidopsis thaliana cause defects in repression of the indeterminate state and the establishment of axis formation in leaves. Although many mutations have been identified that enhance the adaxial–abaxial polarity defects of as1 and as2 mutants, the roles of the causative genes in leaf development are still unknown. In this study, we found that wild-type plants treated with berberine produced pointed leaves, which are often observed in the single mutants that enhance phenotypes of as1 and as2 mutants. The berberine-treated as1 and as2 mutants formed abaxialized filamentous leaves. Berberine, an isoquinoline alkaloid compound naturally produced in various plant sources, has a growth inhibitory effect on plants that do not produce berberine. We further showed that transcript levels of meristem-specific class 1 KNOX homeobox genes and abaxial determinant genes were increased in berberine-treated as1 and as2. Berberine treated plants carrying double mutations of AS2 and the large subunit ribosomal protein gene RPL5B showed more severe defects in polarity than did the as2 single mutant plants. We suggest that berberine inhibits (a) factor(s) that might be required for leaf adaxial cell differentiation through a pathway independent of AS1 and AS2. Multiple pathways might play important roles in the formation of flat symmetric leaves.Electronic supplementary materialThe online version of this article (doi:10.1007/s11103-012-9929-7) contains supplementary material, which is available to authorized users.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Berberine enhances defects in the establishment of leaf polarity in asymmetric leaves1 and asymmetric leaves2 of Arabidopsis thaliana

et al. 2012

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“…A large number of studies [120][121][122][123][124][125][126][127][128][129][130][131][132] reported the complexation of berberine with DNA possibly by a mechanism of intercalation. The authors laboratory [125][126][127][128][129] have first demonstrated the base and sequence specificity of berberine from studies with several naturally occurring and synthetic DNAs of differing base composition and sequences.…”

Section: A L K a L O I D -B -D N A I N T E R A C T I O N A Berberimentioning

confidence: 99%

Molecular aspects on the interaction of protoberberine, benzophenanthridine, and aristolochia group of alkaloids with nucleic acid structures and biological perspectives

Maiti

Kumar

2006

Medicinal Research Reviews

164

103

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Alkaloids occupy an important position in chemistry and pharmacology. Among the various alkaloids, berberine and coralyne of the protoberberine group, sanguinarine of the benzophenanthridine group, and aristololactam-beta-d-glucoside of the aristolochia group have potential to form molecular complexes with nucleic acid structures and have attracted recent attention for their prospective clinical and pharmacological utility. This review highlights (i) the physicochemical properties of these alkaloids under various environmental conditions, (ii) the structure and functional aspects of various forms of deoxyribonucleic acid (DNA) (B-form, Z-form, H(L)-form, protonated form, and triple helical form) and ribonucleic acid (RNA) (A-form, protonated form, and triple helical form), and (iii) the interaction of these alkaloids with various polymorphic DNA and RNA structures reported by several research groups employing various analytical techniques like absorbance, fluorescence, circular dichroism, and NMR spectroscopy; electrospray ionization mass spectrometry, thermal melting, viscosity, and DNase footprinting as well as molecular modeling and thermodynamic studies to provide detailed binding mechanism at the molecular level for structure-activity relationship. Nucleic acids binding properties of these alkaloids are interpreted in relation to their biological activity.

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“…The alkaloids of the berberine group are known to form complexes with biologically important macromolecules, such as alcohol dehydrogenase from horse liver (3) and some nucleic acids (4). In the spectrophotometric study of these interactions it was first necessary to determine the absorption properties of the alkaloids.…”

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confidence: 99%

The ultraviolet and visible absorption spectra of berberrubine

Gašparec¹,

Komorsky‐Lovrić²,

Lovrić³

1982

Can. J. Chem.

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ZVONIMIR GASPAREC, SEBOJKA KOMORSKY-LOVRI~, and MILIVOJ LOVRIC. Can. J. Chem. 60, 970 (1982).The absorption spectra of berberrubine in the visible and uv spectral range were recorded. The measurements were made in four different solvents (water, absolute methanol, absolute ethanol, and absolute propanol) changing the acidity and the alkalinity of the solutions in the wide range from pH 2 to pH 13 by the addition of HC1 and KOH. The experimental and theoretical results, derived by simple Hiickel MO calculations, were compared and discussed.ZVONIMIR GASPAREC, SEBOJKA KOMORSKY-LOVRI~ et MILIVOJ LOVRIC. Can. J. Chem. 60, 970 (1982).On a enregistre les spectres d'absorbtion de la berberrubine dans le visible et l'uv. On a effectue ces mesures dans quatre solvants differents (eau, methanol, ethanol et propanol) et on a fait varier le pH de 2 a 13 par addition de HC1 ou de KOH aux solutions. On compare et on discute des resultats experimentaux et des valeurs theoriques obtenues par des calculs simples OM de Hiickel.[Traduit par le journal]Berberrubine belongs to the group of protoberberinic alkaloids (Fig. 1). It has been, so far, isolated only from Berberis vulgaris L . , family Berberidaceae (I), but as early as 1903 Berkurst and Frerichs (2) had synthesized it from berberine chloride by pyrolysis at 200°C with urea.The alkaloids of the berberine group are known to form complexes with biologically important macromolecules, such as alcohol dehydrogenase from horse liver (3) and some nucleic acids (4). In the spectrophotometric study of these interactions it was first necessary to determine the absorption properties of the alkaloids. Recently, Pavelka and co-workers have published several papers dealing with the ultraviolet and visible absorption (5,6) and fluorescence (7) spectra of protoberberinic alkaloids. The authors have paid much attention to berberrubine because of some of its special properties. Unfortunately, their measurements were done only in 96% ethanol solution at undefined pH.The aim of this work is to report the results of the measurements of the absorption spectra of berberrubine in four different solvents with pH of the solutions changing in the range between 2 and 13. Besides, some simple Hiickel MO calculations were performed for berberine and its derivatives jatrorhizine, berberrubine, and jatrorubine and the results will be compared with present and previously published (9,10) data. The calculations were made for all three possible ionic forms of these alkaloids (quaternary amine cation, carbinolic, and open amino-aldehydic forms) in order to gain a better understanding of the possible ionic transformation of berbermbine under the influence of acid or base.

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The influence of deoxyribonucleic acid on ultraviolet and visible light absoption of berberine

Cited by 15 publications

References 2 publications

Berberine enhances defects in the establishment of leaf polarity in asymmetric leaves1 and asymmetric leaves2 of Arabidopsis thaliana

Berberine enhances defects in the establishment of leaf polarity in asymmetric leaves1 and asymmetric leaves2 of Arabidopsis thaliana

Molecular aspects on the interaction of protoberberine, benzophenanthridine, and aristolochia group of alkaloids with nucleic acid structures and biological perspectives

The ultraviolet and visible absorption spectra of berberrubine

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