Vibrational spectroscopic study of brazilin and brazilein, the main constituents of brazilwood from Brazil

Oliveira, Luiz Fernando Cappa de; Edwards, Howell G. M.; Velozo, Eudes da Silva; Nesbitt, Mark

doi:10.1016/s0924-2031(01)00138-2

Cited by 82 publications

(48 citation statements)

References 19 publications

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“…SERS spectrum of the pink colour from the Dourado Atlas (map 16), compared with brazilwood pigment lake and brazilein spectra; λ exc = 633 nm. system, at 1199 and 1165 cm −1 owing to ν(C-C) and δ(C-H), at 1108 cm −1 given by the in-plane δ(CH), and, finally, also at 468 cm −1 owing to ring deformation [51]. When comparing the SERS spectra of brazilein with the brazilwood lake paint reconstruction (from recipe 8 of the The book on how to make colours, where gypsum is used as a filler and gum arabic as a binder [15]) small differences were found mostly in the region between 1700 and 1100 cm −1 , possibly resulting from the presence of gypsum (table 3 and figure 4).…”

Section: Results and Discussion (A) Reference Samples (I) Orcein: Masmentioning

confidence: 98%

“…Microspectrofluorimetry showed an excitation maximum at 560 nm and emission maximum at 593-608 nm, which is in agreement with the brazilwood recipe 8 from Livro de Como se Fazem as Cores, which also contains gypsum (electronic supplementary material, figure S7) [5]. Raman spectroscopy showed a high fluorescence background signal and for this reason the identification of the dye was only achieved by SERS (following HF treatment), as presented in table 3 and figure 3, through its bands at 367, 417, 462, 485, 522 and 546 cm −1 owing to ring deformation, at 638, 671, 713, 724 and 808 cm −1 assigned to the out-of-plane δ(CH) and δ(CO), at 1105 cm −1 attributed to the in-plane δ(CH), at 1165 cm −1 owing to the δ(CCH) and ν(C-C), at 1201 cm −1 ascribed to δ(C-C), at 1350 cm −1 attributed to the ν(C-O) and, finally, at 1487 and 1556 cm −1 both assigned to ν(C=C) [50,51]. The SERS spectrum is in agreement with the spectra collected for the brazilein chromophore, but even more with the brazilwood reconstruction, which is also in agreement with the microspectrofluorimetry results.…”

Section: (C) Fernão Vaz Dourado Atlasmentioning

confidence: 99%

See 1 more Smart Citation

Organic dyes in illuminated manuscripts: a unique cultural and historic record

Melo

Nabais

Guimarães

et al. 2016

Phil. Trans. R. Soc. A.

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Section: Results and Discussion (A) Reference Samples (I) Orcein: Masmentioning

confidence: 98%

Section: (C) Fernão Vaz Dourado Atlasmentioning

confidence: 99%

Organic dyes in illuminated manuscripts: a unique cultural and historic record

Melo

Nabais

Guimarães

et al. 2016

Phil. Trans. R. Soc. A.

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“…It indicated isolate has a-OH (hydroxyl) functional group, very strong absorption at 1662,6 cm -1 showed the component has a carbonyl functional group (C=O). C=O group is an important infrared spectra characterization of brazilein that could be distinguished by brazilin, the other major compound of kayu secang [18]. The other absorption with strong and sharp absorption at 1604.8 cm -1 showed isolate has a C=C functional group from the aromatic ring.…”

Section: Characterization Of Brazileinmentioning

confidence: 99%

Cytotoxic Activity of Brazilein Isolated From Secang (Caesalpinia Sappan L.) Against McF7/Dox Cells by Inhibition of P-Glycoprotein

Laksmiani

Meiyanto

Susidarti

2017

Int J Pharm Pharm Sci

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Objective: This study was focused on isolation of brazilein from the dried heartwood of Secang (Caesalpinia sappan L.) followed by its characterization using Infrared (IR) spectroscopy, liquid chromatography-mass spectrometry (LC-MS) with electrospray ionization (ESI), proton ( 1 H), carbon-13 ( 13 Methods: Brazilein was isolated and purified from ethyl acetate fraction by flash silica gel column chromatography, eluting with chloroform, ethyl acetate and methanol in gradient concentration. In the cytotoxicity assay, MCF-7/DOX cells were cultured in the presence of brazilein for 24 hour (h) and cell viability was evaluated by using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay. Interactions between brazilein and the target proteins were evaluated and calculated in silico by molecular docking using PLANTS. C) nuclear magnetic resonance (NMR) and two dimensional (2D)-NMR, evaluation the cytotoxic activity of brazilein in MCF-7 resistant doxorubicin (MCF-7/DOX) cells and evaluate the interaction between brazilein and ATP with P-glycoprotein (Pgp) in silico using molecular docking. Results:The infrared, mass spectra with a molecular weight of 284 and NMR signal confirmed that was brazilein. MTT assay showed a dosedependent inhibition of MCF-7/DOX cell proliferation with brazilein IC50Conclusion: Brazilein has a potent cytotoxic value on MCF-7/DOX and high affinity in Pgp protein target. Brazilein can be developed as anticancer especially in cancer resistance incidence. Further study must be established to evaluate the molecular mechanism of brazilein inhibit MCF-7/DOX cell proliferation in vitro.value of 43 µM. The docking score of brazilein was-71,45 kcal/mol and ATP value-96,23 kcal/mol.

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“…Brazilein (6a,7-dihydro-3,6a,10-trihydroxy-benz [b]indeno [1,2-d]pyran-9(6H)-one) is a major component of Caesalpinia sappan L. organic extracts [1,2] . C. sappan is an indeciduous tree native to China and south India.…”

Section: Introductionmentioning

confidence: 99%

Study on Cardioactive Effects of Brazilein

Zhao¹,

Yang²,

Tao³

et al. 2006

Pharmacology

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Brazilein (6a,7-dihydro-3,6a,10-trihydroxy-benz[b]indeno[1,2-d]pyran-9(6H)-one) is a compound obtained in a large amount from Caesalpinia sappan ethanol extracts with a high purity of about 98%. In isolated cardiac tissues, we found that brazilein exhibited a positive inotropic action in a concentration-dependent manner with little effect on heart rate and coronary perfusion. To study its possible mode of action, isolated rat hearts were treated with propranolol. This treatment did not alter the cardiotonic effect of brazilein, suggesting that this effect does not involve stimulation of β-adrenoceptors. On the other hand, an analysis of the interaction between Na⁺,K⁺-ATPase and brazilein was carried out. Albino guinea pig erythrocytes (mainly α1-Na⁺,K⁺-ATPase isoforms) enriched with Na⁺,K⁺-ATPase isoforms were utilized to compare the inhibition promoted by brazilein with that of classical inhibitors such as the cardiac glycoside deslanoside. Analysis of inhibition curves revealed that unlike deslanoside, brazilein had a relatively low affinity for erythrocyte isoforms and failed to completely inhibit the Na⁺,K⁺-ATPase activity. The extent of the maximum inhibition rate was about 50%. The inhibitory effect of brazilein was not antagonized by 10 mmol/l K⁺, as observed with deslanoside. Electrocardiogram research in vivo showed that brazilein did not induce the ventricular arrhythmias observed with deslanoside, suggesting that brazilein might have a less adverse effect and higher therapeutic index than cardiac glycosides. In light of all the above-mentioned observations, it can be concluded that brazilein, a molecule with a non-steroidal skeleton, produced its positive inotropic effect through inhibiting Na⁺,K⁺-ATPase and could thus serve as a structural paradigm to develop new inotropic drugs.

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Vibrational spectroscopic study of brazilin and brazilein, the main constituents of brazilwood from Brazil

Cited by 82 publications

References 19 publications

Organic dyes in illuminated manuscripts: a unique cultural and historic record

Organic dyes in illuminated manuscripts: a unique cultural and historic record

Cytotoxic Activity of Brazilein Isolated From Secang (Caesalpinia Sappan L.) Against McF7/Dox Cells by Inhibition of P-Glycoprotein

Study on Cardioactive Effects of Brazilein

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