Total assignments of 1H and 13C NMR spectra of biflorin and bis‐biflorin from Capraria biflora

Fonseca, Aluísio Marques da; Pessoa, Otília Deusdênia Loiola; Silveira, Edilberto R.; Monte, Francisco José Queiroz; Braz‐Filho, Raimundo; Lemos, Telma L. G.

doi:10.1002/mrc.1295

Cited by 22 publications

(9 citation statements)

References 7 publications

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“…UV-Vis, IR and NMR analysis results confirmed the biflorin structure and matched the corresponding literature data [14,16]. Typical bands were observed at λ max 340 and 555 nm in the UV-Vis analysis.…”

Section: Resultssupporting

confidence: 87%

“…After this, the purified crystals of biflorin were collected and dried. The biflorin was characterized by the conventional spectroscopic methods UV-Vis (UV-1800, Shimadzu, Kyoto, Japan), infrared spectroscopy (IFS 66, Bruker, Billerica, MA, USA) and 1 H- and 13 C-NMR (Varian Unity plus 300 MHz, Garden State Scientific, Somerville, NJ, USA), and the data were compared with the literature [14,16].…”

Section: Methodsmentioning

confidence: 99%

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Biological Activity and Photostability of Biflorin Micellar Nanostructures

et al. 2015

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Capraria biflora L. is a shrub from the Scrophulariaceae family which produces in its roots a compound named biflorin, an o-naphthoquinone that shows activity against Gram-positive bacteria and fungi and also presents antitumor and antimetastatic activities. However, biflorin is hydrophobic and photosensitive. These properties make its application difficult. In this work we prepared biflorin micellar nanostructures looking for a more effective vehiculation and better preservation of the biological activity. Biflorin was obtained, purified and characterized by UV-Vis, infrared (IR) and species. In conclusion, the results showed that the micellar nanostructures could ensure the maintenance of the biological activity of biflorin, conferring photoprotection. Moreover, biflorin vehiculation in aqueous media was improved, favoring its applicability in biological systems.

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Section: Resultssupporting

confidence: 87%

Section: Methodsmentioning

confidence: 99%

Biological Activity and Photostability of Biflorin Micellar Nanostructures

et al. 2015

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“…The purity and structure ( Fig. 1a) were confirmed by spectroscopic analysis, including one-dimensional and two-dimensional nuclear magnetic resonance spectral data, infrared, physical properties, and comparison with data from the literature [12].…”

Section: Introductionmentioning

confidence: 98%

The in-vitro and in-vivo inhibitory activity of biflorin in melanoma

et al. 2011

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Biflorin, an ortho-naphthoquinone, is an active compound found in the roots of Capraria biflora L. It has been reported that biflorin presents anticancer activity, inhibiting both tumor cell line growth in culture and tumor development in mice. The aim of this study was to examine the effectiveness of biflorin treatment using both in-vitro and in-vivo melanoma models. Biflorin displayed considerable cytotoxicity against all tested cell lines, with half maximal inhibitory concentration values ranging from 0.58 μg/ml in NCI H23 (human lung adenocarcinoma) to 14.61 μg/ml in MDA-MB-231 (human breast cancer) cell lines. In a second set of experiments using B16 melanoma cells as a model, biflorin reduced cell viability but did not cause significant increase in the number of nonviable cells. In addition, the DNA synthesis was significantly inhibited. Flow cytometry analysis showed that biflorin may lead to an apoptotic death in melanoma cells, inducing DNA fragmentation and mitochondria depolarization, without affecting membrane integrity. In B16 melanoma-bearing mice, administration of biflorin (25mg/day) for 10 days inhibited tumor growth, and also increased the mean survival rate from 33.3±0.9 days (control) to 44.5±3.4 days (treated). Our findings suggest that biflorin may be considered as a promising lead compound for designing new drugs to be used in the treatment of melanoma.

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“…[6][7][8] Estudos farmacológicos realizados também demonstraram potencial citotóxico, analgésico, anti--inflamatório e antibiótico. 8 Estudos fitoquímicos realizados com um espécime desta espécie relataram a presença de diversas classes de substâncias, destacando-se as naftoquinonas biflorina e seu dímero bis-biflorina, 2,9 os sesquiterpenos caprariolídeos A-D 10 e os iridoides harpagida e 8-O-benzoilarpagida. 3,5 Dando continuidade ao estudo de plantas medicinais do Nordeste brasileiro, este trabalho relata os resultados obtidos de uma reinvestigação fitoquímica das raízes e do caule, incluindo-se a extração do óleo essencial das folhas, que foi testado como agente larvicida sobre Aedes aegypti.…”

Section: Introductionunclassified