Brazilin from Caesalpinia sappan wood as an antiacne agent

Batubara, Irmanida; Mitsunaga, Tohru; Ohashi, Haruo

doi:10.1007/s10086-009-1046-0

Cited by 70 publications

(54 citation statements)

References 31 publications

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“…Based on these 1 H NMR and 13 C NMR results, CS-1 was identified as brazilin by comparing with the data reported previously (Batubara et al, 2010).…”

supporting

confidence: 70%

“…Brazilin itself showed a stronger anti-P. acnes activity than the CSE, with MIC and MBC values of 15.6 and 31.2 mg/mL, respectively. The anti-P. acnes activity of brazilin was also markedly stronger than that previously reported by Batubara et al (2010). This may be due to the different strains of P. acnes as well as purity of brazilin used in the assay.…”

Section: Resultsmentioning

confidence: 49%

“…This may be due to the different solvents used for the extraction as well as the quality of the plant raw materials. On the basis of the antibacterial assay-guided isolation, CS-1 that had been purified as the antibacterial constituent of C. sappan heartwood was identified as brazilin by 1 H NMR and 13 C NMR and compared with the data in the literature (Batubara et al, 2010). Brazilin itself showed a stronger anti-P. acnes activity than the CSE, with MIC and MBC values of 15.6 and 31.2 mg/mL, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…It has been reported that C. sappan wood extract also exhibited better antibacterial activity against P. acnes as compared with other 39 medicinal plants from Indonesia (Batubara et al, 2009). Brazilin has been reported to be the active compound against P. acnes (Batubara et al, 2010), but the MIC and MBC values (0.50 mg/mL) were too high to be the antibacterial active principle. We have therefore reinvestigated the antibacterial activity of the crude extract of C. sappan heartwood and purified the antibacterial constituent again using the antibacterial assay-guided isolation.…”

Section: Introductionmentioning

confidence: 97%

“…Brazilin [(6aS,11bR)-7,11b-dihydro-6H-indeno[2,1-c] chromene-3,6a,9,10-tetrol] (Figure 1) is a biologically active compound that has antibacterial, anti-inflammatory, and anti-oxidant activities and has been isolated from C. sappan heartwood (Bae et al, 2005;Batubara et al, 2010;Hu et al, 2009;Xu & Lee, 2004). However, the major limitation of the use of this pure naturally derived compound is its high cost of production, due to the many steps required and time involved for purification.…”

Section: Introductionmentioning

confidence: 99%

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Anti-Propionibacterium acnesassay-guided purification of brazilin and preparation of brazilin rich extract fromCaesalpinia sappanheartwood

Nirmal¹,

Panichayupakaranant

2014

Pharmaceutical Biology

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Context: Caesalpinia sappan L. (Leguminosae or Fabaceae) heartwood has been used as a coloring agent, with antibacterial activity in food, beverages, cosmetics, and garments. Objectives: To purify brazilin from C. sappan heartwood and use it as a standard marker for the preparation and standardization of an active constituent-rich extract. Material and methods: Crude ethanol extracts of C. sappan heartwood (CSE) were fractionated to isolate brazilin by an anti-P. acnes assay-guided isolation. Quantitative analysis was performed by HPLC. Minimum inhibitory concentrations (MICs) and minimum bactericidal concentrations (MBCs) were determined by the broth microdilution method. Results and discussion: Brazilin isolated from CSE possessed antibacterial activity against P. acnes with MIC and MBC values of 15.6 and 31.2 mg/mL, respectively. Brazilin was, therefore, used as a standard marker for standardization and preparation of a brazilin rich extract (BRE). BRE was prepared from CSE using a simple one-step purification using a macroporous resin column eluted with 35% v/v ethanol. This method increased the brazilin content in the BRE up to 39.9% w/w. The antibacterial activity of the standardized BRE against acne involved bacteria was higher than for the CSE but lower than brazilin. However, for industrial applications, a large-scale one-step preparation of BRE has more advantages than the use of pure brazilin in terms of convenience and a low-cost production process. Therefore, BRE is considered as a potential coloring agent with antibacterial activity which is used for pharmaceutical, cosmetic, and nutraceutical applications.

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“…Based on these 1 H NMR and 13 C NMR results, CS-1 was identified as brazilin by comparing with the data reported previously (Batubara et al, 2010).…”

supporting

confidence: 70%

Section: Resultsmentioning

confidence: 49%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

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Anti-Propionibacterium acnesassay-guided purification of brazilin and preparation of brazilin rich extract fromCaesalpinia sappanheartwood

Nirmal¹,

Panichayupakaranant

2014

Pharmaceutical Biology

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Sources, Application, and Analysis of Natural Colorants: An Indian Perspective

Samanta

Singhee

2023

Handbook of Natural Colorants

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Synthesis of Dihydro‐5H‐Benzo[c]‐Fluorenes, Dihydroindeno[c]‐Chromenes and Thiochromenes via Intramolecular Cyclization and their Effect on Human Leukemia Cells

et al. 2022

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In this work, we describe the construction of a series of 6,7-dihydro-5Hbenzo[c]fluorenes. Their synthesis is based on an intramolecular-cyclization of tricyclic substrates, which has an alcohol functional group in acidic conditions at ambient temperature. Certain reaction optimization conditions reveal that triflic acid was the most convenient reagent for this transformation, affording a broad range of fluorene derivatives in a 37 to 93% yield. We illustrate the robustness of this methodology through a gram-scale synthesis, and the preparation of dihydroindeno[c]-chromenes thiochromenes, and azulenes derivatives.

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Brazilin from Caesalpinia sappan wood as an antiacne agent

Cited by 70 publications

References 31 publications

Anti-Propionibacterium acnesassay-guided purification of brazilin and preparation of brazilin rich extract fromCaesalpinia sappanheartwood

Anti-Propionibacterium acnesassay-guided purification of brazilin and preparation of brazilin rich extract fromCaesalpinia sappanheartwood

Sources, Application, and Analysis of Natural Colorants: An Indian Perspective

Synthesis of Dihydro‐5H‐Benzo[c]‐Fluorenes, Dihydroindeno[c]‐Chromenes and Thiochromenes via Intramolecular Cyclization and their Effect on Human Leukemia Cells

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