Barakol, a novel dioxaphenalene derivative from Cassia siamea

Hassanali, Ahmed; King, Trevor J.; Wallwork, S. C.

doi:10.1039/c29690000678

Cited by 20 publications

(10 citation statements)

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“…10 cm), TLC-densitometry can be used to develop up to 24 chromatographic runs and therefore, several samples can be compared simultaneously as was done in this study. The R f value, UV, IR and 1 H-NMR spectral data, and melting point of the purified barakol were similar to those of the authentic sample and also previously reported values [15][16][17] . Compared to HPLC-ECD, which had been used to determine the purity of pure barakol [10] , TLC-dosimetric method is less expensive and therefore offers an alternative method for quantitative analysis of barakol content in S. siamea leaves and flowers.…”

Section: Discussionsupporting

confidence: 53%

Quantitative Analysis of Barakol Content in <i>Senna siamea</i> Leaves and Flowers by TLC-Densitometry

Padumanonda¹,

Suntornsuk²,

Gritsanapan³

2006

Med Princ Pract

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Objective: To develop a TLC-densitometric method for the determination of barakol content in Senna siamea leaf and flower extracts, and to compare the barakol content in mature leaves, young leaves and young flowers of the plant which are consumed as a vegetable in curry. Materials and Methods: The extraction of pure barakol was performed by boiling the fresh young leaves of S. siamea with 0.5% sulfuric acid followed by chloroform extraction. The extract was further purified and recrystallized from absolute ethanol. Authentic sample of barakol was used for the validation of the TLC-densitometric method. Chromatography was performed on a TLC aluminium plate precoated with silica gel 60 F₂₅₄as a stationary phase and chloroform-methanol (85:15 v/v) as a solvent system. Fifteen percent ethanolic extracts of mature leaves, young leaves and flowers of S. siamea were analyzed and compared for barakol content using the validated TLC-densitometric method. Both the validation and analysis of barakol by TLC-densitometry were carried out at the absorbance mode of 366 nm. Results: Barakol was extracted as pure lemon-yellow crystals from young S. siamea leaves with 0.1% yield. Linearity was found over the range of 200–900 ng/spot (r² = 0.997). The developed method gave high precision (%RSD < 0.50) and accuracy (average 101.12%). The limit of detection and limit of quantitation were 8 and 50 ng, respectively. Barakol content in young leaves, mature leaves and young flowers were 1.67, 0.78 and 1.43% dry weight, respectively. R_f value of the barakol in young leaves, young flowers and authentic sample was the same: 0.45 ± 0.03. Conclusion: The TLC-densitometric method was simple, precise and convenient; hence it is an effective procedure for the simultaneous determination of barakol in plant extracts.

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Section: Discussionsupporting

confidence: 53%

Quantitative Analysis of Barakol Content in <i>Senna siamea</i> Leaves and Flowers by TLC-Densitometry

Padumanonda¹,

Suntornsuk²,

Gritsanapan³

2006

Med Princ Pract

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“…All samples were stored at room temperature in well-closed vials, protected from the light by aluminum foil to avoid degradation. The physical and spectroscopic characteristics of barakol were evaluated and compared with an authentic sample [5] and literature values [4], [9], [10]. The purity of barakol was assessed by TLC and HPLC to be > 99 %.…”

Section: Isolation Of Standard Barakolmentioning

confidence: 99%

“…S. siamea was used as a folk medicine to treat insomnia, diabetes, hypertension, asthma, and constipation. Potential CNS activities of S. siamea were due to the presence of barakol, an anxiolytic agent extracted from the leaves and flowers [2], [3], [4], [5], [6]. As a result, a herbal product containing S. siamea leaves was approved for commercial availability in Thailand for the treatment of anxiety and insomnia [7].…”

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confidence: 99%

Stability of Barakol under Hydrolytic Stress Conditions and its Major Degradation Product

Chantong¹,

Wongtongtair²,

Nusuetrong³

et al. 2009

Planta Med

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The aim of the present study was to investigate the stability of barakol, an anxiolytic constituent extracted from leaves of Senna siamea (Lam.) Irwin & Barneby (syn. Cassia siamea Lam.), under the International Conference on Harmonisation suggested conditions using HPLC with photodiode array detection. Extensive degradation of barakol was found to occur under alkaline conditions through base-catalyzed hydrolysis. Mild degradation of barakol was observed under thermal and oxidative stress while it was stable under acidic conditions. The reaction rate constants (Kobs) of barakol degradation under alkaline conditions at pHs 12 and 13 were 3.0x10(-5) and 9.6x10(-3) min(-1), respectively. The activation energy according to the Arrhenius plot was calculated to be 26.9+/-3.3 kcal/mol at pH 13 and temperatures between 12 and 51 degrees C. The major degradation product of barakol under both alkaline and thermal stress conditions was characterized by LC-MS and NMR as cassiachromone.

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“…Barakol was first isolated by Hassanali-Walji et al (1969) and its chemical structure (3␣, 4-dihydro-3␣, 8-dihydroxy-2, 5-dimethyl-1, 4-dioxaphenalene or 2,5-dimethyl-3␣H-pyrano-[2,3,4-de]-1-benzopyran-3␣,8-diol) was identified by Bycroft et al (1970). In animal models, barakol produces hypotension (Suwan et al, 1992), suppresses serotonergic activity as shown by decreasing 5-hydroxytryptophan-induced head shake behavior (Tongroach et al, 1992) and possesses anxiolytic activity on the elevated plus maze, a behavioral test for anxiolytic drugs (Thongsaard et al, 1996).…”

Section: Introductionmentioning

confidence: 99%

Barakol suppresses norepinephrine-induced inhibition of spontaneous longitudinal smooth muscle contractions in isolated rat small intestine

Deachapunya

Thongsaard

Poonyachoti

2005

Journal of Ethnopharmacology

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Barakol, a novel dioxaphenalene derivative from Cassia siamea

Cited by 20 publications

References 0 publications

Quantitative Analysis of Barakol Content in <i>Senna siamea</i> Leaves and Flowers by TLC-Densitometry

Quantitative Analysis of Barakol Content in <i>Senna siamea</i> Leaves and Flowers by TLC-Densitometry

Stability of Barakol under Hydrolytic Stress Conditions and its Major Degradation Product

Barakol suppresses norepinephrine-induced inhibition of spontaneous longitudinal smooth muscle contractions in isolated rat small intestine

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