The isolation of bioactive flavonoids from Jacaranda obtusifolia H. B. K. ssp. rhombifolia (G. F. W. Meijer) Gentry

Khamsan, Sorachai; Liawruangrath, Saisunee; Teerawutkulrag, Aphiwat; Pyne, Stephen G.; Garson, Mary J.; Liawruangrath, Boonsom

doi:10.2478/v10007-012-0014-1

Cited by 22 publications

(20 citation statements)

References 12 publications

(9 reference statements)

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“…Both of them are found in numerous edible plant species primarily belonging to the Fabaceae 1–3 or Amaryllidaceae families, 4 but are also found in the Asparagaceae 5 and Bignonaceae 6 families. Despite their wide distribution, these two polyphenols have been mainly studied as bio-active constituents of Glycyrrhiza species (licorice, Fabaceae).…”

Section: Introductionmentioning

confidence: 99%

Dynamic Residual Complexity of the Isoliquiritigenin–Liquiritigenin Interconversion During Bioassay

Simmler

Hajirahimkhan

Lankin

et al. 2013

J. Agric. Food Chem.

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Bioactive components in food plants can undergo dynamic processes that involve multiple chemical species. For example, 2′-hydroxychalcones can readily isomerize into flavanones. Although chemically well documented, this reaction has barely been explored in the context of cell-based assays. The present time-resolved study fills this gap by investigating the isomerization of isoliquiritigenin (a 2′-hydroxychalcone) and liquiritigenin (a flavanone) in two culture media (DMEM and RPMI) with and without MCF-7 cells, using HPLC-DAD-ESI/APCI-MS for analysis. Both compounds isomerized and epimerized under all investigated biological conditions, leading to mixtures of isoliquiritigenin and R/S-liquiritigenin, with 19.6% R enantiomeric excess. Consequently, all three species can potentially modulate the biological responses. This exemplifies dynamic residual complexity and demonstrates how both non-chiral reactions and enantiomeric discrimination can occur in bioassay media, with or without cells. The findings highlight the importance of controlling in situ chemical reactivity, influenced by biological systems when evaluating the mode of action of bioactives.

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Section: Introductionmentioning

confidence: 99%

Dynamic Residual Complexity of the Isoliquiritigenin–Liquiritigenin Interconversion During Bioassay

Simmler

Hajirahimkhan

Lankin

et al. 2013

J. Agric. Food Chem.

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“…The compounds possessed a low cytotoxicity activity toward L-6 cells, with the exception of Jacaglabroside A which was substantially more cytotoxic (IC 50 was 8.3, >90, 87 and 85 μg/mL for Jacaglabrosides A-D respectively) [28] . [29] .…”

Section: Anticancer Activitymentioning

confidence: 99%

“…Rhombifolia (G. F. W. Meijer) Gentry. The structures were elucidated based on 1 H, 13 C-NMR, comprehensive 2D-NMR, MS analyses and comparison with previously reported spectral data [29] .…”

Section: Phenolicsmentioning

confidence: 99%

“…Molecular structure (-)-Liquiritigenin [29] (-)-Neoliquiritin [29] O O RO OH R = H R = glucosyl Isoliquiritigenin [29] Isoliquiritin [29] OH O HO OR R = H R = glucosyl Formononetin [29] O O HO OCH 3…”

Section: Compound / Referencementioning

confidence: 99%

“…Young leaves and internal bark Jacaranda copaia [35,36] Antimicrobial (n)Antileishmanial (n)Antitrypanosomal Bark Leaves Jacaranda cuspidifolia [18,19] Moderate antifungal Stem bark Jacaranda filicifolia [37] (n)antimicrobial activity (-)Plasmodium falciparum Jacaranda glabra [28,38] (-)DPPH (-)ABTS Antioxidant Antimicrobial Hypothermic Cardiovascular depressive Hypotensive (-)α-adrenergic receptors Leaves Jacaranda mimosaefolia [25,31,39] Anticancer Potent anticancer Jacaranda obtusifolia [29] Antibacterial Bacteriostatic and bactericidal against S. aureus Antileishmanial Leaves Jacaranda puberula [27,30] (-), decrease, inhibit, reduce, down-regulate. (+), increase, activate, up-regulate.…”

Section: Weak Antiproteases Young Leavesmentioning

confidence: 99%

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The Genus Jacaranda (Bignoniaceae): An Updated Review

Mostafa¹,

Eldahshan²,

Singab³

2014

Phcog Commn.

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Genus Jacaranda has been traditionally used in treating skin disorders, venereal diseases, leishmaniasis, colds and rheumatism. Additionally, some species have shown diuretic and astringent properties. Objective: This review highlights and updates the traditional uses, pharmacology and phytochemistry of the genus Jacaranda. Materials and Methods: Information was obtained from Google Scholar, Scirus, PubMed and ScienceDirect. Results: Phytochemical studies on Jacaranda species have shown the presence flavonoids, phenylpropanoids, phenylethanoids, sterols and triterpenes. Extracts of different Jacaranda species possess a wide range of pharmacological activities, such as antioxidant antidepressant, antimicrobial, anticancer, anti-leishmanial, antiprotozoal, hypotensive and anti-hypertriglyceridemic activities. Conclusion: The genus Jacaranda is a natural source of antioxidants and has been widely used in traditional Ethnobotany. Thus, it could be exploited as a potential source for plant-based pharmaceutical products. The present review could form a sound basis for further investigation in the potential discovery of new natural bioactive compounds and could provide preliminary information for future research.

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Preparative isolation and analysis of alcohol dehydrogenase inhibitors from Glycyrrhiza uralensis root using ultrafiltration combined with high‐performance liquid chromatography and high‐speed countercurrent chromatography

Chen

Liu

Chen

2014

J of Separation Science

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A simple, rapid, and effective assay based on ultrafiltration combined with high-performance liquid chromatography and high-speed countercurrent chromatography was developed for screening and purifying alcohol dehydrogenase inhibitors from Glycyrrhiza uralensis root extract. Experiments were carried out to optimize binding conditions including alcohol dehydrogenase concentration, incubation time, temperature, and pH. By comparing the chromatograms, three compounds were found possessing alcohol dehydrogenase binding activity in Glycyrrhiza uralensis root. Under the target-guidance of ultrafiltration combined with the high-performance liquid chromatography experiment, liquiritin (1), isoliquiritin (2), and liquiritigenin (3) were separated by high-speed countercurrent chromatography using ethyl acetate/methanol/water (5:1:4) as the solvent system. The alcohol dehydrogenase inhibitory activities of these three isolated compounds were assessed; compound 2 showed strongest inhibitory activity with an IC50 of 8.95 μM. The results of the present study indicated that the combinative method using ultrafiltration, high-performance liquid chromatography and high-speed countercurrent chromatography could be widely applied for the rapid screening and isolation of enzyme inhibitors from complex mixtures.

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The isolation of bioactive flavonoids from Jacaranda obtusifolia H. B. K. ssp. rhombifolia (G. F. W. Meijer) Gentry

Cited by 22 publications

References 12 publications

Dynamic Residual Complexity of the Isoliquiritigenin–Liquiritigenin Interconversion During Bioassay

Dynamic Residual Complexity of the Isoliquiritigenin–Liquiritigenin Interconversion During Bioassay

The Genus Jacaranda (Bignoniaceae): An Updated Review

Preparative isolation and analysis of alcohol dehydrogenase inhibitors from Glycyrrhiza uralensis root using ultrafiltration combined with high‐performance liquid chromatography and high‐speed countercurrent chromatography

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