Chiral separation of glycyrrhetinic acid by highperformance liquid chromatography

Ha, Yvette; Cheung, Andrew P.; Lim, Peter

doi:10.1016/0731-7085(91)80005-t

Cited by 12 publications

(10 citation statements)

References 16 publications

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“…Like glycyrrhizin, glycyrrhetinic acid can exist as two stereoisomers, the trans form 18α-glycyrrhetinic acid (AGA) and the cis form 18β-glycyrrhetinic acid (BGA) (18,19). Major structural differences between 18α-and 18β-glycyrrhetinic acids lie in the spatial orientation of hydrogen atom of C18, in BGA hydrogen atom of C18 and the carboxyl of C30 are in the same plane while in AGA, they are not in same plane (20).…”

Section: Introductionmentioning

confidence: 99%

18α-glycyrrhetinic acid targets prostate cancer cells by down-regulating inflammation-related genes

Munirathinam

2011

Int J Oncol

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Abstract. Glycyrrhetinic acid is an active triterpenoid metabolite of glycyrrhizin abundantly present in licorice roots. Glycyrrhetinic acid exists as α and β stereo-isomeric forms. Both stereo-isomeric forms are known to have anti-inflammatory and anticancer activity. However, the effects and anticancer mechanism of α glycyrrhetinic acid in prostate cancer cells has not yet been evaluated. Therefore, we investigated the growth inhibition, induction of apoptosis and the anticancer mechanisms of 18α-glycyrrhetinic acid (AGA), on the androgen-independent metastatic prostate cancer cell line DU-145. Our results showed that AGA inhibited proliferation and growth of these cells by inducing apoptosis as determined by Annexin V and flow cytometry analyses. Our studies also showed that HUVEC tube formation was drastically reduced when cultured in conditioned medium of AGA-treated DU-145 cells. In addition, AGA treatment prevented the invasion of DU-145 prostate cancer cells on matrigel coated transwells via down-regulation of NF-κB (p65), VEGF and MMP-9 expression. Furthermore, AGA treatment also downregulated the expression of pro-inflammatory cytokine/growth factor genes HMGB1, IL-6 and IL-8 in DU-145 cells. Interestingly, AGA simultaneously upregulated the expression of non-steroidal anti-inflammatory gene-1 (NAG-1) in DU-145 cells suggesting its anti-inflammatory activity on prostate cancer cells. Taken together, the results of this study suggest that AGA may be a promising anticancer agent that merits further investigation for the chemoprevention and treatment of prostate cancer.

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Section: Introductionmentioning

confidence: 99%

18α-glycyrrhetinic acid targets prostate cancer cells by down-regulating inflammation-related genes

Munirathinam

2011

Int J Oncol

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“…Few published papers have been found reporting the separation of the two isomers by HPLC (Tsai et al, 1991;Ha et al, 1991). A C 18 column was used for the separation by Tsai, while a chiral column gave a satisfactory resolution for the isomers in Ha et al 's papers.…”

Section: Conditions Of Chromatographymentioning

confidence: 97%

“…The commonly used HPLC with UV detection methods for the determination of GA in human plasma and experimental animals have been published many times (Zhang et al, 1989;Takeda et al, 1990;Ha et al, 1991;Yamamura et al, 1991;Tsai et al, 1992;Abe et al, 1994;Krahenbuhl et al, 1994b;Takeda et al, 1996;Gunnarsdottir and Johannesson, 1997;Gao et al, 2004), but they were not sensitive enough for pharmacokinetic research of GA since the terminal phase concentrations of GA for most volunteers were below their low limit of quantitation (LOQ). The micellar electrokinetic chromatography has also been reported (Wang et al, 1998); it was a tentative experiment and was not practical for large batches of biological samples.…”

Section: Introductionmentioning

confidence: 99%

“…The LC-MS and LC-MS/MS methods were much more sensitive and practical for the pharmacokinetic studies of GA, but all of them either dealt with a mixture of the two isomers or the high content β-GA; under the conditions of their experiments, α-GA and β-GA could not be separated. There have been rare papers regarding the HPLC separation of the 18α and 18β diastereomers of GA; Ha et al (1991) obtained separation with a chiral column and used the method in an optical purity assessment of GA isomers. This needs further investigation for bio-samples.…”

Section: Introductionmentioning

confidence: 99%

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Simultaneous determination of 18α‐ and 18β‐glycyrrhetic acid in human plasma by LC‐ESI‐MS and its application to pharmacokinetics

Zou

Wei

et al. 2008

Biomedical Chromatography

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A highly sensitive and selective LC-ESI-MS was developed, validated for the simultaneous determination of 18alpha-glycyrrhetic acid (alpha-GA) and 18beta-glycyrrhetic acid (beta-GA) for pharmacokinetic studies in healthy subjects. Sample preparation was performed by liquid-liquid extraction with ethyl acetate and the separations were achieved using a C(18) column with the mobile phase composed of 10 mmol/L ammonium acetate solution-methanol-acetonitrile (40:36:24, v/v/v) at a flow rate of 1 mL/min. The internal standard was honokiol and the epimers were quantified using a single quadrupole mass spectrometer employing ESI in the negative ion mode. The separation factor, alpha, was 1.512 for alpha- and beta-GA. The standard curves were linear for both epimers with coefficients of determination (r >or= 0.9998) over the concentration range of 1-150 ng/mL. The precision and accuracy were

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“…another active compound present in the licorice which exists as a trans-isomer (Zeng et al, 2006;Ha et al, 1991).…”

Section: Article Infomentioning

confidence: 99%

18α-Glycyrrhetinic acid inhibits the viability of HR5-CL11 cervical carcinoma cells through induction of apoptosis and DNA damage

Zhuang

Hu²,

Hong

et al. 2016

Bangladesh J Pharmacol

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The present study was aimed to investigate the effect of 18α-glycyrrhetinic acid on induction of apoptosis and DNA-damage in HR5-CL11 cervical carcinoma cells. The results revealed 73.6% reduction in HR5-CL11 cell viability on treatment with 5 µM concentration of 18α-glycyrrhetinic acid for 48 hours. The DNA of 18α-glycyrrhetinic acid-treated cells showed a ladder-like pattern. Fragmentation of DNA in the 18α-glycyrrhetinic acid-treated cells was markedly higher compared to the control cells. Examination of the DNA damage in HR5-CL11 cells after treatment with 18α-glycyrrhetinic acid showed breakage in DNA strands and formation of comet-like structures. The frequency of comet formation in 18α-glycyrrhetinic acid treated cells was found to be 7.8 after 48 hours. The population of cells with more than four γH2AX foci was increased to 38.6% on treatment with 5 µM concentration of 18α-glycyrrhetinic acid. Thus, 18α-glycyrrhetinic acid inhibits the viability of HR5-CL11 cervical cancer cells through induction of apoptosis by DNA damage and can be used for the treatment of cervical cancer.Video Clip:<a href="https://www.youtube.com/v/XZQHm07d2sk">MTT assay</a>: 1 min 13 sec

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Chiral separation of glycyrrhetinic acid by highperformance liquid chromatography

Cited by 12 publications

References 16 publications

18α-glycyrrhetinic acid targets prostate cancer cells by down-regulating inflammation-related genes

18α-glycyrrhetinic acid targets prostate cancer cells by down-regulating inflammation-related genes

Simultaneous determination of 18α‐ and 18β‐glycyrrhetic acid in human plasma by LC‐ESI‐MS and its application to pharmacokinetics

18α-Glycyrrhetinic acid inhibits the viability of HR5-CL11 cervical carcinoma cells through induction of apoptosis and DNA damage

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