Literature DB >> 25859589

Species-specific Standardisation of Licorice by Metabolomic Profiling of Flavanones and Chalcones.

Charlotte Simmler, Tristesse Jones, Jeffrey R Anderson, Dejan C Nikolić, Richard B van Breemen, Djaja D Soejarto, Shao-Nong Chen, Guido F Pauli.   

Abstract

INTRODUCTION: Major phenolics from licorice roots (Glycyrrhiza sp.) are glycosides of the flavanone liquiritigenin (F) and its 2′-hydroxychalcone isomer, isoliquiritigenin (C). As the F and C contents fluctuate between batches of licorice, both quality control and standardisation of its preparations become complex tasks.
OBJECTIVE: To characterise the F and C metabolome in extracts from Glycyrrhiza glabra L. and Glycyrrhiza uralensis Fisch. ex DC. by addressing their composition in major F–C pairs and defining the total F:C proportion.
MATERIAL AND METHODS: Three types of extracts from DNA-authenticated samples were analysed by a validated UHPLC/UV method to quantify major F and C glycosides. Each extract was characterised by the identity of major F–C pairs and the proportion of Fs among all quantified Fs:Cs.
RESULTS: The F and C compositions and proportions were found to be constant for all extracts from a Glycyrrhiza species. All G. uralensis extracts contained up to 2.5 more Fs than G. glabra extracts. Major F–C pairs were B-ring glycosidated in G. uralensis, and A-/B-ring apiosyl-glucosidated in the G. glabra extracts. The F:C proportion was found to be linked to the glycosidation site: the more B-ring F-C glycosides were present, the higher was the final F:C proportion in the extract. These results enable the chemical differentiation of extracts from G. uralensis and G. glabra, which are characterised by total F:C proportions of 8.37:1.63 and 7.18:2.82, respectively.
CONCLUSION: Extracts from G. glabra and G. uralensis can be differentiated by their respective F and C compositions and proportions, which are both useful for further standardisation of licorice botanicals.
Copyright © 2013 John Wiley & Sons, Ltd.

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Year:  2013        PMID: 25859589      PMCID: PMC4391967          DOI: 10.1002/pca.2472

Source DB:  PubMed          Journal:  Phytochem Anal        ISSN: 0958-0344            Impact factor:   3.373


  25 in total

1.  Metabolic profiling of roots of liquorice (Glycyrrhiza glabra) from different geographical areas by ESI/MS/MS and determination of major metabolites by LC-ESI/MS and LC-ESI/MS/MS.

Authors:  Paola Montoro; Mariateresa Maldini; Mariateresa Russo; Santo Postorino; Sonia Piacente; Cosimo Pizza
Journal:  J Pharm Biomed Anal       Date:  2010-10-14       Impact factor: 3.935

2.  A comprehensive approach to identifying and authenticating botanical products.

Authors:  T J Smillie; I A Khan
Journal:  Clin Pharmacol Ther       Date:  2009-12-23       Impact factor: 6.875

3.  Simultaneous determination of five flavonoids in licorice using pressurized liquid extraction and capillary electrochromatography coupled with peak suppression diode array detection.

Authors:  X J Chen; J Zhao; Q Meng; S P Li; Y T Wang
Journal:  J Chromatogr A       Date:  2009-08-18       Impact factor: 4.759

4.  Analgesic and uterine relaxant effects of isoliquiritigenin, a flavone from Glycyrrhiza glabra.

Authors:  Yulu Shi; Debin Wu; Zhen Sun; Jing Yang; Hongyan Chai; Li Tang; Yue Guo
Journal:  Phytother Res       Date:  2012-03-03       Impact factor: 5.878

5.  Variation of glycyrrhizin and liquiritin contents within a population of 5-year-old licorice (Glycyrrhiza uralensis) plants cultivated under the same conditions.

Authors:  Mareshige Kojoma; Shigeki Hayashi; Toshiro Shibata; Yutaka Yamamoto; Haruo Sekizaki
Journal:  Biol Pharm Bull       Date:  2011       Impact factor: 2.233

6.  Interconverting flavanone glucosides and other phenolic compounds in Lippia salviaefolia Cham. ethanol extracts.

Authors:  Cristiano Soleo Funari; Thais Gaban Passalacqua; Daniel Rinaldo; Assunta Napolitano; Michela Festa; Anna Capasso; Sonia Piacente; Cosimo Pizza; Maria Claudia Marx Young; Giselda Durigan; Dulce Helena Siqueira Silva
Journal:  Phytochemistry       Date:  2011-08-24       Impact factor: 4.072

Review 7.  Quantitative 1H NMR. Development and potential of an analytical method: an update.

Authors:  Guido F Pauli; Tanja Gödecke; Birgit U Jaki; David C Lankin
Journal:  J Nat Prod       Date:  2012-04-06       Impact factor: 4.050

8.  Species identification of licorice using nrDNA and cpDNA genetic markers.

Authors:  Kenji Kondo; Mao Shiba; Hiroki Yamaji; Takashi Morota; Cheng Zhengmin; Pan Huixia; Yukihiro Shoyama
Journal:  Biol Pharm Bull       Date:  2007-08       Impact factor: 2.233

9.  Racemization at C-2 of naringin in pummelo (Citrus grandis) with increasing maturity determined by chiral high-performance liquid chromatography.

Authors:  Salvatore Caccamese; Rosa Chillemi
Journal:  J Chromatogr A       Date:  2009-11-03       Impact factor: 4.759

Review 10.  Review of pharmacological effects of Glycyrrhiza sp. and its bioactive compounds.

Authors:  Marjan Nassiri Asl; Hossein Hosseinzadeh
Journal:  Phytother Res       Date:  2008-06       Impact factor: 5.878

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  11 in total

1.  Cytochrome P450 inhibition by three licorice species and fourteen licorice constituents.

Authors:  Guannan Li; Charlotte Simmler; Luying Chen; Dejan Nikolic; Shao-Nong Chen; Guido F Pauli; Richard B van Breemen
Journal:  Eur J Pharm Sci       Date:  2017-07-31       Impact factor: 4.384

2.  Classification of Flavonoid Metabolomes via Data Mining and Quantification of Hydroxyl NMR Signals.

Authors:  Yang Yu; Guido F Pauli; Lingyi Huang; Li-She Gan; Richard B van Breemen; Dianpeng Li; James B McAlpine; David C Lankin; Shao-Nong Chen
Journal:  Anal Chem       Date:  2020-03-26       Impact factor: 6.986

3.  Differential Effects of Glycyrrhiza Species on Genotoxic Estrogen Metabolism: Licochalcone A Downregulates P450 1B1, whereas Isoliquiritigenin Stimulates It.

Authors:  Tareisha L Dunlap; Shuai Wang; Charlotte Simmler; Shao-Nong Chen; Guido F Pauli; Birgit M Dietz; Judy L Bolton
Journal:  Chem Res Toxicol       Date:  2015-07-16       Impact factor: 3.739

4.  Identification and Chemical Standardization of Licorice Raw Materials and Dietary Supplements Using UHPLC-MS/MS.

Authors:  Guannan Li; Dejan Nikolic; Richard B van Breemen
Journal:  J Agric Food Chem       Date:  2016-10-14       Impact factor: 5.279

5.  Evidence for Chemopreventive and Resilience Activity of Licorice: Glycyrrhiza Glabra and G. Inflata Extracts Modulate Estrogen Metabolism in ACI Rats.

Authors:  Shuai Wang; Tareisha L Dunlap; Lingyi Huang; Yang Liu; Charlotte Simmler; Daniel D Lantvit; Jenna Crosby; Caitlin E Howell; Huali Dong; Shao-Nong Chen; Guido F Pauli; Richard B van Breemen; Birgit M Dietz; Judy L Bolton
Journal:  Cancer Prev Res (Phila)       Date:  2018-10-04

6.  In vitro production and distribution of flavonoids in Glycyrrhiza uralensis Fisch.

Authors:  Yan Zhou; Yanhong Jiao; Yahong Sun; Shumin Gao
Journal:  J Food Sci Technol       Date:  2019-12-05       Impact factor: 2.701

7.  Metabolite Profiling and Classification of DNA-Authenticated Licorice Botanicals.

Authors:  Charlotte Simmler; Jeffrey R Anderson; Laura Gauthier; David C Lankin; James B McAlpine; Shao-Nong Chen; Guido F Pauli
Journal:  J Nat Prod       Date:  2015-08-05       Impact factor: 4.050

8.  Induction of NAD(P)H:Quinone Oxidoreductase 1 (NQO1) by Glycyrrhiza Species Used for Women's Health: Differential Effects of the Michael Acceptors Isoliquiritigenin and Licochalcone A.

Authors:  Atieh Hajirahimkhan; Charlotte Simmler; Huali Dong; Daniel D Lantvit; Guannan Li; Shao-Nong Chen; Dejan Nikolić; Guido F Pauli; Richard B van Breemen; Birgit M Dietz; Judy L Bolton
Journal:  Chem Res Toxicol       Date:  2015-11-05       Impact factor: 3.739

9.  Improving natural product research translation: From source to clinical trial.

Authors:  Barbara C Sorkin; Adam J Kuszak; Gregory Bloss; Naomi K Fukagawa; Freddie Ann Hoffman; Mahtab Jafari; Bruce Barrett; Paula N Brown; Frederic D Bushman; Steven J Casper; Floyd H Chilton; Christopher S Coffey; Mario G Ferruzzi; D Craig Hopp; Mairead Kiely; Daniel Lakens; John B MacMillan; David O Meltzer; Marco Pahor; Jeffrey Paul; Kathleen Pritchett-Corning; Sara K Quinney; Barbara Rehermann; Kenneth D R Setchell; Nisha S Sipes; Jacqueline M Stephens; D Lansing Taylor; Hervé Tiriac; Michael A Walters; Dan Xi; Giovanna Zappalá; Guido F Pauli
Journal:  FASEB J       Date:  2019-12-10       Impact factor: 5.834

10.  Antiatherosclerotic effects of licorice extract supplementation on hypercholesterolemic patients: decreased CIMT, reduced plasma lipid levels, and decreased blood pressure.

Authors:  Yacov Fogelman; Diana Gaitini; Eli Carmeli
Journal:  Food Nutr Res       Date:  2016-04-22       Impact factor: 3.894

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