Saponins from European Licorice Roots (Glycyrrhiza glabra)

Christian Schmid; Corinna Dawid; Verena Peters; Thomas Hofmann

doi:10.1021/acs.jnatprod.8b00022

Saponins from European Licorice Roots (Glycyrrhiza glabra)

Christian Schmid
, Corinna Dawid
, Verena Peters
, Thomas Hofmann^*

^*Corresponding author for this work

Technical University of Munich
Chair of Food Chemistry and Molecular Sensory Science

Research output: Contribution to journal › Article › peer-review

80 Scopus citations

Abstract

European licorice roots (Glycyrrhiza glabra), used in the food and beverage industry due to their distinctive sweet and typical licorice flavor, were fractionated, with the triterpenoid saponins isolated and their chemical structures determined by means of ESIMS, ESIMS/MS, HRESIMS, and 1D/2D NMR experiments. Next to the quantitatively predominant saponin glycyrrhizin (11) and some previously known saponins, the structures of 10 monodesmosidic saponins were assigned unequivocally for the first time, namely, 30-hydroxyglycyrrhizin (1), glycyrrhizin-20-methanoate (2), 24-hydroxyglucoglycyrrhizin (3), rhaoglycyrrhizin (4), 11-deoxorhaoglycyrrhizin (5), rhaoglucoglycyrrhizin (6), rhaogalactoglycyrrhizin (7), 11-deoxo-20α-glycyrrhizin (8), 20α-galacturonoylglycyrrhizin (9), and 20α-rhaoglycyrrhizin (10).

Original language	English
Pages (from-to)	1734-1744
Number of pages	11
Journal	Journal of Natural Products
Volume	81
Issue number	8
DOIs	https://doi.org/10.1021/acs.jnatprod.8b00022
State	Published - 24 Aug 2018
Externally published	Yes

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title = "Saponins from European Licorice Roots (Glycyrrhiza glabra)",

abstract = "European licorice roots (Glycyrrhiza glabra), used in the food and beverage industry due to their distinctive sweet and typical licorice flavor, were fractionated, with the triterpenoid saponins isolated and their chemical structures determined by means of ESIMS, ESIMS/MS, HRESIMS, and 1D/2D NMR experiments. Next to the quantitatively predominant saponin glycyrrhizin (11) and some previously known saponins, the structures of 10 monodesmosidic saponins were assigned unequivocally for the first time, namely, 30-hydroxyglycyrrhizin (1), glycyrrhizin-20-methanoate (2), 24-hydroxyglucoglycyrrhizin (3), rhaoglycyrrhizin (4), 11-deoxorhaoglycyrrhizin (5), rhaoglucoglycyrrhizin (6), rhaogalactoglycyrrhizin (7), 11-deoxo-20α-glycyrrhizin (8), 20α-galacturonoylglycyrrhizin (9), and 20α-rhaoglycyrrhizin (10).",

author = "Christian Schmid and Corinna Dawid and Verena Peters and Thomas Hofmann",

note = "Publisher Copyright: Copyright {\textcopyright} 2018 American Chemical Society and American Society of Pharmacognosy.",

year = "2018",

month = aug,

day = "24",

doi = "10.1021/acs.jnatprod.8b00022",

language = "English",

volume = "81",

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T1 - Saponins from European Licorice Roots (Glycyrrhiza glabra)

AU - Schmid, Christian

AU - Dawid, Corinna

AU - Peters, Verena

AU - Hofmann, Thomas

PY - 2018/8/24

Y1 - 2018/8/24

N2 - European licorice roots (Glycyrrhiza glabra), used in the food and beverage industry due to their distinctive sweet and typical licorice flavor, were fractionated, with the triterpenoid saponins isolated and their chemical structures determined by means of ESIMS, ESIMS/MS, HRESIMS, and 1D/2D NMR experiments. Next to the quantitatively predominant saponin glycyrrhizin (11) and some previously known saponins, the structures of 10 monodesmosidic saponins were assigned unequivocally for the first time, namely, 30-hydroxyglycyrrhizin (1), glycyrrhizin-20-methanoate (2), 24-hydroxyglucoglycyrrhizin (3), rhaoglycyrrhizin (4), 11-deoxorhaoglycyrrhizin (5), rhaoglucoglycyrrhizin (6), rhaogalactoglycyrrhizin (7), 11-deoxo-20α-glycyrrhizin (8), 20α-galacturonoylglycyrrhizin (9), and 20α-rhaoglycyrrhizin (10).

AB - European licorice roots (Glycyrrhiza glabra), used in the food and beverage industry due to their distinctive sweet and typical licorice flavor, were fractionated, with the triterpenoid saponins isolated and their chemical structures determined by means of ESIMS, ESIMS/MS, HRESIMS, and 1D/2D NMR experiments. Next to the quantitatively predominant saponin glycyrrhizin (11) and some previously known saponins, the structures of 10 monodesmosidic saponins were assigned unequivocally for the first time, namely, 30-hydroxyglycyrrhizin (1), glycyrrhizin-20-methanoate (2), 24-hydroxyglucoglycyrrhizin (3), rhaoglycyrrhizin (4), 11-deoxorhaoglycyrrhizin (5), rhaoglucoglycyrrhizin (6), rhaogalactoglycyrrhizin (7), 11-deoxo-20α-glycyrrhizin (8), 20α-galacturonoylglycyrrhizin (9), and 20α-rhaoglycyrrhizin (10).

UR - https://www.scopus.com/pages/publications/85052593097

U2 - 10.1021/acs.jnatprod.8b00022

DO - 10.1021/acs.jnatprod.8b00022

M3 - Article

C2 - 30063346

AN - SCOPUS:85052593097

SN - 0163-3864

VL - 81

SP - 1734

EP - 1744

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 8

ER -

Saponins from European Licorice Roots (Glycyrrhiza glabra)

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