Synthesis, isolation and identification of glucuronides and mercapturic acids of a novel antiparasitic agent, licochalcone A

L. Nadelmann; J. Tjornelund; S. H. Hansen; Claus Cornett; U. G. Sidelmann; U. Braumann; E. Christensen; S. B. Christensen

Synthesis, isolation and identification of glucuronides and mercapturic acids of a novel antiparasitic agent, licochalcone A

L. Nadelmann, J. Tjornelund, S. H. Hansen, Claus Cornett, U. G. Sidelmann, U. Braumann, E. Christensen, S. B. Christensen

9 Citations (Scopus)

Abstract

1. Four glucuronic acid conjugates of licochalcone A (Lica), and their metabolites, have been synthesized using rabbit and pig liver microsomes and purified by preparative hplc. 2. The glucuronides were identified as E-Lica 4'-O-beta-glucuronide, E and Z-Lica 4-O-beta-glucuronide and a mono-glucuronide conjugate of a beta-hydroxylated Lica metabolite. The metabolites were identified by hplc-nmr (one and two-dimensional nmr) as well as hplc-ms. 3. At pH 8.5 Lica reacted with N-acetyl-L-cysteine giving the two epimeric conjugates, which were then isolated by preparative hplc and identified by one and two-dimensional nmr spectroscopic methods. 4. Only two glucuronic acid conjugates (E- and Z-Lica 4-O-beta-glucuronide) were found in the urine of rat after i.p. administration of a single dose of Lica.

Original language	Undefined/Unknown
Journal	Xenobiotica
Volume	27
Issue number	7
Pages (from-to)	667-680
Number of pages	14
ISSN	0049-8254
Publication status	Published - 1997

Cite this

@article{bfc7a04fa4204650a938d6dc0b3626c9,

title = "Synthesis, isolation and identification of glucuronides and mercapturic acids of a novel antiparasitic agent, licochalcone A",

abstract = "1. Four glucuronic acid conjugates of licochalcone A (Lica), and their metabolites, have been synthesized using rabbit and pig liver microsomes and purified by preparative hplc. 2. The glucuronides were identified as E-Lica 4'-O-beta-glucuronide, E and Z-Lica 4-O-beta-glucuronide and a mono-glucuronide conjugate of a beta-hydroxylated Lica metabolite. The metabolites were identified by hplc-nmr (one and two-dimensional nmr) as well as hplc-ms. 3. At pH 8.5 Lica reacted with N-acetyl-L-cysteine giving the two epimeric conjugates, which were then isolated by preparative hplc and identified by one and two-dimensional nmr spectroscopic methods. 4. Only two glucuronic acid conjugates (E- and Z-Lica 4-O-beta-glucuronide) were found in the urine of rat after i.p. administration of a single dose of Lica.",

keywords = "performance liquid-chromatography magnetic-resonance spectroscopy dynamically modified silica h-1-nmr spectroscopy glutathione adduct metabolites urine leishmania ibuprofen mice",

author = "L. Nadelmann and J. Tjornelund and Hansen, {S. H.} and Claus Cornett and Sidelmann, {U. G.} and U. Braumann and E. Christensen and Christensen, {S. B.}",

year = "1997",

language = "Udefineret/Ukendt",

volume = "27",

pages = "667--680",

journal = "Xenobiotica",

issn = "0049-8254",

publisher = "Taylor & Francis",

number = "7",

}

TY - JOUR

T1 - Synthesis, isolation and identification of glucuronides and mercapturic acids of a novel antiparasitic agent, licochalcone A

AU - Nadelmann, L.

AU - Tjornelund, J.

AU - Hansen, S. H.

AU - Cornett, Claus

AU - Sidelmann, U. G.

AU - Braumann, U.

AU - Christensen, E.

AU - Christensen, S. B.

PY - 1997

Y1 - 1997

N2 - 1. Four glucuronic acid conjugates of licochalcone A (Lica), and their metabolites, have been synthesized using rabbit and pig liver microsomes and purified by preparative hplc. 2. The glucuronides were identified as E-Lica 4'-O-beta-glucuronide, E and Z-Lica 4-O-beta-glucuronide and a mono-glucuronide conjugate of a beta-hydroxylated Lica metabolite. The metabolites were identified by hplc-nmr (one and two-dimensional nmr) as well as hplc-ms. 3. At pH 8.5 Lica reacted with N-acetyl-L-cysteine giving the two epimeric conjugates, which were then isolated by preparative hplc and identified by one and two-dimensional nmr spectroscopic methods. 4. Only two glucuronic acid conjugates (E- and Z-Lica 4-O-beta-glucuronide) were found in the urine of rat after i.p. administration of a single dose of Lica.

AB - 1. Four glucuronic acid conjugates of licochalcone A (Lica), and their metabolites, have been synthesized using rabbit and pig liver microsomes and purified by preparative hplc. 2. The glucuronides were identified as E-Lica 4'-O-beta-glucuronide, E and Z-Lica 4-O-beta-glucuronide and a mono-glucuronide conjugate of a beta-hydroxylated Lica metabolite. The metabolites were identified by hplc-nmr (one and two-dimensional nmr) as well as hplc-ms. 3. At pH 8.5 Lica reacted with N-acetyl-L-cysteine giving the two epimeric conjugates, which were then isolated by preparative hplc and identified by one and two-dimensional nmr spectroscopic methods. 4. Only two glucuronic acid conjugates (E- and Z-Lica 4-O-beta-glucuronide) were found in the urine of rat after i.p. administration of a single dose of Lica.

KW - performance liquid-chromatography magnetic-resonance spectroscopy dynamically modified silica h-1-nmr spectroscopy glutathione adduct metabolites urine leishmania ibuprofen mice

M3 - Tidsskriftartikel

SN - 0049-8254

VL - 27

SP - 667

EP - 680

JO - Xenobiotica

JF - Xenobiotica

IS - 7

ER -