Synthesis of xanthohumol and xanthohumol-d3 from naringenin

被引：5

作者：

Andrusiak, Joanna ^{[1
,2
]}

Mylkie, Kinga ^{[3
,4
]}

Wysocka, Malgorzata ^{[2
]}

Scianowski, Jacek ^{[1
]}

Wolan, Andrzej ^{[1
,2
]}

Budny, Marcin ^{[2
]}

机构：

[1] Nicolaus Copernicus Univ, Dept Organ Chem, Fac Chem, Gagarina 7, PL-87100 Torun, Poland

[2] Synthex Technol Sp Zoo, Gagarina 7-134B, PL-87100 Torun, Poland

[3] Nicolaus Copernicus Univ, Dept Biomed & Polymer Chem, Fac Chem, Gagarina 7, PL-87100 Torun, Poland

[4] Noctiluca SA, Gagarina 7-41B, PL-87100 Torun, Poland

来源：

RSC ADVANCES | 2021年 / 11卷 / 46期

关键词：

HOPS; 8-PRENYLNARINGENIN; CONSTITUENTS; BEER;

D O I：

10.1039/d1ra05443k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A six-step synthesis of xanthohumol (1a) and its d(3)-derivative (1b) from easily accessible naringenin is reported. The prenyl side chain was introduced by Mitsunobu reaction followed by the europium-catalyzed Claisen rearrangement and base-mediated opening of chromanone gave access to an alpha,beta-conjugated ketone system. Compound 1b was used as an internal standard in stable isotope dilution assays of 1a in two Polish beers.

引用

页码：28934 / 28939

页数：6

共 28 条

[1] Trends in Utilization of the Pharmacological Potential of Chalcones [J].

Batovska, Daniela Ilieva ;

Todorova, Iva Todorova .

CURRENT CLINICAL PHARMACOLOGY, 2010, 5 (01) :1-29

[2] 13C-labelling of xanthohumol in hop cones (Humulus lupulus) [J].

Berwanger, S ;

Zapp, J ;

Becker, H .

PLANTA MEDICA, 2005, 71 (06) :530-534

[3]

Buckett L., 2020, FRONT NUTR, P319

[4] A primer of deuterium in drug design [J].

Cargnin, Sarah ;

Serafini, Marta ;

Pirali, Tracey .

FUTURE MEDICINAL CHEMISTRY, 2019, 11 (16) :2039-2042

[5] Stable isotope- labeling studies in metabolomics: new insights into structure and dynamics of metabolic networks [J].

Chokkathukalam, Achuthanunni ;

Kim, Dong-Hyun ;

Barrett, Michael P. ;

Breitling, Rainer ;

Creek, Darren J. .

BIOANALYSIS, 2014, 6 (04) :511-524

[6]

Ciccimaro E, 2010, BIOANALYSIS, V2, P311, DOI [10.4155/bio.09.185, 10.4155/BIO.09.185]

[7] Total synthesis of [13C]2-, [13C]3-, and [13C]5-isotopomers of xanthohumol, the principal prenylflavonoid from hops [J].

Ellinwood, Duncan C. ;

El-Mansy, Mohamed F. ;

Plagmann, Layhna S. ;

Stevens, Jan F. ;

Maier, Claudia S. ;

Gombart, Adrian F. ;

Blakemore, Paul R. .

JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2017, 60 (14) :639-648

[8] Beer constituents as potential cancer chemopreventive agents [J].

Gerhäuser, C .

EUROPEAN JOURNAL OF CANCER, 2005, 41 (13) :1941-1954

[9]

Gerhauser C, 2002, MOL CANCER THER, V1, P959

[10] An efficient synthesis of the potent phytoestrogens 8-prenylnaringenin and 6-(1,1-dimethylallyl)naringenin by europium(III)-catalyzed Claisen rearrangement [J].

Gester, S ;

Metz, P ;

Zierau, O ;

Vollmer, G .

TETRAHEDRON, 2001, 57 (06) :1015-1018

← 1 2 3 →