Synthesis of multiply 13C-labeled furofuran lignans using 13C-labeled cinnamyl alcohols as building blocks

K Haajanen; Nigel Peter Botting

doi:10.1016/j.steroids.2005.10.005

Synthesis of multiply ¹³C-labeled furofuran lignans using ¹³C-labeled cinnamyl alcohols as building blocks

K Haajanen, Nigel Peter Botting

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

Abstract

Plant lignans are currently being widely studied for their potential benefits for human health as their consumption has been correlated with lower risks for developing chronic diseases, such as breast cancer and coronary heart disease. However, studies of some classes of lignans, in particular the furofurans, are hampered by the lack of suitable standards to allow accurate analysis. Herein, we report the syntheses of two racemic C-13-labeled furofuran lignans [7,8,9-C-13(3)]medioresinol and [7,8, 9-C-13(3)]sesamin as internal standards for LC-MS analysis. The labeled furofuran lignans were constructed from triply labeled cinnamyl alcohols, using a radical cyclization method. (c) 2005 Elsevier Inc. All rights reserved.

Original language	English
Pages (from-to)	231-239
Number of pages	9
Journal	Steroids
Volume	71
Issue number	3
DOIs	https://doi.org/10.1016/j.steroids.2005.10.005
Publication status	Published - Mar 2006

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

lignan
furofuran
phytoestrogen
isotopic labeling
synthesis
analysis
METAL RADICAL SOURCE
TRANSITION-METAL
MAMMALIAN LIGNANS
BREAST-CANCER
ENTEROLACTONE
PLANT
CYCLIZATION
METABOLISM
PRECURSORS
ENTERODIOL

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Cite this

@article{7f81910482bc4f26a73dbfd9830346df,

title = "Synthesis of multiply 13C-labeled furofuran lignans using 13C-labeled cinnamyl alcohols as building blocks",

abstract = "Plant lignans are currently being widely studied for their potential benefits for human health as their consumption has been correlated with lower risks for developing chronic diseases, such as breast cancer and coronary heart disease. However, studies of some classes of lignans, in particular the furofurans, are hampered by the lack of suitable standards to allow accurate analysis. Herein, we report the syntheses of two racemic C-13-labeled furofuran lignans [7,8,9-C-13(3)]medioresinol and [7,8, 9-C-13(3)]sesamin as internal standards for LC-MS analysis. The labeled furofuran lignans were constructed from triply labeled cinnamyl alcohols, using a radical cyclization method. (c) 2005 Elsevier Inc. All rights reserved.",

keywords = "lignan, furofuran, phytoestrogen, isotopic labeling, synthesis, analysis, METAL RADICAL SOURCE, TRANSITION-METAL, MAMMALIAN LIGNANS, BREAST-CANCER, ENTEROLACTONE, PLANT, CYCLIZATION, METABOLISM, PRECURSORS, ENTERODIOL",

author = "K Haajanen and Botting, \{Nigel Peter\}",

year = "2006",

month = mar,

doi = "10.1016/j.steroids.2005.10.005",

language = "English",

volume = "71",

pages = "231--239",

journal = "Steroids",

issn = "0039-128X",

publisher = "Elsevier Inc.",

number = "3",

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TY - JOUR

T1 - Synthesis of multiply 13C-labeled furofuran lignans using 13C-labeled cinnamyl alcohols as building blocks

AU - Haajanen, K

AU - Botting, Nigel Peter

PY - 2006/3

Y1 - 2006/3

N2 - Plant lignans are currently being widely studied for their potential benefits for human health as their consumption has been correlated with lower risks for developing chronic diseases, such as breast cancer and coronary heart disease. However, studies of some classes of lignans, in particular the furofurans, are hampered by the lack of suitable standards to allow accurate analysis. Herein, we report the syntheses of two racemic C-13-labeled furofuran lignans [7,8,9-C-13(3)]medioresinol and [7,8, 9-C-13(3)]sesamin as internal standards for LC-MS analysis. The labeled furofuran lignans were constructed from triply labeled cinnamyl alcohols, using a radical cyclization method. (c) 2005 Elsevier Inc. All rights reserved.

AB - Plant lignans are currently being widely studied for their potential benefits for human health as their consumption has been correlated with lower risks for developing chronic diseases, such as breast cancer and coronary heart disease. However, studies of some classes of lignans, in particular the furofurans, are hampered by the lack of suitable standards to allow accurate analysis. Herein, we report the syntheses of two racemic C-13-labeled furofuran lignans [7,8,9-C-13(3)]medioresinol and [7,8, 9-C-13(3)]sesamin as internal standards for LC-MS analysis. The labeled furofuran lignans were constructed from triply labeled cinnamyl alcohols, using a radical cyclization method. (c) 2005 Elsevier Inc. All rights reserved.

KW - lignan

KW - furofuran

KW - phytoestrogen

KW - isotopic labeling

KW - synthesis

KW - analysis

KW - METAL RADICAL SOURCE

KW - TRANSITION-METAL

KW - MAMMALIAN LIGNANS

KW - BREAST-CANCER

KW - ENTEROLACTONE

KW - PLANT

KW - CYCLIZATION

KW - METABOLISM

KW - PRECURSORS

KW - ENTERODIOL

UR - https://www.scopus.com/pages/publications/32244438629

U2 - 10.1016/j.steroids.2005.10.005

DO - 10.1016/j.steroids.2005.10.005

M3 - Article

SN - 0039-128X

VL - 71

SP - 231

EP - 239

JO - Steroids

JF - Steroids

IS - 3

ER -