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

Haajanen, Kati; Botting, Nigel P.

doi:10.1016/j.steroids.2005.10.005

Cited by 16 publications

(17 citation statements)

References 43 publications

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“…A trial of the final deprotection step on 8 using catalytic hydrogenation over Pd/C showed this to be ineffective. However, following previous reports, use of an excess of Raney 1 nickel 16 in THF-ethanol (1 : 1) 17 proved to be effective and gave the symmetrical bibenzyl 10, already a known compound, 18 in moderate yield. When this method was applied to a sample of 9, the target compound 1 was formed and was found to be spectroscopically identical to the natural product, although the repeated chromatographic purification required to remove residual traces of 10 and produce an analytically pure sample meant that the final yield was rather low.…”

supporting

confidence: 65%

Isolation, structure determination and synthesis of a trichlorodihydroxybibenzyl from a terrestrial plant

et al. 2013

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supporting

confidence: 65%

Isolation, structure determination and synthesis of a trichlorodihydroxybibenzyl from a terrestrial plant

et al. 2013

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“…13 C 3 -biochanin A, 13 C 3 -daidzein, 13 C 3 -genistein, 13 C 3 -glycitein, 13 C 3 -formononetin, 13 C 3 -matairesinol, 13 C 3 -secosiolariciresinol, and 13 C 3 -enterolactone were obtained from Dr. Nigel Botting (University of St Andrews, Fife, UK) (36)(37)(38)(39). β-glucuronidase (from Helix Pomatia), β-glucosidase (from almonds), and cellulase (from Trichoderma reesi) were purchased from Sigma (Poole, Dorset, UK).…”

Section: Chemicalsmentioning

confidence: 99%

Phytoestrogen Content of Cereals and Cereal-Based Foods Consumed in the UK

Kuhnle

Dell'Aquila

Aspinall

et al. 2009

Nutrition and Cancer

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Dietary phytoestrogens may be involved in the occurrence of chronic diseases. Reliable information on the phytoestrogen content in foods is required to assess dietary exposure and disease risk in epidemiological studies. However, there is little information on isoflavone, lignan, and coumestrol content of cereals and cereal-based foods, leading to an underestimation of intake. This is the first study of phytoestrogens (isoflavones: biochanin A, daidzein, formononetin, genistein, glycitein; lignans: matairesinol, secoisplariciresinol; coumestrol) in a comprehensive selection of 101 cereals and cereal-based foods-including breads, breakfast cereals, biscuits, pasta and rice-consumed in the UK using a sensitive LCMS technique with 13C-labelled internal standards. Phytoestrogens were detected in all foods analyzed; bread contained the highest amount of phytoestrogens-many as isoflavones-with an average content of 375 +/- 67 microg/100 g wet weight (excluding soya-linseed bread with 12,000 microg/100 g). Most other foods contained less than 100 microg/100 g, many as lignans. Our study shows that all foods analyzed contained phytoestrogens, with the highest amount found in breads, making them one of the main sources of dietary phytoestrogens in the UK. These results will allow a more accurate estimation of exposure to dietary phytoestrogens.

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“…40,41 After the first 13 C label was introduced, this synthesis took 11 or 12 steps to obtain the final triply labeled target, and although the yields for most of the steps are very good, the overall yields were 0.3−2%. 40,41 On the other hand, deuterium labeling provides by far the most important route to stable isotope labeled standards in organic analysis. This is a result from the wide distribution of hydrogen in the target material, the ease of H/D exchange in most cases, and the cheap and ready availability of deuterated solvents and reagents.…”

Section: ■ Labels For Lignansmentioning

confidence: 99%

“…Only one total synthesis of stable 13 C-labeled lignan derivatives has been reported in the literature. 40,41 After the first 13 C label was introduced, this synthesis took 11 or 12 steps to obtain the final triply labeled target, and although the yields for most of the steps are very good, the overall yields were 0.3−2%. 40,41 On the other hand, deuterium labeling provides by far the most important route to stable isotope labeled standards in organic analysis.…”

Section: ■ Labels For Lignansmentioning

confidence: 99%

Electrophilic Aromatic Deuteration of Lignans: Mostly Reliable but Occasionally Aberrant Selectivities

Pohjoispää

Wähälä

2015

J. Agric. Food Chem.

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Lignans are a ubiquitous group of natural products of plant or mammalian origin. In the human diet, especially in fiber-rich foods, there are measurable amounts of lignans. Lignan intake is associated with a reduced risk of a range of chronic Western diseases, and in studying these compounds and their biological activity, authentic stable isotope labeled analogues are needed. This review summarizes the reported labeling methods and discusses the selectivity and reactivity in the electrophilic aromatic deuteration of lignans where recently a number of unexpected selectivities or nonselectivities have been encountered.

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

Cited by 16 publications

References 43 publications

Isolation, structure determination and synthesis of a trichlorodihydroxybibenzyl from a terrestrial plant

Isolation, structure determination and synthesis of a trichlorodihydroxybibenzyl from a terrestrial plant

Phytoestrogen Content of Cereals and Cereal-Based Foods Consumed in the UK

Electrophilic Aromatic Deuteration of Lignans: Mostly Reliable but Occasionally Aberrant Selectivities

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