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Structural Changes of 6a-Hydroxy-Pterocarpans Upon Heating Modulate Their Estrogenicity
- Source :
- Journal of Agricultural and Food Chemistry, 62, 10475-10484, Journal of Agricultural and Food Chemistry 62 (2014)
- Publication Year :
- 2014
- Publisher :
- American Chemical Society (ACS), 2014.
-
Abstract
- The isoflavonoid composition of an ethanolic extract of fungus-treated soybean sprouts was strongly altered by a combined acid/heat treatment. UHPLC-MS analysis showed that 6a-hydroxy-pterocarpans were completely converted to their respective, more stable, 6a,11a-pterocarpenes, whereas other isoflavonoids, from the isoflavone and coumestan subclasses, were affected to a much lesser extent (loss of ~15%). Subsequently, mixtures enriched in prenylated 6a-hydroxy-pterocarpans (pools of glyceollin I/II/III and glyceollin IV/VI) or prenylated 6a,11a-pterocarpenes (pools of dehydroglyceollin I/II/III and dehydroglyceollin IV/VI) were purified, and tested for activity on both human estrogen receptors (ERa and ERß). In particular, the response toward ERa changed, from agonistic for glyceollins to antagonistic for dehydroglyceollins. Toward ERß a decrease in agonistic activity was observed. These results indicate that the introduction of a double bond with the concomitant loss of a hydroxyl group in 6a-hydroxy-pterocarpans extensively modulates their estrogenic activity.
- Subjects :
- Hot Temperature
Novel Foods & Agrochains
Pterocarpans
BU Toxicologie
Stereochemistry
Genistein
Estrogen receptor
aglycones
Novel Foods & Agroketens
ionization mass-spectrometry
genistein
soy
chemistry.chemical_compound
Isoflavonoid
Coumestan
Levensmiddelenchemie
Glyceollin I
Humans
BU Toxicology, Novel Foods & Agrochains
isoflavonoid composition
VLAG
Glyceollin
phytoestrogens
Molecular Structure
Food Chemistry
Plant Extracts
BU Toxicology
seedlings
Daidzein
Estrogens
General Chemistry
Kinetics
Receptors, Estrogen
BU Toxicologie, Novel Foods & Agroketens
chemistry
Biochemistry
flavonoids
Phytoestrogens
Soybeans
daidzein
General Agricultural and Biological Sciences
Subjects
Details
- ISSN :
- 15205118 and 00218561
- Volume :
- 62
- Database :
- OpenAIRE
- Journal :
- Journal of Agricultural and Food Chemistry
- Accession number :
- edsair.doi.dedup.....1622c588ebf814b589072c747d3053e3