Glyceollins and dehydroglyceollins isolated from soybean act as SERMs and ER subtype-selective phytoestrogens

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Abstract

Seven prenylated 6a-hydroxy-pterocapans and five prenylated 6a,11a-pterocarpenes with different kinds of prenylation were purified from an ethanolic extract of fungus-treated soybean sprouts. The activity of these compounds toward both human estrogen receptors (hERα and hERβ) was determined in a yeast bioassay and the activity toward hERα was additionally tested in an U2-OS based hERα CALUX bioassay. In the yeast bioassay, compounds with chain prenylation showed in general an agonistic mode of action toward hERα, whereas furan and pyran prenylation led to an antagonistic mode of action. Five of these antagonistic compounds had an agonistic mode of action in the U2-OS based hERα CALUX bioassay, implying that these compounds can act as SERMs. The yeast bioassay also identified 8 ER subtype-selective compounds, with either an antagonistic mode of action or no response toward hERα and an agonistic mode of action toward hERβ. The ER subtype-selective compounds were characterized by 6a-hydroxy-pterocarpan or 6a,11a-pterocarpene backbone structure. It is suggested that either the extra D-ring or the increase in length to 12-13.5 Å of these compounds is responsible for an agonistic mode of action toward hERβ and, thereby, inducing ER subtype-selective behavior.

Original languageEnglish
Pages (from-to)53-63
JournalJournal of Steroid Biochemistry and Molecular Biology
Volume156
DOIs
Publication statusPublished - 1 Feb 2016

Fingerprint

Selective Estrogen Receptor Modulators
Phytoestrogens
Bioassay
Soybeans
Biological Assay
Prenylation
Yeast
Yeasts
Pterocarpans
Pyrans
Fungi
Estrogen Receptors
glyceollin

Keywords

  • 6a,11a-Pterocarpene
  • 6a-Hydroxy-pterocarpan
  • hER yeast bioassay
  • hERα-CALUX
  • Molar extinction coefficient
  • Prenylation

Cite this

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title = "Glyceollins and dehydroglyceollins isolated from soybean act as SERMs and ER subtype-selective phytoestrogens",
abstract = "Seven prenylated 6a-hydroxy-pterocapans and five prenylated 6a,11a-pterocarpenes with different kinds of prenylation were purified from an ethanolic extract of fungus-treated soybean sprouts. The activity of these compounds toward both human estrogen receptors (hERα and hERβ) was determined in a yeast bioassay and the activity toward hERα was additionally tested in an U2-OS based hERα CALUX bioassay. In the yeast bioassay, compounds with chain prenylation showed in general an agonistic mode of action toward hERα, whereas furan and pyran prenylation led to an antagonistic mode of action. Five of these antagonistic compounds had an agonistic mode of action in the U2-OS based hERα CALUX bioassay, implying that these compounds can act as SERMs. The yeast bioassay also identified 8 ER subtype-selective compounds, with either an antagonistic mode of action or no response toward hERα and an agonistic mode of action toward hERβ. The ER subtype-selective compounds were characterized by 6a-hydroxy-pterocarpan or 6a,11a-pterocarpene backbone structure. It is suggested that either the extra D-ring or the increase in length to 12-13.5 {\AA} of these compounds is responsible for an agonistic mode of action toward hERβ and, thereby, inducing ER subtype-selective behavior.",
keywords = "6a,11a-Pterocarpene, 6a-Hydroxy-pterocarpan, hER yeast bioassay, hERα-CALUX, Molar extinction coefficient, Prenylation",
author = "{Van De Schans}, {Milou G.M.} and Vincken, {Jean Paul} and {De Waard}, Pieter and Hamers, {Astrid R.M.} and Bovee, {Toine F.H.} and Harry Gruppen",
year = "2016",
month = "2",
day = "1",
doi = "10.1016/j.jsbmb.2015.11.020",
language = "English",
volume = "156",
pages = "53--63",
journal = "Journal of Steroid Biochemistry and Molecular Biology",
issn = "0960-0760",
publisher = "Elsevier",

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TY - JOUR

T1 - Glyceollins and dehydroglyceollins isolated from soybean act as SERMs and ER subtype-selective phytoestrogens

AU - Van De Schans, Milou G.M.

AU - Vincken, Jean Paul

AU - De Waard, Pieter

AU - Hamers, Astrid R.M.

AU - Bovee, Toine F.H.

AU - Gruppen, Harry

PY - 2016/2/1

Y1 - 2016/2/1

N2 - Seven prenylated 6a-hydroxy-pterocapans and five prenylated 6a,11a-pterocarpenes with different kinds of prenylation were purified from an ethanolic extract of fungus-treated soybean sprouts. The activity of these compounds toward both human estrogen receptors (hERα and hERβ) was determined in a yeast bioassay and the activity toward hERα was additionally tested in an U2-OS based hERα CALUX bioassay. In the yeast bioassay, compounds with chain prenylation showed in general an agonistic mode of action toward hERα, whereas furan and pyran prenylation led to an antagonistic mode of action. Five of these antagonistic compounds had an agonistic mode of action in the U2-OS based hERα CALUX bioassay, implying that these compounds can act as SERMs. The yeast bioassay also identified 8 ER subtype-selective compounds, with either an antagonistic mode of action or no response toward hERα and an agonistic mode of action toward hERβ. The ER subtype-selective compounds were characterized by 6a-hydroxy-pterocarpan or 6a,11a-pterocarpene backbone structure. It is suggested that either the extra D-ring or the increase in length to 12-13.5 Å of these compounds is responsible for an agonistic mode of action toward hERβ and, thereby, inducing ER subtype-selective behavior.

AB - Seven prenylated 6a-hydroxy-pterocapans and five prenylated 6a,11a-pterocarpenes with different kinds of prenylation were purified from an ethanolic extract of fungus-treated soybean sprouts. The activity of these compounds toward both human estrogen receptors (hERα and hERβ) was determined in a yeast bioassay and the activity toward hERα was additionally tested in an U2-OS based hERα CALUX bioassay. In the yeast bioassay, compounds with chain prenylation showed in general an agonistic mode of action toward hERα, whereas furan and pyran prenylation led to an antagonistic mode of action. Five of these antagonistic compounds had an agonistic mode of action in the U2-OS based hERα CALUX bioassay, implying that these compounds can act as SERMs. The yeast bioassay also identified 8 ER subtype-selective compounds, with either an antagonistic mode of action or no response toward hERα and an agonistic mode of action toward hERβ. The ER subtype-selective compounds were characterized by 6a-hydroxy-pterocarpan or 6a,11a-pterocarpene backbone structure. It is suggested that either the extra D-ring or the increase in length to 12-13.5 Å of these compounds is responsible for an agonistic mode of action toward hERβ and, thereby, inducing ER subtype-selective behavior.

KW - 6a,11a-Pterocarpene

KW - 6a-Hydroxy-pterocarpan

KW - hER yeast bioassay

KW - hERα-CALUX

KW - Molar extinction coefficient

KW - Prenylation

U2 - 10.1016/j.jsbmb.2015.11.020

DO - 10.1016/j.jsbmb.2015.11.020

M3 - Article

VL - 156

SP - 53

EP - 63

JO - Journal of Steroid Biochemistry and Molecular Biology

JF - Journal of Steroid Biochemistry and Molecular Biology

SN - 0960-0760

ER -