Coumestrol, a New Estrogen Isolated from Forage Crops

Bickoff, E. M.; Booth, A. N.; Lyman, R. Lee; Livingston, A. L.; Thompson, C. R.; DeEds, Floyd

doi:10.1126/science.126.3280.969-a

Cited by 164 publications

(50 citation statements)

References 5 publications

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“…7) is the most potent of the estrogens in forage crops (73) and, consistent with this observation, has a higher binding affinity for the estrogen receptor than genistein (61,74 (74). This seems to be anomalous, because the 12-hydroxyl is free and the 7-hydroxyl is methylated; however, the 6-phenol might be responsible for this effect.…”

Section: Phytoestrogensmentioning

confidence: 60%

Structure-Activity Relationships of Estrogens

Jordan¹,

Mittal²,

Gosden³

et al. 1985

Environmental Health Perspectives

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The last 50 years has seen an exponential rise in the published reports about estrogen action. The model to describe the early events in the mechanism of action of estrogens via the estrogen receptor is updated in this paper to incorporate some of the recent data on the subcellular localization of the receptor. New evidence suggests that the receptor is a nuclear protein, so it appears that estrogens must first diffuse into the nuclear compartment to initiate estrogen action via the receptor complex. This review traces the development of potent estrogenic compounds by the study of their structure-activity relationships. Studies of structure-activity relationships in vivo using Allen Doisy or 3-day uterine weight tests can provide much valuable information, but the assays suffer from the complex problems of pharmacokinetics and metabolic transformation. Studies in vitro using primary cultures of rat pituitary or uterine cells to assay the ability of a compound to induce prolactin synthesis or progesterone receptor synthesis, respectively, can provide essential information about the structural requirements for a compound to produce estrogenic effects. Nevertheless, it should be pointed out that studies in vivo are required to determine whether a compound is metabolically activated to an estrogen. Estrogen receptor binding models are presented to describe the changes in a molecule that will predict high affinity for the ligand and agonist, partial agonist and antagonist properties of the ligand-receptor complex. Most estrogenic pesticides and phytoestrogens comform to the predictions of the estrogen receptor binding model.

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Section: Phytoestrogensmentioning

confidence: 60%

Structure-Activity Relationships of Estrogens

Jordan¹,

Mittal²,

Gosden³

et al. 1985

Environmental Health Perspectives

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“…302 Due to its importance in human nutrition, it has been extensively studied. 303,304 The total synthesis of 319 based on the iron-catalyzed crossdehydrogenative coupling (CDC) was achieved and revealed in 2013.…”

mentioning

confidence: 99%

Total synthesis of natural products containing benzofuran rings

et al. 2017

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Research on natural products containing benzofuran has remarkably increased during the past few decades.Newly isolated natural products with complex structures are being studied, characterized and screened for possible biological activities. Several of such compounds have exhibited various biological activities, thus their total syntheses have attracted much attention from synthetic organic chemists. In this review, we aim to highlight the origins, structures, biological potencies, and synthetic approaches of those natural products bearing at least one benzofuran in their complex structures. Furthermore, we especially focus on the step in which this key heterocycle is installed during the total synthesis of a natural product as the desired target.

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“…The best known representative of this subgroup of compounds is coumestrol [5,9]. It was first identified in 1957 as a clover compound, which has 30 to 100 times higher estrogenic activity than isoflavones [19]. Also, it can be found in spinach, brussels sprout and legumes such as soybeans [20].…”

Section: (2) (2017) 96-106mentioning

confidence: 99%

Classification and biological activity of phytoestrogens: A review

Nikolic¹,

Gajić²,

Tacic³

et al. 2017

Adv Techol

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Phytoestrogens represent polyphenolic and non-steroid compounds that have a similar structure and biological activity as human estrogens. They are the plant secondary metabolites and widespread in over 300 various plant species. The phytoestrogens are divided into two main subgroups, isoflavonoids and lignans. The isoflavonoids are divided into isoflavones and coumestans. Isoflavones are most present in soybean and red clover. A great number of isoflavones has been identified in the plants in the form of non-active glycosides (daidzein and genistein) and in the form of 4'-methylated derivatives (formononetin and biochanin A). Coumestans can also be found in red clover and legumes, while lignans are most present in the flax seed. Coumestans have the most pronounced estrogenic effect of all phytoestrogens. The most famous representative of this subgroup of compounds is coumestrol. Lignans include matairesinol, secoisolariciresinol, lariciresinol, pinoresinol and their metabolites, enterodiol, enterolactone and equol. Numerous studies in animals and humans have shown that phytoestrogens can have protective effects in the estrogen-dependent conditions and estrogen-dependent diseases. It was also shown that the use of phytoestrogens can have a positive effect on insomnia and cognitive functions, i.e. neural disorders, such as Alzheimer's disease. They can express the antioxidant activity in two ways, as the scavengers of free radicals or by the formation of chelating complexes with metal ions. Free metal ions increase the amount of reactive oxygen species by reduction of hydrogen peroxide resulting in a very reactive hydroxyl radical.

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Coumestrol, a New Estrogen Isolated from Forage Crops

Cited by 164 publications

References 5 publications

Structure-Activity Relationships of Estrogens

Structure-Activity Relationships of Estrogens

Total synthesis of natural products containing benzofuran rings

Classification and biological activity of phytoestrogens: A review

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