Coumestrol
Names | |
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IUPAC name
3,9-Dihydroxypterocarp-6a(11a)-en-6-one
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Systematic IUPAC name
3,9-Dihydroxy-6H-[1]benzofuro[3,2-c][1]benzopyran-6-one | |
Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.006.842 |
EC Number |
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KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C15H8O5 | |
Molar mass | 268.224 g·mol−1 |
Melting point | 385 °C (725 °F; 658 K) (decomposes)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Coumestrol is a natural
Coumestrol is a
The chemical shape of coumestrol orients its two
Natural sources and dietary intake
Levels of coumestrol within individual plants of the same species are variable. Studies of coumestrol levels in alfalfa suggest that there may be a positive correlation between coumestrol production and infection of the plant by
According to the
Food Item | Coumestrol Level (mg/100g) |
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Large, dry Lima beans |
0.14 |
Raw Pinto Beans |
1.80 |
Dry Kala Chana | 6.13 |
Alfalfa Sprouts | 1.60 |
Raw Clover Sprouts | 14.08 |
Soy Sprouts | 0.34 |
Mature Soy Beans |
0.02 |
Unfortified Original and Vanilla Soy milk | 0.81 |
Firm Magnesium Chloride |
0.12 |
Doughnuts with Soy Flour of Protein | 0.24 |
Based on extrapolation from studies done on animals, the maximum tolerable daily intake of coumestrol for human beings has been estimated at 22 μg per kg of body mass. This was calculated by extrapolating from the lowest level at which adverse effects were seen in animals. Although due to the variability of the human diet, the exact amount of coumestrol the average person consumes has not been calculated, studies of phytoestrogen intake suggest that most human diets result in a negligible intake of coumestrol relative to the maximum tolerable daily intake.[12]
Biological effects on mammals
PMID 36145197). . (October 2022) |
Because coumestrol is an estrogen mimic, it is an endocrine disruptor with the potential to affect all organ systems that are regulated hormonally via estrogens.
Nervous system
Coumestrol and other phytoestrogens have been shown to have an effect on sexual behavior in rats by antagonizing the action of estrogen within the brain; male rats that nursed from females with coumestrol in their diets were both less likely to mount a female rat and less likely to ejaculate, despite producing normal levels of
Reproductive system
Coumestrol has been shown to accelerate the onset of puberty in mice.
Skeletal system
Coumestrol has been shown to decrease
Genotoxicity
Coumestrol has been shown to have
Metabolism
Studies have shown that coumestrol has beneficial properties on carbohydrate metabolism in ovariectomized rats, decreasing glycogen levels in skeletal muscle. There is also data indicating that coumestrol lowers plasma cholesterol levels in chicks. These results point to a possibility of coumestrol having a positive role to play against human obesity and diabetes in the future.[18]
Menopause
Coumestrol and other phytoestrogens are sometimes used as a substitute for hormone therapy in the treatment of
Breast cancer
Coumestrol and other phytoestrogens have also been investigated as a possible substitute for hormone therapy and chemotherapy in breast cancer patients. The results of various studies regarding the use of phytoestrogens in treating breast cancer have been somewhat contradictory and ambiguous, and as a result, researchers cannot clearly define phytoestrogens like coumestrol as being chemoprotective agents or potentially having negative effects, such as inducing further growth of existing breast cancer tumors by activating ERα receptors.[20] Researchers at
Current and future research
Most research on the biological effects of coumestrol has been conducted on animals because of ethical concerns. There is a need for more human studies to better understand potential human health impacts due to exposure.[18] In addition, further research is required to fully understand the biosynthesis pathway of coumestrol, although it is believed to be similar to that of flavones and isoflavones. Further research is required to understand the exact nature of the relationship between the levels of coumestrol in a plant and the plant's response to pathogens.[10]
References
- PMID 14255129.
- PMID 13486041.
- ^ a b Bhagwat, Seema; Haytowitz, David; Holden, Joanne (September 2008). USDA Database for the Isoflavone Content of Selected Foods (PDF) (Release 2.0 ed.). Beltsville, Maryland: U.S. Department of Agriculture. Retrieved 10 March 2015.
- S2CID 32550431.
- PMID 9048584.
- PMID 9751507.
- S2CID 85373016.
- S2CID 54388469.
- PMID 18221056.
- ^ a b c United States Department of Agriculture (2003). Studies on the Chemical and Biological Properties of Coumestrol and Related Compounds. US Government Printing Office. pp. 47–67. Archived from the original on 2015-04-02. Retrieved 2015-03-17.
- ^ "USDA-Iowa State University Database on the Isoflavone Content of Foods" (PDF). Retrieved 10 March 2022.
- ^ ISBN 9781845695743.
- ^ PMID 11836071.
- ^ ISBN 9780849322815.
- ^ PMID 22223686.
- ^ Perez-Rivero, Juan; Aguilar-Setien, Alvaro; Martinez-Maya, Jos; Perez-Martino, Mario; Serrano, Hector. "Phytoestrogens and Effect of Consumption and Their Effects in Different Organs and Systems of Domestic Animals". Agricultura Tecnica. 67 (3).
- PMID 15914213.
- ^ ISBN 978-1-84973-509-4.
- PMID 24323914.
- PMID 18414622.
- PMID 24894196.
Further reading
- Kshirsagar, U.A.; Parnes, R.; Goldshtein, H.; Ofir, R.; Zarivach, R.; Pappo, D. (2013). "Aerobic iron-based cross-dehydrogenative coupling enables efficient diversity-oriented synthesis of coumestrol-based selective estrogen receptor modulators". Chem. Eur. J. 19 (40): 13575–13583. PMID 23946113.