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Chemopreventive Agents
Published in David E. Thurston, Ilona Pysz, Chemistry and Pharmacology of Anticancer Drugs, 2021
Coumestrol (Figure 12.17) has a structure based on the central core of the family of naturally occurring phytoestrogen compounds known as the coumestans. Coumestrol is found in spinach, brussels sprouts, soy beans, and a variety of legumes. The highest concentrations are found in clover, kala chana (a type of chick pea), and alfalfa sprouts, but it is also present in lima and pinto beans, and split peas. Red clover is thought to contain the highest percentage of coumestrol at a level of approximately 1.3 g/ 100 g. Based on animal toxicity studies, the maximum tolerable daily intake for humans is calculated to be 22 µg/kg. As with many phytoestrogens, coumestrol can pass through cell membranes readily due to its relatively low molecular weight (i.e., 268.22) and favorable physicochemical properties, after which it is thought to interact with various enzymes and receptors. Structure of coumestrol.
Long-Term Effects of Perinatal Treatment with Sex Steroids and Related Substances on Reproductive Organs of Female Mice
Published in Takao Mori, Hiroshi Nagasawa, Toxicity of Hormones in Perinatal Life, 2020
John-Gunnar Forsberg, Taisen Iguchi
It is of interest that treatment with coumestrol, estrogen isolated from the ladino clover, also induces irreversible changes in the mouse vaginal epithelium57 since this finding suggests the possible involvement of dietary estrogen in the production of human vaginal lesions.58,59 The predominant dietary estrogens to which humans are exposed are naturally occurring phytoestrogens, rather than synthetic estrogens, e.g., DES.60 Under certain circumstances, phytoestrogens may reach circulating levels high enough to exert effects on the vaginas in animals ingesting them. A well-known example is hyperestrogenization and subsequent infertility in sheep grazing clover.60-62 Some fungi produce estrogenic mycotoxins, e.g., zearalenone produced by Fusarium fungi infesting stored corn. The “moldy corn syndrome” observed in female pigs fed corn contaminated with Fusarium involves vaginal prolapse and infertility.59 It is worth noting that the presence of coumestrol and other naturally occurring estrogenic substances in food could contribute to potential hazard to humans.57,59
Formulated Natural Selective Estrogen Receptor Modulators: A Key To Restoring Women’s Health
Published in Megh R. Goyal, Durgesh Nandini Chauhan, Plant- and Marine-Based Phytochemicals for Human Health, 2018
A. Anita Margret, S. Aishwarya, J. Theboral
Coumestrol and 4′-O-methoxycoumestrol are the predominant compounds that have exhibited estrogenic activity. They exhibit close structural resemblance with isoflavones. The main dietary source of coumestrol is legumes and low levels have been reported in Brussel sprouts and spinach.27, 32, 48 Clover and soybean sprouts are reported to have the highest concentration, 28 and 7 mg/100 g dry wt., respectively; mature soybeans only have 0.12 mg/100 g dry wt. Although there are a large number of coumestans, only a small number has shown estrogenic activity, and their metabolism in human being is modest. Though, coumestans have not widely established its progeny from the group of isoflavonoids and anticipated as an efficient phytocompound to conjecture a wide source of well-being against ailments.77
An insight into the neuroprotective effects and molecular targets of pomegranate (Punica granatum
) against Alzheimer’s disease
Published in Nutritional Neuroscience, 2023
Namy George, Majed AbuKhader, Khalid Al Balushi, Bushra Al Sabahi, Shah Alam Khan
Pirzadeh et al. in 2020 have reviewed in detail the chemical constituents present in the pomegranate fruit extract which proved to contain approximately 85.4% water, 10.6% sugar, 1.4% pectin and 0.2–1% polyphenols [30]. Most of the antioxidant property of the fruit is due to the water-soluble tannins found in the peel which accounts for nearly 92% of the total antioxidant activity. Tannins are capable of undergoing hydrolysis with and without the help of enzymes. Ellagitannins (ETs), gallotannins and punicalagin are some of the hydrolyzable tannins present in the different parts of the pomegranate. As a matter of fact, the hydrolzyed products like ellagic acid are partly metabolized by gut bacteria producing demethyellagic acid glucuronide, urolithin derivatives and several other metabolites. These metabolites could also be responsible for the health benefits of the consumption of pomegranate [44]. Furthermore, pomegranate seed oil (PSO) consists of fatty acids such as punicic acid, linoleic acid and oleic acids (Figure 1). The major constituents of PSO are steroidal and non-steroidal estrogens. Steroidal estrogen in the seed oil comprises tocopherol, testosterone, stigmasterol, β-estrolsitosterol, 17-α-estradiol and the nonsteroidal estrogen comprises coumestrol and campestral [30]. There is a high variation seen in the pomegranate’s bioactive constituents depending upon the environmental conditions it is grown [5].
Effects of mono- and dialkylglucosides on the characterisation and blood circulation of lipid nanoemulsions
Published in Journal of Microencapsulation, 2019
Shigehiko Takegami, Atsuko Konishi, Shizuno Okazaki, Mai Fujiwara, Tatsuya Kitade
In recent years, lipid nanoemulsions (LNE) have been the focus of DDS research and have been investigated as carriers for a variety of useful drugs, for example, paclitaxel (Chen et al.2017), doxorubicin or its prodrug (Camara et al.2017, Liu et al.2017), and doxorubicin and bromotetrandrine (Cao et al.2015) for cancer treatment; darunavir (Desai and Thakkar 2019) and coumestrol (Argenta et al.2018) as antivirals; diclofenac acid (Madishetty et al.2015) as an anti-inflammatory; methotrexate (Fiorelli et al.2017) for the treatment of cardiac allograft vasculopathy; and isoflurane (Natalini et al.2017) and xenon (Kim et al.2017) for anaesthesia. In addition, we have developed an LNE prepared from a lipid mixture of soybean oil (SO), egg yolk phosphatidylcholine (PC), sodium palmitate (PANa), and sucrose fatty acid ester (Takegami et al.2008). As the mean droplet size of our LNE is approximately 50 nm, it was investigated as a DDS for cancer therapy (Takegami et al.2010a, 2010b, 2016) because LNEs with droplet sizes of less than 100 nm accumulate passively in tumour tissues (Seki et al.1994, Miyamoto et al.1999) as a result of the enhanced permeation and retention (EPR) effect (Matsumura and Maeda 1986, Maeda 1991, Maeda et al.2000).
Depletion of dietary phytoestrogens reduces hippocampal plasticity and contextual fear memory stability in adult male mouse
Published in Nutritional Neuroscience, 2021
Gürsel Çalışkan, Syed Ahsan Raza, Yunus E. Demiray, Emre Kul, Kiran V. Sandhu, Oliver Stork
Male mice were group-caged (3–6 mice per cage) and supplied with a standard phytoestrogen-containing diet (ssniff R/M-H, 10 mm, V1534) that was composed of cereals (wheat products, barley) and approximately 23% soybean products, and contained 19% crude protein, 3.3% crude fat, 4.9% crude fiber and 6.4% crude ash. The concentration of daidzein and genistein in the diet were determined as 140–150 and 140–200 mg/kg, respectively. The concentration of coumestrol was <1 mg/kg. To account for the average cumulative value of phytoestrogens in the diet, we termed it ‘phyto-300’.