Isoflavones, or 3-phenyl derivatives, are a class of heterocyclic phenolic compounds produced during plant metabolism and are a type of secondary plant metabolite. Isoflavones are mainly found in leguminous plants. Soy isoflavones were discovered by American scientists in 1986. They have a relatively simple molecular formula of C15H10O2, are yellow-white solid powders and have a melting point of 295°C-339°C. They are essentially insoluble in water but readily soluble in weakly polar solvents such as methanol, acetone, ethyl acetate and ethanol. Soy isoflavones found in soybeans have two chemical forms, bound glycosides and free aglycones. Most of the soy isoflavones are in the form of glycosides: glucoside, 6"-0-malonylglucoside and 6"-0-acetylglucoside, accounting for 97-98% of the total soy isoflavone content. A small proportion is present in the form of aglycones, i.e. in the free form, accounting for 2%-3% of the total soy isoflavone content. However, the biological activity of soy isoflavones is highest in the form of aglycones. The soy isoflavones naturally present in soybeans can currently be isolated into 12 types, of which 9 are glycoside types and the other 3 are corresponding aglycone types. These 12 soy isoflavones can also be divided into three main categories, namely daidzein, daidzein and genistein.
Figure 1. Structure of important isoflavones.( Sohn SI, et al.; 2021)
Soy isoflavones are the main natural active substances in soybeans, among which the free glycosides, i.e., aglycones, which are less in content, are the main active components. Research on the physiological activity of soy isoflavones began in the 1950s, and it was found that it has estrogen activity. Soy isoflavones are a type of isoflavone phytoestrogens. The structures of genistein and datuflavin in soy isoflavones are similar to the active groups of mammalian estrogen, i.e., diphenolic hydroxyl groups. Soy isoflavones have a bidirectional regulatory effect on the human body, both as estrogen and anti-estrogen. At low doses, it can competitively bind to estrogen receptors, reduce estrogen activity, and produce anti-estrogen function; at medium doses, soy isoflavones produce estrogen effects; at high doses, they produce estrogen-enhancing effects; but the estrogen activity of soy isoflavones is one thousandth to one hundred thousandth of the activity of endogenous estrogen, and has weak estrogen activity. Soy isoflavones can improve women's menopausal syndrome because it has the active effect of estrogen. The human body can supplement soy isoflavones to make up for the reduced secretion of estrogen due to menopause, thereby alleviating or avoiding menopausal discomfort and osteoporosis symptoms caused by the decrease in estrogen secretion levels. In addition, soy isoflavones prevent the proliferation of cancer cells related to estrogen secretion, and have a certain preventive and therapeutic effect, such as uterine cancer, prostate cancer and other diseases. It is also a natural antioxidant that can form a free intermediate to block free radical reactions. The in vitro simulated biological reaction experiment confirmed that soy isoflavones have strong antioxidant capacity and are also excellent free radical scavengers. Due to its antioxidant effect, soy isoflavones also play a certain role in treating or preventing diseases caused by lipid peroxidation in the human body, such as atherosclerosis, coronary heart disease, hyperlipidemia and other diseases.
As an important organ of the human body, the skin's protective and non-permeable properties can protect the body from the loss of water, minerals and dissolved proteins, as well as the damage of harmful substances from the outside world. The skin needs nutritional support like other organs. In addition to providing nutrition through food, it can also provide nutrition through external transdermal diffusion, and minimize the side effects of active substances. Since the composition structure of liposomes is similar to that of biological membranes, they have better compatibility with the skin, can enhance the permeability of active substances in the stratum corneum and have low irritation. Its water retention effect on the stratum corneum enhances hydration and makes the skin softer and smoother. This feature of both the safety of cosmetics and the functionality of active substances makes liposomes more widely used in cosmetics. Soy isoflavones are a natural antioxidant that can form a free and intermediate to block free radical reactions. It has strong antioxidant capacity and is also an excellent free radical scavenger. Therefore, it has great application potential in the field of cosmetics. However, due to the poor solubility and low solubility of soy isoflavones, which are neither hydrophilic nor lipophilic, its application in cosmetics is limited. To this end, researchers encapsulated soy isoflavones in liposomes to form nanoliposome soy isoflavones. After soy isoflavones were embedded in liposomes, compared with unencapsulated soy isoflavones, they had better transdermal diffusion, penetration and sustained release effects, and their stability was also significantly improved.
Alternate Names:
Liposomal soy isoflavone
Nanoencapsulated soy isoflavone
Liposome-encapsulated soy isoflavone
Soy isoflavone liposomes
References:
1. Sohn SI, et al.; Metabolic Engineering of Isoflavones: An Updated Overview. Front Plant Sci. 2021, 12:670103.
Articulating the Pharmacological and Nanotechnological Aspects of Genistein: Current and Future Prospectives
Curr Pharm Biotechnol
Authors: Bansal K, Singh V, Mishra S, Bajpai M.
Abstract
Throughout the past several centuries, herbal constituents have been the subject of scientific interest and the latest research into their therapeutic potential is underway. Genistein is a soy-derived isoflavone found in huge amounts in soy, along with the plants of the Fabaceae family. Scientific studies have demonstrated the beneficial effects of genistein on various health conditions. Genistein presents a broad range of pharmacological activities, including anticancer, neuroprotective, cardioprotective, antiulcer, anti-diabetic, wound healing, anti-bacterial, antiviral, skin, and radioprotective effects. However, the hydrophobic nature of genistein results in constrained absorption and restricts its therapeutic potential. In this review, the number of nanocarriers for genistein delivery has been explored, such as polymeric nanoparticles, nanostructured lipid carriers, solid lipid nanoparticles, liposomes, micelles, transferosomes, and nanoemulsions and nanofibers. These nano-formulations of genistein have been utilized as a potential strategy for various disorders, employing a variety of ex vivo, in vitro, and in vivo models and various administration routes. This review concluded that genistein is a potential therapeutic agent for treating various diseases, including cancer, neurodegenerative disorders, cardiovascular disorders, obesity, diabetes, ulcers, etc., when formulated in suitable nanocarriers.
Dietary Soy Isoflavone: A Mechanistic Insight
Nat Prod Commun.
Authors: Chadha R, Bhalla Y, Jain A, Chadha K, Karan M.
Abstract
Soy, a major component of the diet for centuries contains the largest concentration of isoflavones, a class of phytoestrogens. A variety of health benefits are associated with the consumption of soy primarily because of the isoflavones genistein, daidzein, and glycitein with a potential protective effect against a number of chronic diseases. Owing to the pharmaceutical and nutraceutical properties allied with isoflavonoids and their use in functional foods, there is a growing interest in these compounds. This review throws light on the chemistry, and significant pharmacological and biopharmaceutical aspects of soy isoflavones. This article critically describes the mechanisms of action, infers conclusions and shows opportunity for future research.
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