Phytosteroids and Related Compounds
Amritpal Singh Saroya in Contemporary Phytomedicines, 2017
Phytosterols, which encompass plant sterols and stanols, are steroid compounds similar to cholesterol, which occur in plants and vary only in carbon side chains and/or in the presence or absence of a double bond.Sterols are a family of molecules with a specific shape and structure. Phytosterols are sterols found in plants. The sterols found in animals are called zoosterols and the best-known of these is cholesterol. Stanol ester is a heterogeneous group of chemical compounds known to reduce the level of low-density lipoprotein (LDL) cholesterol in blood when ingested, though to a much lesser degree than prescription drugs such as statins. The starting material is phytosterols from plants.
Macronutrients
Chuong Pham-Huy, Bruno Pham Huy in Food and Lifestyle in Health and Disease, 2022
Sterols are lipid compounds containing a phenanthrene skeleton, and have 27–30 carbon atoms with a hydroxy group (alcohol) at C-3 of the first ring of phenanthrene structure and a side chain of at least seven carbons at C-17. Sterols are quite different from triglycerides and phospholipids made up of fatty acids. Sterols are abundant in nature: animals, plants and fungi (mushrooms) and comprise over 300 compounds (69, 118–119). According to their source, sterols are divided into three groups: zoosterols derived from animals, phytosterols or plant sterols, and mycosterols present in fungi. The most important animal sterol is cholesterol, while phytosterols are abundant in plants. Ergosterol is a common mycosterol found in cell membranes of fungi, yeast and protozoa. Cholesterol in humans and animals is precursor of steroid hormones, vitamin D3 and bile salts. Sterols (cholesterol, phytosterol, mycosterol) play an important role as structural components of cell membranes, and have a broad range of biological activities and physical properties (69, 118–119).
Fats, Fatty Acids, and Lipids
Luke R. Bucci in Nutrition Applied to Injury Rehabilitation and Sports Medicine, 2020
Phospholipids are similar to triglycerides, but one end carbon of the glycerol backbone has a phosphate group instead of a fatty acid (phosphatide). The phosphate group is usually bound to one of the following: choline, ethanolamine, serine, or inositol to form a phospholipid. Sterols are hydrocarbon ring structures with varying amounts of unsaturation. Steroids (polyunsaturated sterols) have rigid, planar structures. Many modifications of sterols and steroids are encountered, with esterification, hydroxylation, oxidation, and conjugation being more frequently observed. Common sterols and steroids are cholesterol, p-sitosterol, bile acids, estrogens, progestins, testosterones, corticosteroids, and mineralosteroids. Dolichols are long-chain alcohols used in carbohydrate transport and metabolism in cells. Quinones are exemplified by coenzyme Q10, an extremely important link in the conversion of foodstuffs into cellular energy. Quinones possess substituted rings, usually with hydrocarbon side chains, and are present inside of cell organelle membranes.
Functional Food and Cardiovascular Disease Prevention and Treatment: A Review
Published in Journal of the American College of Nutrition, 2018
Sedigheh Asgary, Ali Rastqar, Mahtab Keshvari
Sterols are compounds associated with variable proportion of lipids, between 0.2% and 2%. Their basic structure is the cyclopentanophenanthrene condensed 4-cycle system. Sterols are compounds that can be free or esterified with fatty acids, mainly saturated fatty acids. There is a large amount of experimental evidence that demonstrated that the plant sterols have an important hypocholesterolemic effect, reducing both the concentrations of total cholesterol and LDL-C. The most studied effect of plant sterols is their inhibition of intestinal absorption of cholesterol. Plant sterols are more hydrophobic than cholesterol; thus, they can competitively reduce the absorption of micellar cholesterol. In addition, the plant sterols can reduce the rate of cholesterol esterification in the enterocyte (affecting the activity of acyl coenzyme A [CoA]:cholesterol acyltransferase), thus reducing the amount of cholesterol exported into the blood in the chylomicrons formed. The inhibition of cholesterol absorption produces an increase in the synthesis of LDL receptor, which increases the elimination of LDL and also the IDL from the circulation, and given that these are the precursors of LDL-C, this decreases in addition its production without affecting triacylglyceride and HDL-C concentrations. There are no conclusive data regarding the effect of plant sterols on the bile metabolism, although some studies suggest that they produce an increase in the excretion of bile acids, whereas other studies suggest that there is no effect (243,246).
Chemical composition, anti-toxoplasma, cytotoxicity, antioxidant, and anti-inflammatory potentials of Cola gigantea seed oil
Published in Pharmaceutical Biology, 2019
O. Atolani, H. Oguntoye, E. T. Areh, O. S. Adeyemi, L. Kambizi
The chemical constituent of C. gigantea seed has been investigated. The GC-MS analysis revealed the presence of 12 fatty acids of which palmitic and stearolic acids were the dominant fatty acids. Four sterols, namely cholesterol, campesterol, stigmasterol, and β-sitosterol were detected and quantified. Our data showed that the C. gigantea oil extract possesses mild antioxidant as well as an anti-inflammatory potential. Further, data suggest that the anti-parasite action of the C. gigantea oil extract might be as a result of general cellular toxicity and that this toxic effect precludes ROS production and/or oxidative stress. Overall, data shows the bio-activity potential of the oil from the underutilized seed has significant capacity for application in foods and cosmetics. The potential in the seed could be cheaply harnessed for future chemical and biochemical applications.
Cancer prevention and treatment using combination therapy with natural compounds
Published in Expert Review of Clinical Pharmacology, 2020
Terpenoids, also know as isoprenoids, are the largest group of natural compounds that play a variety of roles in many plants. Both steroids and sterols are triterpenoids. All terpenoids are synthesized from two five carbon building blocks, includingmonoterpenes (C10), sequiterpenes (C15), diterpenes (C20), sesterterpenes (C25), triterpenes (C30), tetraterpenes (C40) and polyterpenes [66]. Triterpenoids are found in seaweed, in the wax-like coating of fruits such as apples, cranberries and figs, and in a variety of medicinal herbs [66]. Triterpenoids are synthesized in plants by the cyclization of squalene [67]. The antitumor efficacy of plant derived triterpenoids has been demonstrated in animal models of melanoma [68]. In addition to triterpenoids found in nature, triterpenoids have been synthesized by structural modification of natural compounds to optimize bioactivity. Some of the synthetic compounds appear to have potent anti-inflammatory and anticarcinogenic properties [69]. The triterpenoid oleanolic acid is a medicinal herb that reportedly has hepatoprotective effects when administered at low doses, but high doses can cause cholestasis and hepatotoxicity [70]. Several hundred synthetic triterpenoids based on oleanolic acid have been synthesized, some with potent antiinflammatory and antiproliferative effects [66].
Related Knowledge Centers
- Alcohol
- Animal
- Bacteria
- Functional Group
- Organic Compound
- Steroid
- Gonane
- Hydrogen
- Hydroxy Group
- Cholesterol