Retinol precursors

The known beneficial effects of retinoids on malignancies are assumed to relate to retinoid receptor-mediated antipromoting and anti-initiating effects. The latter appeals to be influenced by interference of several xenobiotics with different steps of the retinoid metabolism in the target cell. Of the carotenoids, (3-carotene is the most potent retinol precursor, yet being... 

Scheme 6.4). Various acetal alcohols, including a retinol precursor en route to vitamin A, were oxidized in very good to excellent yield on a scale up to 9 kg. Prior to product isolation, nitrogen was introduced to the reaction mixture to remove oxygen and avoid flammability of the organic layer during the aqueous workup. 

Carotenoids absorb visible light (Section 13 21) and dissipate its energy as heat thereby protecting the organism from any potentially harmful effects associated with sunlight induced photochemistry They are also indirectly involved m the chemistry of vision owing to the fact that p carotene is the biosynthetic precursor of vitamin A also known as retinol a key substance m the visual process... 

Biological, spectroscopic, and chromatographic methods have been used to assay vitamin A and the carotenoids. Biological methods have traditionally been based on the growth response of vitamin A—deficient rats. The utiUty and shortcomings of this test have been reviewed (52,53). This test has found apphcabiUty for analogues of retinol (54,55). Carotenoids that function as provitamin A precursors can also be assayed by this test (56). 

Other dietary factors implicated in prostate cancer include retinol, carotenoids, lycopene, and vitamin D consumption.5,6 Retinol, or vitamin A, intake, especially in men older than age 70, is correlated with an increased risk of prostate cancer, whereas intake of its precursor, [3-carotene, has a protective or neutral effect. Lycopene, obtained primarily from tomatoes, decreases the risk of prostate cancer in small cohort studies. The antioxidant vitamin E also may decrease the risk of prostate cancer. Men who developed prostate cancer in one cohort study had lower levels of l,25(OH)2-vitamin D than matched controls, although a prospective study did not support this.2 Clearly, dietary risk factors require further evaluation, but because fat and vitamins are modifiable risk factors, dietary intervention may be promising in prostate cancer prevention. 

In the body retinol can also be made from the vitamin precursor carotene. Vegetables like carrots, broccoli, spinach and sweet potatoes are rich sources of carotene. Conversion to retinol can take place in the intestine after which retinyl esters are formed by esterifying retinol to long chain fats. These are then absorbed into chylomicrons. Some of the absorbed vitamin A is transported by chylomicrons to extra-hepatic tissues but most goes to the liver where the vitamin is stored as retinyl palmitate in stellate cells. Vitamin A is released from the liver coupled to the retinol-binding protein in plasma. 

Vitamin A (retinol, 6.1) is the parent of a range of compounds known as retinoids, which possess the biological activity of vitamin A. In general, animal foods provide preformed vitamin A as retinyl esters (e.g. 6.5, which are easily hydrolysed in the gastrointestinal tract) while plant foods provide precursors of vitamin A, i.e. carotenoids. Only carotenoids with a /3-ionone ring (e.g. /1-carotene) can serve as vitamin A precursors. /3-Carotene (6.6)... 

Although chemically related, retinoic acid and retinol have distinctly different therapeutic applications. Retinol and its precursor are used as dietary supplements, whereas various forms of retinoic acid are useful in dermatology. 

Vitamin A Precursor to rhodopsin, a chemical used for vision assists in inhibiting bacterial and viral infections Night blindness (retinol)... 

Other antioxidant species are synthesized by cells like uric acid, ubiquinol or thiols (cystein, homocystein, etc.). In addition, many compounds found in food display antioxidant properties retinol (vitamin A) and its precursor /(-carotene, and polyphenols (flavonoids, etc.). Figure 8.2 shows the apparent standard potential of some LMWA and ROS explaining the spontaneous oxido-reduction reactions at the origin of the antioxidant protection system. 

Vitamin A or a precursor must be provided in the diet. This vitamin occurs in various forms (vitamers) retinol (alcohol), retinal (aldehyde), retinoic acid and vitamin A palmitate (ester). Requirements for vitamin A are usually expressed in international units (IU) per kg of diet. The international standards for... 

Rather surprisingly, the average person knows the names of several cofactors and coenzyme precursors, because many of these cannot be synthesized in vivo, and must be supplied in one s diet. This is the reason why a balanced diet should include retinol (vitamin A), ascorbic add (vitamin C), tocopherol (vitamin E), thiamine (vitamin Eh), folic acid etc., as well as zinc and iron. 

The first two of these roles appear to focus on the conformal chemistry associated with the external profile of the molecules. The latter role focuses on the internal, quantum-mechanical structure of the molecules. While retinol, in its metabolic role as a vitamin participates in the manufacture of components of the disks of the Outer Segment of the Photoreceptor cells, it primary role is the last one. It acts as the critical chromogen, independent of any vitamin or hormonal role, leading to the production of chromophores in the retinal pigment epithelium (RPE) cells of the eye. Morton noted this role specifically In the retina, retinol is indubitably a precursor. ... 

Vitamin A is found in nature and is available in several forms. Retinol (vitamin A) is an unsaturated alcohol containing an ionone ring and can be obtained from fish liver oil (Table 13-2), egg yolk, milk, and butter. Vitamin A2 (dehydroretinol) is present in freshwater fishes. /3-carotene, a carotenoid, is the most important precursor of this vitamin. 

Vitamin A, or retinol, is one of the major fat-soluble vitamins. It is present in many foods the best natural sources are liver, butter, margarine, egg yolk, carrots, spinach, and sweet potatoes. Vitamin A is the precursor of retinal, the essential component of the visual pigment rhodopsin. 

Carotenes are believed to be biological precursors of retinol, commonly known as vitamin A. If a molecule of /3-carotene is split in half at the tail-to-tail linkage, each of the diterpene fragments can be converted to retinol. 

Anhydroretinol may arise by nonenzymic isomerization of all-trans-retinol under acidic conditions and can act as a precursor for the synthesis of other biologically active retroretinoids (McBee et al., 2000). 

Nutritioncdly, on the basis of whether or not they have an unsubstituted /8-ionone ring and can therefore act as precursors of retinol (the provitcunin A cMotenoids)... 

Vitamin A has been widely studied in the field of cancer prevention, and studies have shown that smokers who consume more dietary vitamin A from foods have a lower risk for lung cancer (Mayne et al. 1998). Vitamin A is generally given as a dietary supplement in one of two forms, either as retinol (vitamin A) or as [3-carotene, a precursor which is converted by the body to vitamin A. An investigation focusing on dietary intake of vitamin A in asbestos workers (40 subjects) reported that subjects who had developed bronchial metaplasia reported a lower intake of dietary vitamin A than those without the condition (Mayne et al. 1998). 

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