P-Carotene Vitamin

ATBC (Albanes etal., 1996) 29133 male smokers 20 mg P-carotene + vitamin A 17.5 Increase Increase... 

MPTP decreases glutathione levels and increases the levels of reactive oxygen species and the degree of lipid peroxidation in mouse brain slices in vitro and increases the levels of reactive oxygen species in mouse brain in vivo. MPTP neurotoxicity in vitro is reduced by glutathione. In vitro studies have shown that MPP neurotoxicity can be reduced by vitamin E, vitamin C, coenzyme Q, and mannitol (but not by superoxide dismutase, catalase, allopurinol, or dimethyl sulfoxide). P-Carotene, vitamin C, and /V-acctylcystcine partially protect against the neurotoxic effects of MPTP in mice, as do nicotinamide, coenzyme Q, and the free-radical spin trap A-tert-butyl-a-(sulfophenyl) nitrone. 

This unsaturated ketone is an important industrial precursor to p-carotene, vitamin A, and other similar molecules. Disconnection using the carbonyl group gives a synthon for which a good reagent will be acetoacetate. 

The Supplementation Vitamin, Minerals and Antioxidant Trial (SU. VI.M.AX) is testing, in 15,000 healthy French men and women, whether a combination of antioxidant vitamins and minerals, including vitamin E, p-carotene, vitamin C, selenium, and zinc, protects against CHD. In the United States, an intervention trial was started with 8000 women with recent CHD in order to test in a factorial design the effect of P-carotene, vitamin E, and vitamin C. 

Com Insect resistance (cry34Abl and cry35Abl) and herbicide tolerance (glufosinate, pat) Pr, Fi, M,AA, FA, p-carotene, vitamins B, B, folic ac. tocopherols, femlic ac., p-coumaric ac., inositol, raffinose, phytic ac., TI Herman et al. (2007)... 

More recently, another derivative of sinapic acid has been identified because of its highly potent antioxidant activity and the antimutagenic and anticarcino-genic properties (Kuwahara et al., 2004 Vuorela et al., 2005 Cao et al., 2008). This derivative, 2,6-dimethoxy-4-vinylphenol (vinylsyringol) or canolol, was first identified in two independent studies by Koski et al. (2003) and Wakamatsu et al. (2005) in crude canola oil. Kuwahara et al. (2004) described the antimutagenic potency of this compound as higher than a-tocopherol, P-carotene, vitamin C... 

Abalde, J., Fabregas, J., Herrero, C., 1991. p-Carotene, vitamin C and vitamin E content of the marine microalga Dunaliella tertiolecta cultured with different nitrogen sources. Bioresource Technology 38 (2), 121-125. 

Two molecules of vitamin A are formed from one molecule of -carotene. Vitamin A crystallizes in pale yellow needles m.p. 64 C. It is optically inactive. It is unstable in solution when heated in air, but comparatively stable without aeration. Vitamin A is manufactured by extraction from fish-liver oils and by synthesis from / -ionone. The role of vitamin A in vision seems to be different from its systemic function. See also relincne and rhodopsin. 

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... 

Solvent extraction removes chlorophyll and other pigments to give a light-colored product but increases processing costs. Furthermore, solvent extraction removes p-carotene and reduces vitamin A activity (89) (see Terpenoids Vitamins). Supercritical CO2 extraction at 30 and 70 MPa (4,350 and 10,150 psi) and 40°C removed 90 and 70% carotene and lutein, respectively, from alfalfa LPC (96). This process avoids organic solvent residues and recovers valuable by-products. 

An important function of certain carotenoids is their provitamin A activity. Vitamin A may be considered as having the stmcture of half of the P-carotene molecule with a molecule of water added at the end position. In general, all carotenoids containing a single unsubstituted P carotene half have provitamin A activity, but only about half the activity of P carotene. Provitamin A compounds are converted to Vitamin A by an oxidative enzyme system present in the intestinal mucosa of animals and humans. This conversion apparendy does not occur in plants (see Vitamins, VITAMIN a). 

Vitamin A constitutes the most significant sector of the commercial retinoid market and is used primarily in the feed area. In the pharmaceutical area, there are several important therapeutic dermatologic agents which stmcturaHy resemble vitamin A and they are depicted in Figure 2 (see Pharmaceuticals). The carotenoids as provitamin A compounds also represent an important commercial class of compounds with P-carotene [7235-40-7] (10) occupying the central role (Fig. 3) (9). 

In the BASF synthesis, a Wittig reaction between two moles of phosphonium salt (vitamin A intermediate (24)) and C q dialdehyde (48) is the important synthetic step (9,28,29). Thermal isomerization affords all /ra/ j -P-carotene (Fig. 11). In an alternative preparation by Roche, vitamin A process streams can be used and in this scheme, retinol is carefully oxidized to retinal, and a second portion is converted to the C2Q phosphonium salt (49). These two halves are united using standard Wittig chemistry (8) (Fig. 12). 

In nature, vitamin A aldehyde is produced by the oxidative cleavage of P-carotene by 15,15 - P-carotene dioxygenase. Alternatively, retinal is produced by oxidative cleavage of P-carotene to P-apo-S -carotenal followed by cleavage at the 15,15 -double bond to vitamin A aldehyde (47). Carotenoid biosynthesis and fermentation have been extensively studied both ia academic as well as ia iadustrial laboratories. On the commercial side, the focus of these iavestigations has been to iacrease fermentation titers by both classical and recombinant means. 

Animals cannot synthesize vitamin A-active compounds and necessary quantities are obtained by ingestion of vitamin A or by consumption of appropriate provitamin A compounds such as P-carotene. Carotenoids are manufactured exclusively by plants and photosynthetic bacteria. Until the discovery of vitamin A in the purple bacterium Halobacterium halobium in the 1970s, vitamin A was thought to be confined to only the animal kingdom (56). Table 4 Hsts RDA and U.S. RDA for vitamin A (67). 

Canthaxanthin crystallines from various solvents as brownish violet, shiny leaves that melt with decomposition at 210°C. As is the case with carotenoids in general, the crystals are sensitive to light and oxygen and, when heated in solution or exposed to ultraviolet light or iodine, form a mixture of cis and trans stereoisomers. Consequentiy, crystalline canthaxanthin should be stored under inert gas at low temperatures. Unlike the carotenoid colorants P-carotene and P-apo-8 -carotenal, canthaxanthin has no vitamin A activity. It is chemically stable at pH 2—8 (the range normally encountered in foods) and unaffected by heat in systems with a minimal oxygen content. 

Figure 45-1. P-Carotene and the major vitamin A vitamers. Shows the site of cleavage of P-carotene into two molecules of retinaldehyde by carotene dioxygenase.

Vitamin A (retinol), present in carnivorous diets, and the provitamin (P-carotene), found in plants, form retinaldehyde, utilized in vision, and retinoic acid, which acts in the control of gene expression. Vitamin D is a steroid prohormone yielding the active hormone derivative calcitriol, which regulates calcium and phosphate metaboUsm. Vitamin D deficiency leads to rickets and osteomalacia. 

The a-tocopherol, P-carotene (ATBC) Cancer Prevention study was a randomised-controlled trial that tested the effects of daily doses of either 50 mg (50 lU) vitamin E (all-racemic a-tocopherol acetate), or 20 mg of P-carotene, or both with that of a placebo, in a population of more than 29,000 male smokers for 5-8 years. No reduction in lung cancer or major coronary events was observed with any of the treatments. What was more startling was the unexpected increases in risk of death from lung cancer and ischemic heart disease with P-carotene supplementation (ATBC Cancer Prevention Study Group, 1994). Increases in the risk of both lung cancer and cardiovascular disease mortality were also observed in the P-carotene and Retinol Efficacy Trial (CARET), which tested the effects of combined treatment with 30 mg/d P-carotene and retinyl pahnitate (25,000 lU/d) in 18,000 men and women with a history of cigarette smoking or occupational exposure to asbestos (Hennekens et al, 1996). 

Most carotenoids have no pro-vitamin A activity with the notable exceptions of P-carotene, and to a lesser extent a-carotene and P-cryptoxanthin. They act as macular pigments (lutein and zeaxanthin) and they have antioxidant and biochemical properties other than pro-vitamin A activity. 

---