Nicotinic acid sources

P-Picoline may serve as an important source of nicotinic acid [59-67-6] for dietary supplements. A variety of substituted pyridines may be prepared from acrolein (75—83). 

Pyridine carboxamide [98-92-0] (nicotinamide) (1) and 3-pyridine carboxylic acid [59-67-6] (nicotinic acid) (2) have a rich history and their early significance stems not from their importance as a vitamin but rather as products derived from the oxidation of nicotine. In 1867, Huber prepared nicotinic acid from the potassium dichromate oxidation of nicotine. Many years later, Engler prepared nicotinamide. Workers at the turn of the twentieth century isolated nicotinic acid from several natural sources. In 1894, Su2uki isolated nicotinic acid from rice bran, and in 1912 Funk isolated the same substance from yeast (1). 

Hirschberg R, JC Ensign (1971a) Oxidation of nicotinic acid by a Bacillus species source of oxygen atoms for hydroxylation of nicotinic acid and 6-hydroxynicotinic acid. J Bacterial 108 757-759. 

Another selenium-containing molybdenum hydroxylase that has been isolated from Clostridium barkeri (identical to Eubacterium barkeri) is nicotinic acid hydroxylase (NAH). Clostridium barkeri was isolated initially as a fermentor of nicotinic acid and thus NAH is a key enzyme in the efficient fermentation of nicotinic acid as a source of carbon and energy. NAH contained selenium when purified from cells labeled with Se-selenite. However, this label was lost during denaturing gel electrophoresis and also on heating of the enzyme (Dilworth 1982). Exhaustive analysis of selenium-labeled alkylation products of NAH under various conditions revealed selenium was bound as a labile cofactor (Dilworth 1982), and not as seleno-cysteine. This report was the first to describe a selenium-dependent enzyme that did not contain selenium in the form of selenocysteine. 

Nicotinic acid decreases formation and secretion of VLDL by the liver (mechanism III in Fig. 23.2). This action appears secondary to its ability to inhibit fatty acid mobilization from adipose tissue. Circulating free fatty acids provide the main source of fatty acids for hepatic... 

Wehmeyer et al. (1969) published results on the content of B vitamins (thiamine, riboflavin, and nicotinic acid), vitamin C, and p-carotene and foimd that the morama bean is a good source of both B vitamins and vitamin C, but a poor source of p-carotene. Holse et al. (2010) investigated the content of the eight vitamin E isomers and found that the vitamin E composition in morama beans is dominated by y-tocopherol with 59-234 ng/g, followed by a- and p-tocopherols with 14- 8 gg/g and 1.1-3.3 ng/g, respectively. Eurthermore, traces of 8-tocopherol as well as p- and y-tocotrienols were present in some samples. The remaining two tocotrienols (a- and 8-) were not present in the beans. The presence of a-, p-, and y-tocopherols in the morama bean was also foimd by Mitei et al. (2009) who examined morama oil and by Dubois et al. (1995) who examined two samples of T.fassoglense. 

Potatoes are an excellent source of carbohydrates and contain significant amounts ofphosphorus, potassium, calcium, and vitamins, especially vitamin C. Potato protein content, at over 10%, is relatively close to that of wheat flour (11%) also, thanks to their lysine, methionine, cystine and cysteine contents, potatoes are a valuable supplement to cereal proteins. For instance, potatoes provide a significant source of proteins (10-15% of total requirements), a major source of vitamin C, an important source of energy, and also minerals like iron and other vitamins such as thiamin, nicotinic acid, riboflavin, and pro-vitamin A (p carotene) (Salunkhe and Kadam, 1991). 

SYNTHESIS There have been three total syntheses of ibogaine reported in the chemical literature. The first of these was a thirteen step process published about 30 years ago. Although the chemistry lab can serve a fine function for both isolation and purification of ibogaine from plant sources. In other words, there is no practical way to start from a bottle of nicotinic acid and actually prepare useful amounts. The parent ring system contains two chiral centers, neither of which is amenable to easy manipulation. 

In general, niacin is widespread in foodstuffs (93,94). Cereals, seeds, meat, and fish are good food sources of niacin. The niacin content of coffee beans is primarily a product of the roasting process, which converts trigonelline (1-methylnicotinic acid) to nicotinic acid (95). 

Carbohydrate metabolism provides the main energy source in coccidia. Diets deficient in thiamin, riboflavin, or nicotinic acid—all cofactors in carbohydrate metabolism—result in suppression of parasitic infestation of chickens by E tenella and E acervulina. A thiamin analog, amprolium—1-[(4-amino-2-propyl-5-pyrimidinyl)-methyl]-2-picolinium chloride—has long been used as an effective anticoccidial agent in chickens and cattle with relatively low host toxicity. The antiparasitic activity of amprolium is reversible by thiamin and is recognized to involve inhibition of thiamin transport in the parasite. Unfortunately, amprolium has a rather narrow spectrum of antiparasitic activity it has poor activity against toxoplasmosis, a closely related parasitic infection. 

O-tethered P-keto esters, through the intermediacy of aiylidene keto esters, have been efficiently utilized for the construction of immobilized dihydropyridines. Ceric ammonium nitrate (CAN) oxidation to pyridines followed by acidolytic cleavage provides a facile entry into nicotinic acid derivatives 57 [42], A three-component Biginelli cyclization of ureas on resin with a solution mixture of aldehydes and P-keto esters provides dihydropyrimidines 58 in high yield and purity [43], Heterocycles such as dihydropyridines and pyrimidines have historically proven to be a rich source of antimicrobial, antitumor, antiviral, and cardiovascular agents. 

The first committed step in TA and nicotine biosynthesis is catalyzed by putrescine JV-methyltransferase (PMT) (Fig.7.4).82 A PMT cDNA isolated from tobacco showed extensive homology to spermidine synthase from mammalian and bacterial sources.83 A-Methylputrescine is oxidatively deaminated to 4-aminobutanal, which undergoes spontaneous cyclization to form the reactive A-methyl-A1-pyrrolinium cation. Although the enzymes involved are unknown, the A-methyl-A1-pyrrolinium cation is thought to condense either with acetoacetic acid to yield hygrine as a precursor to the tropane ring, or with nicotinic acid to form nicotine. 

Sources Shrimpton, 1997 Institute of Medicine, 1997, 1998, 2000, 2001 Scientific Committee for Food, 1993 where two figures are shown for vitamin A, the lower is for women and the higher is for men (Table 2.5). for niacin and nicotinic acid, the lower values are for sustained reiease preparations the EU upper level of 25 mg of vitamin Be was proposed by the Scientific Committee for Food Opinion, 2000 and the EU upper level of 200 xg of vitamin B12 was set because of the possible presence of inactive corrinoids in pharmaceutical preparations, not because of toxicity of the vitamin itself. 

NAD is the source of ADP-ribose for the modification of proteins by mono-ADP-ribosylation, catalyzed by ADP-ribosyltransferases (Section 8.4.2), and poly(ADP-ribosylation), catalyzed by poly(ADP-ribose) polymerase (Section 8.4.3). It is also the precursor of two second messengers that act to increase the intracellular concentration of calcium, cADP-ribose, and nicotinic acid adenine dinucleotide phosphate (Section 8.4.4). 

The vitamin niacin (nicotinic acid, C6H5N02) can be isolated from a variety of natural sources such as liver, yeast, milk, and whole grain. It also can be synthesized from commercially available materials. From a nutritional point of view, which source of nicotinic acid is best for use in a multivitamin tablet Why ... 

The energy content of sunflower meal compares favorably with that of other oilseed meals and increases as the residual oil content increases and as the fiber content decreases. Sunflower meal also compares favorably with other oilseed meals as a source of calcium and phosphorus (36) and is an excellent source of water-soluble B-complex vitamins, namely nicotinic acid, thiamine, pantothenic acid, riboflavin, and biotin. 

Niacin (nicotinic acid and nicotinamide) is also known as vitamin B3. Both nicotinic acid and nicotinamide can serve as the dietary source of vitamin B3. 

Generous sources of this vitamin include pork. lamb, and beef livers hog kidneys yeasts pork beef tongue heans lean meats wheat germ peanut meal and green peas. Nicotinic acid can be synthesized by almost all planLs and animals. Tryptophan can be metabolized to a nicotinic acid nucleotide in animrds. but the efficiency of this mullistep process varies from species to species. Plants and many microorganisms synthesize this vitamin through alternative routes by use of aspartic acid. 

Nicotinamide-adenine dinucleotide (NAD diphosphopyri-dine nucleotide) and nicotinamide-adenine dinucleotide phosphate (NADP also termed triphosphopyridine nucleotide) represent most of the niacin activity found in good sources that include yeast, lean meats, liver, and poultry. Milk, canned salmon, and several leafy green vegetables contribute lesser amounts but are still sufficient to prevent deficiency. Additionally, some plant foodstuffs, especially cereals such as corn and wheat, contain niacin bound to various peptides and sugars in forms nutritionally not readily available (niacinogens or niacytin). Because tryptophan is a precursor of niacin, protein provides a considerable portion of niacin equivalent. As much as two thirds of niacin required by adults can be derived from tryptophan metaboHsm via nicotinic acid ribonucleotide... 

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