Content of green Arabica coffee seedsThe term “green coffee seed” refers to unroasted mature or immature coffee seeds. These have been processed by wet or dry methods for removing the outer pulp and mucilage, and have an intact wax layer on the outer surface. When immature, they are green. When mature, they have a brown to yellow or reddish color, and typically weigh 300 to 330 mg per dried coffee seed. Nonvolatile and volatile compounds in green coffee seeds, such as caffeine, deter many insects and animals from eating them. Further, both nonvolatile and volatile compounds contribute to the flavor of the coffee seed when it is roasted. Nonvolatile nitrogenous compounds (including alkaloids, trigonelline, proteins and free amino acids) and carbohydrates are of major importance in producing the full aroma of roasted coffee, and for its biological action. Since the mid 2000s green coffee extract has been sold as a nutritional supplement, and has been clinically studied for its chlorogenic acid content and for its lipolytic and weight-loss properties.
Nonvolatile alkaloidsImmature Coffea canephora berries on a tree in Goa, India. Caffeine (1,3,7-trimethyl-xanthine) is the alkaloid most present in green and roasted coffee seeds. The content of caffeine is between 1.0% and 2.5% by weight of dry green coffee seeds. The content of caffeine does not change during maturation of green coffee seeds. Lower concentrations oftheophylline, theobromine, paraxanthine, liberine, and methylliberine can be found. The concentration of theophylline, an alkaloid noted for its presence in green tea, is reduced during the roasting process, usually about 15 minutes at 230 °C (446 °F), whereas the concentration of most other alkaloids are not changed. The solubility of caffeine in water increases with temperature and with the addition of chlorogenic acids, citric acid, or tartaric acid, all of which are present in green coffee seeds. For example, 1 g (0.035 oz) caffeine dissolves in 46 ml (1.6 US fl oz) of water at room temperature, and 5.5 ml (0.19 US fl oz) at 80 °C (176 °F). The xanthine alkaloids are odorless, but have a bitter taste in water, which is masked by organic acids present in green coffee, however. Trigonelline (N-methyl-nicotinate) is a derivative of vitamin B6 that is not as bitter as caffeine. In green coffee seeds, the content is between 0.6% and 1.0%. At a roasting temperature of 230 °C (446 °F), 85% of the trigonelline is degraded to nicotinic acid, leaving small amounts of the unchanged molecule in the roasted seeds. In green coffee seeds, trigonelline is synthesized from nicotinic acid (pyridinium-3-carboxylic acid) by methylation from methionine, a sulfur-containing amino acid. Mutagenic activity of trigonelline has been reported.
Proteins and amino acidsProteins account for 8% to 12% of dried green coffee seeds. A majority of the proteins are of the of 11-S-storage kind  (alpha – component of 32 kDa, beta – component of 22 kDa), most of which are degraded to free amino acids during maturation of green coffee seeds. Further, 11-S-storage proteins are degraded to their individual amino acids under roasting temperature and are thus an additional source of bitter components due to generation of Maillard reaction products. High temperature, oxygen concentration and low pH degrade 11-S-storage proteins of green coffee seeds to low molecular weight peptides and amino acids. The degradation is accelerated in the presence of organic acids such as chlorogenic acids and their derivatives. Other proteins include enzymes, such as catalase and polyphenol oxidase, which are important for the maturation of green coffee seeds. Mature coffee contains free amino acids (4.0 mg amino acid/g robusta coffee and up to 4.5 mg amino acid/g arabica coffee). In Coffea arabica, alanine is the amino acid with the highest concentration, i.e. 1.2 mg/g, followed by asparagine of 0.66 mg/g, whereas in C. robusta, alanine is present at a concentration of 0.8 mg/g and asparagine at 0.36 mg/g. The free hydrophobic amino acids in fresh green coffee seeds contribute to the unpleasant taste, making it impossible to prepare a desirable beverage with such compounds. In fresh green coffee from Peru, these concentrations have been determined as follows: isoleucine 81 mg/kg, leucine100 mg/kg, valine 93 mg/kg, tyrosine 81 mg/kg, phenylalanine 133 mg/kg. The concentration of gamma-aminobutyric acid (a neurotransmitter) has been determined between 143 mg/kg and 703 mg/kg in green coffee seeds from Tanzania. Roasted coffee seeds do not contain any free amino acids, the amino acids in green coffee seeds are degraded under roasting temperature to Maillard products (reaction products between the aldehyde group of sugar and the alpha-amino-group of the amino acids). Further, diketopiperazines, e.g. cyclo(proline-proline), cyclo(proline-leucine), and cyclo(proline-isoleucine), are generated from the corresponding amino acids, and are the major source of the bitter taste of roasted coffee. The bitter flavor of diketopiperazines is perceptible at around 20 mg/liter of water. The content of diketopiperazines in espresso is about 20 mg to 30 mg, which is responsible for its bitterness.
CarbohydratesCarbohydrates make up about 50% of the dry weight of green coffee seeds. The carbohydrate fraction of green coffee is dominated bypolysaccharides, such as arabinogalactan, galactomannan and cellulose, contributing to the tasteless flavor of green coffee. Arabinogalactan makes up to 17% of dry weight of green coffee seeds, with a molecular weight of 90 kDa to 200 kDa. It is composed of beta-1-3-linkedgalactan main chains, with frequent members of arabinose (pentose) and galactose (hexose) residues at the side chains comprising immunomodulating properties by stimulating the cellular defense system (Th-1 response) of the body. Mature brown to yellow coffee seeds contain fewer residues of galactose and arabinose at the side chain of the polysaccharides, making the green coffee seed more resistant to physical breakdown and less soluble in water. The molecular weight of the arabiniogalactan in coffee is higher than in most other plants, improving the cellular defense system of the digestive tract compared to arabinogalactan with lower molecular weight. Freemonosaccharides are present in mature brown to yellow-green coffee seeds. The free part of monosaccharides contains sucrose (gluco-fructose) up to 9000 mg/100g of arabica green coffee seed, a lower amount in robustas, i.e. 4500 mg/100g. In arabica green coffee seeds, the content of free glucose was 30 to 38 mg/100g, free fructose 23 to 30 mg/100g; free galactose 35 mg/100g and mannitol 50 mg/100g dried coffee seeds, respectively. Mannitol is a powerful scavenger for hydroxyl radicals, which are generated during the peroxidation of lipids in biological membranes.
LipidsThe lipids found in green coffee include: linoleic acid, palmitic acid, oleic acid, stearic acid, arachidic acid, diterpenes, triglycerides,unsaturated long-chain fatty acids, esters and amides. The total content of lipids in dried green coffee is between 11.7 g and 14 g / 100 g.Lipids are present on the surface and in the interior matrix of green coffee seeds. On the surface, they include derivatives of carboxylic acid-5-hydroxytryptamides with an amide bond to fatty acids (unsaturated C6 to C24) making up to 3% of total lipid content or 1200 to 1400 microgram/g dried green coffee seed. Such compounds form a wax-like cover on the surface of the coffee seed (200 to 300 mg lipids/100 g dried green coffee seeds) protecting the interior matrix against oxidation and insects. Further, such molecules have antioxidative activity due to their chemical structure. Lipids of the interior tissue are triglycerides, linoleic acid (46% of total free lipids), palmitic acid (30% to 35% of total free lipids), and esters. Arabica seeds have a higher content of lipids (13.5 to 17.4 g lipids/100 g dried green coffee seeds) than robustas (9.8 to 10.7 g lipids/100 g dried green coffee seeds). The content of diterpenes is about 20% of the lipid fraction. The diterpenes found in green coffee include cafestol, kahweol, 16-O-methylcafestol, cafestal and kahweal. Some of these diterpenes have been shown in in vitroexperiments to protect liver tissue against chemical oxidation. In coffee oil from green coffee seeds the diterpenes are esterified with saturated long chain fatty acids.
Nonvolatile chlorogenic acidsChlorogenic acids belong to a group of compounds known as phenolic acids, which are antioxidants. The content of chlorogenic acids in dried green coffee seeds of arabica 140 mg/g, depending on the timing of harvesting. At roasting temperature, more than 70% of chlorogenic acids are destroyed, leaving a residue of less than 30 mg/g in the roasted coffee seed. In contrast to green coffee, green tea contains an average of 85 mg/g polyphenols. These chlorogenic acids could be a valuable, inexpensive source of antioxidants. Chlorogenic acids are homologous compounds comprising caffeic acid, ferulic acid and 3,4-dimethoxycinnamic acid, which are connected by an ester bond to the hydroxyl groups of quinic acid. The antioxidant capacity of chlorogenic acid is more potent than of ascorbic acid (vitamin C) or mannitol, which is a selective hydroxy-radical scavenger. Chlorogenic acids have a bitter taste in low concentrations such as 50 mg/L water. At higher concentrations of 1 g/L water, they have a sour taste. Chlorogenic acids increase the solubility of caffeine and are important modulators of taste.
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