Cacao seeds

C7H9N402- M.p. 337 C, an alkaloid obtained from cacao seeds or prepared synthetically. Constitutionally it is similar to caffeine, and is also a weak base. It is usually administered as the sodium compound combined with either sodium ethanoate or sodium salicylate, and is employed almost entirely as a diuretic. Physiologically theobromine resembles caffeine, but its effect on the central nervous system is less, while its action on the kidneys, is more pronounced. 

Acetic acid occurs naturally in many plant species including Merrill flowers Telosma cordata), in which it was detected at a concentration of 2,610 ppm (Furukawa et al., 1993). In addition, acetic acid was detected in cacao seeds (1,520 to 7,100 ppm), celery, blackwood, blueberry juice (0.7 ppm), pineapples, licorice roots (2 ppm), grapes (1,500 to 2,000 ppm), onion bulbs, oats, horse chestnuts, coriander, ginseng, hot peppers, linseed (3,105 to 3,853 ppm), ambrette, and chocolate vines (Duke, 1992). 

H.G.M. Edwards, S.E.J. Villar, L.E.C. de Oliveira and M. Le Hyaric, Analytical Raman spectroscopic study of cacao seeds and their chemical extracts. Anal. Chim. Acta, 538, 175-180 (2005). 

Different authors used RP-HPLC and UV detection to monitor peptide formation during cheese ripening [174-178], providing valuable information about proteolysis. When large hydrophobic peptide need to be separated an lEC represents the best choice [179]. Nevertheless, the identification of these peptides is essential for the complete understanding of the proteolytic process. The peptides eluted from the LC column can be subjected to ESl-MS for molecular weight determination and MS/MS for amino acid sequence determination, which allow rapid peptide identification [172]. HPLC-ESl-MS and MS/MS techniques have been successfully used for peptide mass fingerprint purposes for sequence analysis of purified albumin from Theobroma cacao seeds [180,181]. 

Caffeine (1.10), found in coffee (Coffea arabica), was introduced to Europe through Constantinople (modem Istanbul) in the 1500s (Figure 1.5). The stimulant effects of coffee were widely acknowledged, but coffee was recognized as a useful diuretic. Caffeine was first synthesized by Emil Fischer in 1882. Two related compounds, theobromine (1.11) and theophylline (1.12), found in cacao seeds (Theobroma cacao) and tea (Camellia sinensi), respectively, are more potent diuretics than caffeine.1 All three compounds are based on the purine ring system (1.13). 

Cocoa butter The yellow I sh-white fat of the cacao seed. 

Kenny TP, Keen CL, Jones P, Kimg HJ, Schmitz HH, Gershwin ME (2004) Pentameric procyanidins isolated from Theobroma cacao seeds selectively downregulate ErbB2 in human aortic endothelial cells. Exp Biol Med (Maywood) 229 255-263... 

Wong, M.K., Dimick, P.S., and Hammerstedt, R.H. Extraction and high performance liquid chromatographic enrichment of polyphenoloxidase from theobroma cacao seeds, J. Food Sci., 55,1108,1990. 

In roasted cocoa powders, 13 Cinnamic acid amides [48-50] have been quantified, which are also found in fresh seeds, but unfortunately there are no quantitative data for these amides in unprocessed fresh cacao seeds ... 

Raw cocoa seeds contain approximately 6.9—18 % proanthocyanidins of defatted dry weight [61, 62]. Porter et al. [63] described (2R,3S)-(+)-catechin, (2R, 3R)-( )-epicatechin, and the dimers epicatechin-(4(3 8)-catechin (procyanidin Bl, see above) procyanidin B, epicatechin-(4p 6)-epicatechin, and epicatechin-(4p 8)-epicatechin (procyanidin Cl) as the dominating compounds in cacao seeds [63]. Two glycosides 3-0-p-D galactopyranosyl-ent-epicatechin-(2a 7,4 a 8) epicatechin and 3-0-L-arabinopyranosyl ent-epicatechin-(2a 7, 4a 8)-epicatechin were found in addition to epicatechin-(2(i 5,4(3 6)-epicatechin [63,64]. 

Three main types of ingredients are produced from cacao seeds cocoa powder, cocoa butter, and cocoa extracts. For the manufacture of these products, the cacao beans are first cured by fermentation and drying, during... 

Triacylglycerols make up about 96% of mature cocoa (Theobroma cacao) seed lipid, more than half the seed dry weight, and thus are the major storage products of the seed. These storage products are a mixture of glycerol esters of oleic, palmitic, stearic, and much smaller amounts of llnolelc acid. The collection of esters is called cocoa butter, a solid fat, and, at more than 4 a pound, is the most expensive edible fat in the world. Annual world production of cocoa butter is more than 2 billion pounds. 

Laloi, M., McCarthy, J., Morandi, O., et al. (2002) Molecular and biochemical characterization of two aspartic protein-ases TcAPl and TcAP2 from Theobroma cacao seeds. Planta 215, 754-762. 

Cacao Theobroma cacao Seeds, cash crop... 

Two other commonly found sources of caffeine (16) are kola Cold) from the seeds of, for example. Cola nitida (Vent.) Schott and Engl., which contains 1—4% of the alkaloid, but Httie theophylline or theobromine, and cocoa (from the seeds of Theobroma cacao L.), which generally contains about 3% theobromine and significantiy less caffeine. 

The name Theobroma cacao, food of the gods, indicating both the legendary origin and the nourishing quaUties of chocolate, was bestowed upon the cacao tree by Linnaeus in 1720. All cocoa and chocolate products are derived from the cocoa bean, the seed of the fmit of this tree. Davila Garibi, a contemporary Mexican scholar, has traced the derivation of the word from basic root words of the Mayan language to its adoption as chocolate in Spanish ( ) ... 

The FDA has not legally defined cocoa butter, and no standard exists for this product under the U.S. Chocolate Standards. For the purpose of enforcement, the FDA defines cocoa butter as the edible fat obtained from cocoa beans either before or after roasting. Cocoa butter as defined in the US. Pharmacopeia is the fat obtained from the roasted seed of Theohroma cacao Uinne. 

Although low levels of methylxanthines have been detected in the leaves and flowers of T. cacao, the primary storage location is within the seed or bean.16 The cocoa bean is the major natural source of the methylxanthine theobromine, but contains only small amounts of caffeine. Theophylline has been detected in cacao beans, but at such low concentrations that its presence generally is ignored. Together, theobromine and caffeine account for up to 99% of the alkaloid content of T. cacao beans. Alkaloid content is affected by genetic makeup, maturity of beans at harvest, and fermentation process. Analytical methodology also is partially responsible for some of the disparity in methylxanthine values since many early methods were unable to separate theobromine and caffeine. 

In live cocoa seeds, the methylxanthines are localized in polyphenolic storage cells. Bean death, which occurs 24 to 48 h after initiation of fermentation, triggers diffusion of the methylxanthines from the nib to the shell. The early studies of Humphries state that cacao cotyledons lose about 40% of their theobromine during fermentation.17 According to Knapp and Wadsworth, the loss of theobromine and caffeine becomes significant on the third day when the methylxanthines begin to diffuse into the shell.18 This migration continues until the concentration of the methylxanthines in nibs and shell are almost equal. 

Arteel and Sies (1999) examined procyanidin oligomers of different size, isolated from the seeds of Theobroma cacao, for their ability to protect against nitration of tyrosine. Serraino and others (2003) investigated antioxidant activity of the blackberry juice and cyanidin-3-O-glucoside on endothelial dysfunction in cells and in vascular rings exposed to peroxynitrite. However, more work is needed in this area, and the confounding effects of oxidized protein/amino acids in the diet need to be elucidated. 

Some plants produce a mixture of fatty acids (Table 11.3). The fat in seeds of the cacao tree (Theobroma cacao) contains a mixture of stearic and palmitic acids. The fat is known as cocoa butter from its resemblance to the butter produced from cow s milk (see Box 11.2). 

Rigaud 1, Escribano-Bailon MT, Prieur C et al (1993) Normal phase high performance liquid chromatographic separation of procyanidins from cacao beans and grape seeds. 1 Chromatogr 654 255-260... 

Cocoa butter NF is defined as the fat obtained from the seed of Theobroma Cacao Linne (Family Sterculiaceae) (44). Cocoa butter softens at 30°C and melts at 34°C. It contains four different forms alpha, beta, beta prime, and gamma with melting points of 22°C, 34°C to 35°C, 28°C and 18°C, respectively. The beta form is the most stable and is desired for suppositories. The biggest challenge with the polymorphism of cocoa butter is the impact of the manufacturing process on the characteristics of the suppository itself. When cocoa butter is hastily melted at a temperature greatly exceeding the minimum required temperature and then quickly chilled, the result is metastable crystalline form (a crystals), which may not even... 

Pure chocolate is a mixture of torrefied, powdered cacao with sugar (saccharose) sometimes excess of fat is added and sometimes a small quantity of various essences or spices. Starch chocolate contains, in addition, one of a number of starches or flours (of rice, oats, chestnut, or of oily seeds such as walnut, arachis, etc.). Chocolate of lower quality sometimes contains powder cacao husks, and occasionally other sugars than saccharose (glucose) are added other adulterants are dextrin, gum and gelatine. Milk chocolate is prepared with cacao, sugar and milk powder or extract. 

Microscopic Examination.—A few grams of the chocolate are freed from fat by extraction with carbon tetrachloride and from sugar by washing on a filter with a little alcohol and then with cold water. The residue, well mixed in a mortar, is examined with a magnification of 300-400 diameters, best in comparison with products of known origin. Such examination will show if the normal constituents of pure chocolate are accompanied by starch or flour of cereals, chestnuts (see Fig. 32 of Plate IV in the chapter on Flour) or oily seeds, or powdered cacao husks. 

Catechin and the proanthocyanidin prodelphinidin B3 are, respectively, the major monomeric and dimeric flavan-3-ols found in barley and malt where prodelphinidin B3 is the main contributor for the radical scavenging activity [Dvorakova et al., 2007], Proanthocyanidins have also been detected in nuts. Hazelnuts (Corylus avellana) and pecans (Carya illinoensis) are particularly rich in proanthocyanidins containing ca. 5 g kg, whereas almonds (Prunus dulcis) and pistachios (Pistachio vera) contain 1.8-2.4 mg kg 1, walnuts (Juglans spp.) ca. 0.67 g kg, roasted peanuts (Arachis hypgaea) 0.16 g kg, and cashews (Anarcardium occidentale) 0.09 g kg 1 [Crozier et al., 2006c]. Dark chocolate derived from the roasted seeds of cocoa (Theobroma cacao) is also a rich source of procyanidins [Gu et al., 2004], Monomeric flavan-3-ols and the proanthocyanidin B2, B5 dimers, and Q trimer are found in fresh cocoa beans (Fig. 1.13). Flavan-3-ols have also been detected in mint... 

Although cocoa as a drink is now rather unfashionable, it provides the raw material for the manufacture of chocolate and is commercially very important. Cocoa (or cacao) is derived from the roasted seeds of Theobroma cacao (Sterculiaceae), a tree widely cultivated in South America and West Africa. The fruits develop on the trunk of the tree, and the seeds from them are separated, allowed to ferment, and are then roasted to develop the characteristic chocolate flavour. The kernels are then separated from the husks, ground up, and processed in various ways to give chocolate, cocoa, and cocoa butter. 

One of the world s most popular flavors is determined by a physical-chemical composition which starts with the seeds of the plant, Theobroma cacao, and continues with an empirical process discovered and perfected by the Aztecs, or by an earlier society from whom the Aztecs received it. 

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