Capsanthin esters

Goda et al. (1995) separated capsanthin esters from oleoresin of paprika fruits from Spain and determined their chemical structures without saponification. The major monoesterified capsanthin was identified as 3 -0-myristoylcapsanthin. It is suggested that the rate of esterification of fatty acid to the hydroxyl group on the cyclopentane ring of capsanthin is different to that on the cyclohexene ring. 

CAPSANTHIN-ESTER III-IV 3-CAPSOnUBlN-ESTER Ml 6 CAPSANTHIN-ESTEfi Hi... 

Carotenoids are also present in animal products such as eggs, lobsters, greyflsh, and various types of hsh. In higher plants, they occur in photosynthetic tissues and choloroplasts where their color is masked by that of the more predominant green chlorophyll. The best known are P-carotene and lycopene but others are also used as food colorants a-carotene, y-carotene, bixin, norbixin, capsanthin, lycopene, and P-apo-8 -carotenal, the ethyl ester of P-apo-8-carotenic acid. These are Upid-soluble compounds, but the chemical industry manufactures water-dispersible preparations by formulating coUoid suspensions by emulsifying the carotenoids or by dispersing them in appropriate colloids. ... 

Paprika contains capsombin and capsanthin (Fig. 8.3) which occur mainly as the lauric acid esters, and about 20 other carotenoid pigments. Paprika is produced in many countries which have developed their own specialties. Cayenne or cayenne pepper, produced from a different cultivar of C. annum, is usually more pungent. C. frutescens is the source of the very pungent Tabasco sauce. Paprika oleoresin is produced by solvent extraction of the ground powder. Obviously paprika supplies both flavor and color and its use is limited to those products compatible with the flavor. The recent rise in demand for tomato products in the form of pizza, salsa, etc., has increased the demand for paprika. Paprika is used in meat products, soups, sauces, salad dressings, processed cheese, snacks, confectionery and baked goods.1018... 

Matsufuji H, Nakamura H, Chino M, Takeda M (1998) Antioxidant activity of capsanthin and the fatty acid esters in paprika (Capsicum annuum). J Agric Food Chem 46 3468-3472 WaU MM, WaddeU CA, Bosland PW (2001) Variation in P-carotene and total carotenoid content in fruits of Capsicum. HortScience 36 746-749... 

Paprika color is obtained by extraction from the fruit of red peppers Capsicum annuum) and contains capsanthin and its esters, formed from acids, such as lauric acid, myristic acid, and palmitic acid, in large amounts as its color components. Commercially available paprika colors are known to have different compositions of these color components, depending on the material from which the paprika color is extracted this makes the identification of paprika color, based on the analysis of the color components, impossible, causing difficulty in developing a simple, rapid, and reliable identification method for the... 

When a paprika color standard, before saponification, was subjected to Cl8 TLC, a number of overlapping spots were observed, and a satisfactory separation could not be obtained. This was probably due to the paprika color containing a large number of esters. Paprika color is known to be hydrolyzed into a carotenoid and a fatty acid when saponified under mild conditions. Thus, a paprika color standard, after saponification, was subjected to TLC using a solvent system of acetonitrile-acetone-n-hexane (11 7 2) on a C18 plate. It was found that the paprika color standard, after saponification, was satisfactorily separated into a main spot having an Rf value of 0.50 and two subspots having Rf values of 0.60 and 0.75 (Fig. 3A). The main spot was identical with the spot of the capsanthin standard in terms of its Rf value, color, and shape (Fig. 3C). 

A sensitive HPLC multimethod was developed by BreithaupT for the determination of the carotenoid food additives (CFA) norbixin, bixin, capsanthin, lutein, canthaxanthin, b-apo-80-carotenal, b-apo-80-carotenoic acid ethyl ester, b-carotene, and lycopene in processed food using an RP C30 column. For unequivocal identification, the mass spectra of all analytes were recorded using LC-(APcl) MS. For extraction, a manual process as well as accelerated solvent extraction (ASE) was applied. Important ASE parameters were optimized. ASE was used for the first time to extract CEA from various food matrices. Average recoveries for all analytes ranged from 88.7% to 103.3% (manual extraction) and from 91.0% to 99.6% (ASE), with the exception of norbixin using ASE (67.4%). Limits of quantitation (LOQ) ranged from 0.53 to 0.79 mg/L. The presented ASE method can be used to monitor both, forbidden application of CFA or the compliance of food with legal limits. 

Carotenoid composition of paprika fruit is shown in fig.2. The fruit distributed mono- and di-fatty acid esters of capsanthin and capsorubin in addition to free pigments, GLC analysis of fatty acids esterified with the carotenoid pigment indicated that capsanthin and capsorubin esterified mainly with saturated fatty acid to form diesters. Although unsaturated fatty acids are predominant in paprika, they were detected only with the fraction of capsanthin monoesters. 

Carotenoids occur free or as esters of fatty acids or as complexes with proteins and carbohydrates for example, in paprika, capsanthin is esterified with lauric acid. In live lobster, astaxanthin is complexed with protein the astaxanthin-protein complex is blue-gray, the color of live lobster, but on heating, the complex is broken and the freed astaxanthin imparts its red color to the cooked lobster. 

---