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Arquivo Técnico Sweet proteins Sweet proteinS – POTENTIAL REPLACEMENT FOR ARTIFICIAL LOW CALORIE SWEETENERS Exponential growth in the number of patients suffering from diseases caused by the consumption of sugar has become a threat to mankind’s health. Artificial low calorie sweeteners available in the market may have severe side effects. It takes time to figure out the long term side effects and by the time these are established, they are replaced by a new low calorie sweetener. Saccharine has been used for centuries to sweeten foods and beverages without calories or carbohydrate. It was also used on a large scale during the sugar shortage of the two world wars but was abandoned as soon as it was linked with development of bladder cancer. Naturally occurring sweet and taste modifying proteins are being seen as potential replacements for the currently available artificial low calorie sweeteners. Interaction aspects of sweet proteins and the human sweet taste receptor are being investigated. 16 FOOD INGREDIENTS BRASIL Nº 8 - 2009 www.revista-fi .com SWEET AND TASTE MODIFYING T1R class [8-10] of taste-specific tions of these proteins are the low calo- PROTEINS proteins hypothesized to function rie sweetener industry and the cola, in combination as a heterodimer. snacks, food and chocolate industries. The prevalence of obesity and The human T1R2-T1R3 receptor diabetes has increased dramatically recognizes natural and synthetic BRAZZEIN in recent years in the United States, sweetness and T1R1-T1R3 rec- Brazzein is the smallest, most with similar patterns seen in sev- ognizes umami taste [11,12]. So heat-stable [13] and pH-stable eral other countries including India far there are seven known sweet member of the set of proteins known [1] as well. Diabetes mellitus is a and taste-modifying proteins, to have intrinsic sweetness. The chronic disease caused by inherited namely Brazzein [13], Thaumatin protein, consisting of 54 amino acid or acquired deficiency in production [14], Monelin [15], Curculin [16], residues, is reported to be between of insulin by the pancreas or by the Mabinlin [17], Miraculin [18] and 500 and 2000 times sweeter than ineffectiveness of the insulin pro- Pentadin [19]. Properties and sucrose [22] and represents an ex- duced [2]. Artificial sweeteners like characteristics of these proteins cellent alternative to available low Saccharin, Aspartame, Cyclamate are illustrated in Table 1. calorie sweeteners. It was originally and AcesulfameK are used world- The key residues on the protein isolated from the fruit of an African wide as low calorie sweeteners by surface responsible for biological plant Pentadiplandra brazzeana patients affected by diseases linked activity have not yet been identi- Baillon [23]. Heat and pH stability to the consumption of sugar, e.g. fied with certainty for any of these of the protein make it an ideal sys- diabetes, hyperlipemia, caries, obe- proteins [20]. Monellin was found tem for investigating the chemical sity, etc., but they have side effects to be 100000 times sweeter than su- and structural requirements of a such as psychological problems, crose on a molar basis [21], followed sweet-tasting protein. Based on the mental disorders, bladder cancer, by Brazzein and Thaumatin which wild-type brazzein, 25 mutants were heart failure and brain tumors [3-7]. are 500 times [13] and 3000 times produced to identify critical regions Sweet proteins have the potential sweeter then sucrose [14] respec- important for sweetness. To assess to replace these artificial sweeten- tively (the latter two on a weight their sweetness, psychophysical ex- ers, by acting as natural, good, low basis). All of these proteins have periments were carried out with 14 calorie sweeteners, as we know that been isolated from plants that grow human subjects. First, the results proteins do not trigger a demand for in tropical rainforests. Although suggest that residues 29–33 and insulin in these patients whereas most of them share no sequence 39–43, plus residue 36 between these sucrose does. homology or structural similarity, stretches, as well as the C-terminus In humans, the sweet taste is Thaumatin shares extensive homol- are involved in the sweetness [24]. mainly due to the recently discov- ogy with certain non-sweet proteins Second, charge plays an important ered T1R2-T1R3 receptor [8-10], found in other plants [15]. role in its interaction with the sweet two of the three members of the The potential industrial applica- taste receptor [24]. Table 1: Comparison of thaumatin, monellin, mabinlin, pentadin, brazzein, curculin and miraculin. Thaumatin Monellin Mabinlin Pentadin Brazzein Curculin Miraculin Pentadiplandra Pentadiplandra Thaumatococcus Dioscoreophyllum Capparis Curculingo l Richadella Source brazzeana brazzeana danielli Benth cumminsii Diels masakai Levl atifolia dulcifica Baillon Baillon Geographic West Africa West Africa China West Africa West Africa Malaysia West Africa distribution Variants I, II, a, b, cª –— I, II - a, III, IVª -–— –— –— –— Sweetness factor 3000 3000 100 500 2000 550 –— (weight basis) Molecular mass 22.2 10.7 12.4 12.0 6.5 24.9 98.4 (active form, kDa) b 45 (A chain) 33 (A chain) Amino acids 207 ? 54 114 191 50 (B chain) 72 (B chain) Dimer ( Tetramer Active form Monomer Dimer (A + B) Dimer (A + B) ? Monomer A +A) (A+A+A+A) Source: Adapted from Kurihara (1994). ªAt least five different forms of thaumatin (Lee et al., 1988) and four different forms of mabinlin (Nirasawa et al., 1994) have been identified.b A chromatographic fraction containing a 12-kDa protein was sweet. This same fraction, when subjected to electrophoresis under non-reducing condi- tions showed bands in the region between 22 and 41 kDa, suggesting the presence of subunits. www.revista-fi.com FOOD INGREDIENTS BRASIL Nº 8 - 2009 17 Sweet proteins THAUMATIN may cause separation of the sub- sional model has been built from units and denaturation of the pro- the X-ray coordinates of GNA, a The thaumatins are a class of tein. Despite misgivings about the mannose-binding lectin from snow- intensely sweet proteins isolated stability of the protein to heat and drop (Galanthus nivalis) [38]. The from the fruit of the tropical plant acid, downstream processes have three mannosebinding sites pres- Thaumatococcus danielli. The protein been established. Its D-enantiomer ent in GNA were found in curculin crystallizes in a hexagonal lattice after has been crystallized and analyzed but were not functional. Some well a temperature shift from 293 to 277 K. by X-ray crystallography at 1.8 Å exposed regions on the surface of The structure has been solved at 1.6 resolution. Two crystal forms (I the three-dimensional model of the Å resolution. Its fold was found to be and II) were found under crystal- said protein could act as epitopes identical to that found in three other lization conditions similar, but not responsible for the sweet-tasting crystal forms grown in the presence identical, to the crystallization properties of the protein [40]. The of crystallizing agents of differing conditions of natural L-monellin protein can be crystallized by the chemical natures [25]. It consists of [34]. One NMR study of a non- vapor diffusion method using poly- 207 amino acid residues with eight sweet analog in which the AspB7 ethylene glycol 400 as a precipitant. intramolecular disulfide bonds and of protein was replaced by AbuB7 The crystals belong to orthorhombic contains no free cysteine residues. (L-2-Aminobutylicacid), showed space group P2(1)2(1)2(1) with unit It aggregates upon heating at Ph 7.0 similar 3-dimensional structures of cell dimensions: a = 105 Å, b = 271 above 70 degrees C, whereupon its these two proteins, indicating that Å, c = 48.7 Å. The crystals diffract sweetness disappears [26,27]. The the lack of the beta-carboxyl group X-rays to resolution of 3.0 Å and are protein is approximately 10000 times in the AbuB7 analog is responsible suitable for Xray crystallographic sweeter than sugar on a molar basis for the loss of sweetness [35]. Recent studies [41]. [28]. It is a protein that tastes intense- research on identifying binding sites ly sweet only to Old World monkeys on the receptor by means of struc- MABINLIN and to higher primates, including ture-taste relationships, found that Mabinlin is a sweet protein with man [29], as it has been found that four monellin analogues, [AsnA16]-, the highest known thermostablil- the protein binds to certain elements [AsnA22]-, [GlnA25]-, and [AsnA26]- ity [42]. It is derived from Capparis in taste pores of Rhesus monkey foli- monellin were 7500, 750, 2500, and masaikai and its sweetness was es- ate papillae [30]. Thaumatin has been 5500 times as sweet as sucrose on timated to be around 400 times that approved for use in many countries a weight basis, respectively. Thus, of sucrose on weight basis. It consists as both a flavor enhancer and a high- among them, [AsnA22]-monellin and of an A chain with 33 amino acid intensity sweetener [31]. [GlnA25]-monellin were less sweet residues and a B chain composed of than the native monellin [36]. 72 residues. The B chain contains two MONELLIN intramolecular disulfide bonds and is Monellin, a sweet protein, con- CURCULIN connected to the A chain through two sists of two noncovalently associated Curculin which is extracted from intermolecular disulfide bridges [43]. polypeptide chains, an A chain of 44 Curculigo latifolia acts as a good Its heat stability is due to the pres- amino acid residues and a B chain low calorie sweetener. Its maximum ence of these four disulfide bridges of 50 amino acid residues [32]. The sweetness is equal to 0.35 M of su- [44]. The sweetness of Mabinlin-2 is protein can be purified from the fruit crose. It has taste modifying abili- unchanged after 48 hr incubation at of Dioscoreophyllum cumminsii ties since water and sour substances boiling point [17]and of Mabinlin-3 grown in West Africa and is approxi- elicit a sweet taste after consumption and -4 are unchanged after 1 hr at mately 100,000 times sweeter than of curculin [37].
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