Yellow passion fruit

Determination of the enantiomeric distribution of some chiral sulfur-containing trace components of yellow passion fruit"... 

B. Weber, B. Maas and A. Mosandl, Stereoisomeric flavor compounds. 72. Stereoisomeric distribution of some cliiral sulfur containing trace components of yellow passion fruits , ]. Agric. Food Chem. 43 2438-2441 (1995). 

Mercadante A.Z., Britton, G., and Rodriguez-Amaya, D.B., Carotenoids from yellow passion fruit (Passiflora edulis), J. Agric. Food Chem., 46, 4102, 1998. 

Possible differences are also well illustrated by 3-thio- and 3-methyl-thiohex-anols and their esters (Table 1). Among these compounds, there is a tendency for the (R) enantiomers to have a typical, fruity aroma. However, for 3-methylthiohexanol (an aroma component of yellow passion fruit) this situation is reversed the (S) enantiomer had the characteristic fruity aroma ( exotisch, fruchtig ).52 For the separation of enantiomers of odorous compounds, enan-tioselective GLC with chiral stationary phases, and MGDC techniques using a conventional capillary column and an enantioselective column are commonly used.53... 

Talcott ST, Percival SS, Pittet-Moore J and Celoria C. 2003. Phytochemical composition and antioxidant stability of fortified yellow passion fruit (Passiflora edulis). J Agric Food Chem 51 (4) 935—941. 

NT529 Demole, E., P. Enggist, M. Winter, et al. Megastigma 5,8 dien-4 One, an aroma constituent of the yellow passion fruit and Virginia tobacco. Helv Chim Acta 1979 62 67. 

Owing to their unique and delicate flavour, species of the genus Passiflora have been the subject of intensive research on their volatile constituents [13]. The purple passion fruit (Passiflora edulis Sims) is a tropical fruit native to Brazil but is now grown in most tropical and subtropical countries [50]. Purple passion fruit is cultivated in Australia, India, Sri Lanka, New Zealand, and South Africa [48]. Yellow passion fruit (Passiflora edulis t flavicarpa) is one of the most popular and best known tropical fruits, having a floral, estery aroma with an exotic tropical sulfury note [62]. Yellow passion fruit is cultivated in Brazil, Hawaii, Fiji, and Taiwan [48]. Because of its more desirable flavour, the purple passion fruit is preferred for consumption as fresh fruit, whereas the yellow passion fruit is considered more suitable for processing [28]. 

The analyses of the flavour composition of yellow passion fruits were performed by four dilferent isolation techniques, namely vacuum headspace sampling (VHS), the dynamic headspace method, simultaneous distillation and extraction at atmospheric pressure, and simultaneous distillation and extraction under reduced pressure [62]. Significant differences were found not only in the chemical composition of the resultant extracts but also in their sensory properties. The most representative and typical extract was obtained by VHS. 

Later, the chemical characterisation of the volatiles from yellow passion fruit essence and from the juice of the fruit was done by GC-MS and GC-olfactom-etry (GC-O) [27]. Esters were the components found in the largest concentrations in passion fruit juice and essence extracted with methylene chloride. Analysis by GC-O yielded a total of 66 components which appeared to contribute to the aroma of passion fruit juice and its aqueous essence. Forty-eight compounds were identified in the pulp of Brazilian yellow passion fruits (Passiflora edulis f. flavicarpa) [48]. The predominant volatile compounds belonged to the classes of esters (59%), aldehydes (15%), ketones (11%), and alcohols (6%). 

Werkoff, P., Giintert, M., Krammer, K Sommer, H., and Kaulen, J. 1998. Vacuum headspace method in aroma research Flavor chemistry of yellow passion fruits. J. Agric. Food Chem. 46 1076-1093. 

The impact of commercial yeast strains on wine fermentation leads to the formation of metabolites of yellow passion fruit (Passiflora edulis Sims) 2-methyl-4-propyl-l,3-oxathian 79 (10MI282,98JAFC1076,98MI53). This oxathian exists in four enantiomeric forms, 79a-d, and there are pronounced sensory differences between them (06CRV4099) for their enan-tioselective synthesis, cf. (84HCA947, 85LA1185). It should be mentioned that most of the aforementioned sulfur heterocycles are sold worldwide as fragrances and flavors. 

As shown in Figure 6, pentanol-2 and heptanol-2, isolated by preparative GC from yellow passion fruits, mainly consisted of the (S)-enantiomer the optical purity of heptanol-2 was higher than the purity of pentanol-2. In contrast, heptanol-2 isolated from the purple variety mainly consisted of the (R)-enantiomer (92 %). Heptanol-2, obtained by alkaline hydrolysis of the 2-heptylesters in purple passion fruits, was optically pure and possessed the (R)-configuration. Thus, the two passion fruit varieties contain different enantiomers of heptanol-2. 

Ethyl 3-hydroxybutanoate, isolated from yellow passion fruit, mainly consisted of the (S)-enantiomer (82 %), comparable to the product, obtained by yeast reduction of the corresponding 3-ketoacid ester (see above). In contrast, ethyl 3-hydroxybutanoate in purple passion fruit and mango mainly consisted of the (R)-enantiomer (69 % and 78 %). 

Engel, K. H., Tressl, R. (1991). Identification of new sulfur-containing volatiles in yellow passion fruits (Passiflora edulis f. flavicarpa). J. Agric. Food Chem., 39, 2249-2252. 

Opposite enantiomers of 3-hydroxyacid esters of different chain lengths in fruits, such as yellow passion fruit (16) and the influence of the structures of oxoprecursors on the optical purities of 3-hydroxyacid derivatives in incubation experiments with pineapple indicate a competition of oxidoreductases in plant systems comparable to baker s yeast. 

From over 400 species of passion fmit, two became commercially important crops the purple passion fruit, Passiflora edulis, var. purpurea and the yellow passion fruit or maracuja, Passiflora edulis, var. flavicarpa. Both are well recognized by their delicious, acid, gelatinous, juicy pulp with its characteristic, exotic, sharp, green, fruity, sulphurous and floral, fruity note, whereas the yellow variety is fresher, greener with a stronger sulfury note. 

M. Winter, A. Furrer, B. Willhalm and W. Thommen. Identification and Synthesis of two New Organic Sulfur Compounds from the Yellow Passion Fruit (Passiflora edulis f. flavicarpa). Helv. Chim. Acta, 52, 1613-1620 (1976). 

G. Singer, G. Heusinger, O. Frbhlich, P. Schreier and A. Mosandl. Chirality evaluation of 2-methyl-4-propyl-l,3-oxathiane from the yellow passion fruit. J. Agric. Food Chem., 34, 1029-1033 (1986). 

Figure V. Possible pathway for the biosynthesis of secondary alcohols, their esters, and other typical constituents of passion fruit. Enzyme (El) is operative in yellow passion fruit. The antipodal reduction catalyzed by enzyme (E2) and the following esterification take place only in the purple variety.

The enantiomeric composition of 3-hydroxyacid esters in passion fruit, mango and pineapple have been investigated. Figure VII presents the separation of (R)- and (S)-3-hydroxybutanoates. The compounds in yellow passion fruit were mainly of the (S)-(+)-configuration as predicted for intermediates of B-oxidation. In the purple variety, and in mango, the (R)-(-)-enantiomers predominate. These compounds may be found as an offshoot of de novo lipid synthesis or by hydration of (Z)-2-enoyl-CoA leading to (R)-(-)-3-hydroxyacyl-CoA (1 2) ... 

In 1976 Winter et al. (22) identified 3-methylthio-hexanol and a mixture of (Z)- and (E)-2-methyl-1,3-oxa-thiane in yellow passion fruit. 3-Methylthiohexanol possesses a green fatty and sulfury note and imparts the character of fresh fruit to the juice of passion fruits. The oxathianes were described as key compounds for the typical aroma of passion fruit and the (Z)-isomer had a stronger flavor. Pickenhagen and Bronner-Schindler (23) synthesized the enantiomers of (+)- and (-)-(Z)-2-methyl-... 

C6H10O3, Mr 130.14, r/25 1.024-1.029, nl 1.417-1.422, is a colorless liquid with a fruity-ethereal, sweet odor reminiscent of green apples. It is used to create fresh fruity top notes in feminine fine fragrances. Ethyl acetoacetate occurs in flavors of natural materials like coffee, strawberries and yellow passion fruits [26a]. 

Laboissiere et al. (2007) showed that high-pressure processing (300 MPa, 5 min, 25°C) could be used to preserve yellow passion fruit pulp, yielding a ready-to-drink juice with improved sensory quality, free from cooked and artificial flavor attributes, as compared to commercial juices. High-pressure treatment did not cause any significant modifications in compounds responsible for aroma, flavor, and consistency. 

Laboissiere, L.H.E.S., Dehza, R., Banos, A.M., Rosenthal, A., Camargo, L.M.A.Q., and Junqueira, R.G. 2007. Effects of high hydrostatic pressure (HHP) on sensory characteristics of yellow passion fruit juice. Innovative Eood Science and Emerging Technologies 8 469-477. 

C oH 02, Mr 168.24. A liquid with a fruity-flowery odor, bp. 95-96°C (40Pa). (-)-d-J. ([aJu -30.4°, neat), found, among others, in jasmin(e) absolute and tea flavor, (+)-d-J. occurs in tuberose absolute, peach and mango flavor. For general and stereoselective syntheses, see Lit.. The peach-like smelling y-J. in the (+)-form contributes to the flavors of peach, mango, and yellow passion fruit. For analysis and preparative chromatographic separation of the enantiomers, see Lit., biosynthesis Lit.. The jasmolac-tones A-D are bicyclic structures. ... 

C,H,60S, Mr 160.27 discovered and synthesized in 1976 as the typical flavor compound of the yellow passion fruit (Passiflora edulis) (see fruit flavors). Racemic cis-Zira/is-mixture 1 10, oil with an exotic fruity odor, bp. 85 -86 °C (1.6 kPa). Synthesis and sensory evaluation of the four stereoisomers demonstrated that the (-F)-(2S,4/f)-form was the compound with the typical passion fruit character, olfactory threshold in water 2 jmb, [alo" -f56.1 (CCI4). According to chiral analysis, however, the passion fruit contains the (4S)-epimer pair with an untypical, sulfurous, herby-green or, respectively flowery odor (-)-(2R,4S), [a]g -56.1 , and (-)-(2S,4S), (a]g -117.6°. For biosynthesis, see Ut.. ... 

Yapo, B. M. and Koffi, K. L. (2008). The polysaccharide composition of yellow passion fruit cell wall Chemical and macromolecular features of extractable pectins and hemicellulosic polysaccharides. Journal of the Science of Food and Agriculture 88, 2125-2133. 

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