Identification of thiazolidines in guava: stereochemical studies

Fernández, Xavier; Duñach, Élisabet; Fellous, R.; Lizzani‐Cuvelier, Louisette; Loiseau, Michel; Dompe, Vincent; Cozzolino, Francis; George, Gérard; Rochard, Sophie; Schippa, Christine

doi:10.1002/ffj.996

Cited by 13 publications

(18 citation statements)

References 9 publications

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“…With the exception of thiazol, other sulfur compounds previously reported in guava fruit were not detected here, even though we specifically looked for these compounds in SPME and SDE extracts. This variability in volatile compounds could be due to differences in cultivar, fruit maturity stage, geographical zone and/or volatile isolation method.…”

Section: Resultsmentioning

confidence: 81%

Odour-active compounds in guava (Psidium guajavaL. cv. Red Suprema)

Pino¹,

Bent²

2013

J. Sci. Food Agric.

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Section: Resultsmentioning

confidence: 81%

Odour-active compounds in guava (Psidium guajavaL. cv. Red Suprema)

Pino¹,

Bent²

2013

J. Sci. Food Agric.

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“…13 Four thiazolidines corresponding to the ethyl and methyl esters of 2methyl-thiazolidine-4-(R)-carboxylate in their transand cis-stereochemistry were identified in yellow flesh guava. 14,15 This is surprising, as the concentration of free cysteine is low in vegetables and animals.…”

Section: Introductionmentioning

confidence: 99%

The role of cysteine and cysteine–S conjugates as odour precursors in the flavour and fragrance industry

Starkenmann

Troccaz

2008

Flavour & Fragrance J

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Volatile sulphur compounds are important odorants in the flavour and fragrance industries. Recent developments in the field have reinvigorated sulphur compound research, particularly with regard to the precursor compounds of volatile thiols. The present review concentrates on the role of cysteine and cysteine-S conjugates as precursor compounds for a variety of aromas and examines the chemical and enzymatic pathways of degradation and biotransformation. Cysteine is an important source of sulphur in flavour chemistry and may be degraded into hydrogen sulphide, which can further participate in other reactions. Direct reactions of cysteine and the pathways particular to various flavours and fragrances are discussed, with an emphasis on the precursor compounds cysteine-S conjugates. The importance of cysteine precursors in plants, including onion, wine, passion fruit, bitter orange, asparagus and bell pepper and the formation of natural scents in cats and humans are discussed. Reactivity of Cysteine with Aldehydes and Ketones Reaction of cysteine with saturated carbonylsCysteine 1 is a bidentate nucleophile. The nitrogen is considered a hard nucleophile and the sulphur atom a soft nucleophile. 5 This leads to the formation of the Schiff base when cysteine 1 reacts with saturated aldehydes 2

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“…Recently identified as trace compounds in guava, 1 thiazolidines are used as flavouring agents in various foods. These compounds have not been often identified in natural products.…”

Section: Introductionmentioning

confidence: 99%