Prunus

Benzaldehyde Cyanohydrin. This cyanohydrin, also known as mandelonitrile [532-28-5] is a yellow, oily Hquid, insoluble in water, but soluble in alcohol and diethyl ether. Mandelonitrile is a component of the glycoside amygdalin [29883-15-6] a precursor of laetdle [1332-94-7] found in the leaves and seeds on most Prunus species (plum, peach, apricot, etc). In 1832, mandelonitrile was the first cyanohydrin to be synthesized. 

As early as 1908, Rosenthaler found in the ferment mixture of emulsin a u-oxynitrilase , which directed the addition of hydrocyanic acid (hydrogen cyanide) to benzaldehyde asymmetrically to give x-hydroxybenzeneacetonitrilc (mandelonitrile)9. This result was confirmed1 °, however, it was not until 1963 that Pfeil ct al. first isolated and characterized the enzyme (R)-oxyni-trilase [EC 4.1.2.101 from bitter almonds (Prunus amygdalus)1 12. The yellow-colored enzyme contains a flavin-adenine dinucleotide (FAD)11 and loses its activity by splitting off this prosthet-... 

Swain, T. and Hillis, W.E., The phenolic constituents of Prunus domestica. 1. The quantitative analysis of phenolic constituents, J. Set Food Agric., 10, 63, 1959. 

Apricots, cherries, peaches (including nectarines and similar hybrids), plums (Prunus domestica including all subspecies), cornel cherries... 

As reported by Griengl and coworkers, benzaldehyde, decanal, undecanal, and dodecanal were reacted with HCN in a two-phase solvent system aqueous buffer and ionic liquids 1 -ethyl-3-methylimidazolium tetrafluoroborate, 1 -methyl-3-propylimidazolium tetrafluoroborate, and l-butyl-3-methyl-imidazolium tetrafluoroborate in the presence of the HNLs from Prunus amygdalus and Hevea brasiliensis. When compared with the use of organic solvents as the nonaqueous phase, the reaction rate was significantly increased and the enantioselectivity remained good [51]. 

Starting from enantiomerically pure 4-methylsulfanyl-mandelonitrile, thiamphenicol and florfenicol have been enantioselectively synthesized (Figure 5.14). The enantiomerically pure 4-methylsulfanyl-mandelonitrile was obtained by hydrocyanation reaction of 4-methy lsulfany 1-benzaldehyde catalyzed by (M)-hydroxynitrile lyase of Badamu (almond from Xinjiang, China) (Prunus communis L. var. dulcis Borkh), which, after an extensive screening, was found to be a highly effective bio-catalyst for this reaction [85]. 

Dreveny, I., Kratky, C. and Gruber, K. (2002) The active site of hydroxynitrile lyase from Prunus amygdalus modeling studies provide new insights into the mechanism of cyanogenesis. Protein Science A Publication of the Protein Society, 11, 292-300. 

Rhodococcus erythropolis NCIMB 11540 has been employed as biocatalyst for the conversion of (R)- or (.S )-cyanohydrins to the corresponding (R)- or (S)-a-hydroxycarboxylic acids with an optical purity of up to >99% enatiomeric excess (ee) [27-29] the chiral cyanohydrins can separately be produced using hydroxynitrile lyase from Hevea braziliensis or from Prunus anygdalis [30]. Using the combined NHase-amidase enzyme system of the Rhodococcus erythropolis NCIMB 11 540, the chiral cyanohydrins were first hydrolyzed to the... 

Prunus armeniaca (apricot) Prunus avium (sweet cherry) Prunus domestica (plum)... 

Carbonaro M, Mattera M, Nicoli S, Bergamo P and Cappelloni M (2002), Modulation of antioxidant compounds in organic vs conventional fruit (peach, Prunus persica L., and pear, Pyrus communis L.) , J Agric Food Chem, 50, 5458-5462. 

Lombardi-Boccia G, Lucarini M, Lanzi S, Aguzzi A and Cappelloni M (2004), Nutrients and antioxidant molecules in yellow plums (Prunus domestica L.) from conventional and organic productions a comparative study , J Agric Food Chem, 52, 90-94. 

Monagas M, Garrido I, Lebron-Aguilar R, Bartolome B and Gomez-Cordobes C. 2007. Almond (Prunus dulcis (Mill.) D.A. Webb) Skins as a potential source of bioactive polyphenols. J Agric Food Chem 55(21) 8498-8507. 

Ruiz D, Egea J, Gil MI and Tomas-Barberan FA. 2005. Characterization and quantitation of phenolic compounds in new apricot (Prunus armeniaca L.) varieties. J Agric Food Chem 53(24) 9544— 9552. 

Gross J. 1985. Carotenoid pigments in the developing cherry (Prunus avium) cv. Donissen s Gelbe . Gartenbauwiss 50 88-90. 

Marty I, Bureau S, Sarkissian G, Gouble B, Audergon JM and Albagnac G. 2005. Ethylene regulation of carotenoid accumulation and carotenogenic gene expression in colour-contrasted apricot varieties (Prunus armeniaca). J Exp Bot 56(417) 1877-1886. 

Gonsalves B, Landbo AK, Let M, Silva AP, Rosa E and Meyer AS. 2004. Storage affects the phenolic profiles and antioxidant activities of cherries (Prunus avium L.) on human low-density lipoproteins. J Sci Food Agric 84(9) 1013-1020. 

Beyer, W.N. and J. Moore. 1980. Lead residues in eastern tent caterpillars (Malacosoma americanum) and their host plant (Prunus serotina) close to a major highway. Environ. Entomol. 9 10-12. 

Cherry, Prunus avium Europe (Slovenia), bark Uncontaminated areas 0.06 FW 1... 

---