Synthesis and Characterisation of <i>α</i>‐Glycosyloxyamides Derived from Cyanogenic Glycosides

Sendker, Jandirk; Nahrstedt, Adolf

doi:10.1002/pca.1237

Cited by 7 publications

(7 citation statements)

References 23 publications

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“…Compound 11 exhibiting a protonated molecule at m/z 304.1 probably is a passiguatemalin derivative with one unsaturation in cyclopentene ring, such as occur in gynocardin, a cyclopentene reported from P. incarnata (Jaroszewski et For some cyanogenic plants, primary amide glucosides have been detected, whose structures correspond to the respective cyanogenic glycoside, in that the nitrile moiety has been converted into a primary carboxamide group. These amides were exclusively found in air-dried leaves whereas fresh material of the same plants do not yield detectable amounts of amides, only a cyanogenic glycoside (Jaroszewski et al, 2002;Sendker & Nahrstedt, 2010). The cyanogenic amide glycoside 12 at Rt 34.9 min exhibited protonated molecule at m/z 332.3.…”

Section: Passiflora Quadrangularismentioning

confidence: 99%

“…In the hydroethanolic extract of P. quadrangularis two cyanogenic glycosides were also found. Molecules bearing a positive charge, such as cyanogenic glycosides, ionize best with positive ion ESI (Sendker & Nahrstedt, 2010). Compound 11 at 32.4 min exhibited a protonated molecule at m/z 304.1 and the molar mass was deduced as 303.1u.…”

Section: Passiflora Quadrangularismentioning

confidence: 99%

“…Dhurrin (4-hydroxymandelamide glucoside) is a prunasin derivative with an extra hydroxyl group on benzoyl group (Seigler et al, 2005). According to Sendker & Nahrstedt (2010) Table 2). Compound 12 was tentatively characterized as dhurrinamide derivative.…”

Section: Passiflora Quadrangularismentioning

confidence: 99%

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Chemical composition of hydroethanolic extracts from five species of the Passiflora genus

Sakalem¹,

Negri²,

Tabach³

2012

Rev. bras. farmacogn.

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Abstract:The diversifi ed genus Passifl ora is well distributed all over Brazil, and many species have been long used as medicinal plants, mainly against anxiety disturbances. This effect has been attributed to its rich fl avonoid composition. Flavonoids' main class, fl avonoid glycosides, has presented central action, particularly as sedativehypnotic, anxiolytic and analgesic. The objective of the present study was to make a phytochemical screening of fi ve little studied Passifl ora species, in order to evaluate their phenolic composition. For this aim, HPLC-DAD-ESI-MS/MS was used. After the preparation of the hydroalcoholic extracts, each species was evaluated by direct injection electrospray ionization (ESI) and tandem mass spectrometry. Although belonging to the same genus, the composition of each species presented particularities; this justifi es the importance of studies aiming for the phenolic composition of different Passifl ora species. Flavones C-glycosides were detected in all extracts, and are found as the main constituents in P. vitifolia, P. coccinea, P. bahiensis and P. sidifolia. In this last one, fl avone-6,8-di-C-glycoside, apigenin-6-C-rhamnosyl-8-C-arabinoside are present in high content. Cyclopassifl osides were found in high content together with cyanogenic glycosides in P. quadrangularis, while in P. coccinea, besides fl avones-Cglycosides were also found procyanidins.

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Section: Passiflora Quadrangularismentioning

confidence: 99%

Section: Passiflora Quadrangularismentioning

confidence: 99%

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Chemical composition of hydroethanolic extracts from five species of the Passiflora genus

Sakalem¹,

Negri²,

Tabach³

2012

Rev. bras. farmacogn.

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“…The presence of a mandelic acid moiety in 6 and a mandelic acid amide moiety in 5 was supported by the MS data; namely, an exact neutral fragment loss between [M + H] + and its respective fragment at m / z 267 was 152.0466 amu (C 8 H 8 O 3 ) for 6 and 151.0646 amu (C 8 H 9 NO 2 ) for 5 . Further support arose from characteristic CO stretching and N–H deformation vibrations that occurred in their IR spectra (1719 cm –1 for 6 and 1670, 1602 cm –1 for 5 ) . The sugar moiety was identified as d -glucose by capillary electrophoresis of a hydrolysate after derivatization with ( S )-(−)-1-phenylethylamine .…”

Section: Resultsmentioning

confidence: 99%

“…Compound 1 was isolated from fresh green leaves of P. laurocerasus as described previously . Compound 2 was obtained from 1 based on a prior investigation . Compound 3 was obtained as a mixture of 2 S - and 2 R -epimers after boiling 2 for 1 h in 0.1 M sodium hydroxide, acidifying with 10% trifluoroacetic acid to pH 2–3, and repeatedly extracting this solution with a water-saturated mixture of two parts 1-butanol and one part 2-propanol.…”

Section: Experimental Sectionmentioning

confidence: 99%

Occurrence of Benzoic Acid Esters as Putative Catabolites of Prunasin in Senescent Leaves of Prunus laurocerasus

2016

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Prunus laurocerasus is an evergreen shrub containing large quantities of the cyanogenic glycoside prunasin (1) in its leaves, which decomposes to prunasin amide (2) or glucose-1-benzoate (4) when the leaves become chlorotic as a result of senescence or pseudosenescence. This study was aimed at the systematic identification of senescence-associated metabolites to contribute further insight into the catabolism of 1. LC-ESIMS profiles of senescent and green leaves were analyzed by principal component analysis. In senescent leaves, the concentrations of 36 compounds were increased significantly including several benzoic acid derivatives, of which prunasin amide-6'-benzoate (5) and prunasin acid-6'-benzoate (6) were isolated and identified. The observed metabolic changes were also induced by treatment of P. laurocerasus shrubs with exogenous ethylene. The data presented support an oxidative catabolism of 1 without release of hydrogen cyanide and the remobilization of its nitrogen in the course of senescence. The results are discussed in the context of functional diversification and drug discovery, where senescent plant material represents a widely unexplored source for the discovery of natural products.

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Cyanogenesis in Higher Plants and Animals

Lechtenberg

2011

Encyclopedia of Life Sciences

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Cyanogenesis describes the ability of living organisms to liberate hydrogen cyanide from stored cyanogenic glycosides, cyanogenic lipids or cyanohydrins on tissue damage by hydrolysis and/or decomposition. It has been described for over 2650 species of higher plants and some animals. Together with plant β‐glucosidases and hydroxynitrile lyases cyanogenic glycosides are the constituent part of a preformed defence system. Today it's generally accepted that cyanogenic glycosides also may serve as storage form for reduced nitrogen and sugar. Chemically, cyanogenic glycosides are glycosides of α‐hydroxynitriles (cyanohydrins). The structures are biogenetically related to only a few precursor amino acids. Biogenetically closely related are some noncyanogenic glucosides of β‐ and γ‐hydroxynitriles ( cyanoglucosides ). Their biological function is not fully understood until today. Many food plants are cyanogenic and great efforts are made to optimise detoxification. Humans are able to detoxify considerable amounts of HCN. Although acute intoxication is rare, the daily consumption of subacute amounts of cyanogenic glycosides leads to chronic diseases, caused by increased plasma levels of the human detoxification products. The presence of cyanogenic glycosides in the animal kingdom appears to be restricted to Arthropoda. Some insects, often aposematically coloured, either de novo synthesise cyanogenic glycosides and/or sequester them from their host plants. Key Concepts: Cyanogenic glycosides are secondary metabolites known from more than 2650 different plant species. Cyanogenic glycosides are glycosides of α‐hydroxynitriles, derived from five proteinogenic amino acids (Phe, Tyr, Val, Ile and Leu) and from the nonproteinogenic amino acid cyclopentenyl glycine. Acalyphin is apparently derived from nicotinic acid. Cyanogenic plants are able to liberate hydrogen cyanide from their cyanogenic glycosides upon disruption of plant tissue. Cyanogenic glycosides and their corresponding degrading enzymes (β‐glucosidases; hydroxynitrile lyases) are part of a preformed defence system. Thus, they can be regarded as phytoanticipins. Additional roles and functions of cyanogenic glycosides include storage of reduced nitrogen and sugar, transportation of nitrogen and the turnover of nitrogen into primary metabolism. The presence of cyanogenic glycosides in animals appears to be restricted to Arthropoda. Some insects are strongly associated with their cyanogenic host plants. They sequester the cyanogenic glycosides from these pants as well as carry out de novo biosynthesis of these compounds.

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Synthesis and Characterisation of α‐Glycosyloxyamides Derived from Cyanogenic Glycosides

Abstract: Thus, α-glycosyloxyamides can be obtained in sufficient amounts and purity to serve as references for further studies on the catabolism of cyanogenic glycosides and the detoxification of cyanogenic foodplants using the new aspect of nitrile hydrolysis with (endogenous) hydrogen peroxide.

Cited by 7 publications

References 23 publications

Chemical composition of hydroethanolic extracts from five species of the Passiflora genus

Chemical composition of hydroethanolic extracts from five species of the Passiflora genus

Occurrence of Benzoic Acid Esters as Putative Catabolites of Prunasin in Senescent Leaves of Prunus laurocerasus

Cyanogenesis in Higher Plants and Animals

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