Cyanohydrin glycosides of Passiflora: distribution pattern, a saturated cyclopentane derivative from P. guatemalensis, and formation of pseudocyanogenic α-hydroxyamides as isolation artefacts

Jaroszewski, Jerzy W.; Ólafsdóttir, Elín Soffia; Wellendorph, Petrine; Christensen, Jette; Franzyk, Henrik; Somanadhan, Brinda; Budnik, Bogdan; Jørgensen, Lise Bolt; Clausen, Vicki

doi:10.1016/s0031-9422(01)00485-x

Cited by 38 publications

(38 citation statements)

References 36 publications

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“…1). In addition, a few plant species such as Passiflora (Malphigiales, eurosids I) contain cyanogenic glycosides derived from the non-protein amino acid cyclopentenyl glycine (Jaroszewski et al 2002a, b). The specific presence of aromatic cyanogenic glycosides in ferns and gymnosperms indicate that the cyanogenic glycosides initially in nature were aromatic, and that these served as progenitors for aliphatic cyanogenic glycosides.…”

mentioning

confidence: 99%

Cyanogenic glycosides: a case study for evolution and application of cytochromes P450

Bak¹,

Paquette

Morant³

et al. 2006

Phytochem Rev

123

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Cyanogenic glycosides are ancient biomolecules found in more than 2,650 higher plant species as well as in a few arthropod species. Cyanogenic glycosides are amino acid-derived b-glycosides of a-hydroxynitriles. In analogy to cyanogenic plants, cyanogenic arthropods may use cyanogenic glycosides as defence compounds. Many of these arthropod species have been shown to de novo synthesize cyanogenic glycosides by biochemical pathways that involve identical intermediates to those known from plants, while the ability to sequester cyanogenic glycosides appears to be restricted to Lepidopteran species. In plants, two atypical multifunctional cytochromes P450 and a soluble family 1 glycosyltransferase form a metabolon to facilitate channelling of the otherwise toxic and reactive intermediates to the end product in the pathway, the cyanogenic glycoside. The glucosinolate pathway present in Brassicales and the pathway for cyanoalk(en)yl glucoside synthesis such as rhodiocyanosides A and D in Lotus japonicus exemplify how cytochromes P450 in the course of evolution may be recruited for novel pathways. The use of metabolic engineering using cytochromes P450 involved in biosynthesis of cyanogenic glycosides allows for the generation of acyanogenic cassava plants or cyanogenic Arabidopsis thaliana plants as well as L. japonicus and A. thaliana plants with altered cyanogenic, cyanoalkenyl or glucosinolate profiles.Keywords Metabolic engineering AE Metabolons AE CYP79 AE Systems biology AE Plant-insect interactions Cyanogenic glycosides are ancient biomoleculesCyanogenic glycosides (A1) are amino acidderived b-glycosides of a-hydroxynitriles. They have been found in more than 2,650 higher plant

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mentioning

confidence: 99%

Cyanogenic glycosides: a case study for evolution and application of cytochromes P450

Bak¹,

Paquette

Morant³

et al. 2006

Phytochem Rev

123

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“…In previous reports, the co-occurrence of amides and acids with their cyanogenic counterparts has been considered to be a consequence of chemical hydration of the nitrile group to the amide during sample processing (mostly during the drying of plant material), and the structures have been reported as artifacts [43][44][45], although the authors have acknowledged the necessity for enzymatic catalysis of such a reaction [44]. However, Nahrstedt and Rockenbach, who identified prunasin together with prunasin amide in the air-dried leaves of Olinia ventosa, argued that the detected amide was not an artificial product, in view of its high amount and the conservation of its stereochemistry [13].…”

Section: Discussionmentioning

confidence: 99%

A recycling pathway for cyanogenic glycosides evidenced by the comparative metabolic profiling in three cyanogenic plant species

Pičmanová

Neilson

Motawia

et al. 2015

Biochemical Journal

117

126

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N. (2015). A recycling pathway for cyanogenic glycosides evidenced by the comparative metabolic profiling in three cyanogenic plant species. Biochemical Journal, 469(3), 375-389. DOI: 10.1042/BJ20150390 1 A RECYCLING PATHWAY FOR CYANOGENIC GLYCOSIDES EVIDENCED BY THE COMPARATIVE METABOLIC PROFILING IN THREE CYANOGENIC PLANT SPECIES ABSTRACTCyanogenic glycosides are phytoanticipins involved in plant defence against herbivores by virtue of their ability to release toxic HCN upon tissue disruption. In addition, endogenous turnover of cyanogenic glycosides without the liberation of HCN may offer plants an important source of reduced nitrogen at specific developmental stages. To investigate the presence of putative turnover products of cyanogenic glycosides, comparative metabolic profiling using LC-MS/MS and HR-MS complemented by ion-mobility mass spectrometry was carried out in three cyanogenic plant species: cassava, almond and sorghum. In total, the endogenous formation of 36 different chemical structures related to the cyanogenic glucosides linamarin, lotaustralin, prunasin, amygdalin and dhurrin was discovered, including di-and triglycosides derived from these compounds. The relative abundance of the compounds was assessed in different tissues and developmental stages. Based on results common to the three phylogenetically unrelated species, a potential recycling endogenous turnover pathway for cyanogenic glycosides is described in which reduced nitrogen and carbon are recovered for primary metabolism without the liberation of free HCN. Glycosides of amides, carboxylic acids and anitriles derived from cyanogenic glycosides appear as common intermediates in this pathway and may also have individual functions in the plant. The recycling of cyanogenic glycosides and the biological significance of the presence of the turnover products in cyanogenic plants open entirely new insights into the multiplicity of biological roles cyanogenic glycosides may play in plants.Abbreviations: HR-MS, high-resolution mass spectrometry; EIC, extracted ion chromatogram; IM-MS, ionmobility mass spectrometry; ATD, arrival time distribution; CID, collision-induced dissociation 2 SUMMARY STATEMENTA potential recycling pathway for cyanogenic glycosides is presented wherein reduced nitrogen and carbon are recovered for primary metabolism without HCN liberation. Common types of glycosylated pathway intermediates were found in three cyanogenic plant species: cassava, almond and sorghum.

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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: 98%

“…Compound 11 at 32.4 min exhibited a protonated molecule at m/z 304.1 and the molar mass was deduced as 303.1u. Passiguatemalin [1-(β-D-glucopyranosyloxy)-2,3-dihydroxycyclopentene-1-carbonitrile] that possess molecular formula C 12 O 8 H 19 N and molar mass 305 u was isolated from P. guatemalensis (Jaroszewski et al, 2002). 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.…”

Section: Passiflora Quadrangularismentioning

confidence: 99%

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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Cyanohydrin glycosides of Passiflora: distribution pattern, a saturated cyclopentane derivative from P. guatemalensis, and formation of pseudocyanogenic α-hydroxyamides as isolation artefacts

Cited by 38 publications

References 36 publications

Cyanogenic glycosides: a case study for evolution and application of cytochromes P450

Cyanogenic glycosides: a case study for evolution and application of cytochromes P450

A recycling pathway for cyanogenic glycosides evidenced by the comparative metabolic profiling in three cyanogenic plant species

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

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