Identification of (R)-Vicianin in Davallia trichomanoides Blume

Lizotte, Pauline A.; Poulton, Jonathan E.

doi:10.1515/znc-1986-1-202

Cited by 12 publications

(9 citation statements)

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“…The chemical shifts and assignments of 'H-and I3C-NMR analysis of the cyanogenic glycoside isolated from P. aureum are identical with those reported for vicianin isolated from the fern Davallia trickomanoides by Lizotte and Poulton (1985). These data were confirmed by correlated spectroscopy spectra.…”

Section: Results a N D Dlscusslon Ldentification Of (R)-vicianinsupporting

confidence: 76%

Purification and Characterization of a Novel (R)-Mandelonitrile Lyase from the Fern Phlebodium aureum

et al. 1995

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Using high-performance liquid chromatography and nuclear magnetic resonance we identified vicianin as the cyanogenic compound of Phlebodium aureum. The (R)-hydroxynitrile lyase involved during cyanogenesis in the catabolism of the aglycon ([RI-mandelonitrile) was purified to apparent homogeneity. The purified holoenzyme is a homomultimer with subunits of M, = 20,000. At least three isoforms of the enzyme exist. In contrast to other hydroxynitrile lyases, mandelonitrile lyase (MDL) from P. aureum was not inhibited by sulfhydryl-or hydroxyl-modifying reagents, suggesting a different catalytic mechanism. The enzyme is active over a broad temperature range, with maximum activity between 35 and 50"C, and a p H optimum at 6.5. In contrast to (RI-MDLs isolated from several species of the Rosaceae family, (R)-MDL from f . dureum is not a flavoprotein. The substrate specificity was investigated using immobilized enzyme and diisopropyl ether as solvent. The addition of cyanide to aromatic and heterocyclic carbonyls is catalyzed by this (R)-MDL, whereas aliphatic carbonyls are poorly converted.

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Section: Results a N D Dlscusslon Ldentification Of (R)-vicianinsupporting

confidence: 76%

Purification and Characterization of a Novel (R)-Mandelonitrile Lyase from the Fern Phlebodium aureum

et al. 1995

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“…The recorded percentage of cyanogenic fern species is in line with results from previous fern screens (Nicola L.Harper Gillian A. Cooper-Driver T. Swain, 1976). Across the plant kingdom, 4-5% of the species examined are reported to be cyanogenic (Lizotte et al, 1986; Wajant et al, 1995; Miller et al, 2004; Gleadow et al, 2008), while the proportion of cyanogenic gymnosperms is only 1-2% (Luck et al, 2017).…”

Section: Discussionmentioning

confidence: 99%

“…Ferns are the oldest evolutionary plant group known to synthesize cyanogenic glycosides (Bak et al, 2006), specifically the phenylalanine-derived mono-glucoside prunasin, and di-glycoside vicianin (Schreiner et al, 1984; Lizotte et al, 1986). As CYPs are typically involved in cyanogenic glycoside biosynthesis, this class of natural product provides an excellent system by which to undertake pathway elucidation and the characterization of CYPs in ferns (Møller, 2010; Thodberg et al, 2020).…”

Section: Introductionmentioning

confidence: 99%

The fern CYPome: Fern-specific cytochrome P450 family involved in convergent evolution of chemical defense

Thodberg

Hansen

Takos

et al. 2021

Preprint

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Plant natural products encompass an enormous chemical diversity bearing witness to great molecular innovation that occured throughout land plant evolution. Cytochrome P450 monooxygenases (CYPs) catalyze a wide variety of monooxygenation reactions essential to the metabolic repertoire of plants natural products. Ferns constitute the second largest group of vascular plants and hold a significant phylogenetic position in land evolution, lying sister to seed plants. To date, CYP diversity has not been described for this taxon and pathway discovery in ferns in general is scarce, despite possessing a rich diversity of natural products. We analysed over 8000 available fern CYPs, classifing and characterizing the landscape of this super-enzyme group. Fern CYPs are dominated by fern-specific families (∼60%), with the largest family – CYP981 – constituting approximately 15% of all predicted fern CYPs in the dataset. The abundancy and dynamics of the CYP981 family suggest a position equivalent to the CYP71 family present in seed plants, with potential roles in natural product biosynthesis. Ferns are the evolutionary oldest group to biosynthesize cyanogenic glycosides; amino acid-derived defense compounds. We show that CYP981F5 from the highly cyanogenic fern Phlebodium aureum catalyzes the conversion of phenylacetonitrile to mandelonitrile, an intermediate step in cyanogenic glycoside biosynthesis. The fern CYPome provides an important platform to further understand evolution of metabolite biosynthesis throughout the plant kingdom, and in ferns specifically.

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“…Several types of glycosylation of cyanogenic glucosides have been described in the literature in particular glucosylation [14,32], apiosylation [18,19], arabinosylation [64,68], xylosylation [27,31] and allosylation [69]. It has been proposed that the cyanogenic diglucosides linustatin, neolinustatin, amygdalin and dhurrin-6´-glucoside may function as a protected transport form of their corresponding monoglucosides linamarin, lotaustralin, prunasin and dhurrin, respectively [14,32,36], for the long-distance translocation from the site of their biosynthesis to the sink.…”

Section: Accepted Manuscriptmentioning

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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Identification of (R)-Vicianin in Davallia trichomanoides Blume

Cited by 12 publications

References 0 publications

Purification and Characterization of a Novel (R)-Mandelonitrile Lyase from the Fern Phlebodium aureum

Purification and Characterization of a Novel (R)-Mandelonitrile Lyase from the Fern Phlebodium aureum

The fern CYPome: Fern-specific cytochrome P450 family involved in convergent evolution of chemical defense

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

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