Antialgal compounds from zantedeschia aethiopica

Greca, Marina Della; Ferrara, Maria; Fiorentino, Antonio; Monaco, Pietro; Previtera, Lucio

doi:10.1016/s0031-9422(98)00092-2

Cited by 127 publications

(46 citation statements)

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“…The antialgal allelochemicals isolated from Myriophyllum spicatum were ellagic, gallic, and pyrogallic acids and (ϩ)-catechin (organic acids) (26). Antialgal phenols and polyphenols were isolated from Zantedeschia aethiopica (12). EMA was isolated as an ester in the present study, making this the first report of EMA as an antialgal allelochemical.…”

Section: Discussionsupporting

confidence: 48%

Isolation and Characterization of a Novel Antialgal Allelochemical from Phragmites communis

2005

Appl Environ Microbiol

188

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Antialgal allelochemicals were isolated from Phragmites communis Tris. The isolated allelopathic fraction showed strong inhibition activity on the growth of Chlorella pyrenoidosa and Microcystis aeruginosa but had no inhibition on Chlorella vulgaris. The 50% effective concentrations (EC 50 ) of the allelopathic fractions on C. pyrenoidosa and M. aeruginosa were 0.49 and 0.79 mg/liter, respectively. The allelopathic activity of the fraction was species-specific. The isolated allelopathic fraction caused metal ion leakage from algal cells. The fraction decreased the activities of antioxidant enzymes, such as superoxide dismutase and peroxidase. The addition of the isolated fraction increased the concentration of unsaturated lipid fatty acids in cell membrane of C. pyrenoidosa and M. aeruginosa. This caused a change in plasma membrane integrity and the leakage of ions in the protoplast. The allelopathic compound was identified by nuclear magnetic resonance and gas chromatography-mass spectrometry as ethyl 2-methylacetoacetate. Synthesized ethyl 2-methylacetoacetate also showed allelopathic activity on C. pyrenoidosa and M. aeruginosa. The EC 50 of synthesized ethyl 2-methylacetoacetate on C. pyrenoidosa and M. aeruginosa were 0.49 and 0.65 mg/liter, respectively.

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Section: Discussionsupporting

confidence: 48%

Isolation and Characterization of a Novel Antialgal Allelochemical from Phragmites communis

2005

Appl Environ Microbiol

188

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“…Together, these results question whether the G glycerol units are solely due to oxidation. Alternatively, guaiacylglycerol might be synthesized intracellularly, as it was isolated as only one enantiomeric form, the D-threo-isomer, from Zantedeschia aethiopica (Della Greca et al, 1998), and guaiacylglycerol glucosides were detected in leaves of Juniperus phoenicea (Comte et al, 1997), in roots and rhizomes of Sinopodophyllum emodi (Zhao et al, 2001), in stems of Hydnocarpus annamensis (Shi et al, 2006) and Xylosma controversum (Xu et al, 2008), and in leaves and branches of Camellia amplexicaulis (Tung et al, 2009). …”

Section: Discussionmentioning

confidence: 99%

Mass Spectrometry-Based Sequencing of Lignin Oligomers

Morreel

Dima²,

Kim³

et al. 2010

Plant Physiol.

171

213

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Although the primary structure of proteins, nucleic acids, and carbohydrates can be readily determined, no sequencing method has been described yet for the second most abundant biopolymer on earth (i.e. lignin). Within secondary-thickened plant cell walls, lignin forms an aromatic mesh arising from the combinatorial radical-radical coupling of monolignols and many other less abundant monomers. This polymerization process leads to a plethora of units and linkage types that affect the physicochemical characteristics of the cell wall. Current methods to analyze the lignin structure focus only on the frequency of the major monomeric units and interunit linkage types but do not provide information on the presence of less abundant unknown units and linkage types, nor on how linkages affect the formation of neighboring linkages. Such information can only be obtained using a sequencing approach. Here, we describe, to our knowledge for the first time, a sequencing strategy for lignin oligomers using mass spectrometry. This strategy was then evaluated on the oligomers extracted from wild-type poplar (Populus tremula 3 Populus tremuloides) xylem. In total, 134 lignin trimers to hexamers were observed, of which 36 could be completely sequenced. Interestingly, based on molecular mass data of the unknown monomeric and dimeric substructures, at least 10 unknown monomeric units or interunit linkage types were observed, one of which was identified as an arylglycerol end unit.Lignin is an aromatic heteropolymer that is mainly present in secondary-thickened plant cell walls, allowing the transport of water and nutrients and providing the necessary strength for the plant to grow upwardly Vanholme et al., 2008Vanholme et al., , 2010. In angiosperms, lignin is predominantly composed of guaiacyl (G) and syringyl (S) units that are derived from combinatorial radical-radical coupling of the monolignols coniferyl and sinapyl alcohol, respectively Fig. 1A). Following oxidation of the monolignols by peroxidase and/or laccase, the resulting electron-delocalized radical has unpaired electron density at its 1-, 3-, O-4-, 5-, and 8-positions (Fig. 1B); note that much of the lignin literature uses Greek letters for the side chain, a, b, and g for the 7-, 8-, and 9-positions. As radical coupling at the 8-position is favored, coupling with another monolignol radical affords, after rearomatization, a mixture of dehydrodimers with 8-8-, 8-5-, and 8-O-4-linkages (Fig. 1C). Following dimerization, polymerization will continue by the coupling of the 8-position of an incoming monolignol radical to the O-4-position of the dimer's phenolic end. In the case of a G dimer, coupling can also occur, albeit at a lower frequency, to the 5-position. Thus, chain elongation creates 8-5-and 8-O-4-linkages (Adler, 1977). Besides the monolignols and other monomers that are present in minor amounts , the plasticity of lignin polymerization permits the incorporation of any phenolic that enters the lignification site, subject to its chemical cross-coupling propensit...

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“…By comparison of their spectral data ( 1 H-, 13 C-NMR and MS) with that reported in the literature, compounds 1-5 and 7-10 were identified as 3-caffeoylquinic acid (1) [4], methyl 4-caffeoylquinic acid (2) [5], methyl 5-caffeoylquinic acid (3) [6], 4-hydroxybenzoic acid (4) [7], syringin (5) [8], amarantholidoside II (7) [9], (-)-oplopan-4-one-10- The spectral data all suggested that 6 was a nerolidol type sesquiterpene glycoside [9]. This was confirmed by the enzymatic hydrolysis of 6, which afforded 6a and a sugar component, which accounted for the last degree of unsaturation.…”

Section: Resultsmentioning

confidence: 89%