Rational design, synthesis and biological evaluation of the first inhibitor of lignin polymerization

Daubresse, Nicolas; Chupeau, Yves; Francesch, C.; Lapierre, Catherine; Pollet, Brigitte; Rolando, Christian

doi:10.1039/a702464i

Cited by 25 publications

(10 citation statements)

References 27 publications

(26 reference statements)

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“…Coniferin (Falshaw et al, 1969;Chapela et al, 1991;Daubresse et al, 1997) Xylariaceae sp. 29 Reduced the biosynthesis of lignins via inhibition of oxidases (Continued)…”

Section: Phenylpropanoids and Lignansmentioning

confidence: 99%

Endophytic Fungi: From Symbiosis to Secondary Metabolite Communications or Vice Versa?

et al. 2021

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Endophytic fungi (EF) are a group of fascinating host-associated fungal communities that colonize the intercellular or intracellular spaces of host tissues, providing beneficial effects to their hosts while gaining advantages. In recent decades, accumulated research on endophytic fungi has revealed their biodiversity, wide-ranging ecological distribution, and multidimensional interactions with host plants and other microbiomes in the symbiotic continuum. In this review, we highlight the role of secondary metabolites (SMs) as effectors in these multidimensional interactions, and the biosynthesis of SMs in symbiosis via complex gene expression regulation mechanisms in the symbiotic continuum and via the mimicry or alteration of phytochemical production in host plants. Alternative biological applications of SMs in modern medicine, agriculture, and industry and their major classes are also discussed. This review recapitulates an introduction to the research background, progress, and prospects of endophytic biology, and discusses problems and substantive challenges that need further study.

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“…Coniferin (Falshaw et al, 1969;Chapela et al, 1991;Daubresse et al, 1997) Xylariaceae sp. 29 Reduced the biosynthesis of lignins via inhibition of oxidases (Continued)…”

Section: Phenylpropanoids and Lignansmentioning

confidence: 99%

Endophytic Fungi: From Symbiosis to Secondary Metabolite Communications or Vice Versa?

et al. 2021

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“…There are few syntheses leading directly to the aldehyde, and they use even harsher conditions, which are not compatible with functionalized molecules . We were confronted with this problem during the synthesis the O -glucoside of fluoroconiferyl alcohol, ( Z )-β-fluoroconiferin, a strong inhibitor of lignin polymerization . The final step involves the reduction of the fully protected glucoside ester by NaBH 4 (7.4 equiv), in the presence of LiCl (10 equiv) in glyme (80 °C, 18 h), and leads to a time-consuming purification due to the deprotection of the pentaacetate glucose moiety.…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Stereoconvergent Formylation of (E/Z)-β-Bromo-β-fluorostyrenes: Straightforward Access to (Z)-α-Fluorocinnamic Aldehydes and (Z)-β-Fluorocinnamic Alcohols

et al. 2011

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We report here the stereoconvergent formylation of (E/Z)-β-bromo-β-fluorostyrene mixtures with carbon monoxide and sodium formate catalyzed by palladium. Optimization of reaction conditions leads to the corresponding pure (Z)-α-fluorocinnamaldehydes in good yields. The reaction was extended to styrenes bearing electro-attracting or electro-donating groups. The obtained α-fluoroaldehydes were smoothly reduced to the corresponding (Z)-β-fluorocinnamic alcohol by NaBH(4). The reaction could be performed on functionalized substrates as demonstrated by the access to the glucoside of β-fluoroconiferyl alcohol, (Z)-β-fluoroconiferin, a strong inhibitor of lignin polymerization.

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“…Analogues of retinal, bearing a fluorine atom in vinylic position are important tools for the study of the process of vision [7,8]. The glucoside of coniferyl alcohol, bearing a fluorine atom on the cinnamic alcohol double bond is an inhibitor of lignification [9].…”

Section: Introductionmentioning

confidence: 99%

Regiospecific synthesis of symmetrical (1E,3E) 2,3-difluoro-1,4-diphenyl-buta-1,3-dienes via palladium-catalyzed cross-coupling of (Z) 2-bromo-2-fluoroethenylbenzenes in presence of bis(pinacolato)diboron

Eddarir

Rolando

2004

Journal of Fluorine Chemistry

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Rational design, synthesis and biological evaluation of the first inhibitor of lignin polymerization

Cited by 25 publications

References 27 publications

Endophytic Fungi: From Symbiosis to Secondary Metabolite Communications or Vice Versa?

Endophytic Fungi: From Symbiosis to Secondary Metabolite Communications or Vice Versa?

Palladium-Catalyzed Stereoconvergent Formylation of (E/Z)-β-Bromo-β-fluorostyrenes: Straightforward Access to (Z)-α-Fluorocinnamic Aldehydes and (Z)-β-Fluorocinnamic Alcohols

Regiospecific synthesis of symmetrical (1E,3E) 2,3-difluoro-1,4-diphenyl-buta-1,3-dienes via palladium-catalyzed cross-coupling of (Z) 2-bromo-2-fluoroethenylbenzenes in presence of bis(pinacolato)diboron

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