141632-15-7Relevant articles and documents
Chemical syntheses of caffeoyl and 5-OH coniferyl aldehydes and alcohols and determination of lignin o-methyltransferase activities in dicot and monocot species
Chen, Fang,Kota, Parvathi,Blount, Jack W.,Dixon, Richard A.
, p. 1035 - 1042 (2001)
To investigate the substrate preferences of O-methyltransferases in the monolignol biosynthetic pathways, caffeoyl and 5-hydroxy coniferyl aldehydes were synthesized by a new procedure involving a Wittig reaction with the corresponding hydroxybenzaldehydes. The same procedure can also be used to synthesize caffeoyl and 5-hydroxyconiferyl alcohols. Relative O-methyltransferase activities against these substrates were determined using crude extracts and recombinant caffeic acid O-methyltransferase from alfalfa (Medicago sativa), and crude extracts from the model legume. Medicago truncatula, tobacco, wheat and tall fescue. Extracts from all these species catalyzed methylation of the various monolignol aldehydes and alcohols more effectively than the corresponding hydroxycinnamic acids.
Structure–activity relationship of caffeic acid phenethyl ester analogs as new 5-lipoxygenase inhibitors
Doiron, Jérémie A.,Leblanc, Luc M.,Hébert, Martin J. G.,Levesque, Natalie A.,Paré, Aurélie F.,Jean-Fran?ois, Jacques,Cormier, Marc,Surette, Marc E.,Touaibia, Mohamed
, p. 514 - 528 (2017/04/06)
Leukotrienes (LTs) are a class of lipid mediators implicated in numerous inflammatory disorders. Caffeic acid phenethyl ester (CAPE) possesses potent anti-LTs activity through the inhibition of 5-lipoxygenase (5-LO), the key enzyme in the biosynthesis of LTs. In this study, we describe the design and synthesis of CAPE analogs as radical scavengers and 5-LO inhibitors. Caffeic esters bearing propargyl and allyl linkers between the caffeoyl and aryl moieties (4a–i and 5a–i, respectively) were synthesized by Sonogashira and Heck cross-coupling reactions to probe the effects of flexibility and aryl substitution on 5-LO inhibition. Caffeoyl alcohol and ethers (6, 7a–b) as well as caffeoyl aldehyde and ketones (8a–e) were synthesized to elucidate the importance of the ester linkage for inhibitory activity. All tested compounds proved to be good radical scavengers (IC50 of 10–30?μm). After preliminary anti-LTs activity screening in HEK293 cell models, 5-LO inhibition potential of selected compounds was determined in human polymorphonuclear leukocytes (PMNL). Most screened compounds outperformed CAPE 3 in concentration-dependent assays on PMNL, with ester dimers 4i and 5i along with caffeoyl ethers 7a–b being roughly eight-, seven-, and 16-fold more potent than Zileuton, with IC50 values of 0.36, 0.43, and 0.18?μm, respectively.
PROCESS FOR THE PREPARATION OF CINNAMALDEHYDE COMPOUNDS
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Page 24; 25, (2010/02/10)
A process for the preparation of cinnamaldehyde, a,?-unsaturated cyanoester, and cyanoamide compounds using a Heck reaction is described. Methods for further elaboration of these aldehydes are also provided.
