2309-07-1Relevant articles and documents
Firmosides A and B: two new sucrose ferulates from the aerial parts of Silene firma and evaluation of radical scavenging activities
Uyen, Nguyen Hoang,Widyowati, Retno,Sulistyowaty, Melanny Ika,Sugimoto, Sachiko,Yamano, Yoshi,Kawakami, Susumu,Otsuka, Hideaki,Matsunami, Katsuyoshi
, p. 796 - 803 (2020)
Abstract: Two new tri-ferulates of sucrose, firmosides A and B (1 and 2, respectively), together with 18 known compounds (3–20), were isolated from the aerial parts of Silene firma. The structures of the isolated compounds were elucidated by various spectroscopic methods, including 1D, 2D NMR, and high-resolution electro-spray ionization–mass spectrometry (HR-ESI–MS). All the isolated compounds were evaluated for their free radical scavenging activity using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical. As a result, two new compounds (1, 2) and 11 demonstrated significant radical scavenging activity, implying the usefulness as antioxidant agents. Graphic Abstract: [Figure not available: see fulltext.].
Chemoprotective properties of phenylpropenoids, bis(benzylidene)cycloalkanones, and related Michael reaction acceptors: Correlation of potencies as phase 2 enzyme inducers and radical scavengers
Dinkova-Kostova, Albena T.,Abeygunawardana, Chitrananda,Talalay, Paul
, p. 5287 - 5296 (1998)
Induction of phase 2 enzymes (e.g., glutathione transferases, NAD(P)H:quinone reductase, glucuronosyltransferases, epoxide hydrolase) is a major strategy for reducing the susceptibility of animal cells to neoplasia and other forms of electrophile toxicity. In a search for new chemoprotective enzyme inducers, a structure-activity analysis was carried out on two types of naturally occurring and synthetic substituted phenylpropenoids: (a) Ar- CH=CH-CO-R, where R is OH, OCH3, CH3, or Ar, including cinnamic, coumaric, ferulic, and sinapic acid derivatives, their ketone analogues, and chalcones; and (b) bis(benzylidene)cycloalkanones, Ar-CH=C(CH2)(n)(CO)C=CH-Ar, where n = 5, 6, or 7. The potencies of these compounds in inducing NAD(P)H:quinone reductase activity in murine hepatoma cells paralleled their Michael reaction acceptor activity (Talalay, P.; De Long, M. J.; Prochaska, H. J. Proc. Natl. Acad. Sci. U.S.A. 85, 1988, 8261-8265). Unexpectedly, the bis(benzylidene)cycloalkanones also powerfully quenched the lucigenin- derived chemiluminescence evoked by superoxide radicals. Introduction of o- hydroxyl groups on the aromatic rings of these phenylpropenoids dramatically enhanced their potencies not only as inducers for quinone reductase but also as quenchers of superoxide. These potentiating o-hydroxyl groups are hydrogen-bonded, as shown by moderate down field shift of their proton NMR resonances and their sensitivities to the solvent environment. The finding that the potencies of a series of bis(benzylidene)cycloalkanones in inducing quinone reductase appear to be correlated with their ability to quench superoxide radicals suggests that the regulation of phase 2 enzymes may involve both Michael reaction reactivity and radical quenching mechanisms.
A convenient synthesis of (±)-3-methoxybenzodioxane-4,9,9'-triol neolignan, and methyl ethers of isoamericanol A and isoamericanin A
She, Xuegong,Gu, Wenxin,Wu, Tongxing,Pan, Xinfu
, p. 100 - 101 (1999)
The (±)-3-methoxybenzodioxane-4,9,9'-triol neolignan 9, and methyl ethers of isoamericanol A 8 and isoamericanin A 7 were synthesized from the readily available materials caffeic acid and ferulic acid, using a coupling reaction as a key step.
Structure of Three Diacylated Anthocyanins Isolated from Red Cabbage, Brassica oleracea
Idaka, Eiichi,Yamakita, Hiroshi,Ogawa, Toshihiko,Kondo, Tadao,Yamamoto, Manabu,Goto, Toshio
, p. 1213 - 1216 (1987)
Three diacylated anthocyanins were isolated from Brassica oleracea and their structures determined to be 3-O-(6-O-acyl-2-O-(2-O-sinapyl-β-D-glucopyranosyl)-β-D-glucopyranosyl)-β-D-glucopyranosyl)-5-O-(β-D-glucopyranosyl)cyanidins, in wich the acyl groups were p-coumaryl, ferulyl, and sinapyl, respectively.
IN VITRO PEROXIDASE-CATALYSED OXIDATION OF FERULIC ASID ESTERS
Wallace, Graham,Fry, Stephen C.
, p. 1293 - 1300 (1995)
Methyl ferulate, a model feruloyl ester, was reacted with H2O2 and peroxidase in order to simulate the possible fate of such esters in the primary cell wall.The major dimeric product was identified as a cyclic dimer with a β-5 linkage and an α-O-4-linkage.This compound, which exceeded the yield of 5,5'-dehydrodiferulic acid dimethyl ester, could arise by nucleophilic substitution of an intermediary β-5 quinone methide with the neighbouring phenolic hydroxyl group.Inclusion in the reaction mixture of high concentrations of sugars as alternative nucleophiles, such as would occur in the plant cell wall, resulted in very little or no bonding of aromatic material to the sugar.In contrast to these in vitro findings, 5,5'-dehydrodiferulate is the only oxidatively-coupled dimer of ferulate to have been reported in vivo, the apparent formation of ether bonds between ferulate oxidation products and cell wall polysaccharides has been reported.Mechanisms are proposed which may facilitate bonding of ferulate-derived quinone methides to carbohydrates in vivo. - Key words: methyl ferulate; peroxidase; oxidation; plant cell walls.
Flavonoid glycosides from the leaves of Allium victorialis var. platyphyllum and their anti-neuroinflammatory effects
Woo, Kyeong Wan,Moon, Eunjung,Park, So Young,Kim, Sun Yeou,Lee, Kang Ro
, p. 7465 - 7470 (2012)
Eight new flavonoid glycosides, named allivictoside A-H (1-8), together with twelve known flavonoids (9-20) were isolated from the leaves of Allium victorialis var. platyphyllum. The structures of 1-8 were determined by chemical and spectroscopic methods,
Anti-inflammatory and antitumor phenylpropanoid sucrosides from the seeds of Raphanus sativus
Kim, Ki Hyun,Kim, Chung Sub,Park, Yong Joo,Moon, Eunjung,Choi, Sang Un,Lee, Jei Hyun,Kim, Sun Yeou,Lee, Kang Ro
, p. 96 - 99 (2014)
A bioassay-guided fractionation and chemical investigation of the MeOH extract of Raphanus sativus seeds resulted in the isolation and identification of eight phenylpropanoid sucrosides (1-8) including two new compounds, named raphasativuside A and B (1-2) from the most active CHCl3-soluble fraction. The structures of these new compounds were elucidated through spectral analysis, including extensive 2D-NMR data, and chemical reaction experiments. We evaluated the anti-inflammatory effects of 1-8 in lipopolysaccharide (LPS)-stimulated murine microglia BV2 cells. Compounds 2 and 5 exhibited significant inhibitory effect on nitric oxide production in LPS-activated BV-2 cells with IC50 values of 21.63 and 26.96 μM, respectively. All isolates were also evaluated for their antiproliferative activities against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15). Compounds 1-7 showed consistent cytotoxicity against A549, SK-OV-3, SK-MEL-2, and HCT-15 cell lines with IC50 values of 6.71-27.92 μM. Additionally, the free-radical scavenging activity of 1-8 was assessed using the DPPH (2,2-diphenyl-1-picrylhydrazyl) assay where compounds 1, 3, and 4 scavenged DPPH radical strongly with IC50 values of 23.05, 27.10, and 29.63 μg/mL, respectively.
A new approach for synthesis of erythro 8-0-4′ neolignans
Chen, XiaoChuan,Gu, WenXin,Jing, XiaoBi,Pan, XinFu
, p. 557 - 564 (2002)
Erythro- 1-(4-hydroxy-3-methoxyphenyl)-2- (4-formyl-2-methoxy-phenoxy)-propane-1,3-diol, a 8-0-4′ norneolignan, has been stereoselectively synthesized in eight steps from ferulic acid. In this new route to prepare erythro 8-0-4′ neolignans the cis addition of mCPBA to a double bond with high regioselectivity was a key step, and its mechanism is discussed.
Photoinduced Regioselective Olefination of Arenes at Proximal and Distal Sites
Ali, Wajid,Anjana, S. S.,Bhattacharya, Trisha,Chandrashekar, Hediyala B.,Goswami, Nupur,Guin, Srimanta,Maiti, Debabrata,Panda, Sanjib,Prakash, Gaurav,Saha, Argha,Sasmal, Sheuli,Sinha, Soumya Kumar
supporting information, p. 1929 - 1940 (2022/02/01)
The Fujiwara-Moritani reaction has had a profound contribution in the emergence of contemporary C-H activation protocols. Despite the applicability of the traditional approach in different fields, the associated reactivity and regioselectivity issues had
Prenylated trans-cinnamic esters and ethers against clinical fusarium spp.: Repositioning of natural compounds in antimicrobial discovery
Balmas, Virgilio,Carta, Paola,Casalini, Stefano,Chtioui, Wiem,Delogu, Giovanna,Dettori, Maria A.,Fabbri, Davide,Migheli, Quirico,Oufensou, Safa
, (2021/06/14)
Onychomycosis is a common nail infection mainly caused by species belonging to the F. oxysporum, F. solani, and F. fujikuroi species complexes. The aim of this study was to evaluate the in vitro susceptibility of six representative strains of clinically relevant Fusarium spp. toward a set of natural-occurring hydroxycinnamic acids and their derivatives with the purpose to develop naturally occurring products in order to cope with emerging resistance phenomena. By introducing a prenylated chain at one of the hydroxy groups of trans-cinnamic acids 1–3, ten prenylated derivatives (coded 4–13) were preliminarily investigated in solid Fusarium minimal medium (FMM). Minimal inhibitory concentration (MIC) and lethal dose 50 (LD50) values were then determined in liquid FMM for the most active selected antifungal p-coumaric acid 3,3′-dimethyl allyl ester 13, in comparison with the conventional fungicides terbinafine (TRB) and amphotericin B (AmB), through the quantification of the fungal growth. Significant growth inhibition was observed for prenylated derivatives 4–13, evidencing ester 13 as the most active. This compound presented MIC and LD50 values (62–250 μM and 7.8–125 μM, respectively) comparable to those determined for TRB and AmB in the majority of the tested pathogenic strains. The position and size of the prenylated chain and the presence of a free phenol OH group appear crucial for the antifungal activity. This work represents the first report on the activity of prenylated cinnamic esters and ethers against clinical Fusarium spp. and opens new avenues in the development of alternative antifungal compounds based on a drug repositioning strategy.
