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.
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.
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,
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.
A Thorough Study on the Photoisomerization of Ferulic Acid Derivatives
Moni, Lisa,Banfi, Luca,Basso, Andrea,Mori, Alessia,Risso, Federica,Riva, Renata,Lambruschini, Chiara
, p. 1737 - 1749 (2021/03/23)
A thorough study on the (E) to (Z) photoisomerization of ferulic acid derivatives (esters, amides of all types, and ketones) was carried out. At the photostationary state, only aliphatic or benzylic tertiary amides reach a nearly complete conversion of (E) isomers into the (Z) ones, whereas for esters, primary and secondary amides or aromatic tertiary amides mixtures of (Z)/(E) ranging from 7 : 93 to 72 : 28 are observed. Ketones show rather limited photoisomerization. However, (Z) ketones may be obtained by the reaction of organometal compounds with an isomerized (Z) Weinreb amide.
Piperazine-containing ferulic acid derivative Preparation method and application thereof
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Paragraph 0062-0064, (2021/10/05)
The invention discloses a piperazine-containing ferulic acid derivative and a preparation method and application thereof, belongs to the technical field of drug synthesis and agricultural disease prevention and control and is shown in the formula R as follows. 1 Is ethyl, allyl, isopropyl, propynyl, benzyl, o-methylbenzyl, m-methylbenzyl, o-fluorobenzyl. R2 Is ethylsulfonyl. 4 -methylbenzenesulfonyl, 4 -nitrosyl, 4 -trifluoromethylbenzenesulfonyl, 4 -fluorobenzoyl, 2-bromo 5 -trifluoromethylbenzenesulfonyl, 4 -methoxybenzyl, 4 -3 - 3 -trifluorobut 4 -yl, 2 -methoxy 4 -methoxyethyl, 5 -oxo 4 -2 - 2 - 2 - phenylethyl, and the like are described in more detail below in the scope 4 - of the present invention 3.4 4 -3 -1 - 2 -2 . The pharmaceutical molecules have strong activity, and the inhibitory activity on TMV and CMV is remarkable. The structure is derived from natural products and is environment-friendly. And degradation are easy, the preparation process is simple, safe and physicochemical properties are relatively stable.