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.
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.
Synthesis of 1,3,4-trisubstituted pyrrolidines as meropenem adjuvants targeting New Delhi metallo-β-lactamase
Jin, Wen Bin,Xu, Chen,Qi, Xiao Lin,Zeng, Ping,Gao, Wei,Lai, Ki Hon,Chiou, Jiachi,Chan, Edward W. C.,Leung, Yun-Chung,Chan, Tak Hang,Wong, Kwok-Yin,Chen, Sheng,Chan, Kin-Fai
supporting information, p. 3515 - 3534 (2021/03/03)
The effective strategies to neutralize the New Delhi metallo-β-lactamase (NDM-1) activity offer unique opportunities to combination therapy because NDM-1 inactivates all classes of carbapenem antibiotics, which are widely regarded as the last resort of drugs for treating serious bacterial infections. Here we describe the efficient construction of a series of trans-1,3,4-trisubstituted pyrrolidines via boric acid-catalyzed 1,3-dipolar cycloaddition of N-benzylazomethine ylide with methyl ferulate for the biological evaluation of their cytotoxicity and synergistic activity in combination with meropenem towards NDM-1 positive carbapenem-resistant Enterobacteriaceae (CRE). The cell-based screens generated one promising hit, namely compound 10e, which exhibited low cytotoxicity (IC50 > 128 μM), moderate NDM-1 enzyme inhibition (IC50 = 51 μM), and potent synergistic activity against a panel of clinically isolated NDM-1 positive CRE with fractional inhibitory concentration indexes ranging from 0.01 to 0.25. Structure-activity relationship studies revealed that the zinc-chelating moiety of 2-(bis(pyridin-2-ylmethyl)-amino)acetyl group of compound 10e plays a pivotal role for potent activity. Regarding the inhibition mechanism, a series of biochemical assays revealed that compound 10e may inactivate NDM-1 activity by displacing both zinc ions from the active site of the enzyme. Altogether, our studies indicate that compound 10e represents an important pyrrolidine-type scaffold targeting NDM-1, providing a promising starting point to be further developed as carbapenem antibiotic adjuvants. This journal is