125874-72-8Relevant academic research and scientific papers
Quinoid glycosides from Forsythia suspensa
Li, Chang,Dai, Yi,Zhang, Shu-Xiang,Duan, Ying-Hui,Liu, Ming-Li,Chen, Liu-Yuan,Yao, Xin-Sheng
, p. 105 - 113 (2014)
Phytochemical investigation on Forsythia suspensa (Thunb.) Vahl afforded 10 compounds, including quinoid glycosides, lignan glycosides, phenylethanoid glycoside and allylbenzene glycoside together with 13 known ones. Their structures were established based on extensive spectroscopic data analyses, including IR, UV, HRESIMS, 1D NMR and 2D NMR. Absolute configurations were determined by ECD calculation method and chemical degradation. In addition, all compounds were evaluated for their antiviral activity against influenza A (H1N1) virus and several were further evaluated against respiratory syncytial virus (RSV) in vitro. Among them, two previously known compounds showed significant activities against RSV with EC50 values of 3.43 and 6.72 μM.
Isolation of neoanisatin derivatives from the pericarps of Illicium majus with other constituents
Kouno,Hashimoto,Enjoji,Takahashi,Kaneto,Yang
, p. 1773 - 1778 (1991)
Further studies on the constituents of Illicum majus have resulted in the isolation of five new neoanisatin derivatives and two known phytoquinoides together with two known neolignans. Two of the neoanisatin derivatives are 1-hydroxyl, which are the first examples isolated anisatin derivatives so far. Another one, 2-oxoneoanisatin, exhibited picrotoxin-like convulsions in mice, the same as anisatin. The other two 3,4-dehydro-2-oxoneoanisatin isomers could not be separated from each other, even with high performance liquid chromatography.
Kinetic resolution of a dihydrobenzofuran-type neolignan by lipase-catalysed acetylation
Van Dyck, Stefaan M.O.,Lemiere, Guy L.F.,Jonckers, Tim H.M.,Dommisse, Roger,Pieters, Luc,Buss, Volker
, p. 785 - 789 (2001)
The kinetic resolution of 3,5′-dimethoxy-4′,7-epoxy-8,3′-neolignane-4,9,9′- triol 1 by lipase-catalysed acetylation in an organic solvent was investigated. Ten different lipases were screened for enantioselectivity in the reaction. The enantiomeric excess (e.e.) of the products was strongly dependent on the type of lipase used. After optimisation of the reaction conditions for Candida cylindracea lipase, the e.e. and yield of the reaction was improved greatly and, in some cases, the enantiomerically pure starting material 1 could be isolated, albeit in a low yield, with the acetylation affording predominantly (2R,3S)-1 and the (2S,3R)-esters.
Neolignans from Red Raspberry (Rubus idaeus L.) Exhibit Enantioselective Neuroprotective Effects against H2O2-Induced Oxidative Injury in SH-SY5Y Cells
Zhou, Le,Yao, Guo-Dong,Lu, Li-Wei,Song, Xiao-Yu,Lin, Bin,Wang, Xiao-Bo,Huang, Xiao-Xiao,Song, Shao-Jiang
, p. 11390 - 11397 (2018)
Red raspberry has been well-known for its nutritional purpose. Although this fruit has been reported for its potent antioxidant activity and health-promoting properties, systematic studies responsible for the bioactive constituents were still insufficient. In the current study, three pairs of dihydrobenzofuran-type enantiomeric neolignans (1a/1b-3a/3b), including two new compounds (1b and 2a), were isolated from the fruit of Rubus idaeus. The structures of these enantiomers were determined through spectroscopic methods and quantum mechanical calculations. Biologically, enantiomers 2a and 2b exhibited significant enantioselective protective effects against H2O2-induced neurotoxicity at 50 μM (2a, 86.72 ± 1.17%; 2b, 69.70 ± 1.59%). The underlying mechanism study demonstrated that enantiomer 2a is able to attenuate H2O2-induced apoptosis, reactive oxygen species (ROS) generation, and mitochondrial dysfunction in SH-SY5Y cells. Overall, these findings provide a valuable foundation for the understanding of neuroprotective activities of red raspberry and further investigation on its potential application values.
Characterization and identification of bioactive polyphenols in the trapa bispinosa roxb. Pericarp extract
Ganeko, Natsuki,Hayakawa, Chisa,Ito, Hideyuki,Iwaoka, Yuji,Kato, Nana,Kawabe, Satoko,Suzuki, Shoichi,Uemura, Tomohiro
, (2021/09/28)
In this study, we present the isolation and characterization of the structure of six gallotan-nins (1–6), three ellagitannins (7–9), a neolignan glucoside (10), and three related polyphenolic compounds (gallic acid, 11 and 12) from Trapa bispinosa Roxb. pericarp extract (TBE). Among the isolates, the structure of compound 10 possessing a previously unclear absolute configuration was unam-biguously determined through nuclear magnetic resonance and circular dichroism analyses. The α-glucosidase activity and glycation inhibitory effects of the isolates were evaluated. Decarboxylated rugosin A (8) showed an α-glucosidase inhibitory activity, while hydrolyzable tannins revealed stronger antiglycation activity than that of the positive control. Furthermore, the identification and quantification of the TBE polyphenols were investigated by high-performance liquid chromatog-raphy coupled to ultraviolet detection and electrospray ionization mass spectrometry analysis, in-dicating the predominance of gallic acid, ellagic acid, and galloyl glucoses showing marked anti-glycation properties. These findings suggest that there is a potential food industry application of polyphenols in TBE as a functional food with antidiabetic and antiglycation activities.
Sesquineolignan and neolignan enantiomers from Triadica sebifera
Liu, Jin-Long,Wang, Su-Juan,Yu, Min,Zhang, Gui-Jie,Zhang, Yong-Li
, (2020/08/06)
Two pairs of new sesquineolignan enantiomers (1a/1b and 1c/1d), two pair of new 4′,7-epoxy-8,3′-neolignan enantiomers (2a/2b and 3a/3b), and a pair of new 3′,7-epoxy-8,4′-oxyneolignan enantiomers (4a/4b), along with two pairs of known 4′,7-epoxy-8,3′-neol
Comparative analysis of stilbene and benzofuran neolignan derivatives as acetylcholinesterase inhibitors with neuroprotective and anti-inflammatory activities
Nagumo, Mina,Ninomiya, Masayuki,Oshima, Natsuko,Itoh, Tomohiro,Tanaka, Kaori,Nishina, Atsuyoshi,Koketsu, Mamoru
, p. 2475 - 2479 (2019/07/30)
Stilbenes and benzofuran neolignans are important groups of plant phenolics therefore they play a significant role in plants and human health. The objective of this study was to investigate the structure-activity relationships of naturally occurring stilbene and benzofuran neolignan derivatives as acetylcholinesterase inhibitors. A series of these compounds were prepared and assessed for their inhibition on acetylcholinesterase activity. δ-Viniferin, pterostilbene trans-dehydrodimer, pallidol, grossamide, and boehmenan exerted acetylcholinesterase inhibitory potential. The several oligomeric compounds protected against cell damage resulting from t-BHP exposure and inhibited lipopolysaccharide/interferon-gamma (LPS/IFNγ)-induced NO production in vitro. Our findings highlight the great potential of pterostilbene trans-dehydrodimer, pallidol, and boehmenan as multifunctional nutraceuticals for management of neurodegenerative diseases.
Neolignan Constituents with Potential Beneficial Effects in Prevention of Type 2 Diabetes from Viburnum fordiae Hance Fruits
Zhao, Chunchao,Chen, Jia,Shao, Jianhua,Shen, Jie,Li, Kehuan,Gu, Wenyan,Li, Sihui,Fan, Judi
, p. 10421 - 10430 (2018/10/15)
Nine new neolignan glycosides (1-9), viburfordosides A-I, two new neolignans, fordianes A and B (10, 11), and seven known analogues (12-18) have been isolated and identified from the fruits of Viburnum fordiae Hance. The structures and absolute configurations of undescribed neolignan constituents were identified by chemical methods and spectroscopic analyses. The α-glucosidase inhibitory, ABTS?+ and DPPH? scavenging, and anti-inflammatory activities of these secondary metabolites were evaluated. Some of them exhibited significant potency in inhibiting α-glucosidase and scavenging free radicals. Among the 14 metabolites that were found to have the capacity to inhibit NO production in LPS-stimulated RAW264.7 macrophage cells, compounds 2, 4, 6, 10, 11, 14, 17, and 18 were potent with IC50 values of 10.88-41.10 μM. These results support that V. fordiae fruits possessing the neolignan compounds may serve as both a functional food and a medicinal resource to prevent and treat type 2 diabetes (T2D).
A diastereoselective route to trans-2-aryl-2,3-dihydrobenzofurans through sequential cross-metathesis/isomerization/allylboration reactions: Synthesis of bioactive neolignans
Hemelaere, Rémy,Carreaux, Fran?ois,Carboni, Bertrand
, p. 2470 - 2481 (2015/04/22)
A new highly diastereoselective synthetic route to trans-2,3-dihydrobenzofuran systems, in particular those bearing an aryl substituent at the C2 position, is described. The cornerstone of our strategy is the implementation of a cross-metathesis/isomerization/allylboration sequence starting from 2-allyl-substituted phenols and aldehydes. After an intramolecular Mitsunobu cyclization step, the anti-homoallylic alcohols allow the synthesis of the desired skeleton in a stereoselective fashion. As an illustration, we used this strategy for the preparation of the dihydrodehydrodiconiferyl alcohol (1a), a natural dihydrobenzofuran neolignan, as well as for a formal synthesis of its O-demethylated derivative 1b. An enantioselective version of this approach employing a chiral phosphoric acid in the allylboration step is also studied.
Bioactive lignans from the Trunk of Abies holophylla
Kim, Chung Sub,Kwon, Oh Wook,Kim, Sun Yeou,Lee, Kang Ro
, p. 2131 - 2135 (2014/01/06)
Six new lignans (1-6) were isolated from the trunk of Abies holophylla MAXIM, together with 11 known lignans (7-17). The structures of 1-7 were elucidated by spectroscopic methods, acid hydrolysis, and use of the modified Mosher's method. The effects of the isolates on nerve growth factor induction in a C6 rat glioma cell line were evaluated. Compounds 6, 7, and 13 showed significant induction of nerve growth factor secretion at concentrations of 10 μM. Compounds 1, 5, 6, and 16 showed moderate inhibitory effects on nitric oxide production in lipopolysaccharide-activated BV-2 cells (IC50 28.5-36.4 μM).
