- Characterization and identification of bioactive polyphenols in the trapa bispinosa roxb. Pericarp extract
-
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.
- Ganeko, Natsuki,Hayakawa, Chisa,Ito, Hideyuki,Iwaoka, Yuji,Kato, Nana,Kawabe, Satoko,Suzuki, Shoichi,Uemura, Tomohiro
-
-
- Sesquineolignan and neolignan enantiomers from Triadica sebifera
-
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
- Liu, Jin-Long,Wang, Su-Juan,Yu, Min,Zhang, Gui-Jie,Zhang, Yong-Li
-
-
- Comparative analysis of stilbene and benzofuran neolignan derivatives as acetylcholinesterase inhibitors with neuroprotective and anti-inflammatory activities
-
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.
- Nagumo, Mina,Ninomiya, Masayuki,Oshima, Natsuko,Itoh, Tomohiro,Tanaka, Kaori,Nishina, Atsuyoshi,Koketsu, Mamoru
-
p. 2475 - 2479
(2019/07/30)
-
- Neolignans from Red Raspberry (Rubus idaeus L.) Exhibit Enantioselective Neuroprotective Effects against H2O2-Induced Oxidative Injury in SH-SY5Y Cells
-
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.
- 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
(2018/11/20)
-
- Neolignan Constituents with Potential Beneficial Effects in Prevention of Type 2 Diabetes from Viburnum fordiae Hance Fruits
-
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).
- Zhao, Chunchao,Chen, Jia,Shao, Jianhua,Shen, Jie,Li, Kehuan,Gu, Wenyan,Li, Sihui,Fan, Judi
-
p. 10421 - 10430
(2018/10/15)
-
- Quinoid glycosides from Forsythia suspensa
-
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.
- Li, Chang,Dai, Yi,Zhang, Shu-Xiang,Duan, Ying-Hui,Liu, Ming-Li,Chen, Liu-Yuan,Yao, Xin-Sheng
-
p. 105 - 113
(2014/06/23)
-
- Bioactive lignans from the Trunk of Abies holophylla
-
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).
- Kim, Chung Sub,Kwon, Oh Wook,Kim, Sun Yeou,Lee, Kang Ro
-
p. 2131 - 2135
(2014/01/06)
-
- Justicia lignans: Part 10-Synthesis of tiruneesiin, the first neolignan from Justicia species
-
(±)-Tiruneesiin, 3-[2-(4-hydroxy-3-methoxyphenyl)-3-acetoxymethyl-7- methoxy-2, 3-dihydro-1-benzofuran-5-yl]propan-1-yl acetate 1, is synthesized starting from methyl ferulate 2 with an overall yield of 12.6%. Ag2O induced dimerization of 2 is
- Subbaraju, Gottumukkala V.,Kavitha, Jakka,Rajasekhar, Dodda,Hsu, Feng-Lin,Cheng, Kur-Ta
-
p. 357 - 359
(2008/03/27)
-
- Pinus taeda phenylpropenal double-bond reductase: Purification, cDNA cloning, heterologous expression in Escherichia coli, and subcellular localization in P. taeda
-
A phenylpropenal double-bond reductase (PPDBR) was obtained from cell suspension cultures of loblolly pine (Pinus taeda L.). Following trypsin digestion and amino acid sequencing, the cDNA encoding this protein was subsequently cloned, with the functional recombinant protein expressed in Escherichia coli and characterized. PPDBR readily converted both dehydrodiconiferyl and coniferyl aldehydes into dihydrodehydrodiconiferyl and dihydroconiferyl aldehydes, when NADPH was added as cofactor. However, it was unable to reduce directly either the double bond of dehydrodiconiferyl or coniferyl alcohols in the presence of NADPH. During this reductive step, the corresponding 4-proR hydrogen was abstracted from [4R-3H]-NADPH during hydride transfer. This is thus the first report of a double-bond reductase involved in phenylpropanoid metabolism, and which is presumed to be involved in plant defense. In situ mRNA hybridization indicated that the PPDBR transcripts in P. taeda stem sections were localized to the vascular cambium, as well as to radial and axial parenchyma cell types. Additionally, using P. taeda cell suspension culture crude protein extracts, dehydrodiconiferyl and coniferyl alcohols could be dehydrogenated to afford dehydrodiconiferyl and coniferyl aldehydes. Furthermore, these same extracts were able to convert dihydrodehydrodiconiferyl and dihydroconiferyl aldehydes into the corresponding alcohols. Taken together, these results indicate that in the crude extracts dehydrodiconiferyl and coniferyl alcohols can be converted to dihydrodehydrodiconiferyl and dihydroconiferyl alcohols through a three-step process, i.e. by initial phenylpropenol oxidation, then sequential PPDBR and phenylpropanal reductions, respectively.
- Kasahara, Hiroyuki,Jiao, Ying,Bedgar, Diana L.,Kim, Sung-Jin,Patten, Ann M.,Xia, Zhi-Qiang,Davin, Laurence B.,Lewis, Norman G.
-
p. 1765 - 1780
(2008/02/12)
-
- Kinetic resolution of a dihydrobenzofuran-type neolignan by lipase-catalysed acetylation
-
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.
- Van Dyck, Stefaan M.O.,Lemiere, Guy L.F.,Jonckers, Tim H.M.,Dommisse, Roger,Pieters, Luc,Buss, Volker
-
p. 785 - 789
(2007/10/03)
-
- Neolignan glucosides from Jasminum urophyllum
-
A novel neolignan-secoiridoid glucoside, jasurolignoside, and a new neolignan, urolignoside, have been isolated from Jasminum urophyllum. Their structures were elucidated on the basis of 2D-NMR and chemical methods.
- Shen, Ya-Ching,Hsieh, Pei-Wen,Kuo, Yao-Haur
-
p. 719 - 723
(2007/10/03)
-
- Absolute Configuration of Dehydrodiconiferil Alcohol
-
The absolute configuration of dehydrodiconiferyl alcohol was elucidated by chemical degradation. (+)-Dehydrodiconiferyl alcohol was prepared by optical resolving the racemate with HPLC and degraded to methylsuccinic acid.This methylsuccinic was the (R)-(+)-enantiomer, the optical purity of which was confirmed by HPLC after suitable conversion.This result shows that the absolute configuration of C-2 of (+)-dehydrodiconiferyl alcohol was S.H-2 and H-3 of (+)-dehydrodiconiferyl alcohol are trans, so the absolute confuguration of C-3 must be R.Thus, (+)-dehydrodiconiferyl alcohol was 2S and 3R, and the (-)-enantiomer was 2R and 3S.The absolute configuration of natural glucosides of dehydrodiconiferyl alcohol was also elucidated.
- Hirai, Nobuhiro,Okamoto, Masahiko,Udagawa, Hiroake,Yamamuro, Munehiro,Kato, Masayoshi,Koshimizu, Koichi
-
p. 1679 - 1684
(2007/10/02)
-
- LIGNANS IN CELL CULTURES OF PICEA GLEHNII
-
A suspension culture derived from the seedling leaves of Picea glehnii accumulated two lignans, pinoresinol and trans-dihydrodehydrodiconiferyl alcohol.The enantiomeric compositions of pinoresinol and dihydrodehydrodiconifery
- Nabeta, Kensuke,Hirata, Megumi,Ohki, Yuriko,Samaraweera, S. W.Ananda,Okuyama, Hiroshi
-
p. 409 - 414
(2007/10/02)
-
- Isolation of neoanisatin derivatives from the pericarps of Illicium majus with other constituents
-
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.
- Kouno,Hashimoto,Enjoji,Takahashi,Kaneto,Yang
-
p. 1773 - 1778
(2007/10/02)
-
- Lignans from Trachelospermum asiaticum (Tracheolospermum . II)
-
Lignans of Trachelospermum asiaticum were isolated from the polar fraction of the methanol percolate, and the structures were determined.Trachelosiaside (matairesinol 5'-C-β-D-glucoside) was isolated as the first naturally occurring C-glucoside of lignan.
- Abe, Fumiko,Yamauchi, Tatsuo
-
p. 4340 - 4345
(2007/10/02)
-
