Lignans have been established as a privileged scaffold in drug discovery,particularly in anticancer and antioxidant properties.Concise and efficient construction of lignans and their derivatives in a single operation ...Lignans have been established as a privileged scaffold in drug discovery,particularly in anticancer and antioxidant properties.Concise and efficient construction of lignans and their derivatives in a single operation holds great medicinal significance for structure-activity relationship studies yet remains challenging.Drawing inspiration from the biosynthesis of lignans,we present a general,high-step-economy palladium-catalyzed reaction that converts simple chemical feedstocks into dehydrodibenzylbutyrolactone lignans through the in-situ construction and coupling of two phenylpropanoid molecules.The diversity of organoboronic acids and the editability of enyne provide a powerful platform for the rapid construction of lignan libraries,featuring 82 lignans analogs,collective syntheses of 10 distinct lignan skeletons,and 13 hybrid molecules combining pharmacophore fragments with drug and derivatives.The subtle combination of phosphine ligands with quinones for switching chemoselectivity is vital to the success of this protocol.展开更多
Five previously undescribed diterpenoids,named succipenoids D‒H(1‒5),along with four undescribed lignans,named succignans A‒D(6‒9),were isolated from the dichloromethane extract of Chinese medicinal succinum.Compounds...Five previously undescribed diterpenoids,named succipenoids D‒H(1‒5),along with four undescribed lignans,named succignans A‒D(6‒9),were isolated from the dichloromethane extract of Chinese medicinal succinum.Compounds 1‒5 were characterized as nor-abietane diterpenoids,while compounds 6‒9 were identified as lignans polymerized from two groups of phenylpropanoid units.The structures of these novel compounds,including their absolute configurations,were determined through spectroscopic and computational methods.Biological assessments of renal fibrosis demonstrated that compounds 6 and 7 effectively reduce the expression of proteins associated with renal fibrosis,includingα-smooth muscle actin(α-SMA),collagen I,and fibronectin in transforming growth factor-β1(TGF-β1)induced normal rat kidney proximal tubular epithelial cells(NRK-52e).展开更多
The anti-inflammatory phytochemical investigation of the leaves of Illicium dunnianum(I.dunnianum)resulted in the isolation of five pairs of new lignans(1–5),and 7 known analogs(6–12).The separation of enantiomer mi...The anti-inflammatory phytochemical investigation of the leaves of Illicium dunnianum(I.dunnianum)resulted in the isolation of five pairs of new lignans(1–5),and 7 known analogs(6–12).The separation of enantiomer mixtures 1–5 to 1a/1b–5a/5b was achieved using a chiral column with acetonitrile−water mixtures as eluents.The planar structures of 1–2 were previously undescribed,and the chiral separation and absolute configurations of 3–5 were reported for the first time.Their structures were determined through comprehensive spectroscopic data analysis[nuclear magnetic resonance(NMR),high-resolution electrospray ionization mass(HR-ESI-MS),infrared(IR),and ultraviolet(UV)]and quantum chemistry calculations(ECD).The new isolates were evaluated by measuring their inhibitory effect on NO in lipopolysaccharide(LPS)-stimulated BV-2 cells.Compounds 1a,3a,3b,and 5a demonstrated partial inhibition of NO production in a concentration-dependent manner.Western blot and real-time polymerase chain reaction(PCR)assays revealed that 1a down-regulated the messenger ribonucleic acid(mRNA)levels of tumor necrosis factorα(TNF-α),interleukin-6(IL-6),COX-2,and iNOS and the protein expressions of COX-2 and iNOS.This research provides guidance and evidence for the further development and utilization of I.dunnianum.展开更多
Twelve lignans(1-12)isolated from Amomum tsao-ko leaves were evaluated for the inhibitory effects againstα-glucosidase and PTP1B.Compounds 1-4 and 10 showed inhibition on α-glucosidase with inhibitory ratios ranging...Twelve lignans(1-12)isolated from Amomum tsao-ko leaves were evaluated for the inhibitory effects againstα-glucosidase and PTP1B.Compounds 1-4 and 10 showed inhibition on α-glucosidase with inhibitory ratios ranging from53.8%to90.0%,while compound10 demonstrated 56.1% inhibition on PTP1B at 200μM.Notably,erythro-5-methoxy-dadahol A(2)and threo-5-methoxy-dadahol A(3)displayed obvious inhibition on α-glucosidase with IC50 values of 33.3μM and 22.1μM,significantly outperforming acarbose(IC_(50)=344.0μM).Kinetic study revealed that compound 3 maintained amixed-typemode,engaging with both free enzyme and enzyme-substrate complex via noncompetitive and uncompetitive mechanisms.Molecular docking simulations further clarified its interactions with the key residues of Trp402,Lys400,and Gly361 in the catalytic pocket.In vivo evaluation demonstrated that oryzativol A(1)showed dose-dependent hypoglycemic effects in an oral starch tolerance test,reducing postprandial blood glucose levels(AUC)by 21.1%(20 mg/kg)and 24.9%(40 mg/kg).These results highlight the potential of lignans in A.tsao-ko as α-glucosidase inhibitors for managing type 2 diabetes,warranting further exploration of their therapeutic potential.展开更多
Dietary supplementation with plant-derivedα-linolenic acid(ALA)has the potential to alleviate the insufficient intake of global n-3 long-chain polyunsaturated fatty acids(n-3 LCPUFAs),but faces the bottleneck of high...Dietary supplementation with plant-derivedα-linolenic acid(ALA)has the potential to alleviate the insufficient intake of global n-3 long-chain polyunsaturated fatty acids(n-3 LCPUFAs),but faces the bottleneck of highβ-oxidation consumption,oxidative susceptibility,and low conversion efficiency.The current study investigated how flax lignans with different degrees of polymerization and glycosylation affect the conversion of ALA to n-3 LCPUFAs in mice over 35 days of administering sunflower phospholipid-stabilized flaxseed oil nanoemulsions.Results showed that flax lignan macromolecules(FLM)increased hepatic protein expression of elongase of very long chain fatty acid 5(Elovl5,24.2%)and fatty acid desaturase 2(Fads2,44.7%),thereby positively regulating ALA conversion pathways and raising serum eicosapentaenoic acid(EPA)levels(52.7%)via liver lipid re-efflux.Secoisolariciresinol diglucoside(SDG)enhanced ALA desaturation by upregulating hepatic protein expression of Fads1(30.4%)and Fads2(45.6%),increasing serum EPA levels(55.9%)and hepatic docosahexaenoic acid(DHA)levels(10%).Secoisolariciresinol(SECO)elevated hepatic protein expression of Elovl2(30.7%),Elovl5(11.7%),Fads1(37.9%),and Fads2(24.1%),but also increased carnitine palmitoyltransferase 1a(45.2%),leading to decreased ALA,EPA,and DHA levels in serum and liver.Therefore,in comparison,FLM and SDG emerge as the dominant structural units that positively regulate the conversion of ALA.These findings lay a groundwork for designing precise dietary delivery systems to enhance the conversion to n-3 LCPUFAs.展开更多
Flaxseed lignan macromolecules(FLM)are a class of important secondary metabolites in fl axseed,which have been widely concerned due to their biological and pharmacological properties,especially for their antioxidative...Flaxseed lignan macromolecules(FLM)are a class of important secondary metabolites in fl axseed,which have been widely concerned due to their biological and pharmacological properties,especially for their antioxidative activity.For the composition and structure of FLM,our results confirmed that ferulic acid glycoside(FerAG)was directly ester-linked with herbacetin diglucoside(HDG)or pinoresinol diglucoside(PDG),which might determine the beginning of FLM biosynthesis.Additionally,p-coumaric acid glycoside(CouAG)might determine the end of chain extension during FLM synthesis in fl axseed.FLM exhibited higher antioxidative activity in polar systems,as shown by its superior 1,1-diphenyl-2-picrylhydrazyl(DPPH)free radical scavenging capacity compared to the 2,2’-azinobis(3-ehtylbenzothiazolin-6-sulfnic acid)(ABTS)cation free radical scavenging capacity in non-polar systems.Moreover,the antioxidative activity of FLM was found to be highly dependent on its composition and structure.In particular,it was positively correlated with the number of phenolic hydroxyl groups(longer FLM chains)and inversely related to the steric hindrance at the ends(lower levels of FerAG and CouAG).These fi ndings verifi ed the potential application of FLM in nonpolar systems,particularly in functional food emulsions。展开更多
Five new furofuran lignans and their derivatives,(-)-glaberide I 4-O-β-D-glucopyranoside(1a),(+)-glaberide I 4-O-β-D-glucopyranoside(1b),(+)-glaberide I 7'-ethoxy-4-O-β-D-glucopyranoside(2a),(-)-glaberide I 7&#...Five new furofuran lignans and their derivatives,(-)-glaberide I 4-O-β-D-glucopyranoside(1a),(+)-glaberide I 4-O-β-D-glucopyranoside(1b),(+)-glaberide I 7'-ethoxy-4-O-β-D-glucopyranoside(2a),(-)-glaberide I 7'-ethoxy-4-O-β-D-glucopyranoside(2b),and(-)-isoeucommin A(3b),along with fifteen known analogs were isolated from the stems of Dendrobium'Sonia'.These compounds were classified into ten pairs of enantiomers or diastereoisomers via chiral resolution,and their structures were determined based on extensive spectroscopic data.Their absolute configurations were determined by hydrolysis,comparison of experimental and calculated electronic circular dichroism(ECD)data,and single-crystal X-ray diffraction analysis.The isolates were evaluated for their ability to inhibit nitric oxide(NO)production in RAW264.7 cells.Among them,syringaresinol(5)exhibited prominent inhibition activity,with an IC50 value of 28.4±3.0μmol·L~(-1),and there was a slight difference between 5a,5b and the racemic mixture 5.展开更多
As a traditional Chinese herbal medicine,Schisandrae Chinensis Fructus(SC)has been used in medicine and food industry due to its health care and therapeutic effects.Over the past 20 years,the use of SC and its active ...As a traditional Chinese herbal medicine,Schisandrae Chinensis Fructus(SC)has been used in medicine and food industry due to its health care and therapeutic effects.Over the past 20 years,the use of SC and its active ingredient lignans in the prevention and treatment of liver diseases has been increasing,and their hepatoprotective effects has increased the interest of the public and academia.Therefore,in the present work,we first determined the effectiveness of SC in the treatment of liver diseases such as metabolic associated fatty liver disease,alcoholic liver disease,cholestatic liver disease and acute liver injury.Subsequently,the pharmacological effects and molecular mechanisms of lignans,the active components of SC,for liver disease treatment were comprehensively summarized for the first time.The results showed that the lignans in SC could achieve hepatoprotective effects by regulating lipid metabolism,anti-fibrosis,anti-inflammation,anti-oxidation,anti-tumor and regulating bile acid metabolism.The mechanism mainly involved adenosine 5’-monophosphate-activated protein kinase,endoplasmic reticulum stress,sterol regulatory element binding protein 1c,autophagy,transforming growth factor-β,mitogen-activated protein kinase,microRNA,nuclear factor kappa-B,nuclear factor erythroid-2-related factor 2,heat shock proteins and pregnane X receptor signaling pathways.These results can lay a scientific foundation for the development of hepatoprotective drugs or functional foods from SC/lignans.展开更多
Lignans are a prominent group of phenolic compounds ubiquitously present in the plant kingdom,playing a critical role in both plant physiology and human health.Structurally they are characterized by the dimerization o...Lignans are a prominent group of phenolic compounds ubiquitously present in the plant kingdom,playing a critical role in both plant physiology and human health.Structurally they are characterized by the dimerization of two phenylpropane units to attain diverse chemical configurations that contribute to their wide range of biological activities.In plants,lignans function primarily as defense molecules,protecting against pathogens,herbivores,and environmental stressors.These compounds also participate in plant growth regulation and lignification processes.From a nutritional and medicinal perspective,lignans are valued for their significant health benefits.They act as phytoestrogens,which can modulate estrogen receptors in humans,thereby offering protective effects against hormone-related diseases such as breast cancer and menopausal symptoms.Additionally,lignans possess potent antioxidant and anti-inflammatory properties,contributing to cardiovascular health and cancer prevention.This review aims to provide a comprehensive overview of the importance of lignans in plants,highlighting their chemical diversity,health-promoting properties and stress adaptation.By synthesizing recent research findings,this review underscores the significance of lignans in enhancing plant resilience under stress and human health.It explores their potential applications in the food and pharmaceutical industries.Besides,it will also focus on the widely used method for enhancing the production of these high-value secondary metabolites in plant cell cultures to meet their requirement in pharmaceutical industries.展开更多
In this study,two new kaurane diterpenes(16,17),together with 12 lignans(1-12),a triterpene(15),and two other compounds(13,14)were isolated from the woods of Agathis dammara.The structure of the new compound was deter...In this study,two new kaurane diterpenes(16,17),together with 12 lignans(1-12),a triterpene(15),and two other compounds(13,14)were isolated from the woods of Agathis dammara.The structure of the new compound was determined by HR ESIMS and 1D/2D NMR spectroscopy,and its absolute configuration was determined by electronic circular dichroism(ECD)exciton chirality method.Compounds 5,11,14 exhibit significant hypoglycaemic activity in zebrafish,and their mechanism of action is to enhance glucose uptake in zebrafish.展开更多
The identification of natural, plant-derived compounds with pesticidal properties is crucial for developing environmentally sustainable alternatives to synthetic pesticides. In this study, four major lignans—dihydroc...The identification of natural, plant-derived compounds with pesticidal properties is crucial for developing environmentally sustainable alternatives to synthetic pesticides. In this study, four major lignans—dihydroclusin, cubebin, clusin, and yatein—were isolated from the crude extract of Piper cubeba fruit. Phytotoxicity assays revealed herbicidal activity against Agrostis stolonifera, with dihydroclusin and clusin exhibiting the highest efficacy, inhibiting seed germination by 50% and showing IC50 values of 2.9 µM and 45 µM, respectively, against Lemna paucicostata. Additionally, all compounds, except dihydroclusin, demonstrated fungicidal activity against the strawberry anthracnose pathogen Colletotrichum fragariae. Moreover, only dihydroclusin exhibited larvicidal activity against Aedes aegypti, causing 96% mortality of mosquito larvae at the 100-ppm concentration tested. These findings highlight the broad-spectrum bioactivity of Piper cubeba lignans, suggesting their potential as alternative agents of synthetic pesticides for managing agricultural pests.展开更多
A new lignan glycoside, named （7S,8R,8＇R）-（-）-lariciresinol-9-O-a-L-rhamnopyranosyl （1-2） 13-D-glucopyranoside （1）,was isolated from the ethanol extract ofPilea cavaleriei Levi subsp, cavaleriei, together wit...A new lignan glycoside, named （7S,8R,8＇R）-（-）-lariciresinol-9-O-a-L-rhamnopyranosyl （1-2） 13-D-glucopyranoside （1）,was isolated from the ethanol extract ofPilea cavaleriei Levi subsp, cavaleriei, together with 17 known lignans （2-18）. The structuresof these compounds were elucidated by extensive spectroscopic analysis, including 1D NMR, 2D NMR and HR-ESI-MS.All the compounds were obtained from the genus Pilea for the first time.展开更多
The stereochemistry of two 6, 9-oxygen bridge dibenzocyclooctadiene lignans from Kadsura coccinea, are difficult to separate and very unstable. The present study was designed to develop a high-performance liquid chrom...The stereochemistry of two 6, 9-oxygen bridge dibenzocyclooctadiene lignans from Kadsura coccinea, are difficult to separate and very unstable. The present study was designed to develop a high-performance liquid chromatography using circular dichroism detection for the analysis of the stereochemistry. A new 6, 9-oxygen bridge dibenzocyclooctadiene lignans named Kadsulignan Q was firstly found with an S-biphenyl configuration. The other compound was identified as Kadsulignan L with an R- biphenyl configuration. In order to obtain kinetic data on their reversible interconversion, the stability was measured at different deuterated solvents such as deuterated methanol, deuterated chloroform and deuterated dimethylsulfoxide. The lignans were more unstable and converted more easily in deuterated methanol than in deuterated chloroform and deuterated dimethylsulfoxide.展开更多
To study the antioxidant constituents from the stems of Dendrobium nobile, and to discuss theft structure-activity relationship. Compounds were isolated from a 60% ethanolic extract by various chromatographic techniqu...To study the antioxidant constituents from the stems of Dendrobium nobile, and to discuss theft structure-activity relationship. Compounds were isolated from a 60% ethanolic extract by various chromatographic techniques and were identified by spectral analysis. The antioxidant activities of compounds were evaluated by DPPH free radical scavenging assay. Five phenanthrenes and four lignans were obtained from the active fractions ofD. nobile. Their structures were identified as fimbriatone （1）, confusarin （2）, flavanthrinin （3）, 2,5-dihydroxy-4,9-dimethoxyphenanthrene （4）, 3,7-dihydroxy-2,4-dimethoxyphenanthrene （5）, syringaresinol （6）, pinoresinol （7）, medioresinol （8） and lirioresinol-A （9）, respectively. Compounds 2 and 6 exhibited more potent DPPH scavenging activities than vitamin C. All the above compounds were reported from this plant for the first time, and compounds 3, 4 and 9 were reported for the first time from the genus of Dendrobiurn. For all phenanthrenes and lignans, an electron-donating methoxyl group in the ortho position to the phenolic hydroxyl group exhibits enhanced antioxidant activities.展开更多
Aim To study the chemical constituents of seeds of Herpetospermum caudigerum. Methods Column chromatography was used in the isolation procedure, and the structure was elucidated by spectral data, whose pharmacologic a...Aim To study the chemical constituents of seeds of Herpetospermum caudigerum. Methods Column chromatography was used in the isolation procedure, and the structure was elucidated by spectral data, whose pharmacologic activity was assayed in vitro. Results A new compound named herpetin was isolated, whose structure was determined to be 3-benzofuran methanol-2, 3-dihydm-2-（4- hydroxy-3-methoxyphenyl ）-4-methoxy-6-[ tetrahydm-2-（ 3-hydroxy-4-methoxyphenyl ）-3-methanol ]-2- furanmethyl, showed significant inhibitory effects on HBV-DNA and the replication and expression of HBsAg and HBeAg. Conclusion Herpetin offers wide research and development prospect.展开更多
A new lignan, together with a known one, was isolated from Isodon lophanthoides var. gerardianus [Bentham] H. Hara. The structure of the new lignan was elucidated as 1_acetoxyl_2e_piperonyl_6e_[6_methoxyl_pi...A new lignan, together with a known one, was isolated from Isodon lophanthoides var. gerardianus [Bentham] H. Hara. The structure of the new lignan was elucidated as 1_acetoxyl_2e_piperonyl_6e_[6_methoxyl_piperonyl]_3,7_dioxabicyclo_[3,3,0]_octane mainly by 1D and 2D NMR techniques.展开更多
Seven known dibenzocyclooctadiene lignans,tigloylgomisin P(1), angeloylgomisin P(2),gomisin A(3),Schizandrin(4),angeloylgomisin H(5),gomisin B(6) and R(+)-gomisin M_1(7)were isolated from Kadsura heteroclita.The confo...Seven known dibenzocyclooctadiene lignans,tigloylgomisin P(1), angeloylgomisin P(2),gomisin A(3),Schizandrin(4),angeloylgomisin H(5),gomisin B(6) and R(+)-gomisin M_1(7)were isolated from Kadsura heteroclita.The conformation of tiglolylgomisin P(1)was established by 2D NMR techniques.Using[~3H]platelet activating factor(PAF)binding to human platelet membrane assay,(1),(2)and(7)showed PAF receptor antagonistic activities.展开更多
Four new seco-dibenzocyclooctadiene lignans,kadlongilignans A-D(1-4),consisting of a rare 6,7-seco-(1),two 15,16-seco-(2 and 3) and a 9,10-seco-dibenzocyclooctadiene(4) lignans,were isolated from the roots of Kadsura ...Four new seco-dibenzocyclooctadiene lignans,kadlongilignans A-D(1-4),consisting of a rare 6,7-seco-(1),two 15,16-seco-(2 and 3) and a 9,10-seco-dibenzocyclooctadiene(4) lignans,were isolated from the roots of Kadsura longipedunculata.Their structures were elucidated by spectroscopic analysis,including extensive NM R,MS and ECD(electronic circular dichroism) spectra.Compounds 3 and 4 exhibited potent inhibitory activities against NO(nitric oxide) production of LPS(lipopolysaccharide)-induced murine macrophages with the inhibition rates of 36.3% and 26.9%,respectively.展开更多
One new compound, ilexlignan A （1）, was isolated from the root of llex pubescens. Its structure was elucidated by the combination of one- and two-dimensional NMR analysis, mass spectrometry, CD spectrum measurement ...One new compound, ilexlignan A （1）, was isolated from the root of llex pubescens. Its structure was elucidated by the combination of one- and two-dimensional NMR analysis, mass spectrometry, CD spectrum measurement and chemical evidence.展开更多
A glucosidic indole-lignan conjugate with a novel carbon skeleton, named isatindolignanoside A（1）, was isolated from an aqueous extract of the Isatis indigotica roots ＂ban lan gen＂. Its structure was elucidated by...A glucosidic indole-lignan conjugate with a novel carbon skeleton, named isatindolignanoside A（1）, was isolated from an aqueous extract of the Isatis indigotica roots ＂ban lan gen＂. Its structure was elucidated by comprehensive analysis of spectroscopic data, including J-and NOESY correlation-based configurational analysis, circular dichroism（CD） data, enzyme hydrolysis, and theoretical ECD calculation. In a preliminary assay, compound 1 showed antiviral activity against Coxsackie virus B3. This compound is the first example of natural product having a structural feature of conjugation between indole and lignan units, and its biosynthetic pathway is postulated.展开更多
基金Financial support was provided by the State Key Laboratory of Pulp and Paper Engineering(No.2022PY01)the National Natural Science Foundation of China(Nos.22231002 and 21871095)the Key-Area Research and Development Program of Guangdong Province(No.2020B010188001)。
文摘Lignans have been established as a privileged scaffold in drug discovery,particularly in anticancer and antioxidant properties.Concise and efficient construction of lignans and their derivatives in a single operation holds great medicinal significance for structure-activity relationship studies yet remains challenging.Drawing inspiration from the biosynthesis of lignans,we present a general,high-step-economy palladium-catalyzed reaction that converts simple chemical feedstocks into dehydrodibenzylbutyrolactone lignans through the in-situ construction and coupling of two phenylpropanoid molecules.The diversity of organoboronic acids and the editability of enyne provide a powerful platform for the rapid construction of lignan libraries,featuring 82 lignans analogs,collective syntheses of 10 distinct lignan skeletons,and 13 hybrid molecules combining pharmacophore fragments with drug and derivatives.The subtle combination of phosphine ligands with quinones for switching chemoselectivity is vital to the success of this protocol.
基金supported by Shenzhen Fundamental Research Program(No.JCYJ20200109114003921).
文摘Five previously undescribed diterpenoids,named succipenoids D‒H(1‒5),along with four undescribed lignans,named succignans A‒D(6‒9),were isolated from the dichloromethane extract of Chinese medicinal succinum.Compounds 1‒5 were characterized as nor-abietane diterpenoids,while compounds 6‒9 were identified as lignans polymerized from two groups of phenylpropanoid units.The structures of these novel compounds,including their absolute configurations,were determined through spectroscopic and computational methods.Biological assessments of renal fibrosis demonstrated that compounds 6 and 7 effectively reduce the expression of proteins associated with renal fibrosis,includingα-smooth muscle actin(α-SMA),collagen I,and fibronectin in transforming growth factor-β1(TGF-β1)induced normal rat kidney proximal tubular epithelial cells(NRK-52e).
基金supported by the Basic Research Program of the Natural Science Fund-Frontier Leading Technology Basic Research Special Project(No.SBK2023050003)by the University Science and Technology Innovation Team of Department of Education of Guizhou Province(No.QJ[2023]099).
文摘The anti-inflammatory phytochemical investigation of the leaves of Illicium dunnianum(I.dunnianum)resulted in the isolation of five pairs of new lignans(1–5),and 7 known analogs(6–12).The separation of enantiomer mixtures 1–5 to 1a/1b–5a/5b was achieved using a chiral column with acetonitrile−water mixtures as eluents.The planar structures of 1–2 were previously undescribed,and the chiral separation and absolute configurations of 3–5 were reported for the first time.Their structures were determined through comprehensive spectroscopic data analysis[nuclear magnetic resonance(NMR),high-resolution electrospray ionization mass(HR-ESI-MS),infrared(IR),and ultraviolet(UV)]and quantum chemistry calculations(ECD).The new isolates were evaluated by measuring their inhibitory effect on NO in lipopolysaccharide(LPS)-stimulated BV-2 cells.Compounds 1a,3a,3b,and 5a demonstrated partial inhibition of NO production in a concentration-dependent manner.Western blot and real-time polymerase chain reaction(PCR)assays revealed that 1a down-regulated the messenger ribonucleic acid(mRNA)levels of tumor necrosis factorα(TNF-α),interleukin-6(IL-6),COX-2,and iNOS and the protein expressions of COX-2 and iNOS.This research provides guidance and evidence for the further development and utilization of I.dunnianum.
基金financially supported by the Yunnan Major Scientific and Technological Program(202202AE090035)CAS Interdisciplinary Team of“Light of West China”Program(xbzg-zdsys-202405)+2 种基金the Yunnan Fundamental Research Projects(202201AV070010,202301AS070069,202402AA310003)Strategic Priority Research Program of the Chinese Academy of Sciences(XDB1230000)the Yunnan Province Science and Technology Department(202305AH340005).
文摘Twelve lignans(1-12)isolated from Amomum tsao-ko leaves were evaluated for the inhibitory effects againstα-glucosidase and PTP1B.Compounds 1-4 and 10 showed inhibition on α-glucosidase with inhibitory ratios ranging from53.8%to90.0%,while compound10 demonstrated 56.1% inhibition on PTP1B at 200μM.Notably,erythro-5-methoxy-dadahol A(2)and threo-5-methoxy-dadahol A(3)displayed obvious inhibition on α-glucosidase with IC50 values of 33.3μM and 22.1μM,significantly outperforming acarbose(IC_(50)=344.0μM).Kinetic study revealed that compound 3 maintained amixed-typemode,engaging with both free enzyme and enzyme-substrate complex via noncompetitive and uncompetitive mechanisms.Molecular docking simulations further clarified its interactions with the key residues of Trp402,Lys400,and Gly361 in the catalytic pocket.In vivo evaluation demonstrated that oryzativol A(1)showed dose-dependent hypoglycemic effects in an oral starch tolerance test,reducing postprandial blood glucose levels(AUC)by 21.1%(20 mg/kg)and 24.9%(40 mg/kg).These results highlight the potential of lignans in A.tsao-ko as α-glucosidase inhibitors for managing type 2 diabetes,warranting further exploration of their therapeutic potential.
基金supported by grants from the National Natural Science Foundation of China(32072267)China Agriculture Research System(CARS-14)+1 种基金National Key Research and Development Program of China(2023YFD2100404)the Innovation Group Project of Hubei Province(2023AFA042).
文摘Dietary supplementation with plant-derivedα-linolenic acid(ALA)has the potential to alleviate the insufficient intake of global n-3 long-chain polyunsaturated fatty acids(n-3 LCPUFAs),but faces the bottleneck of highβ-oxidation consumption,oxidative susceptibility,and low conversion efficiency.The current study investigated how flax lignans with different degrees of polymerization and glycosylation affect the conversion of ALA to n-3 LCPUFAs in mice over 35 days of administering sunflower phospholipid-stabilized flaxseed oil nanoemulsions.Results showed that flax lignan macromolecules(FLM)increased hepatic protein expression of elongase of very long chain fatty acid 5(Elovl5,24.2%)and fatty acid desaturase 2(Fads2,44.7%),thereby positively regulating ALA conversion pathways and raising serum eicosapentaenoic acid(EPA)levels(52.7%)via liver lipid re-efflux.Secoisolariciresinol diglucoside(SDG)enhanced ALA desaturation by upregulating hepatic protein expression of Fads1(30.4%)and Fads2(45.6%),increasing serum EPA levels(55.9%)and hepatic docosahexaenoic acid(DHA)levels(10%).Secoisolariciresinol(SECO)elevated hepatic protein expression of Elovl2(30.7%),Elovl5(11.7%),Fads1(37.9%),and Fads2(24.1%),but also increased carnitine palmitoyltransferase 1a(45.2%),leading to decreased ALA,EPA,and DHA levels in serum and liver.Therefore,in comparison,FLM and SDG emerge as the dominant structural units that positively regulate the conversion of ALA.These findings lay a groundwork for designing precise dietary delivery systems to enhance the conversion to n-3 LCPUFAs.
基金support from National Natural Science Foundation of China(32072267)supported by China Agriculture Research System of CRAS-14.
文摘Flaxseed lignan macromolecules(FLM)are a class of important secondary metabolites in fl axseed,which have been widely concerned due to their biological and pharmacological properties,especially for their antioxidative activity.For the composition and structure of FLM,our results confirmed that ferulic acid glycoside(FerAG)was directly ester-linked with herbacetin diglucoside(HDG)or pinoresinol diglucoside(PDG),which might determine the beginning of FLM biosynthesis.Additionally,p-coumaric acid glycoside(CouAG)might determine the end of chain extension during FLM synthesis in fl axseed.FLM exhibited higher antioxidative activity in polar systems,as shown by its superior 1,1-diphenyl-2-picrylhydrazyl(DPPH)free radical scavenging capacity compared to the 2,2’-azinobis(3-ehtylbenzothiazolin-6-sulfnic acid)(ABTS)cation free radical scavenging capacity in non-polar systems.Moreover,the antioxidative activity of FLM was found to be highly dependent on its composition and structure.In particular,it was positively correlated with the number of phenolic hydroxyl groups(longer FLM chains)and inversely related to the steric hindrance at the ends(lower levels of FerAG and CouAG).These fi ndings verifi ed the potential application of FLM in nonpolar systems,particularly in functional food emulsions。
基金financially supported by the Program of Shanghai Municipal Commission of Health and Family Planning[No.ZY(2021-2023)-0215]。
文摘Five new furofuran lignans and their derivatives,(-)-glaberide I 4-O-β-D-glucopyranoside(1a),(+)-glaberide I 4-O-β-D-glucopyranoside(1b),(+)-glaberide I 7'-ethoxy-4-O-β-D-glucopyranoside(2a),(-)-glaberide I 7'-ethoxy-4-O-β-D-glucopyranoside(2b),and(-)-isoeucommin A(3b),along with fifteen known analogs were isolated from the stems of Dendrobium'Sonia'.These compounds were classified into ten pairs of enantiomers or diastereoisomers via chiral resolution,and their structures were determined based on extensive spectroscopic data.Their absolute configurations were determined by hydrolysis,comparison of experimental and calculated electronic circular dichroism(ECD)data,and single-crystal X-ray diffraction analysis.The isolates were evaluated for their ability to inhibit nitric oxide(NO)production in RAW264.7 cells.Among them,syringaresinol(5)exhibited prominent inhibition activity,with an IC50 value of 28.4±3.0μmol·L~(-1),and there was a slight difference between 5a,5b and the racemic mixture 5.
基金supported by National Natural Science Foundation of China(81891012,U19A2010,81630101)Sichuan Province Science and Technology Support Program(2021JDRC0041)Innovation Team and Talents Cultivation Program of National Administration of Traditional Chinese Medicine(ZYYCXTD-D-202209).
文摘As a traditional Chinese herbal medicine,Schisandrae Chinensis Fructus(SC)has been used in medicine and food industry due to its health care and therapeutic effects.Over the past 20 years,the use of SC and its active ingredient lignans in the prevention and treatment of liver diseases has been increasing,and their hepatoprotective effects has increased the interest of the public and academia.Therefore,in the present work,we first determined the effectiveness of SC in the treatment of liver diseases such as metabolic associated fatty liver disease,alcoholic liver disease,cholestatic liver disease and acute liver injury.Subsequently,the pharmacological effects and molecular mechanisms of lignans,the active components of SC,for liver disease treatment were comprehensively summarized for the first time.The results showed that the lignans in SC could achieve hepatoprotective effects by regulating lipid metabolism,anti-fibrosis,anti-inflammation,anti-oxidation,anti-tumor and regulating bile acid metabolism.The mechanism mainly involved adenosine 5’-monophosphate-activated protein kinase,endoplasmic reticulum stress,sterol regulatory element binding protein 1c,autophagy,transforming growth factor-β,mitogen-activated protein kinase,microRNA,nuclear factor kappa-B,nuclear factor erythroid-2-related factor 2,heat shock proteins and pregnane X receptor signaling pathways.These results can lay a scientific foundation for the development of hepatoprotective drugs or functional foods from SC/lignans.
基金Ragini Singh is very thankful to the Jamia Hamdard University Grants Commission,India for research grant No.162000681.
文摘Lignans are a prominent group of phenolic compounds ubiquitously present in the plant kingdom,playing a critical role in both plant physiology and human health.Structurally they are characterized by the dimerization of two phenylpropane units to attain diverse chemical configurations that contribute to their wide range of biological activities.In plants,lignans function primarily as defense molecules,protecting against pathogens,herbivores,and environmental stressors.These compounds also participate in plant growth regulation and lignification processes.From a nutritional and medicinal perspective,lignans are valued for their significant health benefits.They act as phytoestrogens,which can modulate estrogen receptors in humans,thereby offering protective effects against hormone-related diseases such as breast cancer and menopausal symptoms.Additionally,lignans possess potent antioxidant and anti-inflammatory properties,contributing to cardiovascular health and cancer prevention.This review aims to provide a comprehensive overview of the importance of lignans in plants,highlighting their chemical diversity,health-promoting properties and stress adaptation.By synthesizing recent research findings,this review underscores the significance of lignans in enhancing plant resilience under stress and human health.It explores their potential applications in the food and pharmaceutical industries.Besides,it will also focus on the widely used method for enhancing the production of these high-value secondary metabolites in plant cell cultures to meet their requirement in pharmaceutical industries.
基金supported by Project XWZY-2023-0303 supported by Traditional Chinese Medicine Foundation of Xiamen.
文摘In this study,two new kaurane diterpenes(16,17),together with 12 lignans(1-12),a triterpene(15),and two other compounds(13,14)were isolated from the woods of Agathis dammara.The structure of the new compound was determined by HR ESIMS and 1D/2D NMR spectroscopy,and its absolute configuration was determined by electronic circular dichroism(ECD)exciton chirality method.Compounds 5,11,14 exhibit significant hypoglycaemic activity in zebrafish,and their mechanism of action is to enhance glucose uptake in zebrafish.
文摘The identification of natural, plant-derived compounds with pesticidal properties is crucial for developing environmentally sustainable alternatives to synthetic pesticides. In this study, four major lignans—dihydroclusin, cubebin, clusin, and yatein—were isolated from the crude extract of Piper cubeba fruit. Phytotoxicity assays revealed herbicidal activity against Agrostis stolonifera, with dihydroclusin and clusin exhibiting the highest efficacy, inhibiting seed germination by 50% and showing IC50 values of 2.9 µM and 45 µM, respectively, against Lemna paucicostata. Additionally, all compounds, except dihydroclusin, demonstrated fungicidal activity against the strawberry anthracnose pathogen Colletotrichum fragariae. Moreover, only dihydroclusin exhibited larvicidal activity against Aedes aegypti, causing 96% mortality of mosquito larvae at the 100-ppm concentration tested. These findings highlight the broad-spectrum bioactivity of Piper cubeba lignans, suggesting their potential as alternative agents of synthetic pesticides for managing agricultural pests.
文摘A new lignan glycoside, named （7S,8R,8＇R）-（-）-lariciresinol-9-O-a-L-rhamnopyranosyl （1-2） 13-D-glucopyranoside （1）,was isolated from the ethanol extract ofPilea cavaleriei Levi subsp, cavaleriei, together with 17 known lignans （2-18）. The structuresof these compounds were elucidated by extensive spectroscopic analysis, including 1D NMR, 2D NMR and HR-ESI-MS.All the compounds were obtained from the genus Pilea for the first time.
基金supported by the PAPD(Priority Academic Program Development)of Jiangsu Higher Education Institutions,University Science Research Project of Jiangsu Province(No.09KJB350002)National Key Technology R&D Program(No.2012BAI30B02),National Natural Science Foundation of China(No.30901853)Hepatic Fibrosis Innovative Medicine-Research and Development of Fructus Schisandrae capsule(No.F12-157-9-00)
文摘The stereochemistry of two 6, 9-oxygen bridge dibenzocyclooctadiene lignans from Kadsura coccinea, are difficult to separate and very unstable. The present study was designed to develop a high-performance liquid chromatography using circular dichroism detection for the analysis of the stereochemistry. A new 6, 9-oxygen bridge dibenzocyclooctadiene lignans named Kadsulignan Q was firstly found with an S-biphenyl configuration. The other compound was identified as Kadsulignan L with an R- biphenyl configuration. In order to obtain kinetic data on their reversible interconversion, the stability was measured at different deuterated solvents such as deuterated methanol, deuterated chloroform and deuterated dimethylsulfoxide. The lignans were more unstable and converted more easily in deuterated methanol than in deuterated chloroform and deuterated dimethylsulfoxide.
文摘To study the antioxidant constituents from the stems of Dendrobium nobile, and to discuss theft structure-activity relationship. Compounds were isolated from a 60% ethanolic extract by various chromatographic techniques and were identified by spectral analysis. The antioxidant activities of compounds were evaluated by DPPH free radical scavenging assay. Five phenanthrenes and four lignans were obtained from the active fractions ofD. nobile. Their structures were identified as fimbriatone （1）, confusarin （2）, flavanthrinin （3）, 2,5-dihydroxy-4,9-dimethoxyphenanthrene （4）, 3,7-dihydroxy-2,4-dimethoxyphenanthrene （5）, syringaresinol （6）, pinoresinol （7）, medioresinol （8） and lirioresinol-A （9）, respectively. Compounds 2 and 6 exhibited more potent DPPH scavenging activities than vitamin C. All the above compounds were reported from this plant for the first time, and compounds 3, 4 and 9 were reported for the first time from the genus of Dendrobiurn. For all phenanthrenes and lignans, an electron-donating methoxyl group in the ortho position to the phenolic hydroxyl group exhibits enhanced antioxidant activities.
文摘Aim To study the chemical constituents of seeds of Herpetospermum caudigerum. Methods Column chromatography was used in the isolation procedure, and the structure was elucidated by spectral data, whose pharmacologic activity was assayed in vitro. Results A new compound named herpetin was isolated, whose structure was determined to be 3-benzofuran methanol-2, 3-dihydm-2-（4- hydroxy-3-methoxyphenyl ）-4-methoxy-6-[ tetrahydm-2-（ 3-hydroxy-4-methoxyphenyl ）-3-methanol ]-2- furanmethyl, showed significant inhibitory effects on HBV-DNA and the replication and expression of HBsAg and HBeAg. Conclusion Herpetin offers wide research and development prospect.
文摘A new lignan, together with a known one, was isolated from Isodon lophanthoides var. gerardianus [Bentham] H. Hara. The structure of the new lignan was elucidated as 1_acetoxyl_2e_piperonyl_6e_[6_methoxyl_piperonyl]_3,7_dioxabicyclo_[3,3,0]_octane mainly by 1D and 2D NMR techniques.
基金This project was supported by National Natural Science Foundation of China.
文摘Seven known dibenzocyclooctadiene lignans,tigloylgomisin P(1), angeloylgomisin P(2),gomisin A(3),Schizandrin(4),angeloylgomisin H(5),gomisin B(6) and R(+)-gomisin M_1(7)were isolated from Kadsura heteroclita.The conformation of tiglolylgomisin P(1)was established by 2D NMR techniques.Using[~3H]platelet activating factor(PAF)binding to human platelet membrane assay,(1),(2)and(7)showed PAF receptor antagonistic activities.
基金financially supported by CAMS Initiative for Innovative Medicine(No.CAMS-2016-I2M-1-010)the Drug Innovation Major Project(No.2018ZX09711001-001-003)。
文摘Four new seco-dibenzocyclooctadiene lignans,kadlongilignans A-D(1-4),consisting of a rare 6,7-seco-(1),two 15,16-seco-(2 and 3) and a 9,10-seco-dibenzocyclooctadiene(4) lignans,were isolated from the roots of Kadsura longipedunculata.Their structures were elucidated by spectroscopic analysis,including extensive NM R,MS and ECD(electronic circular dichroism) spectra.Compounds 3 and 4 exhibited potent inhibitory activities against NO(nitric oxide) production of LPS(lipopolysaccharide)-induced murine macrophages with the inhibition rates of 36.3% and 26.9%,respectively.
基金Natural Science Foundation of Guangdong Province of China(No.7017651)Program for New Century Excellent Talents in University of Peoples Republic of China(No.NCET-04-0289).
文摘One new compound, ilexlignan A （1）, was isolated from the root of llex pubescens. Its structure was elucidated by the combination of one- and two-dimensional NMR analysis, mass spectrometry, CD spectrum measurement and chemical evidence.
基金Financial support from the National Natural Science Foundation of China (Nos. 81373287, 81630094, and 30825044) is acknowledged
文摘A glucosidic indole-lignan conjugate with a novel carbon skeleton, named isatindolignanoside A（1）, was isolated from an aqueous extract of the Isatis indigotica roots ＂ban lan gen＂. Its structure was elucidated by comprehensive analysis of spectroscopic data, including J-and NOESY correlation-based configurational analysis, circular dichroism（CD） data, enzyme hydrolysis, and theoretical ECD calculation. In a preliminary assay, compound 1 showed antiviral activity against Coxsackie virus B3. This compound is the first example of natural product having a structural feature of conjugation between indole and lignan units, and its biosynthetic pathway is postulated.
