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
Fourteen known compounds were isolated from the aerial parts of Artemisia anomala and identified as follows： zhepiresinol （1）, （-）-lariciresinol （2）, ficusal （3）, medioresinol （4）, （＋）-syringaresinol （5...Fourteen known compounds were isolated from the aerial parts of Artemisia anomala and identified as follows： zhepiresinol （1）, （-）-lariciresinol （2）, ficusal （3）, medioresinol （4）, （＋）-syringaresinol （5）, 1β,2β-epoxy-3β,4α,10α-trihydroxyguaian- 6α,12-olide （6）, 5β,10α-dihydroxy-1α/-dehydroleucodin （7）, 3α-chloro-8α-acetoxy-4β,10α-dihydroxy-1β,2β-epoxy-5α,7αHguai- 11 （13）-en- 12,6α-olide （8）, 13-O-desacetyleudesma-afraglaucolide （9）, 1,10-seco-4ξ-hydroxy-muurol-5-ene- 1,10-diketone （10）, 1α-hydroxyafraglaucolide（11）, aurantiamide （12）, indole-3-aldehyde （13）, loliolide （14）. All these compounds were isolated from this plant for the first time and compounds 1-4, 8, 10, 13 were obtained from genus Artemisia for the first time.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 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
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
Sinopodophylli Fructus is the commonly used traditional Tibetan medicinal herb. In the present study, we established a reversed-phase high performance liquid chromatography method to simultaneously determine three lig...Sinopodophylli Fructus is the commonly used traditional Tibetan medicinal herb. In the present study, we established a reversed-phase high performance liquid chromatography method to simultaneously determine three lignans and five flavonoid constituents, namely podophyllotoxin, desoxypodophyUotoxin, 4＇-demethyldesoxypodophyllotoxin, 8-prenylkaemferol, quercetin, kaempferol, 8,2＇-diprenylquercetin 3-methylether and 8-prenylquercetin, in Sinopodophylli Fructus. The chromatographic separation was achieved on a C_18 analytical column with a gradient mobile phase consisting of acetonitrile and 0.05% phosphoric acid at a flow rate of 1.0 mL/min. UV detection was set at 290 nm and 370 rim, and the column oven was set at 35℃. This method provided a good reproducibility, and its overall intra- and inter-day precision was less than 3% and 4%, respectively. The recovery of the method was 98.29%-101.60%, and a good linearity （R2≥0.9992） was obtained for all the analytes over a relatively wide range of concentration. A total of 17 samples ofS. hexandrum （12 fruits, 5 roots and rhizomes） were collected from different areas and then successfully quantified. The results indicated that the contents of eight compounds significantly varied （the sum content ranged from 16.90 to 55.68 mg/g）, and prenylated fiavonoids could be used as marker constituents in the identification and quality control of Sinopodophylli Fructus.展开更多
Nine lignans were isolated and purified by silica gel, ODS, Sephadex LH-20 column chromatographies, preparative HPLC and recrystallization from the aerial parts ofArtemisia absinthium L., and identified as follows： d...Nine lignans were isolated and purified by silica gel, ODS, Sephadex LH-20 column chromatographies, preparative HPLC and recrystallization from the aerial parts ofArtemisia absinthium L., and identified as follows： diayangambin （1）, sesartemin （2）, epiyangambin （3）, （＋）arborone （4）, （-）syringaresinol （5）, epiashchantin （6）, caruilignan C （7）, 7β-caruilignan C （8）, yangambin （9）. Compounds 4, 5, 7, 8 were isolated from this plant for the first time.展开更多
Phenolic compounds, metabolites of the phenylpropanoid pathway, play an important role in the growth and environmental adaptation of many plants. Phenylalanine ammonia-lyase(PAL) is the first key enzyme of the phenylp...Phenolic compounds, metabolites of the phenylpropanoid pathway, play an important role in the growth and environmental adaptation of many plants. Phenylalanine ammonia-lyase(PAL) is the first key enzyme of the phenylpropanoid pathway. The present study was designed to investigate whether there is a multi-gene family in I. Indigotic and, if so, to characterize their properties. We conducted a comprehensive survey on the transcription profiling database by using tBLASTn analysis. Several bioinformatics methods were employed to perform the prediction of composition and physicochemical characters. The expression levels of IiPAL genes in various tissues of I. indigotica with stress treatment were examined by quantitative real-time PCR. Protoplast transient transformation was used to observe the locations of IiPALs. IiPALs were functionally characterized by expression with pET-32a vector in Escherichia colis strain BL21(DE3). Integration of transcripts and metabolite accumulations was used to reveal the relation between IiPALs and target compounds. An new gene(IiPAL2) was identified and both IiPALs had the conserved enzymatic active site Ala-Ser-Gly and were classified as members of dicotyledon. IiPAL1 and IiPAL2 were expressed in roots, stems, leaves, and flowers, with the highest expression levels of IiPAL1 and IiPAL2 being observed in stems and roots, respectively. The two genes responded to the exogenous elicitor in different manners. Subcellular localization experiment showed that both IiPALs were localized in the cytosol. The recombinant proteins were shown to catalyze the conversion of L-Phe to trans-cinnamic acid. Correlation analysis indicated that Ii PAL1 was more close to the biosynthesis of secondary metabolites than IiPAL2. In conclusion, the present study provides a basis for the elucidation of the role of Ii PALs genes in the biosynthesis of phenolic compounds, which will help further metabolic engineering to improve the accumulation of bioactive components in I.indigotica.展开更多
Two new flavone glycosides, isoetin-7-O-β-D-glucopyranosyl-2′-O-α-L-arabinopyranoside （1） and isoetin-7-O-β-D-glucopyranosyl-2′-O-α-D-glucopyranoside （2）, a new lignan, mongolicumin A （3）, and a new guaian...Two new flavone glycosides, isoetin-7-O-β-D-glucopyranosyl-2′-O-α-L-arabinopyranoside （1） and isoetin-7-O-β-D-glucopyranosyl-2′-O-α-D-glucopyranoside （2）, a new lignan, mongolicumin A （3）, and a new guaianolide, mongolicumin B （4） were isolated from the aerial part of Taraxacum mongolicum. Their structures were elucidated mainly by spectral analyses.展开更多
AIM: To study the chemical constituents of the roots and stem bark of Kadsura coccinea. METHOD: Compounds were isolated by column chromatography on silica gel and Sephadex LH-20, and finally purified by prep-HPLC. The...AIM: To study the chemical constituents of the roots and stem bark of Kadsura coccinea. METHOD: Compounds were isolated by column chromatography on silica gel and Sephadex LH-20, and finally purified by prep-HPLC. Their structures were elucidated by extensive spectroscopic methods, including 1D- and 2D-NMR, and HR-ESI-MS. RESULTS: Two compounds were determined as(7′S,8′S,8R)-(8β,8′α)- dimethyl-4,4′-dihydroxy-5,3′-dimethoxy-5′-cyclolignan glucoside(1) and micrandiactone H(2), respectively. CONCLUSION: Compunds 1 and 2 are new and neither showed inhibitory effects on nitric oxide(NO) production in lipopolysaccharide-induced RAW264.7 macrophages.展开更多
A phytochemical investigation on the aerial parts of Artemisia brachyloba led to the isolation of 13 compounds（1-13） for the first time, including eight lignans（1-8） and five flavonoids（9-13）. The structures of ...A phytochemical investigation on the aerial parts of Artemisia brachyloba led to the isolation of 13 compounds（1-13） for the first time, including eight lignans（1-8） and five flavonoids（9-13）. The structures of the isolated compounds were elucidated by analysis of the NMR spectroscopic data and comparison with the literature. The 1 H and 13 C NMR data of 1 were fully assigned for the first time by the 2 D NMR analysis. All the isolates were evaluated for their inhibitory effects on nitric oxide production in lipopolysaccharide-challenged BV-2 microglial cells.展开更多
A new sesquilignan, 7＇,8＇-didehydroherpetotriol （1）, and a new lignan glycoside, （＋）-isolariciresinol-9＇-O-α-L-rhamnopyra- nosy1-（1→6）-[3-D-glucopyranoside （2）, were isolated from the branches of Diptero...A new sesquilignan, 7＇,8＇-didehydroherpetotriol （1）, and a new lignan glycoside, （＋）-isolariciresinol-9＇-O-α-L-rhamnopyra- nosy1-（1→6）-[3-D-glucopyranoside （2）, were isolated from the branches of Dipteronia dyeriana. Their structures were elucidated by spectroscopic methods and chemical evidence. Compound 1 possessed inhibitory activity against human leukaemia K562 cells with an IC50 value of 39 μmol/L.展开更多
Herpetospermum caudigerum lignans(HTL),one of the potential drugs with anti-hepatitis B virus and hepatoprotective effects,has limited clinical applications because of poor aqueous solubility and low bioavailability.B...Herpetospermum caudigerum lignans(HTL),one of the potential drugs with anti-hepatitis B virus and hepatoprotective effects,has limited clinical applications because of poor aqueous solubility and low bioavailability.Both herpetrione(HPE)and herpetin(HPN)are the most abundant ingredients in HTL and exhibit weak acidity.The purpose of the present study was to produce dried preparations of HTL(composed of HPE and HPN)nanosuspensions(HTL-NS)with high redispersibility using lyophilization technology.The HTL-NS was prepared by utilizing precipitation-combined homogenization technology based on acid-base neutralization reactions,and critical formulation and process parameters affecting the characteristics of HTL-NS were optimized.The resultant products were characterized by particle size analysis,SEM,XRD,stability,solubility,dissolution and in vivo bioavailability.HTL-NS showed near-spherical-shaped morphology and the size was 243 nm with a narrow PDI value of 0.187.The dried preparations with a relatively large particle size of 286 nm and a PDI of 0.215 were achieved by using 4%(W/V)mannitol as cryoprotectants,and had a better stability at 4 or 25 oC for 2 months,compared to HTL-NS.In the in vitro test,the dried preparations showed markedly increased solubility and dissolution velocity.Besides,in the in vivo evaluation,it exhibited significant increases in AUC0–t,C_(max),MRT and a decrease in T_(max),compared to the raw drug..In conclusion,our results provide a basis for the development of a drug delivery system for poorly water-soluble ingredients with p H-dependent solubility.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National Natural Science Foundation of China(Grant No.30973629).
文摘Fourteen known compounds were isolated from the aerial parts of Artemisia anomala and identified as follows： zhepiresinol （1）, （-）-lariciresinol （2）, ficusal （3）, medioresinol （4）, （＋）-syringaresinol （5）, 1β,2β-epoxy-3β,4α,10α-trihydroxyguaian- 6α,12-olide （6）, 5β,10α-dihydroxy-1α/-dehydroleucodin （7）, 3α-chloro-8α-acetoxy-4β,10α-dihydroxy-1β,2β-epoxy-5α,7αHguai- 11 （13）-en- 12,6α-olide （8）, 13-O-desacetyleudesma-afraglaucolide （9）, 1,10-seco-4ξ-hydroxy-muurol-5-ene- 1,10-diketone （10）, 1α-hydroxyafraglaucolide（11）, aurantiamide （12）, indole-3-aldehyde （13）, loliolide （14）. All these compounds were isolated from this plant for the first time and compounds 1-4, 8, 10, 13 were obtained from genus Artemisia for the first time.
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 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.
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National Key Technology R&D Program"New Drug Innovation"of China(Grant No.2009ZX09308-004,2013ZX09103002-006)
文摘Sinopodophylli Fructus is the commonly used traditional Tibetan medicinal herb. In the present study, we established a reversed-phase high performance liquid chromatography method to simultaneously determine three lignans and five flavonoid constituents, namely podophyllotoxin, desoxypodophyUotoxin, 4＇-demethyldesoxypodophyllotoxin, 8-prenylkaemferol, quercetin, kaempferol, 8,2＇-diprenylquercetin 3-methylether and 8-prenylquercetin, in Sinopodophylli Fructus. The chromatographic separation was achieved on a C_18 analytical column with a gradient mobile phase consisting of acetonitrile and 0.05% phosphoric acid at a flow rate of 1.0 mL/min. UV detection was set at 290 nm and 370 rim, and the column oven was set at 35℃. This method provided a good reproducibility, and its overall intra- and inter-day precision was less than 3% and 4%, respectively. The recovery of the method was 98.29%-101.60%, and a good linearity （R2≥0.9992） was obtained for all the analytes over a relatively wide range of concentration. A total of 17 samples ofS. hexandrum （12 fruits, 5 roots and rhizomes） were collected from different areas and then successfully quantified. The results indicated that the contents of eight compounds significantly varied （the sum content ranged from 16.90 to 55.68 mg/g）, and prenylated fiavonoids could be used as marker constituents in the identification and quality control of Sinopodophylli Fructus.
基金National Natural Science Foundation of China (Grant No. 30973629)
文摘Nine lignans were isolated and purified by silica gel, ODS, Sephadex LH-20 column chromatographies, preparative HPLC and recrystallization from the aerial parts ofArtemisia absinthium L., and identified as follows： diayangambin （1）, sesartemin （2）, epiyangambin （3）, （＋）arborone （4）, （-）syringaresinol （5）, epiashchantin （6）, caruilignan C （7）, 7β-caruilignan C （8）, yangambin （9）. Compounds 4, 5, 7, 8 were isolated from this plant for the first time.
基金supported by the Natural Science Foundation of China(Nos.31100221 and 81325024)
文摘Phenolic compounds, metabolites of the phenylpropanoid pathway, play an important role in the growth and environmental adaptation of many plants. Phenylalanine ammonia-lyase(PAL) is the first key enzyme of the phenylpropanoid pathway. The present study was designed to investigate whether there is a multi-gene family in I. Indigotic and, if so, to characterize their properties. We conducted a comprehensive survey on the transcription profiling database by using tBLASTn analysis. Several bioinformatics methods were employed to perform the prediction of composition and physicochemical characters. The expression levels of IiPAL genes in various tissues of I. indigotica with stress treatment were examined by quantitative real-time PCR. Protoplast transient transformation was used to observe the locations of IiPALs. IiPALs were functionally characterized by expression with pET-32a vector in Escherichia colis strain BL21(DE3). Integration of transcripts and metabolite accumulations was used to reveal the relation between IiPALs and target compounds. An new gene(IiPAL2) was identified and both IiPALs had the conserved enzymatic active site Ala-Ser-Gly and were classified as members of dicotyledon. IiPAL1 and IiPAL2 were expressed in roots, stems, leaves, and flowers, with the highest expression levels of IiPAL1 and IiPAL2 being observed in stems and roots, respectively. The two genes responded to the exogenous elicitor in different manners. Subcellular localization experiment showed that both IiPALs were localized in the cytosol. The recombinant proteins were shown to catalyze the conversion of L-Phe to trans-cinnamic acid. Correlation analysis indicated that Ii PAL1 was more close to the biosynthesis of secondary metabolites than IiPAL2. In conclusion, the present study provides a basis for the elucidation of the role of Ii PALs genes in the biosynthesis of phenolic compounds, which will help further metabolic engineering to improve the accumulation of bioactive components in I.indigotica.
文摘Two new flavone glycosides, isoetin-7-O-β-D-glucopyranosyl-2′-O-α-L-arabinopyranoside （1） and isoetin-7-O-β-D-glucopyranosyl-2′-O-α-D-glucopyranoside （2）, a new lignan, mongolicumin A （3）, and a new guaianolide, mongolicumin B （4） were isolated from the aerial part of Taraxacum mongolicum. Their structures were elucidated mainly by spectral analyses.
基金supported by the Program for New Century Excellent Talents in University(NCET-12-0977)the National New Drug Innovation Great Project of China(2011ZX09307-002-02)+1 种基金the Program for Changjiang Scholars and Innovative Research Team in a University(PCSIRT-IRT1193)the Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions(PAPD)
文摘AIM: To study the chemical constituents of the roots and stem bark of Kadsura coccinea. METHOD: Compounds were isolated by column chromatography on silica gel and Sephadex LH-20, and finally purified by prep-HPLC. Their structures were elucidated by extensive spectroscopic methods, including 1D- and 2D-NMR, and HR-ESI-MS. RESULTS: Two compounds were determined as(7′S,8′S,8R)-(8β,8′α)- dimethyl-4,4′-dihydroxy-5,3′-dimethoxy-5′-cyclolignan glucoside(1) and micrandiactone H(2), respectively. CONCLUSION: Compunds 1 and 2 are new and neither showed inhibitory effects on nitric oxide(NO) production in lipopolysaccharide-induced RAW264.7 macrophages.
基金National Natural Science Foundation of China(Grant No.81373294)National Key Technology R&D Program"New Drug Innovation"of China(Grant No.2018ZX09711001-008-003)
文摘A phytochemical investigation on the aerial parts of Artemisia brachyloba led to the isolation of 13 compounds（1-13） for the first time, including eight lignans（1-8） and five flavonoids（9-13）. The structures of the isolated compounds were elucidated by analysis of the NMR spectroscopic data and comparison with the literature. The 1 H and 13 C NMR data of 1 were fully assigned for the first time by the 2 D NMR analysis. All the isolates were evaluated for their inhibitory effects on nitric oxide production in lipopolysaccharide-challenged BV-2 microglial cells.
基金the Ministry of Science and Technology of China(2005DKA21006)the Knowledge Innovation Project of Chinese Academy of Sciences.
文摘A new sesquilignan, 7＇,8＇-didehydroherpetotriol （1）, and a new lignan glycoside, （＋）-isolariciresinol-9＇-O-α-L-rhamnopyra- nosy1-（1→6）-[3-D-glucopyranoside （2）, were isolated from the branches of Dipteronia dyeriana. Their structures were elucidated by spectroscopic methods and chemical evidence. Compound 1 possessed inhibitory activity against human leukaemia K562 cells with an IC50 value of 39 μmol/L.
基金supported by the National Key New Drugs Innovation Foundation(No.2015ZX09101025)the National Science Foundation of China(No.81503169)the New Drugs Development Special Foundation of Beijing City of China(No.Z141100002214007)
文摘Herpetospermum caudigerum lignans(HTL),one of the potential drugs with anti-hepatitis B virus and hepatoprotective effects,has limited clinical applications because of poor aqueous solubility and low bioavailability.Both herpetrione(HPE)and herpetin(HPN)are the most abundant ingredients in HTL and exhibit weak acidity.The purpose of the present study was to produce dried preparations of HTL(composed of HPE and HPN)nanosuspensions(HTL-NS)with high redispersibility using lyophilization technology.The HTL-NS was prepared by utilizing precipitation-combined homogenization technology based on acid-base neutralization reactions,and critical formulation and process parameters affecting the characteristics of HTL-NS were optimized.The resultant products were characterized by particle size analysis,SEM,XRD,stability,solubility,dissolution and in vivo bioavailability.HTL-NS showed near-spherical-shaped morphology and the size was 243 nm with a narrow PDI value of 0.187.The dried preparations with a relatively large particle size of 286 nm and a PDI of 0.215 were achieved by using 4%(W/V)mannitol as cryoprotectants,and had a better stability at 4 or 25 oC for 2 months,compared to HTL-NS.In the in vitro test,the dried preparations showed markedly increased solubility and dissolution velocity.Besides,in the in vivo evaluation,it exhibited significant increases in AUC0–t,C_(max),MRT and a decrease in T_(max),compared to the raw drug..In conclusion,our results provide a basis for the development of a drug delivery system for poorly water-soluble ingredients with p H-dependent solubility.
