As important sources of new drugs,natural products(NPs)are conceptually biosynthesized from simple structural pioneers(i.e.building blocks).The traditional non-targeted purification strategy extensively suffers from t...As important sources of new drugs,natural products(NPs)are conceptually biosynthesized from simple structural pioneers(i.e.building blocks).The traditional non-targeted purification strategy extensively suffers from the time-consuming and laborious bottlenecks.Fortunately,liquid chromatography–mass spectrometry/mass spectrometry(LC–MS/MS)-guided separations widely succeed in recent decades.However,it is still challenging for LC–MS/MS to precisely capture new NPs.Efficiently extracting information from the chaotic chemical composition and confident structural annotation are two primary technical barriers for pursuing the interesting structures,particularly those exhibiting trace distributions and high-level structural complexity.Here,to provide accurate guidance for the follow-up phytochemical purification,molecular defect filtering(MDF)and feature-based molecular networking(FBMN)[1]were incorporated to explore NPs and thereafter,bottom-up structural analysis was undertaken through identifying building blocks with full exciting energy ramp(FEER)-MS 3 matching.Sesquiterpene-chromone hybrids(SCHs)structurally configured by two building blocks such as units A(chromone)and B(sesquiterpene)[2]in agarwood were characterized as a proof-of-concept.Twenty-five SCHs were captured and identified.Thereof,seven new SCHs were purified with a LC–MS/MS-guided manner and annotated using nuclear magnetic resonance(NMR)spectroscopy to justify the proposed structures.Moreover,their cell-protective and anti-inflammatory activities were evaluated.Together,the incorporation of post-acquisition data processing strategies and FEER-MS 3 spectrum matchingassisted building blocks identification facilitated novel NPs exploration and purification.展开更多
Traumatic axonal lesions of peripheral nerves disrupt neuronal connections with their targets,resulting in the loss of motor and sensory functions.Despite the peripheral nervous system’s capacity for axonal regrowth,...Traumatic axonal lesions of peripheral nerves disrupt neuronal connections with their targets,resulting in the loss of motor and sensory functions.Despite the peripheral nervous system’s capacity for axonal regrowth,this may lead to permanent impairements resulting in a loss of quality of life and a high socioeconomic burden.展开更多
The Tiger Milk mushrooms(Lignosus spp.)have long been used as traditional folk medicines throughout Southeast Asia.However,the chemical constituents of these species remain largely unexplored.In this study,four type ...The Tiger Milk mushrooms(Lignosus spp.)have long been used as traditional folk medicines throughout Southeast Asia.However,the chemical constituents of these species remain largely unexplored.In this study,four type Ⅰ sesquit-erpene synthases(LrhTS1-LrhTS4)from Lignosus rhinocerusTM02® were functionally characterized through genome mining,in vitro enzymatic assays,and heterologous expression in an Escherichia coli host engineered to overexpress an exogenous mevalonate pathway.The enzyme products were analyzed by GC-MS and further purified and struc-turally elucidated by NMR spectroscopy.A total of 11 sesquiterpenes(1-11)were identified,among which two were unstable and converted to stable derivatives(2 to 2a and 7 to 7a).Notably,compounds 1-10 are reported from the genus Lignosus for the first time.LrhTS1 and LrhTS3 exhibited high catalytic specificity,whereas LrhTS2 and LrhTS4 displayed product promiscuity.This work expands the knowledge of terpene synthase from mushroom,and advances the understanding of the chemical basis underlying the bioactivity of the Lignosus rhinocerus TM02®.展开更多
The Asteraceae family,one of the largest angiosperm families,is rich in terpenoid secondary metabolites with significant medicinal value.Asteraceae plants have evolved a diverse array of terpenoid biosynthesis pathway...The Asteraceae family,one of the largest angiosperm families,is rich in terpenoid secondary metabolites with significant medicinal value.Asteraceae plants have evolved a diverse array of terpenoid biosynthesis pathways,reflecting their adaptive significance and complex regulatory mechanisms.However,the evolutionary patterns and transcriptional regulatory mechanisms governing these biosynthetic processes remain unclear.This study investigates the evolution and transcriptional regulation of terpenoid biosynthesis genes in Asteraceae.Comparative genomic analysis of 19 Asteraceae and six out-group species revealed that Asteraceae species diverged~74.03 million years ago and were distinctly divided into three subfamilies.A total of 1714 terpene synthase(TPS)genes were identified,predominantly in the TPS-a and TPS-b subfamilies.Caryophyllene-type sesquiterpene biosynthetic gene clusters(BGCs)were detected in 10 species,with their formation due to whole-genome duplication(WGD)and tandem duplication.By integrating weighted gene coexpression network analysis(WGCNA)and machine learning methods,key transcription factors regulating caryophyllene synthase(CPS)in Carthamus tinctorius were identified.A multilayered gene regulatory network was constructed to identify potential regulatory factors involved in TPS gene regulation under light stress.By exploring the evolutionary patterns and potential regulatory relationships involved in terpenoid biosynthesis in Asteraceae,this study provides important insights into TPS gene evolution.In addition,the findings also offer guidance for optimizing genetic engineering strategies in terpenoid-based drug development.展开更多
The first total synthesis of marine sesquiterpene(hydro)quinone meroterpenoids dysideanones A and E–G(1 and 4–6)has been accomplished in an enantioselective and divergent way.The sesquiterpene fragment and the aroma...The first total synthesis of marine sesquiterpene(hydro)quinone meroterpenoids dysideanones A and E–G(1 and 4–6)has been accomplished in an enantioselective and divergent way.The sesquiterpene fragment and the aromatic moiety were efficiently connected via a site-selective and diastereoselective intermolecular alkylation of Wieland–Miescher ketone derivative 9 and benzyl bromide 10.The core 6/6/6/6-fused backbone of dysideanones was efficiently constructed through an intramolecular radical cyclization reaction.Dysideanone G(6)was easily prepared on a gram-scale and dysideanones A,E,and F(1,4,and 5)were divergently transformed from dysideanone G(6)in one or two steps.展开更多
A rare sesquiterpene of hawkteasesquioid A(1),featuring a novel 5/6/5 tricyclic system containing a 6,5-spiroketal motif,was isolated from the bark of Litsea coreana Lévl.var.lanuginosa(hawk tea).The structure of...A rare sesquiterpene of hawkteasesquioid A(1),featuring a novel 5/6/5 tricyclic system containing a 6,5-spiroketal motif,was isolated from the bark of Litsea coreana Lévl.var.lanuginosa(hawk tea).The structure of this compound was elucidated based on the high-resolution electrospray ionization mass spectrometry(HRESIMS),one-dimensional(1D)and two-dimensional(2D)nuclear magnetic resonance(NMR)spectroscopy,and single-crystal X-ray diffraction data.The cytotoxicity of this compound was assessed on the A549,HT-29,and SW1990 cell lines.展开更多
Antimicrobial resistance is one of the most pressing global health challenges,as many pathogens are rapidly evolv-ing to evade existing treatments.Despite this urgent need for new solutions,natural plant-derived compo...Antimicrobial resistance is one of the most pressing global health challenges,as many pathogens are rapidly evolv-ing to evade existing treatments.Despite this urgent need for new solutions,natural plant-derived compounds remain relatively underexplored in the development of antimicrobial drugs.This report highlights an innovative approach to discovering potent antimicrobial agents through bioguided fractionation of numerous plant species from the rich Argentinean flora.By systematically screening 60 species(over 177 extracts)for antimicrobial activity against representative strains of gram-positive and gram-negative bacteria,we identified promising bioactive com-pounds within the Asteraceae family-particularly sesquiterpene lactones from the Xanthium genus.Building on this basis,we synthesized semi-synthetic derivatives by chemically modifying plant sub-extracts,focusing on structures incorporating heteroatoms and/or heterocycles containing oxygen and nitrogen(important for the bioavailability and bioactivity that they are capable of providing).These modifications were evaluated fortheir potential to enhance antimicrobial efficacy against bacteria and Candida species,including resistant strains.Our findings suggest that tai-loring natural metabolites from Xanthium and related Asteraceae species can significantly improve their antimicrobial properties.This strategy offers a promising pathway for the development of novel therapeutic agents to combat bacterial and fungal infections in an era of rising drug resistance.展开更多
A phytochemical investigation on the aerial parts of Artemisia giraldii var. longipedunculata led to the isolation of 10 known sesquiterpenes, including 12-hydroxy-α-cyperone(1), 1β,6α-dihydroxyeudesma-4(15)-en...A phytochemical investigation on the aerial parts of Artemisia giraldii var. longipedunculata led to the isolation of 10 known sesquiterpenes, including 12-hydroxy-α-cyperone(1), 1β,6α-dihydroxyeudesma-4(15)-ene(2), carainterol A(3), oplodiol(4), douglanin(5), 1α-hydroxyisodauc-4-en-15-al(6), 3α,6α-dihydroxybisabola-4,10-diene(7), 4α,5β-dihydroxybisabola-2,10-diene(8), opposit-4(15)-ene-1β,7-diol(9), and saniculamoid D(10), respectively. Their structures were elucidated by analysis of the MS and NMR spectroscopic data and comparison with the literature. All the isolates were obtained from A. giraldii var. longipedunculata for the first time, and five of them were obtained from the genus Artemisia for the first time. Additionally, the 13 C NMR data of 1 were fully assigned based on the 2 D NMR data for the first time.展开更多
A new sesquiterpene, named vladimenal (1), was isolated from the roots of Vladimiria souliei. The structure was elucidated on the basis of spectroscopic analysis.
Three new sesquiterpene alkaloids,1-desacetylwilforgine(1),1-desacetylwilforine(2),and 9′-hydroxy-2-nicotinoylwilforine (3) were isolated from the roots of Tripterygium wilfordii Hook f.,along with six known al...Three new sesquiterpene alkaloids,1-desacetylwilforgine(1),1-desacetylwilforine(2),and 9′-hydroxy-2-nicotinoylwilforine (3) were isolated from the roots of Tripterygium wilfordii Hook f.,along with six known alkaloids.Their structures were established on the basis of spectral analysis.展开更多
A protoilludane sesquiterpene (named xanthocerapene) was isolated from the wood of Xanthoceras sorbifolia Bunge. Its structure, including the relative configuration was established by spectroscopic and chemical methods.
A new sesquiterpene, 12,13-di-acetoxyl-1,4,6,11-eudesmanetetrol 1, was isolated from Michelia yunnanensis. The structure was elucidated on the basis of spectral data.
A new sesquiterpene polyol ester, angulatin D, has been isolated from the root bark of Celastrus angulatus. The chemical structure is elucidated on the basis of spectral analysis.
Two new beta-dihydroagarofuran sesquiterpenes were isolated from Euonymus phellomana Loes. and their structures were established on the basis of spectral analysis.
A new sesquiterpene polyol ester was isolated from the leaves of Celastrus angulatus. Its structure was determined as 1 (beta), 2 (beta), 9 (a) -triacetoxy-8 (a) -((a) -hydroxyl-isobutyryloxy)-15-benzoyloxy-4 (a) -hyd...A new sesquiterpene polyol ester was isolated from the leaves of Celastrus angulatus. Its structure was determined as 1 (beta), 2 (beta), 9 (a) -triacetoxy-8 (a) -((a) -hydroxyl-isobutyryloxy)-15-benzoyloxy-4 (a) -hydroxy-dihydroagarofuran by means of NMR, MS and IR spectral analysis. Preliminary biological study on antitumor activity revealed that this compound showed strong nonselective cytotoxicity against four of the NCI panel cell lines.展开更多
One new dimeric(1) and two monomeric sesquiterpene lactones(5 and 13), together with 10 known compounds(2-4, 6-12), were isolated from Artemisia heptapotamica collected in Almaty region of Kazakhstan. All compounds we...One new dimeric(1) and two monomeric sesquiterpene lactones(5 and 13), together with 10 known compounds(2-4, 6-12), were isolated from Artemisia heptapotamica collected in Almaty region of Kazakhstan. All compounds were isolated from this plant for the first time. The structures of the new compounds were mainly achieved by extensive analysis of MS, 1D and 2D NMR spectroscopic data, and ECD spectrum as well. The inhibitory activities of all isolates against activation of NF-κB induced by LPS were assessed on a THP1-Dual cell model. Some of them showed strong inhibitory activity with IC50 values ranging from 2 to 25μmol·L^-1.展开更多
Three new sesquiterpene glycosides with alloaromadendrane and ylangene-derived type aglycones,named dendrofindlayanosides A-C(1-3),one new cyclopacamphane type sesquiterpene named dendrofindlayanobilin A(4),together w...Three new sesquiterpene glycosides with alloaromadendrane and ylangene-derived type aglycones,named dendrofindlayanosides A-C(1-3),one new cyclopacamphane type sesquiterpene named dendrofindlayanobilin A(4),together with five known compounds have been isolated from stems of Dendrobium findlayanum.Their structures were determined on the basis of spectroscopic and chemical methods.展开更多
Sesquiterpenes are the major pharmacodynamic components of agarwood,a precious traditional Chinese medicine obtained from the resinous portions of Aquilaria sinensis trees that form in response to environmental stress...Sesquiterpenes are the major pharmacodynamic components of agarwood,a precious traditional Chinese medicine obtained from the resinous portions of Aquilaria sinensis trees that form in response to environmental stressors.To characterize the sesquiterpene synthases responsible for sesquiterpene production in A.sinensis,a bioinformatics analysis of the genome of A.sinensis identifi ed six new terpene synthase genes,and 16 sesquiterpene synthase genes were identifi ed as type TPS-a in a phylogenetic analysis.The expression patterns for eight of the sesquiterpene synthase genes after treatment with various hormones or hydrogen peroxide were analyzed by real-time quantitative PCR.The results suggest that 100μM methyl jasmonate,ethephon,(±)-abscisic acid or hydrogen peroxide could be eff ective short-term eff ectors to increase the expression of sesquiterpene synthase genes,while 1 mM methyl salicylate may have long-term eff ects on increasing the expression of specifi c sesquiterpene synthase genes(e.g.,As-SesTPS,AsVS,AsTPS12 and AsTPS29).The expression changes in these genes under various conditions refl ected their specifi c roles during abiotic or biotic stresses.Heterologous expression of a novel A.sinensis sesquiterpene synthase gene,AsTPS2,in Escherichia coli produced a major humulene product,so AsTPS2 is renamed AsHS1.AsHS1 is diff erent from ASS1,AsSesTPS,and AsVS,for mainly producingα-humulene.Based on the predicted space conformation of the AsHS1 model,the small ligand molecule may bind to the free amino acid by hydrogen bonding for the catalytic function of the enzyme,while the substrate farnesyl diphosphate(FPP)probably binds to the free amino acid on one side of the RxR motif.Arg450,Asp453,Asp454,Thr457,and Glu461 from the NSE/DTE motif and D307 and D311 from the DDxxD motif were found to form a polar interaction with two Mg2+clusters by docking.The Mg2+-bound DDxxD and NSE/DTE motifs and the free RXR motif are jointly directed into the catalytic pocket of AsHS1.Comparison of the tertiary structural models of AsHS1 with ASS1 showed that they diff ered in structures in several positions,such as surrounding the secondary catalytic pocket,which may lead to diff erences in catalytic products.Based on the results,biosynthetic pathways for specifi c sesquiterpenes such asα-humulene in A.sinensis are proposed.This study provides novel insights into the functions of the sesquiterpene synthases of A.sinensis and enriches knowledge on agarwood formation.展开更多
A new sesquiterpene lactone, strychnilactone (1), together with five known sesquiterpenoids, linderane (2), lindenenol (3), linderalactone (4), hydroxylindestenolide (5), pseudoneolinderane (6) have been isolated from...A new sesquiterpene lactone, strychnilactone (1), together with five known sesquiterpenoids, linderane (2), lindenenol (3), linderalactone (4), hydroxylindestenolide (5), pseudoneolinderane (6) have been isolated from the extracts of Supercritical Fluid Extraction of Lindera strychnifolia. The structure of the new compound was elucidated by means of spectroscopic analysis. And the relative configuration of 1 was assigned on the basis of NOE analysis.展开更多
基金financially supported by the National Key Research and Development Program of China(Program No.:2018YFC1706402)the National Natural Science Foundation of China(Grant No.:82003912)the 2022 Young Qihuang Scholars Cultivation Program(Program No.:256[2022])from the Human Resources and Education Department of the National Administration of Traditional Chinese Medicine.
摘要As important sources of new drugs,natural products(NPs)are conceptually biosynthesized from simple structural pioneers(i.e.building blocks).The traditional non-targeted purification strategy extensively suffers from the time-consuming and laborious bottlenecks.Fortunately,liquid chromatography–mass spectrometry/mass spectrometry(LC–MS/MS)-guided separations widely succeed in recent decades.However,it is still challenging for LC–MS/MS to precisely capture new NPs.Efficiently extracting information from the chaotic chemical composition and confident structural annotation are two primary technical barriers for pursuing the interesting structures,particularly those exhibiting trace distributions and high-level structural complexity.Here,to provide accurate guidance for the follow-up phytochemical purification,molecular defect filtering(MDF)and feature-based molecular networking(FBMN)[1]were incorporated to explore NPs and thereafter,bottom-up structural analysis was undertaken through identifying building blocks with full exciting energy ramp(FEER)-MS 3 matching.Sesquiterpene-chromone hybrids(SCHs)structurally configured by two building blocks such as units A(chromone)and B(sesquiterpene)[2]in agarwood were characterized as a proof-of-concept.Twenty-five SCHs were captured and identified.Thereof,seven new SCHs were purified with a LC–MS/MS-guided manner and annotated using nuclear magnetic resonance(NMR)spectroscopy to justify the proposed structures.Moreover,their cell-protective and anti-inflammatory activities were evaluated.Together,the incorporation of post-acquisition data processing strategies and FEER-MS 3 spectrum matchingassisted building blocks identification facilitated novel NPs exploration and purification.
摘要Traumatic axonal lesions of peripheral nerves disrupt neuronal connections with their targets,resulting in the loss of motor and sensory functions.Despite the peripheral nervous system’s capacity for axonal regrowth,this may lead to permanent impairements resulting in a loss of quality of life and a high socioeconomic burden.
基金National Natural Science Foundation of China,22177138,Ji-Kai LiuFundamental Research Funds for the Central Universities,South-Central Minzu University,PTZ25025,Heping Chen
摘要The Tiger Milk mushrooms(Lignosus spp.)have long been used as traditional folk medicines throughout Southeast Asia.However,the chemical constituents of these species remain largely unexplored.In this study,four type Ⅰ sesquit-erpene synthases(LrhTS1-LrhTS4)from Lignosus rhinocerusTM02® were functionally characterized through genome mining,in vitro enzymatic assays,and heterologous expression in an Escherichia coli host engineered to overexpress an exogenous mevalonate pathway.The enzyme products were analyzed by GC-MS and further purified and struc-turally elucidated by NMR spectroscopy.A total of 11 sesquiterpenes(1-11)were identified,among which two were unstable and converted to stable derivatives(2 to 2a and 7 to 7a).Notably,compounds 1-10 are reported from the genus Lignosus for the first time.LrhTS1 and LrhTS3 exhibited high catalytic specificity,whereas LrhTS2 and LrhTS4 displayed product promiscuity.This work expands the knowledge of terpene synthase from mushroom,and advances the understanding of the chemical basis underlying the bioactivity of the Lignosus rhinocerus TM02®.
基金supported by Innovation Team and Talents Cultivation Program of National Administration of Traditional Chinese Medicine(No:ZYYCXTD-D-202209)State Key Laboratory of Southwestern Chinese Medicine Resources(SKLTCM202311).
摘要The Asteraceae family,one of the largest angiosperm families,is rich in terpenoid secondary metabolites with significant medicinal value.Asteraceae plants have evolved a diverse array of terpenoid biosynthesis pathways,reflecting their adaptive significance and complex regulatory mechanisms.However,the evolutionary patterns and transcriptional regulatory mechanisms governing these biosynthetic processes remain unclear.This study investigates the evolution and transcriptional regulation of terpenoid biosynthesis genes in Asteraceae.Comparative genomic analysis of 19 Asteraceae and six out-group species revealed that Asteraceae species diverged~74.03 million years ago and were distinctly divided into three subfamilies.A total of 1714 terpene synthase(TPS)genes were identified,predominantly in the TPS-a and TPS-b subfamilies.Caryophyllene-type sesquiterpene biosynthetic gene clusters(BGCs)were detected in 10 species,with their formation due to whole-genome duplication(WGD)and tandem duplication.By integrating weighted gene coexpression network analysis(WGCNA)and machine learning methods,key transcription factors regulating caryophyllene synthase(CPS)in Carthamus tinctorius were identified.A multilayered gene regulatory network was constructed to identify potential regulatory factors involved in TPS gene regulation under light stress.By exploring the evolutionary patterns and potential regulatory relationships involved in terpenoid biosynthesis in Asteraceae,this study provides important insights into TPS gene evolution.In addition,the findings also offer guidance for optimizing genetic engineering strategies in terpenoid-based drug development.
基金Financial support for this work was provided by the National Natural Science Foundation of China(Nos.22171146,21971121,and 22188101)the Fundamental Research Funds for the Central Universities,Nankai University(No.63231199)the State Key Laboratory of Medicinal Chemical Biology。
摘要The first total synthesis of marine sesquiterpene(hydro)quinone meroterpenoids dysideanones A and E–G(1 and 4–6)has been accomplished in an enantioselective and divergent way.The sesquiterpene fragment and the aromatic moiety were efficiently connected via a site-selective and diastereoselective intermolecular alkylation of Wieland–Miescher ketone derivative 9 and benzyl bromide 10.The core 6/6/6/6-fused backbone of dysideanones was efficiently constructed through an intramolecular radical cyclization reaction.Dysideanone G(6)was easily prepared on a gram-scale and dysideanones A,E,and F(1,4,and 5)were divergently transformed from dysideanone G(6)in one or two steps.
摘要A rare sesquiterpene of hawkteasesquioid A(1),featuring a novel 5/6/5 tricyclic system containing a 6,5-spiroketal motif,was isolated from the bark of Litsea coreana Lévl.var.lanuginosa(hawk tea).The structure of this compound was elucidated based on the high-resolution electrospray ionization mass spectrometry(HRESIMS),one-dimensional(1D)and two-dimensional(2D)nuclear magnetic resonance(NMR)spectroscopy,and single-crystal X-ray diffraction data.The cytotoxicity of this compound was assessed on the A549,HT-29,and SW1990 cell lines.
基金financed by ONR Global[Grant N62909-21-1-2052,USA]CONICET[grant number PIP-CONICET 2022-2024,11220200101065CO]+2 种基金ANPCyT[grant numbers PICT 2020-SERIEA-02162(2022-2025)PICT 2020-SERIEA-3702(2022-2024)]SeCyT-UNC[grant number 2023-CONSOLIDAR-33620230100785CB01].
摘要Antimicrobial resistance is one of the most pressing global health challenges,as many pathogens are rapidly evolv-ing to evade existing treatments.Despite this urgent need for new solutions,natural plant-derived compounds remain relatively underexplored in the development of antimicrobial drugs.This report highlights an innovative approach to discovering potent antimicrobial agents through bioguided fractionation of numerous plant species from the rich Argentinean flora.By systematically screening 60 species(over 177 extracts)for antimicrobial activity against representative strains of gram-positive and gram-negative bacteria,we identified promising bioactive com-pounds within the Asteraceae family-particularly sesquiterpene lactones from the Xanthium genus.Building on this basis,we synthesized semi-synthetic derivatives by chemically modifying plant sub-extracts,focusing on structures incorporating heteroatoms and/or heterocycles containing oxygen and nitrogen(important for the bioavailability and bioactivity that they are capable of providing).These modifications were evaluated fortheir potential to enhance antimicrobial efficacy against bacteria and Candida species,including resistant strains.Our findings suggest that tai-loring natural metabolites from Xanthium and related Asteraceae species can significantly improve their antimicrobial properties.This strategy offers a promising pathway for the development of novel therapeutic agents to combat bacterial and fungal infections in an era of rising drug resistance.
基金supported by the Natural Science Foundation of Yunnan Education Department(No.02ZY018)Natural Science Foundation of Yunnan University(No.2003Q010A),which are grateful acknowledged.
摘要A new sesquiterpene lactone,Ainsliaolide A,was isolated from Ainsliaea bonatii.The structure was determined on the basis of spectral data.
基金National Natural Science Foundation of China(NSFC,Grant No.81373294)National Key Technology R&D Program"New Drug Innovation"of China(Grant No.2018ZX09711001-008-003)
摘要A phytochemical investigation on the aerial parts of Artemisia giraldii var. longipedunculata led to the isolation of 10 known sesquiterpenes, including 12-hydroxy-α-cyperone(1), 1β,6α-dihydroxyeudesma-4(15)-ene(2), carainterol A(3), oplodiol(4), douglanin(5), 1α-hydroxyisodauc-4-en-15-al(6), 3α,6α-dihydroxybisabola-4,10-diene(7), 4α,5β-dihydroxybisabola-2,10-diene(8), opposit-4(15)-ene-1β,7-diol(9), and saniculamoid D(10), respectively. Their structures were elucidated by analysis of the MS and NMR spectroscopic data and comparison with the literature. All the isolates were obtained from A. giraldii var. longipedunculata for the first time, and five of them were obtained from the genus Artemisia for the first time. Additionally, the 13 C NMR data of 1 were fully assigned based on the 2 D NMR data for the first time.
基金supported in part by the Natural Science Foundation of Tianjin(No.06YFJMJC15800),China.
摘要A new sesquiterpene, named vladimenal (1), was isolated from the roots of Vladimiria souliei. The structure was elucidated on the basis of spectroscopic analysis.
基金supported by the Natural Science Foundation of Fujian Province,China(No. 2009J01103).
摘要Three new sesquiterpene alkaloids,1-desacetylwilforgine(1),1-desacetylwilforine(2),and 9′-hydroxy-2-nicotinoylwilforine (3) were isolated from the roots of Tripterygium wilfordii Hook f.,along with six known alkaloids.Their structures were established on the basis of spectral analysis.
摘要A protoilludane sesquiterpene (named xanthocerapene) was isolated from the wood of Xanthoceras sorbifolia Bunge. Its structure, including the relative configuration was established by spectroscopic and chemical methods.
摘要A new sesquiterpene, 12,13-di-acetoxyl-1,4,6,11-eudesmanetetrol 1, was isolated from Michelia yunnanensis. The structure was elucidated on the basis of spectral data.
摘要A new sesquiterpene polyol ester, angulatin D, has been isolated from the root bark of Celastrus angulatus. The chemical structure is elucidated on the basis of spectral analysis.
摘要Two new beta-dihydroagarofuran sesquiterpenes were isolated from Euonymus phellomana Loes. and their structures were established on the basis of spectral analysis.
摘要A new sesquiterpene polyol ester was isolated from the leaves of Celastrus angulatus. Its structure was determined as 1 (beta), 2 (beta), 9 (a) -triacetoxy-8 (a) -((a) -hydroxyl-isobutyryloxy)-15-benzoyloxy-4 (a) -hydroxy-dihydroagarofuran by means of NMR, MS and IR spectral analysis. Preliminary biological study on antitumor activity revealed that this compound showed strong nonselective cytotoxicity against four of the NCI panel cell lines.
基金supported by the International Partnership Program of Chinese Academy of Sciences(No.153631KYSB20160004)the National Natural Science Foundation of China(Nos.81573305 and 81673327)the Ministry of Education and Science of the Republic of Kazakhstan(0118PK00458)
摘要One new dimeric(1) and two monomeric sesquiterpene lactones(5 and 13), together with 10 known compounds(2-4, 6-12), were isolated from Artemisia heptapotamica collected in Almaty region of Kazakhstan. All compounds were isolated from this plant for the first time. The structures of the new compounds were mainly achieved by extensive analysis of MS, 1D and 2D NMR spectroscopic data, and ECD spectrum as well. The inhibitory activities of all isolates against activation of NF-κB induced by LPS were assessed on a THP1-Dual cell model. Some of them showed strong inhibitory activity with IC50 values ranging from 2 to 25μmol·L^-1.
基金supported by Yunnan Provincial Science and Technology Department(Nos.2017ZF003-04 and 2015HB093)the Guangxi Natural Science Foundation(No.2017GXNSFBA198033)the Guibei Characteristic Pharmaceutical Resources Research Center(No.KYA201905)
摘要Three new sesquiterpene glycosides with alloaromadendrane and ylangene-derived type aglycones,named dendrofindlayanosides A-C(1-3),one new cyclopacamphane type sesquiterpene named dendrofindlayanobilin A(4),together with five known compounds have been isolated from stems of Dendrobium findlayanum.Their structures were determined on the basis of spectroscopic and chemical methods.
基金supported by the National Natural Science Foundation of China(81773844).
摘要Sesquiterpenes are the major pharmacodynamic components of agarwood,a precious traditional Chinese medicine obtained from the resinous portions of Aquilaria sinensis trees that form in response to environmental stressors.To characterize the sesquiterpene synthases responsible for sesquiterpene production in A.sinensis,a bioinformatics analysis of the genome of A.sinensis identifi ed six new terpene synthase genes,and 16 sesquiterpene synthase genes were identifi ed as type TPS-a in a phylogenetic analysis.The expression patterns for eight of the sesquiterpene synthase genes after treatment with various hormones or hydrogen peroxide were analyzed by real-time quantitative PCR.The results suggest that 100μM methyl jasmonate,ethephon,(±)-abscisic acid or hydrogen peroxide could be eff ective short-term eff ectors to increase the expression of sesquiterpene synthase genes,while 1 mM methyl salicylate may have long-term eff ects on increasing the expression of specifi c sesquiterpene synthase genes(e.g.,As-SesTPS,AsVS,AsTPS12 and AsTPS29).The expression changes in these genes under various conditions refl ected their specifi c roles during abiotic or biotic stresses.Heterologous expression of a novel A.sinensis sesquiterpene synthase gene,AsTPS2,in Escherichia coli produced a major humulene product,so AsTPS2 is renamed AsHS1.AsHS1 is diff erent from ASS1,AsSesTPS,and AsVS,for mainly producingα-humulene.Based on the predicted space conformation of the AsHS1 model,the small ligand molecule may bind to the free amino acid by hydrogen bonding for the catalytic function of the enzyme,while the substrate farnesyl diphosphate(FPP)probably binds to the free amino acid on one side of the RxR motif.Arg450,Asp453,Asp454,Thr457,and Glu461 from the NSE/DTE motif and D307 and D311 from the DDxxD motif were found to form a polar interaction with two Mg2+clusters by docking.The Mg2+-bound DDxxD and NSE/DTE motifs and the free RXR motif are jointly directed into the catalytic pocket of AsHS1.Comparison of the tertiary structural models of AsHS1 with ASS1 showed that they diff ered in structures in several positions,such as surrounding the secondary catalytic pocket,which may lead to diff erences in catalytic products.Based on the results,biosynthetic pathways for specifi c sesquiterpenes such asα-humulene in A.sinensis are proposed.This study provides novel insights into the functions of the sesquiterpene synthases of A.sinensis and enriches knowledge on agarwood formation.
摘要A new sesquiterpene lactone, strychnilactone (1), together with five known sesquiterpenoids, linderane (2), lindenenol (3), linderalactone (4), hydroxylindestenolide (5), pseudoneolinderane (6) have been isolated from the extracts of Supercritical Fluid Extraction of Lindera strychnifolia. The structure of the new compound was elucidated by means of spectroscopic analysis. And the relative configuration of 1 was assigned on the basis of NOE analysis.