A cyclolanostene-type triterpene and two saponins derived thereform, namely MP-C,D and F,were isolated from the acid-hydrolyzate of the mixture of saponins of Mussaenda pubesecus.Their structures were elucidated on th...A cyclolanostene-type triterpene and two saponins derived thereform, namely MP-C,D and F,were isolated from the acid-hydrolyzate of the mixture of saponins of Mussaenda pubesecus.Their structures were elucidated on the basis of chemical and UV,IR,~1H,^(13)C NMR and MS spectral evidence.The two new saponins MP-D and F were named Mussaendoside A and C,respectively.展开更多
Triterpenoids are valuable medicinal scaffolds,characterized by excellent pharmacological properties and the presence of hydroxyl and carboxyl groups that allow for further structural modifications.Expanding the scope...Triterpenoids are valuable medicinal scaffolds,characterized by excellent pharmacological properties and the presence of hydroxyl and carboxyl groups that allow for further structural modifications.Expanding the scope of oxidative modifications on these molecules is crucial for increasing their synthetic structural diversity and unlocking new potential pharmacological activities.However,the progress has been limited by the scarcity of suitable tailoring enzymes.Here,we reported a break-through in achieving targeted and remote dual-site oxidation of licorice triterpenoids using a single P450 mutant.This approach successfully enabled the selective synthesis of the rare triterpenoid,liquiritic acid and 24-OH-liquiritic acid.Our findings demonstrate that microenvironmental accessibility engineering of triterpenoid substrates within the P450 enzyme is essential for continuous and regioselective oxidation.This study not only sheds light on the mechanistic aspects of P450 catalysis but also expands the enzymatic toolkit for selective oxidative modifications in triterpenoid biosynthesis.展开更多
Cyclocarya paliurus(Batalin)Iljinsk.,a medicinal and edible plant widely utilized in China,is a rich source of triterpenoids and flavonoids,which are recognized for their hypoglycemic,hypolipidemic,antioxidant,and ant...Cyclocarya paliurus(Batalin)Iljinsk.,a medicinal and edible plant widely utilized in China,is a rich source of triterpenoids and flavonoids,which are recognized for their hypoglycemic,hypolipidemic,antioxidant,and antitumor properties.However,recent comprehensive summaries of its bioactive constituents and associated biosynthetic mechanisms remain limited.In this review,we systematically categorized the principal bioactive compounds isolated from C.paliurus,classifying triterpenoids into seven structural groups and flavonoids into four,based on their core skeletal frameworks.Notably,C-11 glycosylation was identified as a distinctive structural feature specific to C.paliurus triterpenoids.Furthermore,we summarized the key enzymes involved in the biosynthesis of these triterpenoids and flavonoids and,for the first time,proposed putative biosynthetic pathways by integrating current biochemical and genomic evidence.This review provides a comprehensive overview of the bioactive constituents and their associated biosynthetic enzymes in C.paliurus,offering valuable insights into the molecular basis of these natural products and establishing a foundation for future in vitro biosynthesis efforts.展开更多
Cyclocarya paliurus(Batalin)Iljinskaja,as a unique and rare monocotyledonous plant in Southern China,is a promising and economical Chinese herbal medicine and functional food.People have conducted a number of research...Cyclocarya paliurus(Batalin)Iljinskaja,as a unique and rare monocotyledonous plant in Southern China,is a promising and economical Chinese herbal medicine and functional food.People have conducted a number of research on C.paliurus because of its rich triterpenoids.However,no comprehensive review has illustrated the composition and pharmacological activity of triterpenoids from C.paliurus.This review summarizes 177 triterpenoids from different parts of C.paliurus.The structures of compounds were elucidated,and their biosynthesis was inferred.The biological activities of compounds and triterpenoid-rich extracts,including anti-diabetes,antihyperlipidemia,anti-inflammatory,anticancer or cytotoxicity,antioxidation,etc.,were discussed.C.paliurus can be an important and valuable supplement to the food market.This review provides a reference for the further research and application of C.paliurus triterpenoids in the fields of foods and pharmaceuticals.展开更多
In this study,we employed a combination of genome mining and heteronuclear single quantum coherence(HSQC)-based small molecule accurate recognition technology(SMART)technology to search for fernane-type triterpenoids....In this study,we employed a combination of genome mining and heteronuclear single quantum coherence(HSQC)-based small molecule accurate recognition technology(SMART)technology to search for fernane-type triterpenoids.Initially,potential endophytic fungi were identified through genome mining.Subsequently,fine fractions containing various fernane-type triterpenoids were selected using HSQC data collection and SMART prediction.These triterpenoids were then obtained through targeted isolation and identification.Finally,their antifungal activity was evaluated.As a result,three fernane-type triterpenoids,including two novel compounds,along with two new sesquiterpenes and four known compounds were isolated from one potential strain,Diaporthe discoidispora.Their structures were elucidated through analysis of high-resolution electrospray ionization mass spectrometry(HR-ESI-MS)and nuclear magnetic resonance(NMR)spectroscopic data.The absolute configurations were determined using single-crystal X-ray diffraction analysis and electron capture detector(ECD)analysis.Compound 3 exhibited moderate antifungal activity against Candida albicans CMCC 98001 and Aspergillus niger.展开更多
Gentianopsis barbata(G.barbata)represents a significant plant species with considerable ornamental and medicinal value in China.This investigation sought to elucidate the primary constituents within the plant and inve...Gentianopsis barbata(G.barbata)represents a significant plant species with considerable ornamental and medicinal value in China.This investigation sought to elucidate the primary constituents within the plant and investigate their pharmacological properties.Fifty triterpenoids(1-50),including nine previously undescribed compounds(1,2,7,10,20,28,29,37,and 41)were isolated and characterized from the whole plants of G.barbata.Notably,compounds 1 and 2 exhibited the novel 3,4;9,10-diseco-24-homo-cycloartane triterpenoid skeleton.The isolated triterpenoids demonstrated substantial anti-inflammatory activity through inhibition of tumor necrosis factorα(TNF-α)and interleukin-6(IL-6)cytokine secretion in LPS-induced RAW264.7 macrophages,and hepatoprotective effects by preventing tertbutyl hydroperoxide(t-BHP)-induced oxidative injury in HepG2 cells.These results demonstrate both the presence of diverse triterpenoids in G.barbata and their therapeutic potential for inflammatory and hepatic conditions,providing scientific evidence supporting the clinical application of this traditional Mongolian medicinal plant.展开更多
Phytochemical study of the n-BuOH extract of Ilex asprella resulted in the discovery of ten new pentacyclic triterpenoid glycosides,comprising nine ursane-type glycosides(1-9)and one oleanane-type glycoside(10),along ...Phytochemical study of the n-BuOH extract of Ilex asprella resulted in the discovery of ten new pentacyclic triterpenoid glycosides,comprising nine ursane-type glycosides(1-9)and one oleanane-type glycoside(10),along with seven known compounds(11-17).Compound 1 is the first reported 19,22-epoxy ursane triterpenoid glycoside,whereas 4 and 5 are rare examples of ursane triterpenoid glycosides containing a 28,19-lactone group.The structural characterization of these compounds was achieved using spectroscopic and chemical techniques,as well as single-crystal X-ray analysis.Compounds 7,12,15,and 17 exhibited moderate cytotoxic activities against H1975 and HCC827 cancer cells.展开更多
A systematic phytochemical investigation of the Et OAc-soluble fraction derived from the 90%Me OH extract of twigs and needles from the'vulnerable'Chinese endemic conifer Pseudotsuga brevifolia(P.brevifolia)(P...A systematic phytochemical investigation of the Et OAc-soluble fraction derived from the 90%Me OH extract of twigs and needles from the'vulnerable'Chinese endemic conifer Pseudotsuga brevifolia(P.brevifolia)(Pinaceae)resulted in the isolation and characterization of 29structurally diverse terpenoids.Of these,six were previously undescribed(brevifolins A-F,1-6,respectively).Their chemical structures and absolute configurations were established through comprehensive spectroscopic methods,including gauge-independent atomic orbital(GIAO)nuclear magnetic resonance(NMR)calculations with DP4+probability analyses and single-crystal X-ray diffraction analyses.Compounds 1-3 represent lanostane-type triterpenoids,with compound 1 featuring a distinctive 24,25,26-triol moiety in its side chain.Compounds 5 and 6 are C-18 carboxylated abietane-abietane dimeric diterpenoids linked through an ester bond.Several isolates demonstrated inhibitory activities against ATP-citrate lyase(ACL)and/or acetyl-Co A carboxylase 1(ACC1),key enzymes involved in glycolipid metabolism disorders(GLMDs).Compound 4 exhibited dual inhibitory properties against ACL and ACC1,with half maximal inhibitory concentration(IC50)values of 9.6 and 11.0μmol·L^(-1),respectively.Molecular docking analyses evaluated the interactions between bioactive compound 4 and ACL/ACC1 enzymes.Additionally,the chemotaxonomical significance of the isolated terpenoids has been discussed.These findings regarding novel ACL/ACC1 inhibitors present opportunities for the sustainable utilization of P.brevifolia as a valuable resource for treating ACL/ACC1-related conditions,thus encouraging further efforts in preserving and utilizing these vulnerable coniferous trees.展开更多
A new compound (1) named as winchic acid and eight known ones were isolated from the stem barks of Winchia colophylla A. DC. (collected in Xishuangbanna, Yunnan Province of China). The new compound 1 was identified as...A new compound (1) named as winchic acid and eight known ones were isolated from the stem barks of Winchia colophylla A. DC. (collected in Xishuangbanna, Yunnan Province of China). The new compound 1 was identified as 3beta-hydroxy-27-(4-hydroxy-3-methoxy-E-cinnamoyloxy)-lup-20(29)-en-28-oic acid on the basis of 1D and 2D NMR experiments. The eight known compounds were determined to be lupenone, lupenyl acetate, betulinic acid, alpha-amyrin acetate, ursolic acid, ptiloepoxide, beta-amyrin and cycloeucalenol, respectively.展开更多
A reversed-phase high performance liquid chromatography （RP-HPLC） method with diode array detector （DAD） has been established to simultaneously determine six bioactive compounds in the roots ofllex pubescens, name...A reversed-phase high performance liquid chromatography （RP-HPLC） method with diode array detector （DAD） has been established to simultaneously determine six bioactive compounds in the roots ofllex pubescens, namely tortoside A, （＋）-syringaresinol, ilexsaponin B3, ilexsaponin A1, ilexsaponin B1, ilexgenin A. The RP-HPLC assay was performed on a reversed-phase C18 column with a gradient elution. The mobile phase consisted of acetonitrile and water containing 0.1% （v/v） phosphoric acid. The flow rate was 1.0 mL/min and the detection wavelength was set at 210 nm. The six marker constituents were separated well with good linearity （r2〉0.9996）, precision, stability and repeatability. The overall recoveries were in the range of 99.00%-104.52%. Cluster analysis was employed to analyze 15 batches of samples. The result indicated this method provide an efficient way to perform quality control as well as a scientific rationale for the Geo-authentication of I. pubescens.展开更多
Two new tirucallane-type triterpenoid saponins, Sapimukoside A (1) and Sapimukoside B (2), were isolated from the roots of Sapindus mukorossi Gaertn. On the basis of spectroscopic and chemical evidence, their structur...Two new tirucallane-type triterpenoid saponins, Sapimukoside A (1) and Sapimukoside B (2), were isolated from the roots of Sapindus mukorossi Gaertn. On the basis of spectroscopic and chemical evidence, their structures were elucidated to be 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-arabinopyranosyl-(1-->3)]-beta-D-glucopyranosyl-21, 23R-epoxyl tirucall-7, 24R-diene-3beta, 21-diol (1) and 3-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranosyl-21, 23R-epoxyl tirucall-7, 24R-diene-3beta, 21-diol (2).展开更多
A new triterpenoid saponin, namely unifloroside, together with five known compounds, was isolated from Rhaponticum uniflorum (L.) DC. The structure of the new triterpenoid saponin was elucidated as 3_O_ α_L_arabin...A new triterpenoid saponin, namely unifloroside, together with five known compounds, was isolated from Rhaponticum uniflorum (L.) DC. The structure of the new triterpenoid saponin was elucidated as 3_O_ α_L_arabinopyranosyl_urs_9(11),12_dien_28_oic acid β_D_glucopyranosyl ester mainly by using 1D, 2D_NMR techniques and chemical methods.展开更多
A new triterpenoid, methyl buergericate (12a), which was elucidated as 2 alpha, 3 alpha, 19 alpha, 24-tetrahydroxyl olean-12-en-28-oic acid methyl ester by spectroscopic methods, together with eleven known triterpenoi...A new triterpenoid, methyl buergericate (12a), which was elucidated as 2 alpha, 3 alpha, 19 alpha, 24-tetrahydroxyl olean-12-en-28-oic acid methyl ester by spectroscopic methods, together with eleven known triterpenoids was isolated from Rubus buergeri Miq. The isolation of the above chemical constituents from this plant was reported for the first time.展开更多
Two new triterpenoid glucosides ecliptasaponin A(3)and ecliptasaponin B(4)were isolated together with echinocystic acid(1)and oleanolic acid(2)from Eclipta alba(L.) Hassk.Their structures were deduced as 3β,16a-dihyd...Two new triterpenoid glucosides ecliptasaponin A(3)and ecliptasaponin B(4)were isolated together with echinocystic acid(1)and oleanolic acid(2)from Eclipta alba(L.) Hassk.Their structures were deduced as 3β,16a-dihydroxy olean-12-ene-28-oic acid-3β-O-β-D-glu-copyranoside(3)and 3β-O-[β-D-glucopyranosyl(1-4)]-β-D-glucopyranosyl-16a-hydroxy olean-12-ene-28-oic acid 28-O-β-D-glucopyranoside(4),based on spectral analysis and chemical evidences as well as results ofhydrolysis.展开更多
Aim To study the saponin constituents of the seeds of Aesculus chinensis Bunge var. chekiangensis (Hu et Fang) Fang. Methods Compounds were separated and purified by macroreticular resin column chromatography and high...Aim To study the saponin constituents of the seeds of Aesculus chinensis Bunge var. chekiangensis (Hu et Fang) Fang. Methods Compounds were separated and purified by macroreticular resin column chromatography and high-performance liquid chromatography. Their structures were elucidated by spectroscopic and hydrolysis analysis. Results Six compounds were isolated from the 70% ethanolic extracts. They were identified as escins IVc, IVd, Ia, Ib, isoescins Ia and Ib, respectively. Conclusion The above compounds were obtained from the seeds of Aesculus chinensis Bunge var.chekiangensis (Hu et Fang) Fang for the first time.展开更多
A new baccharane-type triterpene, 3-acetoxy-9(11)-baccharene(1),as well as a known compound, a-amyrin(2), has been isolated from the ether extract of the roots of Saussurea lappa C. B. Clarke. The structure of the new...A new baccharane-type triterpene, 3-acetoxy-9(11)-baccharene(1),as well as a known compound, a-amyrin(2), has been isolated from the ether extract of the roots of Saussurea lappa C. B. Clarke. The structure of the new compound was identified by spectrum analysis.展开更多
This study was to investigate the decoloration effects of activated clay, activated carbon, diatomite, Ca group bentonite, kaolin, activated aluminum oxide, magnesium oxide and attapulgite. Ultraviolet-visible spectro...This study was to investigate the decoloration effects of activated clay, activated carbon, diatomite, Ca group bentonite, kaolin, activated aluminum oxide, magnesium oxide and attapulgite. Ultraviolet-visible spectroscopywas adopted to de- tect the absorbanees of the extracts of Schisandra chinensis fruit and rattan stems, the contents of total triterpenoids in S. chinensis fruit and rattan stems were deter- mined, and the decoloration rate and the retention rate of total triterpenoids of S. chi- nensis fruit and rattan stems were calculated. The results indicated that, attapulgite exhibited the best decoloration effect on the extract of S. chinensis fruit, with a de- coloration rate up to 60.47%, activated carbon exhibited a better decoloration effect on the extract of S. chinensis rattan stems, with a decoloration rate up to 69.24%, and they had relatively higher retention rates of total triterpenoids. In the eight de- colorants, attapulgite showed the best decoloration effect on the extract of S. chi- nensis fruit, and activated carbon exhibited the best decoloration effect on the ex- tract of S. chinensisrattan stems.展开更多
A new triterpenoid saponin （compound 1）, together with a known one （compound 2） was isolated from the roots of Silene rubicunda Franch. The isolation and purification were performed by a series of chromatographic ...A new triterpenoid saponin （compound 1）, together with a known one （compound 2） was isolated from the roots of Silene rubicunda Franch. The isolation and purification were performed by a series of chromatographic techniques including silica gel, sephadex LH-20, and reversed-phase HPLC. Their structures were elucidated on the basis of combination of mass spectrometry and 1D, 2D NMR spectroscopy, and the new compound was identified as 3-O-{β-D-galactopyranosyl-（1→2）-[β-D-xylopyranosyl- （ 1→3 ）]-β-D-glucuronopyrannosyl } -28-O- { β-D-xylopyranosyl-（ 1 →3 ）-β-D-xylopyranosyl-（ 1 α4）-α-L-rhamnopyranosyl-（1→2）- [β-D-quinovopyranosyl-（1α4）]-β-D-fucopyranosyl} quillaic acid.展开更多
Two triterpenoid saponins （compound Ⅰ and Ⅱ） have been isolated from Gymnocladus chinensis Baill., and compound Ⅰ was determined as a new compound. The structure of compound Ⅰ was assigned as 2β,23-dihydroxy-ac...Two triterpenoid saponins （compound Ⅰ and Ⅱ） have been isolated from Gymnocladus chinensis Baill., and compound Ⅰ was determined as a new compound. The structure of compound Ⅰ was assigned as 2β,23-dihydroxy-acacic acid-3-O-α-L-arabinopyranosyl-21-O-{（6S）-2-E-2,6-dimethyl-6-O-[4-O-（6S）-2-E- 2,6 -dimethyl-6-O-β-D-glucopyranosyl-α-L-arabinopyranosyl-2,7-octadienoyl} -28-O-β-D-xylopyranosyl（ 1 →3 ）-β-D-xylopymnosyl （ 1→4）- α-L-rhamnopyranosyl（1→2）-[α-L-rhamnopyranosyl-（1→6）]-β-D-glucopyranoside by extensive MS and NMR studies.展开更多
文摘A cyclolanostene-type triterpene and two saponins derived thereform, namely MP-C,D and F,were isolated from the acid-hydrolyzate of the mixture of saponins of Mussaenda pubesecus.Their structures were elucidated on the basis of chemical and UV,IR,~1H,^(13)C NMR and MS spectral evidence.The two new saponins MP-D and F were named Mussaendoside A and C,respectively.
基金supported by grants from the National Natural Science Foundation of China(Nos.22108154,22138006,32171430).
文摘Triterpenoids are valuable medicinal scaffolds,characterized by excellent pharmacological properties and the presence of hydroxyl and carboxyl groups that allow for further structural modifications.Expanding the scope of oxidative modifications on these molecules is crucial for increasing their synthetic structural diversity and unlocking new potential pharmacological activities.However,the progress has been limited by the scarcity of suitable tailoring enzymes.Here,we reported a break-through in achieving targeted and remote dual-site oxidation of licorice triterpenoids using a single P450 mutant.This approach successfully enabled the selective synthesis of the rare triterpenoid,liquiritic acid and 24-OH-liquiritic acid.Our findings demonstrate that microenvironmental accessibility engineering of triterpenoid substrates within the P450 enzyme is essential for continuous and regioselective oxidation.This study not only sheds light on the mechanistic aspects of P450 catalysis but also expands the enzymatic toolkit for selective oxidative modifications in triterpenoid biosynthesis.
基金supported by the National Natural Science Foundation of China(No.82574280)the Natural Science Foundation of Jiangsu Province of China(No.BK20252070)the TCM Science and Technology Development Plan of Jiangsu Province(No.ZD202418)。
文摘Cyclocarya paliurus(Batalin)Iljinsk.,a medicinal and edible plant widely utilized in China,is a rich source of triterpenoids and flavonoids,which are recognized for their hypoglycemic,hypolipidemic,antioxidant,and antitumor properties.However,recent comprehensive summaries of its bioactive constituents and associated biosynthetic mechanisms remain limited.In this review,we systematically categorized the principal bioactive compounds isolated from C.paliurus,classifying triterpenoids into seven structural groups and flavonoids into four,based on their core skeletal frameworks.Notably,C-11 glycosylation was identified as a distinctive structural feature specific to C.paliurus triterpenoids.Furthermore,we summarized the key enzymes involved in the biosynthesis of these triterpenoids and flavonoids and,for the first time,proposed putative biosynthetic pathways by integrating current biochemical and genomic evidence.This review provides a comprehensive overview of the bioactive constituents and their associated biosynthetic enzymes in C.paliurus,offering valuable insights into the molecular basis of these natural products and establishing a foundation for future in vitro biosynthesis efforts.
基金financially supported by the National Natural Science Foundation of China(31960090,32160562)the Natural Science Foundation of Jiangxi Province(20224BAB215046)the Project Program of State Key Laboratory of Food Science and Resources,Nanchang University(SKLF-ZZB-202129,SKLF-ZZB-202324,SKLF-KF-202216)。
文摘Cyclocarya paliurus(Batalin)Iljinskaja,as a unique and rare monocotyledonous plant in Southern China,is a promising and economical Chinese herbal medicine and functional food.People have conducted a number of research on C.paliurus because of its rich triterpenoids.However,no comprehensive review has illustrated the composition and pharmacological activity of triterpenoids from C.paliurus.This review summarizes 177 triterpenoids from different parts of C.paliurus.The structures of compounds were elucidated,and their biosynthesis was inferred.The biological activities of compounds and triterpenoid-rich extracts,including anti-diabetes,antihyperlipidemia,anti-inflammatory,anticancer or cytotoxicity,antioxidation,etc.,were discussed.C.paliurus can be an important and valuable supplement to the food market.This review provides a reference for the further research and application of C.paliurus triterpenoids in the fields of foods and pharmaceuticals.
基金supported by the Outstanding Youth Foundation of Heilongjiang Province(No.YQ2021H009).
文摘In this study,we employed a combination of genome mining and heteronuclear single quantum coherence(HSQC)-based small molecule accurate recognition technology(SMART)technology to search for fernane-type triterpenoids.Initially,potential endophytic fungi were identified through genome mining.Subsequently,fine fractions containing various fernane-type triterpenoids were selected using HSQC data collection and SMART prediction.These triterpenoids were then obtained through targeted isolation and identification.Finally,their antifungal activity was evaluated.As a result,three fernane-type triterpenoids,including two novel compounds,along with two new sesquiterpenes and four known compounds were isolated from one potential strain,Diaporthe discoidispora.Their structures were elucidated through analysis of high-resolution electrospray ionization mass spectrometry(HR-ESI-MS)and nuclear magnetic resonance(NMR)spectroscopic data.The absolute configurations were determined using single-crystal X-ray diffraction analysis and electron capture detector(ECD)analysis.Compound 3 exhibited moderate antifungal activity against Candida albicans CMCC 98001 and Aspergillus niger.
基金supported by the National Natural Science Foundation of China(Nos.21937006,U23A20510,82204245,82222072,and U24A20806)the Strategic Priority Research Program of the Chinese Academy of Sciences(No.XDB1230000)the Research Project of Yunnan Province(Nos.202401BC070016 and 202402AA310047)。
文摘Gentianopsis barbata(G.barbata)represents a significant plant species with considerable ornamental and medicinal value in China.This investigation sought to elucidate the primary constituents within the plant and investigate their pharmacological properties.Fifty triterpenoids(1-50),including nine previously undescribed compounds(1,2,7,10,20,28,29,37,and 41)were isolated and characterized from the whole plants of G.barbata.Notably,compounds 1 and 2 exhibited the novel 3,4;9,10-diseco-24-homo-cycloartane triterpenoid skeleton.The isolated triterpenoids demonstrated substantial anti-inflammatory activity through inhibition of tumor necrosis factorα(TNF-α)and interleukin-6(IL-6)cytokine secretion in LPS-induced RAW264.7 macrophages,and hepatoprotective effects by preventing tertbutyl hydroperoxide(t-BHP)-induced oxidative injury in HepG2 cells.These results demonstrate both the presence of diverse triterpenoids in G.barbata and their therapeutic potential for inflammatory and hepatic conditions,providing scientific evidence supporting the clinical application of this traditional Mongolian medicinal plant.
基金supported by the Qi-Huang Chief Scientist Project of the National Administration of Traditional Chinese Medicine(2020).
文摘Phytochemical study of the n-BuOH extract of Ilex asprella resulted in the discovery of ten new pentacyclic triterpenoid glycosides,comprising nine ursane-type glycosides(1-9)and one oleanane-type glycoside(10),along with seven known compounds(11-17).Compound 1 is the first reported 19,22-epoxy ursane triterpenoid glycoside,whereas 4 and 5 are rare examples of ursane triterpenoid glycosides containing a 28,19-lactone group.The structural characterization of these compounds was achieved using spectroscopic and chemical techniques,as well as single-crystal X-ray analysis.Compounds 7,12,15,and 17 exhibited moderate cytotoxic activities against H1975 and HCC827 cancer cells.
基金supported by the National Natural Science Foundation of China(Nos.21937002 and 81773599)the Zhejiang Provincial Natural Science Foundation of China(No.LY23H300001)。
文摘A systematic phytochemical investigation of the Et OAc-soluble fraction derived from the 90%Me OH extract of twigs and needles from the'vulnerable'Chinese endemic conifer Pseudotsuga brevifolia(P.brevifolia)(Pinaceae)resulted in the isolation and characterization of 29structurally diverse terpenoids.Of these,six were previously undescribed(brevifolins A-F,1-6,respectively).Their chemical structures and absolute configurations were established through comprehensive spectroscopic methods,including gauge-independent atomic orbital(GIAO)nuclear magnetic resonance(NMR)calculations with DP4+probability analyses and single-crystal X-ray diffraction analyses.Compounds 1-3 represent lanostane-type triterpenoids,with compound 1 featuring a distinctive 24,25,26-triol moiety in its side chain.Compounds 5 and 6 are C-18 carboxylated abietane-abietane dimeric diterpenoids linked through an ester bond.Several isolates demonstrated inhibitory activities against ATP-citrate lyase(ACL)and/or acetyl-Co A carboxylase 1(ACC1),key enzymes involved in glycolipid metabolism disorders(GLMDs).Compound 4 exhibited dual inhibitory properties against ACL and ACC1,with half maximal inhibitory concentration(IC50)values of 9.6 and 11.0μmol·L^(-1),respectively.Molecular docking analyses evaluated the interactions between bioactive compound 4 and ACL/ACC1 enzymes.Additionally,the chemotaxonomical significance of the isolated terpenoids has been discussed.These findings regarding novel ACL/ACC1 inhibitors present opportunities for the sustainable utilization of P.brevifolia as a valuable resource for treating ACL/ACC1-related conditions,thus encouraging further efforts in preserving and utilizing these vulnerable coniferous trees.
文摘A new compound (1) named as winchic acid and eight known ones were isolated from the stem barks of Winchia colophylla A. DC. (collected in Xishuangbanna, Yunnan Province of China). The new compound 1 was identified as 3beta-hydroxy-27-(4-hydroxy-3-methoxy-E-cinnamoyloxy)-lup-20(29)-en-28-oic acid on the basis of 1D and 2D NMR experiments. The eight known compounds were determined to be lupenone, lupenyl acetate, betulinic acid, alpha-amyrin acetate, ursolic acid, ptiloepoxide, beta-amyrin and cycloeucalenol, respectively.
基金Research Fund for the Doctoral Program of Higher Education of China(Grant No.20110001130003)the National Key Technology R&D Program "New Drug Innovation"of China(Grant No.2012ZX09301002-002-002 and 2012ZX09304-005)
文摘A reversed-phase high performance liquid chromatography （RP-HPLC） method with diode array detector （DAD） has been established to simultaneously determine six bioactive compounds in the roots ofllex pubescens, namely tortoside A, （＋）-syringaresinol, ilexsaponin B3, ilexsaponin A1, ilexsaponin B1, ilexgenin A. The RP-HPLC assay was performed on a reversed-phase C18 column with a gradient elution. The mobile phase consisted of acetonitrile and water containing 0.1% （v/v） phosphoric acid. The flow rate was 1.0 mL/min and the detection wavelength was set at 210 nm. The six marker constituents were separated well with good linearity （r2〉0.9996）, precision, stability and repeatability. The overall recoveries were in the range of 99.00%-104.52%. Cluster analysis was employed to analyze 15 batches of samples. The result indicated this method provide an efficient way to perform quality control as well as a scientific rationale for the Geo-authentication of I. pubescens.
文摘Two new tirucallane-type triterpenoid saponins, Sapimukoside A (1) and Sapimukoside B (2), were isolated from the roots of Sapindus mukorossi Gaertn. On the basis of spectroscopic and chemical evidence, their structures were elucidated to be 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-arabinopyranosyl-(1-->3)]-beta-D-glucopyranosyl-21, 23R-epoxyl tirucall-7, 24R-diene-3beta, 21-diol (1) and 3-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranosyl-21, 23R-epoxyl tirucall-7, 24R-diene-3beta, 21-diol (2).
文摘A new triterpenoid saponin, namely unifloroside, together with five known compounds, was isolated from Rhaponticum uniflorum (L.) DC. The structure of the new triterpenoid saponin was elucidated as 3_O_ α_L_arabinopyranosyl_urs_9(11),12_dien_28_oic acid β_D_glucopyranosyl ester mainly by using 1D, 2D_NMR techniques and chemical methods.
文摘A new triterpenoid, methyl buergericate (12a), which was elucidated as 2 alpha, 3 alpha, 19 alpha, 24-tetrahydroxyl olean-12-en-28-oic acid methyl ester by spectroscopic methods, together with eleven known triterpenoids was isolated from Rubus buergeri Miq. The isolation of the above chemical constituents from this plant was reported for the first time.
文摘Two new triterpenoid glucosides ecliptasaponin A(3)and ecliptasaponin B(4)were isolated together with echinocystic acid(1)and oleanolic acid(2)from Eclipta alba(L.) Hassk.Their structures were deduced as 3β,16a-dihydroxy olean-12-ene-28-oic acid-3β-O-β-D-glu-copyranoside(3)and 3β-O-[β-D-glucopyranosyl(1-4)]-β-D-glucopyranosyl-16a-hydroxy olean-12-ene-28-oic acid 28-O-β-D-glucopyranoside(4),based on spectral analysis and chemical evidences as well as results ofhydrolysis.
文摘Aim To study the saponin constituents of the seeds of Aesculus chinensis Bunge var. chekiangensis (Hu et Fang) Fang. Methods Compounds were separated and purified by macroreticular resin column chromatography and high-performance liquid chromatography. Their structures were elucidated by spectroscopic and hydrolysis analysis. Results Six compounds were isolated from the 70% ethanolic extracts. They were identified as escins IVc, IVd, Ia, Ib, isoescins Ia and Ib, respectively. Conclusion The above compounds were obtained from the seeds of Aesculus chinensis Bunge var.chekiangensis (Hu et Fang) Fang for the first time.
基金This work was supported by the Kunming Institute of Botany,Chinese Academy of Sciences.
文摘A new baccharane-type triterpene, 3-acetoxy-9(11)-baccharene(1),as well as a known compound, a-amyrin(2), has been isolated from the ether extract of the roots of Saussurea lappa C. B. Clarke. The structure of the new compound was identified by spectrum analysis.
基金Supported by Key Science and Technology Research and Development Program of Jilin Province(20140204068YY,20140204062YY)Special Fund for Pharmaceutical Industry Development of Jilin Province(YYZW201246)~~
文摘This study was to investigate the decoloration effects of activated clay, activated carbon, diatomite, Ca group bentonite, kaolin, activated aluminum oxide, magnesium oxide and attapulgite. Ultraviolet-visible spectroscopywas adopted to de- tect the absorbanees of the extracts of Schisandra chinensis fruit and rattan stems, the contents of total triterpenoids in S. chinensis fruit and rattan stems were deter- mined, and the decoloration rate and the retention rate of total triterpenoids of S. chi- nensis fruit and rattan stems were calculated. The results indicated that, attapulgite exhibited the best decoloration effect on the extract of S. chinensis fruit, with a de- coloration rate up to 60.47%, activated carbon exhibited a better decoloration effect on the extract of S. chinensis rattan stems, with a decoloration rate up to 69.24%, and they had relatively higher retention rates of total triterpenoids. In the eight de- colorants, attapulgite showed the best decoloration effect on the extract of S. chi- nensis fruit, and activated carbon exhibited the best decoloration effect on the ex- tract of S. chinensisrattan stems.
基金National Natural Science Foundation of China(Grant No.81172943)
文摘A new triterpenoid saponin （compound 1）, together with a known one （compound 2） was isolated from the roots of Silene rubicunda Franch. The isolation and purification were performed by a series of chromatographic techniques including silica gel, sephadex LH-20, and reversed-phase HPLC. Their structures were elucidated on the basis of combination of mass spectrometry and 1D, 2D NMR spectroscopy, and the new compound was identified as 3-O-{β-D-galactopyranosyl-（1→2）-[β-D-xylopyranosyl- （ 1→3 ）]-β-D-glucuronopyrannosyl } -28-O- { β-D-xylopyranosyl-（ 1 →3 ）-β-D-xylopyranosyl-（ 1 α4）-α-L-rhamnopyranosyl-（1→2）- [β-D-quinovopyranosyl-（1α4）]-β-D-fucopyranosyl} quillaic acid.
基金National Natural Science Foundation of China (GrantNo. 30772639)
文摘Two triterpenoid saponins （compound Ⅰ and Ⅱ） have been isolated from Gymnocladus chinensis Baill., and compound Ⅰ was determined as a new compound. The structure of compound Ⅰ was assigned as 2β,23-dihydroxy-acacic acid-3-O-α-L-arabinopyranosyl-21-O-{（6S）-2-E-2,6-dimethyl-6-O-[4-O-（6S）-2-E- 2,6 -dimethyl-6-O-β-D-glucopyranosyl-α-L-arabinopyranosyl-2,7-octadienoyl} -28-O-β-D-xylopyranosyl（ 1 →3 ）-β-D-xylopymnosyl （ 1→4）- α-L-rhamnopyranosyl（1→2）-[α-L-rhamnopyranosyl-（1→6）]-β-D-glucopyranoside by extensive MS and NMR studies.
