Four prenylated flavonoids compounds 1-4,named sinopodophyllines A-D,and a flavonoid glycoside(compound 13),sinopodophylliside A,together with 19 known compounds(compounds 5-12 and 14-24) were isolated from the fruits...Four prenylated flavonoids compounds 1-4,named sinopodophyllines A-D,and a flavonoid glycoside(compound 13),sinopodophylliside A,together with 19 known compounds(compounds 5-12 and 14-24) were isolated from the fruits of Sinopodophyllum hexandrum.The structures of new compounds were elucidated by extensive spectroscopic analysis,including HRESIMS,1D and 2D NMR.Compounds 1-6,9-11,and 14-17 were tested for their cytotoxicity against human breast-cancer T47 D,MCF-7 and MDA-MB-231 cells in vitro,and compounds 2,5,6,10 and 11 showed significant cytotoxicity(IC50 values < 10 μmol·L^(-1))against T47 D cells.展开更多
An efficient approach has been developed for the synthesis of naturally occurring prenylated chalcones viz. kanzonol C （1）, stipulin （2）, crotaorixin （3）, medicagenin （4）, licoagrochalcone A （5） and abyssino...An efficient approach has been developed for the synthesis of naturally occurring prenylated chalcones viz. kanzonol C （1）, stipulin （2）, crotaorixin （3）, medicagenin （4）, licoagrochalcone A （5） and abyssinone D （6） along with the pyranochalcones paratocarpin C （7）, anthyllisone （8） and 3-O-methylabyssinone A （9）. The key step of the synthesis is a Claisen-Schmidt condensation. Subsequently, their anti-inflammatory effects were investigated in lipopolysaccharides （LPSs）-induced RAW-264.7 macrophages. Of the synthesized chalcones, compounds 5 （IC50= 10.41 μmol[L）, 6 （IC50= 9.65 μmol/L） and 8 （IC50= 15.34 μmol/L） show remarkable activity with no cytotoxicity. Compound 9 （IC50 = 4.5 μmol/L） exhibits maximum （83.6%） nitric oxide （NO） inhibition, but shows slight cytotoxicity. The results reveal that the chalcones bearing the prenyl group at 3- and/or 5-position on ring A （acetophenone moiety）, i.e., 1-4 and 7 show weak, or no inhibition activity, whereas chalcones having the prenyl group only on ring B （aldehyde part）, i.e., 5, 6 and 8 show significant activity on the production of inflammatory mediated NO with no cytotoxicity.展开更多
Prenylated flavonoids are mainly distributed in Leguminosae and Moraceae plants, and they have been reported to possess various biological activities. Previously, we have reported a prenylated isoflavonoid, isoangusto...Prenylated flavonoids are mainly distributed in Leguminosae and Moraceae plants, and they have been reported to possess various biological activities. Previously, we have reported a prenylated isoflavonoid, isoangustone A（IAA） from licorice（Glycyrrhiza uralensis）, which induces apoptosis in colorectal cancer cells by disrupting mitochondrial functions. In the present study, we compared a group of flavonoids from licorice with IAA for their anti-proliferation activities and effects on intracellular signaling. The results indicated that the isoprenyl groups on the A and B rings, the hydroxyl groups at the ortho position of isoprenyl on A ring and the conjugated plane of C ring might contribute to the anti-cancer activity of prenylated flavonoids. Based on the above structure-activity relationship, we further identified four prenylated flavonoids with similar anti-cancer activities from licorice. Taken together, our present study established a preliminary structure-activity relationship of anti-cancer prenylated flavonoids, and our data provided important leading compounds from licorice, which deserved further research and development.展开更多
2-[3,5-Di-O-β-D-glucosyl-4-(3-methylbut-2-enyl)phenyl]benzofuran-6-ol,a new prenylated arylbenzofuran derivative was isolated from Morus alba L.Its structure was elucidated by various spectroscopic methods including ...2-[3,5-Di-O-β-D-glucosyl-4-(3-methylbut-2-enyl)phenyl]benzofuran-6-ol,a new prenylated arylbenzofuran derivative was isolated from Morus alba L.Its structure was elucidated by various spectroscopic methods including MS,~1H NMR,^(13)C NMR,DEPT,~1H-~1HCOSY,HMQC and HMBC.展开更多
In continuation of our chemical investigation on some medicinal plants of the genus Tephrosia, re-investigation of the methylenechloride/methanol （1：1） extract of the air-dried aerial part of Tephrosia apollinea af...In continuation of our chemical investigation on some medicinal plants of the genus Tephrosia, re-investigation of the methylenechloride/methanol （1：1） extract of the air-dried aerial part of Tephrosia apollinea afforded a new prenylated flavonoid 1, in addition to an aromatic ester, a sesquiterpene, a lignan and several known prenylated flavonoids. The structures were established by （^1H NMR, ^13C NMR, DEPT, ^1H-^1H COSY, HMQC, HMBC, NOESY and HRMS）. Relative configurations of 9 and 10 were confirmed by X-ray analysis.展开更多
Objective To study the chemical constituents from the root barks of Morus alba. Methods Various chromatographic techniques were used to separate the constituents and their structures were elucidated on the basis of ex...Objective To study the chemical constituents from the root barks of Morus alba. Methods Various chromatographic techniques were used to separate the constituents and their structures were elucidated on the basis of extensive spectroscopic interpretation. Results Six compounds were isolated from the root barks of M. alba. The structure of new compound, named as albafuran D（1）, was established together with known compounds sanggenon H（2）, kuwanon E（3）, kuwanon U（4）, kuwanon F（5）, and benzokuwanon E（6）. Conclusion Compound 1 is a new geranylated 2-arylbenzofuran.展开更多
Two new dihydroflavonoids were obtained from the traditional Chinese medicinal herb Patrinia villosa Juss. Their structures were elucidated as （2S）-5, 7, 2＇, 6＇-tetrahydroxy-6, 8-di （γ, γ-dimethylallyl） flavan...Two new dihydroflavonoids were obtained from the traditional Chinese medicinal herb Patrinia villosa Juss. Their structures were elucidated as （2S）-5, 7, 2＇, 6＇-tetrahydroxy-6, 8-di （γ, γ-dimethylallyl） flavanone （1） and （2S）-5, 7, 2＇, 6＇-tetrahydroxy-6-1avandulylated flavanone （2） by spectroscopic methods including UV, IR, HR-TOF-MS, 1D NMR and 2D NMR techniques.展开更多
Five new flavonoid derivatives,cajavolubones A-E(1-5),along with six known analogues(6-11)were isolated from Cajanus volubilis,and their structures were elucidated by spectroscopic analysis and quantum chemical calcul...Five new flavonoid derivatives,cajavolubones A-E(1-5),along with six known analogues(6-11)were isolated from Cajanus volubilis,and their structures were elucidated by spectroscopic analysis and quantum chemical calculations.Cajavolubones A and B(1 and 2)were identified as two geranylated chalcones.Cajavolubone C(3)was a prenylated flavone,while cajavolubones D and E(4 and 5)were two prenylated isoflavanones.Compounds 3,8,9 and 11 displayed cytotoxicity against HCT-116 cancer cell line.展开更多
In the present study,17 flavonoids,including 9 prenylated isoflavones,4 isoflavones,3 flavanones and 1 flavone,were isolated from the twigs and leaves of Erythrina variegata.By NMR spectroscopic means and comparision ...In the present study,17 flavonoids,including 9 prenylated isoflavones,4 isoflavones,3 flavanones and 1 flavone,were isolated from the twigs and leaves of Erythrina variegata.By NMR spectroscopic means and comparision with the data in the leteratures,their structures were elucidated to be euchrenone b10(1),senegalensin(2),erythrinin C(3),scandenone(4),osajin(5),alpinum isoflavone(6),isoerysenegalensein E(7),erysenegalensein E(8),diprenylgenistein(9),abyssinone V(10),abyssinone V 4′-methyl ether(11),4′,7-dihydroxyflavanone(12),3′,5,7-trihydroxy-4′-methoxyisoflavone(13),2′,4′,5,7-tetrahydroxyisoflavone(14),genistein(15),daidzein(16),and apigenin(17).Except for compounds 1,4-7,and 9-10,other compounds were isolated from E.variegata for the first time.展开更多
Six new prenylated flavonoid glycosides,including four new furan-flavonoid glycosides wushepimedoside A–D(1–4)and two new prenyl flavonoid derivatives wushepimedoside E–F(5–6),and one know analog epimedkoreside B(...Six new prenylated flavonoid glycosides,including four new furan-flavonoid glycosides wushepimedoside A–D(1–4)and two new prenyl flavonoid derivatives wushepimedoside E–F(5–6),and one know analog epimedkoreside B(7)were isolated from biotransformation products of the aerial parts of Epimedium wushanense.Their structures were elucidated according to comprehensive analysis of HR-MS and NMR spectroscopic data,and the absolute configurations were assigned using experimental and calculated electronic circular dichroism(ECD)data.The regulatory activity of compounds 1–7 on the production of testosterone in primary rat Leydig cells were investigated,and 4 and 5 exhibited testosterone production-promoting activities.Molecular docking analysis suggested that bioactive compounds 4 and 5 showed the stable binding with 3β-HSD and 4 also had good affinity with Cyp17A1,which suggested that these compounds may regulate testosterone production through stimulating the expression of the above two key proteins.展开更多
Objective To study the chemical constituents from the root barks of Cudrania cochinchinensis. Methods The chemical constituents were isolated and purified by silica gel column chromatography. The structures of the com...Objective To study the chemical constituents from the root barks of Cudrania cochinchinensis. Methods The chemical constituents were isolated and purified by silica gel column chromatography. The structures of the compounds were identified on the basis of spectral data(MS,1H-NMR,13C-NMR, and 2D NMR) and by the comparison of spectroscopic data with the reported values in the literatures. Results A new xanthone, 1,6,7-trihydroxy-4-(1,1-dimethylallyl)-3-methoxyxanthone(1) and a known prenylated xanthone 1,5,6-trihydroxy-4-(1,1-dimethylallyl)-3-methoxyxanthone(isocudraniaxanthone B, 2) were isolated from the root barks of C. cochinchinensis. Conclusion Compound 1 is a new prenylated xanthone. Isomers 1 and 2 are obtained from this plant for the first time.展开更多
A new prenylated dihydroflavonoid was obtained from the root of Dolichos tenuicaulis （Baker） Craib. The structure was elucidated as （2S）-5,2＇,6＇-trihydroxy-3＇″, 8-di （γ,γ-dimethyl-allyl）-2＇″, 2＇″-dimet...A new prenylated dihydroflavonoid was obtained from the root of Dolichos tenuicaulis （Baker） Craib. The structure was elucidated as （2S）-5,2＇,6＇-trihydroxy-3＇″, 8-di （γ,γ-dimethyl-allyl）-2＇″, 2＇″-dimethylpyrano-[5＇″,6＇″： 6,7]-2＇″″,4＇″″-cyclohexadiene-1 ＇″″-one-[2＇″″,3＇″″： 3＇,4＇]-flavanone, named dolichnin A, by spectroscopic methods including UV, IR, HR-EI-MS, 1D NMR and 2D NMR techniques, and subsequently, the anticancer activity of this compound to inhibit human cancer cells＇ growth including A549, BEL-7402, Hep-3B, SMMC7721, HT-29, MCF-7, SGC-7902, K562, A498 and PC3 cell lines by MTT method was evaluated in vitro.展开更多
Twenty prenylated flavonoids 1-20 were synthesized by glycoside hydrolysis, dehydrogenation, selective O-methylation, O-prenylation and Claisen rearrangement reaction, from abundant and inexpensive natural flavonoids ...Twenty prenylated flavonoids 1-20 were synthesized by glycoside hydrolysis, dehydrogenation, selective O-methylation, O-prenylation and Claisen rearrangement reaction, from abundant and inexpensive natural flavonoids naringin, hespiredin, quercetin and myricetin. Among them, 1-7, 10-15 and 17-20 are novel compounds, the natural product 3,3＇,4＇,7-tetramethoxy-8-prenyl-5-hydroxy flavonoid（16） was synthesized in a high yield. Their antiprolirative activities were evaluated in vitro on a panel of three human cancer cell lines（HeLa, HCC1954 and SK-OV-3）. The results show that most of the target compounds displayed moderate to potent antiprolirative activities against the three cancer cells with half maximal inhibitory concentration（ICs0） values from 0.49 μmol/L to 95.07 μmol/L. Among them, 3′,4′,7-trimethoxyl-5-hydroxyl-8-prenyl flavonoid（12） exhibited the strongest antiprolirative activity against the three cancer cells mentioned above with IC50 values of 0.91-7.08 μmol/L. 3′,7-Dimethoxy-5-O- prenyl flavone（6） and 3′,4′,7-trimethoxy-5-O-prenyl flavone（10） showed selective antiproliferative activity against HCC1954 cells with TC50 value of 0 49 and 5 .32μmol/L, respectively.展开更多
A new prenylated flavonol, maackiaflavonol, was isolated from the ethanol extract of the roots of Maackia tenuifolia. Its structure was elucidated as 7-hydrox-8-prenylflavonol by means of spectroscopic analysis (UV, ... A new prenylated flavonol, maackiaflavonol, was isolated from the ethanol extract of the roots of Maackia tenuifolia. Its structure was elucidated as 7-hydrox-8-prenylflavonol by means of spectroscopic analysis (UV, IR, MS, NMR and 1H-1H COSY) and confirmed by total synthesis.展开更多
Three new minor prenylated flavonoids,named macadenanthins A–C(1–3),together with three known ones(4–6),were isolated from the twigs of Macaranga adenantha.Their structures were elucidated on the basis of extensive...Three new minor prenylated flavonoids,named macadenanthins A–C(1–3),together with three known ones(4–6),were isolated from the twigs of Macaranga adenantha.Their structures were elucidated on the basis of extensive spectroscopic analysis including NMR,UV and MS.The prenyl moieties in compounds 1–3 were further modified by cyclization and hydroxylation.The new compounds were tested for their cytotoxicity against four cancer cell lines(MCF-7,Hep G2,Hela and P388)and showed IC50 values in the range of 13.76–22.27 lM.展开更多
Four hitherto unknown prenylated coumarins,namely 600-O-b-D-apiofuranosylapterin(1),40-O-isobutyroylpeguangxienin(2),6-(3-methyl-2-oxobutyroyl)-7-methoxycoumarin(3),and 6-hydroxycoumurrayin(4),were isolated from the ...Four hitherto unknown prenylated coumarins,namely 600-O-b-D-apiofuranosylapterin(1),40-O-isobutyroylpeguangxienin(2),6-(3-methyl-2-oxobutyroyl)-7-methoxycoumarin(3),and 6-hydroxycoumurrayin(4),were isolated from the ethanol extract of Heracleum stenopterum,Peucedanum praeruptorum,Clausena lansium,and Murraya paniculata,respectively.Their chemical structures were established on the basis of extensive spectroscopic analysis.Compound 2 exhibited in vitro cytotoxic activity against five human cancer cell lines(HL-60,A-549,SMMC-7721,MCF-7,and SW-480)with IC50 values ranging from 15.9 to 23.2μM.展开更多
8-Prenylnaringenin(8-PN)is a valuable medical phytoestrogen,which is a precursor to many prenylated flavonoids.How-ever,the availability of 8-PN is limited by inefficient prenyltransferases(PTs)and inadequate substrat...8-Prenylnaringenin(8-PN)is a valuable medical phytoestrogen,which is a precursor to many prenylated flavonoids.How-ever,the availability of 8-PN is limited by inefficient prenyltransferases(PTs)and inadequate substrate precursor levels in microbial chassis.First,six PTs from different sources and their truncated cognates were expressed in a(2S)-naringenin producing strain.Only SfN8DT-1 derived from Sophora flavescens and its truncated cognate,tSfN8DT-1,could synthe-size 8-PN.Second,tSfN8DT-1 was engineered by multiple sequence alignment and a mutant tSfN8DT-1^(Q12E)with greater catalytic activity was obtained.Third,key genes,tHMGR and IDI1,of the mevalonate(MVA)pathway were overexpressed using a copy number combinatorial strategy,which greatly improved 8-PN titer by 368.75%.Fourth,a predicted structure of tSfN8DT-1^(Q12E)was used for molecular docking and virtual saturation mutagenesis.Two key residues,P229 and N305,were identified and saturation mutagenesis on these two sites resulted in an improved mutant N305M.The best-performing mutant,tSfN8DT-1^(Q12EN305M),produced 49.35±0.05 mg/L(5.57±0.01 mg/g DCW)8-PN in a shaking flask.Finally,101.40±2.55 mg/L of 8-PN was obtained in a 5-L bioreactor,which is the greatest titer reported to date for 8-PN.This study combined metabolic engineering and protein engineering methods to enhance precursor supplements and improve the catalytic ability of SfN8DT-1.The production of 8-PN in Saccharomyces cerevisiae was greatly increased through these methods,which may provide a feasible strategy for the biosynthesis of prenylated flavonoids.展开更多
A new prenylated indole alkaloid 11,17-epi-mangrovamide A(1),a new natural occurring product,1,7-dihydroxy-6-methyl-8-hydroxymethyl-xanthone(2),two known alkaloids,mangrovamide A(3)and mangrovamide G(4),and four known...A new prenylated indole alkaloid 11,17-epi-mangrovamide A(1),a new natural occurring product,1,7-dihydroxy-6-methyl-8-hydroxymethyl-xanthone(2),two known alkaloids,mangrovamide A(3)and mangrovamide G(4),and four known polyketide derivatives(5–8)were isolated and identified from the cold-seep sediment derived fungal strain Talaromyces funiculosus SD-523.Their structures were elucidated by combination of nuclear magnetic resonance(NMR),high resolution electrospray ionization mass spectroscopy(HRESIMS),quantum chemical electronic circular dichroism(ECD),and DP4+probability analysis as well as by comparison of the data with literature reports.All isolated compounds were tested for antibacterial activities.展开更多
基金supported by Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine(No.2010JZ-W-01)Ministry of Education,PRC,and National Key Technology R&D Program“New Drug Innovation”of China(Nos.2009ZX09308-004,2013ZX09103002-006)
文摘Four prenylated flavonoids compounds 1-4,named sinopodophyllines A-D,and a flavonoid glycoside(compound 13),sinopodophylliside A,together with 19 known compounds(compounds 5-12 and 14-24) were isolated from the fruits of Sinopodophyllum hexandrum.The structures of new compounds were elucidated by extensive spectroscopic analysis,including HRESIMS,1D and 2D NMR.Compounds 1-6,9-11,and 14-17 were tested for their cytotoxicity against human breast-cancer T47 D,MCF-7 and MDA-MB-231 cells in vitro,and compounds 2,5,6,10 and 11 showed significant cytotoxicity(IC50 values < 10 μmol·L^(-1))against T47 D cells.
基金financially supported by Priority Research Centers Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. NRF-2009-0094071), South Korea
文摘An efficient approach has been developed for the synthesis of naturally occurring prenylated chalcones viz. kanzonol C （1）, stipulin （2）, crotaorixin （3）, medicagenin （4）, licoagrochalcone A （5） and abyssinone D （6） along with the pyranochalcones paratocarpin C （7）, anthyllisone （8） and 3-O-methylabyssinone A （9）. The key step of the synthesis is a Claisen-Schmidt condensation. Subsequently, their anti-inflammatory effects were investigated in lipopolysaccharides （LPSs）-induced RAW-264.7 macrophages. Of the synthesized chalcones, compounds 5 （IC50= 10.41 μmol[L）, 6 （IC50= 9.65 μmol/L） and 8 （IC50= 15.34 μmol/L） show remarkable activity with no cytotoxicity. Compound 9 （IC50 = 4.5 μmol/L） exhibits maximum （83.6%） nitric oxide （NO） inhibition, but shows slight cytotoxicity. The results reveal that the chalcones bearing the prenyl group at 3- and/or 5-position on ring A （acetophenone moiety）, i.e., 1-4 and 7 show weak, or no inhibition activity, whereas chalcones having the prenyl group only on ring B （aldehyde part）, i.e., 5, 6 and 8 show significant activity on the production of inflammatory mediated NO with no cytotoxicity.
基金National Natural Science Foundation of China(Grant No.81472657 and 81272468)
文摘Prenylated flavonoids are mainly distributed in Leguminosae and Moraceae plants, and they have been reported to possess various biological activities. Previously, we have reported a prenylated isoflavonoid, isoangustone A（IAA） from licorice（Glycyrrhiza uralensis）, which induces apoptosis in colorectal cancer cells by disrupting mitochondrial functions. In the present study, we compared a group of flavonoids from licorice with IAA for their anti-proliferation activities and effects on intracellular signaling. The results indicated that the isoprenyl groups on the A and B rings, the hydroxyl groups at the ortho position of isoprenyl on A ring and the conjugated plane of C ring might contribute to the anti-cancer activity of prenylated flavonoids. Based on the above structure-activity relationship, we further identified four prenylated flavonoids with similar anti-cancer activities from licorice. Taken together, our present study established a preliminary structure-activity relationship of anti-cancer prenylated flavonoids, and our data provided important leading compounds from licorice, which deserved further research and development.
基金supported by the Great Research Project of National Major New Drug Development(No. 2009ZX09102-110)
文摘2-[3,5-Di-O-β-D-glucosyl-4-(3-methylbut-2-enyl)phenyl]benzofuran-6-ol,a new prenylated arylbenzofuran derivative was isolated from Morus alba L.Its structure was elucidated by various spectroscopic methods including MS,~1H NMR,^(13)C NMR,DEPT,~1H-~1HCOSY,HMQC and HMBC.
文摘In continuation of our chemical investigation on some medicinal plants of the genus Tephrosia, re-investigation of the methylenechloride/methanol （1：1） extract of the air-dried aerial part of Tephrosia apollinea afforded a new prenylated flavonoid 1, in addition to an aromatic ester, a sesquiterpene, a lignan and several known prenylated flavonoids. The structures were established by （^1H NMR, ^13C NMR, DEPT, ^1H-^1H COSY, HMQC, HMBC, NOESY and HRMS）. Relative configurations of 9 and 10 were confirmed by X-ray analysis.
基金National Natural Science Foundation of China(31300293 and 81202584)General Project of Applied Foundation Research,Yunnan Province(2013FB067)+1 种基金Basic Research Project of Ministry of Science and Technology of China(2012FY110300)Major State Basic Research Development Program(2010CB951704)
文摘Objective To study the chemical constituents from the root barks of Morus alba. Methods Various chromatographic techniques were used to separate the constituents and their structures were elucidated on the basis of extensive spectroscopic interpretation. Results Six compounds were isolated from the root barks of M. alba. The structure of new compound, named as albafuran D（1）, was established together with known compounds sanggenon H（2）, kuwanon E（3）, kuwanon U（4）, kuwanon F（5）, and benzokuwanon E（6）. Conclusion Compound 1 is a new geranylated 2-arylbenzofuran.
文摘Two new dihydroflavonoids were obtained from the traditional Chinese medicinal herb Patrinia villosa Juss. Their structures were elucidated as （2S）-5, 7, 2＇, 6＇-tetrahydroxy-6, 8-di （γ, γ-dimethylallyl） flavanone （1） and （2S）-5, 7, 2＇, 6＇-tetrahydroxy-6-1avandulylated flavanone （2） by spectroscopic methods including UV, IR, HR-TOF-MS, 1D NMR and 2D NMR techniques.
基金supported by the National Natural Science Foundation of China(No.22177016)the Natural Science Foundation of Chongqing(No.cstc2020jcyj-msxmX0537)the Open Project of State Key Laboratory of Natural Medicines(No.SKLNMKF202011).
文摘Five new flavonoid derivatives,cajavolubones A-E(1-5),along with six known analogues(6-11)were isolated from Cajanus volubilis,and their structures were elucidated by spectroscopic analysis and quantum chemical calculations.Cajavolubones A and B(1 and 2)were identified as two geranylated chalcones.Cajavolubone C(3)was a prenylated flavone,while cajavolubones D and E(4 and 5)were two prenylated isoflavanones.Compounds 3,8,9 and 11 displayed cytotoxicity against HCT-116 cancer cell line.
基金National Natural Science Foundation of China(Grant No.32060099).
文摘In the present study,17 flavonoids,including 9 prenylated isoflavones,4 isoflavones,3 flavanones and 1 flavone,were isolated from the twigs and leaves of Erythrina variegata.By NMR spectroscopic means and comparision with the data in the leteratures,their structures were elucidated to be euchrenone b10(1),senegalensin(2),erythrinin C(3),scandenone(4),osajin(5),alpinum isoflavone(6),isoerysenegalensein E(7),erysenegalensein E(8),diprenylgenistein(9),abyssinone V(10),abyssinone V 4′-methyl ether(11),4′,7-dihydroxyflavanone(12),3′,5,7-trihydroxy-4′-methoxyisoflavone(13),2′,4′,5,7-tetrahydroxyisoflavone(14),genistein(15),daidzein(16),and apigenin(17).Except for compounds 1,4-7,and 9-10,other compounds were isolated from E.variegata for the first time.
基金supported by the National Science and Technology Major Project(No.2017ZX09301072)China Postdoctoral Science Foundation(No.2016M603041).
文摘Six new prenylated flavonoid glycosides,including four new furan-flavonoid glycosides wushepimedoside A–D(1–4)and two new prenyl flavonoid derivatives wushepimedoside E–F(5–6),and one know analog epimedkoreside B(7)were isolated from biotransformation products of the aerial parts of Epimedium wushanense.Their structures were elucidated according to comprehensive analysis of HR-MS and NMR spectroscopic data,and the absolute configurations were assigned using experimental and calculated electronic circular dichroism(ECD)data.The regulatory activity of compounds 1–7 on the production of testosterone in primary rat Leydig cells were investigated,and 4 and 5 exhibited testosterone production-promoting activities.Molecular docking analysis suggested that bioactive compounds 4 and 5 showed the stable binding with 3β-HSD and 4 also had good affinity with Cyp17A1,which suggested that these compounds may regulate testosterone production through stimulating the expression of the above two key proteins.
基金National Natural Science Foundation of China(81060261)Guangxi Natural Science Foundation(2012GXNSFAA053021)Guangxi Teachers Education University Science Research Funds(2011-4)
文摘Objective To study the chemical constituents from the root barks of Cudrania cochinchinensis. Methods The chemical constituents were isolated and purified by silica gel column chromatography. The structures of the compounds were identified on the basis of spectral data(MS,1H-NMR,13C-NMR, and 2D NMR) and by the comparison of spectroscopic data with the reported values in the literatures. Results A new xanthone, 1,6,7-trihydroxy-4-(1,1-dimethylallyl)-3-methoxyxanthone(1) and a known prenylated xanthone 1,5,6-trihydroxy-4-(1,1-dimethylallyl)-3-methoxyxanthone(isocudraniaxanthone B, 2) were isolated from the root barks of C. cochinchinensis. Conclusion Compound 1 is a new prenylated xanthone. Isomers 1 and 2 are obtained from this plant for the first time.
文摘A new prenylated dihydroflavonoid was obtained from the root of Dolichos tenuicaulis （Baker） Craib. The structure was elucidated as （2S）-5,2＇,6＇-trihydroxy-3＇″, 8-di （γ,γ-dimethyl-allyl）-2＇″, 2＇″-dimethylpyrano-[5＇″,6＇″： 6,7]-2＇″″,4＇″″-cyclohexadiene-1 ＇″″-one-[2＇″″,3＇″″： 3＇,4＇]-flavanone, named dolichnin A, by spectroscopic methods including UV, IR, HR-EI-MS, 1D NMR and 2D NMR techniques, and subsequently, the anticancer activity of this compound to inhibit human cancer cells＇ growth including A549, BEL-7402, Hep-3B, SMMC7721, HT-29, MCF-7, SGC-7902, K562, A498 and PC3 cell lines by MTT method was evaluated in vitro.
基金Supported by the National Natural Science Foundation of China（Nos.J1210040, 21173074）.
文摘Twenty prenylated flavonoids 1-20 were synthesized by glycoside hydrolysis, dehydrogenation, selective O-methylation, O-prenylation and Claisen rearrangement reaction, from abundant and inexpensive natural flavonoids naringin, hespiredin, quercetin and myricetin. Among them, 1-7, 10-15 and 17-20 are novel compounds, the natural product 3,3＇,4＇,7-tetramethoxy-8-prenyl-5-hydroxy flavonoid（16） was synthesized in a high yield. Their antiprolirative activities were evaluated in vitro on a panel of three human cancer cell lines（HeLa, HCC1954 and SK-OV-3）. The results show that most of the target compounds displayed moderate to potent antiprolirative activities against the three cancer cells with half maximal inhibitory concentration（ICs0） values from 0.49 μmol/L to 95.07 μmol/L. Among them, 3′,4′,7-trimethoxyl-5-hydroxyl-8-prenyl flavonoid（12） exhibited the strongest antiprolirative activity against the three cancer cells mentioned above with IC50 values of 0.91-7.08 μmol/L. 3′,7-Dimethoxy-5-O- prenyl flavone（6） and 3′,4′,7-trimethoxy-5-O-prenyl flavone（10） showed selective antiproliferative activity against HCC1954 cells with TC50 value of 0 49 and 5 .32μmol/L, respectively.
文摘 A new prenylated flavonol, maackiaflavonol, was isolated from the ethanol extract of the roots of Maackia tenuifolia. Its structure was elucidated as 7-hydrox-8-prenylflavonol by means of spectroscopic analysis (UV, IR, MS, NMR and 1H-1H COSY) and confirmed by total synthesis.
基金National Natural Science Foundation of China(31300293 and 81422046)General Project of Applied Foundation Research,Yunnan Province(2013FB067)+1 种基金Basic Research Project of Ministry of Science and Technology of China(2012FY110300)Major State Basic Research Development Program(2010CB951704).
文摘Three new minor prenylated flavonoids,named macadenanthins A–C(1–3),together with three known ones(4–6),were isolated from the twigs of Macaranga adenantha.Their structures were elucidated on the basis of extensive spectroscopic analysis including NMR,UV and MS.The prenyl moieties in compounds 1–3 were further modified by cyclization and hydroxylation.The new compounds were tested for their cytotoxicity against four cancer cell lines(MCF-7,Hep G2,Hela and P388)and showed IC50 values in the range of 13.76–22.27 lM.
文摘Four hitherto unknown prenylated coumarins,namely 600-O-b-D-apiofuranosylapterin(1),40-O-isobutyroylpeguangxienin(2),6-(3-methyl-2-oxobutyroyl)-7-methoxycoumarin(3),and 6-hydroxycoumurrayin(4),were isolated from the ethanol extract of Heracleum stenopterum,Peucedanum praeruptorum,Clausena lansium,and Murraya paniculata,respectively.Their chemical structures were established on the basis of extensive spectroscopic analysis.Compound 2 exhibited in vitro cytotoxic activity against five human cancer cell lines(HL-60,A-549,SMMC-7721,MCF-7,and SW-480)with IC50 values ranging from 15.9 to 23.2μM.
基金supported by the National Key Research and Development Program of China(2019YFA0904800)the National Science Fund for Excellent Young Scholars(21822806)the National Natural Science Foundation of China(21908078).
文摘8-Prenylnaringenin(8-PN)is a valuable medical phytoestrogen,which is a precursor to many prenylated flavonoids.How-ever,the availability of 8-PN is limited by inefficient prenyltransferases(PTs)and inadequate substrate precursor levels in microbial chassis.First,six PTs from different sources and their truncated cognates were expressed in a(2S)-naringenin producing strain.Only SfN8DT-1 derived from Sophora flavescens and its truncated cognate,tSfN8DT-1,could synthe-size 8-PN.Second,tSfN8DT-1 was engineered by multiple sequence alignment and a mutant tSfN8DT-1^(Q12E)with greater catalytic activity was obtained.Third,key genes,tHMGR and IDI1,of the mevalonate(MVA)pathway were overexpressed using a copy number combinatorial strategy,which greatly improved 8-PN titer by 368.75%.Fourth,a predicted structure of tSfN8DT-1^(Q12E)was used for molecular docking and virtual saturation mutagenesis.Two key residues,P229 and N305,were identified and saturation mutagenesis on these two sites resulted in an improved mutant N305M.The best-performing mutant,tSfN8DT-1^(Q12EN305M),produced 49.35±0.05 mg/L(5.57±0.01 mg/g DCW)8-PN in a shaking flask.Finally,101.40±2.55 mg/L of 8-PN was obtained in a 5-L bioreactor,which is the greatest titer reported to date for 8-PN.This study combined metabolic engineering and protein engineering methods to enhance precursor supplements and improve the catalytic ability of SfN8DT-1.The production of 8-PN in Saccharomyces cerevisiae was greatly increased through these methods,which may provide a feasible strategy for the biosynthesis of prenylated flavonoids.
基金Supported by the National Natural Science Foundation of China(No.U2006203)the National Natural Science Foundation of Jiangsu Province(No.BK20201211)the Senior User Project of R/V Kexue(No.KEXUE2020GZ02)。
文摘A new prenylated indole alkaloid 11,17-epi-mangrovamide A(1),a new natural occurring product,1,7-dihydroxy-6-methyl-8-hydroxymethyl-xanthone(2),two known alkaloids,mangrovamide A(3)and mangrovamide G(4),and four known polyketide derivatives(5–8)were isolated and identified from the cold-seep sediment derived fungal strain Talaromyces funiculosus SD-523.Their structures were elucidated by combination of nuclear magnetic resonance(NMR),high resolution electrospray ionization mass spectroscopy(HRESIMS),quantum chemical electronic circular dichroism(ECD),and DP4+probability analysis as well as by comparison of the data with literature reports.All isolated compounds were tested for antibacterial activities.
