A new flavan-3-ol glucoside, (-)-afzelechin-7-O-β-D-glucopyranoside (1), has been isolated from the stem of Daphniphyllum oldhami. The structure of the new compound was elucidated on the basis of detailed spectroscop...A new flavan-3-ol glucoside, (-)-afzelechin-7-O-β-D-glucopyranoside (1), has been isolated from the stem of Daphniphyllum oldhami. The structure of the new compound was elucidated on the basis of detailed spectroscopie analysis and comparison with related compounds.展开更多
Further phytochemical investigation of the ethyl acetate extract of the stem of Daphniphyllum oldhamii afforded a new phenolic glucoside, named oldhamioside 1, together with eleven known compounds, koaburaside 2, betu...Further phytochemical investigation of the ethyl acetate extract of the stem of Daphniphyllum oldhamii afforded a new phenolic glucoside, named oldhamioside 1, together with eleven known compounds, koaburaside 2, betulin, 28-hydroxyl-3-lupenone, pineresinol, syringaresinol, 4-O-methyl- cedrusin, narigenin, eriodictyol, apigenin, loureirin C, and asperuloside. The structures of new and known compounds were characterized by detailed spectroscopic analysis and comparison of their spectral data with reported values.展开更多
Two new triterpene esters, 2-O-caffeoylalphitolic acid (1) and methyl 2-O-caffeoyl- alphitolate (2), together with two known triterpenes were isolated from the shrub Daphniphyllum oldhami. The structures of new compou...Two new triterpene esters, 2-O-caffeoylalphitolic acid (1) and methyl 2-O-caffeoyl- alphitolate (2), together with two known triterpenes were isolated from the shrub Daphniphyllum oldhami. The structures of new compounds were elucidated on the basis of detailed spectroscopic analysis and compared with related compound.展开更多
Two new daphnicyclidin-type Daphniphyllum alkaloids,daphmacrodins A and B(1 and 2)were isolated from the leaves and stems of Daphniphyllum macropodum.Their structures were elucidated by extensive spectroscopic techniq...Two new daphnicyclidin-type Daphniphyllum alkaloids,daphmacrodins A and B(1 and 2)were isolated from the leaves and stems of Daphniphyllum macropodum.Their structures were elucidated by extensive spectroscopic techniques,including 2D NMR spectroscopy and mass spectrometry.The relative configuration of 1 was further confirmed by a single-crystal X-ray diffraction analysis.Their cytotoxic activities against five human cancer cell lines,pesticidal activities against brine shrimp(Artemia salina),and antibacterial activities against five standard bacterial and fungal strains were evaluated.The structure of 1 was successfully transformed to 2 by a chemical method.展开更多
One new Daphniphyllum alkaloid,daphnioldhanol A(1),together with three known ones,were isolated from the stem part of Daphniphyllum angustifolium Hutch.Their structures were elucidated by spectroscopic methods and com...One new Daphniphyllum alkaloid,daphnioldhanol A(1),together with three known ones,were isolated from the stem part of Daphniphyllum angustifolium Hutch.Their structures were elucidated by spectroscopic methods and comparing with the literature data.Compound 2 is a new natural product,but known by synthesis as a racemate.Compound 1 exhibited week cytotoxic activity against Hela cell line with IC50 of 31.9μM.展开更多
Fivenovel Daphniphyllum alkaloids,named dcalycinumines A-E(1-4,6),andeight previously described Daphniphyllum alkaloids(5,7-13)were isolated from Daphniphyllum calycinum.Compound 1 is the first Daphniphyllum alkaloid ...Fivenovel Daphniphyllum alkaloids,named dcalycinumines A-E(1-4,6),andeight previously described Daphniphyllum alkaloids(5,7-13)were isolated from Daphniphyllum calycinum.Compound 1 is the first Daphniphyllum alkaloid possessing a highly rearranged 6/6/6/7/5/6 hexacyclic architecture with a unique 3-methyl-1-azabicyclo[4,4,0]decane ring system.Compound 2 represents a rare diamino Daphniphyllum alkaloid with an unprecedented 6/5/5/6/6/5 carbon skeleton featuring a unique 1-aza-6-azaspiro[4,5]decane unit,whereas 3 also represents a rare diamino Daphniphyllum alkaloid as a possible precursor of 2.Compound 4 is the second example of c-22-nor yuzurimine-type alkaloids.Their structures and absolute configurations were elucidated by HRESIMS,NMR spectroscopic analyses,EcD calculations,and single-crystal X-ray diffraction.Moreover,compound 1 showed remarkable antitumor activities,which could inhibit the proliferation,migration and invasion of nasopharyngeal carcinoma cells,and promoted nasopharyngeal carcinoma cells apoptosis.展开更多
One of the largest subfamilies within the famous Daphniphyllum alkaloid family is made up of the yuzurimine-type(or macrodaphniphyllamine-type) alkaloids. Their complex aza-polycyclic caged structures, several contigu...One of the largest subfamilies within the famous Daphniphyllum alkaloid family is made up of the yuzurimine-type(or macrodaphniphyllamine-type) alkaloids. Their complex aza-polycyclic caged structures, several contiguous stereogenic centers, and vicinal all-carbon quaternary centers make these alkaloids formidable challenge for synthetic chemists. Recently, synthesis of these alkaloids has received extensive attention from our community. Herein, we wish to report the total synthesis of C_(14)–epideoxycalyciphylline H, a putative member of yuzurimine-type alkaloid subfamily. Key transformations employed in our approach include an intramolecular Prins reaction and a Pd-catalyzed enyne cycloisomerization. In addition, synthesis of a daphnezomine L-type alkaloid, paxdaphnidine A, was also studied.展开更多
Efficient synthetic routs for the direct and rapid construction of[5-6-6]ABC tricyclic systems of daphmanidin A-type and calyciphylline A-type alkaloids have been successfully developed.For the daphmanidin A-type,the ...Efficient synthetic routs for the direct and rapid construction of[5-6-6]ABC tricyclic systems of daphmanidin A-type and calyciphylline A-type alkaloids have been successfully developed.For the daphmanidin A-type,the synthesis of[5-6-6]tricyclic framework utilize a HCl-mediated intramolecular Aldol reaction to construct the bicyclo[2.2.2]octane core and a thermal condensation to afford the ABC ring system.In addition,for the calyciphylline A-type,an improved synthesis of ABC[5-6-6]tricyclic system was developed,featuring an introduction of methyl ester group at C2 before the Pd-catalyzed intramolecular oxidative alkylation to construct the desired bowl-shape tricyclic core with stereochemical control.展开更多
文摘A new flavan-3-ol glucoside, (-)-afzelechin-7-O-β-D-glucopyranoside (1), has been isolated from the stem of Daphniphyllum oldhami. The structure of the new compound was elucidated on the basis of detailed spectroscopie analysis and comparison with related compounds.
文摘Further phytochemical investigation of the ethyl acetate extract of the stem of Daphniphyllum oldhamii afforded a new phenolic glucoside, named oldhamioside 1, together with eleven known compounds, koaburaside 2, betulin, 28-hydroxyl-3-lupenone, pineresinol, syringaresinol, 4-O-methyl- cedrusin, narigenin, eriodictyol, apigenin, loureirin C, and asperuloside. The structures of new and known compounds were characterized by detailed spectroscopic analysis and comparison of their spectral data with reported values.
基金supportd by the National Natural Science foundation for Outstanding Youth(30125044)partly funded by the"foundation for scholars come back from abroad"provided by Ministry of Education,Ministry of Personnel,and Chinese academy of Sciences.
文摘Two new triterpene esters, 2-O-caffeoylalphitolic acid (1) and methyl 2-O-caffeoyl- alphitolate (2), together with two known triterpenes were isolated from the shrub Daphniphyllum oldhami. The structures of new compounds were elucidated on the basis of detailed spectroscopic analysis and compared with related compound.
基金This work was financially supported by the National Natural Science Foundation of China(30830114)the National Basic Research Program of China(973 Program,2009CB522303)The Syngenta postgraduate studentship awarded to Mingming Cao(2012-2015)is appreciated.
文摘Two new daphnicyclidin-type Daphniphyllum alkaloids,daphmacrodins A and B(1 and 2)were isolated from the leaves and stems of Daphniphyllum macropodum.Their structures were elucidated by extensive spectroscopic techniques,including 2D NMR spectroscopy and mass spectrometry.The relative configuration of 1 was further confirmed by a single-crystal X-ray diffraction analysis.Their cytotoxic activities against five human cancer cell lines,pesticidal activities against brine shrimp(Artemia salina),and antibacterial activities against five standard bacterial and fungal strains were evaluated.The structure of 1 was successfully transformed to 2 by a chemical method.
基金the National Natural Science Foundation of China(No.31770392 to YTD)the Science and Technology Program of Yunnan Province(2018ZF013 to YTD)The authors are grateful to the analytical group of the Laboratory of Phytochemistry,Kunming Institute of Botany,Chinese Academy of Sciences,for recorded spectra.
文摘One new Daphniphyllum alkaloid,daphnioldhanol A(1),together with three known ones,were isolated from the stem part of Daphniphyllum angustifolium Hutch.Their structures were elucidated by spectroscopic methods and comparing with the literature data.Compound 2 is a new natural product,but known by synthesis as a racemate.Compound 1 exhibited week cytotoxic activity against Hela cell line with IC50 of 31.9μM.
基金supported by grants from the National Natural Science Foundation of China(Nos.82173695,82273803,82003743,81973190)the Guangdong Basic and Applied Basic Research Foundation(No.2020B1515020033)Scienceand Technology Planning Projectof Guangzhou City(No.202201010485).
文摘Fivenovel Daphniphyllum alkaloids,named dcalycinumines A-E(1-4,6),andeight previously described Daphniphyllum alkaloids(5,7-13)were isolated from Daphniphyllum calycinum.Compound 1 is the first Daphniphyllum alkaloid possessing a highly rearranged 6/6/6/7/5/6 hexacyclic architecture with a unique 3-methyl-1-azabicyclo[4,4,0]decane ring system.Compound 2 represents a rare diamino Daphniphyllum alkaloid with an unprecedented 6/5/5/6/6/5 carbon skeleton featuring a unique 1-aza-6-azaspiro[4,5]decane unit,whereas 3 also represents a rare diamino Daphniphyllum alkaloid as a possible precursor of 2.Compound 4 is the second example of c-22-nor yuzurimine-type alkaloids.Their structures and absolute configurations were elucidated by HRESIMS,NMR spectroscopic analyses,EcD calculations,and single-crystal X-ray diffraction.Moreover,compound 1 showed remarkable antitumor activities,which could inhibit the proliferation,migration and invasion of nasopharyngeal carcinoma cells,and promoted nasopharyngeal carcinoma cells apoptosis.
基金the National Natural Science Foundation of China (Nos.21971104 and 22271136)Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis (No.ZDSYS20190902093215877)+4 种基金Guangdong Provincial Key Laboratory of Catalysis (No.2020B121201002)Guangdong Innovative Program (No.2019BT02Y335)Education Department of Guangdong Province, Key research projects in colleges and universities in Guangdong Province (No.2021ZDZX2035)Shenzhen Nobel Prize Scientists Laboratory Project (No.C17783101)Innovative Team of Universities in Guangdong Province (No.2020KCXTD016)。
文摘One of the largest subfamilies within the famous Daphniphyllum alkaloid family is made up of the yuzurimine-type(or macrodaphniphyllamine-type) alkaloids. Their complex aza-polycyclic caged structures, several contiguous stereogenic centers, and vicinal all-carbon quaternary centers make these alkaloids formidable challenge for synthetic chemists. Recently, synthesis of these alkaloids has received extensive attention from our community. Herein, we wish to report the total synthesis of C_(14)–epideoxycalyciphylline H, a putative member of yuzurimine-type alkaloid subfamily. Key transformations employed in our approach include an intramolecular Prins reaction and a Pd-catalyzed enyne cycloisomerization. In addition, synthesis of a daphnezomine L-type alkaloid, paxdaphnidine A, was also studied.
基金supported by the National Natural Science Foundation of China(No.21502011)the Fundamental Research Funds for the Central Universitiesthe Chongqing Science&Technology Commission Project(No.cstc2016jcyjA0168)。
文摘Efficient synthetic routs for the direct and rapid construction of[5-6-6]ABC tricyclic systems of daphmanidin A-type and calyciphylline A-type alkaloids have been successfully developed.For the daphmanidin A-type,the synthesis of[5-6-6]tricyclic framework utilize a HCl-mediated intramolecular Aldol reaction to construct the bicyclo[2.2.2]octane core and a thermal condensation to afford the ABC ring system.In addition,for the calyciphylline A-type,an improved synthesis of ABC[5-6-6]tricyclic system was developed,featuring an introduction of methyl ester group at C2 before the Pd-catalyzed intramolecular oxidative alkylation to construct the desired bowl-shape tricyclic core with stereochemical control.
