One new monoterpenoid indole alkaloid, l l-methoxyburnamine-17-O-3′,4′,5′-trimethoxybenzoate （1）, was isolated from Rauvolfia yunnanensis Tsiang. Its structure was identified by speclroscopic evidences.
Four new monoterpenoid indole alkaloids,alstrostines C-F together with thirteen known alkaloids were isolated from the leaves and twigs of Alstonia rostrata.All structures of new compounds were elucidated based on NMR...Four new monoterpenoid indole alkaloids,alstrostines C-F together with thirteen known alkaloids were isolated from the leaves and twigs of Alstonia rostrata.All structures of new compounds were elucidated based on NMR,FTIR,UV,and MS spectroscopic data.Alstrostines C-E might originate from keto-enol tautomerism of preakummicine during biogenetic pathway of akummicine.展开更多
Five new hybrid monoterpenoid indole alkaloids bearing an unusual 2,2-dimethyl-4-oxopiperidin-6-yl moiety,namely rauvotetraphyllines F–H(1,3,4),17-epi-rauvotetraphylline F(2)and 21-epi-rauvotetraphylline H(5),were is...Five new hybrid monoterpenoid indole alkaloids bearing an unusual 2,2-dimethyl-4-oxopiperidin-6-yl moiety,namely rauvotetraphyllines F–H(1,3,4),17-epi-rauvotetraphylline F(2)and 21-epi-rauvotetraphylline H(5),were isolated from the aerial parts of Rauvolfia tetraphylla.Their structures were established by extensive spectroscopic analysis.The new alkaloids were evaluated for their cytotoxicity in vitro against five human cancer cell lines.展开更多
Main observation and conclusion Two new pairs of monoterpenoid indole alkaloids(MIAs)enantiomers as well as their new congeners were isolated from stems of Tabernaemontana bovina Lour.(Apocynaceae).Their structures we...Main observation and conclusion Two new pairs of monoterpenoid indole alkaloids(MIAs)enantiomers as well as their new congeners were isolated from stems of Tabernaemontana bovina Lour.(Apocynaceae).Their structures were elucidated by spectroscopic analyses and confirmed by X-ray diffractions and computational calculations.Tabovine A,tabovine B and tabovines C-D possessed unprecedented 6/5/5/6/6,6/5/5/6/5 and 6/5/6/6/6 ring systems,respectively.It is the first time to report co-occurring enantiomers of MIAs.Additionally,the explanation concerning biogenesis of MIAs was provided.The findings would open a new window where we could disclose more diverse MIAs.展开更多
Phytochemical investigations on Tabernaemontana divaricata led to the isolation of seven undescribed monoterpenoid indole alkaloids,taberdicatines A-G(1-7).Taberdicatines A-C might be derived from Aspidosperma-type al...Phytochemical investigations on Tabernaemontana divaricata led to the isolation of seven undescribed monoterpenoid indole alkaloids,taberdicatines A-G(1-7).Taberdicatines A-C might be derived from Aspidosperma-type alkaloid,less skeletal carbons in 1-2 and an additional carbon in 3.Taberdicatines D-E(4-5)were attributed to Iboga alkaloids with enantiomeric skeleton,respectively.Alkaloid 3 could promote the neurite growth of mouse primary cortical neurons at the concentration of 5 pimol/L.展开更多
Four new monoterpenoid indole alkaloids,bousmekines A-D(1-4),and one new pyranopyridine alkaloid,bousmekine E(5),were isolated from the twigs and leaves of Bousigonia angustifolia and Bousigonia mekongensis.Their stru...Four new monoterpenoid indole alkaloids,bousmekines A-D(1-4),and one new pyranopyridine alkaloid,bousmekine E(5),were isolated from the twigs and leaves of Bousigonia angustifolia and Bousigonia mekongensis.Their structures including absolute configurations were elucidated by a combination of MS,NMR,ECD calculation,and single-crystal X-ray diffraction analysis.Compound 2 was an eburnea-type MIAs characterized by a rare chlorine atom while 5 possessed a novel pyranopyridine moiety.Their cytotoxicities against several human cancer cell lines were evaluated and compound 1 exhibited significant cytotoxicity with IC50 values of 0.8-7.4μM.展开更多
Metabolomics has been rapidly developed as an important field in plant sciences and natural products chemistry.As the only natural source for a diversity of monoterpenoid indole alkaloids(MIAs),especially the low-abun...Metabolomics has been rapidly developed as an important field in plant sciences and natural products chemistry.As the only natural source for a diversity of monoterpenoid indole alkaloids(MIAs),especially the low-abundance antitumor agents vinblastine and vincristine,Catharanthus roseus is highly valued and has been studied extensively as a model for medicinal plants improvement.Due to multistep enzymatic biosynthesis and complex regulation,genetic modification in the MIA pathway has resulted in complicated changes of both secondary and primary metabolism in C.roseus,affecting not only the MIA pathway but also other pathways.Research at the metabolic level is necessary to increase knowledge on the genetic regulation of the whole metabolic network connected to MIA biosynthesis.Nuclear magnetic resonance(NMR)is a very suitable and powerful complementary technique for the identification and quantification of metabolites in the plant matrix.NMR-based metabolomics has been used in studies of C.roseus for pathway elucidation,understanding stress responses,classification among different cultivars,safety and quality controls of transgenic plants,cross talk between pathways,and diversion of carbon fluxes,with the aim of fully unravelling MIA biosynthesis,its regulation and the function of the alkaloids in the plant from a systems biology point of view.展开更多
基金supported by the Knowledge Innovation Program of the CAS(No.KSCX2-YW-G-038, KSCX2-YW-G-027,29KZCX2-XB2-15-03),NSFC(No.30772636)NSFY(No.2005C0010Z)High-Tech Special Project of Yunnan Province(2007),and Foundation of Key State Lab.of Phytochemistry and Plant Resources in West China
文摘One new monoterpenoid indole alkaloid, l l-methoxyburnamine-17-O-3′,4′,5′-trimethoxybenzoate （1）, was isolated from Rauvolfia yunnanensis Tsiang. Its structure was identified by speclroscopic evidences.
基金supported by the National Natural Science Foundation of China(21172225,31170334)the 973 Program of Ministry of Science and Technology of China(2009CB522300)the XiBuZhiGuang Project of Chinese Academy of Sciences,and the Young Academic and Technical Leader Raising Foundation of Yunnan Province(No.2010CI049).
文摘Four new monoterpenoid indole alkaloids,alstrostines C-F together with thirteen known alkaloids were isolated from the leaves and twigs of Alstonia rostrata.All structures of new compounds were elucidated based on NMR,FTIR,UV,and MS spectroscopic data.Alstrostines C-E might originate from keto-enol tautomerism of preakummicine during biogenetic pathway of akummicine.
基金This work was financially supported by “Largescale Compound Library” Project of National Development and Reform Commission of China.
文摘Five new hybrid monoterpenoid indole alkaloids bearing an unusual 2,2-dimethyl-4-oxopiperidin-6-yl moiety,namely rauvotetraphyllines F–H(1,3,4),17-epi-rauvotetraphylline F(2)and 21-epi-rauvotetraphylline H(5),were isolated from the aerial parts of Rauvolfia tetraphylla.Their structures were established by extensive spectroscopic analysis.The new alkaloids were evaluated for their cytotoxicity in vitro against five human cancer cell lines.
基金This work was supported by the National Natural Science Foundation of China(Nos.31872677,31370377)Computational resources used in this work were supported in part by SciGrid,Chinese Academy of Sciences.
文摘Main observation and conclusion Two new pairs of monoterpenoid indole alkaloids(MIAs)enantiomers as well as their new congeners were isolated from stems of Tabernaemontana bovina Lour.(Apocynaceae).Their structures were elucidated by spectroscopic analyses and confirmed by X-ray diffractions and computational calculations.Tabovine A,tabovine B and tabovines C-D possessed unprecedented 6/5/5/6/6,6/5/5/6/5 and 6/5/6/6/6 ring systems,respectively.It is the first time to report co-occurring enantiomers of MIAs.Additionally,the explanation concerning biogenesis of MIAs was provided.The findings would open a new window where we could disclose more diverse MIAs.
基金the National Natural Science Foundation of China(Nos.31872677,31370377).Computational resources used in this work were supported in part by SciGrid,Chinese Academy of Sciences.
文摘Phytochemical investigations on Tabernaemontana divaricata led to the isolation of seven undescribed monoterpenoid indole alkaloids,taberdicatines A-G(1-7).Taberdicatines A-C might be derived from Aspidosperma-type alkaloid,less skeletal carbons in 1-2 and an additional carbon in 3.Taberdicatines D-E(4-5)were attributed to Iboga alkaloids with enantiomeric skeleton,respectively.Alkaloid 3 could promote the neurite growth of mouse primary cortical neurons at the concentration of 5 pimol/L.
基金This work was financially supported by Yunnan Applied Basic Research Projects(2018FA049)Top Young Talent of the Ten Thousand Talents Program of Yunnan(to Y.Zhang).
文摘Four new monoterpenoid indole alkaloids,bousmekines A-D(1-4),and one new pyranopyridine alkaloid,bousmekine E(5),were isolated from the twigs and leaves of Bousigonia angustifolia and Bousigonia mekongensis.Their structures including absolute configurations were elucidated by a combination of MS,NMR,ECD calculation,and single-crystal X-ray diffraction analysis.Compound 2 was an eburnea-type MIAs characterized by a rare chlorine atom while 5 possessed a novel pyranopyridine moiety.Their cytotoxicities against several human cancer cell lines were evaluated and compound 1 exhibited significant cytotoxicity with IC50 values of 0.8-7.4μM.
基金National High-tech R&D Program of China(2011AA100605)Shanghai Key Discipline Cultivation and Construction Project(Horticulture)Shanghai Jiao Tong University Agri-Engineering Program.
文摘Metabolomics has been rapidly developed as an important field in plant sciences and natural products chemistry.As the only natural source for a diversity of monoterpenoid indole alkaloids(MIAs),especially the low-abundance antitumor agents vinblastine and vincristine,Catharanthus roseus is highly valued and has been studied extensively as a model for medicinal plants improvement.Due to multistep enzymatic biosynthesis and complex regulation,genetic modification in the MIA pathway has resulted in complicated changes of both secondary and primary metabolism in C.roseus,affecting not only the MIA pathway but also other pathways.Research at the metabolic level is necessary to increase knowledge on the genetic regulation of the whole metabolic network connected to MIA biosynthesis.Nuclear magnetic resonance(NMR)is a very suitable and powerful complementary technique for the identification and quantification of metabolites in the plant matrix.NMR-based metabolomics has been used in studies of C.roseus for pathway elucidation,understanding stress responses,classification among different cultivars,safety and quality controls of transgenic plants,cross talk between pathways,and diversion of carbon fluxes,with the aim of fully unravelling MIA biosynthesis,its regulation and the function of the alkaloids in the plant from a systems biology point of view.
