Two new norditerpenoid alkaloids, spicatine A (1) and spicatine B (2) were isolated from the root of Aconitum spicatum. The new compounds were deduced on the basis of their spectral data (IR, HREIMS, EIMS, 1D, 2D-NM...Two new norditerpenoid alkaloids, spicatine A (1) and spicatine B (2) were isolated from the root of Aconitum spicatum. The new compounds were deduced on the basis of their spectral data (IR, HREIMS, EIMS, 1D, 2D-NMR). This is the first whole report on the isolation of diterpenoid alkaloids from the A.spicatum Stapf.展开更多
Two new norditerpenoid alkaloids were isolated from the roots of Aconitum nagarum.Their structures were elucidated as 13-hydroxyfranchetine 1 and 10-dehydroxyflavaconitine 2,respectively, by 1D and 2D NMR experiments.
Further phytochemical investigation of the unique C 18-norditerpenoid alkaloids from the roots ofAconitum delavayi Franch led to the isolation of two new norditerpenoid alkaloids, delavaconitine F 1 and delavaconitine...Further phytochemical investigation of the unique C 18-norditerpenoid alkaloids from the roots ofAconitum delavayi Franch led to the isolation of two new norditerpenoid alkaloids, delavaconitine F 1 and delavaconitine G 2. Their structures were determined from spectroscopic evidence.展开更多
Electrospray ionization mass spectrometry（ESI-MS） was applied simultaneously in determining norditerpenoid alkaloids from the roots of Aconitum sinomantanum Nakai （RAS） based on molecular mass information. The tan...Electrospray ionization mass spectrometry（ESI-MS） was applied simultaneously in determining norditerpenoid alkaloids from the roots of Aconitum sinomantanum Nakai （RAS） based on molecular mass information. The tandem mass spectra（ ESI-MS^n） provided the alkaloidal structural information, through which the existence of these alkaloids was further confirmed. Accordingly, six known norditerpenoid alkaloids were simultaneously determined on the basis of their ESI-MS^n spectra. Furthermore, based on the diagnostic fragmentation pathways of alkaloidal MS^n, a rapid method for direct detection and characterization of alkaloids from an ethanolic extract of RAS was described.展开更多
To search for pharmacologically and structurally interesting substances from traditional Chinese medicines, we Investigated the chemical compounds of Aconitum spicatum Stapf. Two new nordlterpenold alkaloids, namely s...To search for pharmacologically and structurally interesting substances from traditional Chinese medicines, we Investigated the chemical compounds of Aconitum spicatum Stapf. Two new nordlterpenold alkaloids, namely spicatlne A （compound 1） and splcatine B （compound 2）, as well as 11 known norditerpenoid alkaloids were Isolated from the CHCIs portion of the 90% ethanol extract of the roots of A. spicatum. The structures of the alkaloids were characterized on the basis of their spectral data. One of the Isolated compounds showed significant cytotoxic activities （IC50 values 〈 200μmol/l.） against the HL-60 cell line.展开更多
Four new norditerpenoid heterodimers with different dimerization patterns-namely,trigofragiloids A-C(denoted as compounds 1-3)and(+)-and(-)-trigofragiloid D(compound 4)-and three new phenanthrenone norditerpenoids-nam...Four new norditerpenoid heterodimers with different dimerization patterns-namely,trigofragiloids A-C(denoted as compounds 1-3)and(+)-and(-)-trigofragiloid D(compound 4)-and three new phenanthrenone norditerpenoids-namely,trigofragiloids E-G(compounds 5-7)-were isolated from Trigonostemon fragilis.Compounds 1 and 2 feature a novel heterodimeric carbon skeleton formed by the conjugation of a tetra-norditerpenoid and an ennea-norditerpenoid;they have been identified as class 2 atropisomers by means of quantum chemical calculations.Compound 3 is an unprecedented phenylpropanoid-norditerpenoid adduct with a new dimerization pattern.Compounds(+)-and(-)-4 are the first example of S-shaped 1,4-dioxane-fused norditerpenoid dimers.Inspired by the structure elucidation of compound 4,two co-occurring analogues,actephilol A and epiactephilol A,were structurally revised as a pair of geometrical isomers and were identified as two pairs of enantiomers,(+)-and(-)-8 and(+)-and(-)-9,respectively.Their structures were characterized using a combined method.Notably,compound 7 exhibits remarkable adenosine triphosphate-citrate lyase(ACLY)inhibition with a halfmaximal inhibition concentration(IC50)value of(0.46±0.11)lmol·L^(-1),as active as the positive control BMS-303141,and a molecular docking study offers deep insight into the interaction between compound 7 and ACLY.展开更多
Oxidation of 1 with KMnO_4 in acetone-H_2O (1:1) for 1h gave nevadenine 2 (38%). But. 3 was formed in 98% yield when prolonging time and raising temperature (40℃). Reaction of 1 and 10 with Conforth reagent afforded ...Oxidation of 1 with KMnO_4 in acetone-H_2O (1:1) for 1h gave nevadenine 2 (38%). But. 3 was formed in 98% yield when prolonging time and raising temperature (40℃). Reaction of 1 and 10 with Conforth reagent afforded the ketones 11 (55%), 12 (30%), and 13 (13%), 14 (20%). respectively. While oxidation of 7 and 15 with a variety of the oxidizing agents gave 17 only in low 20% of yield besides the minor 16. In addition. 1 was converted to 2 by the fungi Curvularia lunata.展开更多
The synthesis of a new N,19-seco norditerpenoid alkaloid 7 bearing nitro group from yunaconitine 1 as the starting material through a series of steps was described.
Treatment of 3-acetylpseudaconie 6 and 3. 13-diacetylyunnaconitine 9 withNBS/acetone-H2O(2:1) at room temperature produced corresponding imine derivatives & and 10.respectively. in good yields. This is a novel si...Treatment of 3-acetylpseudaconie 6 and 3. 13-diacetylyunnaconitine 9 withNBS/acetone-H2O(2:1) at room temperature produced corresponding imine derivatives & and 10.respectively. in good yields. This is a novel simple and convenient method for preparation of theimine compounds.展开更多
Two new norditerpenoid alkaloids, souline A and souline B, were isolated from Delphinium souliei Franch, and their structures were elucidated by spectroscopic methods.
Treatment of lappaconitine 1 with HIO4 at room temperature afforded 2 in 41% yield, to which Br2-HOAc solution was added and allowed to stand at room temperature for 2 days to give 3 (13%) and 4(31%).
Two new norditerpenoid alkaloids, orthocentrine (1) and deacetylswinanine A (2), together with a known alkaloid, swinanine A (3), were isolated from the whole plants of Delphinium orthocentrum Franch. The structures o...Two new norditerpenoid alkaloids, orthocentrine (1) and deacetylswinanine A (2), together with a known alkaloid, swinanine A (3), were isolated from the whole plants of Delphinium orthocentrum Franch. The structures of the new alkaloids (1 and 2) were elucidated as 7,10_dihydroxy_8,14,16_trimethoxy_19,20_didehydro_aconitane (7β,8β,14α,16β) (1) and 20_ethyl_2,3_didehydro_6,10_dihydroxy_7,8_methylenedioxy_1,14,16_trimethoxy_aconitane (1α,6β,14α,16β) (2) by spectroscopic evidence and chemical transformation.展开更多
文摘Two new norditerpenoid alkaloids, spicatine A (1) and spicatine B (2) were isolated from the root of Aconitum spicatum. The new compounds were deduced on the basis of their spectral data (IR, HREIMS, EIMS, 1D, 2D-NMR). This is the first whole report on the isolation of diterpenoid alkaloids from the A.spicatum Stapf.
文摘Two new norditerpenoid alkaloids were isolated from the roots of Aconitum nagarum.Their structures were elucidated as 13-hydroxyfranchetine 1 and 10-dehydroxyflavaconitine 2,respectively, by 1D and 2D NMR experiments.
基金the National Natural Science Foundation of China （No. 90409015）.
文摘Further phytochemical investigation of the unique C 18-norditerpenoid alkaloids from the roots ofAconitum delavayi Franch led to the isolation of two new norditerpenoid alkaloids, delavaconitine F 1 and delavaconitine G 2. Their structures were determined from spectroscopic evidence.
文摘Electrospray ionization mass spectrometry（ESI-MS） was applied simultaneously in determining norditerpenoid alkaloids from the roots of Aconitum sinomantanum Nakai （RAS） based on molecular mass information. The tandem mass spectra（ ESI-MS^n） provided the alkaloidal structural information, through which the existence of these alkaloids was further confirmed. Accordingly, six known norditerpenoid alkaloids were simultaneously determined on the basis of their ESI-MS^n spectra. Furthermore, based on the diagnostic fragmentation pathways of alkaloidal MS^n, a rapid method for direct detection and characterization of alkaloids from an ethanolic extract of RAS was described.
文摘To search for pharmacologically and structurally interesting substances from traditional Chinese medicines, we Investigated the chemical compounds of Aconitum spicatum Stapf. Two new nordlterpenold alkaloids, namely spicatlne A （compound 1） and splcatine B （compound 2）, as well as 11 known norditerpenoid alkaloids were Isolated from the CHCIs portion of the 90% ethanol extract of the roots of A. spicatum. The structures of the alkaloids were characterized on the basis of their spectral data. One of the Isolated compounds showed significant cytotoxic activities （IC50 values 〈 200μmol/l.） against the HL-60 cell line.
基金support from the National Natural Science Foundation of China(22237007 and 22177122)the Biological Resources Program of Chinese Academy of Sciences(CAS)(KFJ-BRP-008-001)the Youth Innovation Promotion Association of Chinese Academy of Sciences(2022282)is gratefully acknowledged.We thank Prof.Shi-Man Huang,Department of Biology,Hainan University,China,for the identification of the plant material.
文摘Four new norditerpenoid heterodimers with different dimerization patterns-namely,trigofragiloids A-C(denoted as compounds 1-3)and(+)-and(-)-trigofragiloid D(compound 4)-and three new phenanthrenone norditerpenoids-namely,trigofragiloids E-G(compounds 5-7)-were isolated from Trigonostemon fragilis.Compounds 1 and 2 feature a novel heterodimeric carbon skeleton formed by the conjugation of a tetra-norditerpenoid and an ennea-norditerpenoid;they have been identified as class 2 atropisomers by means of quantum chemical calculations.Compound 3 is an unprecedented phenylpropanoid-norditerpenoid adduct with a new dimerization pattern.Compounds(+)-and(-)-4 are the first example of S-shaped 1,4-dioxane-fused norditerpenoid dimers.Inspired by the structure elucidation of compound 4,two co-occurring analogues,actephilol A and epiactephilol A,were structurally revised as a pair of geometrical isomers and were identified as two pairs of enantiomers,(+)-and(-)-8 and(+)-and(-)-9,respectively.Their structures were characterized using a combined method.Notably,compound 7 exhibits remarkable adenosine triphosphate-citrate lyase(ACLY)inhibition with a halfmaximal inhibition concentration(IC50)value of(0.46±0.11)lmol·L^(-1),as active as the positive control BMS-303141,and a molecular docking study offers deep insight into the interaction between compound 7 and ACLY.
基金We thank the National Natural Science Foundation of China !(No. 393707) the Chengdu Diao Pharmaceutical Company for support
文摘Oxidation of 1 with KMnO_4 in acetone-H_2O (1:1) for 1h gave nevadenine 2 (38%). But. 3 was formed in 98% yield when prolonging time and raising temperature (40℃). Reaction of 1 and 10 with Conforth reagent afforded the ketones 11 (55%), 12 (30%), and 13 (13%), 14 (20%). respectively. While oxidation of 7 and 15 with a variety of the oxidizing agents gave 17 only in low 20% of yield besides the minor 16. In addition. 1 was converted to 2 by the fungi Curvularia lunata.
基金Financial support for this research was provided by the National Natural Science Foundation of China (No. 3007088). We are grateful to Professor Xiao-Tian Liang for his advice on this manuscript.
文摘The synthesis of a new N,19-seco norditerpenoid alkaloid 7 bearing nitro group from yunaconitine 1 as the starting material through a series of steps was described.
文摘Treatment of 3-acetylpseudaconie 6 and 3. 13-diacetylyunnaconitine 9 withNBS/acetone-H2O(2:1) at room temperature produced corresponding imine derivatives & and 10.respectively. in good yields. This is a novel simple and convenient method for preparation of theimine compounds.
文摘Two new norditerpenoid alkaloids, souline A and souline B, were isolated from Delphinium souliei Franch, and their structures were elucidated by spectroscopic methods.
文摘Treatment of lappaconitine 1 with HIO4 at room temperature afforded 2 in 41% yield, to which Br2-HOAc solution was added and allowed to stand at room temperature for 2 days to give 3 (13%) and 4(31%).
文摘Two new norditerpenoid alkaloids, orthocentrine (1) and deacetylswinanine A (2), together with a known alkaloid, swinanine A (3), were isolated from the whole plants of Delphinium orthocentrum Franch. The structures of the new alkaloids (1 and 2) were elucidated as 7,10_dihydroxy_8,14,16_trimethoxy_19,20_didehydro_aconitane (7β,8β,14α,16β) (1) and 20_ethyl_2,3_didehydro_6,10_dihydroxy_7,8_methylenedioxy_1,14,16_trimethoxy_aconitane (1α,6β,14α,16β) (2) by spectroscopic evidence and chemical transformation.
