1,2-methylenedioxy-9-methoxy-N-methoxycarbonyl-aporphine and 1,2-methylenedioxy -8,9-dimethoxy-N-methoxycarbonyl-aporphine, two new alkaloids possessing a N-(methoxy carbonyl) group have been isolated from the stems o...1,2-methylenedioxy-9-methoxy-N-methoxycarbonyl-aporphine and 1,2-methylenedioxy -8,9-dimethoxy-N-methoxycarbonyl-aporphine, two new alkaloids possessing a N-(methoxy carbonyl) group have been isolated from the stems of Fssistigma bracteolatum. Their structures were established on the basis of spectral analysis.展开更多
Artabotrine 1 is a novel N-methoxylated 4,5-dioxoaporphine alkaloid which has been reported to be cytotoxic against P-388 cells. The total synthesis of 1 was carded out, and one of its analogue, N-methoxycepharadione ...Artabotrine 1 is a novel N-methoxylated 4,5-dioxoaporphine alkaloid which has been reported to be cytotoxic against P-388 cells. The total synthesis of 1 was carded out, and one of its analogue, N-methoxycepharadione B 2, was also synthesized. Both of the alkaloids and several intermediates were cytotoxic to several selected tumor cell lines.展开更多
A new aporphine alkaloid, named fuzitine, was isolated from the tuber of Aconitum carmicheali Debx, and its chemical structure was established'on the basis of spectral analysis and chemical reaction.
Aporphine alkaloids have diverse pharmacological activities;however,our understanding of their biosynthesis is relatively limited.Previous studies have classified aporphine alkaloids into two categories based on the c...Aporphine alkaloids have diverse pharmacological activities;however,our understanding of their biosynthesis is relatively limited.Previous studies have classified aporphine alkaloids into two categories based on the configuration and number of substituents of the D-ring and have proposed preliminary biosynthetic pathways for each category.In this study,we identified two specific cytochrome P450 enzymes(CYP80G6 and CYP80Q5)with distinct activities toward(S)-configured and(R)-configured substrates from the herbaceous perennial vine Stephania tetrandra,shedding light on the biosynthetic mechanisms and stereochemical features of these two aporphine alkaloid categories.Additionally,we characterized two CYP719C enzymes(CYP719C3 and CYP719C4)that catalyzed the formation of the methylenedioxy bridge,an essential pharmacophoric group,on the A-and D-rings,respectively,of aporphine alkaloids.Leveraging the functional characterization of these crucial cytochrome P450 enzymes,we reconstructed the biosynthetic pathways for the two types of aporphine alkaloids in budding yeast(Saccharomyces cerevisiae)for the de novo production of compounds such as(R)-glaziovine,(S)-glaziovine,and magnoflorine.This study provides key insight into the biosynthesis of aporphine alkaloids and lays a foundation for producing these valuable compounds through synthetic biology.展开更多
Seven new isoquinoline alkaloids,9-(2’-formyl-5’,6’-dimethoxyphenoxy)-1,2,3,10-tetramethoxy dehydroaporphine(1),9-(2’-formyl-5’,6’-dimethoxyphenoxy)-1,2,3,10-tetramethoxy oxoaporphine(2),3-methoxy-2’-formyl oxo...Seven new isoquinoline alkaloids,9-(2’-formyl-5’,6’-dimethoxyphenoxy)-1,2,3,10-tetramethoxy dehydroaporphine(1),9-(2’-formyl-5’,6’-dimethoxyphenoxy)-1,2,3,10-tetramethoxy oxoaporphine(2),3-methoxy-2’-formyl oxohernandalin(3),(–)-9-(2’-methoxycarbonyl-5’,6’-dimethoxyphenoxy)-1,2,3,10-tetramethoxy aporphine(4),(–)-2’-methoxycarbonyl thaliadin(5),(–)-9-(2’-methoxyethyl-5’,6’-dimethoxyphenoxy)-1,2,3,10-tetramethoxy aporphine(6),(–)-3-methoxy hydroxyhernandalinol(7),together with six known isoquinoline alkaloids(8–13)were isolated from the roots of Thalictrum foetidum.Their structures were elucidated by extensive spectroscopic measurements.Compounds 1 and 2 showed significant selective cytotoxicity against glioma stem cells(GSC-3#and GSC-18#)with IC50 values ranging from 2.36 to 5.37μg·mL^–1.展开更多
文摘1,2-methylenedioxy-9-methoxy-N-methoxycarbonyl-aporphine and 1,2-methylenedioxy -8,9-dimethoxy-N-methoxycarbonyl-aporphine, two new alkaloids possessing a N-(methoxy carbonyl) group have been isolated from the stems of Fssistigma bracteolatum. Their structures were established on the basis of spectral analysis.
文摘Artabotrine 1 is a novel N-methoxylated 4,5-dioxoaporphine alkaloid which has been reported to be cytotoxic against P-388 cells. The total synthesis of 1 was carded out, and one of its analogue, N-methoxycepharadione B 2, was also synthesized. Both of the alkaloids and several intermediates were cytotoxic to several selected tumor cell lines.
文摘A new aporphine alkaloid, named fuzitine, was isolated from the tuber of Aconitum carmicheali Debx, and its chemical structure was established'on the basis of spectral analysis and chemical reaction.
基金supported by the National Key R&D Program of China(2020YFA0908000)the National Natural Science Foundation of China(82011530137,31961133007)+2 种基金Scientific and technological innovation project of CACMS(CI2023D002,CI2023E002)Key project at central government level:The ability to establish sustainable use of valuable Chinese medicine resources(2060302)Vetenskapsradet(2018-06003),Stiftelsen for internationalisering av hogre utbildning och forskning。
文摘Aporphine alkaloids have diverse pharmacological activities;however,our understanding of their biosynthesis is relatively limited.Previous studies have classified aporphine alkaloids into two categories based on the configuration and number of substituents of the D-ring and have proposed preliminary biosynthetic pathways for each category.In this study,we identified two specific cytochrome P450 enzymes(CYP80G6 and CYP80Q5)with distinct activities toward(S)-configured and(R)-configured substrates from the herbaceous perennial vine Stephania tetrandra,shedding light on the biosynthetic mechanisms and stereochemical features of these two aporphine alkaloid categories.Additionally,we characterized two CYP719C enzymes(CYP719C3 and CYP719C4)that catalyzed the formation of the methylenedioxy bridge,an essential pharmacophoric group,on the A-and D-rings,respectively,of aporphine alkaloids.Leveraging the functional characterization of these crucial cytochrome P450 enzymes,we reconstructed the biosynthetic pathways for the two types of aporphine alkaloids in budding yeast(Saccharomyces cerevisiae)for the de novo production of compounds such as(R)-glaziovine,(S)-glaziovine,and magnoflorine.This study provides key insight into the biosynthesis of aporphine alkaloids and lays a foundation for producing these valuable compounds through synthetic biology.
基金supported by the Natural Science Foundation of China(U1802281,31770388)
文摘Seven new isoquinoline alkaloids,9-(2’-formyl-5’,6’-dimethoxyphenoxy)-1,2,3,10-tetramethoxy dehydroaporphine(1),9-(2’-formyl-5’,6’-dimethoxyphenoxy)-1,2,3,10-tetramethoxy oxoaporphine(2),3-methoxy-2’-formyl oxohernandalin(3),(–)-9-(2’-methoxycarbonyl-5’,6’-dimethoxyphenoxy)-1,2,3,10-tetramethoxy aporphine(4),(–)-2’-methoxycarbonyl thaliadin(5),(–)-9-(2’-methoxyethyl-5’,6’-dimethoxyphenoxy)-1,2,3,10-tetramethoxy aporphine(6),(–)-3-methoxy hydroxyhernandalinol(7),together with six known isoquinoline alkaloids(8–13)were isolated from the roots of Thalictrum foetidum.Their structures were elucidated by extensive spectroscopic measurements.Compounds 1 and 2 showed significant selective cytotoxicity against glioma stem cells(GSC-3#and GSC-18#)with IC50 values ranging from 2.36 to 5.37μg·mL^–1.
