Studies On Chemical Components From Delphinium Umbrosum Hand.-Mazz.and Their Biological Activities

Delphinium umbrosum Hand.-Mazz.belongs to the Ranunculaceae family and is collected from Shangri-La,Diqing Prefecture,Yunnan Province.At present,there is no relevant research report of D.umbrosum.In order to search for new compounds with novel structure and biological activity,the chemical constituents and biological activities of D.umbrosum were studied in this thesis.In this paper,total alkaloids were prepared by cold leaching,acid extraction and alkali precipitation,extraction and concentration under reduced pressure from D.umbrosum.Total alkaloids were separated and purified by silica gel column chromatography.Their structures were elucidated on the basis of extensive spectroscopic analysis,including HR-ESI-MS,IR,1D-and 2D-NMR experiments.Twenty-four compounds were isolated,including three new compounds named umbrodine A（1）,umbrodine B（2）and umbrolide A（3）,compound 1 was a vakognavine-type C₂₀-diterpenoid alkaloid,compound 2 was a hetisine-type C₂₀-diterpenoid alkaloid,compound 3 was a dibenzoxazepinone derivative.The twenty-one known compounds were:lycoctonine（4）,anthranoyllycoctonine（5）,majusine A（6）,14-deacetylajadine（7）,ajacine（8）,14-deacetylnudicauline（9）,methyllycaconitine（10）,delsemine A（11）,delsemine B（12）,delavaine A free acid（13）,delavaine B free acid（14）,delavaine A（15）,delavaine B（16）,gyalanine A（17）,gyalanine B（18）,umbrosumine C（19）,umbrosumine A（20）,umbrosumine B（21）,S-glaucine（22）,2-amino（4-methoxy-2-methyl-1,4-dioxobutyl）,benzoic acid（23）and methyl 2-（3-methyl-2,5-dioxopyrrolidin-1-yl）,benzoate（24）,including eighteen lycoctonine-type C₁₉-diterpenoid alkaloids（4-21）,one isoquinoline alkaloid（22）and two benzoic acid compounds（23,24）.All known compounds were isolated from this plant for the first time.The acetylcholinesterase inhibitory activity,anti-inflammatory activity and antitumor activity of parts of compounds were investigated:（1）Using tacrine as a positive control,the inhibitory activity of compounds（1,2,4-22）on acetylcholinesterase was tested,and the results showed that compounds 7,9 and 19 showed weak acetylcholinesterase inhibitory effect,and the inhibition rates were 53.07%,56.47%and 51.09%,respectively;（2）with celecoxib as a positive control,the compounds（1,2,4-22）were tested on the secretion of NO in RAW 264.7 cells induced by lipopolysaccharide.Among them,compound 22 showed weak inhibitory activity with the inhibition rate was 53.95%;（3）Using taxol as a positive control,the antitumor effects of compounds（1,2,4-22）on mouse breast cancer 4T1 cells was investigated.The results of the study showed that all tested compounds had no obvious antitumor activity.