Chemical Constituents And Biological Activities Of Caulophyllum Robustum Maxim

Caulophyllum robustum Maxim,a perennial herb in the family Berberidaceae,is widely distributed in Heilongjiang,Shanxi,Hubei and other places.In folk,its roots and rhizomes are used to treat rheumatic pain,bruises,menstruate disorder,postpartum stasis and pain,arthritis,hypertension,injuries and so on.In order to provide a scientific basis for the further development and application of C.robustum,we have investigated the chemical constituents and biological activities of this plant.In this thesis,the ethyl acetate and n-butanol extracts of C.robustum wer e isolated by silica gel column chromatography,Sephadex LH-20 column chro matography and reversed-phase high performance liquid chromatography,which led to the isolation of 12 compounds.And their structures were elucidated by spectroscopic data analysis as 3-oxo-21β,23-dihydroxyolean-12-en-28-oic acid(1),3β,23-dihydroxy-28-norolean-12-ene-16-one(2),hederagenin-3-O-?-L-arabin opyranosyl(3),collinsonidin(4),3?-[(?-L-arabinopyranosyl)-oxy]-16?-hydroxy-23-oxo-olean-12-en-28-oic acid(5),boldine(6),taspine(7),cytisine(8),2,4-d ihydroxybenzaldehyde(9),fisetol(10),hodgsonialloside C(11)and(-)-isolar iciresinol 3α-O-β-D-glucopyranoside(12).And among them,compounds 1 and 2 were new compounds,and compounds 9-12 were isolated from C.robustu m for the first time.Anti-inflammatory and anti-diabetic active constituents were screened from the constructed C.robustum chemical composition database using SYBYL molecular docking technology,and the interaction forces between compounds and protein targets were analyzed using Discovery Studio 2017 R2 Client and Py MOL software.The results showed that some of the compounds from C.robustum had good binding ability to the anti-inflammatory and anti-diabetic targets.Furthermore,compounds mainly generated hydrogen bond and hydrophobic interaction with targets,such as IKKβ,P38 α and α-glucosidase.Based on the results of virtual screening,the chemical constituents of C.r obustum with higher scores were selected for IKKβ,p38α MAPK,and α-glucosidase enzyme assay in vitro.The results showed boldine,taspine and magnola mide had moderate IKKβ inhibitory activity;3β-[(α-L-arabinopyranosyl)-oxy]-16α-hydroxy-23-oxo-olean-12-en-28-oic acid and magnolamide showed moderate p38α MAPK inhibitory activity;3-oxo-21β,23-dihydroxyolean-12-en-28-oic acid,3β,23-dihydroxy-28-norolean-12-ene-16-one,3β-[(α-L-arabinopyranosyl)-oxy]-16α-hydroxy-23-oxo-olean-12-en-28-oic acid,23-hydroxy-3,19-dioxo-olean-12-en-28-o ic-acid and Eechinocystic acid 3-O-α-L-arabinopyranoside had good α-glucosidas e inhibitory activity.In summary,the research on the chemical constituents and biological activity of C.robustum has accumulated new data for the development and utilization of this plant.Some of the triterpenoids in C.robustum have good anti-diabetic activity and provide a reference for the subsequent development of drugs for the prevention and treatment of diabetes.