Studies On The Chemical Constituents And Their Bioactivities Of Plantago Depressa And The Seeds Of Ipomoea Nil

In this thesis,the chemical constituents and biological activities of two traditional Chinese medicines,Plantago depressa and Ipomoea nil,were systematically studied.Eighty-two monomer compounds were isolated and identified by various separation techniques,spectroscopy and chemical methods,including thirty-five fatty acid derivatives,sixteen phenylethanoid glycosides,sixteen triterpenoids and their glycosides,five phenylpropanoids and their glycosides,three lignans,two steroids,two butenolides,one iridoid,one flavonoid glycoside,and one monoterpenoid glycoside,and eleven new compounds,three new natural products and three new artificial products were found among them.The biological activities of most compounds were also studied.The main research contents include:forty-nine compounds were isolated and identified from Plantago depressa.Thirty-six compounds were separated from ethyl acetate extraction phase:nineteen fatty acid derivatives 1–19,including four pairs of enantiomers 1–8,of which1–6 were new compounds,7 and 8 were new natural products,fourteen triterpenes 20-33including one new arborane triterpene 20,two new butenolides 34 and 35,and one iridoid 36.Thirteen phenylethanol glycosides 37–49 were separated from n-butanol extraction phase,of which 37 was new compound.The known compounds are porrigenic acid?10?,?9Z,12Z,14E?-16-oxo-octadecatrienoic acid?11?,?10Z,12E,14Z?-9,16-dioxo-octadecatrienoic acid?12?,linoleic acid?13?,?-?9?Z,12?Z,15?Z?-octadecatrienoic acid monoglyceride?14?,1-O-?9Z,12Z?-octadecadienoyl glycerol?15?,?-?9?Z,12?Z,15?Z?-octadecatrienoic acid monoglyceride?16?,1-O-?10E,12E?-9-oxo-octadecadienoylglycerol?17?,1-O-?9Z,11E?-13-oxo-octadecadienoyl glycerol?18?and 1-O-?9Z,11E?-9-oxo-octadecadienoyl glycerol?19?,ursolic acid lactone?21?,rubiarbonol A?22?,rubiarbonol B?23?,rubiarbonol L?24?,ursolic acid?25?,pomolic acid?26?,uvaol?27?,corosolic acid?28?,spinosic acid?29?,oleanolic acid?30?,maslinic acid?31?,olean-12-en-2,3-diol?32?,erythrodiol?33?,chlorovaltrate?36?,plantamajoside?38?,plontoinoside D?39?,jionoside C?40?,acteoside?41?,isoacteoside?42?,jionoside D?43?,stachysoside A?44?,plonrainoside C?45?,cis-acteoside?46?,salsaside B?47?,martynoside?48?and suspensaside B?49?.Thirty-three compounds were isolated and identified from the seeds of Ipomoea nil,of which twenty-four compounds were separated from ethyl acetate extraction phase:sixteen fatty acid derivatives 50–65,of which 50–53 were new compounds,five phenylethanol and their glycosides 66–70,two steroids 71–72 and one flavonoid glycoside 73.Ten compounds were separated from n-butanol extraction phase:three lignans 74–76,three phenylethanol glycosides 77–79,two terpenoid saponins 80–81 and one monoterpene glycoside 82.The known compounds are 9-octadecenoicacid-2',3'-dihydroxy propyl ester?54?,?Z?-12-octadecenic-glycerol monoester?55?,glycerol 1-9',12'-octadecadienoate?56?,1-octadecatetraenoylglycerol?57?,2-linoleoylglycerol?58?,13-hydroxy-9Z,11E-octadecadienoic acid?59?,9-oxooctadec-cis-12-enoic acid?60?,linoleic acid?61?,rabdosia acid A?62?,oxylipin?63?,?Z?-9,10,11-trihydroxy-12-octadecenoic acid?64?,?8R,9R,10S,6Z?-trihydroxyoctadec-6-enoic acid?65?,?E?-p-coumaric acid?66?,caffeoyl alcohol?67?,?E?-methyl caffeate?68?,?E?-ethyl caffeate?69?,chlorogenic acid?70?,?-sitosterol?71?,3?,5?-dihydroxy-6?-methoxyergosta-7,22-diene?72?,quercetin3-glucoside?73?,isatioxyneolignoside E?74?,isatioxyneolignoside F?75?,??10??-syringaresinol-4?-O-?-D-glucopyranoside?76?,osmanthuside H?77?,osmanthuside J?78?,pharbiniloside?79?,pharbitoside A?80?,pharbitoside B?81?,jasminoside N?82?.The anti-inflammatory activities of some isolated monomer compounds were studied.Two fatty acid derivatives linoleic acid?13?and 1-O-?9Z,11E?-13-oxo-octadecadienoyl glycerol?18?and a triterpenoid compound olean-12-en-2,3-diol?32?were found to have moderate anti-inflammatory effects on lipopolysaccharide induced NO production and the IC₅₀ were 13.08?0.25,7.64?0.21,5.33?0.51??,respectively.It was found that the phenylethanoid glycosides 37–49 separated from Plantago depressa had better antioxidant activities with IC₅₀ ranged from 2.70 to 51.51?M.The?-glucosidase inhibitory activity of some isolated monomer compounds were studied.It was found that two fatty acid derivatives13-hydroxy-9Z,11E-octadecadienoic acid?59?and rabdosia acid A?62?displayed better?-glucosidase inhibitory activities and the IC₅₀ were 92.73?3.12,11.39?2.18??,respectively.