Study On The Chemical Constituents And Antitumor Activity Of Clerodendrum Japonicum And Lysimachia Fortunei

The study of this paper focused on chemical constituents and biological activities of Clerodendrum japonicum?Thunb.?Sweet and Lysimachia fortunei Maxim,which resulted in the isolation and idetification of 35 and 12 compounds from the two medical plants respectively.C.japonicum belongs to the genus Verbenaceae of the family Clerodendrum,it is mainly distributed in southern provinces of China.The whole plants has been used as folk medicines in Guangxi and Yunnan for the treatment of rheumatic bone pain,lumbar muscle strain,injury,tuberculosis,cough and so on.By means of solvent partition,repeated normal and reversed phase column chromatography on silica gel and Pre-HPLC,35 compounds were isolated.Based on chemical method and spectroscopic analyses?HR-ESIMS,1D-NMR,2D-NMR?,their structures were identified as japonicum cyclic pentapeptide A?1?,japonicum cyclic pentapeptide B?2?,hydroxyhomodestruxin B?3?,hydroxydestruxin B?4?,7?-hydroxy syringaresinol?5?,medioresinol?6?,?-?-syringaresinol?7?,martinoside?8?,2??-O-acetylmartyonside?9?,monoacetyl martinoside?10?,clerodenoside A?11?,cytochalasin O?12?,9-epi-blumenol B?13?,?6R,9S?and?6R,9R?9-hydroxy-4-megastigmen-3-one?14?,?6R,9S?-3-oxo-?-ionol?15?,?-?-dehydrovomifoliol?16?,megastigm-5-en-3,9-diol?17?,?3R,6E,10S?-2,6,10-trimethyl-3-hydroxydodeca-6,11-diene-2,10-diol?18?,?2R?-butylitaconic acid?19?,3-?3?-hydroxybutyl?-2,4,4-trimethylcyclohexa-2,5-dienone?20?,?-?-loliolide?21?,5-hydroxymaltol?22?,argutone?23?,decumbic acid?24?,cis-2,4-dihydroxy-2-?2-hydroxyethyl?cyclohex-5-en-1-one?25?,5-hydroxymethyl furfural?26?,fumaric acid?27?,3,4-dihydroxybenzoic aldehyde?28?,p-hydroxyphenylethanol?29?,4-hydroxybenzoic acid?30?,parahydroxyben-zaldehyde?31?,terephthalic acid?32?,trans-p-hydroxycinnamic acid?33?,cis-p-hydroxycinnamic acid?34?,2-?4-methoxyphenyl?acetic acid?35?.Among of them,compounds 1 and 2 were new compounds,except for compounds 9-11,the other were isolated from this plant for the first time.L.fortunei belongs to the genus Primulance of the family Lysimachia,it is widely distributed in the southern and eastern provinces of China.It has been used for the treatment of cold and fever,sore throat,liver cirrhosis,dysentery,enteritis,snake bite and so on.12 compounds were isolated by using solvent partition,repeated normal and reversed phase column chromatography on silica gel and Pre-HPLC.Based on chemical method and spectroscopic analysis?HRESI-MS,1D-NMR,2D-NMR?,their structures were identified as fortunoside A-F?36-41?,3?-{a-L-rhamnopyranosyl-?1?2?-?-D-glucopyranosyl-?1?4?-[?-D-glucopyranosyl-?1?2?]-a-L-arabinopyranosyloxy}-13?,28-epoxy-16a-hydroxyoleanane?42?,lysikoianoside l?43?,ardisianoside C?44?,ardisimamiloside E?45?,candidoside?46?,3?-{a-Lrhamnopyranosyl-?1?2?-?-D-glucopyranosyl-?1?4?-[?-D-glucopyranosyl-?1?2?]-a-L-arabinopyranosyloxy}-16a,28-dihydroxyolean-12-ene?47?.Among of these compounds,compounds 36-41 were new compounds,all compounds were isolated from the plant for the first time.Compounds 1-4 and 36-47 were tested on the antitumor activity by MTT method.Compounds 1-4 showed weak antitumor activity?23.78-39.62?M?.While the results of compounds 36-47 shows that sponins 42-44 with the aglycone protoprimulagenin A exhibited moderate cytotoxicity against all of the tested human cancer cell lines,with IC₅₀ values of 4.76-15.12?M.Among the 13?,28-epoxyoleanane-type triterpenoid saponins?36-39,42-45?,compounds 36-39 and 45,containing a hydroxy group at C-12,C-21,or C-29,were inactive(IC₅₀>50?M),which suggested that the hydroxy group on these carbons might decrease the resultant cytotoxic activity.