The Chemical Constituents and Their Bioactivities of Nauclea Officinalis Pierre Ex Pitard and Turpinia Arguta Seem
|Keywords||Nauclea officinalis Pierre ex Pitard Turpinia arguta Seem indole alkaloid NO antimalarial activity|
Nauclea officinalis Pierre ex Pitard belongs to the genus Nauclea and the family Rubiaceae.It is distributed throughout southern China.The stems and bark of Nauclea officinalis Pierre ex Pitard have traditionally been used as a folk medicine named "Danmu".It is bitter in taste and cold-natured.Therefore,it has heat-clearing, detoxicating,discussive and painkilling functions and is widely used to cure colds, fever,swelling of throat,pink eye,enteritis,dysentery,eczema and other ailments. Now,its extracts have been made into two forms of medication:one is tablet,the other is injection.Both of them have been used as anti-inflammatory and antibacterial traditional agents in clinic.Turpinia arguta Seem belongs to the genus Turpinia of the family Staphyleaceae distributed in Gannan regions of Jiangxi province.It has heat-clearing,detoxicating,reducing pharyngeal swelling function. The leaves of Turpinia arguta Seem have been used to treat pharyngeal inflammation in clinic.However,up to now,the active constituents of anti-inflammatory and mechanisms about both of the herbs are still not clear.Therefore,by means of modern chemical theory and isolation technique,the plants mentioned above were studied systemically and the structures of the compounds from them were also elucidated and screened for biological activities.By means of chromatography technique,thirty-eight compounds were isolated, purified from the MeOH extract of Nauclea officinalis Pierre ex Pitard（stems with bark）.On the basis of their chemical and physical properties as well as the spectral data of IR,ESI-MS,FAB-MS,HR-MS,1D-NMR,2D-NMR,et al.,compared with data reported in literatures,the structures of 38 compounds were elucidated or determined,including 22 indole alkaloids,11 triterpenoids,3 steroids,1 flavonoid glycoside and 1 lignin.They are naucleofficine F（N1）,naucleofficine G（N2）, naucleofficine A（N5）,naucleofficine B（N6）,naucleofficine C（N7）,naucleofficine D （N3）,naucleofficine E（N8）,naucleofficine H（N4）,naucleofficine I（N9）, naucleofficine J(N10),2β,3β,19a,23-tetrahydroxyurs-12-en-28-oic acid(N11), 2β,3β,19α,23-tetrahydroxyurs-12-en-28-oic acid-28-β-D-glucopyronosyl-（1→2）-β-D-gluc-opyronosyl ester(N12),3β,19a,23,24-tetrahydroxyurs-12-en-28-oic acid (N13),3-（hydroxymethyl）-6,7-dihydroindolo[2,3-a]quinolizin-4（12H）-one(N14), pumilos-ide(N15),vincosamide(N16),strictosamide(N17),10-hydroxyvincosamide (N18),naucleamide B(N19),angustoline(N20),naucleamide E(N21),nauclefi-dine (N22),naucleidinal(N23),nauclefine(N24),angustine(N25),pyrocincholic acid-3β-O-a-L-rhamnopyranosyl-28-β-D-glucopyranosyl-（1→6）-β-D-glucopyranos yl ester(N26),pyrocincholie acid-3β-O-a-L-rhamnopyranosyl-28-β-D-glucopyranosyl ester(N27),pyrocincholic acid-3β-O-a-L-rhamnopyranoside(N28),quinovic acid (N29),3-oxo-quinovic acid(N30),quinovie acid-3β-O-β-D-glucopyranoside(N31), quinovic acid-3β-O-a-L-rhamnopyranoside(N32),quinovic acid-3β-O-a-L-rhamnopyranosyl -28-β-D-glucopyranosyl ester(N33),hesperetin 7-O-（6″-O-a-L-rhamnopyranosyl） -β-D-glu-copyranoside(N34),glycosmisic acid(N35),stigmast-4-en-3-one (N36),β-sitosterol(N37)and daucosterol(N38).Twelve compounds(N1,N2,N3,N4, N5,N6,N7,N8,N9,N10,N11and N12)of them were elucidated to be new. Furthermore,seven compounds(N13,N18,N26,N27,N28,N33and N34,including 3 nortriterpenoids)were isolated and identifced from this genus for the first time and three compounds(N21,N25and N32)were isolated and identified from this plant for the first time.According to the clinical application of Nauclea officinalis Pierre ex Pitard and the reported secondary metabolites from the genus Nauclea,the compounds of this species were screened for the anti-inflammatory,antimalarial,anti-tumor and DPPH radical scavenging activities.With respect to the bioassay,the compounds isolated from the MeOH extract of Nauclea officinalis Pierre ex Pitard displayed moderate anti-inflammatory（NO）,antimalarial,anti-tumor and DPPH radical scavenging activities.Anti-inflammatory IC50values of compounds N28,N1,N24,N20,N5 are 1.31μM,1.37μM,1.58μM,2.65μM and 8.88μM.Antimalarial IC50values of compounds N5,N20are 9.7μM and 20.5μM.DPPH radical scavenging IC50values of compound N18is 400μM.Nineteen compounds were isolated from the leaves of Turpinia arguta Seem and their structures were identified with the aid of spectroscopic analyses and chemical methods.These compounds are as follows:apigenin（T1）,apigenin 7-glucoside（T2）, apigenin 7-neohesperidoside（T3）,apigenin 7-2′-rhamnosyl-rotinoside（T4）,ursolic acid（T5）,pomolic acid（T6）,corosolie acid（T7）,tormentie acid（T8）,maslinic acid （T9）,tormentic acid 28-O-β-D-glucopyrano-syl ester(T10),arjunolie acid 28-β-D-glucopyranosyl ester(T11),2α,3β,23,29-tetrahydroxyolean-12-en-28-oie acid 28-β-D-glucopyranosyl ester(T12),2α,3β,19α,23-tetrahydroxyurs- 12-en-28-oic acid 28-β-D-glucopyranosyl ester(T13),p-hydroxycinnamic acid(T14),ethyl gallate(T15),gallic acid(T16),eucomie acid(T17),β-sitosterol(T18)and daucosterol(T19).Ten compounds of them(T4,T9,T10,T11,T12,T13,T14,T15,T17and T19)were isolated and identified from this genus for the first time.On the basis of the chemical constituents research,the anti-inflammatory activeities were screened.The compounds from the Turpinia arguta Seem displayed moderate anti-inflammatory（NO）and DPPH radical scavenging activities.Anti-inflammatory IC50values of compounds T1,T8,T5,T9 are 3.60μM,3.64μM,4.03μM, 6.07μM.DPPH radical scavenging IC50values of compounds T15,T16are 44μM and 40μM.