| Morinda genus belongs to the family Rubiaceae which includes approximately 102 Morinda species in the world.Most research was studied about Morinda officinalis and Morinda citrifolia in the genus,from which quinones,iridoids,flavonoids and lignans were isolated.They showed various biological activities,such as antioxidation,anti?inflammatory,cytotoxic,antibacteria,hepatoprotection,antidepressant and immunoregulation activities,and so on.Morinda parvifolia is a traditional medicinal plant of the genus Morinda.It was recorded in Xinhua Outline of Materia Medica,which has the function of clearing heat and relieving cough,removing blood stasis and alleviating pain,harmonizing the stomach and defaecation.However,only a few researches about the biological activity and the chemical composition of M.parvifolia has been studied.Therefore,to further study the bioactive compounds in this plant is important.The 95%ethanol extract of aerial parts of M.parvifolia was used to investigate the chemical composition and pharmacological activity.The extract was subjected to medium pressure C-18 column chromatography,Diaion HP-20 macroporous resin column chromatography,Sephadex LH-20 column chromatography and preparative HPLC to obtain 71 compounds,including 21 new compounds(1*-21*).These compounds were composed of 17 quines(1*-10*,22-28),12 flavonoids(16*-18*,29-37),18 terpenes(11*-13*,38-52),nine benzoic acids and benzosides(19*-21*,59-61,66-68),five chlorogenic acids(53-57)and ten other compounds(14*-15*,58,62-65,69-71).Their structures were identified on the basis of spectroscopic and chemical methods.They were characterized as morindaparvins H-ZB(1*-21*),rubiadin 3-O-?-primerveroside(22),lucidine-3-O-?-D?primerveroside(23),damnacanthol-3-O-?-D-primerveroside(24),alizarin 1-methyl ester 2-O-?-D-primerveroside(25),rubinaphthin A methyl ester(26),2-carboxyanthraquinone(27),3-hydroxyanthraquinone-2-carboxylic acid(28),isohamnetin-3-O-?-D-glucopyranosyl-(1-6)-?-D-glucopyranosyl-7-O-?-D-glucopyranoside(29),isorhamnetin-3-O-?-gentiobioside(30),isohamnetin 3-O-[a-L-rhamnopyranosyl-(1?6)-?-D-glucopyranoside(31),kaempferol-3-O-?-gentiobioside(32),isorhamnetin 3-O-?-D-glucopyranoside(33).puerarin(34),3'-methoxy puerarin(35),daidzein 4',7-di-O-?-D-glucopyranoside(36),daidzein 7-O-glucopyranoside(37),10-O-benzoyl-6-O-a-L-arabinosyl-(1?6)-?-D-glucopyranosyl geniposidic acid(38),deacetylasperuloside(39),secologanoside(40),6a-hydroxyadoxoside(41),monotropein(42),geniposidic acid(43),ixoside(44),deacetylasperulosidic acid(45),methyl deacetylasperulosidate(46),9-epi-6a-methoxy geniposidic acid(47),scandoside(48),scandoside methyl ester(49),(6S,9R)?vomifoliol-9-O-?-xylopyranosyl-(1"?6')-O-?-glucopyranoside(50),dihydrophaseic acid 4'-O-?-D-glucopyranoside(51),4'-dihydrophaseic acid(52),chlorogenic acid(53),chlorogenic acid methyl ester(54),3-caffeoylquinic acid(55),cryptochlorogenic acid methyl ester(56),4-O-p-coumaroylquinic acid(57),cis-p-coumaric acid 4-O-?-D-glucopyranoside(58),vanillic acid 4-O-?-D-(6'-sinapoyl)-glucopyranoside(59),3,5-dimethoxy benzoic acid 4-O-?-D-glucopyranoside(60),3-methoxy-benzoic acid 4-O-?-D-glucopyranoside(61),3-methoxy-4-hydroxyphenol 1-O-?-D-glucopyranoside(62),3,4,5-trimethoxyl-phenyl-1-O-?-D-glucopyranoside(63),ficuscarpanoside B(64),2-formyl-5-hydroxymethyl-1H-pyrrole-l-pentanoic acid(65),3-O-methylgallic acid(66),3,4-dihydroxy benzoic acid(67),4-hydroxybenzoic acid(68),trans 4-hydroxycinnamic acid(69),cis 4-hydroxycinnamic acid(70),5-hydroxymethy1-2-furfural(71).Naphthohydroquinone glycosides(1*-3*)connecting sinapoyl fragment were found for the first time.EtOH extract chromatograms of HPLC/(-)ESIMS proved that they were not artefacts.Dioxane compounds(14*-15*)were first isolated from Morinda genus.Compounds 1*-21*,24,28-38,40,44,51,52,55-60,62-66,69 and 70 were obtained from this genus for the first time.We screened the pharmacological activity of the purified compounds.New compounds 3*,5*,6*,10*,11*,14*,15*,16*,17*and known compounds 23,25,27,29,35,50,53,54,55,56,67,69,70,71 showed significant hepatoprotective activities against acetaminophen(APAP)-induced toxicity in HepG2 cell at the concentration of 10 ?M.In the cytotoxic experiments,new compound 10*showed moderate cytotoxicity against cutaneous squamous cell carcinoma A431,ovarian cancer A2780,lung cancer H460 and liver cancer H7402 cell lines with IC50 values of 25.9,31.8,34.8 and 25.6 ?M,respectively.However,the other tested compounds did not exhibit cytotoxic activities.Compounds 33,53 and 56 showed inhibitory activity against aldose reductase with inhibitory ratio of 85.7%,112.1%and 114.3%,respectively.All compounds did not show any inhibitory effect against NO production by lipopolysaccharide(LPS)induced macrophages. |
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