| The branches and leaves of Nageia fleuryi Hickel and Beaumontia grandiflora Wall were commonly used as traditional folk medicine to treat a variety of inflammatory diseases.Therefore,exploration of their extracts was helpful to the discovery of anti-inflammatory components.In this report,N.fleuryi and B.grandiflora were chemically investigated,and a total of 71 compounds including 6 new ones were isolated.The new compounds and terpenoids obtained in this research were tested for their anti-inflammatory,anti-oxidant,and cytotoxic activities,and one of the compounds exhibited biological activities in vitro.Many kinds of compounds were found through the isolation of the chemical constituents of N.fleuryi and B.grandiflora,which led to enrich ment of the natural products database.Some compounds with strong bioactivities were found in the in vitro bioassay,which provided a basis for further study of anti-inflammatory,anti-cancer,and anti-oxidant drugs and the structure-activity relationship of compounds.The chemical constituents of the ethanolic extract of the twigs and leaves of N.fleuryi were studied systematically.46 compounds were obtainted after column chromatography of Sephadex LH-20 and silica gel,as well as semi-preparative HPLC,including 40 known and six new ones.The new compounds were characterized as three diterpenoids,12,15-di-O-acetylhypargenin B(1),taiwanin F-12-O-β-D-glucopyranoside(2),and 2-hydroxytotarol-1-ene-3-one(3);one monoterpenoid,(S)-1,2-di-O-acetylmyrcene(4);one megastigmane,(9R)-hydroxymegastigman-5-en-4-one-9-O-β-D-glucopyranoside(5);one butenolide,(S)-3,4-dimethyl-5-pentylfuran-2(5H)-one-5-O-β-D-glucopyranoside(6).The 40 known compounds were identified as ten diterpenoids,sugiol(7),12-O-demethylcryptojaponol(8),6a-hydroxysugiol(9),hypargenin B(10),inumakiol A(11),lambertic acid(12),4β-carboxy-19-nor-totarol(13),totaradiol(14),nagilactone G(15),and nagilactone B(16);eight flavonoids,quercetin-3-O-β-D-glucopyranoside(17),kaempferol-3-O-β-D-glucopyranoside(18),apigenin-7-O-β-D-glucopyranoside(19),2S-5,3’,5’-trihydroxyflavanone-7-O-β-D-glucopyranoside(20),2R-5,3’,5’-trihydroxyflavanone-7-O-β-D-glucopyranoside(21),catechin(22),epicatechin(23),and hinokiflavone(24);one monoterpenoid,(S)-1,2-dihydroxymyrcene(25);two sesquiterpenoids,byzantionoside A(26)and 4-hydroxy-4,7-dimethyl-l-tetralone(27);one butenolide,(S)-5-hydroxy-3,4-dimethyl-5-pentylfuran-2(5H)-one(28);two steroids,β-sitosterol(29)and daucosterol(30);three lignans,6-hydroxyhinokinin6-O-β-D-glucopyranoside(31),threo-guaiacylglycerol-β-O-4-lariciresinol ether(32),and buddlenol D(33);six aromatics,m-hydroxybenzoic acid(34),protocatechuic acid(35),p-hydroxybenzoic acid(36),2-guaiacylpropane-1,3-diol(37),vanillin(38),and 4-hydroxybenzaldehyde(39);seven fatty acids,(4S,2E)-4-hydroxy-2-nonenoic acid(40),(E)-4-hydroxyhex-2-enoic acid(41),rabdosia acid A(42),(9E,11Z)-13-oxo-9,11ocatadecadienoic acid(43),12-hydroxyoctadeca-9,13,15-trienoic acid methyl ester(44),(5)-15,16-didehydrocoriolic acid(45),and α-dimorphecolic acid(46).Among them,compounds 1 and 13 dose-dependently inhibited LPS-induced overproduction of NO in RAW 264.7 murine macrophages.In Hepa 1 c1c7 murine hepatoma cells,compounds 1,4,7,8,11,and 25 showed different levels of quinone reductase inducing activity.Compounds 15 and 16 exhibited strong inhibitory activity against the proliferation of DU 145(human prostate carcinoma)cells.The chemical constituents of the ethanolic extract of the twigs and leaves of B.grandiflora were studied systematically,and a total of 26 known compounds were obtained.The compounds were characterized as three steroids,β-sitosterol(29),androsta-4,6,8,14-tetraene-3,11,16-trione(47),and stigmasterol(48);two triterpenoids,oleanolic acid(49)and camaldulenic acid(50);three coumarins,scopoletin(51),cleomiscosin A(52),and hemidesmin-1(53);four lignans,(7S)-3-methoxy-4-hydroxy-7hydroxymethylphenylacetic acid-8-O-(3’-methoxyl-4’-hydroxy)phenyl ester(54),evofolin B(55),8-hydroxypinoresinol(56),and pinoresinol(57);six phenylpropanoids,3-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propan-1-one(58),ω-hydroxypropioguaiacone(59),sinapaldehyde(60),coniferyl aldehyde(61),trans-ferulic acid(62),and-hydroxycinnamic acid(63);five aromatics,a-hydroxyacetosyringone(64),3,5-dimethoxy-4-hydroxy-benzaldehyde(65),phenylacetic acid(66),protocatechuic acid ethyl ester(67),and vanillic acid(68);and three miscellaneous,2,5-dimethoxybenzoquinone(69),glyceroyl monopalmitate(70),and grasshopper ketone(71). |
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