Chemical constituents from fruits of Morinda citrifolia and their inhibitory effects on proliferation of synoviocytes in vitro / 中国中药杂志

The chemical constituents from the fruits of Morinda citrifolia were systematically explored by chromatographic fractionation methods including silica gel, octadecylsilyl(ODS) gel, Sephadex LH-20 gel, and preparative high performance liquid chromatography(pre-HPLC). The chemical structures of all isolated compounds were identified on the basis of their physicochemical properties, spectroscopic analyses, as well as the comparisons of their physicochemical and spectroscopic data with the reported data in literature. As a result, 22 isolated compounds from the 90% ethanol extract of the fruits of M. citrifolia were identified, which were moricitritone(1), 2'-deoxythymidine(2), cyclo-(L-Pro-L-Tyr)(3), methyl-5-hydroxy-2-pyridinecarboxylate(4), methyl pyroglutamate(5), bisbenzopyran(6), epipinoresinol(7), 3, 3'-bisdemethyl pinoresinol(8), 3, 3'-bisdemethyltanegool(9), trimesic acid(10), crypticin B(11), kojic acid(12), vanillic acid(13), protocatechoic acid(14), 5-hydroxymethyl furfural(15), blumenol A(16), 1-O-(9Z, 12Z-octadecadienoyl) glycerol(17), mucic acid dimethylester(18), methyl 2-O-β-D-glucopyranosylbenzoate(19), 2-phenylethyl-O-β-D-glucoside(20), scopoletin(21), and quercetin(22). Among them, compound 1 was a new pyrone derivative, compounds 2, 4-7, 10-12, and 17 were isolated from the plants belonging to Morinda genus for the first time, and compound 18 was obtained from M. citrifolia for the first time. Moreover, on the basis of testing the activities of all isolated compounds on inhibiting the proliferation of synovial fibroblasts in vitro by MTS assay, the anti-rheumatoid arthritis activities of all isolated compounds were initially evaluated. The results showed that compounds 1-6, 9, 19, and 20 exhibited remarkable anti-rheumatoid arthritis activities, which displayed the inhibitory effects on the proliferation of MH7A synovial fibroblast cells with the IC_(50) values in the range of(3.69±0.08) to(168.96±0.98) μmol·L~(-1).

Chemical constituents from stems and leaves of Cratoxylum cochinchinense and their inhibitory effects on proliferation of synoviocytes in vitro / 中国中药杂志

The chemical constituents from the stems and leaves of Cratoxylum cochinchinense were isolated and purified using silica gel, ODS gel, and Sephadex LH-20 gel column chromatography, as well as preparative HPLC. The chemical structures of all isolated compounds were identified on the basis of their physicochemical properties, spectroscopic analyses, and the comparison of their physicochemical and spectroscopic data with the reported data in literature. As a result, 21 compounds were isolated from the 90% ethanol extract of the stems and leaves of C. cochinchinense, which were identified as cratocochine(1), 1-hydroxy-3,7-dimethoxyxanthone(2), 1-hydroxy-5,6,7-trimethoxyxanthone(3), ferrxanthone(4), 3,6-dihydroxy-1,5-dimethoxyxanthone(5), 3,6-dihydroxy-1,7-dimethoxyxanthone(6), 1,2,5-trihydroxy-6,8-dimethoxyxanthone(7), securixanthone G(8), gentisein(9), 3,7-dihydroxy-1-methoxyxanthone(10), pancixanthone B(11), garcimangosxanthone A(12), pruniflorone L(13), 9-hydroxy alabaxanthone(14), cochinchinone A(15), luteolin(16), 3,5'-dimethoxy-4',7-epoxy-8,3'-neolignane-5,9,9'-triol(17), N-benzyl-9-oxo-10E,12E-octadecadienamide(18), 15-hydroxy-7,13E-labdadiene(19), stigmasta-4,22-dien-3-one(20), and stigmast-5-en-3β-ol(21). Among these isolates, compound 1 was a new xanthone, compounds 2-5, 7, 8, 12, and 16-21 were isolated from the Cratoxylum plant for the first time, and compounds 11 and 13 were obtained from C. cochinchinense for the first time. Furthermore, all isolated compounds 1-21 were appraised for their anti-rheumatoid arthritis activities by MTS method through measuring their anti-proliferative effect on synoviocytes in vitro. As a result, xanthones 1-15 displayed notable anti-rheumatoid arthritis activities, which showed inhibitory effects on the proliferation of MH7A synoviocytes with the IC_(50) values ranging from(8.98±0.12) to(228.68±0.32) μmol·L~(-1).

Chemical constituents from Clausena excavata and their inhibitory activities against proliferation of synoviocytes / 中国中药杂志

The chemical constituents from the stems and leaves of Clausena excavata were isolated and purified by column chromatography with silica gel, ODS, Sephadex LH-20 and RP-HPLC. The chemical structures of the isolated compounds were identified on the basis of physicochemical properties, spectroscopic analysis, as well as the comparisons with the data reported in literature. Nineteen compounds were isolated from the 90% ethanol extract of the stems and leaves of C. excavata, which were identified as methyl orsellinate(1), syringaresinol(2), lenisin A(3), scopoletin(4), osthenol(5), N-benzoyltyrarnine methyl ether(6), N-p-coumaroyltyramine(7), aurantiamide acetate(8), 1H-indole-3-carboxaldehyde(9), furostifoline(10), clausenalansine E(11), 3-formylcarbazole(12), clausine L(13), clausine E(14), methyl carbazole-3-carboxylate(15), glycosinin(16), murrayafoline A(17), clausine H(18) and 2,7-dihydroxy-3-formyl-1-(3'-methyl-2'-butenyl)carbazole(19). Among these isolated compounds, compounds 1-11 were isolated from C. excavata for the first time, and compounds 1, 2 and 10 were isolated from the genus Clausena for the first time. In addition, this study evaluated the anti-rheumatoid arthritis activities of compounds 1-19 by measuring their anti-proliferative effects on synoviocytes in vitro according to MTS method. Compounds 10-19 displayed remarkable anti-rheumatoid arthritis activities, which exhibited the inhibitory effects on the proliferation of MH7 A synovial fibroblast cells with the IC_(50) values ranging from(27.63±0.18) to(235.67±2.16) μmol·L~(-1).

Chemical constituents from Morinda citrifolia and their inhibitory activities on proliferation of synoviocytes in vitro / 中国中药杂志

The chemical constituents from the stems and leaves of Morinda citrifolia were isolated and purified by column chromatography methods with silica gel, ODS, Sephadex LH-20 and preparative high performance liquid chromatography(HPLC). The structures of the isolated compounds were identified by physicochemical properties and spectroscopic analysis, as well as comparisons with the data reported in literature. 17 compounds were isolated from the 90% ethanol extract of the stems and leaves of M. citrifolia, and were identified as 9,10-dihydroxy-4, 7-megastigmadien-3-one(1), 5,12-epoxy-6,9-hydroxy-7-megastigmen-3-one(2), fukinone(3), β-eudesmol(4), sarmentol F(5), 4, 5-dihydroblumenol A(6), 3-hydroxy-β-ionone(7), aristol-8-en-1-one(8), ergosta-7-en-3β-ol(9), ergosta-7-ene-3β,5α,6β-triol(10),(22E)-5α,8α-epidioxyergosta-6,22-dien-3β-ol(11), olivil(12), 4-epi-larreatricin(13), chushizisin Ⅰ(14), rabdosia acid A(15), glycerol monolinoleate(16) and(9Z,12Z,15Z)-2,3-dihydroxypropyl octadeca-trienoate(17). All compounds were isolated from M. citrifolia for the first time. All isolated compounds were evaluated for their anti-rheumatoid arthritis activities via examining their inhibitory activities on the proliferation of synoviocytes in vitro using MTS met-hod. Compounds 1-11 showed significant anti-rheumatoid arthritis activities, displaying the inhibitory effects on the proliferation of MH7 A synovial fibroblast cell with the IC_(50) values ranging from(38.69±0.86) to(203.45±1.03) μmol·L~(-1).

Chemical constituents from stems and leaves of Clausena emarginata / 中国中药杂志

The chemical constituents from the stems and leaves of Clausena emarginata were separated and purified by column chromatographies on silica gel,ODS,Sephadex LH-20,and PR-HPLC. The structures of the isolated compounds were identified on the basis of physicochemical properties and spectroscopic analysis,as well as comparisons with the data reported in the literature. Sixteen compounds were isolated from the 90% ethanol extract of the stems and leaves of C. emarginata,which were identified as siamenol( 1),murrastanine A( 2),3-formyl-1,6-dimethoxycarbazole( 3),3-methoxymethylcarbazole( 4),3-methylcarbazole( 5),murrayafoline A( 6),3-formylcarbazole( 7),3-formyl-1-hydroxycarbazole( 8),3-formyl-6-methoxycarbazole( 9),murrayanine( 10),murrayacine( 11),girinimbine( 12),nordentatin( 13),chalepin( 14),8-hydroxy-6-methoxy-3-pentylisocoumarin( 15) and ethyl orsellinate( 16). Compounds 1-4,14-16 were isolated from C. emarginata for the first time. Among them,compounds 1,2,15 and 16 were isolated from the genus Clausena for the first time. All isolated compounds were evaluated for their cytotoxic activities against five human cancer cell lines: HL-60,SMMC-7721,A-549,MCF-7 and SW480 in vitro. Compounds 12 and 14 showed significant inhibitory effects against various human cancer cell lines with IC_(50) values comparable to those of doxorubicin.

Chemical constituents from fruiting bodies of Tremella sanguinea / 中国中药杂志

The chemical constituents from the fruiting bodies of Tremella sanguinea were separated and purified by column chromatography on silica gel,ODS,Sephadex LH-20,and RP-HPLC. The structures of the isolated compounds were identified on the basis of physicochemical properties and spectroscopic data analysis,as well as comparisons with the data reported in the literature. Sixteen compounds were isolated from the 90% ethanol extract of the fruiting bodies of T. sanguinea,which were identified as( 22 E)-5α,8α-epidioxy-24-methyl-cholesta-6,9( 11),22-trien-3β-ol( 1),( 22 E)-5α,8α-epidioxyergosta-6,22-dien-3β-ol( 2),cerevisterol( 3),ergosta-7-ene-3β,5α,6β-triol( 4),( 22 E)-6β-methoxyergosta-7,22-diene-3β,5α-diol( 5),ergosta-7-en-3β-ol( 6),4-hydroxy-methylincisterol( 7),2-pyrrolidone( 8),nicotinamide( 9),1-( 3-indolyl)-3-dihydroxypropan-1-one( 10),yangambin( 11),linoleic acid( 12),( 9 Z,12 Z,15 Z)-2,3-dihydroxypropyl octadeca-trienoate( 13),( 9 Z,12 Z)-2,3-dihydroxypropyl-octadeca-dienoate( 14),crypticin B( 15)and 3-phenyllactic acid( 16). All compounds were isolated from T. sanguinea for the first time. Except for compounds 6,9 and 12,the remained compounds were isolated from the genus Tremella for the first time.

Chemical constituents from stems and leaves of Psychotria serpens / 中国中药杂志

The chemical consituents from the stems and leaves of Psychotria serpens were separated and purified by column chromatographies with silica gel, ODS, Sephadex LH-20 and PR-HPLC. The structures of the isolated compounds were identified on the basis of physicochemical properties and spectroscopic analyses, as well as comparisons with the data reported in literature. 18 compounds were isolated from the 90% ethanol extract of the stems and leaves of P. serpens, which were identified as chrysin(1), acacetin(2), genkwanin(3), chrysoeriol(4), rhamnocitrin(5), isorhamnetin(6), tricin(7), jaceosidin(8), dillenetin(9), kumatakenin(10), ayanin(11), isosakuranetin(12), eriodictyol(13), homoeriodictyol(14), taxifolin(15), pomonic acid(16), fupenzic acid(17) and euscaphic acid(18). All compounds were isolated from the genus Psychotria for the first time.

Sesquiterpenes from Artabotrys hongkongensis / 中国中药杂志

The chemical consituents from Artabotrys hongkongensis were separated and purified by column chromatographies with silica gel, Sephadex LH-20, ODS and RP-HPLC. The structures of the isolated compounds were identified on the basis of physicochemical properties and spectroscopic analysis, as well as comparisons with the data reported in the literature. As a result, 16 sesquiterpenes were isolated and elucidated as blumenol A (1), 4, 5-dihydroblumenol A (2), (6R, 9S)-3-oxo-a-ionol (3), 3-hydroxy-β-ionone (4), dehydrovomifoliol (5), (3R, 6R, 7E) -3-hydroxy-4, 7-megastigmadien-9-one (6), sarmentol F (7), 10-oxo-isodauc-3-en-15-oic acid (8), fukinone (9), petasitolone (10), β-eudesmol (11), trans-3β-(1-hydroxy-1-methylethyl)- 8aβ-methyl-5-methylenedecalin-2-one (12), 10-hydroxyaristolan-9-one (13), aristol-8-en-1-one (14), aristolan-9-en-1-one (15), and aristolan-1, 9-diene (16). This is the first study on the chemical consituents of A. hongkongensis, and all compounds were isolated from the genus Artabotrys for the first time.

Studies on alkaloids from Fissistigma oldhamii / 中国中药杂志

14 alkaloids were obtained from stems and leaves of Fissistigma oldhamii, by silica gel, ODS, Sephadex LH-20 column chromatographies, and semi-preparative HPLC. Using physicochemical and spectral methods, the isolated alkaloids were identified as norcepharadione B(1), asimilobine(2), lanuginosine(3), laurotanine(4), isocorydine(5), anolobine(6), xylopine(7), N-methylbuxifoline(8), aristolactam AIIIa(9), piperumbellactam A(10), goniopedaline(11), aristololactam BIII(12), liriodenine(13), and salutaridine(14), respectively. Compounds 3-5, 8, 10, 11 and 14 were isolated from the genus Fissistigma for the first time.

Studies on chemical constituents from Psychotria straminea / 中国中药杂志

The chemical consituents from Psychotria straminea were separated and purified by column chromatographies on silica gel, Sephadex LH-20, ODS and RP-HPLC. The strictures of the isolated compounds were identified on the basis of physicochemical properties and spectroscopic analysis, as well as comparisons with the data in literature. Sixteen compounds were isolated and elucidated as tectochrysin (1), apigenin (2), kaempferol (3), luteolin (4), diosmetin (5), quercetin (6), kaempferol-4'-O-methylether (7), rhamnetin (8), 7-hydroxycoumarin (9), 7-methoxycoumarin (10), scopoletin (11), lupeol (12), 30-oxo-lupeol (13), lupenyl acetate (14), α-amyrin (15), and ursolic acid (16). This is the first study on the chemical composition of P. Straminea, and all compounds were isolated from P. straminea for the first time. In addition to compounds 6 and 9, the other compounds were isolated from the genus Psychotria for the first time.