ABSTRACT
Nine new glucosyloxybenzyl 2-hydroxy-2-isobutylsuccinates, pleionosides M-U (1-9), and 12 known compounds (10-21) were isolated from the pseudobulbs of Pleione yunnanensis. Their structures and absolute configurations were established through a combination of HRESIMS and NMR data and supported by physical and chemical methods. Compounds 5, 6, 10, and 15 showed significant in vitro hepatoprotective activity against d-galactosamine (d-GalN)-induced toxicity in HL-7702 cells with increasing cell viability by 27%, 22%, 19%, and 31% compared to the model group (cf. bicyclol, 14%) at 10 µM, respectively. Compounds 4, 9, and 11 exhibited moderate hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced toxicity in HepG2 cells with increasing cell viability by 9%, 16%, and 12% compared to the model group (cf. bicyclol, 9%) at 10 µM, respectively.
Subject(s)
Orchidaceae/chemistry , Protective Agents/pharmacology , Succinates/pharmacology , Acetaminophen , Cell Survival/drug effects , China , Hep G2 Cells , Humans , Molecular Structure , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , Protective Agents/isolation & purification , Succinates/isolation & purificationABSTRACT
Three new dammarane triterpenoid saponins, cyclocariosides O-Q (1-3), were isolated from the ethanolic extracts of the leaves of Cyclocarya paliurus. The structures of these compounds were elucidated by spectroscopic methods.
Subject(s)
Juglandaceae/chemistry , Plant Leaves/chemistry , Saponins/chemistry , Triterpenes/chemistry , Acetaminophen/toxicity , Analgesics/toxicity , Animals , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Cell Line, Tumor , Chemical and Drug Induced Liver Injury/prevention & control , Humans , Mice , Molecular Structure , RAW 264.7 Cells , Tumor Necrosis Factor-alpha/antagonists & inhibitorsABSTRACT
Eighteen compounds were isolated from the EtOAc soluble fraction of Bletilla striata by various chromatographic techniques, such as silica gel, ODS, Sephadex LH-20, RP-HPLC. Their structures were identified by spectroscopic methods and physicochemical properties, as 5-hydroxy-2-(p-hydroxybenzyl)- 3- methoxybibenzyl(1), shancigusins B(2), shanciguol(3),arundinan(4), 3',5-dihydroxy-2,4-di(p-hydroxybenzyl)-3-methoxybibenzyl(5), arundin(6), 3,3'-dihydroxy-2-(p-hydroxybenzyl)-5-methoxybibenzyl(7), 3, 3'-dihydroxy-2', 6'-bis(p-hydroxybenzyl)-5-methoxybibenzyl(8), 7-hydroxy-2,4-dimethoxyphenanthrene(9), bleformin B(10),nudol(11), 3,7-dihydroxy-2, 4-dimethoxyphenanthrene(12), 2, 7-dihydroxy-4-methoxy-9,10-dihydrophenathrene(13), bleformin D(14), 4,4'-dimethoxy-9,10-dyhydro-[6,1'-biphenanthrene]-2,2',7,7'-tetraol(15),gymconopin C(16),(2,3-trans)-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-10-methoxy-2,3,4,5-tetrahydro-phenanthro[2,1-b]furan-7-ol(17),shanciol(18). Among them, compound 1 was a new compound, Compounds 2-6,9,15-18 were isolated from this genus for the first time.
Subject(s)
Orchidaceae/chemistry , Phytochemicals/analysis , Plant Tubers/chemistryABSTRACT
Twelve hydrolyzable tannins were obtained from the twigs of Myricaria bracteata, including two new hellinoyl-type dimers, bracteatinins D1 (1) and D2 (2); a new hellinoyl-type trimer, bracteatinin T1 (3); two known monomers, nilotinin M4 (4) and 1,3-di-O-galloyl-4,6-O-(aS)-hexahydroxydiphenoyl-ß-d-glucose (5); six known dimers, tamarixinin A (6), nilotinin D8 (7), hirtellins A (10), B (9), and E (8), and isohirtellin C (11); and a known trimer, hirtellin T3 (12). The structures of the tannins were elucidated by spectroscopic data analysis and comparisons to known tannins. All compounds were evaluated as free radical scavengers using 1,1-diphenyl-2-picrylhydrazyl and hydroxy radicals and compared to the activity of BHT and Trolox. Compound 6 showed a significant anti-inflammatory effect on croton oil-induced ear edema in mice (200 mg/kg, inhibition rate 69.8%) and on collagen-induced arthritis in DBA/1 mice (20 mg/kg, inhibition rate 46.0% at day 57).
Subject(s)
Anti-Inflammatory Agents/isolation & purification , Anti-Inflammatory Agents/pharmacology , Drugs, Chinese Herbal/isolation & purification , Drugs, Chinese Herbal/pharmacology , Free Radical Scavengers/isolation & purification , Free Radical Scavengers/pharmacology , Hydrolyzable Tannins/isolation & purification , Hydrolyzable Tannins/pharmacology , Tamaricaceae/chemistry , Animals , Anti-Inflammatory Agents/chemistry , Arthritis, Experimental/chemically induced , Biphenyl Compounds/pharmacology , Drugs, Chinese Herbal/chemistry , Free Radical Scavengers/chemistry , Hydrolyzable Tannins/chemistry , Mice , Mice, Inbred DBA , Microsomes, Liver/drug effects , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Picrates/pharmacology , RatsABSTRACT
Three new saikosaponin analogs, comastomasaponins I-K (1-3), were isolated from the aerial portions of Comastomapedunculatum. The structures of these compounds were elucidated on the basis of spectroscopic data analysis, and their nitric oxide production inhibitory activity was evaluated invitro.
Subject(s)
Araliaceae/chemistry , Drugs, Chinese Herbal/isolation & purification , Oleanolic Acid/analogs & derivatives , Saponins/isolation & purification , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/pharmacology , Molecular Structure , Nitric Oxide/biosynthesis , Nuclear Magnetic Resonance, Biomolecular , Oleanolic Acid/chemistry , Oleanolic Acid/isolation & purification , Plant Components, Aerial/chemistry , Saponins/chemistryABSTRACT
Ten glucosyloxybenzyl 2-isobutylmalates and one benzyl alcohol glycoside were isolated from the dry tuber of Pleione bulbocodioides, which is a specie of Orchidaceae family and its dry tuber is one of the main sources of traditional Chinese medicine "shanci-gu", by a combination of various column chromatographic methods, including ODS, macroporous adsorbent resin, Sepheadex LH-20, and preparative HPLC. Their structures were identified on the basis of chemical evidences and spectroscopic analysis asloroglossin (1), grammatophylloside A (2), cronupapine (3), (-)-(2R, 3S)-1-(4-ß-D-glucopyranosyloxybenzyl)-4-methyl-2-isobutyltartrate (4), vandateroside II (5), grammatophylloside B (6), bis [4-(ß-D-glucopyranosyloxy) -benzyl] (S) -2-isopropylmalate (7), gymnoside I (8), militarine (9), dactylorhin A (10), gastrodin (11). Compounds 1-7 were isolated from this genus for the firt time.
Subject(s)
Drugs, Chinese Herbal/chemistry , Glucosides/chemistry , Malates/chemistry , Orchidaceae/chemistry , Drugs, Chinese Herbal/isolation & purification , Glucosides/isolation & purification , Malates/isolation & purification , Molecular Structure , Spectrometry, Mass, Electrospray IonizationABSTRACT
Eight new triterpenoid saponins, the saikosaponin homologs comastomasaponins A-H (1-8), as well as a known triterpenoid (9) and eight known saponins (10-17) were isolated from the aerial portions of Comastoma pedunculatum. The structures of these compounds were elucidated spectroscopically, and their hepatoprotective activity and cytotoxic activity were evaluated against five human tumor cell lines in vitro. Compounds 1, 5-12, 14, 15, and 17 exhibited potent hepatoprotective activity, and compound 11 displayed cytotoxic activity against HCT-8, Bel-7402, BGC-825, A549, and A2780 human tumor cell lines.
Subject(s)
Cytostatic Agents/chemistry , Gentianaceae/chemistry , Oleanolic Acid/analogs & derivatives , Protective Agents/chemistry , Saponins/chemistry , Triterpenes/chemistry , Cell Line, Tumor , Cytostatic Agents/isolation & purification , Cytostatic Agents/pharmacology , Humans , Nuclear Magnetic Resonance, Biomolecular , Oleanolic Acid/chemistry , Oleanolic Acid/isolation & purification , Oleanolic Acid/pharmacology , Protective Agents/isolation & purification , Protective Agents/pharmacology , Saponins/isolation & purification , Saponins/pharmacology , Triterpenes/isolation & purification , Triterpenes/pharmacologyABSTRACT
This study was to investigate the chemical constituents from pseudobulbs of Pleione yunnanensis, one of the source of traditional Chinese medicine "Shancigu". The chemical constituents were isolated by various chromatography methods, including silica gel, ODS, Sephadex LH-20, and semi-preparative HPLC. Fourteen compounds were isolated and identified from the EtOAc fraction of 90% ethanol extract, including five dihydrophenanthrenes, four bibenzyls, two triterpenoids, and three phenylacrylic acids. Their structures were identified on the basis of the spectral data as 4, 7-dihydroxy-2-methoxy-9,10-dihydrophenanthrene (1), 4, 7-dihydroxy-1-(p-hydroxybenzyl)-2-methoxy-9,10-dihydrophenanthrene (2), (2,3-trans)-2-(4-hydroxy-3-methoxyphenyl) -3-hydroxymethyl-10-methoxy-2,3,4,5-tetrahydro-phenanthro[2,1-b]furan-7-ol (3), pleionesin B (4), blestriarene A (5), batatasin III (6), 3, 3'-dihydroxy-2-(p-hydroxybenzyl) -5-methoxybibenzyl (7), 3', 5-dihydroxy-2-(p-hydroxybenzyl) -3-methoxybibenzyl (8), 3,3'-dihydroxy-2,6-bis(4-hydroxybenzyl) -5-methoxybibenzyl (9), triphyllol (10), pholidotin (11), (E) -p-hydroxycinnamic acid (12), (E)-ferulic acid (13), and (E)-ferulic acid hexacosyl ester (14). Compounds 5,10-14 were separated from this plant for the first time.
Subject(s)
Drugs, Chinese Herbal/chemistry , Orchidaceae/chemistry , Drugs, Chinese Herbal/isolation & purification , Molecular Structure , Spectrometry, Mass, Electrospray IonizationABSTRACT
Fourteen compoumds were isolated from the ethyl acetate portion of the 95% ethanolic extract of Pleione bulbocodioides by a combination of various chromatographic techniques including silica gel, ODS, macroporous adsorbent resin, Sephadex LH-20, and preparative HPLC, of which ten compoumds were phenanthrenes and dihydrophenanthrenes, two compoumds were bibenzyls, one was lignan and a sterol. Their structures were identified on the basis of spectroscopic data as monbarbatain A(1), 2, 7, 2'-trihy-droxy-4, 4', 7'-trimethoxy-1, 1'- biphenanthrene(2), blestriarene A(3), pleionesin B(4), shanciol H(5), 17-hydroxy-7'-(4'-hy-droxy-3 '-methoxyphenyl)- 4-methoxy-9, 10, 7', 8'-tetrahydrophenanthro[2, 3-b]furan-8'-yl methyl acetate(6), 1-p-hydroxybenzyl-4-methoxy phenanthrene-2, 7-diol(7), 1-p-hydroxybenzyl-4-met-hoxy-9, 10-dihydrophenanthrene-2, 7-diol(8), hircinol(9), coelonin( 10), gigantol(11), batatasin 11 (12), syringaresinol(13) and ergosta4, 6, 8 ( 14) , 22-tetraen-3-one (14). Compounds 1-3, 9, 13 and 14 were isolated from this genus for the first time.
Subject(s)
Orchidaceae/chemistry , Organic Chemicals/analysis , Drugs, Chinese Herbal/chemistryABSTRACT
Fifteen epi-aleuritolic acid derivatives were synthesized and evaluated for anti-HIV activity in 293 T cells and NO production inhibition activity. Of the derivatives, 1, 2, 3, 4, 11, and 13 showed relatively potent anti-HIV activity with EC50 values ranging from 5.80 to 13.30 µM. The most potent compound, 3α-2',2'-dimethylsuccinic acyl epi-aleuritolic acid (11), displayed significant anti-HIV activity with an EC50 value of 5.80 µM. Compounds 1, 3, 4, and 11 showed NO inhibition activity, with IC50 values ranging from 3.40 to 7.10 µM and compound 1 inhibited NO production with an IC50 value of 3.40 µM.
Subject(s)
Anti-HIV Agents/chemical synthesis , Anti-HIV Agents/pharmacology , Nitric Oxide/antagonists & inhibitors , Palmitic Acids/chemical synthesis , Palmitic Acids/pharmacology , Animals , Anti-HIV Agents/chemistry , Inhibitory Concentration 50 , Male , Mice , Mice, Inbred C57BL , Molecular Structure , Nitric Oxide/biosynthesis , Palmitic Acids/chemistryABSTRACT
To establish an HPLC method for determination of dactylorhin A and militarine in Cremastrae Pseudobulbus/Pleiones Pseudobulbus. The analysis was achieved on an Alltech Prevail C18 column (4. 6 mm x 250 mm, 5 microm) using a mobile phase of acetonitrile (A), water (B) gradient elution in a total run time of 35 min (0 min, 20:80; 30 min, 55:45; 35 min, 55:45) and a diode array detector was set at 224 nm. The flow rate was 0.8 mL x min(-1). The assay displayed good linearity over the concentration range of 0.257-9.95 microg (r = 0.999 8), and 0.128-10.27 microg (r = 0.999 9), respectively. The average recoveries (n = 9) were 94.70% and 102.8% for dactylorhin A and militarine, respectively. The method is accurate, quick, simple and reproducibility. It can be used for the quality control of Pleione bulbocodioides and Pleione yunnanensis.
Subject(s)
Glucosides/analysis , Orchidaceae/chemistry , Succinates/analysis , Chromatography, High Pressure LiquidABSTRACT
Two new triterpenoids taraxer-14-ene-1alpha,3beta-diol (1) and 3beta-hydroxytaraxer-14-ene-1-one (2), together with the known triterpenes taraxerol (3), betulin (4), betulinic acid (5), sumaresinolic acid (6), and 5-hydroxy-2-methoxy-1,4-naphthoquinone (7), 5,7-dihydroxy-6,8-dimethylchromone (8), alpha-monpalmitin (9), palmitic acid (10), 6beta-hydroxystigmast-4-en-3-one (11), beta-sitostero1 (12), have been isolated from the petroleum ether fraction of the ethanolic extract of Pterospermum heterophyllum. Their structures were established by spectroscopic methods including IR, MS, 1D, and 2D NMR experiments. Compounds 1-8 were evaluated against several human cancer cell lines. Compound 1 showed in vitro selective cytotoxicity against human lung cancer cell lines (A549) with an IC(50) value of 1.22 microM. Compound 7 showed significant cytotoxicity against the A549, HCT-8, Bel7402, BGC-823, and A2780 cancer cell lines with IC(50) values of 0.21, 0.55, 0.40, 0.59, and 0.34 microM, respectively. However, the other compounds were inactive (IC(50)>10 microM).
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Drugs, Chinese Herbal/isolation & purification , Malvaceae/chemistry , Triterpenes/isolation & purification , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Drug Screening Assays, Antitumor , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/pharmacology , Female , Humans , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Oleanolic Acid/analogs & derivatives , Oleanolic Acid/chemistry , Oleanolic Acid/isolation & purification , Palmitic Acid/chemistry , Pentacyclic Triterpenes , Plant Roots/chemistry , Sitosterols/chemistry , Sitosterols/isolation & purification , Stereoisomerism , Terpenes , Triterpenes/chemistry , Triterpenes/pharmacology , Betulinic AcidABSTRACT
OBJECTIVE: To study the chemical constituents from the roots of Pterospermum heterophyllum. METHOD: The chemical constituents of P. heterophyllum were isolated and purified by silica gel and sephadex LH-20 column chromatography. Their structures were identified on the basis of spectroscopic data and physicochemical properties. RESULT: Nine compounds were isolated and identified as taraxerol (1), betulin (2), betulinic acid (3), sumaresinolic acid (4), 2-methoxy-5-hydroxy-1, 4-naphthoquinone (5), 5, 7-dihydroxy-6, 8-dimethylchromone (6), alpha-monpalmitin (7), palmitic acid (8), beta-sitosterol (9). CONCLUSION: Compounds 2-7 were isolated from this genus for the first time.
Subject(s)
Malvaceae/chemistry , Plant Roots/chemistry , Chromatography , Naphthoquinones/chemistry , Oleanolic Acid/analogs & derivatives , Oleanolic Acid/chemistry , Palmitic Acid/chemistry , Pentacyclic Triterpenes , Sitosterols/chemistry , Triterpenes/chemistry , Betulinic AcidABSTRACT
Eight new triterpenoid saponins, including four ursane-type saponins, ilexchinenosides J-M (1-4), and four oleanane-type saponins, ilexchinenosides N-Q (5-8), along with three known triterpenoid saponins (9-11) were isolated from the leaves of Ilex chinensis Sims. Their structures were established by 1D, 2D NMR and MS spectroscopic analyses and through comparisons with known compounds. Moreover, compounds 1, 3, 5, 7-9 and 11 exhibited significant levels of hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell damage in in vitro assays while compound 10 had moderately inhibitory effects on the NO production of lipopolysaccharide (LPS)-induced murine macrophages.
Subject(s)
Ilex/chemistry , Plant Leaves/chemistry , Saponins/isolation & purification , Triterpenes/isolation & purification , Animals , Hep G2 Cells , Humans , Macrophages/drug effects , Mice , Molecular Structure , Nitric Oxide/metabolism , Oleanolic Acid/analogs & derivatives , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , Protective Agents/isolation & purification , Protective Agents/pharmacology , Saponins/pharmacology , Triterpenes/pharmacologyABSTRACT
Eleven previously undescribed compounds including two triterpenes, ilexchinenin A and ilexchinenin B, and nine triterpenoid saponins, ilexchinenosides A-I, along with twelve known triterpenoids were isolated from the leaves of Ilex chinensis Sims (Aquifoliaceae). Their structures were elucidated by spectroscopic analysis and comparison with known compounds. Furthermore, eight compounds exhibited significant inhibitory effects on NO production of lipopolysaccharide (LPS)-induced murine macrophages, while nine compounds exhibited potent hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell damage in in vitro assays.