ABSTRACT
The present study aimed to explore the chemical constituents from the stems and leaves of Cephalotaxus fortunei. Seven lignans were isolated from the 75% ethanol extract of C. fortunei by various chromatographic methods, including silica gel, ODS column chromatography, and HPLC. The structures of the isolated compounds were elucidated according to physicochemical properties and spectral data. Compound 1 is a new lignan named cephalignan A. The known compounds were identified as 8-hydroxy-conidendrine(2), isolariciresinol(3), leptolepisol D(4), diarctigenin(5), dihydrodehydrodiconiferyl alcohol 9'-O-β-D-glucopyranoside(6), and dihydrodehydrodiconiferyl alcohol 4-O-β-D-glucopyranoside(7). Compounds 2 and 5 were isolated from the Cephalotaxus plant for the first time.
Subject(s)
Cephalotaxus , Lignans/analysis , Plant Leaves/chemistry , Ethanol , Chromatography, High Pressure LiquidABSTRACT
Six new tirucallane-type triterpenoids (1-6), along with ten known triterpenoids, were isolated from methylene chloride extract of the resin of Boswellia carterii Birdw. By the application of the comprehensive spectroscopic data, the structures of the compounds were clarified. The experimental electronic circular dichroism spectra were compared with those calculated, which allowed to assign the absolute configurations. Compounds 5 and 6 possesed a 2, 3-seco tirucallane-type triterpenoid skeleton, which were first reported. Their inhibitory activity against NO formation in LPS-activated BV-2 cells were evaluated. Compound 9 showed appreciable inhibitory effect, with an IC
ABSTRACT
<b>Objective::To study the chemical constituents of pericarps of <italic>Zanthoxylum bungeanum</italic>. <b>Method::The dried pericarps of <italic>Z</italic>. <italic>bungeanum</italic> were smashed, and then extracted and concentrated in 95%ethanol to obtain the total extract. The total extract was loaded on a silica gel CC, eluted with different polar solvents in sequence, and then concentrated to obtain corresponding parts. The methylene chloride fraction and the <italic>n</italic>-butanol fraction were separated and purified by silica gel column chromatography, Sephadex LH-20 gel column chromatography, ODS column chromatography, semi-preparative HPLC, etc. And their structures were identified based on physicochemical properties and various spectroscopic methods. <b>Result::Fourteen compounds were isolated from the dichloromethane fraction and the n-butanol fraction of the <italic>Z</italic>. <italic>bungeanum</italic> and identified as(1<italic>S</italic>, 3<italic>S</italic>)-1-methyl-1, 2, 3, 4-tetrahydro-<italic>β</italic>-carboline-3-carboxylic acid(<bold>1</bold>), (3<italic>S</italic>)-1, 2, 3, 4-tetrahydro-<italic>β</italic>-carboline-3-carboxylic acid(<bold>2</bold>), apigenin-7, 4′-dimethyl ether(<bold>3</bold>), genkwanin(<bold>4</bold>), lcariside F<sub>2</sub>(<bold>5</bold>), breyniaionoside A(<bold>6</bold>), 3-methoxyphenethyl alcohol-4-<italic>O</italic>-<italic>β</italic>-<italic>D</italic>-glucopynanoside(<bold>7</bold>), 1-<italic>O</italic>-<italic>β</italic>-<italic>D</italic>-glucopyranosyloxy-3-methoxy-5-hydroxybenzene(<bold>8</bold>), orcinol-<italic>O</italic>-<italic>β</italic>-<italic>D</italic>-glucopyranoside(<bold>9</bold>), syringin(<bold>10</bold>), 4-[(3<italic>S</italic>)-3-hydroxybutyl]-2-methoxyphenyl-<italic>β</italic>-<italic>D</italic>-glucopyranoside(<bold>11</bold>), (+ )-lyoniresinol-3a-<italic>O</italic>-<italic>β</italic>-<italic>D</italic>-glucopyranoside(<bold>12</bold>), 2-methylpropanyl-6-<italic>O</italic>-<italic>β</italic>-<italic>D</italic>-apiofuranosyl-<italic>β</italic>-<italic>D</italic>-glucopyranoside(<bold>13</bold>)and(<italic>E</italic>)-6-hydroxy-2, 6-dimethylocta-2, 7-dienoic acid(<bold>14</bold>). <b>Conclusion::All compounds were isolated from <italic>Z</italic>. <italic>bungeanum</italic> for the first time, and compounds <bold>1-4, 12</bold> and <bold>14</bold> were isolated from this genus for the first time.
ABSTRACT
A new steroid with a long cross-conjugation structure, 15a-hydroxy-(22E, 24R)-ergosta-3, 5, 8 (14), 22-tetraen-7-one (1), was isolated from the marine-derived fungus Aspergillus aculeatus. Its structure was established by the extensive spectroscopic analyses, and its cytotoxicities against P388, HL-60, and PC-3 cell lines were measured in vitro.
Subject(s)
Animals , Humans , Aspergillus , Chemistry , Cell Line, Tumor , Cholestenones , Chemistry , Pharmacology , HL-60 Cells , Inhibitory Concentration 50 , Molecular Structure , Seawater , MicrobiologyABSTRACT
To study the secondary metabolites of a marine-derived fungus Ascotricha sp. ZJ-M-5, several chromatographic methods including macroporous resin, silica gel, ODS and Sephadex LH-20 were used to isolate the compounds, and their structures were elucidated on the basis of physicochemical properties and spectroscopic methods. Ten compounds were obtained and identified as ascotrichic acid B (1), (3R)-6-hydroxymellein (2), beta-carboline (3), (22E, 24R)-ergosta-7, 22-diene-3beta, 5alpha, 6beta-triol (4), (22E, 24R)-ergosta-7, 22-diene-3beta, 5alpha, 6beta, 9alpha-tetraol (5), cyclo (Leu-Pro) (6), cyclo (Ile-Leu) (7), cyclo (Pro-Val) (8), cyclo (Pro-Gly) (9), and cyclo (Hpro-Ala) (10). Among them, compound 1 is a new 3, 4-seco-lanostane triterpenoid which has been isolated from the filamentous fungi for the first time, and compounds 2-10 are firstly isolated from Ascotricha genus.
Subject(s)
Humans , Antineoplastic Agents , Chemistry , Pharmacology , Ascomycota , Chemistry , Carbolines , Chemistry , Pharmacology , Cell Line, Tumor , Cell Proliferation , Dipeptides , Chemistry , Pharmacology , Drug Screening Assays, Antitumor , Lanosterol , Chemistry , Pharmacology , Molecular Structure , Peptides, Cyclic , Chemistry , PharmacologyABSTRACT
Natural aryltetralin lactone lignans existed in the plants of family Berberidaceae, Acanthaceae, Burseraceae, Verbenaceae, Euphorbiaceae, etc. Due to the antineoplastic and antiviral properties, it has become a hot research topic in medicinal chemistry. This review covers extraction and isolation, biosynthesis, plant origin, and structure and spectral characteristics of natural aryltetralin lactone lignans. It will provide a useful reference for the intensive studies and rational utilization of aryltetralin lactone lignans.
Subject(s)
Lactones , Chemistry , Lignans , Chemistry , Magnetic Resonance Spectroscopy , Spectrophotometry, Ultraviolet , Tetrahydronaphthalenes , ChemistryABSTRACT
AIM@#To study the metabolites of a halotolerant fungus Alternaria sp. M6.@*METHODS@#The metabolites were isolated and purified by various chromatographic techniques. Their structures were determined on the basis of physical properties and spectroscopic data.@*RESULTS@#Nine compounds were isolated and identified as 8β-chloro-3, 6aα, 7β, 9β, 10-pentahydroxy-9, 8, 7, 6a-tetrahydroperylen-4(6aH)-one (1), alterperylenol (2), dihydroalterperylenol (3), adenine (4), adenosine (5), deoxyadenosine (6), guanosine (7), tryptophan (8), and hexadecanoic acid (9).@*CONCLUSION@#Compound 1 is a new perylenequinone.
Subject(s)
Alternaria , Chemistry , Metabolism , Biological Products , Chemistry , Molecular Structure , Perylene , Chemistry , Quinones , Chemistry , Salt ToleranceABSTRACT
In the structural determination of natural glycosides, nuclear magnetic resonance (NMR) is an important approach in determining the configuration of glycoside bond. The test of coupling constant of the anomeric proton and chemical shift of the anomeric carbon are two common methods, but these methods are not suitable for some sugars. For those sugars, detailed 13C NMR analysis is an alternative choice. This paper summarizes the characteristics of 1H and 13C NMR data of the common monosaccharides published in the literatures, in order to search an approach to determine the configuration of glycoside bond.
Subject(s)
Carbohydrate Conformation , Carbon Isotopes , Glycosides , Chemistry , Magnetic Resonance Spectroscopy , Methods , Monosaccharides , ChemistryABSTRACT
To study the xanthones from the leaves of Calophyllum inophyllum Linn., several chromatography methods were employed to isolate the constituents. Investigation on the CHCl3 extract led to the isolation of a new xanthone named inophyxanthone A (1) and four known compounds, which were pancixanthone A (2), gerontoxanthone B (3), jacareubin (4) and pyranojacareubin (5). Among them, compound 2 was obtained from this plant firstly, and compound 3 was obtained for the first time from this genus. The structure of inophyxanthone A (1) was identified as 1, 3, 5-trihydroxy-2-(1, 1-dimethylallyl)xanthone by spectral analysis.
Subject(s)
Calophyllum , Chemistry , Molecular Structure , Plant Leaves , Chemistry , Plants, Medicinal , Chemistry , Xanthones , ChemistryABSTRACT
<p><b>OBJECTIVE</b>To study the chemical constituents and antitumor activities of Euonymus alatus.</p><p><b>METHOD</b>Compounds were isolated and purified repeatedly by silica gel, Sephadex LH-20 column chromatography, and their chemical structures were elucidated by their physicochemical properties and spectral data, such as 1H-NMR, 13C-NMR and EI-MS. The trypan blue experiments in vitro were used to observe the antitumor activity of several compounds.</p><p><b>RESULT</b>Ten compounds were obtained and identified as (+)-usnic acid (1), benzoic acid (2), 2-hydroxy-4-methoxy-3, 6-dimethyl benzoic acid (3), lupeol (4), 3 beta-hydroxy-30-norlupan-20-one (5), (2R, 3R)-3, 5, 7, 4'-tetrahydroxy flavanone (6), kaempferol (7), 5, 7, 4'-trihydroxy flavanone (8), quercetin (9) and daucosterol (10).</p><p><b>CONCLUSION</b>Compounds 1, 2, 5 and 8 were isolated from this genus for the first time. The trypan blue experiments in vitro showed that compounds 1, 4 and 5 had growth inhibitory effects on HL-60 cells.</p>
Subject(s)
Humans , Antineoplastic Agents , Pharmacology , Cell Proliferation , Drugs, Chinese Herbal , Pharmacology , Euonymus , Chemistry , HL-60 CellsABSTRACT
<p><b>OBJECTIVE</b>To study the chemical constituents of the barks of Garcinia tetralata.</p><p><b>METHOD</b>Compounds were isolated and purified repeatedly by silica gel and ODS column chromatography and their chemical structures were elucidated by their physicochemical properties and spectral data analysis.</p><p><b>RESULT</b>Ten compounds were obtained and identified as 1, 7-dihydroxyxanthone (1), buchanaxanthone (2), garciniaxanthone H (3), 1, 2, 5-trihydroxyxanthone (4), subelliptenone H (5), 6-desoxyjacareubin (6), 6-deoxyisojacreubin (7), subelliptenone G (8), methyl orsellinate (9) and beta-sitosterol (10).</p><p><b>CONCLUSION</b>Compounds 1-10 were isolated from this plant and compound 9 was obtained from the genus Garcinia for the first time.</p>
Subject(s)
Drugs, Chinese Herbal , Chemistry , Garcinia , Chemistry , Magnetic Resonance Spectroscopy , Plant Bark , Chemistry , Resorcinols , Chemistry , Sitosterols , Chemistry , Spectrometry, Mass, Electrospray Ionization , Xanthones , ChemistryABSTRACT
<p><b>OBJECTIVE</b>To study the constituents of the leaves of Heliciopsis lobata.</p><p><b>METHOD</b>Compounds were isolated by column chromatography on silica gel, neutral aluminum oxide and Sephadex LH -20, and their structures were identified by spectroscopic and physicochemical data.</p><p><b>RESULT</b>Seven known compounds were isolated and identified as: myricetin (1), myricitrin (2), syringetin-3-O-beta-D-glucopyranoside (3), medioresinol (4), D-1-O-methyl-myo-inositol (5), hydroquinone (6), and beta-sitosterol (7).</p><p><b>CONCLUSION</b>All of these compounds were isolated from genus Heliciopsis for the first time.</p>
Subject(s)
Flavonoids , Chemistry , Hydroquinones , Chemistry , Magnetic Resonance Spectroscopy , Plant Leaves , Chemistry , Proteaceae , Chemistry , Sitosterols , ChemistryABSTRACT
<p><b>OBJECTIVE</b>To study the chemical constituents of Dregea sinensis var. corrugata.</p><p><b>METHOD</b>The chemical constituents were isolated by various column chromatographic techniques. Structures were elucidated on the basis of NMR data.</p><p><b>RESULT</b>Eight compounds were isolated and their structures were elucidated as syringaresinol (1), syringaresinol-O-3-D-glycopyranoside (2), 3, 4'-dimethoxyl-4, 9, 9'-trihydroxyl-benzofuranneolignan-7'-ene (3), 3, 4'-di- methoxyl-4, 9-dihydroxyl-9'-hydroethyl-benzofuranneolignan-7'-ene (4), conifer-aldehyde (5), sinapic aldehyde (6), 3-hydoxy-1-(4-hydroxy-3-methoxy-phenyl)-propan-1-one (7), 3-hydroxy-1-(3-methoxy-4-hydroxyphenyl)-propan-1-one (8).</p><p><b>CONCLUSION</b>Compounds 1-8 were isolated from Dregea sinensis var. corrugata for the first time.</p>
Subject(s)
Apocynaceae , Chemistry , Drugs, Chinese Herbal , Chemistry , Plants, Medicinal , Chemistry , Propane , ChemistryABSTRACT
To study the C21 steroids of the stems of Marsdenia tenacissima (Roxb.) Wight et Arn, various chromatography methods were used for the isolation of the constituents and their structures were identified by spectral analysis. Eight C21 steroids were isolated from the CHCl3 extract, which were identified as 11alpha-O-tigloyl-17beta-tenacigenin B (1), 17beta-tenacigenin B (2), tenacigenoside A (3), 11alpha-O-2-methylbutyryl-12beta-O-acetyl tenacigenin B (4), tenacissoside H (5), marsdenoside A (6), tenacissoside G (7), and tenacissoside I (8). Among them, compound 1 is a new compound.
Subject(s)
Marsdenia , Chemistry , Molecular Structure , Plant Stems , Chemistry , Plants, Medicinal , Chemistry , Saponins , Chemistry , Steroids , ChemistryABSTRACT
<p><b>OBJECTIVE</b>To study the chemical constituents from the stems and leaves of Calophyllum inophyllum.</p><p><b>METHOD</b>The compounds were isolated by column chromatography on silica gel, Sephadex LH-20 and preparative TLC. Their structures were elucidated by chemical methods and NMR, MS spectroscopic data.</p><p><b>RESULT</b>Nine compounds were identified as 2-hydroxyxanthone (1), 4-hydroxyxanthone (2), 1, 5-dihydroxyxanthone (3), 1, 7-dihydroxyxanthone (4), 1, 3, 5-trihydroxy-2-methoxyxanthone (5), 6-deoxyjacareubin (6), amentoflavone (7), kaempferol-3-O-alpha-L-rhamnoside (8) and quercetin-3-O-alpha-L-rhamnoside (9).</p><p><b>CONCLUSION</b>Compounds 8 and 9 were isolated from the genus Calophyllum and compounds 1, 2, 4-6 were isolated from this plant for the first time.</p>
Subject(s)
Calophyllum , Chemistry , Chromatography , Methods , Flavonoids , Chemistry , Glycosides , Chemistry , Kaempferols , Chemistry , Magnetic Resonance Spectroscopy , Methods , Mass Spectrometry , Methods , Plant Leaves , Chemistry , Plant Stems , Chemistry , Plants, Medicinal , Chemistry , Pyrans , Chemistry , Quercetin , Chemistry , Xanthenes , ChemistryABSTRACT
<p><b>AIM</b>To isolate triterpene saponins of polygalacic acid type from the roots of Platycodon grandiflorum (Jacq.) A. DC and to identify their structures.</p><p><b>METHODS</b>The compounds were separated by means of extraction, chromatography on silica gel, MPLC and HPLC, and their structures were elucidated on the basis of spectral analyses (FAB-MS, IR, 1H NMR, 13C NMR etc.).</p><p><b>RESULTS</b>Three triterpene saponins were isolated from the roots of Platycodon grandiflorum. They were identified as 3-O-beta-D-laminaribiosyl polygalacic acid (I), 3-O-beta-D-glucopyranosyl polygalacic acid (II), polygalacin D (III), separately.</p><p><b>CONCLUSION</b>Compound I is a new compound, compounds II, III are known triterpene saponins. The compound I and II were isolated from the plant for the first time, which is also the monodesmoside from the plant for the first time.</p>
Subject(s)
Molecular Conformation , Molecular Structure , Plant Roots , Chemistry , Plants, Medicinal , Chemistry , Platycodon , Chemistry , Saponins , ChemistryABSTRACT
<p><b>OBJECTIVE</b>To study the metabolites of marine fungus Alternalia sp.</p><p><b>METHOD</b>Compounds were separated by column chromatography and their structures were elucidated by means of chemical and spectral analysis.</p><p><b>RESULT</b>Six compounds were isolated from the ethyl acetate and n-butanol extracts of the fermentation of marine fungus Alternalia sp. Their structures were elucidated as p-benzyloxy-phenol ( I ), p-hydroxy phenyl ethylamine( II ), 3-hydroxymethyl-8-hydroxyl-pyrrolopiperazine-2, 5-dione ( III ), 3-isobutyl-6-secbutyl-piperazine-2, 5-dione (IV), 5alpha, 8alpha-epidioxy-ergosta-6, 22-diene-3beta-ol (V), 3beta-hydroxxy-cholesta-5-ene (VI).</p><p><b>CONCLUSION</b>Compounds I , II, III, IV have the activity of inducing morphological deformation of mycelia germinated from conidia of Pyricularia oryzae. Compounds I , II , III were isolated from the genus Alternalia for the first time.</p>