ABSTRACT
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
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
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 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
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 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 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 study the chemical constituents from the husk of Xanthoceras sorbifolia Bunge. Repeated column chromatography on silica gel and preparative TLC were used to isolate the compounds whose structures were elucidated based on spectroscopic data (ESIMS, EIMS, 1D and 2D NMR).</p><p><b>RESULTS</b>A new alkaloid was isolated and identified as: 2-methyl-6-(2', 3', 4'-trihydroxybutyl)-pyrazine (I), along with nine known compounds: cleomiscosin D (II), naringenin (III), eriodictyol (IV), kaempferol (V), quercetin (VI), rutin (VII), 5,7-dihydroxychromone (VIII), tyrosol (IX), 1-O-methyl-myo-inositol (X).</p><p><b>CONCLUSION</b>Compound I is a new alkaloid, compounds II, IV, V, VII - X were isolated from this genus for the first time.</p>
Subject(s)
Alkaloids , Chemistry , Magnetic Resonance Spectroscopy , Sapindaceae , ChemistryABSTRACT
<p><b>AIM</b>To study the chemical constituents of Sphaerophysa salsula (Pall.) DC.</p><p><b>METHODS</b>Compounds were isolated by repeated chromatography, on silica gel and Sephadex LH-20 columns and identified by spectroscopic data (ESI-MS, 1H and 13C NMR, HSQC, HMBC).</p><p><b>RESULTS</b>Eight compounds have been isolated and identified as: isorhamnetin-3-O-[6"-(3-hydroxy-3-methylglutaroyl)-beta-D-glucopyranoside] (I), quercitrin (II), n-butyl-O-beta-D-fructopyranoside (III), nicotinic acid (IV), succinic acid (V), erythrol (VI), D-mannitol (VII), uridine (VIII).</p><p><b>CONCLUSION</b>Compound I is a new compound. Compounds I -VI were isolated from this genus for the first time.</p>