ABSTRACT
Chemical constituents of ethyl acetate extract of Illicium burmanicum were isolated and purified by various chromatographic methods,including Silica gel, Sephadex LH-20, C18 reverse-phased silica gel, Preparative TLC and Preparative HPLC. Their structures were identified by spectral analysis including NMR and MS data. Fourteen compounds were separated from I. burmanicum and their structures were identified as 7S,8R-erythro-4,7,9,9'-tetrahydroxy-3,3'-dimethoxy-8-O-4'-neolignan (1), 7R,8R-threo-4,7, 9,9'-tetrahydroxy-3,3 '-dimethoxy-8-O-4'-neolignan(2) ,polystachyol(3), (-) -massoniresinol(4), angustanoic acid F (5), trans-sobrerol(6), (3S,6R) -6,7-dihydroxy-6,7-dihydrolinalool (7), (3S, 6S) -6,7-dihydroxy-6,7-dihydrolinalool (8), 2,6-dimethoxy-4-allyl-phenol (9), 3,5-dihydroxy4-hydroxy benzaldehyde (10), 3-hydroxy4-methoxybenzaldehyde (11), methyl vanillate (12), shikimic acid ethylester (13) and beta-sitosrerol (14). Except compound 14, the rest thirteen compounds were separated from this plant for the first time.
Subject(s)
Drugs, Chinese Herbal/chemistry , Illicium/chemistry , Drugs, Chinese Herbal/isolation & purification , Molecular Structure , Spectrometry, Mass, Electrospray IonizationABSTRACT
OBJECTIVE: To investigate the anti-HIV constituents from the root of Mirabilis jalapa. METHOD: The compounds were isolated by column chromatography on silica gel, Sephadex LH - 20, MCI-gel CHP-20P and RP-18. The structure were identified by means of NMR and MS analyses (1H-NMR, 13C-NMR, MS). RESULT: Eleven compounds were isolated and identified as astragaloside II (1), astragaloside II (2), astragaloside IV (3), astragaloside VI (4), flazin (5), 4'-hydroxy-2, 3-dihydroflavone 7-beta-D-glucopyranoside (6), gingerglycolipid A (7), 3, 4-dihydroxybenzaldehyd (8), p-hydroxybenzaldehyde (9), beta-sitosterol (10) and daucosterol (11). CONCLUSION: Compounds 1-9 were obtained from this genus for the first time.
Subject(s)
Mirabilis/chemistry , Plant Roots/chemistry , Benzaldehydes/analysis , Benzaldehydes/chemistry , Carbolines/analysis , Carbolines/chemistry , Chromatography, Gel , Furans/analysis , Furans/chemistry , Galactolipids/analysis , Galactolipids/chemistry , Magnetic Resonance Spectroscopy , Mass Spectrometry , Sitosterols/analysis , Sitosterols/chemistryABSTRACT
A phytochemical study of the ethanolic extract of Stachyurus imalaicus var. himalaicus was undertaken and as a result a new polyoxygenated steroid, named stachsterol ((20S)-20, 25-dihydroxy-4-cholesten-3-one, 1) and three known ecdysteroids, 20-hydroxyecdysone (2), 20-hydroxyecdysone-20, 22-monoacetonide (3) and polypodine B-20,22-monoacetonide (4), were isolated. Their structures were elucidated by spectroscopic methods, including UV, NMR, MS and HR-MS. The purified product 1 was found to have in vitro cytotoxic activity against human Hela cell lines with an IC50 value of 2.5 microg/mL. This is the first time that phytoecdysteroids have been found in the genus Stachyurus.
Subject(s)
Magnoliopsida/chemistry , Phytosterols/isolation & purification , Cell Death/drug effects , HeLa Cells , Humans , Mass Spectrometry , Phytosterols/chemistry , Phytosterols/pharmacologyABSTRACT
Three new eudesmane-type sesquiterpenoids, compounds 1-3, and eight known constituents, including mucrolidin (4), 1beta,4beta,7alpha-trihydroxyeudesmane (5), 1beta,4beta,6beta,11-tetrahydroxyeudesmane (6), oplodiol (7), bullatantriol (8), acetylbullatantriol (9), homalomenol (10), and maristeminol (11), were isolated from the aerial parts of Homalomena occulta. Their structures were determined by interpretation of spectroscopic and mass-spectrometric data, and their antimicrobial activities toward six different bacterial strains were tested. Most of the compounds showed weak antibacterial activities in an agar-diffusion assay.
Subject(s)
Anti-Bacterial Agents/pharmacology , Araceae/chemistry , Sesquiterpenes/pharmacology , Anti-Bacterial Agents/isolation & purification , Benzimidazoles/isolation & purification , Benzimidazoles/pharmacology , China , Cyclopentanes/isolation & purification , Cyclopentanes/pharmacology , Naphthols/isolation & purification , Naphthols/pharmacology , Sesquiterpenes/isolation & purificationABSTRACT
Two new alpha-tetralone (=3,4-dihydronaphthalen-1(2H)-one) derivatives, berchemiaside A and B (1 and 2, resp.), and one new flavonoid, quercetin-3-O-(2-acetyl-alpha-L-arabinofuranoside (3), together with ten known flavonoids compounds, eriodictyol (4), aromadendrin (5), trans-dihydroquercetin (6), cis-dihydroquercetin (7), kaempferol (8), kaempferol-3-O-alpha-L-arabinofuranoside (9), quercetin (10), quercetin-3-O-alpha-L-arabinofuranoside or avicularin (11), quercetin 3'-methyl ether, 3-O-alpha-L-arabinofuranoside (12), and maesopsin (13), were isolated from the bark of Berchemia floribunda. Their structures were determined by various NMR techniques and chemical studies. Compounds 3-13 were tested for their cytotoxic activity against human leukemia cells. Among them, kaempferol (8) and maesopsin (13) showed significant inhibitory activities against human leukemia cells CCRF-CEM and its multidrug-resistant sub-line, CEM/ADR5000, with IC(50) values of 14.0, 5.3, 10.2, and 12.3 microM, respectively.
Subject(s)
Rhamnaceae/chemistry , Tetralones/chemistry , Tetralones/toxicity , Cell Line, Tumor , Cell Proliferation/drug effects , Humans , Inhibitory Concentration 50 , Magnetic Resonance Spectroscopy , Molecular Structure , Plant Bark/chemistryABSTRACT
One novel neolignan (tetracentronsine; 1), one new indole alkaloid (=3-(2-hydroxyethyl)-1H-indole-5-O-beta-D-glucopyranoside; 2), and two new phenol derivatives, 3-{2-[(beta-glucopyranosyl)oxy]-4,5-(methylenedioxy)phenyl}propanoic acid (3) and methyl 3-{2-[(beta-glucopyranosyl)oxy]-4,5-(methylenedioxy)phenyl}propanoate (4), together with six known compounds were isolated from the stem bark of Tetracentron sinense. Their structures were determined by spectral analysis, including 1D- and 2D-NMR, and MS analyses. These compounds were tested for their cytotoxic activity against human leukaemia cells in vitro. Among them, compound 2, (E)-3-(4-hydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide (5), and maslinic acid (6) showed significant inhibitory activities against human leukaemia cells CCRF-CEM and its multidrug-resistant sub-line, CEM/ADR5000, with IC50 values in a range of 7.1 to 29.7 microM.
Subject(s)
Antineoplastic Agents, Phytogenic , Glycosides , Magnoliopsida/chemistry , Plants, Medicinal , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Cell Line, Tumor , Cell Proliferation/drug effects , Cell Survival/drug effects , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , Glycosides/chemistry , Glycosides/isolation & purification , Glycosides/pharmacology , Humans , Molecular Structure , Plant Bark/chemistry , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Plant Extracts/pharmacology , Structure-Activity RelationshipABSTRACT
A new bieremophilanolide was isolated from the roots and rhizomes of Ligularia lapathifolia. Its structure was established as 8,8'-bi-3beta-angeloyloxy-eremophil-7(11)-en-12,8alpha(14beta,6alpha)-diolide (1) by IR, MS, 1D, and 2D NMR experiments.
Subject(s)
Asteraceae/chemistry , Lactones/isolation & purification , Plant Extracts/isolation & purification , Sesquiterpenes/isolation & purification , China , Lactones/chemistry , Mass Spectrometry , Molecular Conformation , Nuclear Magnetic Resonance, Biomolecular , Optical Rotation , Plant Extracts/chemistry , Plant Roots/chemistry , Rhizome/chemistry , Sesquiterpenes/chemistry , Spectrophotometry, InfraredABSTRACT
In an attempt to explore the biogenetic relationship of furanoeremophilane derivatives and eremophilan-8alpha,12-olides, produced in Ligularia and their structure-activity relationship, we studied the photosensitized oxidation of furanoeremophilane-type sesquiterpenes. Under the condition of several solvents solution Irradiation with a 200 W incandescent lamp of furanoeremophilan-14beta,6alpha-olide isolated from Ligularia vellerea, in various solutions with methylene blue, rose bengal, toluidine blue and safranine T gave several products. The products were isolated by chromatographic procedure and their structures were elucidated as eremophilan-14beta,6alpha,8alpha,12-diolide derivatives by NMR, IR and MS methods. A reaction mechanism has been proposed.
Subject(s)
Asteraceae/chemistry , Sesquiterpenes/chemical synthesis , Animals , Hepatocytes/drug effects , Light , Magnetic Resonance Spectroscopy , Mice , Molecular Structure , Oxidation-Reduction , Plant Roots/chemistry , Sesquiterpenes/metabolism , Sesquiterpenes/pharmacology , Sesquiterpenes/radiation effects , Singlet OxygenABSTRACT
A new pinoresinol-type Lignan, 9alpha-angloyloxypinoresinol (1), was isolated from the roots and rhizomes of Ligularia kanaitizensis (Franch.) Hand.-Mazz, in addition to a known compound, 9alpha-hydroxypinoresinol (2). The structure of this new lignan (1) was established on the basis of 1D and 2D NMR experiments. Anti-HIV-1 RT biological assay showed that 1 was inhibitory to HIV-1 RT.
Subject(s)
Asteraceae/chemistry , Furans/isolation & purification , Lignans/isolation & purification , Furans/chemistry , Furans/pharmacology , HIV Reverse Transcriptase/antagonists & inhibitors , Lignans/chemistry , Lignans/pharmacology , Magnetic Resonance SpectroscopyABSTRACT
Seven new eremophilanolides were isolated from the roots and rhizomes of Ligularia lapathifolia. Their structures were established as 3beta-angeloyloxy-8beta H-eremophil-7(11)-ene-12,8alpha (14beta, 6alpha)-diolide, 3beta-angeloyloxy-8beta-hydroxyeremophil-7(11)-ene-12,8alpha(14beta,6alpha)-diolide,3beta-angeloyloxy-8beta-methoxyeremophil- 7(11)-ene-12,8alpha(14beta,6alpha)-diolide,3beta-angeloyloxy-8beta-ethoxyeremophil-7(11)-ene-12, 8alpha (14beta,6alpha)-diolide, 3beta-angeloyloxy-10beta- hydroxyeremophil-8(9),7(11)-diene-12,8(14beta,6alpha)-diolide, 3beta-angeloyloxy-8,12-expoy-12alpha-hydroxy-8beta-methoxyeremophil-7(11)-en-14beta,6alpha-olide and 3beta-angeloyloxyeremophilan-7,11-dien-14beta,6alpha-olide, by means of spectroscopic analyses. Moreover, application of a photooxygenation reaction on 7 resulted in the generation of 2 with an alpha,beta-unsaturated gamma-lactone moiety. This biomimetic transformation supports a biogenetic pathway proposed for 2.
Subject(s)
Asteraceae , Phytotherapy , Plant Extracts/chemistry , Sesquiterpenes/chemistry , Humans , Oxidation-Reduction , Plant Roots , RhizomeABSTRACT
Two new norsesquiterpenes were isolated from the extracts of the roots and rhizomes of Ligularia lapathifolia (Franch.) Hand.-Mazz. Their structures were identified as 2-acetyl-3a-methyl-5-(2-methyl-but-2-enoyloxy)-3a,4,5,6,7,7a-hexahydro-H-indene-4-carboxylic acid (1) and 2-acetyl-8a-methyl-2-(2-methyl-but-2-enoyloxy)-6-oxo-1,2,3,4,4a,5,6,8a-octahydro-naphthalene-1-carboxylic acid (2), respectively, on the basis of spectral data and for 1 by single-crystal X-ray analysis.
Subject(s)
Asteraceae/chemistry , Naphthalenes/chemistry , Naphthalenes/isolation & purification , Crystallography, X-Ray , Plant Extracts/chemistry , Plant Roots/chemistry , Spectrum AnalysisABSTRACT
From the roots and rhizomes of Sinodielsia yunnanensis, three new sesquiterpenes were isolated and their structures were established as 5alpha,6beta- H-1(10),3,7(11)-guaiatrien-12,6alpha-olide ( 1), 5alpha,6beta,7beta- H-1(10),3-guaiadien-12,6alpha-olide ( 2) and 5beta-hydroxy-10alpha- O-angeloyl-3-oxodauc-8-ene ( 3) by means of spectroscopic analyses and single-crystal X-ray experiment (for compound 1).
Subject(s)
Apiaceae , Phytotherapy , Plant Extracts/chemistry , Sesquiterpenes, Guaiane/chemistry , Crystallography, X-Ray , Humans , Magnetic Resonance Spectroscopy , Plant Roots , RhizomeABSTRACT
OBJECTIVE: To investigate the anti-HIV constituents from the root of Polygonatum kingianum. METHOD: The compounds were isolated by column chromatography on silica gel, Sephadex LH-20, MCI-gel CHP-20P and their structures were determined on the basis of their spectroscopic evidence including IR, MS and NMR data. RESULT: 13 compounds were isolated, of which nine compounds were identified as liquiritigenin, isoliquiritigenin, 4', 7-dihydroxy-3'-methoxyisoflavone, (6aR, 11aR)-10-hydroxy-3, 9-dimethoxypterocarpan, 5-hydroxymethyl-2-furancarboxaldehyde, salicylic acid, n-butyl-beta-D-fructopyranoside, n-butyl-beta-D-fructofuranoside, n-butyl-alpha-D-fructofuranoside. CONCLUSION: Compounds 1-6 were obtained from this plant for the first time.
Subject(s)
Chalcone/analogs & derivatives , Chalcone/isolation & purification , Flavonoids/isolation & purification , Plants, Medicinal/chemistry , Polygonatum/chemistry , Chalcone/chemistry , Chalcones , Flavanones , Flavonoids/chemistry , Plant Roots/chemistry , Salicylic Acid/chemistry , Salicylic Acid/isolation & purificationABSTRACT
A new indolizinone, namely kinganone (1) together with 3-ethoxymethyl-5,6,7,8-tetrahydro-8-indolizinone (2) and isomucronulatol (3) were isolated from the rhizome of Polygonatum kingianum. Their structures were elucidated mainly on the basis of spectral data. Indolizinones 1 and 2 showed weak antibacterial and antifungal activities when compared to rifampicin and amphotericin, respectively, in the agar diffusion assay.
