Three new dihydrophenanthrenes, retusiusine D (1), retusiusine E (2), retusiusine F (3), and a new phenanthrene retusiusine G (4), together with two known dihydrophenanthrenes 4,7-dihydroxy-2,3-methylenedioxy-9,10-dihydrophenanthrene (5) and epemeranthol-A (6) were isolated from the tubers of Bulbophyllum retusiusculum. Their structures were established on the basis of extensive spectroscopic analyses. Compounds 1 and 2 exhibited potent cytotoxic activities against SMMC-7721 and weak cytotoxic activities against HL-60. Compound 4 showed moderate cytotoxic activity against SMMC-7721 and MCF-7.
Antineoplastic Agents, Phytogenic/pharmacology , Orchidaceae/chemistry , Phenanthrenes/pharmacology , Antineoplastic Agents, Phytogenic/isolation & purification , Cell Line, Tumor , Humans , Molecular Structure , Phenanthrenes/isolation & purification , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , Plant Tubers/chemistry
Two new phenylpropanoids, retusiusines A (1) and B (2), and a pair of new phenylpropyl enantiomers, (±)-retusiusine C (3a and 3b), together with eight known compounds, dihydroconiferyl dihydro-p-coumarate (4), methyl 3-(4-hydroxyphenyl) propionate (5), 3-(4-hydroxyphenyl)-propanoic acid (6), dihydroferulic acid (7), methyl 3-(4-methoxyphenyl) propionate (8), 3-(3,4-dimethoxyphenyl)-2-propenal (9), trans-p-coumaric acid (10) and dihydroconiferyl alcohol (11), were isolated from the tubers of Bulbophyllum retusiusculum. The absolute configurations of the new compounds were determined by calculating their electronic circular dichroism (ECD), spectra and specific optical rotations and comparing the calculated values with the experimental data. Compound 2 exhibited potent antifungal activity against Candida albicans (16 µg/mL). Compound 3 showed moderate antibacterial activity against Bacillus subtilis (64 µg/mL).
Anti-Bacterial Agents/isolation & purification , Antifungal Agents/isolation & purification , Orchidaceae/chemistry , Phenylpropionates/isolation & purification , Plant Tubers/chemistry , Anti-Bacterial Agents/pharmacology , Antifungal Agents/pharmacology , Bacillus subtilis/drug effects , Candida albicans/drug effects , Escherichia coli/drug effects , Microbial Sensitivity Tests , Molecular Structure , Phenylpropionates/pharmacology , Plants, Medicinal , Stereoisomerism
A new phenylpropanoid glucoside tuberosinine D (1) and a chain compound (Z)-11R,12S,13S-trihydroxy-9-octadecenoate (2) were isolated from the roots of Allium tuberosum. The absolute configuration of 1 was established by comparing of experimental and calculated electronic circular dichroism. The absolute configuration of 2 was determined using the modiï¬ed Mosher's method for the first time.
Allium/chemistry , Glucosides/chemistry , Plant Roots/chemistry , Anti-Bacterial Agents/pharmacology , Antifungal Agents/pharmacology , Bacillus subtilis/drug effects , Candida albicans/drug effects , Circular Dichroism , Escherichia coli/drug effects , Glucosides/pharmacology , Microbial Sensitivity Tests , Molecular Conformation , Spectrometry, Mass, Electrospray Ionization , Spectrophotometry, Infrared
A new flavone C-glycoside, apigenin 6-C-α-arabinofuranosyl 8-C-α-arabinopyranoside (1) and a new bibenzyl, bulbotetusine (2), were isolated from the tubers of Bulbophyllum retusiusculum. Their structures were established on the basis of extensive spectroscopic analyses. The absolute configuration of 2 was determined by the comparison of experimental and calculated electronic circular dichroism. Compounds 1 and 2 showed no obvious cytotoxic activity against any five human tumour cell lines with IC50 values >40 µM.
Apigenin/isolation & purification , Bibenzyls/isolation & purification , Glycosides/isolation & purification , Orchidaceae/chemistry , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Apigenin/chemistry , Apigenin/pharmacology , Bibenzyls/chemistry , Cell Line, Tumor , Drug Screening Assays, Antitumor , Glycosides/chemistry , Glycosides/pharmacology , Humans , Molecular Conformation , Plant Extracts/chemistry , Plant Tubers/chemistry , Spectrometry, Mass, Electrospray Ionization
Nineteen alkaloids, including a new C19-diterpenoid alkaloid stapfianine A (1) and a new benzamide derivative stapfianine B (2) were isolated from the roots of Aconitum stapfianum. Their structures were established on the basis of extensive spectroscopic analyses (IR, HRESIMS, 1D and 2D NMR).
An unusual proaporphine alkaloid bearing an isopropanenitrile group at isoquinoline nitrogen, named epiganine A (1) and a new aporphine alkaloid, epiganine B (2), together with eight known alkaloids, pronuciferine (3), dehydrodicentrine (4), romerine (5), romeline (6), N-methylcalycinine (7), phanostenine (8), dicentrine (9), and N-methyllaurotetanine (10), were isolated from the roots of Stephania epigaea. The absolute configuration of 1 was determined by calculating electronic circular dichroism (ECD) and comparing with experimental data. Compounds 2 and 4 showed strong acetylcholinesterase (AChE) inhibitory effects with the IC50 values of 4.36 and 2.98µM, respectively. Compounds 5-9 also exhibited potent AChE inhibitory activities.
Aporphines/chemistry , Cholinesterase Inhibitors/chemistry , Plant Roots/chemistry , Stephania/chemistry , Aporphines/isolation & purification , Cholinesterase Inhibitors/isolation & purification , Inhibitory Concentration 50 , Molecular Structure
Diterpenoid alkaloids, named vilmorines A-D, in addition to fifteen known alkaloids, were isolated from roots of Aconitum vilmorinianum. Their structures were established on the basis of extensive spectroscopic analyses. Antibacterial and antioxidant studies on isolated compounds were also carried out.
Aconitum/chemistry , Alkaloids/isolation & purification , Anti-Bacterial Agents/isolation & purification , Antioxidants/isolation & purification , Diterpenes/isolation & purification , Drugs, Chinese Herbal/isolation & purification , Iron Chelating Agents/isolation & purification , Alkaloids/chemistry , Alkaloids/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Antioxidants/chemistry , Antioxidants/pharmacology , Diterpenes/chemistry , Diterpenes/pharmacology , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/pharmacology , Iron Chelating Agents/chemistry , Iron Chelating Agents/pharmacology , Microbial Sensitivity Tests , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Plant Roots/chemistry
Three new spirostanol saponins named tuberosines A-C (1-3), together with three known ones tuberoside O (4), 25(S)-Schidigera-saponin D5 (5), and shatavarin IV (6) were isolated from the roots of Allium tuberosum. Their structures were established on the basis of extensive spectroscopic analyses. Whereas compounds 5 and 6 exhibited potent antibacterial activities against Bacillus subtilis (32 µg/mL) and Escherichia coli (16 µg/mL), the new saponin 2 showed only moderate antibacterial activities against these pathogens. The relationship between the antibacterial activities and the structures of these saponins are described.
Allium/chemistry , Anti-Bacterial Agents/chemistry , Plant Roots/chemistry , Spirostans/chemistry , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/pharmacology , Bacillus subtilis/drug effects , Escherichia coli/drug effects , Microbial Sensitivity Tests , Molecular Conformation , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Plant Extracts/pharmacology , Spirostans/isolation & purification , Spirostans/pharmacology
The total phenolic content of 31 species of fern plants was determined, and their antioxidant activities were assessed by DPPH radical scavenging analysis.
Antioxidants/pharmacology , Ferns/chemistry , Free Radical Scavengers/pharmacology , Phenols/analysis , Plant Extracts/pharmacology , Biphenyl Compounds , Hydrazines , Phenols/pharmacology , Picrates