ABSTRACT
Ten new cyclopentanoid monoterpenes (1-10) were isolated from the whole plant of Rehmannia piasezkii. The structures of these compounds were elucidated based on spectroscopic data analysis. In in-vitro assays, compounds 3, 7, and 9 exhibited weak hepatoprotective activities against APAP-induced HepG2 cell damage. Compound 9 exhibited protective effect on hapassocin carbon tetrachloride model.
Subject(s)
Monoterpenes , Phytochemicals , Rehmannia , Rehmannia/chemistry , Humans , Molecular Structure , Hep G2 Cells , Monoterpenes/pharmacology , Monoterpenes/isolation & purification , Phytochemicals/pharmacology , Phytochemicals/isolation & purification , Cyclopentanes/pharmacology , Cyclopentanes/isolation & purification , ChinaABSTRACT
Two new iridoid glycosides, piasezkiiosides A (1) and B (2), were isolated from aqueous extract of the whole plant of Rehmannia piasezkii. Their structures were established from the spectroscopic data, chemical transformation, and X-ray diffraction analysis. Compound 1 exhibited weak hepatoprotective activity against APAP-induced HepG2 cell damage.
ABSTRACT
Seven new pentasaccharides (1-7), rehmaglupentasaccharides A-G, were isolated from the air-dried roots of Rehmannia glutinosa. Their structures were established from the spectroscopic data obtained and by chemical evidence. The known verbascose (8) and stachyose (9) were also obtained in the current investigation, and the structure of stachyose was unequivocally defined using X-ray diffraction data. Compounds 1-9 were tested for their cytotoxicity against five human tumor cell lines, influence on dopamine receptor activation, and proliferation effects against Lactobacillus reuteri.
Subject(s)
Rehmannia , Humans , Rehmannia/chemistry , Cell Line , Plant Roots/chemistryABSTRACT
Four new iridoid glycosides (1-4), rehmaglutosides L-O, were isolated from the air-dried roots of Rehmannia glutinosa. Their structures were established from the spectroscopic data obtained and by chemical evidence. The known mellittoside (5) and ajugol (6) were also obtained in the current investigation, and the structure of mellittoside was unequivocally defined using X-ray diffraction data. Compounds 1-6 were tested for their cytotoxicity against five human tumor cell lines and proliferation effects on Lactobacillus Reuteri.
Subject(s)
Glycosides , Rehmannia , Humans , Glycosides/pharmacology , Glycosides/chemistry , Rehmannia/chemistry , Iridoid Glycosides/pharmacologyABSTRACT
As part of an ongoing project on Rehmannia species, three new pyridine alkaloides (glutinosines A - C), and one new iridoid analogue (rehmaglutin E), were isolated from the leaves of Rehmannia glutinosa. The structures of the new compounds were established by extensive spectroscopic analysis and electronic circular dichroism calculations.
Subject(s)
Alkaloids , Rehmannia , Rehmannia/chemistry , Iridoids , Molecular Structure , Plant Leaves/chemistry , Alkaloids/analysis , PyridinesABSTRACT
Four new ionones and ionone glycosides (1-4) were isolated from the whole plant of Rehmannia piasezkii Maxim. Their planar structures as well as absolute configuration were confirmed via spectroscopic analysis, ECD calculation, and X-ray crystallography. Compounds 1-4 were tested for their cytotoxicity against five human tumor cell lines and ability to inhibit LPS-activated NO production in the BV2 cell line.
Subject(s)
Rehmannia , Humans , Rehmannia/chemistry , Norisoprenoids/chemistry , Glycosides/pharmacology , Glycosides/chemistry , Molecular Structure , Cell Line, TumorABSTRACT
Twelve undescribed cyclopentanoid monoterpenes, Jiopiasins A-K and 6-epi-rehmaglutin A, and 19 known compounds were isolated from the whole plant of Rehmannia piasezkii Maxim. The structures of these compounds, especially their absolute stereochemistry, were established by extensive spectroscopic analysis, various quantum chemical calculations, and/or X-ray diffraction analyses. Furthermore, in vitro assays, some compounds exhibited moderate hepatoprotective activities against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell damage.
Subject(s)
Rehmannia , Acetaminophen , Hep G2 Cells , Humans , Molecular Structure , Monoterpenes/chemistry , Monoterpenes/pharmacology , Rehmannia/chemistryABSTRACT
The present study investigated the chemical constituents from the dry seeds of Hydnocarpus anthelminthica. The compounds were isolated and purified from the dry seeds of H. anthelminthica by various chromatographic techniques including column chromatography over silica gel and Sephadex LH-20 and reversed-phase HPLC. Their structures were identified by spectroscopic analysis. The in vitro cytotoxic activities were determined by MTT assay. Ten compounds were isolated and identified as 2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(2-hydroxy-5-methoxyphenyl)-3-oxo-1-propanol(1), threo-1,2-bis-(4-hydroxy-3-methoxyphenyl)-propane-1,3-diol(2), erythro-1,2-bis-(4-hydroxy-3-methoxyphenyl)-propane-1,3-diol(3), 2-(4-hydroxy-3-methoxyphenyl)-3-(2-hydroxy-5-methoxyphenyl)-3-oxo-1-propanol(4), 3-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-propan-1-one(5), chrysoeriol(6), evofolin B(7), apigenin-3'-methoxy-7-O-rutinoside(8), luteolin(9), and vitexin(10). Compound 1 is a new compound. Compounds 4 and 5 were isolated from this genus for the first time. All compounds showed no significant cytotoxic activity.
Subject(s)
1-Propanol , Propane , 1-Propanol/analysis , Propane/analysis , Seeds/chemistryABSTRACT
Five new fatty acids with a terminal 3-oxo-cyclopentene ring, cyclopentenone acids A-E (1-5), were isolated from the ethanol extract of the seeds of Hydnocarpus anthelminthica. The structures of these compounds were elucidated on the basis of their spectroscopic data and chemical evidence. Compounds 1-3 were evaluated for their anti-inflammatory activity based on the inhibition of NO production in microglial BV2 cells, and all of them showed weak anti-inflammatory activities.
Subject(s)
Fatty Acids , Seeds , Anti-Inflammatory Agents , Fatty Acids/analysis , Fatty Acids/pharmacology , Molecular Structure , Seeds/chemistryABSTRACT
Three new erythrina alkaloids, eryalkals A (1), B (2), and C (3), were isolated from the roots of Erythrina corallodendron L. Their structures, including their absolute configurations, were elucidated based on analyses of HR-ESI-MS, 1D/2D NMR and single-crystal X-ray diffraction techniques. The isolated erythrina alkaloids were screened for the antioxidant and cytotoxic activities. All the compounds showed no antioxidant activity and cytotoxic activities.
Subject(s)
Alkaloids , Erythrina , Antioxidants , Molecular Structure , Plant RootsABSTRACT
Ten new bisbenzylisoquinoline alkaloids (1-10) and eight known analogues (11-18) were obtained from the roots of Stephania tetrandra. The structures of these compounds were determined by spectroscopic methods, single-crystal X-ray diffraction, electronic circular dichroism analyses, and chemical method. Compounds 1, 15, and 16 showed the better anti-inflammatory activities with IC50 values of 15.26 ± 2.99, 6.12 ± 0.25, and 5.92 ± 1.89 µM, respectively. Compound 18 possessed cytotoxic activities against MCF-7, HCT-116, and HepG2 cell lines with IC50 values of 2.81 ± 0.06, 3.66 ± 0.26, and 2.85 ± 0.15 µM, respectively.
Subject(s)
Anti-Inflammatory Agents/pharmacology , Antineoplastic Agents, Phytogenic/pharmacology , Benzylisoquinolines/pharmacology , Nitric Oxide/antagonists & inhibitors , Plant Roots/chemistry , Stephania tetrandra/chemistry , Animals , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/isolation & purification , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Benzylisoquinolines/chemistry , Benzylisoquinolines/isolation & purification , Cell Line, Tumor , Cell Proliferation/drug effects , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , Humans , Lipopolysaccharides/antagonists & inhibitors , Lipopolysaccharides/pharmacology , Macrophages/drug effects , Macrophages/metabolism , Mice , Molecular Structure , Nitric Oxide/biosynthesis , Structure-Activity RelationshipABSTRACT
Five new alkaloids (1-5), including three new aporphine alkaloids and two new phenanthrene alkaloids, together with 10 known compounds (6-15) were obtained from the roots of Stephania tetrandra. Their structures were elucidated by spectroscopic methods, single-crystal X-ray diffraction, and electronic circular dichroism analyses. Compounds 7-10, and 13 showed antioxidant activities with malondialdehyde (MDA) inhibitory rates of 62.50 ± 1.91 to 98.44 ± 0.34% at the concentration of 10 µM.
Subject(s)
Alkaloids/pharmacology , Antioxidants/pharmacology , Aporphines/pharmacology , Phenanthrenes/pharmacology , Stephania tetrandra/chemistry , Alkaloids/isolation & purification , Animals , Antioxidants/isolation & purification , Aporphines/isolation & purification , China , Circular Dichroism , Lipid Peroxidation , Malondialdehyde/antagonists & inhibitors , Microsomes, Liver/drug effects , Molecular Structure , Phenanthrenes/isolation & purification , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , Plant Roots/chemistry , RatsABSTRACT
This project is to investigate chemical compositions from the roots of Erythrina corallodendron. Through the methods of silica gel,ODS,Sephadex LH-20 column chromatography and preparative HPLC,15 compounds were isolated from the 95% ethanol extract of the roots of E. corallodendron. Based on spectroscopic techniques,the structures of these compounds were identified as 10,11-dioxoerythraline( 1),erythrinine( 2),erythraline( 3),11-methoxyerythraline( 4),cristanines B( 5),erythratine( 6),erysotrine( 7),medioresinol( 8),( ±)-ficusesquilignan A( 9),( +)-pinoresinol( 10),nicotinic acid( 11),dibutyl phthalate( 12),vanillic acid( 13),3-hydroxy-1-( 4-hydroxy-3-methoxyphenyl)-1-propanone( 14),and syringic acid( 15). Compounds 8-10 are isolated from genus Erythrina for the first time and all compounds are isolated from E. corallodendron for the first time. Furthermore,this paper screened the antioxidant and cytotoxic activities of the compounds using models of liver microsomal oxidation inhibition and MTT.
Subject(s)
Erythrina/chemistry , Phytochemicals/analysis , Plant Roots/chemistry , Antioxidants/analysis , Chromatography, High Pressure Liquid , Microsomes, Liver/drug effects , Plant Extracts/analysisABSTRACT
Five new iridoids (1-5), jiohenrins A-E, together with sixteen known compounds (6-21), were isolated from the whole plants of Rehmannia henryi. The structures of these compounds were elucidated on the basis of their spectroscopic data.
Subject(s)
Iridoids/isolation & purification , Rehmannia/chemistry , Cell Line, Tumor , Humans , Iridoids/chemistry , Iridoids/pharmacology , Magnetic Resonance ImagingABSTRACT
Three new iridal-type triterpenoids (1-3) featuring a rearranged homofarnesylside chain were isolated from the rhizomes of Iris tectorum. Compounds 2 and 3 were found to be a pair of epimers. Their structures were elucidated on the basis of comprehensive spectroscopic analysis. A possible biosynthetic pathway for them was postulated. Moreover, the mixture of compounds 2 and 3 exhibited moderate neuroprotective activity against serum deprivation-induced PC12 cell death.
Subject(s)
Iris Plant/chemistry , Neuroprotective Agents/pharmacology , Triterpenes/pharmacology , Animals , China , Molecular Structure , Neuroprotective Agents/isolation & purification , PC12 Cells , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , Rats , Rhizome/chemistry , Triterpenes/isolation & purificationABSTRACT
This project is to investigate lignans from the seed of Hydnocarpus anthelminthica. Thirteen lignans were isolated from the 95% ethanol extract of the seed of H. anthelminthica, by polyamide resin, Sephadex LH-20, ODS column chromatography and preparative HPLC. Their structures were elucidated as(+)-syringaresinol(1), lirioresinol A(2),(+)-medioresinol(3),(7R,8R,8'R)-4'-guaiacylglyceryl-evofolin B(4), leptolepisol C(5),(-)-(7R,7'R,7â³R,8S,8'S,8â³S)-4',4â³-dihydroxy-3,3',3â³,5,5',5â³-hexamethoxy-7,9':7',9-diepoxy-4,8â³-oxy-8,8'-sesquineolignan-7â³,9â³-diol(6),(-)-(7R,7'R,7â³R,8S,8'S,8â³S)-4',4â³-dihydroxy-3,3',3â³,5,5'-pentamethoxy-7,9':7',9-diepoxy-4,8â³-oxy-8,8'ses-quineolignan-7â³,9â³-diol(7), ceplignan(8), hydnocarpusol(9), isohydnocarpin(10),(-)-hydnocarpin(11), hydnocarpin(12), and hydnocarpin-D(13) by spectroscopic data analysis. Compounds 1-8 were obtained from the genus Hydnocarpus for the first time.
Subject(s)
Lignans/analysis , Magnoliopsida/chemistry , Plant Extracts/analysis , Seeds/chemistry , Molecular Structure , Phytochemicals/analysisABSTRACT
Eight new iridoids (1-8) and an ionone glucoside (9), together with 31 known compounds (10-40), were isolated from the whole plants of Rehmannia henryi. The structures of these compounds were elucidated on the basis of their spectroscopic data and chemical evidence.
Subject(s)
Iridoids/chemistry , Norisoprenoids/chemistry , Rehmannia/chemistry , Molecular StructureABSTRACT
Heliosterpenoids A and B (1 and 2), two unprecedented jatrophane-derived diterpenoid esters with a novel 5/6/4/6-fused tetracyclic ring skeleton, were isolated from the whole plants of Euphorbia helioscopia. The structures of 1 and 2 were elucidated by extensive spectroscopic methods and electronic circular dichroism (ECD) analyses. The plausible biogenetic pathways of 1 and 2 were postulated. 1 and 2 were found to be potent inhibitors of P-glycoprotein (ABCB1) and 1 also exhibited cytotoxicity against MDA-MB-231 cell lines.
Subject(s)
Antineoplastic Agents, Phytogenic/chemistry , Diterpenes/chemistry , Euphorbia/chemistry , ATP Binding Cassette Transporter, Subfamily B/antagonists & inhibitors , ATP Binding Cassette Transporter, Subfamily B/genetics , ATP Binding Cassette Transporter, Subfamily B/metabolism , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Cell Line, Tumor , Cell Survival/drug effects , Cyclosporine/pharmacology , Diterpenes/isolation & purification , Diterpenes/pharmacology , Doxorubicin/pharmacology , Gene Expression , Humans , Inhibitory Concentration 50 , Molecular Structure , Plant Extracts/chemistryABSTRACT
Four new aristolochic acid derivatives aristchamic A (1), aristchamic B (2), aristochamic C (3a), aristchamic D (3b) and one new aristolactam aristolactam-CV (4), together with 10 known compounds (5-14), were isolated from the rhizomes of Aristolochia championii. Their structures were assigned by detailed analysis of MS and NMR spectroscopic data. All of the isolated compounds were evaluated for their cytotoxic activities against HCT-116, HepG2, BGC-823, NCI-H1650, and A2780 cell. Compound 1 exhibited significant cytotoxic activity against HCT-116, HepG2, BGC-823, and NCI-H1650, with IC50 values of 0.50, 7.37, 2.66, and 0.75µM, respectively.
Subject(s)
Aristolochia/chemistry , Aristolochic Acids/chemistry , Rhizome/chemistry , Aristolochic Acids/isolation & purification , Cell Line, Tumor , Humans , Magnetic Resonance Spectroscopy , Mass Spectrometry , Molecular StructureABSTRACT
Phytochemical investigation of the rhizomes of Iris tectorum resulted in the isolation and characterization of three new apocynin derivatives, apocynin-4-O-ß-D-(6'-O-syringyl)glucopyranoside (1), scrophenoside C-7-ethyl ether (2, 3), together with a new naturally occurring compound but known by synthesis, apocynin-4-O-ß-D-xylopyranoside (4), and five known ones (5-9). Their structures were elucidated on the basis of spectroscopic data interpretation.