ABSTRACT
Four unknown meroterpenoids named as psidials D-G (1-4) together with 5 known compounds (5-9) had been obtained from the leaves of Psidium guajava. Their absolute structures were elucidated by spectral and calculated methods. Psidials DF (1-3) represented unknown carbon skeleton of the 3,5-diformylbenzyl phloroglucinol-coupled sesquiterpenoid. The possible biosynthetic pathway for 1-3 was postulated. In the bioactivity assay, psidial F (3) was found to possess anti-inflammatory and anticoagulant activities.
Subject(s)
Psidium , Anti-Inflammatory Agents/pharmacology , Anticoagulants/pharmacology , Molecular Structure , Plant Extracts/analysis , Plant Leaves/chemistry , Psidium/chemistry , SkeletonABSTRACT
In our screening program for new biologically active secondary metabolites, nine new polycyclic polyprenyled acylphloroglucinols, hyperscabins D-L, together with three known compounds, were obtained from the aerial parts of Hypericum scabrum. The chemical structures of 1-9 were characterized by extensive spectroscopic analyses, nuclear magnetic resonance calculation with DP4+ probability analysis, and the electronic circular dichroism spectra were calculated. Compound 1 was an unusual prenylated acylphloroglucinol decorated with a 5-oxaspiro [4,5] deca-1,9-dione skeleton. Compound 2 was a newly identified spirocyclic polyprenylated acylphloroglucinol possessing a rare 5,5-spiroketal segment. Compounds 3, 8, and 10 (10 µM) exhibited pronounced hepatoprotective activity against d-galactosamine-induced WB-F344 cell damage in vitro assays. All test compounds (1, 3, and 7-12) demonstrated potential inhibitory effects at 10 µM against noradrenalinet ([3H]-NE) reuptake in rat brain synaptosome.
Subject(s)
Antidepressive Agents/pharmacology , Hemiterpenes/pharmacology , Hypericum/chemistry , Phloroglucinol/analogs & derivatives , Phloroglucinol/pharmacology , Protective Agents/pharmacology , Animals , Antidepressive Agents/chemical synthesis , Antidepressive Agents/isolation & purification , Cell Line , Hemiterpenes/chemical synthesis , Hemiterpenes/isolation & purification , Neurotransmitter Uptake Inhibitors/chemical synthesis , Neurotransmitter Uptake Inhibitors/isolation & purification , Neurotransmitter Uptake Inhibitors/pharmacology , Norepinephrine/metabolism , Phloroglucinol/isolation & purification , Plant Components, Aerial/chemistry , Protective Agents/chemical synthesis , Protective Agents/isolation & purification , Rats , Synaptosomes/drug effects , Synaptosomes/metabolismABSTRACT
Seven flavonoid dimers, biflavocochins A-G, together with six known compounds were isolated from the red resins of Dracaena cochinchinensis (Chinese dragon's blood). Their structures were elucidated based on extensive spectroscopic analysis. The absolute configurations of 1-7 was assigned by experimental and quantum chemical calculated ECD spectra, and that of 4 was further established by X-ray diffraction analysis using Cu Kα radiation. Compounds 1-3 are novel dimers of homoisoflavonoid and dihydrochalcone with a unique dibenzopyran ring. Compounds 2, 6, 7 exhibited moderate PTP1B inhibitory activities in an enzyme assay. Compound 1 showed neuroprotective effect on serum deficiency-induced cellular damage in PC12 cells.
Subject(s)
Dracaena/chemistry , Enzyme Inhibitors/pharmacology , Flavonoids/pharmacology , Neuroprotective Agents/pharmacology , Plant Extracts/pharmacology , Protein Tyrosine Phosphatase, Non-Receptor Type 1/antagonists & inhibitors , Animals , Crystallography, X-Ray , Dimerization , Enzyme Inhibitors/chemistry , Flavonoids/chemistry , Humans , Models, Molecular , Neuroprotective Agents/chemistry , PC12 Cells , Plant Extracts/chemistry , Protein Tyrosine Phosphatase, Non-Receptor Type 1/metabolism , RatsABSTRACT
Three pairs of new germacranolides, (+)/(-)-chlogermacrones A-C, along with two known analogues were obtained from the roots of Chloranthus henryi. Spectroscopic techniques and single-crystal X-ray crystallographic analyses were used for the structure elucidation of the compounds. All of the isolated compounds were tested for their neuroprotective effects on H2O2 damaged PC12 cells, compounds 3 and 5 increased cell viability from 43.4 ± 1.3% to 99.6 ± 8.7 and 68.1 ± 4.8% at 10 µM, respectively.
Subject(s)
Magnoliopsida/chemistry , Neuroprotective Agents/pharmacology , Plant Roots/chemistry , Animals , Cell Survival/drug effects , Models, Molecular , Molecular Structure , Neuroprotective Agents/chemistry , PC12 Cells , RatsABSTRACT
Eight undescribed 9,19-cycloartane type triterpenoid glycosides (cimdalglnoside A-H) and ten known analogues were obtained from the phytochemical research on the roots of Actaea dahurica (syn. Cimicifuga dahurica). All compounds were characterised by spectroscopic experiments, and chemical method. All the compounds isolated were assayed for cytotoxicity to five human cancer cell lines. Cimdalglnoside G showed promising cytotoxicities against Hela, and MCF-7 cell lines with IC50 values at 7.7 and 12.2⯵M.
Subject(s)
Actaea/chemistry , Glycosides/pharmacology , Plant Roots/chemistry , Triterpenes/pharmacology , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , China , Glycosides/isolation & purification , HeLa Cells , Humans , MCF-7 Cells , Molecular Structure , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , Triterpenes/isolation & purificationABSTRACT
Six new and one known dihydroagarofuran sesquiterpenoids esterified with organic acids were obtained from the leaves of Tripterygium wilfordii. Spectroscopic techniques (UV, IR, MS, NMR, ORD and CD) were used for the structure elucidation of the compounds. The structures of compounds 1 and 2 were confirmed by X-ray single crystallographic analyses. The inhibitory effects on NO production in LPS-induced macrophages of 1-7 were conducted. At 10⯵mol/L, compounds 1, 2 and 7 showed moderate inhibitory effects on NO production in LPS-induced macrophages with inhibitory rate at 31.2⯱â¯3.6, 40.9⯱â¯4.3, and 66.79⯱â¯3.1%, respectively.
Subject(s)
Macrophages/drug effects , Sesquiterpenes/pharmacology , Tripterygium/chemistry , Animals , Mice , Molecular Structure , Nitric Oxide/metabolism , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , Plant Leaves/chemistry , RAW 264.7 Cells , Sesquiterpenes/isolation & purificationABSTRACT
Eight new meroterpenoids with different types of monoterpene units, namely, magmenthanes A-H (1-8), were identified from the bark of Magnolia officinalis var. biloba. Magmenthane A (1) possesses a 1,3-dioxabicyclo [4.3.01,5] nonane skeleton, 1-5 possess five pairs of enantiomers and 6 possesses a 1,1'-diallyl-biphenyl fragment. The structures of 1-8 were elucidated on the basis of 1D and 2D NMR, HRESIMS and electronic circular dichroism (ECD) calculations. Compounds 5 and 8 displayed significant PTP1B inhibitory activities with IC50 values of 4.38 and 3.88⯵M, respectively.
Subject(s)
Enzyme Inhibitors/pharmacology , Magnolia/chemistry , Neuroprotective Agents/pharmacology , Plant Bark/chemistry , Plant Extracts/pharmacology , Protein Tyrosine Phosphatase, Non-Receptor Type 1/antagonists & inhibitors , Terpenes/pharmacology , Cell Line, Tumor , Cell Survival/drug effects , Dose-Response Relationship, Drug , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/isolation & purification , Glutamic Acid/pharmacology , Humans , Molecular Structure , Neuroprotective Agents/chemistry , Neuroprotective Agents/isolation & purification , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Protein Tyrosine Phosphatase, Non-Receptor Type 1/metabolism , Structure-Activity Relationship , Terpenes/chemistry , Terpenes/isolation & purificationABSTRACT
Three 18(4â3)-abeo-abietanoids, a new natural product and two new compounds, named tripordolides Aâ»C (1â»3), were isolated from the leaves of Tripterygium wilfordii. Their structures were elucidated on the basis of their spectroscopic analysis, and the absolute configuration of compounds was confirmed by CD and X-ray crystallographic analysis using anomalous scattering of Cu Kα radiation. Compounds 1 and 3 showed moderate inhibitory activities against NO production in lipopolysaccharide-induced (LPS) RAW 264.7 macrophages in vitro.
Subject(s)
Abietanes/pharmacology , Macrophages/drug effects , Nitric Oxide/analysis , Plant Extracts/pharmacology , Plant Leaves/chemistry , Tripterygium/chemistry , Animals , Cells, Cultured , Lipopolysaccharides/pharmacology , Macrophages/cytology , Macrophages/metabolism , Mice , Nitric Oxide/metabolismABSTRACT
Magterpenoid A (1), possessing a rare 4,6,11-trioxatricyclo[5.3.1.01,5]undecane framework with an irregular monoterpenoid moiety, magterpenoid B (2), with an unprecedented 6/6/6/6 polycyclic skeleton, and magterpenoid C (3), a novel terpenoid quinone with a C6-C3 unit, were isolated from the bark of Magnolia officinalis var. biloba. Plausible biogenetic pathways of 1-3 are presented. Compounds 1 and 3 exhibited significant PTP1B inhibitory activities with IC50 values of 1.44 and 0.81 µM, respectively.
Subject(s)
Magnolia , Molecular Structure , Plant Bark , Plant ExtractsABSTRACT
Four new nerolidol-type sesquiterpene glucosides, triptergosidols A-D (1-4) were isolated from the leaves of Tripterygium wilfordii. Three aglycones, named triptergerols A (1a), B (2a), and C (3a), were acquired by enzymatic hydrolysis of 1-3. The structures of nerolidol-type sesquiterpenes were elucidated on base of kinds of spectroscopic analysis, and their absolute configurations were determined by CD method. In addition, compounds 1-4 were tested for cytotoxicity against two cell lines and inhibitory effects against NO production in RAW264.7 macrophage.
Subject(s)
Glucosides/isolation & purification , Plant Leaves/chemistry , Sesquiterpenes/isolation & purification , Tripterygium/chemistry , Animals , Cell Line, Tumor , Glucosides/pharmacology , Humans , Mice , Molecular Structure , Nitric Oxide/metabolism , RAW 264.7 Cells , Sesquiterpenes/pharmacologyABSTRACT
Two new saponins, notoginsenosides Ng1 (1) and Ng2 (2), together with seven known compounds (3-9), were isolated from the leaves of Panax notoginseng. Their structures were elucidated by UV, IR, HRESIMS, and NMR experiments. Compounds 6 and 7 showed moderate cytotoxic activities against HCT-116, with IC50 values of 4.98 and 0.64 µmol/L, respectively.
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Drugs, Chinese Herbal/isolation & purification , Panax notoginseng/chemistry , Saponins/isolation & purification , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Drug Screening Assays, Antitumor , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/pharmacology , HCT116 Cells , Humans , Inhibitory Concentration 50 , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Plant Leaves/chemistry , Saponins/chemistry , Saponins/pharmacologyABSTRACT
In view of the significant neuroprotective effect of Clausena lansium, we continued to separate the n-butanol and the water extracts from the stems of C. lansium in order to find the leading compounds with significant activity. Two new phenolic glycosides, Clausenolside A-B (1-2), one new pair of phenolic enantiomers (3a, 3b), and two new monoterpenoids, clausenapene A-B (4-5), together with twelve known analogues (6-17) were isolated from the stems of C. lansium. Compounds 1-17 were obtained from C. lansium for the first time. Compounds 3a, 3b, 4, 16, and 17 showed strong or moderate potential neuroprotective effects on inhibited PC12 cell injury induced by okadaic acid, and compound 9 exhibited strong potential hepatoprotective activities. Their structures were elucidated on the basis of spectroscopic analyses, including UV, IR, NMR experiments, and electronic circular dichroism (ECD) spectra.
Subject(s)
Clausena/chemistry , Drugs, Chinese Herbal/chemistry , Plant Stems/chemistry , Animals , Cell Survival/drug effects , Drug Discovery , Glycosides/isolation & purification , Glycosides/pharmacology , Hep G2 Cells , Humans , Hydrolysis , Monoterpenes/isolation & purification , Monoterpenes/pharmacology , Neuroprotective Agents/isolation & purification , Neuroprotective Agents/pharmacology , PC12 Cells , Phenols/isolation & purification , Phenols/pharmacology , Rats , StereoisomerismABSTRACT
Three new lupane-type triterpenoids (1-3), three new oleane-type triterpenoids (4-6), as well as two known compounds (7-8) were isolated from Euonymus carnosus. The structures of the compounds were elucidated on the basis of spectroscopic data analyses, including UV, IR, MS, and NMR experiments. The inhibitory on LPS-induced NO production in microglia BV2 cells of compounds 1-8 were also evaluated. Compounds 1 and 2 showed moderate abilities to inhibit NO production, with IC50 values of 5.99 and 8.47µM, respectively.
Subject(s)
Anti-Inflammatory Agents/chemistry , Microglia/drug effects , Pentacyclic Triterpenes/chemistry , Plant Stems/chemistry , Animals , Anti-Inflammatory Agents/isolation & purification , Cell Line , Mice , Molecular Structure , Nitric Oxide/metabolism , Pentacyclic Triterpenes/isolation & purificationABSTRACT
Three new lignanosides (+)-(8S,7'S,8'S)-burselignan-9'-O-ß-d-glucopyrano side (1), (+)-(8R,7'S,8'R)-isolariciresinol-9'-O-ß-d-fucopyranoside (2), (-)-(8S, 7'R,8'R)-methoxyisoariciresinol-9'-O-α-l-rhamnoside (3), along with four known compounds, were isolated from the aerial parts of Lespedeza cuneata (Dum.Cours.) G.Don. The fucopyranoside has not been reported in this genus previously. Their structures and absolute configurations were elucidated on the basis of comprehensive spectroscopic analyses (UV, IR, HR-ESI-MS, 1D and 2D NMR, CD), as well as by comparison with known analogues in the literature. Compounds 2 and 6 showed moderate hepatoprotective activities.
Subject(s)
Drugs, Chinese Herbal/isolation & purification , Glycosides/isolation & purification , Lespedeza/chemistry , Lignans/isolation & purification , Plant Components, Aerial/chemistry , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/pharmacology , Glycosides/pharmacology , Lignans/chemistry , Lignans/pharmacology , Liver/drug effects , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , StereoisomerismABSTRACT
Two new limonoids, clauemargines M-N (1-2), together with five known compounds (3-7), were isolated from the stems of Clausena emarginata, and compounds 6 and 7 were gained from this plant for the first time. Their structures were established and elucidated on the basis of comprehensive spectroscopic analysis. The absolute configurations of 1-2 were further determined by the octant rule of saturated cyclic ketone. Compounds 1, 2, 4, and 5 showed moderate neuroprotective effects against L-glutamic acid-induced cellular damage in human neuroblastoma SK-N-SH cells at 10 µM.
Subject(s)
Clausena/chemistry , Drugs, Chinese Herbal/isolation & purification , Limonins/isolation & purification , Plant Stems/chemistry , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/pharmacology , Glutamic Acid/pharmacology , Humans , Limonins/chemistry , Limonins/pharmacology , Molecular Structure , Neuroblastoma/chemically induced , Neuroprotective Agents/pharmacologyABSTRACT
Four phenylpropanoid glucosides (1-4) and five lignan glycosides (5-9) were isolated from the aerial parts of Lespedeza cuneata, together with three known lignan glycosides (10-12). Their structures were elucidated on the basis of spectroscopic analyses, and the absolute configurations of compounds 5-9 were determined from the CD spectra. In addition, the compounds were tested for their ability to activate the transcription effect on xbp1 promoter. Compounds 4, 5, 7, 9, 10, and 12 could activate the transcription of xbp1 to varying degrees, with EC50 values ranging from 0.18 to 0.64 µM.
Subject(s)
Drugs, Chinese Herbal/isolation & purification , Glycosides/isolation & purification , Lespedeza/chemistry , Lignans/isolation & purification , Phenylpropionates/isolation & purification , Circular Dichroism , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/pharmacology , Glycosides/chemistry , Glycosides/pharmacology , Lignans/chemistry , Lignans/pharmacology , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Phenylpropionates/chemistry , Phenylpropionates/pharmacology , Plant Components, Aerial/chemistryABSTRACT
Ten compounds were isolated from Mylabris phalerata by using preparative HPLC and column chromatography over MCI gel. On the basis of physical-chemical properties, NMR and MS data analysis, the compounds were identified as 5'-[(1 R,2 R,3 S,6R)-1-hydroxymethyl-2-methyl-3,6-epoxycyclohexane-1,2-dicarboximide]- ethyl-2'-methyl-2'-butenoate (1),cantharidin (2), cyclo-(L-Pro-L-Ala) (3), cyclo-(R-Pro-R-Leu) (4), cyclo-(S-Pro-R-Leu) (5), cyclo-(D-Pro-L-Tyr) (6), indole-3-aldehyde (7), 3-indoleacetic acid (8), valerolactam (9), and 4-hydroxyphthalid (10).Compound 1 was a new compound, and compounds 2-10 were obtained from this genus for the first time. Compounds 1-9 were subjected to cytotoxic activity on HCT-116, HepG2, BGC-823, NCI-H1650, A2780 cell lines, and only compound 2 showed inhibitory effect on all cancer cell lines.
Subject(s)
Antineoplastic Agents/chemistry , Coleoptera/chemistry , Animals , Antineoplastic Agents/pharmacology , Cell Line, Tumor , Cell Survival/drug effects , Chromatography, High Pressure Liquid , Humans , Magnetic Resonance Spectroscopy , Molecular StructureABSTRACT
Two new carbazole alkaloids, claulansine S (1) and claulansine T (2), and one new amide alkaloid, clauamide A (3), together with four known analogues (4-7) were isolated from the stems of Clausena lansium. Their structures were elucidated on the basis of spectroscopic analyses, including UV, IR, and NMR experiments (HSQC, HMBC, and NOE experiments). Compounds 4 and 6 showed moderate hepatoprotective activities.
Subject(s)
Alkaloids/isolation & purification , Amides/isolation & purification , Carbazoles/isolation & purification , Clausena/chemistry , Drugs, Chinese Herbal/isolation & purification , Alkaloids/chemistry , Alkaloids/pharmacology , Amides/chemistry , Amides/pharmacology , Carbazoles/chemistry , Carbazoles/pharmacology , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/pharmacology , Liver/drug effects , Liver/metabolism , Liver/pathology , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Plant Stems/chemistry , Protective Agents/pharmacologyABSTRACT
Four new norsesquiterpenes wilfordonols A-D (1-4), along with three known compounds, sarmentol B (5), boscialin (6), and (+)-loliolide (7), were isolated from the leaves of Tripterygium wilfordii Hook.f.. The structures of the new compounds were elucidated on the basis of their spectroscopic analysis, and the absolute configuration of the compounds was confirmed by CD and modified Mosher's method. At a concentration of 10 µM, compounds 4, 6, and 7 inhibited signal transducer and activator of transcription 1 translocation by 34.27 ± 1.02%, 48.93 ± 1.76%, and 70.31 ± 2.20%, respectively.
Subject(s)
Drugs, Chinese Herbal/isolation & purification , Sesquiterpenes/isolation & purification , Tripterygium/chemistry , Benzofurans/chemistry , Benzofurans/isolation & purification , Cyclohexanols/chemistry , Cyclohexanols/isolation & purification , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/pharmacology , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Plant Leaves/chemistry , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacologyABSTRACT
Seven new carbazole alkaloids, clauemarazoles A-G, together with 19 known analogues were isolated from the stems of Clausena emarginata. Their structures were established on the basis of spectroscopic analyses, and the absolute configurations of compounds 1a, 1b, 5a, and 5b were confirmed by their ECD spectroscopy. Compounds 4, 13, 15, and 17 exhibited inhibitory abilities on LPS-induced NO production. Compounds 10-12, 20, 22, and 24 displayed hepatoprotective effects against DL-galactosamine-induced damage in WB-F344 cells.