ABSTRACT
Hyperacmotone A, a polycyclic polyprenylated acylphloroglucinol (PPAP) with an unprecedented skeleton, along with five undescribed congeners and eleven reported ones, was isolated from Hypericum acmosepalum. Hyperacmotone A possesses a unique monocyclic ring skeleton based on a cyclopent-4-ene-1,3-dione acylphloroglucinol core. Their structures were elucidated by extensive analysis of HRESIMS, NMR, biogenetic pathway, and quantum-chemical calculations. In addition, hypercohone G exhibited significant protective effects on high-glucose-injured HUVECs.
Subject(s)
Hypericum , Humans , Endothelial Cells , GlucoseABSTRACT
Melodicochinines A - D (1-4), four new monoterpene indole alkaloids (MIAs), along with 21 known ones, were isolated from the stems and twigs of Melodinus cochinchinensis. Their structures were elucidated on the basis of extensive spectroscopic analysis. A ubiquitin-rhodamine 110 assay showed that 11-methyloxytabersonine had potential inhibitory effect against ubiquitin-specific protease 7 (USP7).
Subject(s)
Apocynaceae/chemistry , Plant Extracts/chemistry , Secologanin Tryptamine Alkaloids/isolation & purification , China , Chromatography, High Pressure Liquid , Magnetic Resonance Spectroscopy , Optical Rotation , Plant Extracts/isolation & purification , Plant Stems/chemistry , Secologanin Tryptamine Alkaloids/chemistry , Spectrophotometry, InfraredABSTRACT
Acmoxanthones A-E (1-5), five new lavandulylated xanthones, were isolated from the aerial parts of Hypericum acmosepalum, together with four known xanthones. Their structures with absolute configurations were elucidated on the basis of analysis of MS, NMR and chiroptical properties. A bioassay against high glucose-induced damage on human umbilical vein endothelial cells (HUVECs) showed ananixanthone (6) and osajaxanthone (7) had potential antioxidative damage activity with EC50 values of 10.5 µg/mL and 7.6 µg/mL, respectively, while 3-hydroxy-2,4-dimethoxyxanthone (8) exhibited cytotoxic effect on the damaged cells with IC50 values of 7.1 µg/mL.
Subject(s)
Hypericum/chemistry , Xanthones/pharmacology , Antioxidants/isolation & purification , Antioxidants/pharmacology , Human Umbilical Vein Endothelial Cells/drug effects , Humans , Isoflavones , Molecular Structure , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , Plant Components, Aerial/chemistry , Xanthones/isolation & purificationABSTRACT
Uralins A - D, four undescribed polycyclic polyprenylated acylphloroglucinols (PPAPs) featuring an unprecedented fused hexacyclic architecture, a unique monocyclic tetra-seco-tetranor-b-PPAP, an oxidative b-PPAP and a rare norspiroindane-type m-PPAP, respectively, were isolated from the aerial parts of Hypericum uralum, along with ten known PPAPs. Their structures and absolute configurations were elucidated by extensive spectroscopic techniques (MS, NMR, [α]D, CD), conceivable biogenetic pathways and time-dependent density functional theory-based electronic circular dichroism (TDDFT-ECD) calculations. Biological assays showed three b-PPAPs had moderate antioxidative damage activities, while spiroindanes exhibited moderate cytotoxic effects.
Subject(s)
Hypericum , Circular Dichroism , Magnetic Resonance Spectroscopy , Molecular Structure , Phloroglucinol/pharmacologyABSTRACT
Hookerianones A - E (1-5), five new polyprenylated acylphloroglucinols (PPAPs), along with six known ones, were isolated from the aerial parts of Hypericum hookerianum. Their structures were elucidated by analyses of MS, NMR, chiroptical properties, biogenetic pathway, and/or single crystal X-ray diffraction. A ubiquitin-rhodamine 110 assay showed that furohyperforin and hypercalin C, two representative PPAPs in this plant, inhibited more than 90% USP7 at the concentration of 10 µM.
Subject(s)
Hypericum/chemistry , Phloroglucinol/pharmacology , Protease Inhibitors/pharmacology , Ubiquitin-Specific Peptidase 7/antagonists & inhibitors , China , Molecular Structure , Phloroglucinol/isolation & purification , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , Plant Components, Aerial/chemistry , Protease Inhibitors/isolation & purificationABSTRACT
Alopecines A-E (1-5), five unusual matrine-type alkaloids featuring with an additional dichlorocyclopropane (1-3) or a di/tri-chloromethyl (4/5) attached on the D ring, were isolated from the seeds of Sophora alopecuroides. Their structures and absolute configurations were elucidated by extensive spectroscopic techniques, and X-ray diffraction analyses or time-dependent density functional theory-based electronic circular dichroism (TDDFT-ECD) calculations. Alkaloid 4 exhibited potent inhibitory effects on the proliferation of ConA-induced T lymphocytes or LPS-induced B cells with IC50 value of 3.98 or 3.74 µM, respectively.
Subject(s)
Alkaloids/pharmacology , Immunosuppressive Agents/pharmacology , Plant Extracts/pharmacology , Sophora/chemistry , Alkaloids/chemistry , Alkaloids/isolation & purification , Animals , B-Lymphocytes/drug effects , Cell Proliferation/drug effects , Cell Survival/drug effects , Cells, Cultured , Concanavalin A/antagonists & inhibitors , Concanavalin A/pharmacology , Dose-Response Relationship, Drug , Female , Immunosuppressive Agents/chemistry , Immunosuppressive Agents/isolation & purification , Lipopolysaccharides/antagonists & inhibitors , Lipopolysaccharides/pharmacology , Mice , Mice, Inbred BALB C , Molecular Conformation , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Seeds/chemistry , Stereoisomerism , Structure-Activity Relationship , T-Lymphocytes/drug effectsABSTRACT
A phytochemical investigation on the twigs and leaves of Flueggea virosa (Euphorbiaceae) led to the isolation of flueggenoids A - E (1-5), five new 13-methyl-ent-podocarpanes, together with eleven known compounds (6-16). Their structures and absolute configurations were elucidated on the basis of extensive MS and NMR data analysis, and/or single-crystal X-ray diffraction, time-dependent density functional theory (TDDFT)-based electronic circular dichroism (ECD) calculations, and chemical transformation. All isolates were evaluated for anti-HCV activity, the results showed that terpenoids of F. virosa had nonnegligible contribution for the anti-HCV activity.
