Activity Against N-acetyl-p-aminophenol Research Articles

New triterpenoid saponins from the leaves of Ilex chinensis and their hepatoprotective activity.

Seven new triterpenoid saponins, including five ursane-type saponins, ilexchinenosides R-V (1-5), and two oleanane-type saponins, ilexchinenosides W-X (6-7), with four known triterpenoid saponins (8-11) were isolated from the leaves of Ilex chinensis. Their structures were elucidated by comprehensive spectroscopic 1D and 2D NMR and HR-ESI-MS data. Their sugar moieties were determined by HPLC analysis compared with standards after hydrolysis and derivatization. Compounds 1, 2, 4, 9 and 10 exhibited potential hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell injury in vitro.

Hepatoprotective Glucosyloxybenzyl 2-Hydroxy-2-isobutylsuccinates from Pleione yunnanensis.

Nine new glucosyloxybenzyl 2-hydroxy-2-isobutylsuccinates, pleionosides M-U (1-9), and 12 known compounds (10-21) were isolated from the pseudobulbs of Pleione yunnanensis. Their structures and absolute configurations were established through a combination of HRESIMS and NMR data and supported by physical and chemical methods. Compounds 5, 6, 10, and 15 showed significant in vitro hepatoprotective activity against d-galactosamine (d-GalN)-induced toxicity in HL-7702 cells with increasing cell viability by 27%, 22%, 19%, and 31% compared to the model group (cf. bicyclol, 14%) at 10 μM, respectively. Compounds 4, 9, and 11 exhibited moderate hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced toxicity in HepG2 cells with increasing cell viability by 9%, 16%, and 12% compared to the model group (cf. bicyclol, 9%) at 10 μM, respectively.

Two new phenylpropanoid glycosidic compounds from the pseudobulbs of Pleione bulbocodioides and their hepatoprotective activity

Two new phenylpropanoid glycosidic compounds (a pair of epimers), named pleionosides K (1) and L (2), were isolated from the pseudobulbs of Pleione bulbocodioides (Franch.) Rolfe. Their structures, including absolute configurations, were elucidated by a combination of MS, NMR data, chemical methods and the comparison of experimental and calculated electronic circular dichroism (ECD). Their possible biosynthetic pathway was discussed in the text. Furthermore, the two compounds exhibited moderate hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell damage in in vitro assays, with cell survival rates of 25.83% and 28.82% at 10 μM, respectively, and antioxidant effect against H2O2-induced toxicity in human SK-N-SH cell, with increasing viability at 10 μM of 24.9% and 34.6%, respectively.

New phenolic constituents obtained from Polygonum multiflorum

ObjectiveTo isolate the phenolic compounds obtained from the dried roots of Polygonum multiflorum and investigate their pharmacological activities. MethodsThe chemical constituents were isolated and purified by combining them with a macroporous resin (DM-8), MCI gel, and Sephadex LH-20 and by performing ODS column chromatography. Their structures were elucidated by 1D and 2D NMR analyses, as well as mass spectrometry. The isolated compounds were evaluated to determine their hepatoprotective and α-glucosidase inhibitory activities in vitro. ResultsTwo phenolic compounds, namely, polygonimitin E (1) and polygonimitin F (2), were isolated from the dried roots of P. multiflorum. Compound 2 (10 µmol/L) only showed moderate hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell damage. Unfortunately, these two compounds exhibited no α-glucosidase inhibitory activity. ConclusionCompounds 1 and 2 were new compounds. Compound 2 could be one of the potential hepatoprotective constituents of P. multiflorum.

Hepatoprotective lignans and triterpenoids from the roots of Kadsura longipedunculata

Two new tetrahydrobenzocyclooctabenzofuranone lignans (1–2), a new dibenzocyclooctadiene lignan (3) and three new schiartane-type triterpenoids (4–6), together with six known compounds (7–12), were isolated from the roots of Kadsura longipedunculata. Their structures were elucidated by extensive NMR and HRESIMS spectroscopic data analysis. The absolute configurations of these compounds were determined by comparison of the experimental and calculated ECD spectra. Compound 12 exhibited moderate hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced toxicity in HepG2 cells with cell survival rates of 53.04%.

Two azafluoranthene alkaloids and a phytoecdysone from the stems of Cyclea barbata

Two new azafluoranthene alkaloids (1 and 2), and a new phytoecdysone (3), were isolated from the stems of Cyclea barbata Miers, together with six known compounds (4–9). Their structures were elucidated by spectroscopic data analysis and comparison with published data. This is the first report of azafluoranthene alkaloids (1 and 2) and phytoecdysones (3, 8, and 9) from Cyclea genus. In in vitro bioassay, four isolates (3, 5, 6, and 9) showed moderate hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced toxicity in HepG2 cells.

Hepatoprotective activity of glucosyloxybenzyl succinate derivatives from the pseudobulbs of Pleione bulbocodioides

Ten previously undescribed glucosyloxybenzyl succinate derivatives, pleionosides A-J, and fifteen known compounds were isolated from the pseudobulbs of Pleione bulbocodioides (Franch.) Rolfe. Their structures were elucidated by a combination of MS and NMR data, physical and chemical methods and a comparison with known compounds. Furthermore, three compounds exhibited potent hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell damage in in vitro assays, with cell survival rates of 31.89%, 31.52% and 31.97% at 10 μM. Four compounds exhibited moderate antioxidant activity with increasing viability at 10 μM of 36.1%, 45.0%, 25.5% and 20.7%.

New triterpenoid saponins from the leaves of Ilex chinensis

Eight new triterpenoid saponins, including four ursane-type saponins, ilexchinenosides J-M (1–4), and four oleanane-type saponins, ilexchinenosides N-Q (5–8), along with three known triterpenoid saponins (9–11) were isolated from the leaves of Ilex chinensis Sims. Their structures were established by 1D, 2D NMR and MS spectroscopic analyses and through comparisons with known compounds. Moreover, compounds 1, 3, 5, 7–9 and 11 exhibited significant levels of hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell damage in in vitro assays while compound 10 had moderately inhibitory effects on the NO production of lipopolysaccharide (LPS)-induced murine macrophages.

Computationally Assisted Assignment of the Kadsuraols, a Class of Chemopreventive Agents for the Control of Liver Cancer.

Kadsuraols A-C (1-3), which are tetrahydrocyclobutaphenanthrofuranone-type lignans with a new carbon skeleton comprising a four-membered ring across C-1'-C-8, have been isolated from the roots of Kadsura longipedunculata. Their structures and absolute configurations were unambiguously determined using nuclear magnetic resonance, X-ray diffraction crystallography, DP4+ calculations, and computed and experimental electronic circular dichroism spectra. Kadsuraol C (3) exhibited hepatoprotective activity against N-acetyl- p-aminophenol (APAP)-induced toxicity. The compounds showed no cytotoxicity at 10 μM in a zone assay.

Hepatoprotective glycosides from the rhizomes of Imperata cylindrical

Three new C-methylated phenylpropanoid glycosides (1, 2), a new 8–4′-oxyneolignan (3), together with two known analogs (4, 5), were isolated from the rhizomes of Imperata cylindrical Beauv. var. major (Nees) C. E. Hubb. Their structures were determined by spectroscopic and chemical methods. Compounds 1, 2, and 5 (10 μM) exhibited pronounced hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell damage in vitro assays. Furthermore, their antioxidant activities against Fe2+-cysteine-induced rat liver microsomal lipid peroxidation and the effects on the secretion of TNF-α in murine peritoneal macrophages (RAW264.7) induced by lipopolysaccharides were evaluated.

Triterpenoids from the leaves of Ilex chinensis

Eleven previously undescribed compounds including two triterpenes, ilexchinenin A and ilexchinenin B, and nine triterpenoid saponins, ilexchinenosides A-I, along with twelve known triterpenoids were isolated from the leaves of Ilex chinensis Sims (Aquifoliaceae). Their structures were elucidated by spectroscopic analysis and comparison with known compounds. Furthermore, eight compounds exhibited significant inhibitory effects on NO production of lipopolysaccharide (LPS)-induced murine macrophages, while nine compounds exhibited potent hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell damage in in vitro assays.

New Phenylpropanoid and Coumarin Glycosides from the Stems of Hydrangea paniculata Sieb.

A new phenylpropanoid glycoside (1), and two new coumarin glycosides (2, 3), together with two known compounds (4, 5), have been isolated from the stems of Hydrangea paniculata Sieb. Their structures have been determined by spectroscopic and chemical methods. Furthermore, compound 1 (50 μM) exhibited significant hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell damage in vitro assays.

Assignment of Absolute Configuration of a New Hepatoprotective Schiartane-Type Nortriterpenoid Using X-Ray Diffraction.

A new schiartane-type nortriterpenoid, micrandilactone H was isolated from Kadsura longipedunculata Finet et Gagnep. Its 2D (two dimension) structure was elucidated by NMR spectroscopic analysis, and it is similar to that of Kadnanolactones H and the absolute configuration was established through X-ray diffraction and ECD data analysis. This represents the first complete assignment of the absolute configuration of a schiartane-type nortriterpenoid by X-ray diffraction and the ECD method. Micrandilactone H showed moderate hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced toxicity in HepG2 cells with cell survival rates of 56.84% at 10 μM.

Two new phenylpropanoid glycosides from the aerial parts of Lespedeza cuneata

Two new phenylpropanoid glycosides named cuneataside E (1) and cuneataside F (2), were isolated from the aerial parts of Lespedeza cuneata (Dum. Cours.) G. Don, whose structures were E and Z isomer, respectively. Their structures were elucidated on the basis of comprehensive spectroscopic analysis (UV, IR, HR-ESI-MS, 1D and 2D NMR). In in vitro bioassays at 10μmol/L, compound 1 showed moderate hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced toxicity in HeG2 cells.

Guajavadimer A, a Dimeric Caryophyllene-Derived Meroterpenoid with a New Carbon Skeleton from the Leaves of Psidium guajava.

Guajavadimer A (1), a dimeric sesquiterpene-based meroterpenoid which possessed an unprecedented two caryophyllenes, a benzylphlorogulcinol, and a flavonone-fused complicated stereochemical skeleton, was isolated from the leaves of Psidium guajava L. Its structure and absolute configuration were elucidated on the basis of spectroscopic data and X-ray crystallography. Guajavadimer A (1) showed moderate hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced toxicity in HepG2 cells.