Structures and Biological Activities of Polyacylated ent-Kaurane Diterpenoid Glycosides from the Aerial Parts of Inula hupehensis.

Sixteen new (1-16) and three known (17-19) polyacylated ent-kaurane diterpenoid glycosides were isolated from the aerial parts of Inula hupehensis. The planar structures of 1-16 and their relative configurations were established on the basis of extensive spectroscopic analysis. The absolute configurations of all stereogenic centers for compounds 1 and 6 were determined by single-crystal X-ray diffraction experiments, and the absolute configurations of the other new compounds were assigned by chemical degradation and experimental ECD data. Antineuroinflammatory testing of all the isolates showed that compound 5 inhibited lipopolysaccharide-induced nitric oxide production in BV-2 microglial cells with an IC50 value of 15.6 µM. In an α-glucosidase inhibitory assay, compound 13 exhibited a strong inhibitory effect with an IC50 value of 32.8 µM, whereas the IC50 value of the positive control, acarbose, was 387.8 µM.

Sesquineolignan and neolignan enantiomers from Triadica sebifera.

Two pairs of new sesquineolignan enantiomers (1a/1b and 1c/1d), two pair of new 4',7-epoxy-8,3'-neolignan enantiomers (2a/2b and 3a/3b), and a pair of new 3',7-epoxy-8,4'-oxyneolignan enantiomers (4a/4b), along with two pairs of known 4',7-epoxy-8,3'-neolignan enantiomers (5a/5b and 6a/6b), were obtained from the stems and leaves of Triadica sebifera. The structures of the enantiomers were elucidated by spectroscopic analyses, and their absolute configurations were assigned by the experimental ECD spectra. Among them, compounds 5b, 6a and 6b showed inhibitory activities against NO production in activated microglial BV-2 cells, with IC50 values of 14.3, 23.2 and 33.3 µM, respectively.

3α,19-Dihydroxyl-ent-pimara-8(14),15-diene, a new diterpenoid from the rhizomes of Ricinus communis.

A new natural product, 3α,19-dihydroxyl-ent-pimara-8(14),15-diene (1), which possesses an α-orientation hydroxymethyl at C-4 and ∆8,14 groups, as well as eight known compounds, was isolated from the rhizomes of Ricinus communis. The structure of 1 was elucidated by extensive spectroscopic methods and its absolute configurations were confirmed by X-ray crystallographic analysis. The inhibitory rate of 1 against protein tyrosine phosphatase 1B (PTP1B) was 49.49% at the concentration of 6.58 × 10-5 mol/L.

[Study on chemical constituents of stems and leaves of Sapium discolor].

Seventeen compounds were isolated from the 95% ethanol extract of the stems and leaves of Sapium discolor by using various chromatographic techniques,including silica gel,Sephadex LH-20,MCI,ODS,and semi-preparative HPLC. Their structures were elucidated as sapiumin F( 1),kadsulignan C( 2),ciwujiatone( 3),ethylbrevifolin carboxylate( 4),7-hydroxy-8-methoxycoumarin( 5),fraxetin( 6),fraxidin( 7),isofraxidin( 8),6,7,8-trimethoxycoumarin( 9),5,6,7,8-tetramethoxycoumarin( 10),8-hydroxy-5,6,7-trimethoxycoumarin( 11),3,3'-di-O-methylellagic acid( 12),3,3',4'-tri-O-methylellagic acid( 13),3'-methoxyellagic acid 4'-O-α-rhamnopyranoside( 14),4,5-didehydro-chebulic acid triethyl ester( 15),ent-kaurane-3-oxo-16α,17-diol( 16),and abscisic acid( 17) by spectroscopic data. Compound 1 is a new compound. Except for compounds 4,11,and 13,the remaining compounds were isolated from this plant for the first time. All the isolates were evaluated for their in vitro antineuroinflammatory activities,and the results showed that compounds 6 and 15 significantly inhibited nitric oxide production in lipopolysaccharide-induced BV-2 microglial cells,with IC50 values of 6. 06 and 6. 05 µmol·L-1,respectively.

Coumarinolignoids and Taraxerane Triterpenoids from Sapium discolor and Their Inhibitory Potential on Microglial Nitric Oxide Production.

Seventeen compounds, including three new pairs of coumarinolignoid enantiomers, (7' S,8' S)-sapiumins A-C (1a-3a) and (7' R,8' R)-sapiumins A-C (1b-3b), six new taraxerane triterpenoids, sapiumic acids A-F (4-9), and five known taraxerane triterpenoids (10-14), were isolated from an ethanol extract prepared from the stems and leaves of Sapium discolor. The structures of 1-9 and their relative configurations were determined by spectroscopic data analysis, and the absolute configurations of the coumarinolignoids 1a/1b-3a/3b and triterpenoids 6-9 were assigned using experimental and calculated ECD data. Compounds 1a/1b-3a/3b are the first coumarinolignoids to be reported from the genus Sapium. Among all the isolates, compounds 1b, 2a/2b, 3a/3b, and 6-9 inhibited nitric oxide production in lipopolysaccharide-stimulated BV-2 microglial cells, with IC50 values of 1.7-15.3 µM.

Clerodane Diterpenoid Glucosides from the Stems of Tinospora sinensis.

Ten new clerodane diterpenoid glucosides (1-10) and three known analogues (11-13) were isolated from an EtOAc extract of the stems of Tinospora sinensis. Spectroscopic analyses and chemical methods were used to elucidate the structures of these isolates. The absolute configurations of tinosinenosides A-C (1-3) were established by using experimental and calculated ECD data. Their cytotoxicity against the human epithelioid cervical carcinoma (HeLa) cell line and the nitric oxide production inhibitory activity of lipopolysaccharide-activated N9 microglial cells were tested. 1-Deacetyltinosposide A (12) exhibited mild cytotoxicity against HeLa cells, with an IC50 value of 8.35 ± 0.60 µM.

[Studies on chemical constituents of Clerodendrum bungei].

Ten compounds were isolated from the 95% aqueous EtOH extract of Clerodendrum bungei by a combination of various chromatographic techniques including column chromatography over silica gel, Sephadex LH-20, MCI, ODS, and semi-preparative HPLC. Their structures were elucidated as 11,12,16S-trihydroxy-7-oxo-17(15→16),18(4→3)-diabeo-abieta-3,8,11,13-tetraen-18-oic acid (1), 12S*,13R*-dihydroxy-9-oxo-octadeca-10(E)-enoic acid (2), clerodenoside A (3), trichotomoside (4), glycosmisic acid (5), 4'-O-methylscutellarein (6), neroplomacrol (7), butylitaconic acid (8), hexylitaconic acid (9), p-hydroxybenzonic acid (10) by their physicochemical properties and spectroscopic data. Compounds 1 and 2 are new natural products, while compounds 7-10 were obtained from the genus Clerodendrum for the first time, and compounds 3, 5, 6 were isolated from this plant for the first time.

Cytisine-type alkaloids and flavonoids from the rhizomes of Sophora tonkinensis.

A new cytisine-type alkaloid, (-)-N-hexanoylcytisine (1), and a new isoflavan, (3S, 4R)-4-hydroxy-7,4'-dimethoxyisoflavan 3'-O-ß-d-glucopyranoside (2), along with 10 known compounds, were isolated from the rhizomes of Sophora tonkinensis. Their structures were determined by spectroscopic methods, chemical evidence, and ECD data analysis. All of the isolates were evaluated for their cytotoxic activities against four human tumor cell lines.

[A new indole alkaloid from the stems of Brucea mollis].

Eight compounds were isolated from the stems of Brucea mollis by various chromatographic techniques such as column chromatography on silica gel and Sephadex LH-20, and preparative HPLC, and their structures were elucidated as bruceolline O (1), 1-(1-beta-glucopyranosyl)-1H-indole-3-carbaldehyde (2), canthin-6-one (3), 11-hydroxycanthin-6-one (4), 9-methoxycanthin-6-one (5), 4-methoxycanthin-6-one (6), infractin (7), and beta-carboline-1-propionic acid (8). The cytotoxic activities of compounds 1-8 against HCT-8 and A549 human cell lines were determined, but none of them exhibited significant activity (IC 50 > 10 micromol x L(-1)). Among them, compound 1 is a new indole alkaloid, and compounds 2 and 5-7 were isolated from this plant for the first time.

Hysterolides A-I, dimeric or monomeric sesquiterpene lactones from Parthenium hysterophorus L.

Nine undescribed sesquiterpene lactones, including two pseudoguaianolide dimers (1 and 2), a pseudoguaiac dilactone (3), and six pseudoguaianolides (4-9), along with 13 known analogues (10-22) were isolated from Parthenium hysterophorus. Among them, hysterolide A (1) possesses an unusual carbon skeleton with a unique cyclobutane ring connecting two pseudoguaianolides. Hysterolide C (3) is a sesquiterpene dilactone incorporating a bicyclo[5.1.0]octane core. Spectroscopic analyses, 13C NMR and ECD calculations, and X-ray diffraction elucidated their structures and absolute configurations. Moreover, all the isolates were assayed for their anti-inflammatory activities by inhibiting LPS-induced nitric oxide production in BV-2 microglia cells, wherein, nine compounds displayed significant inhibitory activities with IC50 of 0.52-6.32 µM. Furthermore, the preliminary structure-activity relationship was also established.

Eudesmane sesquiterpenoids with inhibitory effects on NO production from Artemisia princeps.

Five undescribed eudesmane methyl esters (1-5), three undescribed eudesmane-12,6-olides (6-8), and 21 known analogues (9-29) were isolated from the aerial part of Artemisia princeps Pamp. Their structures were established by detailed analysis of the NMR and HRESIMS data. The absolute configurations of 1-8 were determined based on single-crystal X-ray diffraction analysis and ECD calculations. Moreover, the inhibitory effects on LPS-induced NO production in BV-2 microglial cells of all the isolated compounds were assessed. Except for compounds 2, 4, 10, and 11, the others showed significant inhibitory activities, with IC50 values of 0.73-18.66 µM, wherein the potential structure-activity relationship was also discussed.

Diterpenoids and sesquiterpenoids from the roots of Illicium majus.

Five new diterpenoids (1-5), five new sesquiterpenoids (6-10), and three known compounds (11-13) were isolated from the roots of Illicium majus. Their structures were elucidated by extensive spectroscopic analysis. The absolute configuration of 1 was assigned by X-ray crystallography, whereas those of the 1,2-diol moieties in 3 and 4 were determined using Snatzke's method. The abietane acids 1, 2, 11, 12, and 13 displayed antiviral activity against the Coxsackie B3 virus, with IC50 values of 3.3-51.7 µM/mL.

Diterpenoids and sesquiterpenoids from the twigs and leaves of Illicium majus.

Four new abietane diterpenes (1-4) and two new cycloparvifloralone-type sesquiterpenoids (5-6) have been isolated from the twigs and leaves of Illicium majus, together with three known sesquiterpenoids and five known diterpenoids. Their structures were determined by spectroscopic analysis and chemical methods. The absolute configuration of the 15,16-diol moiety in 2 is confirmed by Snatzke's method, observing the induced circular dichroism after the addition of dimolybdenum tetraacetate in DMSO. Compound 2 exihibited significant anti-inflammatory activity with an IC50 value of 0.26 ± 0.03 µM, while compounds 10, 11, and 13 showed good anti-inflammatory activities with IC50 values ranging from 1.94 ± 0.56 to 2.60 ± 0.48 µM.

Novel sesquiterpenoid glycosides and sesquiterpenes from the roots of Illicium henryi.

Seven new sesquiterpenoid glycosides, consisting of one thapsan-type (1), two capnellane-type (2 and 3), four floridanolide sesquiterpene glycosides (4-7), and one new azulene-type sesquiterpene (8), along with six known sesquiterpenes (9-14) were isolated from the roots of Illicium henryi. The structures of 1-8 were elucidated by extensive spectroscopic analyses and chemical methods. The absolute configurations of 1, 2, and 8 were determined based on Rh2(OCOCF3)4-induced CD, Mo2(OAc)4-induced CD data, and calculated electronic circular dichroism (ECD), respectively. Compound 1 was found to exhibit weak neurotoxicant activity.

Bioactive quassinoids from the seeds of Brucea javanica.

Six new quassinoids (1-6) and eight known compounds of this type (7-14) were isolated from the seeds of Brucea javanica. Their structures were elucidated by analysis of their spectroscopic data and from chemical evidence. Compounds 1-5 were found to be unusual quassinoids with a 2,3-seco A ring. The configurations at C-4 in 4 and 5 were determined by a difference circular dichroism method. In in vitro bioassays, 8 and 10 showed inhibitory activities for nitric oxide production in LPS-activated macrophages, with IC(50) values of 1.9 and 5.0 µM, respectively, while compounds 6, 8-11, 13, and 14 exhibited cytotoxicity against five human tumor cell lines (HCT-8, HepG2, BGC-823, A549, and SKVO3), having IC(50) values in the range 0.12-9.3 µM.

Xanthones from the stems of Calophyllum membranaceum Gardn. et Champ. and their anti-inflammatory activity.

Eighteen undescribed xanthones, including six pairs of xanthone enantiomers, three xanthones, and three xanthone glycosides, together with one pair of known xanthone enantiomers and 12 known xanthones, were isolated from the stems of Calophyllum membranaceum Gardn. et Champ. Their structures were elucidated by spectroscopic analysis, and the absolute configuration of the enantiomers was determined by using experimental and calculated electronic circular dichroism data. All compounds were screened for their anti-inflammatory effects on LPS-induced BV-2 microglial cells. Among them, six compounds showed remarkable activities with IC50 values of 7.8-36.0 µM.

Supplementation of guanidinoacetic acid and rumen-protected methionine increased growth performance and meat quality of Tan lambs.

OBJECTIVE: Tan lambs (n = 36, 3 mo old, 19.1±0.53 kg) were used to assess effects of dietary guanidinoacetic acid (GAA) and rumen-protected methionine (RPM) on growth performance, carcass traits, meat quality, and serum parameters. METHODS: Lambs were randomly assigned to three treatment groups, with 6 pens per group and 2 lambs per pen. Dietary treatments were: basal diet alone (I); basal diet supplemented with 0.08% GAA+0.06% RPM (II); and basal diet supplemented with 0.08% GAA+0.08% RPM (III). Diets were provided three times a day for 90 d. Intake per pen was recorded daily and individual lamb body weight (BW) was measured monthly. Carcass traits were measured after slaughter and meat quality at the end of the experiment, blood samples were taken on a subgroup of lambs for analysis of indicators mostly related to protein metabolism. RESULTS: Final BW and average daily gain for the first and second month, and for the entire experiment were greater in Treatment II compared to Treatment I (p<0.05), whereas feed to gain ratio was lower (p<0.05). Treatment II had the optimal dressing percentage and net meat weight proportion, as well as crude protein and intramuscular fat concentrations in muscles. Treatment II improved meat quality, as indicated by the greater water holding capacity, pH after 45 min and 48 h, and lower shear force and cooking loss. Dietary supplementation of GAA and RPM also increased the meat color a* and b* values at 24 h. Finally, Treatment II increased total protein, and serum concentrations of albumin and creatinine, but decreased serum urea nitrogen concentrations, indicating improved protein efficiency. CONCLUSION: In this study, 0.08% GAA+0.06% RPM supplementation improved growth performance and meat quality of Tan lambs.

Cytotoxic triterpenoid saponins from Lysimachia clethroides.

Seven oleanane-type triterpenoid saponins, named clethroidosides A-G (1-7), an ursane-type triterpenoid saponin, clethroidoside H (8), and six known saponins were isolated from the aerial parts of Lysimachia clethroides. The structures of the saponins were elucidated on the basis of physical data analysis (1D and 2D NMR, HR-ESIMS) and chemical evidence. The cytotoxic activities of compounds 1-14 were evaluated against five human tumor cell lines (HT-29, HePG2, BGC-823, A549, and A375). Compounds 3, 4, 6, and 11-13 exhibited moderate cytotoxic activity, with IC50 values of 0.75-2.62 µM, while compound 5 showed selective cytotoxic activity.

Coumarinolignoids and lignanoids from the stems and leaves of Sapium discolor.

Two new coumarinolignoids, sapiumins D (1) and E (2), a new lignanoid, lariciresinol 9'-benzoate (3), together with six known coumarinolignoids (4-9) and eight known lignanoids (10-17), were isolated from the stems and leaves of Sapium discolor. The structures of the isolated compounds were elucidated by extensive spectroscopic methods, including NMR, MS, and single crystal X-ray diffraction experiments. Compounds 5, 10, 11, and 13 significantly inhibited nitric oxide production in lipopolysaccharide-induced BV-2 microglial cells, with IC50 values in the range of 2.13-11.37 µM.

Sesquiterpenes and diterpenes from Euphorbia thymifolia.

One new pseudoguaianolide (1), one new megastigmane (6), and one new ent-abietane diterpene (9), together with seven known compounds (2-5, 7, 8, and 10) were isolated from the aerial parts of Euphorbia thymifolia. The structures of the new compounds and their relative configurations were determined by spectroscopic data analysis. The absolute configurations of compounds 1, 6, and 9 were determined by single-crystal X-ray crystallographic analysis, modified Mosher's method and calculated ECD experiment, respectively. All compounds were tested for their inhibitory effects against LPS-induced NO production in BV-2 microglial cells, and pseudoguaianolides (1-5) showed significant activity with IC50 values of 0.41-15.32 µM.