γ-Hydroxynitrile glucosides from the seeds of Prinsepia utilis.

γ-Hydroxynitrile glucosides (prinsepicyanosides A-E) were isolated alongside 11 known compounds from seeds of Prinsepia utilis Royle. Their structures were determined by detailed analysis of NMR and MS spectroscopic data. The relative configuration of prinsepicyanoside C was established by Cu-Kα X-ray crystallography. Prinsepicyanoside A, osmaronin, and 4-(hydroxylmethyl)-5H-furan-2-one exhibited borderline antibacterial activity against Salmonella gallinarum, Vibrio parahaemolyticus, and Vibrio cholera with MIC values of 30.1, 20.7, and 22.8µg/mL, respectively.

Characterization of MMP-9 gene from grass carp (Ctenopharyngodon idella): an Aeromonas hydrophila-inducible factor in grass carp immune system.

Matrix metalloproteinase-9 (MMP-9) belongs to a family of zinc-dependent endopeptidases and is associated with vital inflammatory processes. Here, we isolated and characterized MMP-9 cDNA from grass carp (Ctenopharyngodon idella) (designated as CiMMP-9). The cDNA was 2880 bp long and encoded a putative protein of 675 amino acids, with a predicted molecular mass of 75.816 kDa and an isoelectric point (pI) of 5.25. CiMMP-9 contained all three classical MMP-9 family signatures. The mRNA of CiMMP-9 was constitutively expressed in all tested tissues of untreated grass carp, with the highest expression levels in the blood, trunk kidney, head kidney and spleen. CiMMP9 transcript was present in unfertilized eggs, which suggests that CiMMP9 transcription is maternally inherited. Fluorescent real-time quantitative RT-PCR was used to examine the expression of the CiMMP-9 gene in C. idella after being challenged with Aeromonas hydrophila. A clear time-dependent expression pattern of CiMMP-9 was found after the bacterial challenge, and mRNA expression reached a maximum level at 7 days post challenge. This indicates that MMP-9 is inducible and is involved in immune responses, thus suggesting that CiMMP-9 plays an important role in A. hydrophila-related diseases and in early embryonic development stages in C. idella.

Argutalactone, an unprecedented sesquiterpenoid lactone with a 6/5/7 tricyclic system from Incarvillea arguta.

Argutalactone (1), a novel sesquiterpenoid lactone featuring an unprecedented 6/5/7 rigid skeleton, was isolated from the roots of Incarvillea arguta. The structure and relative configuration of 1 were established by extensive analysis of spectroscopic data. The absolute configuration of 1 was determined as 2R,5S,10R,12S based on the analysis of biogenetical transformation, comparison of the optical rotation with literature data, and comparison of the experimental circular dichroism spectrum with the calculated electronic circular dichroism spectra.

Blumeaenes A-J, sesquiterpenoid esters from Blumea balsamifera with NO inhibitory activity.

Chemical examination of the ethanol extract of the aerial parts of Blumea balsamifera led to the isolation of ten new sesquiterpenoid esters, blumeaenes A-J (1- 10), with 13 known flavonoids. Their structures were determined mainly by use of 1D and 2D NMR spectroscopic techniques. All sesquiterpenoid esters were tested for their inhibitory activity against LPS-induced NO production in RAW264.7 macrophages. Compounds 1, 4 and 5 showed slight inhibitory effect on the production of NO with IC(50) values of 40.06, 46.35 and 57.80 microg/mL, respectively.

Japonicones E-L, dimeric sesquiterpene lactones from Inula japonica Thunb.

Eight new dimeric sesquiterpene lactones (japonicones E-L, 1- 8), including a novel sesquiterpene dimer bearing a rare hydroperoxide group (japonicone E, 1), were isolated from the aerial part of Inula japonica Thunb. Their structures were determined mainly by the use of 1D and 2D NMR spectroscopic techniques including HSQC, (1)H-(1)H COSY, HMBC, and NOESY. All the isolates were tested for inhibitory effects against LPS-induced NO production in RAW264.7 macrophages. Among the compounds tested, japonicone F (2) showed the strongest activity with the IC(50) value of 4.1 microg/mL.

A new ent-kaurane type diterpenoid glycoside from Inula japonica Thunb.

A new ent-kaurane type diterpenoid glycoside, 17-O-beta-D-glucopyranosyl-16alpha-ent-kauran-19-oic acid (1), together with 17-hydroxy-16alpha-ent-kauran-19-oic acid (2), 16alpha,17-dihydroxyl-ent-kauran-19-oic acid (3), and 16alpha-hydroxy-17-acetoxy-ent-kauran-19-oic acid (4) were isolated from the aerial parts of Inula japonica Thunb. The structure of 1 was determined mainly by use of 1D and 2D NMR spectroscopic techniques including HSQC, (1)H-(1)H COSY, HMBC, and NOESY. In addition, 4 exhibited significant inhibitory activity on NO production in LPS-stimulated RAW264.7 cells with IC(50) value of 14.3 microg/mL.

Japonicones A-D, bioactive dimeric sesquiterpenes from Inula japonica Thunb.

Four new dimeric sesquiterpene lactones japonicones A-D (1-4), comprised by eudesmane and guaiane sesquiterpenes, were isolated from the aerial part of Inula japonica Thunb. The structures and stereochemistry of 1-4 were elucidated by use of 2D NMR spectroscopic techniques, X-ray crystallography and modified Mosher method. Japonicone A (1) showed the most potent cytotoxicities against four tumor cell lines, A549, LOVO, CEM and MDA-MB-435.