Carotenoids and their fatty acid esters were investigated in the petals of Adonis aestivalis by UV-VIS, 1H-NMR, FAB-MS, and CD spectrometry. (3S,3'S)-astaxanthin (diester: 72.2%, monoester: 13.8%, free: 1.4%) and (3S)-adonirubin (monoester: 13.8%, free: 0.3%) were identified as the major components. The fatty acids esterified with astaxanthin and adonirubin were assigned as C18:0, C18:1, C16:0, C16:1, C14:0, C12:0, and C10:0 from the FAB-MS spectral data.
Seventeen limonoids (tetranortriterpenoids 1-17) were isolated from the n-hexane extract of Azadirachta indica (neem) seeds. The previously unidentified compound 16 was established by spectroscopy to be 17-defurano-17-oxosalannin. The effects of six compounds, 6 and 11-15, on melanogenesis in B16 melanoma cells was evaluated; 2 compounds, salannin (13) and 3-deacetylsalannin (15), exhibited marked inhibitory effects (70-74% reduction of melanin content at 25 μg/mL) with only minor cytotoxicity (79-85% of cell viability). Eleven compounds, 2, 3, 5, 6, and 9-15, were evaluated for inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1.7 nmol/ear) in mice; all exhibited marked anti-inflammatory activity (ID50 values 0.22-0.57 μmol/ear). In addition, compounds 6 and 11-16 exerted moderate inhibition (IC50 values of 410-471 mol ratio/32 pmol TPA) of TPA-induced Epstein-Barr virus early antigen (EBV-EA) activation in Raji cells. The triacylglycerol fraction of the n-hexane extract contained oleic acid (50.2%) as the most predominant fatty acid constituent.
Ester-type tartaric gemini amphiphiles bearing two carboxyl groups and two hydrophobic alkanoyl groups were prepared from L-tartaric acid, and the pressure-area (π-A) isotherms for a series of symmetric tartaric gemini amphiphiles were measured by the conventional film-balance technique. The effects of the length of the hydrophobic alkanoyl chains and of the subphase temperature (Tsub) on the π-A isotherms for these compounds were examined. As the length of the hydrophobic alkyl chain increased, a more tightly packed monolayer was formed at the air-water interface. The melting temperature (Tm) of the monolayer on the water surface was evaluated from the subphase temperature (Tsub) dependence of the monolayer static elasticity εs, based on a π-A isotherm. A clear relationship between Tm and hydrophobic carbon number (n) was observed for 2D monolayers of tartaric geminis on water surfaces, as well as for fatty acids and/or 3D solids.
The ethyl acetate (EtOAc)-soluble fraction of a methanol extract of Angelica keiskei roots exhibited cytotoxic activity against 4 human tumor cell lines, HL60 (leukemia), CRL1579 (melanoma), A549 (lung), and AZ521 (stomach). Nine chalcones (1–9), 5 coumarins (10–14), and 4 flavanones (15–18), isolated from the EtOAc-soluble fraction, were examined for their cytotoxic activities in the 4 human tumor cell lines. Among the compounds tested, 4-hydroxyderricin (2), a major chalcone constituent, exhibited potent cytotoxic activities in all 4 tumor cell lines with IC50 values of 5.5 μM (HL60), 4.8 μM (CRL1579), 10.2 μM (A549), and 4.2 μM (AZ521). 4-Hydroxyderricin induced early apoptosis in HL60 cells, observed as membrane phospholipid exposure in flow cytometry. Western blot analysis showed that 4-hydroxyderricin markedly reduced the levels of procaspases-3, -8, and -9, while increasing the levels of cleaved caspases-3, -8, and -9. In addition, 4-hydroxyderricin exhibited potent inhibitory activity on human DNA topoisomerase (Topo) II (IC50 21.9 μM). These results suggested that 4-hydroxyderricin induces apoptotic cell death in HL60 via both the death receptor-mediated pathway and the mitochondrial pathway by, at least in part, Topo II inhibition. 4-Hydroxyderricin may therefore hold promise as an effective antitumor agent.
The serum phosphorus level is recently considered as one of the foretelling markers for the severity of cardiovascular diseases (CVD). We therefore investigated whether the serum phosphorus level in the diabetic patients against healthy individuals could act as a possible marker for identification of vulnerability to cardiovascular disease. One hundred and thirty two human subjects were involved in the study among which one hundred and four subjects are CVD patients and twenty eight were healthy individuals. The levels of the lipid profile and the glycemic status were significantly increased in the patients than those of the control subjects (Fasting glucose, FS=8.3±0.3 vs. 6.1±0.0 mmol/L; blood glucose 2 h after breakfast (STAB)=12.0±0.5 vs. 8.5±0.7, mmol/L; HbA1c (%),6.7±0.2 vs. 5.4±0.3; and Total cholesterol (TC)=189±4.0 vs. 162±7.0; low density lipoprotein cholesterol (LDL-C), 111±3.8 vs. 96±5.0; triacyglycerol (TG), 202±9.0 vs. 118±5.3 mg/dL, respectively. The serum phosphorus level was significantly increased in CVD patients (mg/dL, patient vs. control, 5.1±0.10 vs. 3.7±0.1). Simple regression analyses revealed a highly significant positive correlation between serum phosphorus and TC, TG and FG. Thus the results demonstrate that the serum phosphorus level might be another parameter which is closely associated with diabetes and could also be used as a possible marker for the risk of CVD.
The enoyl-coenzyme A (CoA) hydratase catalyzes the hydration of 2-enoyl-CoA to yield 3-hydroxyacyl-CoA in mitochondrial and peroxisomal β-oxidation. However, the stereospecificities of these hydratases differ from each other. To provide clear evidence of the stereospecificities of hydratases, the absolute configuration of 3-hydroxyhexadecanoyl-CoAs was determined, and they were subjected to a high-performance liquid chromatography (HPLC) using a chiral separation column. The retention time of 3(R)-hydroxyhexadecanoyl-CoA was shorter than that of 3(S)-hydroxyhexadecanoyl-CoA. The HPLC analysis carried out using a chiral separation column is considered to be useful for the study of enoyl-CoA hydratase.
Thin-layer chromatography (TLC) is an essential method for food composition analyses such as lipid nutrition analysis. TLC can be used to obtain information about the lipid composition of foods; however, it cannot be used for analyses at the molecular level. Recently we developed a new method that combines matrix-assisted laser desorption/ionization imaging mass spectrometry (MALDI-IMS) with TLC-blotting (TLC-Blot-MALDI-IMS). The combination of MALDI-IMS and TLC blotting enabled detailed and sensitive analyses of lipids. In this study, we applied TLC-Blot-MALDI-IMS for analysis of major phospholipids extracted from bluefin tuna. We showed that TLC-Blot-MALDI-IMS analysis could visualize and identify major phospholipids such as phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, phosphatidylcholine, and sphingomyelin.