Preparation of novel reagents 4-alkoxytrityl chlorides and their reaction with methyl Α-d-glucoside

A series of novel 4-O-alkoxytrityl chlorides (1) with different chain lengths was synthesized as a novel reagent for obtaining 6-O-alkylated cellulose with high regioselectivity via trityl groups in one reaction step without the use of any protective groups. These chlorides were reacted with methyl -d-glucoside, which was used as a model compound, to examine the reactivities toward the primary hydroxyl groups of cellulose to afford a series of 6-O-alkylated methyl -d-glucosides in high yields. The product compounds were found to have interesting solubilities and thermal properties. Thus, newly prepared trityl chloride derivatives were found to be useful regioselective derivatization reagents on the primary hydroxyl group in carbohydrates, especially in cellulose.     

Effect of fruit load on 9,10-ketol-octadecadienoic acid (KODA), GA and jasmonic acid concentrations in apple buds

The relationship between 9,10-ketol-octadecadienoic acid (KODA), GAs and jasmonic acid (JA) and flower bud formation influenced by fruit load in apples (Malus domestica Borkh.) was investigated. The endogenous KODA and JA concentrations in apical buds in plants subjected to flower thinning treatment (FTT), under which all flowers were removed were higher than those in plants subjected to heavy crop treatment (HCT), under which the number of leaves per fruit was adjusted to 20 from 60 to 120 days after full bloom (DAFB). In contrast, the gibberellic acid concentrations [total of gibberellin A₁ (GA₁) and gibberellin A₄ (GA₄)] in FTT plants were low compared with those in HCT plants. The result suggests that KODA and JA in contrast to GAs may have opposite effects on flower bud formation which is significantly influenced by fruit load in apples and that KODA and JA may also be associated with flower bud formation in apples.     

Protective Effect of Chitin Urocanate Nanofibers against Ultraviolet Radiation

Urocanic acid is a major ultraviolet (UV)-absorbing chromophore. Chitins are highly crystalline structures that are found predominantly in crustacean shells. Alpha-chitin consists of microfibers that contain nanofibrils embedded in a protein matrix. Acid hydrolysis is a common method used to prepare chitin nanofibrils (NFs). We typically obtain NFs by hydrolyzing chitin with acetic acid. However, in the present study, we used urocanic acid to prepare urocanic acid chitin NFs (UNFs) and examined its protective effect against UVB radiation. Hos: HR-1 mice coated with UNFs were UVB irradiated (302 nm, 150 mJ/cm²), and these mice showed markedly lower UVB radiation-induced cutaneous erythema than the control. Additionally, sunburn cells were rarely detected in the epidermis of UNFs-coated mice after UVB irradiation. Although the difference was not as significant as UNFs, the number of sunburn cells in mice treated with acetic acid chitin nanofibrils (ANFs) tended to be lower than in control mice. These results demonstrate that ANFs have a protective effect against UVB and suggest that the anti-inflammatory and antioxidant effects of NFs influence the protective effect of ANFs against UVB radiation. The combination of NFs with other substances that possess UV-protective effects, such as urocanic acid, may provide an enhanced protective effect against UVB radiation.     

Effects of Oral Administration of Fucoidan Extracted from Cladosiphon okamuranus on Tumor Growth and Survival Time in a Tumor-Bearing Mouse Model

We evaluated the anti-tumor activities of the oral administration of fucoidan extracted from Cladosiphon okamuranus using a tumor (colon 26)-bearing mouse model. The materials used included low-molecular-weight fucoidan (LMWF: 6.5–40 kDa), intermediate-molecular-weight fucoidan (IMWF: 110–138 kDa) and high-molecular-weight fucoidan (HMWF: 300–330 kDa). The IMWF group showed significantly suppressed tumor growth. The LMWF and HMWF groups showed significantly increased survival times compared with that observed in the control group (mice fed a fucoidan-free diet). The median survival times in the control, LMWF, IMWF and HMWF groups were 23, 46, 40 and 43 days, respectively. It was also found that oral administration of fucoidan increased the population of natural killer cells in the spleen. Furthermore, from the results of the experiment using Myd-88 knockout mice, it was found that these effects are related to gut immunity. These results suggest that fucoidan is a candidate anti-tumor functional food.