Novel rutinosides of vanillic acid, sinapic acid, ferulic acid, and caffeic acid were prepared via a rutinase-catalyzed transglycosylation reaction. Reaction mixtures containing rutin, phenolic acid, and rutinase derived from tartary buckwheat ( Fagopyrum tataricum ) seeds were incubated in 20 mM acetate buffer (pH 5.0) at 40 °C. The resulting rutinoside of each phenolic acid was purified by HPLC, and the structure was determined by NMR and FAB-MS analysis. Antiviral activity was determined using feline calicivirus (FCV) strain F9, which is a typical norovirus surrogate. It was found that rutinosylation of the phenolic acids increased their antiviral activity against FCV, with the sinapic acid rutinoside being the most effective. These results will contribute to the development of antiviral agents against noroviruses.

The purpose of this study was to screen phytochemicals capable of inducing immune tolerance via enhanced transforming growth factor-β1 (TGF-β1) secretion and investigate their effects in a mouse model of food allergy and colitis. In a screening test using THP-1-derived dendritic cells, a significant increase in TGF-β1 levels was observed upon treatment with ferulic acid and its glycosides, among which ferulic acid rutinoside (FAR) induced the highest level of TGF-β1 secretion. Oral administration of FAR suppressed serum levels of immunoglobulin E and histamine in ovalbumin-sensitized mice and triggered the differentiation of regulatory T (Treg) cells. In comparison to the control, FAR treatment also induced stronger TGF-β1 secretion from splenic dendritic cells. FAR treatment attenuated dextran-sulfate-sodium-induced colitis in the model mice and induced Treg differentiation. These results suggest that FAR exerts potent immunomodulatory effects against allergic and intestinal inflammatory responses by inducing Treg differentiation.

Fish collagen is one of the major allergens involved in fish allergies; however, it has not been well-established whether fish collagen can cause anaphylaxis among individuals with fish allergies, especially children. A 9-year-old girl experienced anaphylaxis after consuming 2 fruit-flavored gummy tablets. Contacting the manufacturing company revealed that fishderived collagen was used in the gummy tablets, and an oral fish collagen challenge test confirmed that the anaphylaxis was induced by fish collagen. Immunoblot analysis showed a 120-kDa band in a sample of the fish collagen in the gummy tablets, and no reactive band of the pork gelatin was observed. Additionally, salmon collagen and other fish samples that provoked symptoms were detected as a 120-kDa band in the immunoblot analysis. The 120-kDa band was identified as fish collagen by mass spectrometry confirming that it was the causative antigen of our patient's allergy. This case study confirms that fish collagen can cause anaphylaxis in children with fish allergies. Physicians and allergic individuals need to be aware that processed foods may contain fish collagen to avoid allergic reactions.

Fish collagen as a potential indicator of severe allergic reactions among patients with fish allergies.