New furospirostane steroidal saponins from the flowers of Lilium Asiatic hybrids.

Lilium Asiatic hybrids (Lilium spp.) are produced by interspecific crosses of Sinomartagon species belonging to Liliaceae. To date, no phytochemical work appears to have been conducted on Lilium Asiatic hybrids. In the current work, solvent extraction, solvent fractionation, and repeated SiO2 and ODS column chromatography yielded three new steroidal saponins along with a known one, avenacoside A (1). The chemical structures of the new saponins were determined based on extensive spectroscopic methods as well as chemical and biological reactions to be 26-O-ß-D-glucopyranosylnuatigenin 3-O-α-l-rhamnopyranosyl-(1 → 2)-O-[(4-O-methyl)-ß-d-glucopyranosyl-(1 → 6)-ß-d-glucopyranosyl-(1 → 4)]-ß-d-glucopyranoside (2), 26-O-ß-D-glucopyranosylnuatigenin 3-O-ß-d-glucopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-(6-acetoxyl)-ß-d-glucopyranoside (3), and 26-O-ß-D-glucopyranosylnuatigenin 3-O-ß-d-glucopyranosyl-(1 → 2)-O-[ß-d-glucopyranosyl-(1 → 6)]-ß-d-glucopyranoside (4), named lilyasiasides A-C, respectively. The aglycone of the saponins, a nuatigenin, is an atypical spirostanol sapogenin possessing a pentacyclic F-ring, furospirostane steroid, which is very rarely occurred in Lilium species.

Enzymatic synthesis of ß-galactosyl fucose using recombinant bifidobacterial ß-galactosidase and its prebiotic effect.

Breast-fed infants have Bifidobacterium-rich gut microbiota compared to infants fed formula. Fucosylated oligosaccharides are the major components of human milk oligosaccharide (HMO) which confer various beneficial effects including prebiotic effect and protection from pathogenic infection on the host. A novel prebiotics was developed using bifidobacterial ß-galactosidase and fucose and lactose as substrates. Structure analysis revealed it as ß-D-galactopyranosyl-(1 → 3)-O-L-fucopyranose named as ß-galactosyl fucose (gal-fuc), which is different from common fucosylated HMOs with α1-2, α1-3, and α1-4 linkages. Among the four Lactobacillus strains examined, all but L. delbrueckii subsp. bilgaricus KCTC 3635 grew better on gal-fuc than on ß-GOS. Among the 11 bifidobacterial species examined, all except for B. bifium used gal-fuc as much as GOS. Moreover, the gal-fuc was noticeably better used by Bifidobacterium infantis, the major intestinal bacteria of breast fed infant. Among 15 non-probiotic bacteria, only 4 strains used gal-fuc better than ß-GOS. In conclusion, a novel gal-fuc is expected to contribute to beneficial changes of gut microbiota. Graphical abstract A novel form of ß-galactosyl fucose with an improved prebiotic effect.