42794-04-7Relevant academic research and scientific papers
LIPID AND STEROIDAL CONSTITUENTS OF LILIUM AURATUM VAR. PLATYPHYLLUM AND L. TENUIFOLIUM
Mimaki, Yoshihiro,Sashida, Yutaka,Shimomura, Hiroko
, p. 3453 - 3458 (1989)
The chemical compounds in the bulbs of Lilium auratum var. platyphyllum and L. tenuifolium have been analysed as part of a systematic study of the genus Lilium.The structures of two new phenylpropanoid glycerol glucosides, regaloside H and I from L. auratum var. platyphyllum, and two new polyhydroxylated steroidal glycosides, tenuifolioside A and B from L. tenuifolium have been elucidated on the basis of the spectroscopic analysis and some chemical transformations.Key Word Index - Lilium auratum var. platyphyllum; Lilium tenuifolium; Liliaceae; acylated glycerol glucosides; regaloside H; regaloside I; polyhydroxylated steroidal glycosides; tenuifolioside A; tenuifolioside B; tenuifoliol.
New Phenylpropanoid Glycerol Glucosides from the Bulbs of Lilium Species
Shimomura, Hiroko,Sashida, Yutaka,Mimaki, Yoshihiro,Kudo, Yashue,Maeda, Katsuhiko
, p. 4841 - 4848 (2007/10/02)
The fresh bulbs of the genus Lilium have yielded new phenylpropanoid glycerol glucosides, epi-regaloside A (6b), epi-regaloside C (7b) and epi-regaloside F (10b), as mixtures with the corresponding (2S)-regalosides (6a, 7a and 10a), and regaloside G (11).Compounds 6b and 7b have been obtained from Lilium pardarinum, and 6b, 10b and 11 from L. auratum.The spectroscopic data and chemical evidence have allowed us to assign the structures of 6b, 7b, 10b and 11 as (2R)-1-O-p-coumaroyl-3-O-β-D-glucopyranosylglycerol, (2R)-1-O-caffeoyl-3-O-β-D-glucopyranosylglycerol, (2R)-1-O-feruloyl-3-O-β-D-glucopyranosylglycerol and (2S)-1-O-feruloyl-2-O- β-D-glucopyranosylglycerol, respectively.In addition, jatropham and its glucoside have been detected in the fresh bulbs of L. medeoloides.Several previously reported compounds have also been obtained and identified.Keywords - Lilium pardarinum; Lilium auratum; Lilium medeoloides; Liliaceae; phenolic glycerol glucoside; epi-regaloside A; epi-regaloside C; epi-regaloside F; regaloside G; jatropham
REGALOSIDE A AND B, ACYLATED GLYCEROL GLUCOSIDES FROM LILIUM REGALE
Shimomura, Hiroko,Sashida, Yutaka,Mimaki, Yoshihiro,Iida, Norio
, p. 451 - 454 (2007/10/02)
Novel acylated glycerol glucosides, regaloside A and B, both bitter to the taste, have been isolated from the fresh bulbs of Lilium regale.Their structures have been shown by the spectral and chemical evidence to be (2S)-1-O-p-coumaroyl-3-O-β-D-glucopyranosylglycerol and (2S)-1-O-p-coumaroyl-2-O-β-D-glucopyranosyl-3-O-acetylglycerol, respectively.Key Word Index - Lilium regale; Liliaceae; acylated glycerol glucosides; p-coumaric acid esters; regaloside A; regaloside B; bitter principles; stereochemistry.
STRUCTURAL INVESTIGATIONS OF THE GALACTAN OF THE SNAIL LYMNAEA STAGNALIS
Bretting, Hagen,Jacobs, Guenter,Thiem, Joachim,Koenig, Wilfried A.,Knaap, Wil van der
, p. 201 - 218 (2007/10/02)
A galactan, isolated from the spawn of the snail Lymnaea stagnalis, contained D-galactose and 0.9percent of nitrogen, but neither L-galactose nor phosphate groups.The D20 values of the galactan and its first Smith-degradation product were +19.5 deg and +20 deg, respectively.During each of two consecutive Smith-degradations of the galactan, 1 mol of periodate was consumed and 0.45 mol of formic acid was liberated per mol of "anhydrogalactose" unit.Methylation analyses of the galactan and its first Smith-degradation product yielded equal proportions of 2,3,4,6-tetra-O-methyl- and 2,4-di-O-methyl-galactose.Only small quantities of 2,4,6- 4.9 molpercent) and 2,3,4-tri-O-methylgalactose (0.7 molpercent) were formed from the galactan, whereas the first Smith-degraded product gave 15.6 and 20.4 molpercent, respectively.The product of the second Smith-degradation disintegrated and the following oligosaccharides were identified: β-D-Gal-(1-1)-L-Gro, β-D-Gal-(1-3)-β-D-Gal-(1-1)-L-Gro, β-D-Gal-(1-6)-β-D-Gal-(1-1)-L-Gro, β-D-Gal-(1-6)-D-Gal-β-D-Gal-(1-3)-β-D-Gal-(1-1)-L-Gro, β-D-Gal-(1-3)--β-D-Gal-(1-1)-L-Gro, β-D-Gal-(1-3)-β-D-Gal-(1-3)-β-D-Gal-(1-6)-β-D-Gal-(1-1)-L-Gro, and β-D-Gal-(1-3)-β-D-Gal-(1-3)-β-D-Gal-(1-1)-L-Gro.Thus, the galactan is highly branched with the backbone containing sequences of either exclusively (1-6)-linked or of more or less regularly alterneting (1-3)- and (1-6)-linked units.The side chains vary in length and in the degree of branching.In immunoprecipitin studies, a high degree of species-specificity was seen when various snail galactans were tested with the antiserum to the Lymnaea stagnalis galactan.
LILIOSIDE C, A GLYCEROL GLUCOSIDE FROM LILIUM LANCIFOLIUM
Kaneda, Miyuki,Mizutani, Kiyoyasu,Tanaka, Keiko
, p. 891 - 894 (2007/10/02)
A new glycerol glucoside, lilioside C, has been isolated from the leaves and stems of Lilium lancifolium.Its structure including the configuration of the aglycone moiety has been elucidated by chemical and spectroscopic means and by its synthesis.Key Word Index - Lilium lancifolium; Liliaceae; tiger lily; glycerol glucoside; 3-O-β-D-glucopyranosyl-sn-glycerol; lilioside C; stereochemistry; synthesis.
