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Гришковец, В. И.; Sobolev, E. A.; Шашков, А. С.; Chirva, V. Ya.

doi:10.1023/a:1002891507725

Cited by 17 publications

(13 citation statements)

References 6 publications

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“…After signals for all H atoms were assigned based on the HSQC spectrum, signals for the C atoms were completely assigned. The magnitudes of the chemical shifts for the C and H atoms in the glucose units showed that they were similar to those of glucopyranose units in the trisaccharide fragment Rha 1 → 4 Glc 1 → 6 Glc→, which is typical of Araliaceae glycosides [1,3]. However, the chemical shifts of the rhamnopyranose units were substantially different.…”

Section: Structures Of 13 New Acetylated Triterpene Glycosides From Lmentioning

confidence: 99%

“…The progenin of this glycoside was obtained by alkaline hydrolysis and was identical by TLC to the 3-O-α-L-arabinopyranoside of oleanolic acid [1]. Signals in the 13 C NMR spectrum for C atoms of the α-L-arabinopyranosyl fragment and the 2-O-acetyl-and 3-O-acetyl-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl fragments described above for 1 and 2 were assigned using literature data [3]. However, like for previously described glycosides of fractions B and H [1], the signals of the aglycon part of the 13 C NMR spectrum were consistent with the presence of two aglycons, oleanolic and ursolic acids, in a 4:1 mole ratio.…”

Section: Structures Of 13 New Acetylated Triterpene Glycosides From Lmentioning

confidence: 99%

“…It was assumed based on these data that 4 and 5 were isomers at the acyl group. Signals for α-L-arabinopyranose and disubstituted hederagenin were assigned in the 13 C NMR spectra of 4 and 5 using literature data [3].…”

Section: Structures Of 13 New Acetylated Triterpene Glycosides From Lmentioning

confidence: 99%

“…Signals for C atoms at 21.2 and 170.9 ppm were assigned to an acetyl ester. The α-and β-effects on the H and C atoms of the carbohydrate of 4 compared with the unsubstituted trisaccharide [3] showed that rhamnose C-4 had an O-acetyl. The location of the acetate was also confirmed using the HMBC spectrum, in which a cross-peak was observed between rhamnose H-4 and an acetate carbonyl C atom.…”

Section: Structures Of 13 New Acetylated Triterpene Glycosides From Lmentioning

confidence: 99%

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Triterpene Glycosides from Cussonia paniculata. II. Acetylated Glycosides from Leaves

Гришковец¹,

Dovgii²,

Качала

et al. 2005

Chem Nat Compd

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6a and 6b). The structures of the compounds were established using chemical methods and NMR spectroscopy.We previously reported [1] the isolation and structure of eight unacetylated glycosides from leaves of Cussonia paniculate Eckl. et Zeih. In the present article, the glycoside composition of the leaves of this plant is studied. It was noted previously [1] that the leaves contain a large quantity of acylated glycosides according to two-dimensional (2D) TLC [2]. The proof of structure of these is given herein.Glycoside F (3) was obtained during separation of the purified total triterpene glycosides [1] as a pure compound by TLC in various solvent systems whereas fractions E, G, and I formed a group of glycosides with similar chromatographic mobilities. Rechromatography of fraction E produced glycosides E 1 (1) and E 2 (2); fraction G, G 1 (4), G 2 , and G 3 (5) [1]; fraction I, I 1 , I 2 , and I 3 (6).Total acid hydrolysis of 1 produced rhamnose and glucose in addition to the aglycon, which had the same chromatographic mobility as hederagenin. However, the color the chromatographic band differed from it upon development by phosphotungstic acid. The progenin obtained by alkaline hydrolysis was identical to the aglycon. This indicated that the aglycon had no carbohydrate chain on C-3. We assumed that the aglycon, like hederagenin, contained one additional hydroxyl in addition to the usual hydroxyl on C-3 and carboxyl on C-28. Then, we used NMR spectroscopy to establish the structures of the aglycon and the carbohydrate chain and to determine the type of acyl group and its location.Six signals were found in the 13 C NMR spectrum of 1 in the range of anomeric C atoms (95-108 ppm). However, the chromatographic mobility of the glycoside showed that it should contain three carbohydrate residues. Obviously, 1 contained two isomeric glycosides with different acetylated carbohydrate fragments because signals for two O-acetyls (methyl and carbonyl C atoms) were observed in the spectrum at 21.0, 21.2, 171.1, and 171.2 ppm. Signals of the corresponding anomeric protons were found from the signals of the anomeric C atoms in the 2D HSQC spectrum.

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Section: Structures Of 13 New Acetylated Triterpene Glycosides From Lmentioning

confidence: 99%

Section: Structures Of 13 New Acetylated Triterpene Glycosides From Lmentioning

confidence: 99%

Section: Structures Of 13 New Acetylated Triterpene Glycosides From Lmentioning

confidence: 99%

Section: Structures Of 13 New Acetylated Triterpene Glycosides From Lmentioning

confidence: 99%

See 2 more Smart Citations

Triterpene Glycosides from Cussonia paniculata. II. Acetylated Glycosides from Leaves

Гришковец¹,

Dovgii²,

Качала

et al. 2005

Chem Nat Compd

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show abstract

“…Fraction G of variety maximowiczii contained pure glycoside G (9); of variety typicum, the glycoside pair G 1 (8) and G 2 (10). Fraction H of variety typicum contained the principal glycoside H 1 (11) [1] and two minor glycosides H 2 (12) and H 3 (13). Analogously, fraction I of variety typicum contained the principal glycoside I 2 (15) [1] and another minor glycoside I 1 (14).…”

mentioning

confidence: 99%