Triterpene glycosides ofCephalaria gigantea. III. The structure of giganteasides E and H

Zviadadze, L. D.; Dekanosidze, G. E.; Dzhikiya, O. D.; Kemertelidze, E. P.

doi:10.1007/bf00579959

Cited by 10 publications

(20 citation statements)

References 4 publications

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“…General 1 H-and 13 C-NMR spectra were recorded on a Bruker DRX-500 spectrometer in CD 3 Extraction and Isolation Dried and powdered roots of C. gigantea (500 g) were extracted with boiling 80% MeOH (4 l). The extract was concentrated under vacuum.…”

Section: Methodsmentioning

confidence: 99%

“…Saponins containing glucuronic acid in the sugar chain are reported for the first time in Cephalaria species. In addition, eight known triterpene glycosides, giganteosides D (4), 5) E (5), 5) G (6), 6) H (7), 6) I (8), 8) K (9), 8) J (10) 9,10) and J 1 (11) 9,10) were isolated from this plant.Dried root of C. gigantea was extracted with boiling 80% MeOH and after filtration the solution was evaporated. The solid residue was dissolved in methanol and precipitated in acetone.…”

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confidence: 98%

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confidence: 98%

“…5,6) Antifungal and antiprotozoal activities of giganteosides D and E, major monodesmosides, have been evaluated.…”

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confidence: 99%

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Cytotoxic Triterpenoid Saponins from the Roots of Cephalaria gigantea

Tabatadze

Élias

Faure

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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The roots of Cephalaria gigantea (LEDEB.) BOBROV (Dipsacaceae), an endemic plant of Caucasus growing in Georgia, 1) contain a large amount of triterpene saponins. 2-4) The roots are well-known in traditional medicine as sedative and anti-inflammatory remedies.1) Previous works reported the identification of six triterpene glycosides. 5,6) Antifungal and antiprotozoal activities of giganteosides D and E, major monodesmosides, have been evaluated.7) The present paper describes isolation and structure elucidation of three new triterpene saponins, named giganteosides L (1), M (2) and N (3) from the roots of Cephalaria gigantea. Their structures were established on the basis of 2D-NMR experiments (gs-COSY, gs-HMQC, gs-HMBC and gs-HSQC-TOCSY) and mass spectrometry (MALDI-TOF, ESI-HR-MS). Saponins containing glucuronic acid in the sugar chain are reported for the first time in Cephalaria species. In addition, eight known triterpene glycosides, giganteosides D (4), 5) E (5), 5) G (6), 6) H (7), 6) I (8), 8) K (9), 8) J (10) 9,10) and J 1 (11) 9,10) were isolated from this plant.Dried root of C. gigantea was extracted with boiling 80% MeOH and after filtration the solution was evaporated. The solid residue was dissolved in methanol and precipitated in acetone. A combination of low pressure liquid chromatography and repeated silica gel column chromatography allowed the purification of eleven glycosides (1-11) including three new ones. The structures of the new saponins (1-3) were established on the basis of acid hydrolysis, NMR (Tables 1, 2)

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Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 98%

mentioning

confidence: 98%

“…5,6) Antifungal and antiprotozoal activities of giganteosides D and E, major monodesmosides, have been evaluated.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Cytotoxic Triterpenoid Saponins from the Roots of Cephalaria gigantea

Tabatadze

Élias

Faure

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Throughout the ages, many plants have been the basis of traditional medicines [2]. Cephalaria species have been used as folk medicine for many years due to their alleviative, anti-infective, hypothermic and relaxant activities [3,4]. The chemical constituents previously reported to be found in these plants were terpenoids, iridoids, flavonoids, alkaloids, and lignans [5 -18].…”

Section: Introductionmentioning

confidence: 99%

Glycosides from Cephalaria Species

Halay

Kirmizigul

2010

Zeitschrift Für Naturforschung B

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Three novel triterpene glycosides (1 - 3), namely lycicoside I, II and cilicicoside I, were isolated from two different Cephalaria (Dipsacaceae) species along with one known oleanane- and one iridoit- type of glycoside. The structures of these compounds were established as 3-O-[β -D-glucopyranosyl( 1→3)-α-L-rhamnopyranosyl(1→4)-β -D-xylopyranosyl(1→4)-β -D-xylopyranosyl]-28-O-[β -Dglucopyranosyl( 1→6)-β -D-glucopyranosyl]-oleanolic acid (1), 3-O-[β -D-xylopyranosyl(1→3)-α- L-rhamnopyranosyl(1→4)-β -D-xylopyranosyl]-28-O-[β -D-glucopyranosyl]-oleanolic acid (2) from Cephalaria lycica Matthew and 3-O-{β -D-glucopyranosyl(1→4)-β -D-xylopyranosyl(1→3)-α-Lrhamnopyranosyl( 1→2)-[β -D-glucopyranosyl(1→3)]-α -L-rhamnopyranosyl}-28-O-[β -D-glucopyranosyl( 1→6)-β -D-glucopyranosyl]-hederagenin (3) from Cephalaria cilicica Boiss. & Kotschy, on the basis of spectroscopic methods (1D and 2D NMR techniques, mass spectrometry) and chemical evidence. In addition, three new prosapogenins, 1B - 3B, were obtained from the basic hydrolysis of 1 - 3. The antimicrobial activity of 1 - 3 was tested against some Gram-positive and Gram-negative bacteria strains.

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