Triterpene glycosides from Kalopanax septemlobum. VI. Glycosides from leaves of Kalopanax septemlobum var. typicum introduced to crimea

Thirteen known glycosides of hederagenin and oleanolic acid and the three new triterpene glycosides of oleanolic acid-28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester 3-O-β-D-glucopyranosyl-(1→4)-O-β-D-xylopyranosyl-(1→ 3)-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranoside of oleanolic acid and the 28-O-α-L-rhamnopyranosyl-(1→4)-O-6-O-acetyl-β-D-glucopyranosyl-(1→ 6)-O-β-D-glucopyranosyl esters 3-O-β-D-xylopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranoside of oleanolic acid and 3-O-β-D-glucopyranosyl-(1→4)-O-β-Dxylopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→ 2)-O-α-L-arabinopyranoside of oleanolic acid were isolated from leaves of Kalopanax septemlobum var. typicum introduced to Crimea. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 40–43, January–February, 2006.     

Triterpene glycosides from <Emphasis Type="Italic">Lonicera</Emphasis>. Isolation and structural determination of seven glycosides from flower buds of <Emphasis Type="Italic">Lonicera macranthoides</Emphasis>

The structures of seven triterpene glycosides (1–7), of which the 23-O-acetyl, 28-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester of hederagenin 3-O-β-D-glucopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranoside (2) was new, from the flower buds of Lonicera macranthoides were established using chemical and NMR spectroscopic methods. Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 32–34, January–February, 2008.     

Triterpene glycosides of Hedera taurica VI. Structures of hederosides G,H1, H2, and I from the berries of Crimean ivy

We have isolated from Crimean ivy berries in addition previously known triterpene glycosides — 3-O-α-L-arabinopyranosyl-28-O-[O-α-L-rhamnopyranosyl-(1 → 4)-O-β-D-glycopyranosyl-(1 → 6)-β-D-glucopyranosyl]hederagenin, 3-O-[O-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl]-28-O-[O-α-L-rhamnopyranosyl-(1 → 4)-O-β-D-glucopyranosyl-(1 → 6)-β-D-glycopyranosyl]hederagenin, the new triterpene glycosides hederoside H₂-3-O-[O-β-D-glycopyranosyl-(1 → 2)-β-D-glycopyranosyl-(1 → 2)-β-D-glucopyranosyl]-28-O-[O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl]oleanolic acid- and hederoside I-3-O-[O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosyl]-28-O-[O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl]hederagenin. Details of their¹³C NMR spectra are given. M. V. Frunze Simferopol' State University. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 779–783, November–December, 1990.     

Triterpene glycosides ofHedera taurica. XI. Structures of taurosides St-G1, St-H1, and St-H2 from the stems of Crimean ivy

The previously known glycosides 3-O-α-L-arabinopyranosyl-28-O-[α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl]hederagenin and 3-O-[α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl]hederagenin and the new triterpene glycoside tauroside St-H₁ — 3-O-β-D-glucopyransyl-28-O-[α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl]hederagenin — have been isolated from the stems ofHedera taurica Carr. M. V. Frunze Simferopol' State University. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 571–579, July–August, 1993.     

Triterpene glycosides fromTupidanthus calyptratus I. Structure of glycosides B1, B2, F1, and F2 from leaves of hooded tupidanthus

Chromatographically inseparable mixtures of oleanolic and ursolic 3-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranosides (glycosides B₁ and B₂) and their 28-O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl esters (glycosides F₁ and F₂) are isolated from the leaves ofTupidanthus calyptratus Hook f. (Araliaceae). The structures of the isolated glycosides are established from chemical methods and¹H and¹³C NMR spectra. Glycoside F₂ is a new triterpene glycoside. Simferopol' State University. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 627–633, September–October, 1999.     

New polyhydroxysteroids and steroid glycosides from the far east starfishCeramaster patagonicus

Two new polyhydroxysteroids and five new glycosides were isolated from the starfishCeramaster patagonicus and their structures were elucidated: 5α-cholestane-3β,6α,15β,16β,26-pentol, (22E)-5α-cholest-22-ene-3β,6α,8,15α,24-pentol, (22E)-28-O-[O-(2-O-methyl-β-d-xylopyranosyl)-(1→2)-β-d-galactofuranosyl]-24-hydroxymethyl-5α-cholest-22-ene-3β,4β, 6α,8,15β,16β,28-heptol (ceramasteroside C₁), (22E)-28-O-[O-(2,4-di-O-methyl-β-d-xylopyranosyl)-(1→2)-β-d-galactofuranosyl]-24-hydroxymethyl-5α-cholest-22-ene-3β, 6α,8,15β,16β,28-hexol (ceramasteroside C₂), (22E)-28-O-[O-methyl-β-d-xylopyranosyl)-(1→2)-β-d-galactofuranosyl]-24-hydroxymethyl-5α-cholest-22-ene-3β,6α,8,15β,16β 28-hexol (eramasteroside C₃), (22E)-28-O-[O-(2-O-methyl-β-d-xylopyranosyl)-(1→2)-β-d-galactofuranosyl]-24-methyl-5α-cholest-22-ene-3β,4β,6α,8, 15β, 26-hexol (ceramasteroside C₄), and (22E)-28-O-[O-(2-O-methyl-β-d-xylopyranosyl)-(1→2)-β-d-xylopyranosyl]-5α-cholest-22-ene-3β,6α,8,15β,24-pentol (ceramasteroside C₅)). Three known polyhydroxysteroids (24-methylene-5α-cholestane-3β,6α,8,15β,16β,26-hexol, 5α-cholestane-3β,6α,8,15β,16β,26-hexol, and 5α-cholestane-3β,6β,15α,16β,26-pentol) were also isolated. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 190–195, January, 1997.     

Two new triterpenoid saponins from <Emphasis Type="Italic">Lysimachia davurica</Emphasis>

Two new saponins were isolated from an ethanol extract of the whole plants of Lysimachia davuria. The new saponins were respectively characterized as 3-O-{β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyl}-3β,28-dihydroxyolean-12-en-30-oic acid-O-[β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl]-ester (1) and 3-O-{ β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyl}-3β,28-dihydroxyolean-12-en-30-oic acid-O-β-D-glucopyranosyl-ester (2). Their structures were determined by 1D, 2D NMR and MS techniques. Published in Khimiya Prirodnykh Soedinenii, No. 5, pp. 466–468, September–October, 2007.     

Steroidal glycosides of gitogenin from Allium rotundum

Two new steroidal glycosides were isolated by fractionation of total extracted substances from inflorescences and flower stalks of Allium rotundum (Alliaceae). The structures were determined on the basis of chemical transformations, physical constants, and spectral data as 26-O-β-D-glucopyranosyl-(25R)-5α-furostan2α,3β,22α,26-tetraol 3-O-β-D-glucopyranosyl-(1 → 2)[β-D-xylopyranosyl-(1 → 3)]-β-D-glucopyranosyl(1 → 4)-β-D-galactopyranoside (2) and (25R)-5α-spirostan-2α,3β-diol 3-O-β-D-glucopyranosyl-(1 → 3)-βD-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 3)]-β-D-glucopyranosyl-(1 → 4)-β-D-galactopyranoside (3).     

Steroidal glycosides from Allium cyrillii bulbs

Two spirostanol saponins, one of which was a new compound, were isolated among the steroidal glycosides of Allium cyrillii Ten. Bulbs. The structures of these glycosides were established using chemical and spectral analytical methods as β-D-glycopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 3)]-β-D-glucopyranosyl-(1 → 4)β-D-galactopyranosyl-(1 → 3)-(25R)-5α-spirostan-2α,3β-diol and β-D-glucopyranosyl-(1 → 2)-[4-O-(3hydroxy-3-methylglutaryl)-β-D-xylopyranosyl-(1 → 3)]-β-D-glucopyranosyl-(1 → 4)-β-D-galactopyranosyl(1 → 3)-(25R)-5α-spirostan-2α,3β-diol.     

Cardiac glycosides from Strophanthus kombe

Twelve cardiac glycosides and aglycons were isolated from Strophanthus kombe seeds. Of these, eight were identified as cymarin, K-strophanthin-β, K-strophanthoside, periplocymarin, 17α-strophadogenin, erysimin (= helveticoside), erysimoside, and neoglucoerysimoside. Four glycosides, preliminarily designated Sk-x, Sk-y, Sk-z, and Sk-20, were new. Their chemical structures were established as 3β-O-β-D-glucopyranosyl-5β,14β,16β-trihydroxy-19-oxo-17α-card-20(22)enolide (17α-strophadogenin-3-O-β-D-glucoside), 3β-O-β-D-cymaropyranosyl-5β,14β,16β-trihydroxy-19-oxo-17α-card-20(22)enolide (17α-strophadogenin-3-O-β-D-cymaroside), 3β-O-β-D-cymaropyranosyl-4′-O-β-D-glucopyranosyl-6″-O-β-D-glucopyranosyl-5β, 14β,16β-trihydroxy-19-oxo-17α-card-20(22)enolide (17α-strophadogenin-3-O-strophanthotrioside), and 3-O-β-D-digitoxopyranosyl-4′-O-β-D-glucopyranosyl-6″-O-β-D-glucopyranosyl-5β,14β, 19-trihydroxy-card-20(22)enolide (strophanthidol-3-O-gentiobiosyldigitoxoside), respectively. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 156–159, March–April, 2006.     

Triterpene glycosides ofHedera canariensis III. Determination of the structures of glycosides L-F1, L-F2, and L-I2 from the leaves of Algerian ivy

The leaves of Algerian ivyHedera canariensis Willd. (Araliaceae) have yielded two new triterpene glycosides — caulophyllogenin 3-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranoside (L-F₂) and its 28-O-α-L-rhamnopyranosyl-(1→4)-O-β-D-gentiobiosyl ester (L-I₂) - and also the previously known hederagenin 3-O-α-L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranoside (L-F₁). The structures of the glycosides were established on the basis of chemical transformations and¹H and¹³C NMR spectroscopy. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 777–781, November–December, 1998.     

Triterpene Glycosides from <Emphasis Type="Italic">Cussonia paniculata</Emphasis>. II. Acetylated Glycosides from Leaves

Structures of 13 new acetylated triterpene glycosides from leaves of Cussonia paniculata (Araliaceae) were established as 28-O-(2-O-acetyl- and 3-O-acetyl-α-L-rhamnopyranosyl)-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β -D-glucopyranosides of 23-hydroxybetulinic acid (1a and 1b) and hederagenin (2a and 2b), 3-O-α-L-arabinopyranosyl-28-O-(2-O-acetyl- and 3-O-acetyl-a-L-rhamnopyranosyl)-(1→ 4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glycopyranosides of oleanic (3a and 3b) and ursolic (3c and 3d) acids, 3-O-α-L-arabinopyranosyl-28-O-(4-O-acetyl-, 2-O-acetyl-, and 3-O-acetyl-α-L-rhamnopyranosyl)-(1→4)-O-β-D-glucopyranosyl-(1→ 6)-O-β-D-glucopyranosides of hederagenin (4, d5a and 5b), and 3-O-β-D-glucopyranosyl-(1→2)-O-α-L-arabinopyranosyl-28-O-(2-O-acetyl- and 3-O-acetyl-α-L-rhamnopyranosyl)-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D- glucopyranosides of oleanic acid (6a and 6b). The structures of the compounds were established using chemical methods and NMR spectroscopy. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 351–356, July–August, 2005.     

Structure of a steroid saponin from <Emphasis Type="Italic">Digitalis ciliata</Emphasis>

A new steroid glycoside was isolated from leaves of Digitalis ciliata (Scrophulariaceae) by fractionation of the total extracted substances. Its structure was determined as (25R)-5α-spirostan-3β-ol 3-O-β-D-glucopyranosyl-(1→3)[β-D-fucopyranosyl-(1→2)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside based on chemical transformations, physical constants, and spectral data. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 135–137, March–April, 2007.     

Self-association and complexation of triterpene glycosides and cholesterol

Self-association of hederagenin 3-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranoside (α-hederin) and its 28-O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ether (hederacoside C) with cholesterol was studied using mass spectrometry (ESI MS). Possible complexation of the glycosides with cholesterol was examined. The ichtyotoxic activity of the glycosides and their mixtures with cholesterol to Barbus fefrozona was studied.     

Furostanol Glycosides from leaves of the Chinese plant <Emphasis Type="Italic">Tribulus terrestris</Emphasis>

The structures of five furostanol glycosides (1–5), of which the 26-O-β-D-glucopyranosyl-(25S),5α-furost20(22)-en-12-one-2α,3β,26-triol-3-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (1) was new, from the leaves of Tribulus terrestris L. were established using chemical and NMR spectroscopic methods.     

Triterpene glycosides ofHedera helix I. The structures of glycosides L-1, L-2a,L-2b,L-3, L-4a,L-4b,L-6a,L-6b,L-6c,L-7a,and L7-b from the leaves of common ivy

The leaves of common ivy have yielded 11 triterpene glycosides: the 3-O-α-L-pyranosides of oleanolic acid (1), of echinocystic acid (2), and of hederagenin; the 3-O-[O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside]s of oleanolic acid (4), of echinocystic acid (5), and of hederagenin (6); the O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester of hederagenin 3-O-α-L-pyranoside (7); the O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester of hederagenin 3-O-[O-α-L-pyranosyl-(1→2)-α-L-arabinopyranoside] (9); and the O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl esters of oleanolic acid, echinocystic acid, and hederagenin 3-O-[O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside]s (8), (10), and (11), respectively. This is the first time that compounds (1), (2), (5), (7), (9), and (10) have been found in this plant. Simferopol' State University. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 742–746, November–December, 1994.     

A new hederagenin glycoside from <Emphasis Type="Italic">Nephelium lappaceum</Emphasis>

A new oleane-type triterpene oligoglycoside, hederagenin 3-O-(3-O-acetyl-β-D-xylopyranosyl)-(1→3)-α-L-arabinopyranoside (2), together with four known compounds, hederagenin (1), hederagenin 3-O-(4-O-acetyl-α-L-arabinopyranosyl)-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside (3), hederagenin 3-O-α-L-arabinopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside (4), hederagenin 3-O-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→4)-β-D-xylopyranoside (5), was isolated from the hull of Nephelium lappaceum. All the isolates were obtained from the hull of rambutan for the first time.     

Triterpene glycosides ofHedera canariensis II. Determination of the structures of glycosides L-E2 and L-H3 from the leaves of Algerian ivy

The structures of two new triterpene glycosides, L-E₂ and L-H₃ from the leaves of Algerian ivyHedera canariensis Willd. (fam. Araliaceae), have been established on the basis of chemical and spectral characteristics: they are 30-norhederagenin 3-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranoside and the 28-O-α-L-rhamnopyranosyl-(1→4)-O-β-D-gentiobiosyl ester of 30-norhederagenin 3-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranoside, respectively. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 772–776, November–December, 1998.     

Triterpene glycosides fromHedera canariensis VI. Structure of L-G1 and L-G1b glycosides from leaves of canary ivy

Two new minor triterpene glycosides L-G₁, and L-G_2b, the 3-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1→4)-O-β-D-gentiobiosyl and 3-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1→4)-O-(6-O-acetyl-β-D-glucopyranosyl)-(1→6)-O-β-D glucopyranosyl esters of 30-norhederagenin, respectively, are isolated from the leaves of canary ivy (Hedera canariensis Willd.). The structures of the glycosides are found by chemical methods and¹H and¹³C NMR spectroscopy. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 623–626, September–October, 1999.     

Triterpene glycosides from Pulsatilla chinensis

Four triterpene glycosides were isolated from the roots of Pulsatilla chinensis (Bunge) Regel (Ranunculaceae). Two new glycosides, chinensiosides A (1a) and B (2), were identified as 3-O-[-L-rhamnopyranosyl-(12)--L-arabinopyranosyl]-28-O-[-L-rhamnopyranosyl-(14)--D-glucopyranosyl-(16)--D-glucopyranosyl]-3,23-dihydroxylup-20(29)-en-28-oic acid and 3-O-{-L-rhamnopyranosyl-(12)-[-D-glucopyranosyl-(14)]--L-arabinopyranosyl}-28-O-[-L-rhamnopyranosyl-(14)--D-glucopyranosyl-(16)--D-glucopyranosyl]-3,23-dihydroxylup-20(29)-en-28-oic acid. The other two glycosides were identified as previously known hederasaponin C (3) from Hedera helix and glycoside III (4) from Pulsatilla cernua.