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--L-pyranosides of oleanolic acid (1), of echinocystic acid (2), and of hederagenin; the 3-O-[O--L-rhamnopyranosyl-(12)--L-arabinopyranoside]s of oleanolic acid (4), of echinocystic acid (5), and of hederagenin (6); the O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl ester of hederagenin 3-O--L-pyranoside (7); the O--D-glucopyranosyl-(16)-O--D-glucopyranosyl ester of hederagenin 3-O-[O--L-pyranosyl-(12)--L-arabinopyranoside] (9); and the O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl esters of oleanolic acid, echinocystic acid, and hederagenin 3-O-[O--L-rhamnopyranosyl-(12)--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.     

Triterpene glycosides ofHedera helix II. Determination of the structure of glycoside L-6d from common ivy leaves

A new hederagenin pentaoside — glycoside L-6d — has been isolated from the leaves of common ivyHedera helix L., fam. Araliaceae, and its structure has been determined by using various NMR-spectroscopic methods. Glycoside L-6d is hederagenin 3-O-[O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside.     

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 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 ofHedera taurica I. Structure of tauroside E from the leaves ofHedera taurica

The structure of taurorisde E — the predominating triterpene glycoside from the leaves of Crimean ivy,Hedera taurica Carr. has been established by¹H and¹³C NMR spectroscopy using nuclear Overhauser effects. It is 3-O-[O--L-rhamnopyranosyl-(12)--L-arabinopyranosyl]hederagenin.M. V. Frunze Simferopol' State University. Translated from Khimiya Prirodnykh Soedenenii, No. 3, pp. 363–366, May–June, 1987.     

Triterpene glycosides ofHedera canariensis. V. Structure of glycosides from canary ivy stems

Triterpene glycosides from leaves of canary ivyHedera canariensis Willd. were previously isolated and characterized [1–4]. The glycosidic composition of the plant stems is reported in the present article. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 676–678, September–October, 1999.     

Triterpene glycosides ofHedera canariensis IV. Structures of glycosides L-F3, L-G0, and L-Gla from the leaves of Algerian ivy

Three minor partially acetylated glycosides have been isolated from the leaves of Algerian ivy, Hedera canariensis Willd. (Araliaceae) — the previously known {3-O-[-L-rhamnopyranosyl-(12)-O--L-arabinopyranoside] 28-O-[-L-rhamnopyranosyl-(14)-O-(6-acetyl--D-glucopyranosyl)-(16)-O--D-glucopyranoside}s of oleanolic acid and of hederagenin (ciwujianoside C₄ and kizuta saponin K₁₁) and the new 3-O-[-L-rhamnopyranosyl-(12)--O-L-arabinopyranoside] 28-O-[-L-rhamnopyranosyl-(14)-O-(6-O-acetyl--D-glucopyranosyl)-(16)-O--D-glucopyranoside of echinocystic acid (glycoside L-G₀). The structures of the glycosides isolated have been established on the basis of chemical transformations and¹H and¹³C NMR spectroscopy.Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 81–86, January–February, 1999.     

Triterpene glycosides ofHedera taurica XV. Structures of glycosides St-I3, St-I4a, St-I4b, and St-I5 from the stems of Crimean ivy

From the stems of Crimean ivyHedera taurica Carr. (fam. Araliaceae) we have isolated the new triterpene glycosides St-I₃, St-I₅, and St-I_4a, which are, respectively, the 3–0--D-glucopyranoside 28-O-[O--L-rhamnopyranosyl-(14)-O-(6-O-acetyl--D-glucopyranosyl)-(16)-O--D-glucopyranosides] of oleanolic acid and of hederagenin and the 3-O--D-glucopyranuronoside 28-O--gentiobioside of oleanolic acid, and also the previously known 3-O-[O--D-galactopyranosyl-(12)--D-glucopyranuronoside 28-O--D-glucopyranoside] of oleanolic acid (glycoside Rb-4).Simferopol' State University. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 404–410, May–June, 1997.     

Triterpene glycosides ofHedera helix II. Determination of the structure of glycoside L-6d from common ivy leaves

A new hederagenin pentaoside — glycoside L-6d — has been isolated from the leaves of common ivyHedera helix L., fam. Araliaceae, and its structure has been determined by using various NMR-spectroscopic methods. Glycoside L-6d is hederagenin 3-O-[O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl-(14)-O--L-rhamnopyranosyl-(12)--L-arabinopyranoside.Simferopol' State University. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 746–752, November–December, 1994.     

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 Cussonia paniculata. III. Structure of glycosides I1, I2, J1a, J1b, J2, K, L1, and L2 from C. paniculata leaves

Structures of eight triterpene glycosides, of which the 28-O-(2-O-acetyl-and 3-O-acetyl-α-L-rhamnopyranosyl)-(1→4)-O-β-D-glucopyranosyl-(1→ 6)-O-β-D-glucopyranosyl esters of hederagenin 3-O-β-D-glucopyranosyl-(1→ 2)-O-α-L-arabinopyranoside (J_1a and J_1b) were new, from Cussonia paniculata (Araliaceae) leaves were established using chemical and NMR spectroscopic methods. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 149–152, March–April, 2006.     

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 ofHedera taurica II. Structures of taurosides St-G0–1, St-G2, and St-G3 from the stems of Crimean ivy

Simferopol' State University. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 826–828, November–December, 1994.     

Triterpene glycosides ofHedera canariensis. I. Structures of glycosides L-A,L-B1, L-B2, L-C,L-D,L-E1 1, L-G1, L-G2, L-G3, L-G4, L-H1, L-H2, AND L-I1 from the leaves ofHedera canariensis

From the leaves of Algerian ivyHedera canariensis Willd. (fam. Aralaceae) we have isolated 13 triterpene glycosides: the 3-O--L-arabinopyranosides of oleanolic acid (A), of echinocystic acid (B₁), and of hederagenin (B₂); the 3-O-[O--L-rhamnopyranosyl-(2)--L-arabinopyranoside]s of oleanolic acid (C), of echinocystic acid (D), and of hederagenin (E₁); the 3-O--L-rhamnopyranoside] 28-O-[O--L-rhamnopyranosyl-(14)--gentiobioside of hederagenin (G₁); the 3-O-[O--L-rhamnopyranosyl-(12)--L-arabinopyranoside] 28-O--gentiobioside of hederagenin (G3); the 3-O-[O--L-rhamnopyranosyl-(12)--L-arabinopyranoside] 28-O-[O--L-rhamnopyranosyl-(14)--gentiobioside]s of oleanolic acid (G₂), of echinocystic acid (H₁), and of hederagenin (H₂); the 3-O-[O--L-rhanmopyranosyl-(12)--D-glucopyranoside] 28-O-(O--L-rhamno-pyranosyl-(14)--gentiobioside] of hederagenin (H₂); and the 3-O-(O--L-rhamnopyranosyl-(12)-O-gentiobiosyl)-O-(14)--L-rhamnopyranosyl-(12)-a-L-arabinopyranoside] of hederagenin (G₄). The structures of the substances isolated have been established on the basis of chemical transformations and¹³C NMR spectroscopy.Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 377–383, May–June, 1996. Original article submitted December 3, 1995.     

Triterpene glycosides of Hedera taurica X. Structures of compounds F4, I,and J from the leaves of Crimean ivy

Echinocystic acid 3-sulfate and new 3-sulfates — of the 28-O-[O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl esters of oleanolic and echinocystic acids have been isolated from the leaves of Crimean ivyHedera taurica Carr. (fam. Araliaceae).     

Triterpene glycosides ofHedera taurica XVI. Structures of glycosides St-A, St-B1, St-B2, St-C, St-D1, St-D2, St-E, St-F1, and St-F2 from the stems of Crimean ivy

From the stems of Crimean ivyHedera taurica Carr. (fam. Araliaceae) we have isolated previously known glycosides of oleanolic acid — the 3-O-[O--L-rhamnopyranosyl-(12)--L-arabinopyranoside], the 3-O--D-glucopyranuronoside, and the 3-O-[O--D-galactopyranosyl-(12)--D-glucopyranuronoside]; known glycosides of hederagenin — the 3-O--L-arabinopyranoside, the 3--D-glucopyranoside, the 3-O-[O--D-glucopyranosyl-(12)-O--L-arabinopyranoside], and the 3-O--D-glucopyranuronoside; and also the new triterpene glycoside St-D₂, hederagenin 3-O-[O--L-rhamnopyranosyl-(12)--D-glucopyranoside].Simferopol' State University. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 411–416, May–June, 1997.     

Triterpene glycosides of Hedera taurica X. Structures of compounds F4, I, and J from the leaves of Crimean ivy

Echinocystic acid 3-sulfate and new 3-sulfates — of the 28-O-[O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)--D-glucopyranosyl esters of oleanolic and echinocystic acids have been isolated from the leaves of Crimean ivyHedera taurica Carr. (fam. Araliaceae).M. P. Frunze Simferopol' State University. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 683–686, November–December, 1992.     

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.     

Triterpene glycosides from the bark of Robinia pseudo-acacia L. I.

From the bark of Robinia pseudo-acacia L., five new triterpene glycosides, robiniosides A-D (3, 5-7) and compound III (4), were isolated and their structures were elucidated as 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl(1-->2)-beta-D- glucuronopyranosyl 3 beta,22 beta-dihydroxyolean-12-en-29-oic acid (3), 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-galactopyranosyl(1-->2)-beta-D -glucuronopyranosyl 3 beta,22 beta,24-trihydroxyolean-12-en-29-oic acid (4), whose sapogenol was unambiguously characterized and designated as oxytrogenin, 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl(1-->2)-beta-D glucuronopyranosyl oxytrogen (5), 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D galactopyranosyl(1-->2)-beta-D-glucuronopyranosyl oxytrogenin 22-O-alpha-L-rhamnopyranoside (6), 3-O-alpha-L- rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl(1-->2)-beta-D-glucuronop yranosyl oxytrogenin 22-O-alpha-L-rhamnopyranoside (7), respectively, together with two known triterpene glycosides, kaikasaponin III (1) and 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-galactopyranosyl(1-->2)-beta-D - glucuronopyranosyl 3 beta,22 beta-dihydroxyolean-12-en-29-oic acid (2).     

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.