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.     

Oligosaccharides ofSaponaria officinalis

Conclusions It has been found that the roots ofSaponaria officinalis L. contain three oligosaccharides.Two of them have been isolated: gentiobiose and the pentasaccharide saponarose. It has been shown that the latter is O--D-galactopyranosyl-(1 3)-O--D-galactopyranosyl-(1 3)-O--D-galactopyranosyl-(1 3)-O--D-galactopyranosyl-(1 1)--D-glucopyranoside.Khimiya Prirodnykh Soedinenii, Vol. 5, No. 6, pp. 469–473, 1969     

Triterpene glycosides of Pulsatilla dahurica structures of glycosides A,B, C,and D

The isolation of four triterpene glycosides from the roots of the dahurian anemonePulsatilla dahurica (Fisch. ex DC) Spreng, is described together with their identification, on the basis of chemical transformations, spectral characteristics, and literature analogies, as hederagenin 3-O--L-arabinoside, hederagenin 3-O-[O--D-glucopyranosyl-(12)--L-arabinopyranoside], hederagenin 3-O--L-arabinopyranoside 28-O-[O--L-rhamnopyranosyl-(14)--D-glucopyranosyl-(16)--D-glucopyranoside], and hederagenin 3-O-[O--D-glucopyranosyl-(14)--L-arabinopyranoside] 28-O-[O--L-rhamnopyranosyl-(14)--D-glucopyranosyl-(16)--D-glucopyranoside].Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, Nos. 3,4, pp. 349–356, May–August, 1992.     

Triterpene glycosides ofLeontice eversmannii

Conclusions The structure of leontoside D-a hederagenin pentaoside-has been established. The O-glycosidic moiety of leontoside D is O--D-glucopyranosido-(1 4)-O--L-arabopyranose, and the O-acyl moiety is O--L-rhamnopyranosido-(1 4)-O--D-glucopyranosido-(1 6)-O--D-glucopyranose.Khimiya Prirodnykh Soedinenii, Vol. 4, No. 3, pp. 153–158, 1968     

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 of Hedera pastuchovii IV. The structure of pastuchoside B

Summary Pastuchoside B has been isolated and shown to be O--D-glycopyranosyl-(1 4)-O--D-glucopyranosyl-(1 3)-hederagenin.N. Narimanov Azerbaidzhan Medical Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 425–429, July–August, 1971.     

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 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--L-arabinopyranosyl-28-O-[-L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl]hederagenin and 3-O-[-L-rhamnopyranosyl-(12)-O--L-arabinopyranosyl]-28-O-[-L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl]hederagenin and the new triterpene glycoside tauroside St-H₁ — 3-O--D-glucopyransyl-28-O-[-L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--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 saponins fromThalictrum minus. V. Structure of thalicoside B

The epigeal part ofThalictrum minus L. has yielded a new bidesmoside — thalicoside B — which has the structure of oleanolic acid 28-O--D-glucopyranoside 3-O-[O--L-rhamnopyranosyl-(1 2)-O--D-glucopyranosyl-(1 3)--L-arabinopyranoside].Irkutsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR; A. A. Zhdanov Irkutsk State University; and Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 670–676, September–October, 1985.     

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--L-arabinopyranosyl-28-O-[O--L-rhamnopyranosyl-(1 4)-O--D-glycopyranosyl-(1 6)--D-glucopyranosyl]hederagenin, 3-O-[O--L-rhamnopyranosyl-(1 2)--L-arabinopyranosyl]-28-O-[O--L-rhamnopyranosyl-(1 4)-O--D-glucopyranosyl-(1 6)--D-glycopyranosyl]hederagenin, the new triterpene glycosides hederoside H₂-3-O-[O--D-glycopyranosyl-(1 2)--D-glycopyranosyl-(1 2)--D-glucopyranosyl]-28-O-[O--D-glucopyranosyl-(1 6)--D-glucopyranosyl]oleanolic acid- and hederoside I-3-O-[O--D-glucopyranosyl-(1 2)--D-glucopyranosyl]-28-O-[O--D-glucopyranosyl-(1 6)--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 of Hedera taurica

From the leaves of Crimean ivy we have isolated the previously known glycosides 3-O--L-Ara_p-28-O-[O--L-Rha_p-(14)-O--D-Glc_p-(16)--D-Glc_p]hederagenin, 3-O-[O--L-Rha_p-(12)--L-Ara_p]-28-O-[O--L-Rha_p-(14)-O--D-Glc_p-(16)--D-Glc_p]oleanic acid and -hederagenin, and 3-O-[O--L-Rha_p-(12)--L-Ara_p]-28-O-[O--D-Glc_p-(16)--D-Glc_p]hederagenin and a new one: tauroside H₁ — 3-O-[O--L-Rha_p-(12)-O--L-Ara_p]-28-O-[O--L-Rha_p-(14)-O--D-Glc_p-(16)--D-Glc_p]echinocystic acid.M. V. Frunze Simferopol' State University. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 522–528, September–October, 1992.     

Triterpene and steroid glycosides of the genusMelilotus and their genins II. Melilotoside D from the roots ofMelilotus albus

A new triterpene glycoside of the oleanane series — melilotoside D — has been isolated from the roots of plantMelilotus albus Medik. (Leguminosae). Melilotoside D is a tetraoside of soyasapogenol B. Its structure has been shown on the basis of chemical transformations and spectral characteristics as soyasapogenol B 3-O-{[O--L-rhamnopyranosyl-(12)]-[O--L-arabinopyranosyl-(13)]-O--D-galactopyranosyl-(12)--L-arabinopyranoside}.Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 762–765, 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 saponins of Caltha polypetala. Glycosides G and I

From the epigeal organs of the great march marigold (family Ranunculaceae) two triterpene glycosides, a tetra- and a pentaoside of hederagenin, have been isolated. Their chemical structures have been established by chemical methods of investigation and by¹H and¹³C NMR spectroscopy. Glycoside G is hederagenin 3-O--L-arabinoside 28-O-[O--L-rhamnopyranosyl-(1 4)-O--D-glucopyranosyl-(1 6)--D-glucopyranoside]. Glycoside I is hederagenin 3-O-[O--D-glucopyranosyl-(1 2)--L-arabinoside 28-O-[O--L-rhamnopyranosyl-(1 4)-O--D-glucopyranosyl-(1 6)--D-glucopyranoside].I. G. Kutateladze Institute of Pharmacochemistry, Georgian SSR Academy of Sciences, Tbilisi, Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 229–236, March–April, 1988.     

Triterpene and steroid glycosides of theMelilotus genus and their genins I. Melilotosides A, B, and C from the roots ofMelilotus albus

Three new triterpene glycosides of the oleanane series — melilotosides A, B, and C — and the nonglycosylated soyasapogenol B have been isolated from the roots of the plant Melilotus albus Medik. (Leguminosae). The structures of the glycosides have been shown on the basis of chemical transformations and spectral results. Melilotoside A has the structure of soyasapogenol B 3-O--L-arabinopyranoside, melilotoside B that of soyasapogenol B 3-O-[O--D-galactopyranosyl-(12)--L-arabinopyranoside], and melilotoside C that of soyasapogenol B 3-O-[O--L-rhamnopyranosyl-(12)-O--D-galactopyranosyl-(12)--L-arabinopyranoside.Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 756–762, November–December, 1994.     

Triterpene glycosides ofPatrinia scabiosofolia; II

Conclusions The triterpene glycosides scabiosides D, E, F, and G have been isolated from the roots ofPatrinia scabiosofolia Fisch. et Link. It has been established that scabioside D is O--D-glucopyranosyl-(1 4)-O--L-arabopyranosyl-(1 3)-O-oleanoloyl-(28 1)--D-xylopyranose, and scabioside E is O--D-glucopyranosyl-(1 4)-O--L-arabopyranosyl-(1 3)-O-oleanoloyl-(28 1)-O--D-xylopyranosyl-(4 1)--L-rhamnopyranose.     

Triterpene glycosides ofSapindus mukorossi

Conclusions The structure of two triterpone glycosides fromSapindus mukorossi Gaertn. has been established. It has been shown that sapindoside A is hederagenin 3-O--L-arabinosyl-(2 1)--L-rhamnopyranoside and sapindoside B is the 3-O--L-arabopyranosyl-(2 1)-O--L-rhamnopyranosyl-(3 1)--D-xylopyranoside.     

Triterpene glycosides of alfalfa. VI. Medicoside L

A new triterpene pentaglycoside — medicoside L — has been isolated from the roots ofMedicago sativa L. (Leguminosae). It has the structure of medicagenic acid 28-O--D-glucopyranoside 3-O-{[O--D-glucopyranosyl-(1 2)][O--L-rhamnopyranosyl-(1 3)]-O--D-glucopyranosyl-(1 2)}--D-glucopyranoside.Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 221–228, March–April, 1990.     

Tripenoid glycosides of alfalfa. VII. Medicosides E and F

Two hederagenin glycosides — medicosides E and F — have been isolated from the roots ofMedicago sativa L. (Leguminosae). Medicoside E has the structure of hederagenin 28-O--D-glucopyranoside 3-O-[O--G-glucopyranosyl-(13)--D-xylopyranoside]. Medicoside F has the structure of hederagenin 28-O--D-glucopyranoside 3-O-[O--D-glucopyranosyl-(12)--L-arabinopyranoside].Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent. Institute of Organic Chemistry, Russian Academy of Sciences, Moscow. Translated from Khimiya Prirodnykh Soedinenii. No. 5, pp. 701–705, September–October, 1993.     

Steroid glycosides of the leaves of Yucca aloifolia

Two new steroid glycosides have been isolated from the leaves of aloe yucca and their structures have been established. Glycosides B and C are tigogenin penta-and hexaosides. Glycoside B, which we have called yuccaloeside B is (25R)-5-spirostan-3-ol 3-{[O--D-glucopyranosyl-(12)]-[O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(13)]-O--D-glucopyranosyl-(14)--D-galactopyranoside}, and glycoside C, which we have called yuccaloeside C is (25R)-5-spirostan-3-ol 3-{[(O--D-glucopyranosyl-(13)-O--D-glucopyranosyl-(12)]-[O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(13)]-O--D-glucopyranosyl-(14)--D-galactopyranoside}.N. G. Kutateladze Institute of Pharmacochemistry of the Georgian SSR Academy of Sciences, Tbilisi. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 537–542, July–August, 1987.