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 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 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 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.     

Triterpenoid Glycosides of Fatsia japonica. II. Isolation and Structure of Glycosides from the Leaves

The previously known triterpenoid 3-O--L-arabinopyranosides of oleanolic and echinocystic acids and hederagenin, 3-O--D-glucopyranosyl-(12)-O--L-arabinopyranosides of oleanolic acid and hederagenin, in addition to 28-O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl ethers of the 3-O--L-arabinopyranoside of hederagenin, and 3-O--D-glucopyranosyl-(12)-O--L-arabinopyranosides of oleanolic acid and hederagenin, respectively, are isolated from leaves ofFatsia japonica(Araliaceae). The structures of the glycosides are confirmed by chemical methods and ¹³ C NMR spectroscopy     

Triterpene Glycosides of Tetrapanax papyriferum. II. Isolation and Structure Determination of Glycosides St-E2, St-F2, St-J2, and St-K2 from Stem Bark

Stem bark ofTetrapanaxpapyriferum yielded the new triterpene glycosides 3-O-[-D-glucopyranosyl-(13)]--D-galactopyranosyl-(12)-O--L-arabinopyranosides of oleanolic and echinocystic acids and their 28-O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl esters. Their structures were established using chemical and physicochemical methods     

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 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 of Tetrapanax papyriferum. I. Isolation and Structure of Glycosides St-H2 and St-I2 from Stem Bark

Stem bark ofTetrapanax papyriferumC. Koch., Araliaceae, yielded new triterpene glycosides 28-O--L-rhamnopyranosyl-(14)-O-(6-O-acetyl--D-glucopyranosyl)-(16)-O--D-glucopyranosyl esters of the 3-O-[-D-glucopyranosyl-(13)-[-D-galactopyranosyl-(12)]-O--L-arabinopyranosides of oleanolic and echinocystic acids. The structures of these substances were established using chemical and physicochemical methods     

Arjunolic acid derivative glycoside from the stems of <Emphasis Type="Italic">Hedera colchica</Emphasis>

Five triterpenoid saponins were isolated from the stems of Hedera colchica K. Koch, Araliaceae. Two of them are new natural substances. HCSt-A (1): 3-O--D-arabinopyranoside; 28-O--L-rhamnopyranosyl-(1 4)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl-arjunolic acid. HCSt-B (2): 3-O--D-xylopyranoside; 28-O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl-hederagenin. The derivative of arjunolic acid is described for the first time in Araliaceae family. The chemical structures of isolated compounds were established on the base of chemical and 1D and 2D NMR experiments.Published in Khimiya Prirodnykh Soedinenii, No. 6, pp. 461–463, November–December, 2004.This revised version was published online in April 2005 with a corrected cover date.     

Triterpene glycosides ofPatrinia scabiosofolia. I

Conclusions From the fraction of the feebly polar saponins ofPatrinia scabiosofolia Fisch. et Link oleanolic acid, hederagenin, -sitosterol, -D-glucopyranoside, and hederagenin 3--L-arabopyranoside have been isolated.The polar fraction has yielded two triterpene glycosides. It has been established that one of them is oleanolic acid 3-O--D-glucopyranosyl-(1 4)--L-arabinopyranoside, and the other is hederagenin 3-O--D-glucopyranosyl-(1 4)--L-arabopyranoside.Khimiya Prirodnykh Soedinenii, Vol. 6, No. 1, pp. 69–74, 1970     

Triterpene Glycosides of Fatsia japonica. IV. Structure of Glycosides D1 and D2 from Seeds

Seeds ofFatsia japonica(Araliaceae) afforded the known hederagenin 3-O--D-glucopyranosyl-(12)-O--L-arabinopyranoside and the new triterpene glycoside D ₂ , for which the structure hederagenin 3-O--D- galactopyranosyl-(12)-O--L-arabinopyranoside was proposed based on chemical methods and NMR spectroscopy     

Triterpene glycosides and their genins fromThalictrum foetidum. I. The structure of foetoside C

A new glycoside — foetoside C — has been isolated from the epigeal part ofThalictrum foetidum L. and, on the basis of chemical transformations and spectral characteristics its structure has been established as oleanolic acid 28-[O--D-glycopyranosyl-(1 6)-O--D-glucopyranoside] 3-O-[O--D-xylopyranosyl-(1 3)-O--L-rhamnopyranosyl-(1 2)--L-arabinopyranoside].Irkutsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 458–463, July–August, 1984.     

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.     

The structure of yuccoside E from Yucca filamentosa

Summary From the roots ofYucca filamentosa L. we have isolated a new sarsasapogenin glycoside, yuccoside E, which is 3-O-{[O--D-galactopyranosyl(1 2)]-[-O--D-galactopyranosyl(1 6)]-O--D-glucopyranosyl-(1 4)--D-glucopyranosyl}-(25S), 5 -spirostan-3-ol.Institute of Chemistry, Academy of Sciences of the Moldavian SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 747–750, November–December, 1975.     

Structure of codonoside B

On the basis of chemical transformations and physicochemical characteristics of the compounds obtained it has been established that codonoside B — the main triterpene glycoside ofCodonopsis lanceolata (Sieb. et Zucc.) Benth. et Hook., has the structure of echinocystic acid 3-O--D-glucopyranuronoside 28-O-[O--D-xylopyranosyl-(1 4)-O--L-rhamnopyranosyl-(1 4)-O--D-glucopyranosyl-(1 2)--L-arabinopyranoside].Far Eastern State University, Vladivostok. Pacific Ocean Institute of Organic Chemistry, Far Eastern Branch, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 368–372, May–June, 1989.     

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 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 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 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.