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 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 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 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 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.     

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.     

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 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 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 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 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 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     

Steroid glycosides ofNicotiana tabacum seeds I. The structures of nicotianosides A, B, and E

Two steroid glycosides of the spirostan series — nicotianosides A and B — and one glycoside of the furostan series — nicotianoside E — have been isolated from the seeds ofNicotiana tabacum L. Nicotianoside A is (25S)-5-spirostan-3-ol 3-O--D-glucopyranoside, nicotianoside B is (25S)-5-spirostan-3-ol 3-O-[O--L-rhamnopyranosyl-(12)-gb-D-glucopyranoside], and nicotianoside E is (25S)-5-furostan-3,22,26-triol 26-O--glucopyranoside 3-O-[O--L-rhamnopyranosyl-(12)--D-glucopyranoside].Institute of Genetics, Academy of Sciences of the Republic of Moldava, Kishinev, ul. Lesnaya, 20. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 737–742, 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. 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 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 ofSophora japonica seeds

We have isolated from the seeds of Sophora japonica the known soyasaponogenol B-3-[O--D-glucopyranosyl-(12)-O--D-glucopyranuronoside] (adzukisaponin II), soyasapogenol B [3-O--galactopyranosyl-(12)-O--L-glucopyranuronoside] (soyasaponin III), soyasapogenol B 3-(O--L-rhamnopyranosyl-(12)-O--L-glucopyranosyl-(12)-O--D-glucopyranuronoside] (adzukisaponin V), soyasapogenol B 3-(O--D-rhamnopyranosyl-(12)-O--D-galactopyranosyl-(12)-O--D-glucopyranuronoside] (soyasaponin I), and the new glycoside (1) — soyasapogenol B 3-[O--D-glucopyranuronoside]. The structure of this glycoside has been established on the basis of the results of enzymatic, complete, and partial hydrolyses and¹³C NMR spectra.Simferopol' State University and Kursk State Medical Institute, Kursk. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 709–713, September–October, 1995. Original submitted March 3, 1995.     

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 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. IV. Medicoside J

A new triterpene glycoside has been isolated from the roots ofMedicago sativa L. (family Fabaceae) — medicoside J, and its structure has been established as a medicagenic acid 3-O--D-glucopyranoside 28-O-[O--D-xylopyranosyl-(1 4)-O--L-rhamnopyranosyl-(1 2)--L-arabinopyranoside].Institute of the Chemistry of Plant Substances of the Uzbek Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 610–613, September–December, 1986.