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.     

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 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 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.     

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 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.     

Polysaccharides ofUngernia. VII. Partial hydrolysis of the mannan of the bulbs ofU. vvedenskyi

4-O--D-Manopyranosyl-D-mannose, O--D-mannopyranosyl-(l4)-O--D-mannopyranosyl-(14)-D-mannose, and 0--D-mannopyranosyl-(14)-O--D-mannopyranosyl-(l4)-O--D-mannopyranosyl-(l4)-D-mannose have been isolated fron the products of the partial hydrolysis of ungeromannan-V, obtained fron the bulbs ofUngernia vvedneskyi, and have been identified. This set of oligosaccharides confirms the regular structure of the carbohydrate chain of ungeromannan-V, which consists of a linear sequence of -14-bound D-mannose residues.DeceasedTranslated from Khimiya Prirodnykh Soedineii, No. 4, pp. 434–436, July–August, 1981.     

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 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.     

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 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 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 ofFatsia japonica. I. Isolation and structure of glycosides fromFatsia japonica seeds

The known triterpene glycosides hederagenin 3-O--L-arabinopyranoside, hederagenin 3-O-\-D-glucopyranoside, oleanolic acid 3-O--sophoroside, hederagenin 3-O--sophoroside, and their 28-O--gentiobiosyl esters, respectively, in addition to the new triterpene glycoside 3-O--sophorosyl-28-O--L-rhamnopyranosyl-(14)-O--gentiobiosyl hederagenin are isolated fromFatsia japonica (Araliaceae) seeds. The structures of these glycosides are established using chemical and spectral methods.Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 131–133, March–April, 2000.     

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 glycosides ofClimacoptera transoxana. III. The structures of copterosides E and F

New triterpene glycosides have been isolated from the epigeal part ofClimacoptera transoxana (Iljin) Botsch. — copterosides E and F. According to chemical transformations and physicochemical characteristics, copteroside E has the structure of oleanolic acid 28-O--D-glucopyranoside 3-O-{[O--D-xylopyranosyl-(12)]-[O--D-xylopyranosyl-(14)]--D-glucuronopyranoside} and copteroside F that that of hederagenin 28-O--D-glucopyranoside 3-O-{[O--D-xylopyranosyl-(12)]-[O--D-xylopyranosyl-(14)]--D-glucopyranoside}.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 596–601, September–October, 1983.     

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. 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.     

New glycosides from plants of the genus Phlojodicarpus

From plants of the genusPhlojodicarpus have been isolated the new coumarins umbelliferone -D-apiosyl (1 6)--D-glucopyranoside (I) and 8-(2,3-dihydroxy-3-methylbutyl)umbelliferone 7-O--D-glucopyranoside (II) and also the flavone glycoside diosmetin 7-O--D-glucopyranoside (III). The result of IR, UV, PMR, and¹³C NMR spectroscopy are given.Institute of Chemistry, Academy of Sciences of the Mongolian Peoples' Republic, Ulan-Bator; Irkutsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 36–39, January–February, 1986.