Triterpene glycosides of alfalfa VIII. Medinoside E from the leaves

From the leaves ofMedicago sativa L. (Leguminosae) we have isolated the glycoside soyasapogenol B — medinoside E. Medinoside E has the structure of olean-12-ene-3,22,24-triol 3-O-[O--L-rhamnopyranosyl-(12)-O--D-galactopyranosyl-(12)-O--D-glucopyranosyl-(12)--D-glucopyranuronoside].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. 705–710, September–October, 1993.     

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.     

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 ofHedera taurica XIV. Structures of glycosides St-G0–2, St-J, and St-K from the stems of Crimean ivy

The structures of new triterpene glycosides isolated from the stems of Crimean ivyHedera taurica Carr. (fam. Araliaceae) — St-J, St-K, and St-G_0–2 — have been established as the 3-0--L-glucopyranuronoside 28-O-[O-L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)--D-glucopyranoside]s of oleanolic acid and of hederagenin and the 3–0(6-O-ethyl--D-glucopyranuronoside) 28-O-[O-L-rhamnopyranosyl0(14)-O--D-glucopyranosyl-(16)-glucopyranoside of hederagenin, respectively.Simferopol' State University. Translated from Khimiya Prirodnykh Soedinenii No. 3, pp. 397–403, 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.     

Synthesis of bacterial antigenic polysaccharides and their fragments V. Use of 1,2-o-isopropylidene-4,6-O-ethylidene-α-D-galactopyranose for the synthesis of oligosaccharides with 3-o-substituted galactopyranose residue

Conclusions Trisaccharide-D-glucopyranosyl-(14)--L-rhamnopyranosyl-(1 3)-D-galactose was synthesized by using, 2-O-isopropylidene-4,6-O-ethylidene--D-galactopyranose for producing 1 3-rhamnosylgalactose, linkage.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1609–1613, July, 1977.     

A structural investigation of a D-glucan fromYersinia pseudotuberculosis of serotype VI

It has been established that an -D-glucan isolated fromYersinia pseudotuberculosis, serotype VI, is branched and contains -14- and -16-bound D-glucopy-ranose residues in the main chain and the side chains, respectively.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostock. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 151–154, March–April, 1981.     

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 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 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 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 ofCauliphyllum robustum. The structures of caulosides B and C

Summary Two triterpene glycosides — caulosides b and c — have been isolated from a methanolic extract of the leaves ofCaulophyllum robustum maxim. Cauloside b has been identified as hederagenin 3--L-rhamnopyranosyl-(12)--L-arabinopyranoside, while cauloside c has the structure of hederagenin 3-0--L-arabinopyranosyl(13)--L-pyranosyl-(12)--L-arabinopyranoside.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center of the Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 174–176, March–April, 1979.     

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.     

Steroid saponins and sapogenins ofAllium IX. The structure of aginoside

Summary From a methanolic extract of the skins of the bulbs ofAllium giganteum Rgl, a new steroid glycoside has been isolated — aginoside, which is (25R)-5-spirostan-2, 3, 6-triol 3-0-{[0--D-xylopyranosyl-(13)-]-[0--D-glucopyranosyl-(12)]-0--D-glucopyranosyl-(14)-0--D-galactopyranoside}.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 480–486, July–August, 1976.     

Transformed steroids. 121. Synthesis of the δ-lactone of 3β-acetoxy-16α-hydroxy-6-oxo-24-nor-5α-chol-17(20)-en-23-oic acid

The synthesis of the ¹⁷⁽²⁰⁾-16 analog of natural chiogralactone is described. Attempts to introduce a 6-oxo group directly into the -lactone proved unsuccessful, since the first stage — saponification — took place with the formation of three products: the 3-hydroxy--lactone, the 3-hydroxy-²⁰⁽²²⁾-lactone, and the 15,17(20)-dienoic acid. The synthesis of the desired compound was effected from the ethyl ester of the 5,16-dienoic acid by the scheme 3-acetate3-tosylate6-hydroxy-3,5-cyclosteroid6-oxo-3,5-cyclosteroid6-oxo-5H--lactone. It has been shown that the cyclopropane ring in the 3,5-cyclosteroid -lactone is extremely stable under the conditions of acid treatments.N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 184–187, March–April, 1981.     

The triterpene glycosides ofpatrinia intermedia roem et schult

Conclusions It has been established that patrinoside D₁ is the -D-glucopyranosido(13) -D-xylopyranosido(12) -L-rhamnosido(14)--D-xylopyranoside (13) of oleanolic acidKhimiya Prirodnykh Soedinenii, Vol. 5, No. 2, pp. 84–89, 1969     

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 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.     

Oxidative bromination of tricyclic sesquiterpenoids (1S,3S,5R,6S,9S)-5-hydroxy-6,10,10-trimethyl-tricyclo[7.2.0.01,6]udecan-2-one and clovane-2β,9α-diol with the HBr—DMSO system

Oxidation of tricyclic sesquiterpenoids of the caryophyllene type with the HBr—DMSO system afforded ,-unsaturated -bromoketones. Since tricyclic derivatives, unlike simple alicyclic ketones, cannot undergo aromatization, all intermediate oxidation products can be isolated, which provide evidence that oxidation proceeds according to the following scheme: ketone-bromoketone,-dibromoketone,-unsaturated -bromoketone.     

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.