Triterpene Glycosides of Fatsia japonica. VI. Structures of Glycosides D3a and D3b

Seeds of Fatsia japonica (Araliaceae) yielded the new glycosides of gypsogenin: 3-O--D-glucopyranosyl-(12)-O--D-glucopyranoside and 3-O--D-galactopyranosyl-(12)-O--D-glucopyranoside. The structures of these compounds were established by chemical methods and NMR spectroscopy.     

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 Tragacantha stipulosa and Their Genins. Structure of Cyclostipuloside E

The known compound trojanoside A (1) and a new cycloartane glycoside cyclostipuloside E (2) were isolated from the aerial parts of Tragacantha stipulosa Boriss. The structure of cyclostipuloside E was proposed as 24R-cycloartan-3,6,16,24,25-pentaol 6,16,25-tri-O--D-glucopyranoside 3-O--D-xylopyranoside based.     

Triterpene glycosides ofAstragalus and their genins. XV. Cyclosiversiosides B and D fromAstragalus basineri

Two new glycosides have been isolated from the roots of the plantAstragalus basineri Trautv. — cyclosiversiosides B and D. It has been shown that cyclosiversioside B is cyclosiversigenin 3-O-(2,3-di-O-acetyl--D-xylopyranoside)-6-O--D-glucopyranoside. Cyclosiversioside D is cyclosiversigenin 3-O-(2-O-acetyl--D-xylopyranoside)-6-O--D-glucopyranoside.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 188–191, March–April, 1984.     

Triterpene glycosides ofAstragalus and their genins XLV. The chemical transformation of cycloartanes 1. Synthesis of 25-norglycosides

Literature information is given on the current state of the study of the chemical transformation of cycloartane triterpenoids. A method has been developed for the transformation of the genin part of glycosides of 20,24-epoxycycloartan-25-ols with retention of the carbohydrate constituents. Three 25-norglycosides have been synthesized from natural cyclosieversigenin glycosides, namely 16-acetoxy-3,6-dihydroxy-20R,25-norcycloartan-20,24-olide 3-O-[O--L-arabinopyranosyl-(12)--D-xylopyranoside] 6-O--D-xylopyranoside (VIII), sodium 3,6,16,20-tetrahydroxy-20R,25-norcycloartan-24-oate 6-O--D-glucopyranoside 3-O--D-xylopyranoside (XII), and 20R,25-norcycloartane-3,6,16,20,24-pentaol 6-O--D-glucopyranoside 3-O--D-xylopyranoside (XIII).Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 710–718, September–October, 1993.     

Steroids of the furostan and spirostan series from Nolina microcarpa II. structures of nolinospiroside D and nolinofurosides D, E, and F

Proofs are given of the structures of two new glycosides of the furostan series isolated from the leaves of the plantNolina microscarpa S. Wats. (family Dracaenaceae). Nolinofuroside D is (25S)-furost-5-ene-1,3,22,26-tetraol 1-O--D-galactopyranoside 26-O--D-glucopyranoside (I), and nolinofuroside F is (25S)-furost-5-ene-1,3,22,26-tetraol 1-O--D-fucopyranoside 26-O--D-glucopyranoside 3-O--L-rhamnopyranoside (VII). The latter was characterized as its 22-O-methyl ether (VIII). Nolinofuroside E (IV) has the structure of (25S)-furost-5-ene-1,3,22,26-tetraol 26-O--glucopyranoside 1-O-[O--L-rhamnopyranosyl-(12)--D-fucopyranoside], which followed from the structure of the fermentation product (VI). The products of the fermentation of the above-named compounds were present in the plant in only trace amounts. Only one of them — nolinospiroside D (III) — has not been described previously. This monoside of the spirostan series is (25S)-spirost-5-ene-1,3-diol 1-O--D-galactopyranoside.M. V. Frunze Simferopol' State University. Institute of Chemistry of Plant Substances, Uzbek Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 678–686, September–October, 1991.     

Triterpene Glycosides from Plants of the Astragalus Genus. Structure of Cyclounifolioside A from Astragalus unifoliolatus

The known compound oleanolic acid (1) and a new cycloartane glycoside cyclounifolioside A (2), which has the structure 6,16-di-O-acetyl-24R-cycloartan-6,16,24,25-pentaol 3-O--D-glucopyranoside, were isolated from Astragalus unifoliolatus Bunge. The structures of the isolated compounds were established using chemical transformations and two-dimensional spectra (TOCSY, ROESY, HMBC, HSQC, COSY).     

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.     

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.     

Steroids of the spirostan and furostan series from Nolina microcarpa I. Structures of nolinospiroside C and nolinofurosides A and C

In addition to the know steroid sapogenin (25S)-ruscogenin (I), three new glycosides have been isolated from the leaves ofNolina microcarpa S. Wats. (family Dracaenacea), and the following structures are suggested for them: (25S)-spirost-5-ene-1,3-diol 1-O--D-fucopyranoside (nolinospiroside C, II), (25S)-furost-5-ene-1,3,22,26-tetraol 1-O--D-fucopyranoside (nolinofuroside A, III), and (25S)-furost-5-ene-1, 3, 22, 26-tetraol 1-O--D-fucopyranoside 26-O--D-glucopyranoside (nolinofuroside C, V).M. V. Frunze Simferopol' State University. Institute of Chemistry of Plant Substances, Uzbek Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 672–678, September–October, 1991.     

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.     

Steroids of the spirostan and furostan series from plants of the genus Allium. XXVII. Alliosterol and allosides A and B from Allium suvorovii and Allium stipitatum — Structural analogs of furostanols

Two new glycosides of the cholestane series (allosides A and B) have been isolated from the fruit of the cocultivatedAllium suvorovii Rgi. andAllium stipitatum Rgl. (family Liliaceae, local name anzur). The acid hydrolysis of both compounds gave a sterol not previously described, which has been called alliosterol and has the structure of (22S)-cholest-5-ene-1, 3, 16, 22-tetraol, and the product of its dehvdration, which is (16S, 22S)-furost-5-ene-1, 3-diol. Alloside A is the 16-O--D-galactopyranoside, and alloside B the 16-O--D-galactopyranoside 1-O--D-glucopyranoside of alliosterol.Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 231–241, March–April, 1991.     

Triterpene glycosides ofAstragalus and their genins. Liv. askendoside G fromAstragalus taschkendicus

Chromatography of the polar fraction of a methanolic extract of the roots ofAstragalus taschkendicus Bunge (Leguminosae) has given a new triterpene glycoside of the cycloartane series, askendoside G, having the structure of 24R-cycloartane-3,6,16, 24, 25 pentaol 3-O-[(-L-arabinopyranosyl)-(12)--D-xylopyrano-side] 16-O--D-glucopyranoside.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (3712) 89 14 75. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 723–727, September–October, 1996. Original article submitted May 1, 1996.     

Triterpene glycosides of Astragalus and their genins XLII. Cycloartanes of Astragalus tragacantha

Another six components ofAstragalus tragacantha Habl. have been identified on the basis of spectral characteristics and chemical transformations. We have previously described cyclocanthagenin and its 3-0--D-xylopyranoside — cyclocanthoside A — as products of the acid hydrolysis of cyclocanthoside D. Cyclocanthosides B, C, E, and G are here described for the first time and are (24S)-cycloartane-3,6,16,24,25-pentol 3-O-(4-O-acetyl--D-xylopyranoside) 6-O--D-glucopyranoside, (24S)-cycloartane-3,6,16,24,25-pentol 6-O-(6-O-acetyl--D-glucopyranoside) 3-O--D-xylopyranoside, (24S)-cycloartane-3,6, 16,24,25-pentol 6-O--D-glucopyranoside, and (24S)-cycloartane-3, 6, 16, 24, 25-pentol 6-O--D-glucopyranoside 3-O-[O--D-glucopyranosyl-(12)--D-xylopyranoside], respectively.Institute of Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Tashkent. Institute of Ecological Genetics, Moldavian Academy of Sciences, Kishenev. Translated from Khimiya Prirodnykh Soedinenii, Nos. 3,4, pp. 360–367, May–August, 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.     

A new flavonoid isolated from the leaves ofCynara scolymus L.

Summary The fresh leaves of the artichokeCynara scolymus L. have yielded a new flavonoid glycoside, cynarotriside, having the structure luteolin 7-[O--D-glucopyranosyl-61-O--L-rhamnopyranoside]-4-O--D-glucopyranoside.Khimiya Prirodnykh Soedinenii, Vol. 2, No. 1, pp. 16–20, 1966     

Triterpene Glycosides of Astragalus and Their Genins. LXI. Occurrence of Cycloartane 6-O-Monodesmosides

Cyclosiversigenin 6-O--L-rhamnopyranoside and 6-O--D-glucopyranoside were isolated fromAstragalus coluteocarpusBoiss. (Leguminosae) andAstragalus dissectusB. Fedtsch. et N. Ivanova, respectively. Cyclosiversigenin 5-O--L-rhamnopyranoside was shown to be an artifact forAstragalus coluteocarpus.Thus, the cyclosiversigenin 6-O--D-glucopyranoside that was isolated from certainAstragalusspecies is hypothesized also to be an artifact. Glycosylation of the 6 -hydroxyl group of cycloartanes by D-glucose and D-xylose, in contrast with other substituents, does not change the low-field position of the PMR signal of the 4-CH ₃ group (1.65 2.01 ppm) that is caused by the influence of deuteropyridine directly on the 6 -hydroxyl. Obviously one of the hydroxyls of the -D-glucopyranoside or -D-xylopyranoside residues has the same effect in this instance.     

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 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 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.