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 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 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     

Gitoxigenin glycosides

Summary Three cardiac glycosides have been synthesized from gitoxigenin and D-glucose: gitoxigenin 3-O--D-glucopyranoside, gitoxigenin 16 -O- -D-glucopyranoside, and gitoxigenin 3, 16-di-O- -D-glucoside. The first glycoside, obtained with a yield of 49% on the weight of the initial aglycone, possesses a fairly high biological activity (0.25 mg/kg), while the other two, formed in a yield of about 0.3%, do not possess the action on the heart that is specific for the cardenolides.Khar'kov Chemical and Pharmaceutical Scientific-Research Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 45–49, January, 1971.     

Two new triterpene glycosides from the holothurian Duasmodactyla kurilensis

Two new glycosides have been isolated from the total triterpene glycosides of the holothurianDuasmodactyla kurilensis: kurilosides A (III) and C (IV). It has been established that (III) is 16-acetoxy-3-{[O--D-glucopyranosyl-(1 4)-O--D-quinovopyranosyl-(1 2)]-[O-(3-O-methyl--D-glucopyranosyl)-(1 3)-O-(6-O-(sodium sulfato)--D-glucopyranosyl)-(1 4)]--D-xylopyranosyloxy}-4,4,14-trimethylpregen-9(11)-en-20-one, while the minor glycoside (IV) is 16-acetoxy-3-{O--D-quinovopyranosyl-(1 2)-[O-(3-O-methyl--D-glucopyranosyl-(1 3)-O-(6-O-(sodium sulfato)--D-glucopyranosyl)-(1 4)]--D-xylopyranosyloxy}-4,4,14-trimethylpregn-9(11)-en-20-one.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 221–226, March–April, 1991.     

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 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 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.     

Triterpene glycosides ofHedera helix III. Structure of the triterpene sulfates and their glycosides

From the leaves of English ivyHedera helix L. we have isolated the known 3-sulfates of oleanolic and echinocystic acids and their 28-O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl esters and the new 3-sulfate of 28-O--gentiobiosyl oleanolate — helicoside L-8a. The structures of the compounds isolated were deduced from the results of chemical transformations and NMR spectroscopy.Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 87–90, January–February, 1999.     

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.     

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.     

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 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     

Coumarin glycosides ofHaplophyllum performatum. structures of haploperosides C,D, and E

New coumarin glycosides — haploperosides C, D, and E — have been isolated from the epigeal part of theHaplophyllum performatum (MB) Kar et Kir. On the basis of chemical transformations and spectral characteristics, haploperoside D has the structure of 6-methoxy-7-[0--L-rhamnopyranosyl-(1 2)--D-glucopyranosyloxy]-2H-benzopyran-2-one, and haploperoside C that of 6-methoxy-7-[0--L-rhamnopyranosyl-(1 6)-(2-0-acetyl--D-glucopyranosyloxy)]-2H-benzopyran-2-one. The structure of haploperoside E has been established as 7-[0--L-rhamnopyranosyl-(1 2)-0--L-rhamnopyranosyl-(1 6)--D-glucopyranosyloxy]-2H-benzopyran-2-one. The structures of haploperosides A and B have been refined. An assignment has been made of the carbon signals in the¹³C NMR spectra of haploperosides A, D, C, and E.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 27–35, January–February, 1985.     

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 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 and Their Genins from Tragacantha stipulosa. Structure of Cyclostipuloside C

A new cycloartane glycoside of the cyclostipuloside C series, 3-O--D-xylopyranoside-6,16-di-O--D-glucopyranoside-20S-24R-epoxycycloartan-3,6,16,25-tetraol is isolated from aerial organs of Tragacantha stipulosa Boriss.     

Cardiac glycosides of Cheiranthus allioni. V

Conclusions Two additional cardiac glycosides, glucoerysimoside and glucoerysimosol, have been isolated from the seeds ofCheiranthus allioni Hort. Glucoerysimoside is strophanthidin 3-[O--D-digitoxopyranosyl-(4 1)-O--D-glucopyranosyl-(4 1)--D-glucopyranoside]. Glucoerysimosol is a new cardenolide having the same carbohydrate component, but its aglycone is strophanthidol. From these glycosides a new trisaccharide has been obtained which has been characterized as 4-O--cellobiosyl-D-digitoxose.Khar'kov Scientific-Research Institute of Pharmaceutical Chemistry. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 566–571, September–October, 1970.     

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.     

Structure of cucumarioside G1 — A new triterpene glycoside from the holothurianCucumaria fraudatrix

A new triterpene glycoside — cucamarioside G₁ — has been isolated from the Pacific Ocean holothurianCucumaria fraudatrix. On the basis of physicochemical characteristics and the results of chemical transformations, its structure has been established as 16-acetoxy-3-[O-(3-O-methyl--D-xylopyranosyl)-(1 3)-O--D-glucopyranosyl-(1 4)--D-quinovopyranosyl-(1 2)-(4-O-sulfato--D-xylopyranosyloxy)]-holosta-7,24-diene.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 244–248, March–April, 1985.