Triterpene Glycosides of Astragalus and Their Genins. LXVI. Cycloorbicoside C, a New Bisdesmoside

The new triterpene glycoside cycloorbicoside C was isolated from the aerial parts of Astragalus orbiculatus Ledeb. (Leguminosae) and was identified as (23R,24S)-16,23;16,24-diepoxycycloartan-3,25-diol 3-O--D-xylopyranoside 25-O--D-glucopyranoside.     

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 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 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.     

Structure of Cyclogaleginoside E from Astragalus galegiformis

The new cycloartane glycoside cyclogaleginoside E, 20S,24R-cycloartan-3,6,16,25-tetraol-3-O--D-xylopyranoside-25-O--D-glucopyranoside, was isolated from stems of Astragalus galegiformis L. Its structure was established using enzymatic and total acid hydrolysis, mass spectrometry, and PMR and ¹³C NMR.     

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.     

Triterpenoid Glycosides of Fatsia japonica. II. Isolation and Structure of Glycosides from the Leaves

The previously known triterpenoid 3-O--L-arabinopyranosides of oleanolic and echinocystic acids and hederagenin, 3-O--D-glucopyranosyl-(12)-O--L-arabinopyranosides of oleanolic acid and hederagenin, in addition to 28-O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl ethers of the 3-O--L-arabinopyranoside of hederagenin, and 3-O--D-glucopyranosyl-(12)-O--L-arabinopyranosides of oleanolic acid and hederagenin, respectively, are isolated from leaves ofFatsia japonica(Araliaceae). The structures of the glycosides are confirmed by chemical methods and ¹³ C NMR spectroscopy     

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.     

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 Plants of the Astragalus Genus. IV. Structure of Cyclounifolioside D from Astragalus unifoliolatus

The new cycloartane glycoside cyclounifolioside D (1) was isolated from roots of Astragalus unifoliolatus Bunge. The structure of 16-O-acetyl-24R-cycloartan-3,6,16,24,25-pentaol 3-O--D-glucopyranoside was established using chemical transformations and spectral data.     

Triterpene Glycosides of Tragacantha Stipulosa and Their Genins. Structures of Askendosides G and D and Cycloglobiceposide B from One- and Two-Dimensional 1H and 13C NMR Spectroscopy

Roots of Tragacantha stipulosa Boriss yielded three triterpene glycosides of the cycloartane series: askendoside G (1), askendoside D (2), and cycloglobiceposide B (3). Glycoside 1 is 3-O--L-arabinopyranosyl-(12)--D-xylopyranoside; 16-O--D-glucopyranoside-24R-cycloartan-3,6,16,24,25-pentaol; 2 - 3-O--L-arabinopyranosyl-(12)--D-xylopyranoside; 6-O--D-xylopyranoside-20R,24S-epoxycycloartan-3,6,16,25-tetraol; 3 - 3-O--D-xylopyranoside; 16-O--D-glucopyranoside; 25-O--D-glucopyranoside-24R-cycloartan-3,6,16,24,25-pentaol.     

Cardiac glycosides of Cheiranthus allioni. XI

Summary Another three cardiac glycosides have been isolated from the seeds ofCheiranthus allioni hort. One of them has been identified as digifucocellobioside (digitoxigenin 3 -O-[O--D-glycopyranosyl(1 4)-O--D-glucopyranosyl(1 4)-O--D-fucopyranoside]). The two other glycosides, called digitoxigenin gulomethyloside and glucodigigulomethyloside are, respectively, digitoxigenin 3 -O--D-gulomethyloside and digitoxigenin 3 -O-(4-O--D-glucosyl--D-gulomethyloside).For Communication X, see [1].Khar'kov Scientific-Research Institute of Pharmaceutical Chemistry. All-Union Scientific-Research Institute of Medicinal Plants. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 754–758, November–December, 1975.     

Triterpene glycosides and their genins fromThalictrum foetidum. V. Structure of cyclofoetoside B

A new glycoside (cyclofoetoside B) (I) has been isolated from the epigeal part of the plantThalictrum foetidum L. (Ranunculaceae). On the basis of chemical transformations and with the aid of physicochemical characteristics it has been established that cyclofoetoside B is 24S-cycloartane-3, 16, 24, 25, 29-pentaol 3-O--L-arabinopyranoside 16-O-[O--L-rhamnopyranoside-(1 6)--D-glucopyranoside], C₄₇-H₈₀O₁₇, mp 194–197°C (methanol); [] _D ²⁴ +15.7 ± 2° (c 0.88; pyridine). The enzymatic hydrolysis of (I) has yielded cyclofoetigenin B (III), 24S-cycloartane-3,16,24,25,29-pentaol 16-O--D-glucopyranoside, (IV), C₃₆H₆₂O₁₀, mp 223–225°C (acetone), [] _D ²⁴ +37 ± 2° (c 0.97; methanol) and 24S-cycloartane-3,16,24,25,29-pentaol 16-O-[O--L-rhamnopyranosyl-(1 6)--D-glucopyranoside, C₄₂H₇₂O₁₄, mp 229–231°C (methanol), [] _D ³⁰ +41 ± 2° (c 0.7; methanol). Details of the IR and¹H and¹³C NMR spectra of the compounds are given.Irkutsk Institute of Organic Chemistry, Academy of Sciences of the USSR. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Trashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 341–345, May–June, 1986.     

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 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.     

Steroids of the spirostan and furostan series from Nolina microcarpa IV. Structures of nolinogenin,nolinospiroside B,and nolinofuroside B

A glycoside has been isolated from the plantNolina microcarpa S. Wats. (family Dracaenaceae) which has been called nolinofuroside B and has the structure of 6-methoxy-3,5-cyclo-(25S)-furostan-1,22,26-triol 1-O--D-fucopyranoside 26-O--D-glucopyranoside (I). Enzymatic hydrolysis of the bioside (I) yielded nolinospiroside B (III) and nolinogenin (IV). The latter is 6-methoxy-3,5-cyclo-(25S)-spirostan-6-ol, and glycoside (III) is its 1-O--D-fucopyranoside.M. V. Frunze Simferopol' State University. Institute of Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 218–224, March–April, 1992.     

New asterosaponins from the starfishDismolasterias nipon

Three new glycosides, D₁, D₂, and D₃, have been isolated from the Far Eastern starfishDistolasterias nipon. They have been identified by chemical and physicochemical methods as 5-cholestane÷3,6,8,15,24-pentaol 3,24-di-O--D-xylopyranoside, t-cholest-22-ene-3,6,8,15,24-pentaol 3,24-di-O--D-xylopyranoside (II), and 5-cholestane-3,6,8,15,24-pentaol 24-O--D-glucopyranoside 3-O--D-xylopyranoside (III).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. 250–255, March–April, 1987.     

Triterpene glycosides of Astragalus and their genins XLIV. Structure of cyclocarposides A and C

The structures of two new cycloartane glycosides — cyclocarposides A and C, isolated from the herbAstragalus coluteocarpus Boiss. — have been established on the basis of spectral characteristics and chemical transformations. Cyclocarposides A and C are: 204R,24S-epoxycycloartane-3,6,17,25-tetraol 3-O-(2-O-acetyl--D-xylopyranoside)6-O-(2-O-acetyl--L-rhamnopyranoside) and 20R,24S-epoxycyloartane-3,6,16,25-tetraol 3-O-(2-O-acetyl--D-xylopyranoside) 6-O--L-rhamnopyranoside, respectively.Institute of Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Tashkent. Pamir Biological Institute, Tadzhikistan Academy of Sciences, Khorog. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 694–698, November–December, 1992.     

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 Astragalus and their genins. XXIV. Cycloorbicoside G from Astragalus orbiculatus

A bisdesmosidic glycoside — cycloorbicoside G — has been isolated from the epigeal parts of the plantAstragalus orbiculatus Ledeb. (Leguminosae), and on the basis of chemical transformations and spectral characteristics its structure has been established as (23R,24S)-16,23;16,24-diepoxycycloartane-3,7,25-triol 25-O--D-glucopyranoside 3-O--D-xylopyranoside.Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 837–842, November–December, 1987.