Triterpeneglycosides of Astragalus and their genins. XXV. Cyclocanthoside D from Astragalus tragacantha

The epigeal part of the plant ofAstragalus tragacantha Habl. (Leguminosae) has yielded, together with cyclosieversigenin 3-O--D-xylopyranoside, a new glycoside of the cycloartane series — cyclocanthoside D, the structure of which has been established on the basis of chemical transformations and spectral characteristics as 24S-cycloartane-3,6,16,24,25-pentaol 16-O--D-glucopyranoside 3-O--D-xylopyranoside.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 73–76, January–February, 1988.     

Astragalus triterpene glycosides and their genins. I. Structures of cycloalpigenin and cycloalpioside

Another two methylsteroids of the cycloartane series have been isolated from the epigeal part ofAstragalus alopecurus. The structures of the compounds isolated, cycloalpigenin and cycloalpioside, have been established as (20R,24R)-16,24:20, 24-diepoxycycloartane-3,7,25-triol and (20R,24R)-16, 24:20,24-diepoxycycloartane-3,7, 25-triol 3-O--D-xylopyranoside, respectively, on the basis of chemical transformations and spectral characteristics. The structure of cycloalpigenin has been confirmed by chemical correlation with that of cycloalpigenin D.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. 700–708, September–October, 1995. Original article submitted February 1, 1995.     

Triterpene glycosides of Astragalus and their genins XXXVII. Cycloaraloside F from Astragalus amarus and Astragalus villosissimus

The glycosides of the plantAstragalus villosissimus Bunge have been studied. Four glycosides have been isolated from the roots of this plant, and two of them have been identified as -sitosterol -D-glucopyranoside and cycloaraloside C. The most polar glycoside, which has also been isolated from the roots ofAstragalus amarus Pall., proved to be a new triterpene glycoside of the cycloartane series and has been called cycloaraloside F. It is a trioside of cyclosieversigenin containing two molecules of D-glucose and one molecule of D-apiose. On the basis of chemical transformations and spectral characteristics, the structure of cycloaraloside F has been established as 20R, 24S-epoxycycloartane-3,6,16,25-tetraol 3-0-[O-D-apio--D-furanosyl-(12)--D-glucopyranoside] 25-O--D-glucopyranoside.Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 374–377, May–June, 1991.     

Triterpene glycosides of Astragalus and their genins XXX. Cycloaraloside A from Astragalus amarus

In addition to -sitosterol, cyclosieversigenin, and -sitosterol -D-glucopyranoside, the roots of the plantAstragalus amarus Pall. (Leguminosae) have yielded a new triterpene glycoside of the cycloartane series — cycloaraloside A, which has the structure of 2OR,24S-epoxycycloartane-3,6,16,25-tetraol 3-O--D-glucopyranoside.Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 806–809, November–December, 1989.     

Triterpene glycosides of Astragalus and their genins XXXIX. Cycloaraloside D from Astragalus amarus

The structure of a triterpene glycoside of the cycloartane series — cycloaraloside D, isolated from the roots ofAstragalus amarus Pall. (Leguminosae) — has been established on the basis of chemical transformations and spectral characteristics. Cycloaraloside D is 20R, 24S-epoxycycloartane-3, 6, 16, 25-tetraol 3-0-[0--L-rhamnopyranosyl-(1 2)--D-glucopyranoside].Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 526–528, July–August, 1991.     

Iriterpene glycosides of Astragalus and their genins XLIII. Cycloaraloside B from Astragalus amarus

The structure of a new cycloartane glycoside, cycloaraloside B, isolated from the roots ofAstragalus amarus Pall. (Leguminosae) has been established on the basis of chemical transformations and spectral characteristics: it is 20R,24S-epoxycycloartane-3,6,16,25-tetraol 3-O-[O--L-rhamnopyranosyl-(12)-(6-O-acetyl--D-glucopyranoside)].Institute of Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 528–531, September–October, 1992.     

Triterpene glycosides of Astragalus and their genins. XXIII. Cyclocanthogenin from Astragalus tragacantha

The epigeal part of the plantAstragalus tragantha Habl. (Leguminosea) has yielded (in addition to cyclosieversigenin, cyclocyclosiversioside F, and -sitosterol -D-glucopyranoside) a new methylsteroid of the cycloartane series — cyclocanthogenin — the structure of which has been established on the basis of chemical transformations and spectral characteristics, and also of a chemical correlation with the structure of cycloasgenin C, as 24S-cycloartane-3,6,16,24,25-pentaol.Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 817–824, November–December, 1987.     

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.     

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. 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.     

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 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 of Astragalus and their genins XXXV. Cycloaraloside C from Astragalus amarus

A new triterpene glycoside of the cycloartane series (cycloaraloside C) has been isolated from the roots of the plantAstragalus amarus Pall. (Leguminosae). Cycloaraloside C is a bioside of cyclosieversigenin including one D-glucose residue and one D-apiose residue. The structure of the glycoside has been shown on the basis of the chemical transformations and spectral characteristics as 20R,24S-epoxycycloartane-3,6,16,25-tetraol 3-O-[O-(D-apio--D-furanosyl)-(1 2)--D-glucopyranoside]. This is the first time that D-apiose has been found among cycloartane glycosides.Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 783–787, November–December, 1990.     

Triterpene glycosides ofAstragalus and their genins. XLVIII. The structures of cycloalpigenin B and cycloalpioside B

The structures of the new cycloartane methylsteroid cycloalpigenin B and its glycoside cycloalpioside B, isolated fromAstragalus alopecurus Pall. (Leguminosae) have been determined on the basis of chemical transformations with the assistance of¹H and¹³C NMR spectroscopy and 2D NMR¹H-¹H and¹H-¹³C correlations of chemical signals and IR, CD, and electron-impact mass spectrometry. Cycloalpigenin B is 20R,24S-epoxycycloartane-3,12,16,25-tetraol. A transition from cycloalpigenin B to cycloalpigenin A has been achieved. Cycloalpioside B is 20R,24S-epoxycycloartane-3,12,16,25-tetraol 3-O--D-xylopyranoside.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. 4, pp. 515–521, July–August, 1994.     

Cardenolide glycosides ofCheiranthus allioni. XV. Glucocheiranthoside

Another new cardenolide glycoside has been isolated from the plantCheiranthus allioni Hort., and has been named glucocheiranthoside. Its chemical structure has been established as 3-(4-O--D-glucopyranosyl--D-gulmoethylpyranosyloxy)-14-hydroxy-19-oxo-5,14-card-20(22)-enolide.State Scientific Center for Drugs, Ukraine, 310085, Kharkov, USSR. ul. Astronomicheskaya, 33. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 269–271, March–April, 1994.     

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.     

Secondary metabolites of Astragalus danicus Retz. and A. inopinatus Boriss.

The chemical composition of the above-ground parts of Astragalus danicus and A. inopinatus collected in the Baikal region (Eastern Siberia) was studied for the first time. From A. danicus, pentacyclic triterpene saponins were isolated and identified, viz., 3-O-(-glucuronopyranosyl)-3,22,24-trihydroxyolean-12-ene, 3-O-[O-(-d-xylopyranosyl)-(12)-(-glucuronopyranosyl)]-3,22,24-trihydroxyolean-12-ene, 3-O-[O-(-d-glucopyranosyl)-(12)-(-glucuronopyranosyl)]-3,22,24-trihydroxyolean-12-ene, 3-O-[O-(-l-rhamnopyranosyl)-(12)-O-(-d-xylopyranosyl)-(12)-(-glucuronopyranosyl)]-3,22,24-trihydroxyolean-12-ene, 3-O-[O-(-l-rhamnopyranosyl)-(12)-O-(-d-glucopyranosyl)-(12)-(-glucuronopyranosyl)]-3,22,24-trihydroxyolean-12-ene, 3-O-methyl-d-chiro-inositol, and linolenic acid. In A. inopinatus, the same saponins were identified as well as tricosan-1-ol and tetracosan-1-ol, 5,7,4"-trihydroxyflavon (apigenin), and a tetracyclic triterpenoid, 20(R),24(S)-epoxycyclolanost-9(11)-ene-3,6,16,25-tetrol (cycloastragenol). All reported compounds from the both genus of Astragalus were isolated for the first time. Methanolic extracts of A. danicusand A. inopinatus exhibited low inhibitory activity with respect to the growth of HeLa cells. The chloroform fraction of A. danicus showed a strong antimicrobial activity against Staphylococcus aureus and a strong cytotoxic activity against HeLa cells.     

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 Astragalus and their genins XL. Cyclocarposide B from Astragalus coluteocarpus

In addition to cyclosieversigenin, -sitosterol -D-glucopyranoside, and cyclocarposide, we have isolated another three glycosides of triterpene nature from the epigeal part of the plantAstragalus coluteocarpus Boiss. (Leguminosae). On the basis of chemical transformations and spectral characteristics, the structure of one of the new glycosides, which we have called cyclocarposide B, has been established as 20R,24S-epoxycycloartane-3,6,16,25-tetraol 6-O--L-(2-O-acetylrhamnopyranoside) 3-O--D-xylopyranoside.Institute of Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 227–231, March–April, 1992.