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 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-3β, 6α, 16β, 25-tetraol 3-0-[0-α-L-rhamnopyranosyl-(1 → 2)-β-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.     

Triterpene glycosides of Astragalus and their genins XXXII. Cyclocarposide from Astragalus coluteocarpus

A new triterpene glycoside of the cycloartane series, which has been called cyclocarposide, has been isolated from the epigeal part of the plantAstragalus coluteocarpus Boiss. (Leguminosae). The structure of cyclocarposide has been established on the basis of chemical transformations and spectral characteristics as 20R,24S-epoxycycloartane-3β,6α,16β,25-tetraol 6-0-α-L-rhamnopyranoside 3-0-α-D-xylopyranoside. Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Pamir Biological Institute, Academy of Sciences of the Tadzhik SSR, Khorog. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 653–656, September–October, 1990.     

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

In addition to β-sitosterol, cyclosieversigenin, and β-sitosterol β-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-3β,6α,16β,25-tetraol 3-O-β-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.     

Cyclogaleginoside D from Astragalus galegiformis stems

The new cycloartane glycoside cyclogaleginoside D, which has the structure 25-O-β-D-glucopyranoside-20S, 25R-epoxycycloartan-3β, 6α, 16β, 25-tetraol 3-O-β-D-(2-O-acetyl)xylopyranoside was isolated from Astragalus galagiformis stems. The structure of the glycoside was established using chemical transformations and IR, PMR, and ¹³C NMR spectral data. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 255–256, May–June, 2006.     

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.     

Cycloascauloside a from Astragalus caucasicus leaves

The new cycloartane glycoside cycloascauloside A with the structure 20S,24R-epoxycycloartan-3β, 6α,16β,25-tetraol 3-O-[α-L-rhamnopyranosyl(1→6)]-β-D-(2′-O-acetyl)-glucopyranoside was isolated from leaves of Astragalus caucasicus Pall. The structure was established based on IR, PMR, and ¹³C NMR spectra and physicochemical properties of the compound itself and the products of its chemical transformations. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 359–361, July–August, 2006.     

Cyclochivinoside B from the aerial part of <Emphasis Type="Italic">Astragalus chivensis</Emphasis>

The known glycoside aleksandroside I and the new cycloartane glycoside cyclochivinoside B, 24S-cycloartan-3β,6α,16β,24,25-pentaol 3,25-di-O-β-D-glucopyranoside, were isolated from the aerial part of Astragalus chivensis. Their structures were established using chemical transformations and two-dimensional spectra (TOCSY, ROESY, HMBC, HSQC, COSY). __________ Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 138–140, March–April, 2007.     

Triterpene Glycosides from <Emphasis Type="Italic">Astragalus</Emphasis> and Their Genins. LXXI. Cycloorbicoside D,a New Glycoside from <Emphasis Type="Italic">Astragalus orbiculatus</Emphasis>

The new cycloartane glycoside cycloorbicoside D, which has the structure 23ξ,24ξ-cycloartan-3β6α,16β,23,24,25-hexaol 3-O-β-D-xylopyranoside, was isolated from the aerial part of Astragalus orbiculatus Ledeb. (Leguminosae). __________ Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 345–346, July–August, 2005.     

Steroids of the spirostan and furostan series from plants of the genus Allium. XXVI. Structure of anzurogenin and anzuroside from the collective fruits of Allium suvorovii and Allium stipitatum

A new steroid glycoside of the spirostan series, anzuroside, has been isolated from the collective fruits of the cocultivatedAllium suvorovii Rgl. andA. stipitatum Rgl. (family Liliaceae, local name “anzur”). Enzymatic cleavage of the glycoside has given the previously undescribed steroid sapogenin anzurogenic C, which has the structure of (24S, 25S)-2α,3β,5,24-tetrahydroxy-5β-spirostan-6-one. Anzuroside is the 24-O-β-D-glucopyranoside of anzurogenin C. Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 505–510, July–August, 1989.     

Structure of cyclochivinoside C from <Emphasis Type="Italic">Astragalus chivensis</Emphasis>

The new cycloartane glycoside cyclochivinoside C, 24S-cycloartan-3β,6α,16β,24,25-pentaol 3,16-di-O-β-D-glucopyranoside, was isolated from the aerial part of Astragalus chivensis. The structures of the isolated compounds were established by chemical transformations and PMR and ¹³C NMR spectra. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 460–462, September–October, 2007.     

Triterpene glycosides of Astragalus and their genins XXXII. Cyclocarposide from Astragalus coluteocarpus

A new triterpene glycoside of the cycloartane series, which has been called cyclocarposide, has been isolated from the epigeal part of the plantAstragalus coluteocarpus Boiss. (Leguminosae). The structure of cyclocarposide has been established on the basis of chemical transformations and spectral characteristics as 20R,24S-epoxycycloartane-3,6,16,25-tetraol 6-0--L-rhamnopyranoside 3-0--D-xylopyranoside.Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Pamir Biological Institute, Academy of Sciences of the Tadzhik SSR, Khorog. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 653–656, September–October, 1990.     

Triterpene glycosides ofTragacantha and their genins. Cyclostipulosides A and B fromTragacantha stipulosa

Two new triterpene glycosides of the cycloartane series, which have been called cyclostipulosides A and B, have been isolated in the individual form from the roots ofTragacantha stipulosa Boviss. Their structures have been established by physicochemical methods. Cyclostipuloside A is 24R-cycloartane-3β,6α,16β,24,25-pentaol 16-O-β-D-glucopyranoside 3-O-β-D-xylopyranoside, and cyclostipuloside B is 24R-cycloartane-3β,6α,16β,24,25-pentaol 6-O-α-L-arabinopyranoside 16-O-β-D-glucopyranoside 3-O-β-D-xylopyranoside. By the acid hydrolysis of cyclostipulosides A and B we have obtained the new glycoside 24R-cycloartane-3β,6α,16β,24,25-pentaol 16-O-β-D-glucopyranoside. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (371) 120 64 75. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 670–674, September–October, 1998.     

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.     

Triterpene glycosides from <Emphasis Type="Italic">Astragalus</Emphasis> and their genins. LXXXIX. Askendoside H from <Emphasis Type="Italic">Astragalus taschkendicus</Emphasis>

A new triterpene glycoside of the cycloartane series that was called askendoside H was isolated from roots of Astragalus taschkendicus Bunge (Leguminosae). Its structure was elucidated based on chemical transformations and spectral data. Askendoside H was a bisdesmoside of cycloorbigenin C, 23R,24Rcycloartan-3β,6α,16β,23,24,25-hexaol 3-O-[(α-L-arabinopyranosyl)(1 → 2)-β-D-xylopyranoside] 23-O-βD-glucopyranoside.     

Phytoecdysteroids of Rhaponticum carthamoides. II. Rhapisterone B

A new ecdysteroid (rhapisterone B) has been isolated from the seeds ofRhaponticum cathamoides (Willd.) Iljin. (familyCompositae). It has been shown that it is 2β, 3β, 11α, 14α, 20R, 24ξ-hexahydroxy-5β-cholest-7-en-6-one. Institute of the Chemistry of Plant Substances, Uzbek Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 806–808, November–December, 1991.     

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.     

Triterpene glycosides of Astragalus and their genins XLI. Cycloexoside from Astragalus exilis

In addition to known glycosides of the cycloartane series — cyclosieversiosides A, E, and F — a new acetylated compound of glycosidic nature — cycloexoside — has been isolated from the roots ofAstragalus exilis A. Kor. (Leguminosae). On the basis of chemical transformations and spectral characteristics, the structure of cycloexoside has been established as 20R,24S-epoxycycloartane-3,6,16,25-tetrol 3-O-(2,3-di-O-acetyl--D-xylopyranoside).Institute of Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Tashkent. Pamir Biological Institute, Tadhikistan Academy of Sciences, Khorog. Translated from Khimiya Prirodnykh Soedinenii, Nos. 3,4, pp. 356–360, May–August, 1992.     

Triterpene glycosides from <Emphasis Type="Italic">Astragalus</Emphasis> and their genins. XC. Askendoside K from <Emphasis Type="Italic">Astragalus taschkendicus</Emphasis>

A new triterpene cycloartane glycoside called askendoside K was isolated from roots of Astragalus taschkendicus Bunge (Leguminosae). The structure of this glycoside was established using chemical and biochemical transformations and spectral data. Askendoside K was a bisdesmoside of cycloorbigenin C and had the structure 23R,24R-cycloartan-3β,6α,16β,23,24,25-hexaol 3-O-[(α-L-arabinopyranosyl)(1 → 2)-β-D-xylopyranoside],23-O-[(β-D-glucuronopyranosyl)(1 → 2)-β-D-glucopyranoside].     

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.