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.     

Sulfated steroid glycosides from the Viet Namese starfish <Emphasis Type="Italic">Linckia laevigata</Emphasis>

Five sulfated steriodal compounds including one new glycoside called linckoside L7 (1) and four previously known glycosides 2–5 were isolated from the starfish Linckia laevigata. The structure sodium (22E, 24R)-3-O-(2-O-methyl-β-D-xylopyranosyl)-29-O-(β-D-xylopyranosyl)-24-ethylcholest-4,22-dien-3β,6β,8,15α,16β,29-hexaol 15-O-sulfate was proposed for L7. Linckoside L7 inhibited fertilization and egg-cell development in the sea urchin Strongylocentrotus intermedius. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 64–67, January–February, 2007.     

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 from <Emphasis Type="Italic">Astragalus</Emphasis> and their genins. LXXX. Cyclomacroside D,a new bisdesmoside

The structure of the new cycloartane glycoside cyclomacroside D, which was isolated from Astragalus macropus Bunge (Leguminosae) and is 24R-cycloartan-1α,3β,7β,24,25-pentaol 3-O-α-L-rhamnopyranoside–24-O-β-D-xylopyranoside, was proved. Presented at the 7th International Symposium on the Chemistry of Natural Compounds (SCNC, Tashkent, Uzbekistan, October 16–18, 2007). Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 48–50, January–February, 2009.     

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.     

Asterosaponin P2 from the Far-Eastern starfishpatiria (asterina) pectinifera

A new polyhydroxylated steroidal glycoside, asterosaponin P₂, was isolated from the Far-Eastern starfishPatiria (Asterina) pectinifera. The glycoside was identified as the 24R)-29-O-[2-O-sulfo-α-L-arabinofuranosyl]-24-ethyl-5α-cholestane-3β, 6α,8β,15α,16β,29-hexol Na salt. Published inIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1818–1820, October. 2000     

Structure of a steroid saponin from <Emphasis Type="Italic">Digitalis ciliata</Emphasis>

A new steroid glycoside was isolated from leaves of Digitalis ciliata (Scrophulariaceae) by fractionation of the total extracted substances. Its structure was determined as (25R)-5α-spirostan-3β-ol 3-O-β-D-glucopyranosyl-(1→3)[β-D-fucopyranosyl-(1→2)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside based on chemical transformations, physical constants, and spectral data. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 135–137, March–April, 2007.     

Furostane-Type Steroidal Saponin from <Emphasis Type="Italic">Digitalis ciliata</Emphasis>

A new furostane-type steroidal glycoside and derivative of tigogenin (1) was isolated from aqueous wastes from production of the cardiac drug acetyldigitoxin from leaves of Digitalis ciliata Trautv. (Scrophulariaceae) and characterized. The structure of the glycoside was established using physical constants, chemical transformations, and spectral data as 3-O-β-D-glucopyranosyl-(1→3) [β-D-fucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-β-D-galactopyranosyl-(25R)-5α-furostan-3β,22α,26-triol-26-O-β-D-glucopyranoside.     

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.     

New triterpenoid glycosides fromThalictrum minus L.

From the terrestrial part ofThalictrum minus L. (Ranunculaceae) a novel triterpenoid diglycoside was isolated. The genin of this glycoside is a new cycloartane triterpenoid. The structure of the glycoside was established on the basis of 1D and 2D NMR spectroscopy and FAB mass spectrometry as 22S,25-epoxy-3-O-β-d-galactopyranosyl-29-O-β-d-glucopyranosyl-9β, 19-cyclo-20S-lanostane-3β,16β,24S,29-tetrol. For Part 10 see Ref. 1. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 602–605, March, 1999.     

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].     

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.     

Triterpene glycosides from <Emphasis Type="Italic">Astragalus</Emphasis> and their genins. LXXXIII. Structure of cyclomacroside A

The structure of the novel cycloartane triterpene glycoside cyclomacroside A, which was isolated from Astragalus macropus Bunge (Leguminosae) roots, was determined as 3-O-α-L-rhamnopyranoside-24,25-isopropylidenedioxy-24R-cylcoartan-1α,3β,7β-triol.     

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.     

A new stilbene glycoside from the <Emphasis Type="Italic">n</Emphasis>-butanol fraction of <Emphasis Type="Italic">Veratrum dahuricum</Emphasis>

A new stilbene glycoside, 5-methylresveratrol-3,4′-O-β-D-diglucopyranoside (1), was isolated from the n-butanol fraction of the rhizomes of Veratrum dahuricum, together with five known stilbenoids: resveratrol-3-O-β-D-glycoside (2), 4′-methylresveratrol-3-O-β-D-glycoside (3), oxyresveratrol-4′-O-β-D-glycoside (4), oxyresveratrol-3-O-β-D-glycoside (5), and oxyresveratrol-3,4′-O-β-D-diglycoside (6), and found for the first time in the investigated plant. The structures of six isolates were identified on the basis of 1D and 2D NMR data. Compounds 1–6 showed platelet aggregation inhibition, and compound 1 had an IC₅₀ value of 383.6 μM against platelet aggregation induced by AA. Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 279–282, May–June, 2009.     

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 3β-(4′-O-β-D-glucopyranosyl-β-D-gulmoethylpyranosyloxy)-14-hydroxy-19-oxo-5β,14β-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.     

A new triterpene glycoside from <Emphasis Type="Italic">Premna microphylla</Emphasis>

A new triterpene glycoside, namely 28-O-α-L-rhamnopyranosyl (1→2)-β-D-glucopyranoside tormentic acid ester, was isolated from the leaves of Premna microphylla, together with two known triterpenes, i.e., arjunolic acid (2) and hyptatic acid A (3). Its structure was established by mass-spectrometric and spectroscopic methods, especially 2D NMR techniques. This is the first report of the isolation of triterpenes from this plant. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 173–174, March–April, 2009.     

Triterpene glucosides of <Emphasis Type="Italic">Astragalus</Emphasis> and their genins. LXXIV. Cyclotrisectoside,the first trisdesmoside of cyclocephalogenin

The two trisdesmoside cycloartane glycosides astragaloside VII and cyclotrisectoside were isolated from Astragalus dissectus (Leguminosae) and identified. The latter was 20R,25-epoxy-24S-cycloartan-3β,6α,16β,24-tetraol 3-O-β-D-xylopyranoside-6,24-di-O-β-D-glucopyranoside and was a new natural compound. Presented at the Sixth International Symposium on the Chemistry of Natural Compounds (SCNC, Turkey, Ankara, 28–29 June 2005). __________ Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 132–134, March–April, 2007.     

Phytoecdysteroids of the plants of the genusSilene XV. Silenoside F — Brahuisterone 3-O-β-D-glucopyranoside fromSilene brahuica

A new brahuisterone glycoside — silenoside F — has been isolated from the epigeal part ofSilene brahuica Bois. (fam. Caryophyllaceae). Its structure has been established by an analysis of spectral characteristics: 3β,5,14α,22R,25-pentahydroxy-5β-cholest-6-one 3-O-β-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. 6, pp. 734–737, November–December, 1994.     

Triterpene glycosides from Kalopanax septemlobum. VII. Minor glycosides from stems of Kalopanax septemlobum var. maximowiczii and Kalopanax septemlobum var. typicum

Sixteen triterpene glycosides, three of which were new, hederagenin 28-O-β-D-glucuronopyranosyl ester and 28-O-β-D-gentiobiosyl ester and oleanolic acid 3-O-α-L-arabinopyranoside, were isolated from stem bark of Kalopanax septemlobum. The glycoside contents in stem bark of two varieties, maximowiczii and typicum, were compared. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 49–53, January–February, 2006.