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.     

Triterpene Glycosides of Astragalus and Their Genins. LXIV. Chemical Transformation of Cycloartanes. V. Synthesis of Cyclopycanthogenin from Cyclosiversigenin

The partial synthesis of cyclopycanthogenin, 20R,24S-epoxycycloartan-6,16,25-triol-3-one, was developed in four steps from cyclosiversigenin.     

Triterpene Glycosides of Astragalus and Their Genins. LXVII. Structure of Cycloexoside B

Another seven components from the roots of Astragalus exilis A.Kor. (Leguminosae) were identified using spectral data and chemical transformations. A triterpenoid of genin nature was identical to cyclosiversigenin. One compound of glycosidic nature turned out to be a new cycloartane glycoside called by us cycloexoside B of structure 20R,24S-epoxycycloartan-3,6,16,25-tetraol 3-O--D-(2-Oacetyl) xylopyranoside. Five glycosides were identified as cyclosiversigenin 3-O--D-xylopyranoside and cyclosiversiosides B, C, D, and G.     

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. 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.     

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 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.     

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 and Their Genins from Astragalus. LXIX. Orbigenin, the First Lanostanoid from Astragalus Plants

The new lanostane methylsteroid orbigenin, the structure of which is 23,24-lanost-9(11)-en-3,7,16,19,23,24,25-heptaol, was isolated from Astragalus orbiculatus Ledeb. (Leguminosae). The structure of the new triterpenoid, the first lanostanoid from plants of the Astragalus genus, was determined using electron-impact mass spectrometry and PMR and ¹³C NMR spectroscopies interpreted using J-modulation, DEPT, and the 2D NMR methods: ¹H-¹H COSY, HSQC, and HMBC.     

Triterpene Glycosides of Astragalus and Their Genins. LXX. Orbicoside, the First Lanostane Glycoside from Astragalus Plants

Orbicoside, a new lanostane glycoside and the first from plants of the Astragalus genus, was isolated from the aerial organs of Astragalus orbiculatus Ledeb. (Leguminosae). It has the structure 23,24-lanost-9(11)-en- 3,7,16,19,23,24,25-heptaol 3-O--D-xylopyranoside. The structure of orbicoside was established using PMR and ¹³C NMR, which were interpreted using DEPT and 2D NMR spectroscopies ¹H-¹H COSY, HSQC, and HMBC.     

Triterpene Glycosides of Astragalus and Their Genins. LXVIII. Cycloorbigenin C, a New Cycloartane Genin

The new triterpenoid cycloartane cycloorbigenin C, the structure of which is 23ξ,24ξ-cycloartan-3β,6α,16β,23,24,25-hexaol, was obtained from the aerial part of Astragalus orbiculatus Ledeb. (Leguminosae). The structure of cycloorbigenin C was proved using chemical transformations, IR spectroscopy, electron-impact mass spectrometry, and PMR and ¹³C NMR spectra interpreted using J-modulation and the 2D NMR spectroscopies: ¹H-¹H COSY, TOCSY, ROESY, HSQC, and HMBC.     

Triterpene Glycosides from Astragalus. Structure of Cyclounifolioside B from Astragalus unifoliolatus

The previously known astrailienin A and the new cycloartane glycoside cyclounifolioside B with structure cyclosiversigenin 3-O-[-D-glucopyranosyl(1-2)]--D-glucopyranoside were isolated from Astragalus unifoliolatus Bunge. The structures of these compounds were established using chemical transformations and two-dimensional spectra (ROESY, HMBC, HSQC, TOCSY, COSY).     

Triterpene Glycosides of Zygophyllum eichwaldii. III. Structure of Zygoeichwaloside G

The new triterpene glycoside zygoeichwaloside G was isolated from the roots of Zygophyllum eichwaldii C.A.M. by column chromatography. Acid hydrolysis and PMR and ¹³C NMR spectroscopy using twodimensional COSY, TOCSY, and HSQC and analysis of HMBC and ROESY spectra established that glycoside G is 19--hydroxyursolic acid 3-O--L-(2-O-sulfo)-arabinopyranoside.     

Triterpene Glycosides from Plants of the Astragalus Genus. III. Structure of Cyclounifolioside C from Astragalus unifoliolatus

The known compound cyclocantogenin (1) and a new cycloartane glycoside cyclounifolioside C (2), which has the structure 24R-cycloartan-3,6,16,24,25-pentaol 3-O--D-glucopyranoside, were isolated from roots of Astragalus unifoliolatus Bunge. The structures of the isolated compounds are established using hydrolysis and spectral data.     

Triterpene Glycosides of Fatsia japonica. IV. Structure of Glycosides D1 and D2 from Seeds

Seeds ofFatsia japonica(Araliaceae) afforded the known hederagenin 3-O--D-glucopyranosyl-(12)-O--L-arabinopyranoside and the new triterpene glycoside D ₂ , for which the structure hederagenin 3-O--D- galactopyranosyl-(12)-O--L-arabinopyranoside was proposed based on chemical methods and NMR spectroscopy