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.     

Triterpene glycosides from <Emphasis Type="Italic">Astragalus</Emphasis> and their genins. LXXVII. Cyclomacrogenin B,a new cycloartane triterpenoid

Ten pure compounds, three of which were identified as β-sitosterol, β-sitosterol β-D-glucopyranoside, and D-3-O-methyl-chiro-inositol, were isolated from roots of Astragalus macropus Bunge (Leguminosae). The structure of the new cycloartane triterpenoid cyclomacrogenin B was established as 24R-cycloartan-1α,3β,7β,24,25-pentaol. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 502–504, September-October, 2008. Original article submitted May 26, 2008.     

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.     

Triterpene glycosides from <Emphasis Type="Italic">Astragalus</Emphasis> and their genins. LXXXI. Chemical transformation of cycloartanes. VII. Synthesis of cyclosiversigenin lactone

The lactone 20R-25-norcycloartan-3β,6α,16β-triol-20,24-olide was synthesized from cyclosiversigenin. Presented at the 1st International Symposium on Edible Plant Resources and the Bioactive Ingredients, Xinjiang, China, July 25–27, 2008. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 324–327, May–June, 2009.     

Triterpene glycosides from Astragalus and their genins. LXXVIII. Chemical transformation of cycloartanes. VI. Partial synthesis of cycloadsurgenina

Cycloadsurgenin, 20R,24 S-epoxycycloartan-6α,25-diol-3,16-dione, was partially synthesized in four steps from cyclosieversigenin. Side products with the structures 17E,24S-cycloart-17-en-6α,24,25-triol-3,16-dione and 17Z,24 S-cycloart-17-en-6α,24,25-triol-3,16-dione were obtained in addition to the desired product. Presented at the 1st International Symposim on Edible Plant Resources and the Bioactive Ingredients, Xinjiang, China, July 25–27, 2008. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 591–595, November–December, 2008.     

Cycloascauloside b from <Emphasis Type="Italic">Astragalus caucasicus</Emphasis>

The structure of a new cycloartane glycoside isolated from leaves of Astragalus caucasicus Pall. (Leguminosae) was elucidated using chemical transformations and spectral data. Cycloascauloside B is 20R, 25-epoxy-24S-cycloartan-3β,6α,16β,24-tetraol 3-O-[α-L-rhamnopyranosyl-(1å2)]-β-D-glucopyranoside.     

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.     

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 from <Emphasis Type=Italic>Astragalus</Emphasis> and their genins. LXXXV. Structure of cyclomacroside E

The structure of a new cycloartane-type triterpene glycoside, cyclomacroside E, which was isolated from roots of Astragalus macropus Bunge (Leguminosae), was established as 3-O-α-L-rhamnopyranoside,24-O[(β-D-xylopyranosyl)(1→2)-β-D-xylopyranoside]-24R-cycloartan-1α,3β,7β,24,25-pentaol.     

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.     

Triterpene glycosides and their genins from <Emphasis Type=Italic>Astragalus</Emphasis>. LXXXIV. Secomacrogenin B,a new 9,10-<Emphasis Type=Italic>seco</Emphasis>-cycloartane

The structure of a new triterpenoid, secomacrogenin B, which was isolated from Astragalus macropus Bunge (Leguminosae) roots and is 24R-9,10-seco-cycloartan-1(10),9(11)-dien-3β,7β,24,25-tetraol, was elucidated.     

Triterpene Glycosides from <Emphasis Type="Italic">Cussonia paniculata</Emphasis>. II. Acetylated Glycosides from Leaves

Structures of 13 new acetylated triterpene glycosides from leaves of Cussonia paniculata (Araliaceae) were established as 28-O-(2-O-acetyl- and 3-O-acetyl-α-L-rhamnopyranosyl)-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β -D-glucopyranosides of 23-hydroxybetulinic acid (1a and 1b) and hederagenin (2a and 2b), 3-O-α-L-arabinopyranosyl-28-O-(2-O-acetyl- and 3-O-acetyl-a-L-rhamnopyranosyl)-(1→ 4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glycopyranosides of oleanic (3a and 3b) and ursolic (3c and 3d) acids, 3-O-α-L-arabinopyranosyl-28-O-(4-O-acetyl-, 2-O-acetyl-, and 3-O-acetyl-α-L-rhamnopyranosyl)-(1→4)-O-β-D-glucopyranosyl-(1→ 6)-O-β-D-glucopyranosides of hederagenin (4, d5a and 5b), and 3-O-β-D-glucopyranosyl-(1→2)-O-α-L-arabinopyranosyl-28-O-(2-O-acetyl- and 3-O-acetyl-α-L-rhamnopyranosyl)-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D- glucopyranosides of oleanic acid (6a and 6b). The structures of the compounds were established using chemical methods and NMR spectroscopy. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 351–356, July–August, 2005.     

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.     

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.     

Synthesis of Glycosides of Lupane-Type Triterpene Acids

A preparative synthesis of glucosides of the lupane-type triterpene acids betulinic, dihydrobetulinic, betulonic, dihydrobetulonic, and 3,20-dioxo-30-norlupan-28-oic was proposed. Glycosylation of 3-hydroxyacids by -acetobromoglucose (ABG) with Ag₂O was performed in pyridine (Py)to formglycosides at C-28, repeated glycosylation of which by these same reagents but in CH₂Cl₂ generated a glycoside bond at C-3 to form bisglucosides. 28-Glucosides of ketoacids were formed in high yields in both Py and CH₂Cl₂.     

Structural Studies and Biological Activity of Plant Triterpenoids from the <Emphasis Type="Italic">Thalictrum</Emphasis> Genus

Structures and chemical and spectral properties of triterpenoids isolated from plants of the Thalictrum genus were systematized for the first time. Features of ¹³C NMR spectra of cycloartane triterpenoids were discussed. Data for the biological activities of certain cycloartane and oleanane triterpenoids were given.__________Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 97–114, March–April, 2005.     

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.     

Arabinogalactomannan from <Emphasis Type="Italic">Gleditsia macracantha</Emphasis> seeds

A polysaccharide with MW 25,000 consisting of arabinose, galactose, and mannose units in a 1:2.8:3.2 ratio was isolated from Gleditsia macracantha seeds. Chemical and spectral methods established that the polysaccharide was a branched galactomannan with side branches consisting of arabinose units. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 128-130, March-April, 2009.