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     

Triterpene Glycosides of Tetrapanax papyriferum. IV. Acidic Glycosides from Stem Bark of T. Papyriferum

Twelve acidic triterpene glycosides of oleanolic acid, two of which were new, were isolated from stem bark of Tetrapanax papyriferum C. Koch (Araliaceae). The structures of these compounds were established using chemical methods and NMR spectroscopy.     

Triterpene Glycosides of Tetrapanax papyriferum. I. Isolation and Structure of Glycosides St-H2 and St-I2 from Stem Bark

Stem bark ofTetrapanax papyriferumC. Koch., Araliaceae, yielded new triterpene glycosides 28-O--L-rhamnopyranosyl-(14)-O-(6-O-acetyl--D-glucopyranosyl)-(16)-O--D-glucopyranosyl esters of the 3-O-[-D-glucopyranosyl-(13)-[-D-galactopyranosyl-(12)]-O--L-arabinopyranosides of oleanolic and echinocystic acids. The structures of these substances were established using chemical and physicochemical methods     

Triterpenoid Glycosides of Scheffleropsis angkae. III. Structure of Glycoside L-I1

A new triterpenoid glycoside L-I ₁ , the 28-O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl ester of 3,23,27-trihydroxylup-20(29)-en-28-oic acid, is isolated from the leaves ofScheffleropsis angkae(Araliaceae). Its structure is established by chemical methods and various NMR techniques ( ¹ H, ¹³ C, APT, COSY, TOCSY, ROESY, HSQC, HMBC). 3,23,27-Trihydroxylup-20(29)-en-28-oic acid is a new triterpenoid aglycone     

Triterpene Glycosides of Tetrapanax papyriferum. II. Isolation and Structure Determination of Glycosides St-E2, St-F2, St-J2, and St-K2 from Stem Bark

Stem bark ofTetrapanaxpapyriferum yielded the new triterpene glycosides 3-O-[-D-glucopyranosyl-(13)]--D-galactopyranosyl-(12)-O--L-arabinopyranosides of oleanolic and echinocystic acids and their 28-O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl esters. Their structures were established using chemical and physicochemical methods     

Triterpene Glycosides of Fatsia japonica. VI. Structures of Glycosides D3a and D3b

Seeds of Fatsia japonica (Araliaceae) yielded the new glycosides of gypsogenin: 3-O--D-glucopyranosyl-(12)-O--D-glucopyranoside and 3-O--D-galactopyranosyl-(12)-O--D-glucopyranoside. The structures of these compounds were established by chemical methods and NMR spectroscopy.     

Triterpene glycosides from Cussonia paniculata. III. Structure of glycosides I1, I2, J1a, J1b, J2, K, L1, and L2 from C. paniculata leaves

Structures of eight triterpene glycosides, of which the 28-O-(2-O-acetyl-and 3-O-acetyl-α-L-rhamnopyranosyl)-(1→4)-O-β-D-glucopyranosyl-(1→ 6)-O-β-D-glucopyranosyl esters of hederagenin 3-O-β-D-glucopyranosyl-(1→ 2)-O-α-L-arabinopyranoside (J_1a and J_1b) were new, from Cussonia paniculata (Araliaceae) leaves were established using chemical and NMR spectroscopic methods. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 149–152, March–April, 2006.     

Triterpene Glycosides from Cussonia paniculata. I. Isolation and Structure Determination of Glycosides A, B1, B2, C, D, G2, H1, and H2 from Leaves of Cussonia paniculata

The 3-O-β-D-glucopyranoside of β-sitosterol (1) and the known triterpene glycosides 3-O-α-L-arabinopyranosides of oleanolic (2a) and ursolic (2b) acids and hederagenin (3), 3-O-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosideofoleanolic acid (4), 3-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosides of oleanolic (5a) and ursolic (5b) acids and the newglycoside 28-O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranoside of 23-hydroxyursolic acid (6) were isolated from leaves of Cussonia paniculata (Araliaceae). Their structures were established using chemical methods and NMR spectroscopy.__________Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 160–163, March–April, 2005.     

Triterpene glycosides from Kalopanax septemlobum. VI. Glycosides from leaves of Kalopanax septemlobum var. typicum introduced to crimea

Thirteen known glycosides of hederagenin and oleanolic acid and the three new triterpene glycosides of oleanolic acid-28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester 3-O-β-D-glucopyranosyl-(1→4)-O-β-D-xylopyranosyl-(1→ 3)-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranoside of oleanolic acid and the 28-O-α-L-rhamnopyranosyl-(1→4)-O-6-O-acetyl-β-D-glucopyranosyl-(1→ 6)-O-β-D-glucopyranosyl esters 3-O-β-D-xylopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranoside of oleanolic acid and 3-O-β-D-glucopyranosyl-(1→4)-O-β-Dxylopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→ 2)-O-α-L-arabinopyranoside of oleanolic acid were isolated from leaves of Kalopanax septemlobum var. typicum introduced to Crimea. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 40–43, January–February, 2006.     

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.     

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.     

Triterpene Glycosides from Kalopanax septemlobum. III. Glycosides D2, I1, and K1 from Leaves of Kalopanax septemlobum var. maximowiczii Introduced in Crimea

The new caffeylated triterpene glycosides hederagenin 3-O-(6-O-caffeyl-β-D-glucopyranosyl)-(1→4)-O-β-D-xylopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→2)-O-β-L-arabinopyranoside and its 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl and 28-O-α-L-rhamnopyranosyl-(1→4)-O-6-O-acetyl-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl esters were isolated from leaves of Kalopanax septemlobum var. maximowiczii introduced in Crimea. The structures of these compounds were established using chemical methods and NMR spectroscopy.__________Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 263–267, May–June, 2005.     

The Effect of Triterpene Glycosides on Electrical Activity Changes of Identified Mollusk Neurons

The effect of mono- and bisdesmoside triterpene glycosides on the background activity of the grape snail Helix pomatia identified neurons was studied. Monodesmoside glycosides at concentrations of 10^-3-10^-4 M elicit stable hyperpolarization of neurons by increasing the membrane permeability for K⁺ ions. At concentrations of 10^-5-10^-7 M, they briefly change the neuronal impulse activity. The type of monodesmoside triterpene glycoside activity on neurons depends on the structure of the hydrocarbon. The glycoside effect on neuron membranes is related to the hemolytic activity     

TRITERPENE GLYCOSIDES FROM Tetrapanax papyriferum. III. MINOR MONODESMOSIDE GLYCOSIDES FROM STEM BARK

Minor monodesmoside triterpene glycosides St-A, St-B, St-C ₁ , St-D ₁ , St-C ₂ , and St-D ₂ were isolated from stem bark ofTetrapanax papyriferumC. Koch (Araliaceae). The structures of oleanolic and echinocystic acid 3-O--L-arabinopyranosides, oleanolic and echinocystic acid 3-O--D-glucopyranosyl-(13)-O--L-arabinopyranosides, and oleanolic and echinocystic acid 3-O--D-galactopyranosyl-(12)-O--L-arabinopyranosides, respectively, were proposed. Glycosides St-C ₂ , St-D ₁ , and St-D ₂ are new triterpene glycosides. The structures of the isolated compounds were established using chemical methods and NMR spectroscopy.     

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 from Kalopanax septemlobum. 1. Glycosides A, B, C, F, G1, G2, I2, H, and J from Leaves of Kalopanax septemlobum var. Maximowichii Introduced to Crimea

Eight known glycosides of hederagenin and the new triterpene glycoside 3-O-β-D-xylopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1→4)-O-6-O-acetyl-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester of hederagenin were isolated by chromatographic methods from leaves of Kalopanax septemlobum var. maximowichii introduced to Crimea. The known 3-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1→4)-O-6-O-acetyl-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester of hederagenin was observed for the first time in Kalopanax septemlobum.__________Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 156–159, March–April, 2005.     

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 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 from <Emphasis Type="Italic">Kalopanax septemlobum</Emphasis>. II. Glycosides E,K, and L from Leaves of <Emphasis Type="Italic">Kalopanax septemlobum</Emphasis> var. <Emphasis Type="Italic">maximowiczii</Emphasis> Introduced to Crimea

The known hederagenin 3-O-β-D-glucopyranosyl-(1→4)-O-β-D-xylopyranosyl-(1→ 3)-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranoside (sapindoside C) and its 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl and 28-O-α-L-rhamnopyranosyl-(1→4)-O-6-O-acetyl-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl esters, new triterpene glycosides, were isolated from leaves of Kalopanax septemlobum var. maximowiczii introduced to Crimea. The structures of these compounds were established using chemical methods and two-dimensional NMR spectroscopy.__________Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 260–262, May–June, 2005.     

Triterpene glycosides ofScheffleropsis angkae. I. Structure of glycosides L-B1, L-B2, L-H1, and L-H2

The structures of four triterpene glycosides from the leaves ofScheffleropsis angkae (Araliaceae) are found by chemical methods and NMR spectroscopy to be the 3-O--L-arabinopyranosides of oleanic and ursolic acids and their 28-O--L-rhamnopyranosyl-(14)-O--gentiobiosyl esters, which are designated L-B₁, L-B₂, L-H₁, and L-H₂, respectively. The glycoside L-H₂ is new.Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 136–138, March–April, 2000.