V. Ya. Chirva

Triterpene glycosides ofHedera canariensis. I. Structures of glycosides L-A, L-B1, L-B2, L-C, L-D, L-E11, L-G1, L-G2, L-G3, L-G4, L-H1, L-H2, AND L-I1 from the leaves ofHedera canariensis

From the leaves of Algerian ivyHedera canariensis Willd. (fam. Aralaceae) we have isolated 13 triterpene glycosides: the 3-O-α-L-arabinopyranosides of oleanolic acid (A), of echinocystic acid (B1), and of hederagenin (B2); the 3-O-[O-α-L-rhamnopyranosyl-(→2)-α-L-arabinopyranoside]s of oleanolic acid (C), of echinocystic acid (D), and of hederagenin (E1); the 3-O-α-L-rhamnopyranoside] 28-O-[O-α-L-rhamnopyranosyl-(1→4)-β-gentiobioside of hederagenin (G1); the 3-O-[O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside] 28-O-β-gentiobioside of hederagenin (G3); the 3-O-[O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside] 28-O-[O-α-L-rhamnopyranosyl-(1→4)-β-gentiobioside]s of oleanolic acid (G2), of echinocystic acid (H1), and of hederagenin (H2); the 3-O-[O-α-L-rhanmopyranosyl-(1→2)-β-D-glucopyranoside] 28-O-(O-α-L-rhamno-pyranosyl-(1→4)-β-gentiobioside] of hederagenin (H2); and the 3-O-(O-α-L-rhamnopyranosyl-(1→2)-O-gentiobiosyl)-O-(1→4)-α-L-rhamnopyranosyl-(1→2)-a-L-arabinopyranoside] of hederagenin (G4). The structures of the substances isolated have been established on the basis of chemical transformations and13C NMR spectroscopy.

Triterpene glycosides ofSapindus mukorossi

ConclusionsThe structure of sapindoside D, which is a hexaoside of hederagenin, has been shown.

Triterpene glycosides ofHedera taurica I. Structure of tauroside E from the leaves ofHedera taurica

The structure of taurorisde E — the predominating triterpene glycoside from the leaves of Crimean ivy,Hedera taurica Carr. has been established by1H and13C NMR spectroscopy using nuclear Overhauser effects. It is 3-O-[O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl]hederagenin.

Triterpene glycosides ofScheffleropsis angkae. II. Structure of glycosides L-E1, L-E2, L-K1, and L-K2

The structures of four triterpene glycosides from leaves ofScheffleropsis angkae (Araliaceae) are established using chemical and NMR methods. The structures 3-O-β-D-glucopyranosyl-(1-3)-O-α-L-arabinopyranosides of oleanic and ursolic acids and their 28-O-α-L-rhamnopyranosyl-(1-4)-O-β-gentiobiosyl ethers are proposed for L-E1, L-E2, L-K1, and L-K2, respectively. L-K1 and L-K2 are new triterpene glycosides.

Triterpene glycosides fromHedera canariensis VI. Structure of L-G1 and L-G1b glycosides from leaves of canary ivy

Two new minor triterpene glycosides L-G1, and L-G2b, the 3-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1→4)-O-β-D-gentiobiosyl and 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 esters of 30-norhederagenin, respectively, are isolated from the leaves of canary ivy (Hedera canariensis Willd.). The structures of the glycosides are found by chemical methods and1H and13C NMR spectroscopy.

Triterpene glycosides ofHedera taurica XV. Structures of glycosides St-I3, St-I4a, St-I4b, and St-I5 from the stems of Crimean ivy

From the stems of Crimean ivyHedera taurica Carr. (fam. Araliaceae) we have isolated the new triterpene glycosides St-I3, St-I5, and St-I4a, which are, respectively, the 3–0-β-D-glucopyranoside 28-O-[O-α-L-rhamnopyranosyl-(1→4)-O-(6-O-acetyl-β-D-glucopyranosyl)-(1→6)-O-β-D-glucopyranosides] of oleanolic acid and of hederagenin and the 3-O-β-D-glucopyranuronoside 28-O-β-gentiobioside of oleanolic acid, and also the previously known 3-O-[O-β-D-galactopyranosyl-(1→2)-β-D-glucopyranuronoside 28-O-β-D-glucopyranoside] of oleanolic acid (glycoside Rb-4).

Triterpene glycosides ofHedera taurica XIV. Structures of glycosides St-G0–2, St-J, and St-K from the stems of Crimean ivy

The previously known glycosides 3-O-α-L-arabinopyranosyl-28-O-[α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl]hederagenin and 3-O-[α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl]hederagenin and the new triterpene glycoside tauroside St-H1 — 3-O-β-D-glucopyransyl-28-O-[α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl]hederagenin — have been isolated from the stems ofHedera taurica Carr.

Steroidal glycosides from Allium cyrillii bulbs

Two spirostanol saponins, one of which was a new compound, were isolated among the steroidal glycosides of Allium cyrillii Ten. Bulbs. The structures of these glycosides were established using chemical and spectral analytical methods as β-D-glycopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 3)]-β-D-glucopyranosyl-(1 → 4)β-D-galactopyranosyl-(1 → 3)-(25R)-5α-spirostan-2α,3β-diol and β-D-glucopyranosyl-(1 → 2)-[4-O-(3hydroxy-3-methylglutaryl)-β-D-xylopyranosyl-(1 → 3)]-β-D-glucopyranosyl-(1 → 4)-β-D-galactopyranosyl(1 → 3)-(25R)-5α-spirostan-2α,3β-diol.

Triterpene glycosides ofHedera canariensis III. Determination of the structures of glycosides L-F1, L-F2, and L-I2 from the leaves of Algerian ivy

The leaves of Algerian ivyHedera canariensis Willd. (Araliaceae) have yielded two new triterpene glycosides — caulophyllogenin 3-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranoside (L-F2) and its 28-O-α-L-rhamnopyranosyl-(1→4)-O-β-D-gentiobiosyl ester (L-I2) - and also the previously known hederagenin 3-O-α-L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranoside (L-F1). The structures of the glycosides were established on the basis of chemical transformations and1H and13C NMR spectroscopy.

Triterpene glycosides ofHedera taurica XVI. Structures of glycosides St-A, St-B1, St-B2, St-C, St-D1, St-D2, St-E, St-F1, and St-F2 from the stems of Crimean ivy

From the stems of Crimean ivyHedera taurica Carr. (fam. Araliaceae) we have isolated previously known glycosides of oleanolic acid — the 3-O-[O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside], the 3-O-β-D-glucopyranuronoside, and the 3-O-[O-β-D-galactopyranosyl-(1→2)-β-D-glucopyranuronoside]; known glycosides of hederagenin — the 3-O-α-L-arabinopyranoside, the 3-β-D-glucopyranoside, the 3-O-[O-β-D-glucopyranosyl-(1→2)-O-α-L-arabinopyranoside], and the 3-O-β-D-glucopyranuronoside; and also the new triterpene glycoside St-D2, hederagenin 3-O-[O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside].