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Triterpene glycosides ofHedera canariensis. I. Structures of glycosides L-A, L-B1, L-B2, L-C, L-D, L-E1 1, L-G1, L-G2, L-G3, L-G4, L-H1, L-H2, AND L-I1 from the leaves ofHedera canariensis

Abstract

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.

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Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 377–383, May–June, 1996. Original article submitted December 3, 1995.

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Grishkovets, V.I., Sidorov, D.Y., Yakovishin, L.A. et al. Triterpene glycosides ofHedera canariensis. I. Structures of glycosides L-A, L-B1, L-B2, L-C, L-D, L-E1 1, L-G1, L-G2, L-G3, L-G4, L-H1, L-H2, AND L-I1 from the leaves ofHedera canariensis . Chem Nat Compd 32, 360–365 (1996). https://doi.org/10.1007/BF01372340

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Keywords

  • Organic Chemistry
  • Glycoside
  • Chemical Transformation
  • Oleanolic Acid
  • Hederagenin