Oleanane‐Type Glycosides from Tremastelma palaestinum (L.) Janchen
Gökhan Şenel, Derya Gülcemal, Milena Masullo, Sonia Piacente, Tamer Karayıldırım
Abstract
Gökhan Şenel, Derya Gülcemal, Milena Masullo, Sonia Piacente, Tamer Karayıldırım
Abstract
Three new oleanane-type glycosides, 1-3, were isolated from the whole plant of Tremastelma palaestinum (L.) Janchen, along with eight known triterpene glycosides. The structures of the new compounds were established as 3-O-[β-d-glucopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→3)-β-d-glucopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl]hederagenin (1), 3-O-[β-d-glucopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→3)-β-d-glucopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl]hederagenin 28-O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl ester (2), and 3-O-[α-l-rhamnopyranosyl-(1→3)-β-d-glucopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl]oleanolic acid 28-O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl ester (3) by using 1D- and 2D-NMR techniques and mass spectrometry. This is the first report on the phytochemical investigation of a species belonging to Tremastelma genus.
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Three new oleanane-type glycosides, 1-3, were isolated from the whole plant of Tremastelma palaestinum (L.) Janchen, along with eight known triterpene glycosides. The structures of the new compounds were established as 3-O-[β-d-glucopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→3)-β-d-glucopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl]hederagenin (1), 3-O-[β-d-glucopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→3)-β-d-glucopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl]hederagenin 28-O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl ester (2), and 3-O-[α-l-rhamnopyranosyl-(1→3)-β-d-glucopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl]oleanolic acid 28-O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl ester (3) by using 1D- and 2D-NMR techniques and mass spectrometry. This is the first report on the phytochemical investigation of a species belonging to Tremastelma genus.
Key concepts: Chemistry, Oleanane, Hederagenin, Glycoside, Oleanolic acid, Stereochemistry, Phytochemical, Triterpene