2014Chemistry & BiodiversityRequires access

Oleanane‐Type Glycosides from Tremastelma palaestinum (L.) Janchen

Gökhan Şenel, Derya Gülcemal, Milena Masullo, Sonia Piacente, Tamer Karayıldırım

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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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What this paper is about

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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Available 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.

Key concepts: Chemistry, Oleanane, Hederagenin, Glycoside, Oleanolic acid, Stereochemistry, Phytochemical, Triterpene

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