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Molecules 2013, 18(12), 15193-15206; doi:10.3390/molecules181215193

Facile Synthesis of the Naturally Cytotoxic Triterpenoid Saponin Patrinia-Glycoside B-II and Its Conformer

Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China
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Received: 30 October 2013 / Revised: 2 December 2013 / Accepted: 3 December 2013 / Published: 10 December 2013
(This article belongs to the Section Medicinal Chemistry)
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Abstract

The first chemical synthesis of the natural triterpenoid saponin Patrinia-glycoside B-II, namely oleanolic acid 3-O-α-L-rhamnopyranosyl-(1→2)-[β-D-gluco-pyranosyl-(1→3)]-α-L-arabinopyranoside, has been accomplished in a linear 11-step sequence 11 with 9.4% overall yield. The abnormal 1C4 conformation of the arabinose residue was found to occur via conformational fluctuation during preparation of the intermediates. Molecular mechanism and quantum chemistry calculations showed that Patrinia-glycoside B-II and its conformer 1 cannot interconvert under normal conditions. Preliminary structure-activity relationships studies indicated that the 4C1 chair conformation of the arabinose residue in the unique α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl disaccharide moiety is one of the chief positive factors responsible for its cytotoxic activity against tumors. View Full-Text
Keywords: oleanolic acid saponin; stepwise glycosylation; tumor cytotoxicity; chair conformational fluctuation oleanolic acid saponin; stepwise glycosylation; tumor cytotoxicity; chair conformational fluctuation
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Ren, L.; Liu, Y.-X.; Lv, D.; Yan, M.-C.; Nie, H.; Liu, Y.; Cheng, M.-S. Facile Synthesis of the Naturally Cytotoxic Triterpenoid Saponin Patrinia-Glycoside B-II and Its Conformer. Molecules 2013, 18, 15193-15206.

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