Next Article in Journal
Repetitive Two-Step Method for o,o,p- and o,p-Oligophenylene Synthesis through Pd-Catalyzed Cross-Coupling of Hydroxyterphenylboronic Acid
Previous Article in Journal
Efficient PPA-SiO2-catalyzed Synthesis of β-enaminones Under Solvent-Free Conditions
Open AccessArticle

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
*
Authors to whom correspondence should be addressed.
Molecules 2013, 18(12), 15193-15206; https://doi.org/10.3390/molecules181215193
Received: 30 October 2013 / Revised: 2 December 2013 / Accepted: 3 December 2013 / Published: 10 December 2013
(This article belongs to the Section Medicinal Chemistry)
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
Show Figures

Figure 1

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Article Access Map by Country/Region

1
Only visits after 24 November 2015 are recorded.
Search more from Scilit
 
Search
Back to TopTop