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BioEssays Volume 34, Issue 3. Saadi Khochbin Corresponding Author E-mail address: First published: Read the full text.

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Volume 34 , Issue 3 March Pages Related Information. Email or Customer ID. Forgot password? The main bioactive constituents of Kadsura longipedunculata comprise highly oxygenated triterpenoids.

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For such compounds, the absolute configuration influences the bioactivities, and hence its unambiguous determination is essential. In this work, the absolute configurations of three highly oxygenated schiartane-type nortriterpenoids were unequivocally assigned using X-ray, ECD, and J-based configuration analysis and HSQC overlay data.

Results Three new highly oxygenated triterpenoids, micrandilactone I 1 , micrandilactone J 2 , and 22,diepi- micrandilactone J 3 were isolated. Micrandilactone I 1 and 22,di-epi-micrandilactone J 3 showed moderate hepatoprotective activity against APAP-induced toxicity in HepG2 cells with cell survival rates of General significance This is the first comprehensive stereochemical assignment of a non-crystalline schiartanetype nortriterpenoid like 3.

This general protocol may contribute towards solving the problems hampering the assignment of the absolute configurations of other members of this class of nortriterpenoids.

Introduction Highly oxygenated triterpenoids isolated from plants of the genera Schisandra and Kadsura have revealed a variety of important biological activities including potent anti-HIV [ 1 ], anti-HBV [ 2 ], and cytotoxic properties [ 3 — 6 ]. Their 2D structures and relative configurations have been successfully elucidated by NMR spectroscopic methods.

Assignment of their absolute configurations is critical since it influences their bioactivities and is essential for future efforts focused on synthesis and medicinal chemistry applications. For the absolute configuration, X-ray diffraction and electric circular dichroism ECD methods have often been used.

However, even with these advanced techniques, it has proven difficult to determine the absolute configuration for the schiartane-type nortriterpenoids due to the presence of 12 non-contiguous stereogenic centers as well as conformationally flexible side chains.

Herein, we report an integrated analysis to comprehensively assign the absolute configurations of schiartane-type nortriterpenoids using a combination of methods. Material and methods 2.Edited and Translated by Stephen M.

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