Elsevier

Tetrahedron Letters

Volume 48, Issue 43, 22 October 2007, Pages 7702-7705
Tetrahedron Letters

Enantio-differential approach using fluorescence-labeled phyllanthurinolactone, a leaf-closing factor of Phyllanthus urinaria L.

https://doi.org/10.1016/j.tetlet.2007.08.058Get rights and content

Abstract

We report here the synthesis of enantio-pair-type fluorescence-labeled probes based on phyllanthurinolactone (1), which is a leaf-closing substance of Phyllanthus urinaria L. Moreover, the application of an enantio-differential approach to distinguish between specific and nonspecific binding of ligands and receptors was performed. Fluorescence studies using a natural-type probe 6 and a nonnatural-type probe 7 revealed that the target cell for 1 is a motor cell. Furthermore, our results lead to the suggestion that some receptors, which recognize the stereochemistry of the aglycon of 1, exist on the plasma membrane of the motor cell, as do leaf-opening substances.

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Acknowledgment

This work was supported by Grant-in-Aid for Scientific Research on Priority Area 16073216 from the Ministry of Education, Science, Sports and Culture (MEXT).

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