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

Nobuki Kato; Masayoshi Inada; Hirotaka Sato; Satoko Ito; Mitsuru Shoji; Minoru Ueda

doi:10.1016/j.tetlet.2007.08.058

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

Nobuki Kato, Masayoshi Inada, Hirotaka Sato, Satoko Ito, Mitsuru Shoji, Minoru Ueda

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

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.

Original language	English
Pages (from-to)	7702-7705
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	43
DOIs	https://doi.org/10.1016/j.tetlet.2007.08.058
Publication status	Published - 2007 Oct 22

Keywords

Enantio-differential
Fluorescence-probe
Leaf-closing substance
Nyctinasty
Phyllanthurinolactone

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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@article{d8ad1cdb77574338b69f62dac423481a,

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

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.",

keywords = "Enantio-differential, Fluorescence-probe, Leaf-closing substance, Nyctinasty, Phyllanthurinolactone",

author = "Nobuki Kato and Masayoshi Inada and Hirotaka Sato and Satoko Ito and Mitsuru Shoji and Minoru Ueda",

note = "Funding Information: 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).",

year = "2007",

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doi = "10.1016/j.tetlet.2007.08.058",

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AU - Kato, Nobuki

AU - Inada, Masayoshi

AU - Sato, Hirotaka

AU - Ito, Satoko

AU - Shoji, Mitsuru

AU - Ueda, Minoru

N1 - Funding Information: 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).

PY - 2007/10/22

Y1 - 2007/10/22

N2 - 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.

AB - 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.

KW - Enantio-differential

KW - Fluorescence-probe

KW - Leaf-closing substance

KW - Nyctinasty

KW - Phyllanthurinolactone

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

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ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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