Enantio-differential approach to identify the target cell for glucosyl jasmonate-type leaf-closing factor, by using fluorescence-labeled probe compounds

Nakamura, Yoko; Miyatake, Ryoji; Matsubara, Akira; Kiyota, Hiromasa

doi:10.1016/j.tet.2006.06.092

Cited by 36 publications

(19 citation statements)

References 18 publications

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“…We have studied the mechanism for nyctinastic leafmovement by using LCF as a molecular probe. 11) We have reported in previous papers the synthesis of LCF 1. 11,12) However, the low yield prevented the structure-activity relationship (SAR) to be studied by using 1.…”

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confidence: 99%

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Synthesis and Bioactivity of Potassium β-D-Glucopyranosyl 12-Hydroxy Jasmonate and Related Compounds

Nakamura

Miyatake

Inomata

2008

Bioscience, Biotechnology, and Biochemistry

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Albizzia saman, a leguminous plant, is known to open its leaves in the daytime and sleep at night with the leaves folded. -D-Glucopyranosyl 12-hydroxyjasmonate (1) was isolated as an endogenous chemical factor controlling this leafmovement. We developed a concise synthesis of optically pure (À)-1 in 9 steps from (+)-2 with a total yield of 58%. Similarly, such analogs of 1 as epi-LCF (13), enantiomer (14), and galactoside (19) were synthesized for a structure activity relationship (SAR) study. The results of this SAR study strongly suggest that the mechanism for the leaf-closing activity of 1 would be different from that of methyl jasmonate, and also suggest the involvement of a different kind of target protein which recognizes the trans-isomer of a jasmonate derivative.

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“…11) We have reported in previous papers the synthesis of LCF 1. 11,12) However, the low yield prevented the structure-activity relationship (SAR) to be studied by using 1. We report in this paper an improved synthesis of 1 and related compounds, including enantiomer 14, and SAR studies using them.…”

mentioning

confidence: 99%

Synthesis and Bioactivity of Potassium β-D-Glucopyranosyl 12-Hydroxy Jasmonate and Related Compounds

Nakamura

Miyatake

Inomata

2008

Bioscience, Biotechnology, and Biochemistry

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“…We optically resolved commercially available methyl jasmonate ((±)-3) in order to obtain both enantiomers of the aglycone with a high degree of optical purity in excess of 99.5%ee. These were subsequently introduced onto separate fluorescent probes, and fluorescent probes with 1 as the base were synthesized (17). The probe with natural configuration (4) exhibited leaf-closing activity in A. saman, but the enantiomer probe (5) exhibited no activity.…”

Section: C-2 Search For Lcf Target Cell Using An Enantiodifferentialmentioning

confidence: 99%

Chemical Biology of Glycoside-Type Bioactive Substances Controlling Nyctinastic Movement in Leguminous Plants

Manabe

Inomata

2010

TIGG

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Leguminous plants open their leaves during the day and close them at night as if sleeping, a type of movement that follows circadian rhythms and is known as nyctinastic movement. This phenomenon is controlled by two endogenous bioactive substances that exhibit opposing activities: LeafOpening Factor (LOF), which opens the leaves, and LeafClosing Factor (LCF), which closes them. The authors have carried out chemical biological research using these bioactive substances in order to clarify the mechanisms of nyctinastic movement. Here, we report on the detection and identification of the target proteins of these compounds using original methodology.

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“…We revealed that these compounds are common leaf-movement factors 9,10 among Albizzia plants [16,21]. We developed molecular probes consisting of modified leaf-movement factors of Albizzia plants in order to identify their target cells [27][28][29][30]. We conducted a double fluorescencelabeling study using FITC-labeled leaf-closing factor 13 and rhodamine-labeled leaf-opening factor 12 (Fig.…”

Section: Molecular Probes For Molecular Mechanism Of Nyctinastymentioning

confidence: 99%

Endogenous factors involved in the regulation of movement and "memory" in plants

Nakamura¹,

Okada²

2007

Pure and Applied Chemistry

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The bioorganic basis of plant movement in two plant systems is described in this article: the circadian rhythmic leaf movement known as nyctinasty and trap movement in the Venus flytrap. The bioactive substances responsible for plant movement, the chemical mechanism of the rhythm, and studies on the key protein controlling nyctinasty are presented.The nyctinastic leaf movement is induced by a pair of leaf-movement factors, and one of each pair is a glucoside. There are two key proteins that are involved in the control of nyctinasty. One is β-glucosidase: a biological clock regulates the activity of β-glucosidase, which deactivates the glucoside-type leaf-movement factor, controlling the balance in the concentrations of the leaf-closing and -opening factors. The other is the specific receptor for each leaf-movement factor: the genuine target cell for each leaf-movement factor is confirmed to be a motor cell from leaflet pulvini, and the specific receptors that regulate the turgor of motor cells are localized in the membrane fraction.The article also discusses the isolation of the "memory" substance from the Venus flytrap and presents a mechanism for this action.

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Enantio-differential approach to identify the target cell for glucosyl jasmonate-type leaf-closing factor, by using fluorescence-labeled probe compounds

Cited by 36 publications

References 18 publications

Synthesis and Bioactivity of Potassium β-D-Glucopyranosyl 12-Hydroxy Jasmonate and Related Compounds

Synthesis and Bioactivity of Potassium β-D-Glucopyranosyl 12-Hydroxy Jasmonate and Related Compounds

Chemical Biology of Glycoside-Type Bioactive Substances Controlling Nyctinastic Movement in Leguminous Plants

Endogenous factors involved in the regulation of movement and "memory" in plants

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