Synthesis and biological effects of aromatic analogs of abscisic acid

Shmuel Bittner; Malka Gorodetsky; Irit Har-Paz; Yosef Mizrahi; Amos E. Richmond

doi:10.1016/S0031-9422(00)94349-8

Synthesis and biological effects of aromatic analogs of abscisic acid

Shmuel Bittner, Malka Gorodetsky, Irit Har-Paz, Yosef Mizrahi, Amos E. Richmond

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

18 Scopus citations

Abstract

Thirty six different 3-methyl-5-aryl-2,4-pentadienoic acids and esters were synthesized using the Reformatsky and Wittig reactions. The different geometrical isomers were conveniently separated by the dry column technique. Assignment of configuration of the pentadienoic side chain was based on NMR and UV properties. The biological activities of the aromatic analogs of ABA were determined in four bioassays. Most of the analogs were less active than the natural hormone. Only 3-methyl-5-p-chlorophenyl Δ²-trans, Δ⁴-trans-pentadienoic acid exhibited high ABA-like activity in all four bioassays.

Original language	English
Pages (from-to)	1143-1151
Number of pages	9
Journal	Phytochemistry
Volume	16
Issue number	8
DOIs	https://doi.org/10.1016/S0031-9422(00)94349-8
State	Published - 1 Jan 1977

Keywords

3-methyl-5-aryl-2,4-pentadienoic acids
Abscisic acid
acceleration of Tropaeolum leaf discs senescence
biological activity
germination of lettuce seed
inhibition of transpiration.
inhibition of wheat coleoptile elongation

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Plant Science
Horticulture

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10.1016/S0031-9422(00)94349-8

Cite this

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title = "Synthesis and biological effects of aromatic analogs of abscisic acid",

abstract = "Thirty six different 3-methyl-5-aryl-2,4-pentadienoic acids and esters were synthesized using the Reformatsky and Wittig reactions. The different geometrical isomers were conveniently separated by the dry column technique. Assignment of configuration of the pentadienoic side chain was based on NMR and UV properties. The biological activities of the aromatic analogs of ABA were determined in four bioassays. Most of the analogs were less active than the natural hormone. Only 3-methyl-5-p-chlorophenyl Δ2-trans, Δ4-trans-pentadienoic acid exhibited high ABA-like activity in all four bioassays.",

keywords = "3-methyl-5-aryl-2,4-pentadienoic acids, Abscisic acid, acceleration of Tropaeolum leaf discs senescence, biological activity, germination of lettuce seed, inhibition of transpiration., inhibition of wheat coleoptile elongation",

author = "Shmuel Bittner and Malka Gorodetsky and Irit Har-Paz and Yosef Mizrahi and Richmond, {Amos E.}",

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doi = "10.1016/S0031-9422(00)94349-8",

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T1 - Synthesis and biological effects of aromatic analogs of abscisic acid

AU - Bittner, Shmuel

AU - Gorodetsky, Malka

AU - Har-Paz, Irit

AU - Mizrahi, Yosef

AU - Richmond, Amos E.

PY - 1977/1/1

Y1 - 1977/1/1

N2 - Thirty six different 3-methyl-5-aryl-2,4-pentadienoic acids and esters were synthesized using the Reformatsky and Wittig reactions. The different geometrical isomers were conveniently separated by the dry column technique. Assignment of configuration of the pentadienoic side chain was based on NMR and UV properties. The biological activities of the aromatic analogs of ABA were determined in four bioassays. Most of the analogs were less active than the natural hormone. Only 3-methyl-5-p-chlorophenyl Δ2-trans, Δ4-trans-pentadienoic acid exhibited high ABA-like activity in all four bioassays.

AB - Thirty six different 3-methyl-5-aryl-2,4-pentadienoic acids and esters were synthesized using the Reformatsky and Wittig reactions. The different geometrical isomers were conveniently separated by the dry column technique. Assignment of configuration of the pentadienoic side chain was based on NMR and UV properties. The biological activities of the aromatic analogs of ABA were determined in four bioassays. Most of the analogs were less active than the natural hormone. Only 3-methyl-5-p-chlorophenyl Δ2-trans, Δ4-trans-pentadienoic acid exhibited high ABA-like activity in all four bioassays.

KW - 3-methyl-5-aryl-2,4-pentadienoic acids

KW - Abscisic acid

KW - acceleration of Tropaeolum leaf discs senescence

KW - biological activity

KW - germination of lettuce seed

KW - inhibition of transpiration.

KW - inhibition of wheat coleoptile elongation

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DO - 10.1016/S0031-9422(00)94349-8

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SN - 0031-9422

VL - 16

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EP - 1151

JO - Phytochemistry

JF - Phytochemistry

IS - 8

ER -

Synthesis and biological effects of aromatic analogs of abscisic acid

Abstract

Keywords

ASJC Scopus subject areas

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