Journal of Agricultural and Food Chemistry, volume 53, issue 25, pages 9775-9780
Salicylate Activity. 3. Structure Relationship to Systemic Acquired Resistance
F. Paul Silverman
1
,
Peter D. Petracek
1
,
Daniel F Heiman
1
,
Christina M Fledderman
1
,
Prem Warrior
1
1
Valent BioSciences Corporation, 6131 Oakwood Road, Long Grove, Illinois 60047
|
Publication type: Journal Article
Publication date: 2005-11-15
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 6.1
ISSN: 00218561, 15205118
General Chemistry
General Agricultural and Biological Sciences
Abstract
Salicylic acid (2-hydroxybenzoic acid; SA) is a primary signal inducing plant defenses against pathogens. This plant disease resistance, known as systemic acquired resistance (SAR), is an attractive target for the development of new plant protection agents. SAR induction is a multistep process that includes accumulation of pathogenesis-related (PR) proteins. The structure-activity profile of salicylates and related compounds has been evaluated using an inducible PR protein (PR-1a) and plant resistance to tobacco mosaic virus (TMV) as markers. Among the 47 selected monosubstituted and multiple-substituted salicylate derivatives tested, all 8 derivatives that induced more PR-1a protein than SA were fluorinated or chlorinated in the 3- and/or 5-position (3,5-difluorosalicylate > 3-chlorosalicylate > 5-chlorosalicylate > 3,5-dichlorosalicylate > 3-chloro-5-fluorosalicylate > 3-fluorosalicylate > 3-fluoro-5-chlorosalicylate > 3,5-dichloro-6-hydroxysalicylate > SA). In general, substitutions for or on the 2-hydroxyl group or at the 4-position of the ring reduced or eliminated PR-1a protein induction. In contrast, substitutions in positions ortho (3-position) or para (5-position) to the hydroxyl group with electron-withdrawing groups other than chlorine or fluorine decreased induction, and electron-donating groups in these positions also had a deleterious effect on PR-1a induction. PR-1a protein accumulation and reduction in TMV lesion diameter exhibited a log-linear relationship. The seven salicylate derivatives that were the most active TMV resistance inducers were all halogenated in the 3- and/or 5-position (3-chlorosalicylate > 3,5-difluorosalicylate > 3,5-dichloro-6-hydroxysalicylate > 3,5,6-trichlorosalicylate > 5-chlorosalicylate > 5-fluorosalicylate > 3,5-dichlorosalicylate > 4-fluorosalicylate > 3-fluorosalicylate > 3-chloro-5-fluorosalicylate > 4-chlorosalicylate > SA). The correlation between PR-1a protein induction and resistance to TMV confirms the value of using PR-1a induction as a screening tool for developing new plant disease control agents.
Top-30
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1 publication, 3.45%
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3
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Citations by publishers
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2
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10
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10 publications, 34.48%
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Springer Nature
2 publications, 6.9%
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2 publications, 6.9%
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1 publication, 3.45%
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Cold Spring Harbor Laboratory
1 publication, 3.45%
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The Company of Biologists
1 publication, 3.45%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 3.45%
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2
4
6
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10
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Silverman F. P. et al. Salicylate Activity. 3. Structure Relationship to Systemic Acquired Resistance // Journal of Agricultural and Food Chemistry. 2005. Vol. 53. No. 25. pp. 9775-9780.
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Silverman F. P., Petracek P. D., Heiman D. F., Fledderman C. M., Warrior P. Salicylate Activity. 3. Structure Relationship to Systemic Acquired Resistance // Journal of Agricultural and Food Chemistry. 2005. Vol. 53. No. 25. pp. 9775-9780.
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TY - JOUR
DO - 10.1021/jf051383t
UR - https://doi.org/10.1021/jf051383t
TI - Salicylate Activity. 3. Structure Relationship to Systemic Acquired Resistance
T2 - Journal of Agricultural and Food Chemistry
AU - Silverman, F. Paul
AU - Petracek, Peter D.
AU - Heiman, Daniel F
AU - Fledderman, Christina M
AU - Warrior, Prem
PY - 2005
DA - 2005/11/15 00:00:00
PB - American Chemical Society (ACS)
SP - 9775-9780
IS - 25
VL - 53
SN - 0021-8561
SN - 1520-5118
ER -
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@article{2005_Silverman,
author = {F. Paul Silverman and Peter D. Petracek and Daniel F Heiman and Christina M Fledderman and Prem Warrior},
title = {Salicylate Activity. 3. Structure Relationship to Systemic Acquired Resistance},
journal = {Journal of Agricultural and Food Chemistry},
year = {2005},
volume = {53},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/jf051383t},
number = {25},
pages = {9775--9780},
doi = {10.1021/jf051383t}
}
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Silverman, F. Paul, et al. “Salicylate Activity. 3. Structure Relationship to Systemic Acquired Resistance.” Journal of Agricultural and Food Chemistry, vol. 53, no. 25, Nov. 2005, pp. 9775-9780. https://doi.org/10.1021/jf051383t.