Bleaching activity of 4-Phenyl-3-(substituted benzylthio)-4H-1,2,4-triazoles

Naotaka Yamada, Daisuke Kusano, Eiich Kuwano

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

A variety of 4-aryl- and 4-alkyl-3-(substituted benzylthio)-4H-1,2,4-triazoles were prepared and evaluated for their bleaching activity by the lettuce seedling test. Among the series of tested compounds, 4-(3-fluorophenyl)-3-(4-trifluoromethylbenzylthio)-4H-1,2,4-triazole (39) exhibited the highest bleaching activity, causing complete bleaching symptoms at 10 μM. In the dark condition, compound 39 inhibited the formation of such carotenoids as β-carotene, violaxanthin, neoxanthin and lutein, resulting in the formation of ζ-carotene, phytoene, phytofluene and β-zeacarotene, which were not detected in the untreated control. Treatment by compound 39 at 50 μM resulted in the amount of accumulated ζ-carotene being seven-fold higher than that of phytoene, phytofluene and β-zeacarotene. These results suggest that compound 39 might have interfered with desaturation, especially ζ-carotene desaturation, during carotenoid biosynthesis.

Original languageEnglish
Pages (from-to)1671-1676
Number of pages6
JournalBioscience, Biotechnology and Biochemistry
Volume66
Issue number8
DOIs
Publication statusPublished - Jan 1 2002

Fingerprint

Carotenoids
Bleaching
Lutein
Lettuce
Seedlings
Biosynthesis
1,2,4-triazole
phytofluene
phytoene
zeacarotene

All Science Journal Classification (ASJC) codes

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry

Cite this

Bleaching activity of 4-Phenyl-3-(substituted benzylthio)-4H-1,2,4-triazoles. / Yamada, Naotaka; Kusano, Daisuke; Kuwano, Eiich.

In: Bioscience, Biotechnology and Biochemistry, Vol. 66, No. 8, 01.01.2002, p. 1671-1676.

Research output: Contribution to journalArticle

@article{85a6d6a84dc143a9908644c30d76ee73,
title = "Bleaching activity of 4-Phenyl-3-(substituted benzylthio)-4H-1,2,4-triazoles",
abstract = "A variety of 4-aryl- and 4-alkyl-3-(substituted benzylthio)-4H-1,2,4-triazoles were prepared and evaluated for their bleaching activity by the lettuce seedling test. Among the series of tested compounds, 4-(3-fluorophenyl)-3-(4-trifluoromethylbenzylthio)-4H-1,2,4-triazole (39) exhibited the highest bleaching activity, causing complete bleaching symptoms at 10 μM. In the dark condition, compound 39 inhibited the formation of such carotenoids as β-carotene, violaxanthin, neoxanthin and lutein, resulting in the formation of ζ-carotene, phytoene, phytofluene and β-zeacarotene, which were not detected in the untreated control. Treatment by compound 39 at 50 μM resulted in the amount of accumulated ζ-carotene being seven-fold higher than that of phytoene, phytofluene and β-zeacarotene. These results suggest that compound 39 might have interfered with desaturation, especially ζ-carotene desaturation, during carotenoid biosynthesis.",
author = "Naotaka Yamada and Daisuke Kusano and Eiich Kuwano",
year = "2002",
month = "1",
day = "1",
doi = "10.1271/bbb.66.1671",
language = "English",
volume = "66",
pages = "1671--1676",
journal = "Bioscience, Biotechnology and Biochemistry",
issn = "0916-8451",
publisher = "Japan Society for Bioscience Biotechnology and Agrochemistry",
number = "8",

}

TY - JOUR

T1 - Bleaching activity of 4-Phenyl-3-(substituted benzylthio)-4H-1,2,4-triazoles

AU - Yamada, Naotaka

AU - Kusano, Daisuke

AU - Kuwano, Eiich

PY - 2002/1/1

Y1 - 2002/1/1

N2 - A variety of 4-aryl- and 4-alkyl-3-(substituted benzylthio)-4H-1,2,4-triazoles were prepared and evaluated for their bleaching activity by the lettuce seedling test. Among the series of tested compounds, 4-(3-fluorophenyl)-3-(4-trifluoromethylbenzylthio)-4H-1,2,4-triazole (39) exhibited the highest bleaching activity, causing complete bleaching symptoms at 10 μM. In the dark condition, compound 39 inhibited the formation of such carotenoids as β-carotene, violaxanthin, neoxanthin and lutein, resulting in the formation of ζ-carotene, phytoene, phytofluene and β-zeacarotene, which were not detected in the untreated control. Treatment by compound 39 at 50 μM resulted in the amount of accumulated ζ-carotene being seven-fold higher than that of phytoene, phytofluene and β-zeacarotene. These results suggest that compound 39 might have interfered with desaturation, especially ζ-carotene desaturation, during carotenoid biosynthesis.

AB - A variety of 4-aryl- and 4-alkyl-3-(substituted benzylthio)-4H-1,2,4-triazoles were prepared and evaluated for their bleaching activity by the lettuce seedling test. Among the series of tested compounds, 4-(3-fluorophenyl)-3-(4-trifluoromethylbenzylthio)-4H-1,2,4-triazole (39) exhibited the highest bleaching activity, causing complete bleaching symptoms at 10 μM. In the dark condition, compound 39 inhibited the formation of such carotenoids as β-carotene, violaxanthin, neoxanthin and lutein, resulting in the formation of ζ-carotene, phytoene, phytofluene and β-zeacarotene, which were not detected in the untreated control. Treatment by compound 39 at 50 μM resulted in the amount of accumulated ζ-carotene being seven-fold higher than that of phytoene, phytofluene and β-zeacarotene. These results suggest that compound 39 might have interfered with desaturation, especially ζ-carotene desaturation, during carotenoid biosynthesis.

UR - http://www.scopus.com/inward/record.url?scp=0036689878&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0036689878&partnerID=8YFLogxK

U2 - 10.1271/bbb.66.1671

DO - 10.1271/bbb.66.1671

M3 - Article

VL - 66

SP - 1671

EP - 1676

JO - Bioscience, Biotechnology and Biochemistry

JF - Bioscience, Biotechnology and Biochemistry

SN - 0916-8451

IS - 8

ER -