Derivatization of isothiocyanates and their reactive adducts for chromatographic analysis

Phytochemistry
Niels AgerbirkRenato Iori

Abstract

Isothiocyanates form adducts with a multitude of biomolecules, and these adducts need analytical methods. Likewise, analytical methods for hydrophilic isothiocyanates are needed. We considered reaction with ammonia to form thiourea derivatives. The hydrophilic, glycosylated isothiocyanate moringin, 4-(α-L-rhamnopyranosyloxy)benzyl isothiocyanate, was efficiently derivatized to the thiourea derivative by incubation with ammonia. The hydrophobic benzyl isothiocyanate was also efficiently derivatized to the thiourea derivative. The thiourea group provided a UV absorbing chromophore, and the derivatives showed expectable sodium and hydrogen adducts in ion trap mass spectrometry and were suitable for liquid chromatography analysis. Reactive dithiocarbamate adducts constitute the major type of reactive ITC adduct expected in biological matrices. Incubation of a model dithiocarbamate with ammonia likewise resulted in conversion to the corresponding thiourea derivative, suggesting that a variety of matrix-bound reactive isothiocyanate adducts can be determined using this strategy. As an example of the application of the method, recovery of moringin and benzyl isothiocyanate applied to cabbage leaf discs was studied in simulated insect ...Continue Reading

References

Nov 1, 1967·Journal of the Science of Food and Agriculture·L A Appelqvist, E Josefsson
May 27, 2004·Natural Product Reports·Birgit Holst, Gary Williamson
Sep 24, 2005·Pharmaceutical Research·Yan JiMarilyn E Morris
Mar 19, 2008·The Plant Journal : for Cell and Molecular Biology·Jae Hak KimGeorg Jander
Mar 26, 2010·Journal of Agricultural and Food Chemistry·Niels AgerbirkMarian Ørgaard
Feb 15, 2011·Phytochemistry·Inis Winde, Ute Wittstock
Jun 28, 2011·Biochimica Et Biophysica Acta·Kristin K Brown, Mark B Hampton
Dec 24, 2011·Insect Biochemistry and Molecular Biology·Katharina SchrammUte Wittstock
Mar 13, 2012·Phytochemistry·Niels Agerbirk, Carl Erik Olsen
Feb 19, 2015·Journal of Agricultural and Food Chemistry·Nadja FörsterInga Mewis

❮ Previous
Next ❯

Citations

Oct 21, 2015·Insect Biochemistry and Molecular Biology·Stefan PentzoldSøren Bak
Aug 23, 2020·Nutrients·Alicia Arredondo EveZeynep Madak-Erdogan
Apr 1, 2021·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·Giulia Di Dalmazi, Cesidio Giuliani
Apr 7, 2021·Zeitschrift Für Naturforschung. C, a Journal of Biosciences·Merve Bademİhsan Calıs

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.