Isothiocyanate
Isothiocyanate is the
chemical group -
N=
C=
S, formed by substituting
sulfur for
oxygen in the
isocyanate group.
Allyl isothiocyanate is also called mustard oil.
Encyclopedia
Isothiocyanate is the
chemical group
-N=
C=
S, formed by substituting
sulfur for
oxygen in the
isocyanate group.
Allyl isothiocyanate is also called mustard oil.
Reactions
Isothiocyanates generally act as an electrophiles with the carbon atom as the electrophilic center.
How they are found in nature
Isothiocyanates are largely found locked in the form of
glucosinolates and are found largely in
cruciferous vegetables such as
brocolli and
Brussels sprouts, as well as in
wasabi and
watercress. Such plants contain an enzyme termed
myrosinase which can induce a rearrangement of the glucosinolates leading to the generation of the free isothiocyanate.
Biological Activity
Isothiocyanates, such as phenethyl isothiocyanate and sulforaphane, have been shown to inhibit carcinogenesis and tumorigensis and as such are useful chemopreventive agents against the development and proliferation of cancers. They work on a variety of levels. Most notably, they have been shown to inhibit carcinogenesis through inhibition of cytochrome P450 enzymes, which oxidise compounds such as benzo[a]pyrene and other polycyclic aromatic hydrocarbons into more polar epoxy-diols which can then cause mutation and induce cancer development. Phenethyl isothiocyanate has been shown to induce apoptosis in certain cancer cell lines, and in some cases, is even able to induce apoptosis in cells that are resistant to some currently used chemotherapeutic drugs. For example, in drug resistant leukemia cells which produce the powerful apoptosis inhibitor protein BCl-2.
See also
References
- Improved approaches in the synthesis of new 2-acetophenones M. Carmen Ortega-Alfaro, José G. López-Cortés, Hiram Rangel Sánchez, Rubén A. Toscano, Guillermo Penieres Carrillo, and Cecilio Álvarez-Toledano Arkivoc pp 356-365 2005
