Scytalone or Scytolone is a cyclic
beta hydroxy ketone substituted by
hydroxy group
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...
s at positions 3, 6, and 8. It is a natural product found in various
fungal species including ''
Cytospora populina'' and ''
Ceratocystis fimbriata''.
Properties
Scytalone is a chemical compound with a cyclic structure consisting of a
benzene ring fused to a
cyclohexenone
Cyclohexenone is an organic compound which is a versatile intermediate used in the synthesis of a variety of chemical products such as pharmaceuticals and fragrances. It is colorless liquid, but commercial samples are often yellow.
Industrially, ...
ring. It is a simple derivative of
1-tetralone
1-Tetralone is a bicyclic aromatic hydrocarbon and a ketone. In terms of its structure, it can also be regarded as benzo-fused cyclohexanone. It is a colorless oil with a faint odor. It is used as starting material for agricultural and pharmace ...
with hydroxy groups at 3, 6 and 8th positions. It contains one
stereocenter and therefore exists in R- and S- forms.
Biological significance
Scytalone is a natural product found in species of fungal genus ''
Scytalidium
''Scytalidium'' is a genus of fungi in the Helotiales order. The relationship of this taxon to other taxa within the order is unknown (''incertae sedis''), and it has not yet been placed with certainty into any family. This genus of anamorphic ...
''. It is also found in many other fungal species like ''
Phialocephala lagerbergii'',
''
Cytospora populina'', ''
Verticillium dahliae
''Verticillium dahliae'' is a fungal plant pathogen. It causes verticillium wilt in many plant species, causing leaves to curl and discolor. It may cause death in some plants. Over 400 plant species are affected by ''Verticillium'' complex.
M ...
'', ''
Phialophora lagerbergii''
and ''
Pestalotiopsis fici''.
It is a pivotal intermediate in the biosynthesis of
melanin in fungi, the pigment responsible for fungal coloration. Melanin production in fungi is crucial for several biological processes like protection against
UV radiation, defense against
pathogens, regulation of
cell wall
A cell wall is a structural layer surrounding some types of cells, just outside the cell membrane. It can be tough, flexible, and sometimes rigid. It provides the cell with both structural support and protection, and also acts as a filtering mech ...
integrity and protection against other physical and chemical stresses.
See also
*
Scytalone dehydratase
The enzyme scytalone dehydratase () catalyzes the chemical reaction
: scytalone \rightleftharpoons 1,3,8-trihydroxynaphthalene + H2O
This enzyme belongs to the family of lyase
In biochemistry, a lyase is an enzyme that catalyzes the breaking ...
References
{{Reflist
Tetralones
Beta-hydroxy ketones
Bicyclic compounds
Cyclic ketones