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
A fungus (: fungi , , , or ; or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and molds, as well as the more familiar mushrooms. These organisms are classified as one of the tradit ...
species including ''
Cytospora populina'' and ''
Ceratocystis fimbriata
''Ceratocystis fimbriata'' is a fungus and a plant pathogen, attacking such diverse plants as the sweet potato (''black rot'') and the tapping panels of the Para rubber tree (''moldy rot''). It is a diverse species that attacks a wide variety of ...
''.
Properties
Scytalone is a chemical compound with a cyclic structure consisting of a
benzene
Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...
ring fused to a
cyclohexenone ring. It is a simple derivative of
1-tetralone with hydroxy groups at 3, 6 and 8th positions. It contains one
stereocenter
In stereochemistry, a stereocenter of a molecule is an atom (center), axis or plane that is the focus of stereoisomerism; that is, when having at least three different groups bound to the stereocenter, interchanging any two different groups cr ...
and therefore exists in R- and S- forms.
Biological significance
Scytalone is a natural product found in species of fungal genus ''
Scytalidium''. It is also found in many other fungal species like ''
Phialocephala lagerbergii
''Phialocephala'' is a genus of fungi in the family Mollisiaceae. It has a worldwide distribution.
It contains 39 accepted species and numerous undescribed taxa.
Species
This section contains only accepted species.
* '' Phialocephala amethyst ...
'',
''
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
''Pestalotiopsis'' is a genus of ascomycete fungi in the Sporocadaceae family.
Taxonomy
The genus was circumscribed by René Leopold Alix Ghislain Jules Steyaert in Bull. Jard. Bot. Etat. vol.19 on page 300 in 1949.
The genus name of ''Pestalo ...
''.
It is a pivotal intermediate in the biosynthesis of
melanin
Melanin (; ) is a family of biomolecules organized as oligomers or polymers, which among other functions provide the pigments of many organisms. Melanin pigments are produced in a specialized group of cells known as melanocytes.
There are ...
in fungi, the pigment responsible for fungal coloration. Melanin production in fungi is crucial for several biological processes like protection against
UV radiation
Ultraviolet radiation, also known as simply UV, is electromagnetic radiation of wavelengths of 10–400 nanometers, shorter than that of visible light, but longer than X-rays. UV radiation is present in sunlight and constitutes about 10% of t ...
, defense against
pathogens
In biology, a pathogen (, "suffering", "passion" and , "producer of"), in the oldest and broadest sense, is any organism or agent that can produce disease. A pathogen may also be referred to as an infectious agent, or simply a germ.
The term ...
, regulation of
cell wall
A cell wall is a structural layer that surrounds some Cell type, cell types, found immediately outside the cell membrane. It can be tough, flexible, and sometimes rigid. Primarily, it provides the cell with structural support, shape, protection, ...
integrity and protection against other physical and chemical stresses.
See also
*
Scytalone dehydratase
References
{{Reflist
Tetralones
Beta-hydroxy ketones
Bicyclic compounds
Cyclic ketones