From Wikipedia, the free encyclopedia
Chemical compound
Scytalone
Names
IUPAC name
(3R)-3,6,8-trihydroxy-3,4-dihydro-2H-naphthalen-1-one
Other names
3,4-Dihydro-3,6,8-trihydroxy-1(2H)naphthalenone SCYTALON Scytolone
Identifiers
ChEBI
ChEMBL
ChemSpider
KEGG
MeSH
scytalone
UNII
InChI=1S/C10H10O4/c11-6-1-5-2-7(12)4-9(14)10(5)8(13)3-6/h1,3,7,11-13H,2,4H2/t7-/m1/s1
Key: RTWVXIIKUFSDJB-SSDOTTSWSA-N
C1[C@H](CC(=O)C2=C1C=C(C=C2O)O)O
Properties
C 10 H 10 O 4
Molar mass
194.18 g/mol
log P
0.9
[1]
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Scytalone or Scytolone is a cyclic
beta hydroxy ketone substituted by
hydroxy groups at positions 3, 6, and 8. It is a natural product found in various
fungal species including
Cytospora populina and
Ceratocystis fimbriata .
[2]
Scytalone is a chemical compound with a cyclic structure consisting of a
benzene ring fused to a
cyclohexenone ring. It is a simple derivative of
1-tetralone with hydroxy groups at 3, 6 and 8th positions.
[3] It contains one
stereocenter
[4]
[5] and therefore exists in R- and S- forms.
Scytalone is a natural product found in species of fungal genus
Scytalidium .
[6] It is also found in many other fungal species like
Phialocephala lagerbergii ,
[7]
Cytospora populina ,
[8]
Verticillium dahliae ,
[9]
Phialophora lagerbergii
[7] and
Pestalotiopsis fici .
[10]
It is a pivotal intermediate in the biosynthesis of
melanin in fungi, the pigment responsible for fungal coloration.
[11]
[12]
[13] Melanin production in fungi is crucial for several biological processes like protection against
UV radiation , defense against
pathogens , regulation of
cell wall integrity and protection against other physical and chemical stresses.
[14]
^ Computed by XLogP3 3.0 (PubChem release 2021-10-14)
^
"Scytalone" . lotus.naturalproducts.net . Retrieved 2024-05-31 .
^ Sankawa, Ushio; Shimada, Hisao; Sato, Toshitsugu; Kinoshita, Takeshi; Yamasaki, Kazuo (1977-01-01).
"Biosynthesis of scytalone" . Tetrahedron Letters . 18 (5): 483–486.
doi :
10.1016/S0040-4039(01)92672-3 .
ISSN
0040-4039 .
^
"49598-85-8 - ChemicalBook India" . www.chemicalbook.in . Retrieved 2024-05-31 .
^ PubChem.
"(3r)-3,6,8-Trihydroxy-3,4-dihydronaphthalen-1(2h)-one" . pubchem.ncbi.nlm.nih.gov . Retrieved 2024-05-31 .
^ Findlay, J. A.; Kwan, D. (1973-05-15).
"Scytalone (3,6,8-Trihydroxytetralone), a Metabolite from a Scytalidium Species" . Canadian Journal of Chemistry . 51 (10): 1617–1619.
doi :
10.1139/v73-242 .
ISSN
0008-4042 .
^
a
b Bardshiri, Esfandiar; Simpson, Thomas J. (1983).
"13C AND 2H labelling studies on the biosynthesis of scytalone in phialaphora lagerbergII" . Tetrahedron . 39 (21): 3539–3542.
doi :
10.1016/S0040-4020(01)88664-6 .
^ Jiao, Ying; Yoshihara, Teruhiko; Akimoto, Masanobu; Ichihara, Akitami (1994).
"Two Phenolic Compounds from Valsa ambiens" . Bioscience, Biotechnology, and Biochemistry . 58 (4): 784–785.
doi :
10.1271/bbb.58.784 .
ISSN
0916-8451 .
^ Stepanichenko, N. N.; Ten, L. N.; Tyshchenko, A. A.; Avazkhodzhaev, M. Kh.; Mukhamedzhanov, S. Z.; Otroshchenko, O. S. (1980).
"Metabolites of the pathogenic fungusVerticillium dahliae. X. Induction of phytoalexins in the cotton plant by metabolites in the pathogen" . Chemistry of Natural Compounds . 16 (3): 302–311.
doi :
10.1007/BF00567299 .
ISSN
0009-3130 .
^ Zhang, Peng; Wang, Xiuna; Fan, Aili; Zheng, Yanjing; Liu, Xingzhong; Wang, Shihua; Zou, Huixi; Oakley, Berl R.; Keller, Nancy P.; Yin, Wen-Bing (2017).
"A cryptic pigment biosynthetic pathway uncovered by heterologous expression is essential for conidial development in Pestalotiopsis fici" . Molecular Microbiology . 105 (3): 469–483.
doi :
10.1111/mmi.13711 .
ISSN
0950-382X .
PMID
28517364 .
^ Bell, A. A.; Puhalla, J. E.; Tolmsoff, W. J.; Stipanovic, R. D. (1976-06-01).
"Use of mutants to establish (+)-scytalone as an intermediate in melanin biosynthesis by Verticillium dahliae" . Canadian Journal of Microbiology . 22 (6): 787–799.
doi :
10.1139/m76-115 .
ISSN
0008-4166 .
PMID
945120 .
^ Bell, A. A.; Stipanovic, R. D.; Puhalla, J. E. (1976-01-01).
"Pentaketide metabolites of verticillium dahliae" . Tetrahedron . 32 (12): 1353–1356.
doi :
10.1016/0040-4020(76)85009-0 .
ISSN
0040-4020 .
^ Kubo, Yasuyuki; Suzuki, Kazumi; Furusawa, Iwao; Yamamoto, Masaki (1983-09-01).
"Scytalone as a natural intermediate of melanin biosynthesis in appressoria ofColletotrichum lagenarium" . Experimental Mycology . 7 (3): 208–215.
doi :
10.1016/0147-5975(83)90041-5 .
ISSN
0147-5975 .
^ Cordero, Radames JB; Casadevall, Arturo (2017).
"Functions of fungal melanin beyond virulence" . Fungal Biology Reviews . 31 (2): 99–112.
Bibcode :
2017FunBR..31...99C .
doi :
10.1016/j.fbr.2016.12.003 .
ISSN
1749-4613 .
PMC
6812541 .
PMID
31649746 .