Scytalone

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
CAS Number	49598-85-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16945 ;
ChEMBL	ChEMBL4081370;
ChemSpider	142729;
KEGG	C00779;
MeSH	scytalone
PubChem CID	162567;
UNII	1MQ5L1414D;
CompTox Dashboard (EPA)	DTXSID50964289 ;
	InChI 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;
	SMILES C1[C@H](CC(=O)C2=C1C=C(C=C2O)O)O;
Properties
Chemical formula	C10H10O4
Molar mass	194.18 g/mol
log P	0.9
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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]

Properties

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.

Biological significance

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]

References

^ 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. Bibcode:1980CNatC..16..302S. 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.

[1] Computed by XLogP3 3.0 (PubChem release 2021-10-14)

[2] "Scytalone". lotus.naturalproducts.net. Retrieved 2024-05-31.

[3] 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.

[4] "49598-85-8 - ChemicalBook India". www.chemicalbook.in. Retrieved 2024-05-31.

[5] PubChem. "(3r)-3,6,8-Trihydroxy-3,4-dihydronaphthalen-1(2h)-one". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-05-31.

[6] 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.

[:0-7] 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.

[8] 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.

[9] 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. Bibcode:1980CNatC..16..302S. doi:10.1007/BF00567299. ISSN 0009-3130.

[10] 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.

[11] 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.

[12] 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.

[13] 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.

[14] 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.

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Properties

Biological significance

See also

References