# Scytalone

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**Scytalone** or **Scytolone** is a cyclic [beta hydroxy ketone](/source/Aldol) substituted by [hydroxy groups](/source/Hydroxy_group) at positions 3, 6, and 8. It is a natural product found in various [fungal](/source/Fungus) species including *[Cytospora populina](/source/Cytospora_populina)* and *[Ceratocystis fimbriata](/source/Ceratocystis_fimbriata)*.[1]

## Properties

Scytalone is a chemical compound with a cyclic structure consisting of a [benzene](/source/Benzene) ring fused to a [cyclohexenone](/source/Cyclohexenone) ring. It is a simple derivative of [1-tetralone](/source/1-tetralone) with hydroxy groups at 3, 6 and 8th positions.[2] It contains one [stereocenter](/source/Stereocenter)[3][4] and therefore exists in R- and S- forms.

## Biological significance

Scytalone is a natural product found in species of fungal genus *[Scytalidium](/source/Scytalidium)*.[5] It is also found in many other fungal species like *[Phialocephala lagerbergii](/source/Phialocephala_lagerbergii)*,[6] *[Cytospora populina](/source/Cytospora_populina)*,[7] *[Verticillium dahliae](/source/Verticillium_dahliae)*,[8] *[Phialophora lagerbergii](/source/Phialophora_lagerbergii)*[6] and *[Pestalotiopsis fici](/source/Pestalotiopsis_fici)*.[9]

It is a pivotal intermediate in the biosynthesis of [melanin](/source/Melanin) in fungi, the pigment responsible for fungal coloration.[10][11][12] Melanin production in fungi is crucial for several biological processes like protection against [UV radiation](/source/Ultraviolet), defense against [pathogens](/source/Pathogens), regulation of [cell wall](/source/Cell_wall) integrity and protection against other physical and chemical stresses.[13]

## See also

- [Scytalone dehydratase](/source/Scytalone_dehydratase)

## References

1. ["Scytalone"](https://lotus.naturalproducts.net/compound/lotus_id/LTS0050517). *lotus.naturalproducts.net*. Retrieved 2024-05-31.

1. Sankawa, Ushio; Shimada, Hisao; Sato, Toshitsugu; Kinoshita, Takeshi; Yamasaki, Kazuo (1977-01-01). ["Biosynthesis of scytalone"](https://www.sciencedirect.com/science/article/pii/S0040403901926723). *Tetrahedron Letters*. **18** (5): 483–486. [doi:10.1016/S0040-4039(01)92672-3](https://doi.org/10.1016/S0040-4039(01)92672-3). [ISSN 0040-4039](https://www.worldcat.org/issn/0040-4039)

1. ["49598-85-8 - ChemicalBook India"](https://www.chemicalbook.in/cas/49598-85-8.htm). *www.chemicalbook.in*. Retrieved 2024-05-31.

1. PubChem. ["(3r)-3,6,8-Trihydroxy-3,4-dihydronaphthalen-1(2h)-one"](https://pubchem.ncbi.nlm.nih.gov/compound/162567). *pubchem.ncbi.nlm.nih.gov*. Retrieved 2024-05-31.

1. Findlay, J. A. & Kwan, D. (1973-05-15). ["Scytalone (3,6,8-Trihydroxytetralone), a Metabolite from a Scytalidium Species"](http://www.nrcresearchpress.com/doi/10.1139/v73-242). *Canadian Journal of Chemistry*. **51** (10): 1617–1619. [doi:10.1139/v73-242](https://doi.org/10.1139/v73-242). [ISSN 0008-4042](https://www.worldcat.org/issn/0008-4042)

1. Bardshiri, Esfandiar & Simpson, Thomas J. (1983). ["13C AND 2H labelling studies on the biosynthesis of scytalone in phialaphora lagerbergII"](https://linkinghub.elsevier.com/retrieve/pii/S0040402001886646). *Tetrahedron*. **39** (21): 3539–3542. [doi:10.1016/S0040-4020(01)88664-6](https://doi.org/10.1016/S0040-4020(01)88664-6)

1. Jiao, Ying; Yoshihara, Teruhiko; Akimoto, Masanobu; Ichihara, Akitami (1994). ["Two Phenolic Compounds from Valsa ambiens"](https://academic.oup.com/bbb/article/58/4/784-785/5950724). *Bioscience, Biotechnology, and Biochemistry*. **58** (4): 784–785. [doi:10.1271/bbb.58.784](https://doi.org/10.1271/bbb.58.784). [ISSN 0916-8451](https://www.worldcat.org/issn/0916-8451)

1. 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"](http://link.springer.com/10.1007/BF00567299). *Chemistry of Natural Compounds*. **16** (3): 302–311. [Bibcode:1980CNatC..16..302S](https://ui.adsabs.harvard.edu/abs/1980CNatC..16..302S). [doi:10.1007/BF00567299](https://doi.org/10.1007/BF00567299). [ISSN 0009-3130](https://www.worldcat.org/issn/0009-3130)

1. 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"](https://onlinelibrary.wiley.com/doi/10.1111/mmi.13711). *Molecular Microbiology*. **105** (3): 469–483. [doi:10.1111/mmi.13711](https://doi.org/10.1111/mmi.13711). [ISSN 0950-382X](https://www.worldcat.org/issn/0950-382X). [PMID 28517364](https://pubmed.ncbi.nlm.nih.gov/28517364)

1. 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"](http://www.nrcresearchpress.com/doi/10.1139/m76-115). *Canadian Journal of Microbiology*. **22** (6): 787–799. [doi:10.1139/m76-115](https://doi.org/10.1139/m76-115). [ISSN 0008-4166](https://www.worldcat.org/issn/0008-4166). [PMID 945120](https://pubmed.ncbi.nlm.nih.gov/945120)

1. Bell, A. A.; Stipanovic, R. D.; Puhalla, J. E. (1976-01-01). ["Pentaketide metabolites of verticillium dahliae"](https://dx.doi.org/10.1016/0040-4020%2876%2985009-0). *Tetrahedron*. **32** (12): 1353–1356. [doi:10.1016/0040-4020(76)85009-0](https://doi.org/10.1016/0040-4020(76)85009-0). [ISSN 0040-4020](https://www.worldcat.org/issn/0040-4020)

1. Kubo, Yasuyuki; Suzuki, Kazumi; Furusawa, Iwao; Yamamoto, Masaki (1983-09-01). ["Scytalone as a natural intermediate of melanin biosynthesis in appressoria ofColletotrichum lagenarium"](https://dx.doi.org/10.1016/0147-5975%2883%2990041-5). *Experimental Mycology*. **7** (3): 208–215. [doi:10.1016/0147-5975(83)90041-5](https://doi.org/10.1016/0147-5975(83)90041-5). [ISSN 0147-5975](https://www.worldcat.org/issn/0147-5975)

1. Cordero, Radames JB & Casadevall, Arturo (2017). "Functions of fungal melanin beyond virulence". *Fungal Biology Reviews*. **31** (2): 99–112. [Bibcode:2017FunBR..31...99C](https://ui.adsabs.harvard.edu/abs/2017FunBR..31...99C). [doi:10.1016/j.fbr.2016.12.003](https://doi.org/10.1016/j.fbr.2016.12.003). [ISSN 1749-4613](https://www.worldcat.org/issn/1749-4613). [PMC 6812541](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6812541). [PMID 31649746](https://pubmed.ncbi.nlm.nih.gov/31649746)

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