Scytalone Explained

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.[1]

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.[2] It contains one 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.[5] It is also found in many other fungal species like Phialocephala lagerbergii,[6] Cytospora populina,[7] Verticillium dahliae,[8] Phialophora lagerbergii and Pestalotiopsis fici.[9]

It is a pivotal intermediate in the biosynthesis of 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, defense against pathogens, regulation of cell wall integrity and protection against other physical and chemical stresses.[13]

See also

Notes and References

  1. Web site: Scytalone . 2024-05-31 . lotus.naturalproducts.net.
  2. Sankawa . Ushio . Shimada . Hisao . Sato . Toshitsugu . Kinoshita . Takeshi . Yamasaki . Kazuo . 1977-01-01 . Biosynthesis of scytalone . Tetrahedron Letters . 18 . 5 . 483–486 . 10.1016/S0040-4039(01)92672-3 . 0040-4039.
  3. Web site: 49598-85-8 - ChemicalBook India . 2024-05-31 . www.chemicalbook.in.
  4. Web site: PubChem . (3r)-3,6,8-Trihydroxy-3,4-dihydronaphthalen-1(2h)-one . 2024-05-31 . pubchem.ncbi.nlm.nih.gov . en.
  5. Findlay . J. A. . Kwan . D. . 1973-05-15 . Scytalone (3,6,8-Trihydroxytetralone), a Metabolite from a Scytalidium Species . Canadian Journal of Chemistry . en . 51 . 10 . 1617–1619 . 10.1139/v73-242 . 0008-4042.
  6. Bardshiri . Esfandiar . Simpson . Thomas J. . 1983 . 13C AND 2H labelling studies on the biosynthesis of scytalone in phialaphora lagerbergII . Tetrahedron . en . 39 . 21 . 3539–3542 . 10.1016/S0040-4020(01)88664-6.
  7. Jiao . Ying . Yoshihara . Teruhiko . Akimoto . Masanobu . Ichihara . Akitami . 1994 . Two Phenolic Compounds from Valsa ambiens . Bioscience, Biotechnology, and Biochemistry . en . 58 . 4 . 784–785 . 10.1271/bbb.58.784 . 0916-8451.
  8. 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 . en . 16 . 3 . 302–311 . 10.1007/BF00567299 . 0009-3130.
  9. 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 . en . 105 . 3 . 469–483 . 10.1111/mmi.13711 . 28517364 . 0950-382X.
  10. 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 . en . 22 . 6 . 787–799 . 10.1139/m76-115 . 945120 . 0008-4166.
  11. Bell . A. A. . Stipanovic . R. D. . Puhalla . J. E. . 1976-01-01 . Pentaketide metabolites of verticillium dahliae . Tetrahedron . 32 . 12 . 1353–1356 . 10.1016/0040-4020(76)85009-0 . 0040-4020.
  12. 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 . 10.1016/0147-5975(83)90041-5 . 0147-5975.
  13. Cordero . Radames JB . Casadevall . Arturo . 2017 . Functions of fungal melanin beyond virulence . Fungal Biology Reviews . 31 . 2 . 99–112 . 10.1016/j.fbr.2016.12.003 . 1749-4613 . 6812541 . 31649746. 2017FunBR..31...99C .

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