Hispidin

Hispidin
Chemical structure of hispidin
Chemical structure of hispidin
Names
Preferred IUPAC name
6-[(1E)-2-(3,4-Dihydroxyphenyl)ethen-1-yl]-4-hydroxy-2H-pyran-2-one
Other names
6-(3,4-Dihydroxystyryl)-4-hydroxy-2-pyrone
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C13H10O5/c14-9-6-10(18-13(17)7-9)3-1-8-2-4-11(15)12(16)5-8/h1-7,14-16H/b3-1+ X markN
    Key: SGJNQVTUYXCBKH-HNQUOIGGSA-N X markN
  • C1=CC(=C(C=C1/C=C/C2=CC(=CC(=O)O2)O)O)O
  • OC=2/C=C(/C=C/c1ccc(O)c(O)c1)OC(=O)C=2
Properties
C13H10O5
Molar mass 246.218 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Hispidin is a natural substance. It can also be synthesized.

Hispidin 4-O-β-D-glucopyranoside can be found in Pteris ensiformis whereas hispidin derivatives, such as phellibaumins, can be found in the edible mushroom Inonotus xeranticus or Phellinus. Hispidin is a precursor of fungal luciferin, a compound responsible for light emission by luminous mushrooms.

See also

References

  1. ↑ Gonindard, C.; Bergonz i, C.; Denier, C.; Sergheraert, C.; Klaebe, A.; Chavant, L.; Hollande, E. (1997). "Synthetic hispidin, a PKC inhibitor, is more cytotoxic toward cancer cells than normal cells in vitro". Cell Biology and Toxicology. 13 (3): 141–53. doi:10.1023/A:1007321227010. PMID 9088624. S2CID 755744.
  2. ↑ Chen, Y.; Chang, F.; Lin, Y.; Wang, L.; Chen, J.; Wu, Y.; Wu, M. (2007). "Identification of phenolic antioxidants from Sword Brake fern (Pteris ensiformis Burm.)". Food Chemistry. 105: 48–56. doi:10.1016/j.foodchem.2007.03.055.
  3. ↑ Lee, In-Kyoung; Seok, Soon-Ja; Kim, Wan-Kyu; Yun, Bong-Sik (2006). "Hispidin Derivatives from the Mushroom Inonotusxeranticusand Their Antioxidant Activity". Journal of Natural Products. 69 (2): 299–301. doi:10.1021/np050453n. PMID 16499338.
  4. ↑ Lee, In-Kyoung; Yun, Bong-Sik (2007). "Highly oxygenated and unsaturated metabolites providing a diversity of hispidin class antioxidants in the medicinal mushrooms Inonotus and Phellinus". Bioorganic & Medicinal Chemistry. 15 (10): 3309–14. doi:10.1016/j.bmc.2007.03.039. PMID 17387019.
  5. ↑ Lee, Yeon Sil; Kang, Young-Hee; Jung, Ju-Young; Lee, Sanghyun; Ohuchi, Kazuo; Shin, Kuk Hyun; Kang, Il-Jun; Park, Jung Han Yoon; et al. (October 2008). "Protein glycation inhibitors from the fruiting body of Phellinus linteus". Biological & Pharmaceutical Bulletin. 31 (10): 1968–72. doi:10.1248/bpb.31.1968. PMID 18827365.