Hispidin

Hispidin
Names
	IUPAC name 2-[(E)-2-(3,4-dDihydroxyphenyl)ethenyl]-6-hydroxypyran-4-one
	Other names 6-(3,4-Dihydroxystyryl)-4-hydroxy-2-pyrone
Identifiers
CAS Number	555-55-5 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	13975015 ;
PubChem CID	5353671;
UNII	SSJ18CG55E ;
	InChI 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+ Key: SGJNQVTUYXCBKH-HNQUOIGGSA-N ; InChI=1/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+ Key: SGJNQVTUYXCBKH-HNQUOIGGBX;
	SMILES C1=CC(=C(C=C1C=CC2=CC(=O)C=C(O2)O)O)O; OC=2/C=C(/C=C/c1ccc(O)c(O)c1)OC(=O)C=2;
Properties
Chemical formula	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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	Infobox references

Hispidin is a natural substance. It can also be synthesized.[1]

Hispidin 4-O-β-D-glucopyranoside can be found in Pteris ensiformis[2] whereas hispidin derivatives, such as phellibaumins, can be found in the edible mushroom Inonotus xeranticus[3] or Phellinus.[4][5] Hispidin is a precursor of fungal luciferin, a compound responsible for light emission by luminous mushrooms.

References

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.
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.
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.
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.
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.

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[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.

[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.

[pmid18827365-5] 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.

Hispidin

See also

References