Variegatinska kislina

Variegatinska kislina
Imena
	IUPAC ime α-[4-(3,4-dihidroksifenil)-3-hidroksi-5-oksofuran-2(5H)-iliden]-3,4-dihidroksibenzenocetna kislina
	Druga imena 3,3',4,4'-tetrahidroksi pulvinska kislina
Identifikatorji
Številka CAS	20988-30-1;
3D model (JSmol)	Interaktivna slika;
	InChI InChI=1S/C18H12O9/c19-9-3-1-7(5-11(9)21)13-15(23)16(27-18(13)26)14(17(24)25)8-2-4-10(20)12(22)6-8/h1-6,19-23H,(H,24,25)/b16-14+ Key: MRRYHTCWZKZVIH-JQIJEIRASA-N;
	SMILES O=C(C(C1=CC(O)=C(O)C=C1)=C/2O)OC2=C(C(O)=O)/C3=CC(O)=C(O)C=C3;
Lastnosti
Kemijska formula	C18H12O9
Molska masa	372,29 g·mol−1
	Če ni navedeno drugače, podatki veljajo za material v standardnem stanju pri 25 °C, 100 kPa).
	Sklici infopolja

Variegatinska kislina (3,3',4,4'-tetrahidroksipulvinska kislina) je oranžen pigment, ki pa na zraku pomodri (znano je, da meso številnih gobanov ob dotiku na poškodovanem mestu pomodrijo oz. potemnijo). Zaradi delovanja oksidativnih encimov se namreč pretvori v modro obarvane chinonmethidne anione.^[1]

Prvič je bila osamljena iz Suillus variegatus.^[2] Je močan antioksidant.^[3]^[4] Nespecifično inhibira citokrom P450.^[5] Leta 2001 so jo kemijsko sintetizirali s Suzukijevo reakcijo.^[6]

Glej tudi[uredi | uredi kodo]

Sklici[uredi | uredi kodo]

↑ Velíšek J; Cejpek K. (2011). »Pigments of higher fungi: A review« (PDF). Czech Journal of Food Science. 29 (2): 87–102.
↑ Edwards RL; Elsworthy GC. (1967). »Variegatic acid, a new tetronic acid responsible for the blueing reaction in the fungus Suillus (Boletus) variegatus (Swartz ex Fr.)«. Chemical Communications (London) (8): 373b–374. doi:10.1039/C1967000373B.
↑ Kasuga A; Aoyagi Y; Sugahara T. (1995). »Antioxidant activity of fungus Suillus bovinus (L: Fr.) O. Kuntze«. Journal of Food Science. 60 (5): 1113–85. doi:10.1111/j.1365-2621.1995.tb06304.x.
↑ Vidovic SS; Mujic IO; Zekovic ZP; Lepojevic ZD; Tumbas VT; Mujic AI (2010). »Antioxidant properties of selected Boletus mushrooms«. Food Biophysics. 5 (1): 49–58. doi:10.1007/s11483-009-9143-6.
↑ Huang YT; Onose J; Abe N; Yoshikawa K. (2009). »In vitro inhibitory effects of pulvinic acid derivatives isolated from Chinese edible mushrooms, Boletus calopus and Suillus bovinus, on cytochrome P450 activity«. Bioscience, Biotechnology, and Biochemistry. 73 (4): 855–60. doi:10.1271/bbb.80759. PMID 19352038.
↑ Ahmed Z; Langer P. (2005). »Synthesis of natural pulvinic acids based on a '[3+2] cyclization-Suzuki cross-coupling' strategy«. Tetrahedron. 61 (8): 2055–63. doi:10.1016/j.tet.2004.12.048.

[Velíšek_2011-1] Velíšek J; Cejpek K. (2011). »Pigments of higher fungi: A review« (PDF). Czech Journal of Food Science. 29 (2): 87–102.

[Edwards_1967-2] Edwards RL; Elsworthy GC. (1967). »Variegatic acid, a new tetronic acid responsible for the blueing reaction in the fungus Suillus (Boletus) variegatus (Swartz ex Fr.)«. Chemical Communications (London) (8): 373b–374. doi:10.1039/C1967000373B.

[Kasuga_1995-3] Kasuga A; Aoyagi Y; Sugahara T. (1995). »Antioxidant activity of fungus Suillus bovinus (L: Fr.) O. Kuntze«. Journal of Food Science. 60 (5): 1113–85. doi:10.1111/j.1365-2621.1995.tb06304.x.

[Vidovic_2010-4] Vidovic SS; Mujic IO; Zekovic ZP; Lepojevic ZD; Tumbas VT; Mujic AI (2010). »Antioxidant properties of selected Boletus mushrooms«. Food Biophysics. 5 (1): 49–58. doi:10.1007/s11483-009-9143-6.

[Huang_2009-5] Huang YT; Onose J; Abe N; Yoshikawa K. (2009). »In vitro inhibitory effects of pulvinic acid derivatives isolated from Chinese edible mushrooms, Boletus calopus and Suillus bovinus, on cytochrome P450 activity«. Bioscience, Biotechnology, and Biochemistry. 73 (4): 855–60. doi:10.1271/bbb.80759. PMID 19352038.

[Ahmed_2005-6] Ahmed Z; Langer P. (2005). »Synthesis of natural pulvinic acids based on a '[3+2] cyclization-Suzuki cross-coupling' strategy«. Tetrahedron. 61 (8): 2055–63. doi:10.1016/j.tet.2004.12.048.

[1]

[2]

[3]

[4]

[5]

[6]