| 词条 | Variegatic acid |
| 释义 |
| ImageFile =Variegatic acid.svg | ImageSize = 200px | ImageAlt = | ImageFile1 = | ImageSize1 = 300 | ImageAlt1 = Space-filling model | Name=Variegatic acid | IUPACName=α-[4-(3,4-Dihydroxyphenyl)-3-hydroxy-5-oxofuran-2(5H)-ylidene]-3,4-dihydroxybenzeneacetic acid | OtherNames=3,3',4,4'-tetrahydroxy pulvinic acid |Section1={{Chembox Identifiers | ChemSpiderID = | 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+ | InChIKey =MRRYHTCWZKZVIH-JQIJEIRASA-N | CASNo= 20988-30-1 | PubChem= | 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 }} |Section2={{Chembox Properties | C=18 | H=12 | O=9 | MolarMass= | Appearance= | Density= | MeltingPt= | BoilingPt= | Solubility= |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = }} Variegatic acid (3,3',4,4'-tetrahydroxypulvinic acid) is an orange pigment found in some mushrooms. It is responsible for the bluing reaction seen in many bolete mushrooms when they are injured. When mushroom tissue containing variegatic acid is exposed to air, the chemical is enzymatically oxidized to blue quinone methide anions.[1] It is derived from xerocomic acid, which is preceded by atromentic acid and atromentin, and its genetic basis is unknown. In its oxidized form (due to the production of a second lactone ring) is variegatorubin, similar to xerocomorubin. It was first isolated from Suillus variegatus.[2] It has strong antioxidant properties,[3][4] and a nonspecific inhibitory effect on cytochrome P450 enzymes.[5] A total synthesis was reported in 2001 that uses a Suzuki cross coupling reaction. It was found antibiotically inactive against an array of bacteria and fungi using the disk diffusion assay at 50 μg.[7]. However, at similar concentrations it was found to inhibit swarming and (probably consequently) biofilm formation of Bacillus subtilis. In vitro data supports that this pigment is an Fe3+-reducant in Fenton chemistry during the initial attack of dead plant matter as part of the brown-rot saprobic lifestyle.[8] DerivativesVariegatic acid methyl ester, 3-O-methylvariegatic acid methyl ester, and 3,3',4,4'-tetra-O-methylvariegatic acid methyl ester are red-orange pigments found in Boletales.[9][10] See also
References1. ^1 {{cite journal |vauthors=Edwards RL, Elsworthy GC |title=Variegatic acid, a new tetronic acid responsible for the blueing reaction in the fungus Suillus (Boletus) variegatus (Swartz ex Fr.) |journal=Chemical Communications (London) |year=1967 |issue=8 |pages=373b–374 |doi=10.1039/C1967000373B}} [1][2][3][4][5][6][7][8][9]2. ^1 {{cite journal |vauthors=Huang YT, Onose J, Abe N, Yoshikawa K |title=In vitro inhibitory effects of pulvinic acid derivatives isolated from Chinese edible mushrooms, Boletus calopus and Suillus bovinus, on cytochrome P450 activity |journal=Bioscience, Biotechnology, and Biochemistry |year=2009 |volume=73 |issue=4 |pages=855–60 |pmid=19352038 |doi=10.1271/bbb.80759}} {{open access}} 3. ^1 {{cite journal |vauthors=Kasuga A, Aoyagi Y, Sugahara T |title=Antioxidant activity of fungus Suillus bovinus (L: Fr.) O. Kuntze |journal=Journal of Food Science |year=1995 |volume=60 |issue=5 |pages=1113–85 |doi=10.1111/j.1365-2621.1995.tb06304.x}} 4. ^1 {{cite journal |vauthors=Velíšek J, Cejpek K |title=Pigments of higher fungi: A review |journal=Czech Journal of Food Science |year=2011 |volume=29 |issue=2 |pages=87–102 |url=http://www.agriculturejournals.cz/publicFiles/37205.pdf |format=PDF}} 5. ^1 {{cite journal |vauthors=Vidovic SS, Mujic IO, Zekovic ZP, Lepojevic ZD, Tumbas VT, Mujic AI |title=Antioxidant properties of selected Boletus mushrooms |journal=Food Biophysics |year=2010 |volume=5 |issue=1 |pages=49–58 |doi=10.1007/s11483-009-9143-6}} 6. ^1 Tauber, J. P., Schroeckh, V., Shelest, E., Brakhage, A. A. and Hoffmeister, D. (2016), Bacteria induce pigment formation in the basidiomycete Serpula lacrymans. Environ Microbiol, 18: 5218–5227. doi:10.1111/1462-2920.13558 7. ^1 Eastwood et al. (2011) The Plant Cell Wall- Decomposing Machinery Underlies the Functional Diversity of Forest Fungi. Science. 8. ^1 Gill, M., and Steglich, W. (1987) Pigments of fungi (Macromycetes). Prog Chem Org Nat Prod 51: 1–317. 9. ^1 https://edoc.ub.uni-muenchen.de/783/1/Gruber_Gertraud.pdf }} 5 : Biological pigments|Polyphenols|Furanones|Catechols|Carboxylic acids |
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