{{cs1 config|name-list-style=vanc}} {{chembox | verifiedrevid = 443864519 | Reference=<ref>''Merck Index'', 11th Edition, '''4799'''</ref> | ImageFile = Hypericin2DACS.svg | ImageClass = skin-invert-image | ImageSize = 200px | ImageAlt = Structural formula of hypericin | ImageFile1 = Hypericin 3D ball.png | ImageClass1 = bg-transparent | ImageSize1 = 220px | ImageAlt1 = Ball-and-stick model of the hypericin molecule | PIN=1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-''opqra'']perylene-7,14-dione | OtherNames=4,5,7,4',5',7'-Hexahydroxy-2,2'-dimethylnaphthodianthrone |Section1={{Chembox Identifiers | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 7V2F1075HD | KEGG_Ref = | KEGG = D12433 | KEGG2_Ref = | KEGG2 = C07606 | InChI = 1/C30H16O8/c1-7-3-9(31)19-23-15(7)16-8(2)4-10(32)20-24(16)28-26-18(12(34)6-14(36)22(26)30(20)38)17-11(33)5-13(35)21(29(19)37)25(17)27(23)28/h3-6,31-36H,1-2H3 | InChIKey = BTXNYTINYBABQR-UHFFFAOYAC | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 286494 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C30H16O8/c1-7-3-9(31)19-23-15(7)16-8(2)4-10(32)20-24(16)28-26-18(12(34)6-14(36)22(26)30(20)38)17-11(33)5-13(35)21(29(19)37)25(17)27(23)28/h3-6,31-36H,1-2H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = BTXNYTINYBABQR-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo=548-04-9 | PubChem=5281051 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID=4444511 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 5835 | SMILES = Cc0cc(O)c1C(=O)c2c(O)cc(O)c3c2c4c1c0c5c6c4c7c3c(O)cc(O)c7C(=O)c6c(O)cc5C }} |Section2={{Chembox Properties | C=30 | H=16 | O=8 | Appearance= | Density= | MeltingPt= | BoilingPt= | Solubility= }} |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = }} }}
'''Hypericin''' is a carbopolycyclic compound derived from bisanthene with antidepressant properties, found in various ''Hypericum'' species, and is being studied for treating cutaneous T-cell lymphoma.<ref>{{Cite web |last=PubChem |title=Hypericin |url=https://pubchem.ncbi.nlm.nih.gov/compound/Hypericin |access-date=2025-05-22 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>
Opinions differ on the extent to which hypericin exhibits antidepressant effects. According to some scholars, hypericin, along with other active compounds in ''Hypericum perforatum'' (St. John’s wort), contributes to the antidepressant effects of the total plant extract.<ref>Butterweck, V., & Schmidt, M. (2007). St. John’s wort: Role of active compounds for its mechanism of action and efficacy. Wiener Medizinische Wochenschrift, 157(13-14), 356–361. https://doi.org/10.1007/s10354-007-0440-8</ref> According to others, hypericin does not significantly inhibit monoamine oxidase and thus is unlikely to account for the antidepressant effects of ''Hypericum'' extract.<ref>{{Cite journal|last1=Bladt|first1=S.|last2=Wagner|first2=H.|date=October 1994|title=Inhibition of MAO by fractions and constituents of hypericum extract|journal=Journal of Geriatric Psychiatry and Neurology|volume=7|issue=Suppl 1 |pages=S57–59|doi=10.1177/089198879400700115|issn=0891-9887|pmid=7857511|s2cid=23531061}}</ref> Another hypericin shows affinity mainly for NMDA receptors, suggesting that other plant constituents likely play a more significant role in its antidepressant effects.<ref>{{Cite journal |last=Cott |first=J. M. |date=1997 |title=In vitro receptor binding and enzyme inhibition by Hypericum perforatum extract |journal=Pharmacopsychiatry |volume=30 Suppl 2 |pages=108–112 |doi=10.1055/s-2007-979529 |issn=0176-3679 |pmid=9342770}}</ref>
Hypericin is a structurally complex phenanthroperylene quinone with potential medical and photoreceptive applications.<ref>{{cite journal |vauthors=Falk H |title=From the Photosensitizer Hypericin to the Photoreceptor Stentorin- The Chemistry of Phenanthroperylene Quinones |journal=Angew. Chem. Int. Ed. Engl. |volume=38 |issue=21 |pages=3116–3136 |date=1999 |pmid=10556884 |doi= 10.1002/(SICI)1521-3773(19991102)38:21<3116::AID-ANIE3116>3.0.CO;2-S}}</ref> It is red-colored, photosensitive compound whose biosynthesis is catalyzed by the gene Hyp-1, a Bet v 1-class allergen identified through red-color-based colony screening and shown to convert emodin to hypericin with high efficiency.<ref>{{cite journal |vauthors=Bais HP, Vepachedu R, Lawrence CB, Stermitz FR, Vivanco JM |title=Molecular and biochemical characterization of an enzyme responsible for the formation of hypericin in St. John's wort (Hypericum perforatum L.) |journal=J. Biol. Chem. |volume=278 |issue=34 |pages=32413–32422 |date=2003 |pmid=12799379 |doi=10.1074/jbc.M301681200 |doi-access= free}}</ref> It is thought to be synthesized by the PR-10 protein Hyp-1 through emodin dimerization, but despite confirming Hyp-1’s structure and ligand-binding capability, its catalytic role in hypericin biosynthesis remains unproven.<ref>{{cite journal |vauthors=Michalska K, Fernandes H, Sikorski M, Jaskolski M |title=Crystal structure of Hyp-1, a St. John's wort protein implicated in the biosynthesis of hypericin |journal=J. Struct. Biol. |volume=169 |issue=2 |pages=161–171 |date=2010 |pmid=19853038 |doi=10.1016/j.jsb.2009.10.008 }}</ref>
Biotechnological research is exploring ''in vitro'' culture methods to enhance and stabilize the production of hypericin.<ref>{{cite journal |vauthors=Murthy HN, Kim YS, Park SY, Paek KY |title=Hypericins: biotechnological production from cell and organ cultures |journal=Appl. Microbiol. Biotechnol. |volume=98 |issue=22 |pages=9187–9198 |date=2014 |pmid=25301586 |doi=10.1007/s00253-014-6119-3 |s2cid=17487401 }}</ref>
== References == {{Reflist|2}}
{{Glutamate receptor modulators}} {{Sigma receptor modulators}}
Category:Virucides Category:Polyketides Category:Polyols Category:Chemicals in Hypericum Category:Biological pigments Category:3-Hydroxypropenals within hydroxyquinones