Editing Hypericin

{{cs1 config|name-list-style=vanc}}
{{chembox
| verifiedrevid = 443864519
| Reference=<ref>''[[Merck Index]]'', 11th Edition, '''4799'''</ref>
| ImageFile = Hypericin2DACS.svg
| ImageSize = 200px
| ImageAlt = Structural formula of hypericin
| ImageFile1 = Hypericin 3D ball.png
| 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 [[Skin|cutaneous]] [[T-cell lymphoma|T-cell]] [[T-cell lymphoma|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 [[Monoamine oxidase inhibitor|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>  While another hypericin shows affinity mainly for [[NMDA receptor|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 |url=https://pubmed.ncbi.nlm.nih.gov/9342770 |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 [[Evidence-based medicine|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 [[Catalysis|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]]