Hypericin
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| Names | |
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| Preferred IUPAC name
1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylene-7,14-dione | |
| Other names
4,5,7,4',5',7'-Hexahydroxy-2,2'-dimethylnaphthodianthrone
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.008.129 |
| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C30H16O8 | |
| Molar mass | 504.450 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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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.[2]
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.[3] According to others, hypericin does not significantly inhibit monoamine oxidase and thus is unlikely to account for the antidepressant effects of Hypericum extract.[4] While another hypericin shows affinity mainly for NMDA receptors, suggesting that other plant constituents likely play a more significant role in its antidepressant effects.[5]
Hypericin is a structurally complex phenanthroperylene quinone with potential medical and photoreceptive applications.[6] 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.[7] 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.[8]
Biotechnological research is exploring in vitro culture methods to enhance and stabilize the production of hypericin.[9]
References
[edit]- ^ Merck Index, 11th Edition, 4799
- ^ PubChem. "Hypericin". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-05-22.
- ^ 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
- ^ Bladt S, Wagner H (October 1994). "Inhibition of MAO by fractions and constituents of hypericum extract". Journal of Geriatric Psychiatry and Neurology. 7 (Suppl 1): S57–59. doi:10.1177/089198879400700115. ISSN 0891-9887. PMID 7857511. S2CID 23531061.
- ^ Cott JM (1997). "In vitro receptor binding and enzyme inhibition by Hypericum perforatum extract". Pharmacopsychiatry. 30 Suppl 2: 108–112. doi:10.1055/s-2007-979529. ISSN 0176-3679. PMID 9342770.
- ^ Falk H (1999). "From the Photosensitizer Hypericin to the Photoreceptor Stentorin- The Chemistry of Phenanthroperylene Quinones". Angew. Chem. Int. Ed. Engl. 38 (21): 3116–3136. doi:10.1002/(SICI)1521-3773(19991102)38:21<3116::AID-ANIE3116>3.0.CO;2-S. PMID 10556884.
- ^ Bais HP, Vepachedu R, Lawrence CB, Stermitz FR, Vivanco JM (2003). "Molecular and biochemical characterization of an enzyme responsible for the formation of hypericin in St. John's wort (Hypericum perforatum L.)". J. Biol. Chem. 278 (34): 32413–32422. doi:10.1074/jbc.M301681200. PMID 12799379.
- ^ Michalska K, Fernandes H, Sikorski M, Jaskolski M (2010). "Crystal structure of Hyp-1, a St. John's wort protein implicated in the biosynthesis of hypericin". J. Struct. Biol. 169 (2): 161–171. doi:10.1016/j.jsb.2009.10.008. PMID 19853038.
- ^ Murthy HN, Kim YS, Park SY, Paek KY (2014). "Hypericins: biotechnological production from cell and organ cultures". Appl. Microbiol. Biotechnol. 98 (22): 9187–9198. doi:10.1007/s00253-014-6119-3. PMID 25301586. S2CID 17487401.