Hypericin

Last updated

Hypericin [1]
Hypericin2DACS.svg
Hypericin 3D ball.png
Names
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
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.129 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=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 Yes check.svgY
    Key: BTXNYTINYBABQR-UHFFFAOYSA-N Yes check.svgY
  • 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
    Key: BTXNYTINYBABQR-UHFFFAOYAC
  • Cc0cc(O)c1C(=O)c2c(O)cc(O)c3c2c4c1c0c5c6c4c7c3c(O)cc(O)c7C(=O)c6c(O)cc5C
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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

  1. ↑ Merck Index , 11th Edition, 4799
  2. ↑ PubChem. "Hypericin". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-05-22.
  3. ↑ 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
  4. ↑ 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.
  5. ↑ 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.
  6. ↑ 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.
  7. ↑ 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.
  8. ↑ 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.
  9. ↑ 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.
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