Hypericin

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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 naphthodianthrone, an anthraquinone derivative which, together with hyperforin, is one of the principal active constituents of Hypericum (Saint John's wort). [2] [3] Hypericin is believed to act as an antibiotic, antiviral [2] and non-specific kinase inhibitor. Hypericin may inhibit the action of the enzyme dopamine β-hydroxylase, leading to increased dopamine levels,[ citation needed ] although thus possibly decreasing norepinephrine and epinephrine.

It was initially believed that the anti-depressant pharmacological activity of hypericin was due to inhibition of monoamine oxidase enzyme [4] . The crude extract of Hypericum is a weak inhibitor of MAO-A and MAO-B. [5] [6] Isolated hypericin does not display this activity, but does have some affinity for NMDA receptors. [7] This points in the direction that other constituents are responsible for the MAOI effect. The current belief is that the mechanism of antidepressant activity is due to the inhibition of re-uptake of certain neurotransmitters. [2]

The large chromophore system in the molecule means that it can cause photosensitivity when ingested beyond threshold amounts.[ citation needed ] Photosensitivity is often seen in animals that have been allowed to graze on St. John's Wort.[ citation needed ] Because hypericin accumulates preferentially in cancerous tissues, it is also used as an indicator of cancerous cells.[ citation needed ] In addition, hypericin is under research as an agent in photodynamic therapy, whereby a biochemical is absorbed by an organism to be later activated with spectrum-specific light from specialized lamps or laser sources, for therapeutic purposes.[ citation needed ] The antibacterial and antiviral effects of hypericin are also believed to arise from its ability for photo-oxidation of cells and viral particles. [2]

Hypericin derives from cyclisation of polyketides. [8] [9]

The biosynthesis of hypericins is through the polyketide pathway where an octaketide chain goes through successive cyclizations and decarboxylations to form emodin anthrone which is believed to be the precursor of hypericin. Oxidization reactions yield protoforms which then are converted into hypericin and pseudohypericin. These reactions are photosensitive and take place under exposure to light and using the enzyme Hyp-1. [10] [11] [12] [13] [14]

References

  1. ↑ Merck Index , 11th Edition, 4799
  2. 1 2 3 4 Mehta S (2012-12-18). "Pharmacognosy of St. John's Wort". Pharmaxchange.info. Retrieved 2014-02-16.
  3. ↑ Oubre A (1991). "Hypericin: the active ingredient in Saint John's Wort". Archived from the original on September 28, 2007. Retrieved September 18, 2006.
  4. ↑ 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
  5. ↑ Thiede HM, Walper A (October 1994). "Inhibition of MAO and COMT by hypericum extracts and hypericin". Journal of Geriatric Psychiatry and Neurology. 7 (Suppl 1): S54–56. doi:10.1177/089198879400700114. ISSN   0891-9887. PMID   7857510. S2CID   208042437.
  6. ↑ 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.
  7. ↑ Cott J (September 1997). "In Vitro Receptor Binding and Enzyme Inhibition by Hypericum perforatum Extract". Pharmacopsychiatry. 30 (S 2): 108–112. doi:10.1055/s-00000054.
  8. ↑ Loren W. Walker (1999). "A Review of the Hypothetical Biogenesis and Regulation of Hypericin synthesis via the Polyketide Pathway in Hypericum perforatum and Experimental Methods Proposed to Evaluate the Hypothesis". Archived from the original on 2019-06-26. Retrieved 2011-01-04.{{cite journal}}: Cite journal requires |journal= (help)
  9. ↑ Christian Hertweck (2009). "Polyketide Biosynthesis". Angew. Chem. Int. Ed. 48 (26): 4688–4716. doi:10.1002/anie.200806121. PMID   19514004.
  10. ↑ Karioti A, Bilia AR (2010). "Hypericins as potential leads for new therapeutics". Int J Mol Sci. 11 (2): 562–594. doi: 10.3390/ijms11020562 . PMC   2852855 . PMID   20386655.
  11. ↑ 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.
  12. ↑ 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.
  13. ↑ 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.
  14. ↑ 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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