Pseudohypericin

Last updated
Pseudohypericin
Pseudohypericin2DACS.svg
Names
Preferred IUPAC name
1,3,4,6,8,13-Hexahydroxy-10-(hydroxymethyl)-11-methylphenanthro[3,4,5,6-fghij]perylene-7,14-dione
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.111.993 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 611-335-2
KEGG
PubChem CID
UNII
  • InChI=1S/C30H16O9/c1-7-2-9(32)19-23-15(7)16-8(6-31)3-10(33)20-24(16)28-26-18(12(35)5-14(37)22(26)30(20)39)17-11(34)4-13(36)21(29(19)38)25(17)27(23)28/h2-5,31,34-39H,6H2,1H3
    Key: NODGUBIGZKATOM-UHFFFAOYSA-N
  • CC1=CC(=O)C2=C(C3=C(C=C(C4=C3C5=C6C7=C(C1=C25)C(=CC(=O)C7=C(C8=C(C=C(C4=C86)O)O)O)CO)O)O)O
Properties
C30H16O9
Molar mass 520.449 g·mol−1
log P 4.5
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Pseudohypericin is an aromatic polycyclic dione that is very closely related to hypericin. It is found most commonly in the St. John's wort family of plants, namely in Hypericum perforatum . [1] In preliminary studies in animal models, pseudohypericin has shown antiviral effects. [2] [3] It may also contribute to the potential antidepressant effect of Hypericum perforatum extracts. [4]

Related Research Articles

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<i>Hypericum perforatum</i> Flowering plant in the St Johns wort family Hypericaceae

Hypericum perforatum, known as perforate St John's-wort, is a flowering plant in the family Hypericaceae and the type species of the genus Hypericum.

<i>Hypericum calycinum</i> Species of flowering plant in the St Johns wort family Hypericaceae

Hypericum calycinum is a species of prostrate or low-growing shrub in the flowering plant family Hypericaceae. Widely cultivated for its large yellow flowers, its names as a garden plant include Rose-of-Sharon in Britain and Australia, and Aaron's beard, great St-John's wort, creeping St. John's wort and Jerusalem star. Grown in Mediterranean climates, widely spread in the Strandja Mountains along the Bulgarian and Turkish Black Sea coast, and also in Flanders in Belgium.

Polycyclic aromatic hydrocarbon Hydrocarbon composed of multiple aromatic rings

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Hypericin Chemical compound

Hypericin is a naphthodianthrone, an anthraquinone derivative which, together with hyperforin, is one of the principal active constituents of Hypericum. Hypericin is believed to act as an antibiotic, antiviral and non-specific kinase inhibitor. Hypericin may inhibit the action of the enzyme dopamine β-hydroxylase, leading to increased dopamine levels, although thus possibly decreasing norepinephrine and epinephrine.

Methylcholanthrene Chemical compound

Methylcholanthrene is a highly carcinogenic polycyclic aromatic hydrocarbon produced by burning organic compounds at very high temperatures. Methylcholanthrene is also known as 3-methylcholanthrene, 20-methylcholanthrene or the IUPAC name 3-methyl-1,2-dyhydrobenzo[j]aceanthrylene. The short notation often used is 3-MC or MCA. This compound forms pale yellow solid crystals when crystallized from benzene and ether. It has a melting point around 180 °C and its boiling point is around 280 °C at a pressure of 80 mmHg. Methylcholanthrene is used in laboratory studies of chemical carcinogenesis. It is an alkylated derivative of benz[a]anthracene and has a similar UV spectrum. The most common isomer is 3-methylcholanthrene, although the methyl group can occur in other places.

Hyperforin

Hyperforin is a phytochemical produced by some of the members of the plant genus Hypericum, notably Hypericum perforatum. Hyperforin may be involved in the pharmacological effects of St. John's wort, specifically in its antidepressant effects.

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Deoxycytidine kinase

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TRPC6

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<i>Hypericum androsaemum</i> Species of flowering plant in the St Johns wort family Hypericaceae

Hypericum androsaemum, also referred to as Tutsan, Shrubby St. John's Wort, or sweet-amber, is a flowering plant in the family Hypericaceae. It is a perennial shrub reaching up to 70 cm in height, native to open woods and hillsides in Eurasia.

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Adhyperforin

Adhyperforin is a phytochemical found in the members of the plant genus Hypericum including St. John's Wort. It has a very similar pharmacological profile to hyperforin and acts as a TRPC6 ion channel activator, thereby inhibiting the reuptake of various neurotransmitters including serotonin, norepinephrine, dopamine, GABA, and glutamate. Adhyperforin is found in St. John's Wort in levels approximately 1/10 those of hyperforin.

<i>Hypericum olympicum</i> species of flowering plant in the St Johns wort family Hypericaceae

Hypericum olympicum, commonly known as the Mount Olympus St. John's wort, is a species of flowering plant in the family Hypericaceae found in the Balkans and Turkey and introduced to western Europe. It has been widely cultivated for centuries because of its large, showy flowers, which are far larger than those of most other species in Hypericum.

Miquelianin Chemical compound

Miquelianin is a flavonol glucuronide, a type of phenolic compound present in wine, in species of St John's wort, like Hypericum hirsutum, in Nelumbo nucifera or in green beans.

<i>Hypericum formosissimum</i> Species of flowering plant in the St Johns wort family Hypericaceae

Hypericum formosissimum is a species of flowering plant in the family Hypericaceae, section Adenosepalum, in the Hypericum huber-morathii group.

<i>Hypericum heterophyllum</i> Species of flowering plant in the St Johns wort family Hypericaceae

Hypericum heterophyllum is a flowering plant in the Hypericaceae family and is the only species in Hypericum sect. Heterophylla.

References

  1. Kitanov, Gerassim M. (2001). "Hypericin and pseudohypericin in some Hypericum species". Biochemical Systematics and Ecology. 29 (2): 171–178. doi:10.1016/S0305-1978(00)00032-6. PMID   11106845.
  2. Meruelo, D.; Lavie, G.; Lavie, D. (1988). "Therapeutic agents with dramatic antiretroviral activity and little toxicity at effective doses: Aromatic polycyclic diones hypericin and pseudohypericin". Proceedings of the National Academy of Sciences. 85 (14): 5230–5234. Bibcode:1988PNAS...85.5230M. doi:10.1073/pnas.85.14.5230. PMC   281723 . PMID   2839837.
  3. Hudson, J.B.; Lopez-Bazzocchi, I.; Towers, G.H.N. (1991). "Antiviral activities of hypericin". Antiviral Research. 15 (2): 101–112. doi:10.1016/0166-3542(91)90028-P. PMID   1650164.
  4. Butterweck, Veronika; Petereit, Frank; Winterhoff, Hilke; Nahrstedt, Adolf (1998). "Solubilized Hypericin and Pseudohypericin from Hypericum perforatum Exert Antidepressant Activity in the Forced Swimming Test3". Planta Medica. 64 (4): 291–294. doi:10.1055/s-2006-957437. PMID   9619107.