| Identification | Back Directory | [Name]
HYPERFORIN | [CAS]
11079-53-1 | [Synonyms]
HYPERFORIN
HYPERFORIN MIX(P)
HYPERFORIN USP/EP/BP
Hyperforin (solution in Ethanol)
Bicyclo[3.3.1]non-3-ene-2,9-dione, 4-hydroxy-6-
methyl-1,3,7-tris(3-methyl-2-buten-1-yl)-5-(2-methyl-1-oxopropyl)-6-(4-methyl-3-penten-1-yl)-,(1R,5S,6R,7S)-
4-HYDROXY-6R-METHYL-1R,3,7S-TRIS(3-METHYL-2-BUTENYL)-5S-(2-METHYL-1-OXOPROPYL)-6R-(4-METHYL-3-PENTENYL)-BICYCLO[3.3.1]NON-3-ENE-2,9-DIONE
(1R,5S)-4-Hydroxy-6-methyl-1,3,7β-tris(3-methyl-2-butenyl)-5-(2-methyl-1-oxopropyl)-6α-(4-methyl-3-pentenyl)bicyclo[3.3.1]non-3-ene-2,9-dione
Bicyclo[3.3.1]non-3-ene-2,9-dione,4-hydroxy-6-methyl-1,3,7-tris(3-methyl-2-buten-1-yl)-5-(2-methyl-1-oxopropyl)-6-(4-methyl-3-penten-1-yl)-,(1R,5S,6R,7S)- | [EINECS(EC#)]
601-000-9 | [Molecular Formula]
C35H52O4 | [MDL Number]
MFCD01861497 | [MOL File]
11079-53-1.mol | [Molecular Weight]
536.78 |
| Chemical Properties | Back Directory | [Melting point ]
79-80℃ | [alpha ]
D18 +41° (in ethanol) | [Boiling point ]
616.8±55.0 °C(Predicted) | [density ]
1.010±0.06 g/cm3 (20 ºC 760 Torr) | [Fp ]
9℃ | [storage temp. ]
-20°C | [form ]
solution
| [pka]
4.8 (50% aq ethanol) | [CAS DataBase Reference]
11079-53-1 |
| Hazard Information | Back Directory | [Uses]
St. John’s wort is a widely consumed herbal preparation which has been claimed to have a number of medicinal properties. It contains a number of known lipid signalling mediators, including chlorogenic acid, hypericin, hyperforin, and I3,II8-biapigenin. Hyperforin exhibits two activities which may alter the action of other concurrent medications. It inhibits the activity of several CYP450 enzymes, with CYP2D6 being the most sensitive with an IC50 of about 10 μg/ml. Hyperforin is also a ligand for the steroid X receptor (SXR). Since one activity of this receptor is the induction of CYP450 expression, the exact nature of hyperforin’s drug-drug interactions must be evaluated on a case-by-case basis. However, these interactions certainly complicate its use as a human therapeutic.[Cayman Chemical] | [Definition]
ChEBI: A cyclic terpene ketone that is a prenylated carbobicyclic acylphloroglucinol derivative produced by St. John's Wort, Hypericum perforatum. | [General Description]
Hyperforin is a phloroglucinol component of St. John′s wort and a pregnane X receptor ligand. | [Biochem/physiol Actions]
Hyperforin is an active antidepressant and an inhibitor of cytochrome P450 3A4 (CYP3A). It elicits antioxidant and antibacterial activity. Hyperforin is also embryotoxic and inhibits tumor proliferation. It effectively inhibits dopamine, serotonin and norepinephrine. | [Synthesis]
Low temperature ultrasonic extraction process: weigh 10g of crushed Hypericum perforatum powder, placed in a 500mL beaker, add 10 times the amount of 75% ethanol and mix according to the volume ratio, add the appropriate amount of antioxidants, according | [in vivo]
Hyperforin (5 mg/kg; i.p.; once daily for 7 d) ameliorates Imiquimod (HY-B0180)-induced psoriatic skin lesion in mice, as well as inhibiting inflammatory cell infiltration and inflammatory cytokines release[3].
| Animal Model: | IMQ-induced psoriasis-like mice model[3] | | Dosage: | 5 mg/kg | | Administration: | Intraperitoneal injection; once daily for 7 days | | Result: | Significantly ameliorated skin lesion throughout the treatment period, demonstrated by the reduced severity score of skin inflammation.
Suppressed infiltration of CD3+ T cells and downregulated expression of Il1, Il6, Il23, Il17a, Il22, antimicrobial peptides (AMPs) in the skin lesion. |
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