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H5160

Sigma-Aldrich

Hyperforin

≥85% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C35H52O4
CAS Number:
11079-53-1
Molecular Weight:
536.78
EC Number:
200-659-6
MDL number:
MFCD01861497
UNSPSC Code:
12352200
PubChem Substance ID:
329815216
NACRES:
NA.77

Quality Level

100

Assay

≥85% (HPLC)

form

solution

storage temp.

−20°C

SMILES string

CC(C)C(=O)[C@@]12C(O)=C(C\C=C(\C)C)C(=O)[C@@](C\C=C(/C)C)(C[C@H](C\C=C(\C)C)[C@@]1(C)CC\C=C(\C)C)C2=O

InChI

1S/C35H52O4/c1-22(2)13-12-19-33(11)27(16-14-23(3)4)21-34(20-18-25(7)8)30(37)28(17-15-24(5)6)31(38)35(33,32(34)39)29(36)26(9)10/h13-15,18,26-27,38H,12,16-17,19-21H2,1-11H3/t27-,33+,34+,35-/m0/s1

InChI key

IWBJJCOKGLUQIZ-HQKKAZOISA-N

General description

Hyperforin is a phloroglucinol component of St. John′s wort and a pregnane X receptor ligand.

Application

Hyperforin may be used:
  • as a reference standard for calibration curve generation in high-perfornamce liquid chromatography (HPLC) analysis
  • to test its cytotoxic effect and apoptosis induction in mouse embryonic cells
  • as a pregnane X receptor (PXR) in porcine brain capillary endothelial cells for transport assay

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.

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Flam. Liq. 2 - STOT SE 1

Target Organs

Eyes

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

49.5 °F - closed cup

Flash Point(C)

9.7 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Martina C Meinke et al.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V, 81(2), 346-350 (2012-03-21)
Hyperforin, a major constituent of St. John's Wort (Hypericum perforatum, HP), provides anti-inflammatory, anti-tumor, and anti-bacterial properties. Previous studies have shown anti-oxidative properties of St. John's Wort extracts; however, its free radical scavenging activity in skin cells or skin has
Rajanikanth Madabushi et al.
European journal of clinical pharmacology, 62(3), 225-233 (2006-02-16)
Recently, interactions of herbal medicines with synthetic drugs came into focus of particular interest. In the past 3 years, more than 50 papers were published regarding interactions between St. John's wort (Hypericum perforatum L.; SJW) and prescription drugs. Co-medication with
Induction and inhibition of cytochromes P450 by the St. John's wort constituent hyperforin in human hepatocyte cultures
Komoroski BJ, et al.
Drug Metabolism and Disposition, 32(5), 512-518 (2004)
Murhaf Zaher et al.
International journal of oncology, 40(1), 269-276 (2011-09-29)
We previously reported that hyperforin, a phloroglucinol purified from Hypericum perforatum, induces the mitochondrial pathway of caspase-dependent apoptosis in chronic lymphocytic leukemia (CLL) cells ex vivo, and that this effect is associated with upregulation of Noxa, a BH3-only protein of
Jeffry Adiwidjaja et al.
Clinical pharmacokinetics, 58(7), 911-926 (2019-01-25)
Herb-drug interactions with St John's wort (SJW) have been widely studied in numerous clinical studies. The objective of this study was to develop and evaluate a physiologically based pharmacokinetic (PBPK) model for hyperforin (the constituent of SJW responsible for interactions)
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