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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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Determination of hypericin and hyperforin content in selected Jordanian Hypericum species
Tawaha K, et al.
Industrial Crops and Products, 32(3), 241-245 (2010)
L B Moore et al.
Proceedings of the National Academy of Sciences of the United States of America, 97(13), 7500-7502 (2000-06-15)
St. John's wort (Hypericum perforatum) is an herbal remedy used widely for the treatment of depression. Recent clinical studies demonstrate that hypericum extracts increase the metabolism of various drugs, including combined oral contraceptives, cyclosporin, and indinavir. In this report, we
Mohamed A Farag et al.
Planta medica, 78(5), 488-496 (2012-01-25)
The growing interest in the efficacy of phytomedicines and herbal supplements but also the increase in legal requirements for safety and reliable contents of active principles drive the development of analytical methods for the quality control of complex, multicomponent mixtures
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
C Billard et al.
Current cancer drug targets, 13(1), 1-10 (2012-08-29)
Hyperforin is a prenylated phloroglucinol present in the medicinal plant St John's wort (Hypericum perforatum). The compound has many biological properties, including antidepressant, anti-inflammatory, antibacterial and antitumor activities. This review focuses on the in vitro antileukemic effects of purified hyperforin
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