238074-03-8 Usage
Description
Hyperforin is a natural activator of the steroid X receptor (active at 0.1 to 0.5 μg/ml) and inhibitor of several cytochrome P450 (CYP) isoforms (IC50 = 10 μg/ml for CYP2D6). It can also inhibit microsomal prostaglandin E2 synthase-1 (mPGES-1; IC50 = 1 μM), 5-lipoxygenase activating protein, and sirtuins.
General Description
This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG
Biochem/physiol Actions
Stable salt of hyperforin. Hyperforin is believed to be the primary active constituent responsible for the antidepressant and anxiolytic properties of the extracts of St. John′s wort. It acts as a reuptake inhibitor of monoamines, including serotonin, norepinephrine, dopamine, and of GABA and glutamate by activating the transient receptor potential ion channel TRPC6. Activation of TRPC6 induces the entry of sodium and calcium into the cell which causes inhibition of monoamine reuptake. It also is an activator of the pregnane X receptor (PXR), which serves as a key regulator of CYP3A4 transcription, a member of the cytochrome (CYP) P450 enzyme system. Recent studies have found other neurological effects, effects on inflammation, as well as antibacterial, antitumoral and antiangiogenic effects.
Check Digit Verification of cas no
The CAS Registry Mumber 238074-03-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,3,8,0,7 and 4 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 238074-03:
(8*2)+(7*3)+(6*8)+(5*0)+(4*7)+(3*4)+(2*0)+(1*3)=128
128 % 10 = 8
So 238074-03-8 is a valid CAS Registry Number.
238074-03-8Relevant articles and documents
In-vitro antitumor activity evaluation of hyperforin derivatives
Sun, Feng,Liu, Jin-Yun,He, Feng,Liu, Zhong,Wang, Rui,Wang, Dong-Mei,Wang, Yi-Fei,Yang, De-Po
experimental part, p. 688 - 699 (2011/09/21)
The derivatives of hyperforin, namely hyperforin acetate (2), 17,18,22,23,27,28,32,33-octahydrohyperforin acetate (3), and N, N-dicyclohexylamine salt of hyperforin (4), have been investigated for their antitumor properties. In-vitro studies demonstrated that 2 and 4 were active against HeLa (human cervical cancer), A375 (human malignant melanoma), HepG2 (human hepatocellular carcinoma), MCF-7 (human breast cancer), A549 (human nonsmall cell lung cancer), K562 (human chronic myeloid leukemia), and K562/ADR (human adriamycin-resistant K562) cell lines with IC50 values in the range of 3.2-64.1 μM. The energy differences between highest occupied molecular orbital and lowest unoccupied molecular orbital of 2-4 were calculated to be 0.39778, 0.43106, and 0.30900 a.u., respectively, using the Gaussian 03 software package and ab initio method with the HF/6-311 G* basis set. The result indicated that the biological activity of 4 might be the strongest and that of 3 might be the weakest, which was in accordance with their corresponding antiproliferative effects against the tested tumor cell lines. Compound 4 caused cell cycle arrest at G2/M phase in flow cytometry experiment and induced apoptosis by 4',6-diamidino-2-phenylindole staining and Annexin V-FITC/PI (propidium iodide) double-labeled staining in HepG2 cells. The results indicated a potential for N, N-dicyclohexylamine salt of hyperforin as a new antitumor drug.
