Hypericin

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Hypericin
Category Bioactive by-products
Catalog number BBF-05801
CAS 548-04-9
Molecular Weight 504.45
Molecular Formula C30H16O8
Purity >98%

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BBF-05801 10 mg $199 In stock

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Description

It is a natural antidepressant produced by the strain of Hypericium perforatum (plant extract). It is an anti-retroviral agent and protein kinaze-C inhibitor.

Specification

Synonyms Cyclo-Werol; Cyclosan; Hyperflav; Hypericum red; NSC 407313; Mycoporphyrin; 4,5,7,4',5',7'-Hexahydroxy-2,2'-dimethylnaphthodianthrone; 1:6:8:10:11:13-hexahydroxy-3:4-dimethyl-meso-naphthodianthrene-7:14-dione
Storage Store at RT
IUPAC Name 1,3,4,6,8,13-hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylene-7,14-dione
Canonical SMILES CC1=CC(=C2C3=C1C4=C5C(=C(C=C4C)O)C(=O)C6=C(C=C(C7=C6C5=C3C8=C7C(=CC(=C8C2=O)O)O)O)O)O
InChI InChI=1S/C30H16O8/c1-7-3-9(31)19-23-15(7)16-8(2)4-10(32)20-24(16)28-26-18(12(34)6-14(36)22(26)30(20)38)17-11(33)5-13(35)21(29(19)37)25(17)27(23)28/h3-6,31-36H,1-2H3
InChI Key BTXNYTINYBABQR-UHFFFAOYSA-N

Properties

Appearance Very Dark Red to Black Solid
Application Antineoplastic and antitumor
Antibiotic Activity Spectrum Viruses
Boiling Point 1020.3±65.0 °C | Condition: Press: 760 Torr
Melting Point 299-301°C
Flash Point 530.1±30.8 °C
Density 1.915±0.06 g/cm3 | Condition: Temp: 20 °C Press: 760 Torr
Solubility Soluble in DMSO (Slightly), Methanol (Slightly, Heated)

Reference Reading

1.Construction of Hypericin Gland-Specific cDNA Library via Suppression Subtractive Hybridization.
Singh RK1, Hou W1, Franklin G2,3. Methods Mol Biol. 2016;1391:317-34. doi: 10.1007/978-1-4939-3332-7_22.
Hypericin, an important determinant of the pharmacological properties of the genus Hypericum, is considered as a major molecule for drug development. However, biosynthesis and accumulation of hypericin is not well understood. Identification of genes differentially expressed in tissues with and without hypericin accumulation is a useful strategy to elucidate the mechanisms underlying the development of the dark glands and hypericin biosynthesis. Suppression Subtractive Hybridization (SSH) is a unique method for PCR-based amplification of specific cDNA fragments that differ between a control (driver) and experimental (tester) transcriptome. This technique relies on the removal of dsDNA formed by hybridization between a control and test sample, thus eliminating cDNAs of similar abundance, and retaining differentially expressed or variable in sequence cDNAs. In our laboratory we applied this method to identify the genes involved in the development of dark glands and accumulation of hypericin in Hypericum perforatum.
2.Photoactivated hypericin is not genotoxic.
Feruszová J1, Imreová P, Bodnárová K, Ševčovičová A, Kyzek S, Chalupa I, Gálová E, Miadoková E. Gen Physiol Biophys. 2016 Feb 18. [Epub ahead of print]
The study was designed to test the potential photogenotoxicity of hypericin (HYP) at three different levels: primary DNA damages, gene mutations and chromosome aberrations. Primary genetic changes were detected using the comet assay. The potential mutagenic activity of HYP was assessed using the Ames/Salmonella typhimurium assay. Finally, the ability of photoactivated HYP to induce chromosome aberrations was evaluated by the in vitro mammalian chromosome aberration test and compared to that of non-photoactivated HYP. The results have shown that photoactivated HYP can only induce primary DNA damages (single-strand DNA breaks), acting in a dose-response manner. This activity depended both on HYP concentrations and an intensity of the light energy needed for its photoactivation. However, mutagenic effect of photoactivated HYP evaluated in the Ames assay using three bacterial strains S. typhimurium (TA97, TA98 and TA100) was not confirmed. Moreover, photoactivated HYP in the range of concentrations (0.
3.Application of mathematical models for bacterial inactivation curves using Hypericin based photosensitization.
Dementavicius D1, Lukseviciute V1, Gómez-López VM1,2, Luksiene Z1. J Appl Microbiol. 2016 Mar 12. doi: 10.1111/jam.13127. [Epub ahead of print]
AIMS: The aim of this study was to evaluate which of the three mathematical models (Weibull, Geeraerd and Logistic) makes the best approximation for Hypericin based photosensitization bacterial inactivation.

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