• Korean Journal of Medicinal Crop Science
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• v.13 no.3
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• pp.101-104
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• 2005

To explore the Korea native plants to substitute for St. John's wort, which produce hypericin that use commercially for the treatment of mild to moderate depression, hypericin contents of Hypericum erectum and H. ascyron collected in two mountain of Korea were examined. From TLC and TLC-densitometer analysis of hypericin contents and biosynthetic pattern, hypericin was detected in flower and leaf of H. erectum, but not in all organs of H. ascyron. The hypericin content of H. erectum grown 200 m high hill in Mt. Byoung-pung was higher than that of Mt. Ji-ri 500 m and 1300 m high hill. When the seasonal variation of hypericin contents in H. erectum leaf collected from two regions was investigated, leaf collected from both regions on July was higher than other seasons.

• Archives of Pharmacal Research
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• v.21 no.1
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• pp.41-45
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• 1998

Hypericin, a photosensitizing plant pigment, was found to be a potent inducer of differentiation of human myeloid leukemia U-937 cells. At a concentration of $0.2{\mu}M$, hypericin exhibited 50% growth inhibition. An effect on cell differentiation by hypericin was assessed by its ability to induce phagocytosis of latex particles, and to reduce nitroblue tetrazolium (NBT). Approximately 51% of $0.2{\mu}M$ hypericin-treated cells were stained with NBT and 63% showed phagocytic activity. In order to establish whether hypericin induces differentiation of U-937 cells to macrophage or granulocyte, esterase activities and cell sizes were measured. When U-937 cells were treated with $0.2{\mu}M$ and $0.15{\mu}M$ of hypericin, the .alpha.-naphthyl acetate esterase activity was increased by 38.4% and 48.1%, respectively, but naphthol AS-D chloroacetate esterase activity was not influenced. The size of hypericin-treated cells in terms of cell mass was larger than that observed in untreated cells as determined by flow cytometry. Protein kinase C (PKC) inhibitor, NA-382, decreased the NBT reducing activity of hypericin, whereas a cAMP-dependent protein kinase A (PKA) inhibitor, H-89, did not show any influence on the differentiations. These results indicate that hypericin triggers differentiation toward monocyte/macrophage lineage by PKC stimulation.

• Biomolecules & Therapeutics
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• v.25 no.2
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• pp.158-164
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• 2017

Methylglyoxal (MGO) is a highly reactive metabolite of glucose which is known to cause damage and induce apoptosis in endothelial cells. Endothelial cell damage is implicated in the progression of diabetes-associated complications and atherosclerosis. Hypericin, a naphthodianthrone isolated from Hypericum perforatum L. (St. John's Wort), is a potent and selective inhibitor of protein kinase C and is reported to reduce neuropathic pain. In this work, we investigated the protective effect of hypericin on MGO-induced apoptosis in human umbilical vein endothelial cells (HUVECs). Hypericin showed significant anti-apoptotic activity in MGO-treated HUVECs. Pretreatment with hypericin significantly inhibited MGO-induced changes in cell morphology, cell death, and production of intracellular reactive oxygen species. Hypericin prevented MGO-induced apoptosis in HUVECs by increasing Bcl-2 expression and decreasing Bax expression. MGO was found to activate mitogen-activated protein kinases (MAPKs). Pretreatment with hypericin strongly inhibited the activation of MAPKs, including P38, JNK, and ERK1/2. Interestingly, hypericin also inhibited the formation of AGEs. These findings suggest that hypericin may be an effective regulator of MGO-induced apoptosis. In conclusion, hypericin downregulated the formation of AGEs and ameliorated MGO-induced dysfunction in human endothelial cells.

• Archives of Pharmacal Research
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• v.19 no.6
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• pp.490-496
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• 1996

Naphtodianthrone hypericin produced a potent antitumor activity in vitro against several tumor cells. However, it did not show any cytotoxicity on normal cells such as Macaccus rheus monkey kidney cells (MA-104) and primary cultured rat hepatocytes up to $500{\mu}M$ concentration. Hypericin added to A431 human epidermoid carcinoma cell membrane inhibited the autophosphorylation of the epidermal growth factor (EGF) receptor and the tyrosine phosphorylation of RR-SRC peptide catalyzed by an EGF-receptor. Similarly, treatment of the A431 cells with hypericin inhibited the tyrosine phosphorylation of EGF-dependent endogenous EGF-receptor by western blotting analysis. Hypericin also inhibited the T cell PTK, $P56^{lck}$, in a dose-dependent fashion with an $IC_{50}=5{\mu}M$. The tyrosine phosphorylation, on RR-SRC peptide and EGF-induced receptor autophosphorylation, either in vitro or in intact cells was inhibited by hypericin at the same concentration as that in A431 cell proliferation. These data suggest that hypericin directly inhibits EGF-receptor and $P56^{lck}$ PTK activity in vitro and can mediate such action in vivo.

• Journal of Photoscience
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• v.9 no.2
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• pp.524-526
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• 2002

Hypericin was found to exhibit the highest antitumoral activity in treating EAT by photodynamic therapy (PDT): Hypericin>HPde>PII>TPPS$_4$>ALA. Moreover, 25% of mice after Hyp-based PDT survived 4 months, if compare with control group. Antitumor activity of these photosensitizers was in rather clear correlation with accumulation potential.

• Bulletin of the Korean Chemical Society
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• v.29 no.10
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• pp.2023-2025
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• 2008

To evaluate the potential of radioiodine labelled hypericin as a malignant glioma imaging agent, U-251 MG, U-373 MG, C6 glioma and fibroblast were treated with a I-123 labelled hypericin derivative and C6 glioma transplanted nude mouse were injected with a I-124 labelled hypericin derivative for a micro PET imaging. 2- Iodohypericin was prepared as a reference compound. In this paper, we describe the syntheses of 2- iodohypericin and 2-[$^{123}I/^{124}I$]iodohypericin and the results of a corresponding biological evaluation. In all glioma cell lines, 2-[$^{123}I$]iodohypericin uptake was increased in a time dependant manner and an accumulation of 2-[$^{124}I$]iodohypericin was observed in C6 glioma bearing nude mouse. These results suggest that radioiodine labelled hypericin can visualize a PKC overexpressed malignant glioma.

• Bulletin of the Korean Chemical Society
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• v.25 no.8
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• pp.1147-1150
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• 2004

Hypericin (1,3,4,6,8,13-hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylene-7,14-dione), an antidepressant which is also known to be a potent protein kinase C (PKC) inhibitor was synthesized as a precursor for radioiodine labeling via two step reactions. Malignant glioma cells express higher PKC activity compared to untransformed glial cell. Here we report the synthesis and radioiodine labeling of hypericin as a potential brain tumor imaging radiopharmaceutical. The reference compound, 2-iodohypericin, and its radiolabelled analogues, 2-[$^{123}I$]iodohypericin and 2-[$^{124}I$]iodohypericin have been prepared by the reaction of hypericin with NaI or [$^{123}I$]NaI or [$^{124}I$]NaI. The labeling yield was 60-65% for each analogue and the optimal reaction time was 10 min. The purification and isolation of the labelled products were achieved by a reversed-phase HPLC.

• Analytical Science and Technology
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• v.8 no.4
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• pp.699-705
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• 1995

Monolayers of hypericin, a photodynamic polycyclic quinoidal compound, were prepared at the air-water interface, and were transferred to metal substrates to form Langmuir-Blodgett (LB) monolayers. The structural characteristics of hypericin LB monolayers and self-assembled (SA) monolayers were investigated using surface-enhanced resonance Raman scattering (SERRS) spectroscopy. Both the spectroscopic data and the surface pressure - area (${\pi}-A$) isotherms suggest that hypericin forms ${\pi}-{\pi}$ aggregates that orient vertically to the subphase surface. Whereas the ordering and orientation of control was less effective in SA monolayers, a higher structural regularity was attained in LB systems. The effect of subphase on the structural integrity of the monolayer was also investigated.

• Bulletin of the Korean Chemical Society
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• v.6 no.5
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• pp.300-303
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• 1985

To understand the nature of the linkage between chromophore and apoprotein in the photoreceptor of Stentor coeruleus, a conformational analysis has been carried out on the dipeptide amides linked to the chromophore hypericin using an empirical potential function. The conformational energies for the dipeptide amides of Glu (OHyp)-X-NHMe, where X = Leu, Phe, Asp, and Tyr, have been calculated to investigate the influence of peptide residues in stabilizing conformers. It was found that the increase of acidity of hypericin upon photoexcitation may be facilitated by the formation of intramolecular hydrogen bonds between hydroxyl groups of hypericin and carbonyl groups of peptide backbone, and that the stabilities of dipeptide amides do not significantly depend on peptide residues directly linked to chromophore.

• Journal of Life Science
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• v.17 no.8 s.88
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• pp.1034-1038
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• 2007

Hypericin (HyH) is a substance which is isolated a medicinal herb, Hypericum perforatum L., commonly known as St. John's Wort. Hypericum erectum is a long-lived herb that is distributed in Korea. Cloned HyH genes H. erectum of were conformed by sequencing. The cDNA Hyp-1 sequence has 732 bp with an open reading frame of 567. Thus coding for a protein of 152 amino acid residues. A BLAST re-search using the deduced nucleotide sequences in HyH gene produced significant alignments with the H. perforatum. Sequences in HyH gene showed significant homology with Rubus idaeus putative allergen Rub-i-1 mRNA, Protein sequence comparisons revealed significant homology between Hyp-1 and the phenolic oxidative coupling protein hyp-1 of H. perforatum (98%). Additionally, Hyp-1 showed sig-nificant homology with various other classes of allergens, including Pru-av-1 (62%) from Prunus avium and allergen Bet-vl-Sc3 from Betula pendula (60%). Thus, the result of this study may offer an important information to establish an assay system for chemicals of the herbal medicines for H. erectum as well as H. perforatum.