• 한국약용작물학회지
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• 제13권3호
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• pp.101-104
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• 2005

2003년 6, 8월에 지리산과 전남 담양군의 병풍산에서 자생하는 고추나물과 물레나물을 채집하여 TLC 분석을 하고, TLC-densitometry를 이용해 정량한 결과, 물레나물에서는 hypericin이 확인되지 않은 반면, 고추나물의 꽃봉오리와 잎에서는 다량의 hyepricin이 확인되었다. 그리고 지리산에 자생하는 고추나물보다 병풍산 고추나물의 hypericin함량이 더 높게 나타났고, 고도가 낮을수록 hypericin 함량이 높은 것으로 나타났다. 채집 시기별로 비교했을 때, 병풍산은 6월보다 7월에서 hypericin함량이 높게 나타났고, 지리산에서는 7월에 가장 진하게 보였다. St. John's wort와 고추나물을 비교하였을 때, 2.22 $mg/{\ell}$ hypericin을 함유한 St. John's wort 보다 3.2 $mg/{\ell}$의 함량을 보이는 병풍산 고추나물에서 hypericin함량이 더 높은 것으로 확인되었다.

• Archives of Pharmacal Research
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• 제21권1호
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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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• 제25권2호
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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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• 제19권6호
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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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• 제9권2호
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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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• 제29권10호
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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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• 제25권8호
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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.

• 분석과학
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• 제8권4호
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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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• 제6권5호
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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.

• 생명과학회지
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• 제17권8호통권88호
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• pp.1034-1038
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• 2007

하이퍼리신(Hypericin, HyH)은 예로부터 성 요한의 풀(St. John's Wort)로 널리 알려져 있는 서양고추나물(Hypericum perforatum)에서 추출되는 약리성분이다. 서양고추나물은 국내에서는 자생하지 않으나 같은 속의 고추나물(H. erectum) 등이 이속에 속하며 우리나라에 자생한다 . 고추나물을 조직배양으로 RNA를 추출하고 cDNA를 합성한 후 Hyp 유전자를 추출하여 서열화한 결과, 전체 크기는 732 bp로 나타났으며 서양고추나물의 HyH-1과 거의 99.8% 서열 일치를 나타내었다. 이 서열의 152개 아미노산 역시 서양고추나물의 항산화효소와 98% 일치하였으며 자작나무와 능금속 식물에서 유발되는 알레르기 유발유전자와 약 60% 일치를 나타내었다. 본 연구 결과 우울증치료제로 사용되는 하이퍼리신 추출에 우리나라 자생종인 고추나물이 이용될 수 있을 것으로 사료된다.