• Title/Summary/Keyword: psoralen

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Ab Initio Study on the Psoralen(I)

  • Kim, Ja-Hong;Kwon, O-Hyung
    • Journal of Photoscience
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    • v.12 no.3
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    • pp.185-186
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    • 2005
  • The electronic structure of photoskinsensitizing psoralens has been investigated by the ab initio calculations. The photocycloaddition reaction of 8-methoxypsoralen with thymine is studied as a model for the photosensitizing reaction of psoralen with DNA bases. The photocycloadduct was inferred to be a C4-cycloaddition product with the stereochemistry of Syn, H-H, Syn, H-T formed through [2+2] addition reaction between the 3,4-double bonds of 8-methoxypsoralen and 5,6-double bond of thymine base.

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Photocyclodimerization of Maleimide

  • Shim, Sang-Chul;Bong, Pill-Hoon
    • Bulletin of the Korean Chemical Society
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    • v.3 no.3
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    • pp.115-119
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    • 1982
  • The photoreaction of maleimide, one of the best model compounds of DNA molecules for psoralen-DNA photoreactions, is studied in order to investigate the photoreactivity and the mechanism of the maleimide-psoralen photoreaction. The (2+2) photocyclodimer of maleimide was obtained in solution state by direct or sensitized irradiation. The rate constant of dimerization is determined by quenching studies and found to be of the order of $10^9 M^{-1}sec^{-1}$. The direct dimerization of maleimide is found to undergo through the triplet excited state. The quantum yields of dimerization are dependent on the maleimide concentration.

PHOTOCHEMISTRY AND PHOTOBIOLOGY OF PSORALENS

  • Shim, Sang-Chul;Jeon, Young Hee;Kim, DongWon;Han, GyuSeok;Yoo, Dong Jin
    • Journal of Photoscience
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    • v.2 no.1
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    • pp.37-45
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    • 1995
  • INTRODUCTION : Psoralens are planar tricyclic furocoumarins present in numerous plants and fungi found throughout the world.' Naturally occurring and synthesized psoralen derivatives(see Figure 1) are photosensitizers of UVA especially from 320 nm to 400 nm, a range at which cellular nucleic acids and proteins are weakly absorbing if any at all. Because of their skinphotosensitizing properties, these compounds have been used in the photochemotherapy of psoriasis and vitiligo. However, undesirable side effects such as carcinoma development in hairless mice as well as possible liver damage from the use of 8-methoxypsoralen(8-MOP) have been reported. The other photobiological effects include inactivation of DNA viruses, killing and mutagenesis of bacteria, inhibition of tumor transmitting capacity of various cells, and hyperpigmentation on human and guinea pig skin. PUVA(psoralen+UVA) photochemotherapy is in fact thousands of years old, having been used in Egypt and India since B.C. 1200-2000. Photochemotherapy for a common disfiguring disease, vitiligo, was practiced in the ancient world by physicians and herbalists who used boiled extracts of the fruits of certain umbelliferous plants, e.g. Ammi majus Linnaeus in Egypt or the leguminous plants, Psoralea corylifolia L. in India. It was first described by Kuske in 19388 that photosensitization of skin by plants was related to the presence of psoralen. He identified natural psoralens in plants as photosensitizers and isolated bergapten(5methoxypsoralen) from the oil of bergamot. The scientific interest in photosensitizing psoralens, however, has grown considerably after the introduction into clinics of the psoralen photochemotherapy for the treatment of psoriasis and of other skin (abbreviation)

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Theoretical Studies on the Photochemical Reaction of Psoralen Derivatives (Ⅲ) Photoadducts of Methylpsoralen and Hydroxypsoralen with Thymine (소랄렌 유도체의 광화학 반응에 관한 이론적 연구 (Ⅲ) 메칠소랄렌 및 하이드록시소랄렌과 티민의 광생성물의 구조)

  • Kim, Ja Hong;Son, Seong Ho;Yang, Gi Su;Park, Byeong Seo
    • Journal of the Korean Chemical Society
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    • v.38 no.6
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    • pp.405-410
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    • 1994
  • Molecular orbital calculations suggest that an interaction between the psoralen derivatives of excite state and the thymine of ground state is dicussed in terms of their differing abilities to molecular complex. PM3-CI-UHF indicates that photocycloadducts across the C3-C4 and C4'-C5' double bonds of the methylpsoralen and hydroxypsoralen with thymine C5-C6 double bonds were deduced to be formed by their preferable frontier orbital interactions. The electronic properties of psoralen derivatives in the ground and excited states correlate with this difference in structure-activity relationship.

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Theoretical Studies on the Photochemical Reaction of Psoralen(I) Structure-Activity Studies on the Psoralen (소랄렌의 광화학 반응에 대한 이론적 연구 (I) 소랄렌의 구조-활성화에 대하여)

  • Ja Hong Kim;Gil Young Chung;Sung Ho Sohn;Kee Soo Yang
    • Journal of the Korean Chemical Society
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    • v.37 no.4
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    • pp.396-400
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    • 1993
  • The structure-activity relationship of photo-skinsensitizing psoralens has been investigated by the MM2, FMO, molecular connectivity methods. The molecular complexes between DNA and photoskinsensitizing psoralens are discussed in terms of their differing abilities to complex and react with psoralen interstrand cross linking DNA base. The photoskinsensitiziers are analyzed with respect to the sterographics models of the active sites of the psoralens and frontier orbital density is closely correlated with photo-skinsensitizing carcinogenic activity.

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Photoinhibition of Candida Albicans Growth by Psoralen Derivatives

  • Han, Gyu-Seok;Shim, Sang-Chul;Hann, Seung-Kyung;Jang, Nam-Su;Wee, Seong-Ho;Park, Yoon-Kee
    • Journal of Photoscience
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    • v.5 no.4
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    • pp.163-167
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    • 1998
  • Candida albcans growth inhibition experiments were carried out to determine the photoxicity of new monofunctional psoralen derivatives, PzPs and HMPzPs, as well as well known 8-MOP an d5-MOP. Although 8-MOP and 5-MOP showed distince photoxicity, PzPs and HMPzPs did not inhibit the growth of Candida albicans strain indicating that PzPs derivatives were not good candidate for the treatment of psoriasis. However, vitili해 could be treated by PzPs derivatives without severe phototosicity because psoralens are known to treat vitiligo by stimulating melanogenesis on skin.

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The Chemical Constituents from Heracleum moellendorffii Roots (어수리의 성분)

  • Kwon, Yong-Soo;Cho, He-Young;Kim, Chang-Min
    • YAKHAK HOEJI
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    • v.44 no.6
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    • pp.521-527
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    • 2000
  • The root of Heracleum moellendorffii was extracted with methanol and extract was fractionated with n-hexane, $CHCI_3$ and n-BuOH. Repaeated column chromatography of silica gel, sephadex LH 20 and ODS led to the isolation of ten compounds from n-hexane fraction and n-BuOH fraction. On the basis of spectroscopic evidences, the structures of isolated compounds were identified as isobergapten, psoralen, angelicin, sphondin, xanthotoxin, skimmin, cichoriin, $heratomol-6-O-{\beta}-D-glucopyranoside$, scopolin and apterin.

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Protesome Inhibition Activity of Psoraleae Semen and Processed Psoraleae Semen (보골지 및 염초보골지의 proteasome 저해 작용)

  • Shim, Sang-Hee
    • Korean Journal of Pharmacognosy
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    • v.39 no.1
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    • pp.56-59
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    • 2008
  • Ubiquitin-proteasome proteolytic system plays an important role in selective protein degradation and regulates cellular events including apoptosis. Cancer cells have been shown to be more sensitive to the proapoptotic effects of proteasome inhibition than normal cells. Thus, proteasome inhibitor can be potential anticancer agent. Since the MeOH extracts of psoraleae semen and processed psoraleae semen showed potent proteasome inhibition activity, the fractions of the extracts were evaluated on the activity to screen the proteasome inhibitors. The $CHCl_3$ fr. of the processed psoraleae semen showed the most potent activity, of which chemical investigation led to two coumarins, psoralen and isopsoralen. Their structures were determined by spectroscopic methods such as $^1H-NMR$ and EIMS spectra.

Isolation and Structure Determination of Coumarin Derivatives from the Roots of Angelica dahurica

  • Kim, Ji-Yeon;Son, Jong-Keun;Song, Dong-Keun
    • Journal of Evidence-Based Herbal Medicine
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    • v.3 no.1
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    • pp.35-41
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    • 2010
  • From the roots of Angelica dahurica Bentham et Hooker (Umbelliferae), three known coumarin derivatives have been isolated and identified as 8-(2-hydroxy-3-methoxy-3-methylbutyloxy) psoralen, 5,8-di(2,3-dihydroxy-3-methylbutyloxy) psoralen, 9-[3-($\beta$-D-glucopyranosyloxy)-2-hydroxy-3-methylbutoxy]-7H-furo[3,2-g][1]benzopyran-7-one. This is the first report of the occurrence of these compounds in this plant. These three compounds were tested for activity in septic shock model. Among these compounds, 2 showed relatively strong preventive activity against septic shock.

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