• Journal of Photoscience
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• v.11 no.32
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• pp.77-81
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• 2004

Deoxygadusol (DO) and structurally related mycosporine-like amino acids, i.e. mycosporine glycine (MO) and mycosporine taurine (MT), were isolated from phytoplankton Prorocentrum micans and studied for the reactivity toward singlet oxygen. These water-soluble compounds with a cyclohexenone chromophore were all shown to be highly effective in quenching singlet oxygen ($^1$ $O_2$), with the efficiencies being significantly larger compared with histidine, a well-known $^1$ $O_2$ quencher. The $^1$ $O_2$ reaction rate constant ( $k_{Q}$) of DG was determined to be 5.4 ${\times}$ 10$^{7}$ $M^{-1}$ $s^{-1}$ by a steady state method based on competitive inhibition of rubrene oxidation. The feasibility of this method was confirmed by estimating the $k_{Q}$ values for MG and two other quenchers, furfuryl alcohol and 1,4-diazabicyclo [2,2,2]octane, and comparing with those values determined by the time-resolved $^1$ $O_2$ decay method in the previous work.ork.

• Journal of Ginseng Research
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• v.13 no.1
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• pp.98-104
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• 1989

In order to determine the specific active oxygen species directly related to chlorophyll bleaching in the leaf-burning disease, we investigated the effects of singlet oxygen (1O2), superoxide radical (O2-), and hydrogen Peroxide (H2O2) on isolated chloroplast suspension and leaf discs from Panax ginseng C.A. Meyer. When the singlet oxygen was added to the chloroplast suspension, the chlorophyll and carotenoid contents were decreased by more than 809), similar to treatment with high light intensity (100 KLux). We assumed that the conversion of dioxygen (O2) produced either in photolysis or in breakdown of hydrogen peroxide to singlet oxygen resulted from photorespiration. On the basis of these experiments , :he inhibitory effects of active oxygen scavengers propylgallic acid (PGA), 2,5-ditetrabutyl hydroquinon (DBH), sodium pyrosulfate (SPS), and ascorbic acid (ABS) were examined. In chloroplast suspension all four scavengers inhibited chlorophyll bleaching by more than 75fl , and in the leaf discs the inhibition rates of SPS, PGA and ABS were 46%, 51%, and 96% respectively.

• Journal of Photoscience
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• v.9 no.2
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• pp.63-65
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• 2002

This report concerns a putative role of mycosporine-like amino acids (MAA) as natural scavengers of singlet oxygen ($^1$O$_2$) in marine organisms. MAA prepared from the ascidian Lissoclinum patella were found to protect biological systems against detrimental effects of the type II photosensitization in vitro. L. patella MAA were resolved into five components, and the relative $^1$0$_2$ quenching efficiencies were measured for three major components in aqueous media. It turned out that they were all effective in scavenging $^1$0$_2$, to different degrees albeit. The results suggest that physiological relevance of MAA in marine organisms may be found in a 'built-in' defense against photooxidative effects of sunlight.

• Biomaterials and Biomechanics in Bioengineering
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• v.1 no.2
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• pp.73-79
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• 2014

Covalent attachment of 1, 4-dimethylnaphthalene (DMN) based endoperoxide forming subunits to a polyvinyl butyral (PVB) backbone has been achieved. The functionalized polymer materials prepared and characterized here can serve as biocompatible carrier systems for studying cellular uptake, intermediate storage and delayed release of singlet oxygen, which opens up new doors for optimizing a variety of medical applications of photogenerated DMN-endoperoxides such as antiviral, antibacterial, antiplasmodial and antitumor activity.

• Journal of the Korean Chemical Society
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• v.23 no.6
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• pp.396-401
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• 1979

Measuring the reaction rate of bilirubin and oxodipyrromethenes with singlet oxygen, we have found oxodipyrromethenes to be better singlet oxygen trapping agents than diphenyl-isobenzofuran, the best such agent known so far. The photooxygenation rates of bilirubin and the model compounds, oxodipyrromethenes approached the diffusion control threshold. A new oxodipyrromethene is synthesized.

• Bulletin of the Korean Chemical Society
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• v.23 no.2
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• pp.281-285
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• 2002

The photophysical properties and the singlet oxygen generation efficiencies of meso-tetraphenyl-trithiasapphyrin $(S_3TPS)$ and meso-tetmkis(p-methoxy phenyl)-trithiasapphy rin ((p-MeO)-$S_3TPS$) have been investigated, utilizing steady-state and time-resolved spectroscopic methods to elucidate the possibility of their use as photosensitizers for photodynamic therapy (PDT). The observed photophysical properties were compared with those of other porphyrin-like photosensitizers in geometrical and electronic structural aspects, such as extended ${\pi}$ conjugation, structural distortion, and internal heavy atoms. The steady-state electronic absorption and fluorescence spectra were both red-shifted due to the extended ${\pi}$-conjugation. The fluorescence quantum yields were measured as very small. Even though intersystem crossing rates were expected to increase due to the increment of spin orbital coupling, the triplet quantum yields were measured as less than 0.15. Such characteristics can be ascribed to the more enhanced internal conversion rates compared with the intersystem crossing rates. Furthermore, the triplet state lifetimes were shortened to -1.0 ${\mu}s$ as expected. Therefore, the singlet oxygen quantum yields were estimated to be near zero due to the fast triplet state decay rates and the inefficient energy transfer to the oxygen molecule as well as the low triplet quantum yields. The low efficiencies of energy transfer to the oxygen molecule can be attributed to the lower oxidation potential and/or the energetically low lying triplet state. Such photophysical factors should be carefully evaluated as potential photosensitizers that have extended ${\pi}$-conjugation and heavy core atoms synthesized for red-shifted absorption and high triplet state quantum yields.

• Food Science and Biotechnology
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• v.18 no.2
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• pp.526-532
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• 2009

Quenching mechanisms and kinetics of $\alpha$-, $\beta$-, $\gamma$-, and $\delta$-tocopherol in photosensitized oxidation of lard were studied. Lard at 0.03, 0.07, 0.11, and 0.3 M in methylene chloride containing $4.4{\times}10^{-6}\;M$ chlorophyll and 0, 0.1, 0.3, and 0.6 mM $\alpha$-, $\beta$-, $\gamma$-, and $\delta$-tocopherol were stored under light for 4 hr, respectively. Oxidation was determined by headspace oxygen and peroxide value. Tocopherols prevented the photosensitized oxidation of lard (p<0.05). Steady state kinetic study showed that $\alpha$-, $\beta$-, $\gamma$-, and $\delta$-tocopherol prevented the photosensitized oxidation of lard by quenching singlet oxygen. Singlet oxygen quenching rates of $\alpha$-, $\beta$-, $\gamma$-, and $\delta$-tocopherol by headspace oxygen depletion were 1.86, 2.39, 2.47, and $2.11{\times}10^7/M/sec$, respectively. The quenching rates of $\alpha$-, $\beta$-, $\gamma$-, and $\delta$-tocopherol by peroxide value were 1.42, 1.11, 0.97, and $0.42{\times}10^7/M/sec$, respectively. The quenching rates of tocopherols were slightly different depending on the measurements of oxidation.

• Journal of Photoscience
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• v.9 no.2
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• pp.174-177
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• 2002

Sugar-linked porphyrin and chlorin compounds have been synthesized. Phototoxicity of these compounds against the HeLa cell line was also examined. For the porphyrin derivatives, the higher activity was observed for a derivative having four OH-protected sugar moieties. For the chlorin derivatives, OH-unprotected free-base derivatives were generally effective. Singlet oxygen producing ability were examined to evaluate the activity on photodynamic therapy of the compounds.

• Korean Journal of Food Science and Technology
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• v.33 no.1
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• pp.1-6
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• 2001

Emulsion products with water soluble protein were exposed under light at $5^{\circ}C$ for 8 days. Peroxide value (POV) was increased significantly at the bigining of storage and 2-thiobarbituric acid (TBA) value also increased until 4 days of storage with increase of the production of carbonyl compounds, suggesting that the condition was reacted different from that of the lipid autoxidation. The reaction was similar to the flavor reversion that usually produced from the bigining of soybean oil oxidation. The reason might be the meat pigment, myoglobin, oxidation and it would be due to the singlet oxygen rather than superoxide anion. When the light was excluded general pattern was similar but the production of oxidation products were smaller than that when the sample was exposed under light. The effect of the singlet oxygen was also smaller which meant that the singlet oxygen produced during emulsion process may affect on the flavor reversion at the bigining of storage. The POV of the emulsion without water soluble protein increase gradually by storage and the results indicated that the degradation rate of the peroxides were lower than the sample with water soluble protein. Especially after 4 days of storage, production of carbonyl compounds were decreased. During storage it would be possible to produce the singlet oxygen and the sensitizer from the plants that can be produced during decoloration of soybean oil may be responsible for it. When the light was excluded the production of oxidation products were reduced at the begining of storage and the effect of quencher also was not detected. Therefore the results indicated that the light can accelerate the lipid oxidation.

• Proceedings of the Korean Society of Near Infrared Spectroscopy Conference
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• 2001.06a
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• pp.3102-3102
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• 2001

Constituents of several .representative seaweeds, such as wakame Undaria pinnatifida; hijikia Hizikia fusifome; and kombu Laminaria japonica, were found to have fairly large reaction rates determined by quenching experiments of emission spectra in the near-infrared region (1max: 1270 nm) from singlet oxygen (102). Emission spectra of singlet oxygen generated from an aqueous solution of Rose Bengal under irradiation with a green laser (330 nm) were measured by a near-infrared (NIR) emission spectrometer constructed in our laboratory. The quenching experiments were as follows: Intensities of emission spectra were measured in the absence (I0) and in the presence of the seaweed constituents (I): Ratios of I0/I were plotted against every concentration of the quenchers (Stern-Volmer plots) which gives a straight line. The slope of each line gives a kqt value which gives a quenching constant kq value (an antioxidative constant against singlet oxygen) when the t value (half-life time of singlet oxygen in the solvent used) was given. The determined reaction rates are between 103-105 (g/l)-ls-1; the larger ones are as large as that of ascorbic acid, 8.4 ${\times}$ 104 (g/1)-ls-1. Most of these seaweed constituents also showed antioxidative activity against auto-oxidation and superoxide as well as their immunological enhancing activity. These results suggest a possibility that dietary fibers which are supposed to prevent the large-intestine cancer by their physical properties may prevent the cancer, at least in parts, by their chemical, antioxidative activity.