• Korean Journal of Food Science and Technology
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• v.32 no.6
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• pp.1227-1233
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• 2000

Lycopene was subjected to ozonolysis in ice-cold dichloromethane. The ozonolysis products were fractionated with a silica column and the carbonyl fraction was analyzed by ODS-HPLC with a photodiode array detector and by LC-MS. UV-vis spectra and $[M+H]^+$ of the carbonyl compound peaks showed clearly that acycloretinal, apo-14'-lycopenal, apo-12'-lycopenal, apo-10'-lycopenal, apo-8'-lycopenal and apo-6'-lycopenal were formed by ozonolysis of lycopene. Lycopene was solubilized in toluene and aqueous Tween 40, and then oxidized by incubating at $37^{\circ}C$ under atmospheric oxygen. Carbonyl compounds were produced. In comparison with autoxidation and ozonolysis, each compound showed the same retention time and UV-vis spectra are identical to the reference cleavage products prepared by ozonolysis of lycopene. Thus, eccentric cleavage of lycopene was confirmed to occur in vitro under oxidation condition.

• Journal of the Korean Society of Food Science and Nutrition
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• v.26 no.6
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• pp.1122-1127
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• 1997

Melanoidins, which were higher polymers with intense brown color, were investigated on their decolorization and degradation by ozonolysis. Amino acids linked up with melanoidins were readily separated by depolymerization of melanoidins with ozonolysis. The IR spectra of ozone-untreated MRPs showed a higher peak at $1665cm^{-1}$ (C=N) and $1600cm^{-1}$ (C=C) than the corresponding peaks of ozone-treated MRPs. Ozone-treated melanoidins with molecular weight of above 900 showed the highest nitrogen composition of all melanoidins tested. Ozone-treated melanoidins with molecular weight of 900 to 1000 were separated into five peaks on recycling preparative HPLC chromatogram. Major functional groups in ozone-treated melanoidins with molecular weight of 900 to 1, 000 were -CH$_2$-CO-, -CH$_2$-O- and CH$_2$-.

• Korean Journal of Fisheries and Aquatic Sciences
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• v.19 no.1
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• pp.36-44
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• 1986

Nondialyzable melanoidins prepared from a glucose-glycine system were investigated as to their decolorization and degradation products on of one treatment. Melanoidins were decolorized to degree of $84\%\;and\;97%$ after ozonolysis at $-1^{\circ}C$ for 10 min and 90 min, respectively, and the mean molecular weight of melanoidins decreased from 7,000 to 3,000 after ozonolysis for 40 min. IR measurement showed that the absorption at $1,290\;cm^{-1}$ disappeared and that at $1,720\;cm^{-1}$ newly appeared on ozonolysis, and the absorption at $1,620\;cm^{-1}$ disappeared on acid hydrolysis after ozonolysis. Furthermore, the major degradation products in the ether-soluble fractions obtained from ozone-treated melanoidins were identified as butanedioic acid, glycolic acid, 2-hydroxybutanoic acid and so on. In the aqueous fraction, one or the major products was glycine, which was produced to the level of $1.05\%$ on ozonolysis which increased to $5.75\%$ per melanoidin on acid hydrolysis after ozonolysis. From these findings and the IR results, it is postulated that glycine was considerably incorporated into melanoidin molecules as the amide form.

• Korean Journal of Food Science and Technology
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• v.32 no.5
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• pp.985-990
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• 2000

${\zeta}-Carotene$ was subjected to ozonolysis in ice-cold dichloromethane. The ozonolysis products were fractionated with a silica column and the carbonyl fraction was analyzed by ODS-HPLC with a photodiode array detector. ${\zeta}-Carotene$ was solubilized in toluene, and then oxidized by incubating at $37^{\circ}C$, 72 hr under atmospheric oxygen. Carbonyl compound and acidic compound were produced. In comparison with autoxidation and ozonolysis, each compound showed the same retention time and UV-vis spectra were identical to the reference cleavage products prepared by ozonolysis of ${\zeta}-carotene$. Absorption spectrum of acidic compound was similar to that of standard 4,5-didehydrogeranyl geranyl acid which is known to possess biological activity. Thus, eccentric cleavage of ${\zeta}-carotene$ was confirmed to occur in vitro under oxidation condition.

• Bulletin of the Korean Chemical Society
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• v.23 no.3
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• pp.423-426
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• 2002

Treatment of conjugated cyclodienes (5a-5c) with excess ozone in dichoromethane in the presence of added carbonyl compounds (3) resulted to give the corresponding diozonides 10 and cross-ozonides 14. Similarly, ozonolysis of the nonconjugated 1,4-cyclohexadiene (6a) and 1,5-cyclooctadiene (6b) under same conditions afforded both diozonides 20 and cross-ozonides 14. On the other hand, Ozonolysis of bicyclo[2.2.0]hepta-2,5-diene (6c) in the presence of 3A provided the corresponding diozonide 19.

• Archives of Pharmacal Research
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• v.29 no.6
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• pp.464-468
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• 2006

Novel phenyl branched apiosyl nucleosides were synthesized in this study. The introduction of phenyl group in the 4'-position was accomplished by a [3,3]-sigmatropic rearrangement. Apiosyl sugar moiety was constructed by sequential ozonolysis and reductions. The natural bases (cytosine and adenine) were efficiently coupled with an apiosyl sugar by classical glycosyl condensation procedure (persilyated base and TMSOTf). The antiviral activities of the synthesized compounds were evaluated against the HIV-1, HSV-1, HSV-2 and HCMV.

• Bulletin of the Korean Chemical Society
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• v.19 no.11
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• pp.1244-1248
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• 1998

Ozonolysis reactions of cyclic olefins 1a-c and norbomene In in the presence of trifluoroactophenone 6 provided the corresponding cross-ozonides 7a-c and 7n. Further reactions of ozonides 7a-c and 7n with the independently prepared carbonyl oxide 11 gave diozonides of structure l0a-c and 10n. The ozonolysis of 1methylcyclopentene 12a and 1-methylcyclohexene 12b in the presence of trifluoroactophenone 6 provided exclusively ozonide 15 and 16 derived from capture of carbonyl oxide 13. All of the new ozonides have been isolated as pure substances and characterized by their 1H NMR and 13C NMR spectra.

• Bulletin of the Korean Chemical Society
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• v.21 no.4
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• pp.369-370
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• 2000

• Korean Journal of Food Science and Technology
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• v.30 no.3
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• pp.480-486
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• 1998

It was investigated that the reduction of the intense brown color and increase of solubility, and depolymerization of polymerized melanoidins by ozonolysis affect their antioxidative and antimutagenic activities. Melanoidins was depolymerized and decolorized by ozonolysis. Ozone-treated melanoidins revealed a lower antioxidative activity and a higher antimutagenic activity than those of the untreated control. Fractions of ozone-treated melanoidins showed three peaks resemble to that of the melanoidins on Sephadex column chromatogram. Melanoidins of above MW 1,200 showed intense brown color. However, the strongest electron-donating ability was detected in the melanoidins of between MW 750 to 900. Ozone-treated and ozone-untreated melanoidins of between MW 900 to 1,000 revealed the higher antioxidative and antimutagenic activities.

• Journal of the Korean Society of Food Science and Nutrition
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• v.29 no.4
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• pp.568-574
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• 2000

Phytofluene was subjected to ozonolysis in ice-cold dichloromethane. The ozonolysis products were fractionated with a silica column and the carbonyl fraction was analyzed by ODS-HPLC with a photodiode array detector. Phytofluene was solubilized in 5% tween 40, and then oxidized by incubating under dim yellow light at 37$^{\circ}C$, 24 hr with continuous shaking. Carbonyl compound and acidic compound were produced. In comparison with autoxidation and ozonolysis, each compound showed the same retention time and UV-vis spectra were identical to the reference cleavage products prepared by ozeonolysis of phytofluene. Absorption spectrum of acidic compound was similar to that of standard 4,5-didehydrogeranyl geranyl acid which is known to possess biological activity. Thus, eccentric cleavage of phytofluene was confirmed to occur in vitro under oxidation condition.