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2 chemical studies on peroxynitrite (an active nitrogen species) scavenging by carotenoids Educational Division of Science and Technofogy Major in Bioscience Shizuoka University January 2011
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6 Xantho phyll Astaxa nth in Zeaxant h i n Violaxa nthin Capsanthin Fu coxa nth in Canth axanthin Garotene Lycopene F-Ca rote n e oc-ca rote n e Fig. 1. Structures of Some Carotenoids.
7 Table 1. Singlet Oxygen Quenching Abilities of Carotenoids and Related Compounds. compound Lycopene u-carotene Astaxanthin Canthaxanthin cr-carotene F-Carotene Bixin Zeaxanthin Lutein Cryptoxanthin Bilirubin Biliverdin Bilirubin ditaurate Crocin cr-tocopherol B-Tocopherol Cysteine u-tocopherol 6-Tocopherol Lipoate Coen4yme A Glutathione Dihydrolipoate kn: singlet oxygen quenching constant.
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16 Cr ohgs a.tocopherol CroHss tooopheroxyl cation c-tooopheroquinone Fig. 2. Two-Electron Oxidation of q-tocopherol by Peroxynitrite to Form q-tocopheroqu inone.
17 OMe Methorylycopene Apo-lycopena I Fig.3. Peroxynitrite Reaction Pathway with by Yokota et al. Lycopene Reported
18 Table 2. Research of Carotenoids and Peroxynitrite. Kikugawa b f -carotene Koppenol b Zeaxantfiin Pannala b Lycopene B -carotene Scheidegger b Zeaxantiin Lycopene Maoka b Garotenoids Paorika f -carotene f -carotene Astaxanthin Hnyakawa6* Astaxanthin
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20 Fig. 4. Estimated Nitration Mechanism of Peroxynitrite Scavenging by Carotenoids.
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23 Capsanthin Fucoxanthin Fig. 5. Asymmetric Structures of Lutein, Capsanthin and Fucoxanthin.
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25 15 t4'
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27 +ToVacuum Fig. 6. Formation of Peroxyn itrite
28 Retentiontime (min) cof umn: Develosil c30-uc x250 mm, Flow late: 1 ml/min, Mobif e phase: MeCN: H20 = 90:10, Detector: 447 nm Ftg.7. HPLC analysis of Peroxynitrite Reaction Products with Lutein. Fraction
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30 Fig. 9. Structures of Nitrolutein.
31 Organic layer Aq ueous layer dried o\er anhydrous NarSOo concd. Scheme 1. Procedure for Reaction of Lutein with Peroxynitrite and Seperation.
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34 e6 Fig. 10. Structures Lutein Oxazine (3) and
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40 Nitro-lutein cis doublebond trans doublebond s-cis cis trans 1 4-s-cis- 1 5-N itrolutein k J/mol trans cis s-cis kJ/mol trans cis trans kJ/mol s-cls cis trans kJ/mol s-cis trans trans kJ/mol trans trans s-cis kJ/mol
41 Fig. 12. Peroxynitrite Reaction Pathway with Lutein.Energetically stable inte rmediate substa nce
42 cis doublebond trans doublebond trans cis trans k J/mol trans cis s-cis k J/mol trans cis trans kJ/mol s-cis cis trans kJ/mol trans trans s-cis kJ/mol trans trans trans kJ /mol trans trans s-cis kJ/mol
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46 1 2-Nitrocapsanth in (5) Fig. 13. Structures of Nitrocapsanthin.
47 Alltra ns-capsanth in 2 0 mg Organic layer Aqueous layer d ried over an hyd rous NarSOo concd. Scheme 2. Procedure for Reaction of Capsanthin with Peroxynitrite and Separation.
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49 1 4'-s-cis- 1 5'-N itrocapsanthin (4) HOI.ooYoo - 1.7s 1 2-Nitrocapsanthin (5)
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51 s-trans 18.6, s.sz 1 2-N itrocapsanth in (5)
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53 1 4-cls-15-N itrofucoxanthi n (6 ) Fig" 15. Structures of Nitrofucoxanthin.
54 All-tra ns-fucoxanthin 68.4 mg dissolved in THF 6.84 ml added TFA 96 tt I added 50 mm peroxynitrite 965 reacted for 1 min. added HrO 30 ml added CHCI,30 ml Organic layer Aqueous layer dried o\er anhydrous NarSOo corcd. HPLC analysis I seperated by HPLC (Develosil C30-UG-5 O20 x 250 mm MeCN:HrO=80:20) Fr.A.B ll Fr.C I seperated by HPLC (Develosil C30-UG-5 O20 x25o mm MeCN:HrO=80:20) I NMR MS Scheme 3. Procedure for Reaction of Fucoxanthin with Peroxynitrite and Separation. 50
55 All- tra ns-fu coxa n t h in Fig. 16. HPLC Analysis of Peroxynltrite Reaction Products with Fucoxanthin.
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57 11+is-l1-Nitrofucoxanthin (7) /FO
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59 s-trans s-c/s s-trans s-crb t5.s4/ : o lo 1 1 -crb-l 1 -N itrofucoxanthin (7 )
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65 7 = ++i vf Y/c*w,+l+ Pump: JASC0 PU Line degasser: JASCO DG Column oven: JASCO C0-965 Detector: JASC0 UV-970 Column: Develosil C3Q-UG-$ 6 20x250 mm Mobile phase: MeCN: H20 = 90:10 Flow rate: 10 m1lmin Temp : 32"C Detector:450nm
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78 : o \Fo 1 4-s-cis-l S-Nitrofucoxa nth in (6) 1 1 -cfs-l 1 -Nitrofucoxanthin (7)
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Title 数種の中国産甘草サポニン成分の化学的研究 Author(s) 堀, 一之 Citation Issue Date Text Version ETD URL https://doi.org/10.11501/3070540 DOI 10.11501/3070540 rights 0 0 II C 0 COOR COOK OH HOH COOR 0 OH HOO H H3 16
CHEMOTHERAPY APR Fig. 1 Chemical structure of cefotetan (CTT, YM09330)
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79 +.* + 1/* A + 80, E + + Bioaccessibility +, 81,. 0* nm bo, Caco-, +* - - 82 - Caco, + Pow +, b-carotene ;,, a-carotene ; -, b-cryptoxanthin ;., lutein ; /, zeaxanthin ; 0, canthaxanthin ; 1, astaxanthin
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th 37 ICh Theoretical Examination - - - - 5 - - : - ( ): ( ) - : 279 - - - - - - - G D L U C K 1 2 1 amu = 1.6605 10-27 kg N = 6.02 10 23 mol -1 k = 1.3806503 10-23 J K -1 e = 1.6022 10-19 C F = 9.6485
Isitobi et al. 1989 1990 3m 4.5 5.5m 3 1990 0.5 1 Notomastus sp. 4m 1983 6 4 7 11 5 2.5 1.0 4 7.5 3 5 1968 1991 1987 1990 Seike et al. 1990 1977a 1977
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26 3 31 BDF BDF BDF FAME BDF BDF BDF BDF BDF BDF BDF BDF BDF FAME BDF BDF 80.0 97.0% BDF 120 330 0.8% 2.2% 1. 1 1-1 1 1-2 1 2. 2 2-1 2 2-2 5 2-3 6 3. BDF 7 3-1 7 3-2 7 3-3 14 3-4 JOY 21 3-5 32 3-6 39 3-7
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(1) / 130 g 25 g 520% 170 g 30 g 560% 70 mg 600 mg 11.6% 0 10.5 mg 0% (1) (2) / 50100 g 25 g 200400% 50100 g 30 g 167333% 5001000 mg 600 mg 83167% 1020 mg 10.5 mg 95190% (2) / (1) 45.6 g 30 g 152% (2)