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Marine Toxin Research in Japan

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Marine Toxin Research in Japan Discovery of novel ovatoxin isomers in several Ostreopsis strains in Japan Toshiyuki Suzukia, Ryuichi Watanabea, Hajime Uchidaa,b,Ryoji Matsushimaa, Hiroshi Nagaib, Takeshi Yasumotoa, Takamichi Yoshimatsue, Shinya Satoc,d, Masao Adachie a National Research Institute of Fisheries Science, 2-12-4 Fukuura, Kanazawa, Yokohama, Kanagawa 236-8648, Japan. b Tokyo University of Marine Science and Technology, 4-5-7, Konan, Minato-ku, Tokyo, 108-8477, Japan. c Royal Botanic Garden Edinburgh, 20 Inverleith Row, EH3 5LR Edinburgh, UK d Institute of Molecular Plant Sciences, School of Biological Sciences, University of Edinburgh, EH9 3JH Edinburgh, UK e Kochi University, 200 Otsu, Monobe, Nankoku, 783-8502 Kochi, Japan Ostreopsis spp. • The dinoflagellate genus, Ostreopsis, has an increasingly global distribution • Some Ostreopsis produces palytoxin analogues • O. ovata is held responsible for respiratory illnesses due to inhalation of aerosols during blooms in the Mediterranean region Dinoflagellate genus Ostreopsis spp. （O.siamensis O. ovata etc 9 species） (Rhodes et al, Toxicon 2010) Ostreopsis found along the coastal area in Japan Palytoxins OH HO OH O O HO OH Ostreopsis OH The Soft coral O OH HO OH Palythoa toxica O HO OH OH OH OH H N 2 B moiety OH A moiety OH HO OH O OOR1 OH HO OH 8 OH OH HO N N 3 9 O H H H OH OH OH HO HO OH O R2 O O R OH HO 3 R OH 4 OH O OH HO OH OH R1 R2 R3 R4 R5 R5 OH OH Palytoxin Me OH Me HOH Ostreocin-D HHHOHH Human poisoning cases due to consumption of seafood suspected to be contaminated with palytoxins • Human fatalities due to consumption of seafood suspected to be contaminated with palytoxins were reported in the Philippines, after consumption of the crab Demania reynaudii (1988), and in Madagascar following consumption of the sardine Herklotsichthys quadrimaculatus (clupeotoxism) (1999) • Respiratory illness has also occurred when people were exposed to Ostreopsis ovata bloom aerosols during recreational or working activities, in Italy (2006) D. reynaudii H. quadrimaculatus Ostreopsis ovata Blue humphead parrotfish (Scarus ovifrons) poisoning in Japan (Palytoxin like poisoning) • Symptoms: Rhabdomyolysis, a syndrome injuring skeletal muscle, causing muscle breakdown, and leakage of large quantities of intracellular (myocyte) contents into blood plasma • The symptoms are similar to palytoxin poisoning • Palytoxins have not been confirmed yet from the blue humphed parrotfish which was identified as the causative food in the poisoning cases ? palytoxin Ostreopsis ? Scarus ovifrons The Soft coral Palythoa spp. Blue humphead parrotfish (Scarus ovifrons) poisoning in Japan (Palytoxin like poisoning) 9 patients in 2007 3 patients in 2004 × ××× ×× × 2 patients 2 patients ×× in 2001 in 2004 1 people 11 patients died 3 patients in 2003 in 2000 In 2011 4 patients were reported in Tokyo in November 1 patient was reported in Miyazaki in March Objectives • LC-MS/MS analysis of palytoxin analogues in several Ostreopsis strains collected in Japan • LC-MS/MS analysis of palytoxin analogues in the blue humphead parrotfish (Scarus ovifrons) which was identified as the causative food in human poisoning cases in Tokyo and Miyazaki in 2011 LC-MS/MS analysis of palytoxin analogues in several Ostreopsis strains collected in Japan References • Ciminiello, P. et al. 2006. The Genoa 2005 outbreak. Determination of putative palytoxin in Mediterranean Ostreopsis ovata by a new liquid chromatography tandem mass spectrometry method. Anal. Chem. 78, 6153–6159. • Ciminiello, P. et al. 2008. Putative palytoxin and its new analogue, ovatoxin-a, in Ostreopsis ovata collected along the Ligurian coasts during the 2006 toxic outbreak. J. Am. Soc. Mass Spectrom. 19, 111– 120. • Ciminiello, P. et al. 2010. Complex palytoxin-like profile of Ostreopsis ovata. Identification of four new ovatoxins by high-resolution liquid chromatography/mass spectrometry. Rapid commun. Mass Spectrom. 24, 2735–2744. LC-MS/MS chromatogram of palytoxin LC-MS condition Column: Hypersil-BDS-C8 (10 ng) (150 mm x 2 mm i.d) Palytoxin Flow rate: 0.2 mL/min OH HO OH O O HO OH Mobile phase: A water, B 95% MeCN OH O OH HO OH both containing 2 mM HCOONH and 50 O 4 HO OH OH OH OH mM HCOOH H N 2 B moiety OH A moiety OH HO OH O OOR1 OH HO OH 8 OH OH HO N N 3 9 O H H H Step 1: 5 % B 100%B for 15 min OH OH OH HO HO m/z 327 OH Step 2: 100 % B for 5 min O R2 O O R OH HO 3 R OH 4 OH O OH HO OH OH R1 R2 R3 R4 R5 R5 OH Detection OH 2- Palytoxin Me OH Me HOH [M+2H-H2 O] 1331> 327 Ostreocin-D HHHOHH LOD：10ng/ml (0.1ng) m/z1331> 327 0 5 10 15 20 Time (min) LC-MS/MS chromatogram of palytoxin analogues in Ostreopsis collected in coastal waters in Japan Peak #1: Ovatoxin-a Ostreopsis culture 1 Peak #2: Ovatoxin-b Peak #3: Ovatoxin-b isotope Cells were harvested by Peak #4: Ovatoxin-d centrifugation at 3000 rpm Peak #5: Ovatoxin-a isotope Peak #6: Ovatoxin-e Toxins were extracted with MeOH Peak #7: Palytoxin An aliquot of the MeOH extract was analyzed by LC-MS/MS 7 4 5 6 m/z1331>327 (x10) m/z1323>343 m/z 1323>327 2 m/z 1345>371 (x10) 3 m/z 1337>371 (x10) m/z 1315>327 0 5 10 15 20 LC-MS/MS chromatogram obtained from the mixture of Italian and Japanese Ostreopsis strain extracts Ovatoxin-e AC from Japanese culture (A) (D) Ovatoxin-e2 Ovatoxin-a2Ovatoxin-a AC from Japanese culture Ovatoxin-a Ovatoxin-e m/z 1315>327 m/z 1323>343 10 11 12 13 14 15 10 11 12 13 14 15 Time (min) Time (min) AC: Porf. Adachi Culture 726.4040 786.4253 726.4065 744.4170 (-3.5 ppm) C 786.4276 (-3.0 ppm) -H2O -H2O OH HO OH 804.4382 O O HO 80 OH OH O OH HO OH 78 O HO OH 327.1935 OH OH OH (+4.5 ppm) -H O H N 2 +2H 2 OH 327.1920 (345.2026) OH HO OH O OOOH HO OH 9 OH OH HO N N O H H 8 H OH OH OH HO HO B OH A O OH O O OH HO OH 309 OH O OH [M+2H-nH O]2- HO OH OH 2 327 HO OH OH 1277 1268 744 406 726 804 377 419 786 300 400 500 600 700 800 900 1000 1100 1200 1300 1400 m/z LC-MS/MS spectra of palytoxin analogues in Ostreopsis Palytoxin Ostreocin-D A A-CH 2 2- 2- 295 309 [M+2H-nH2O] [M+2H-nH2O] 327 1277 1282 C 313 C 1268 1273 744 744 406 804 406 388 726 726 804 786 377 419 786 363 300 400 500 600 700 800 900 1000 1100 1200 1300 300 400 500 600 700 800 900 1000 1100 1200 1300 m/z m/z Ovatoxin-a AC Ovatoxin-b A 353 A +2CH +O 2- 2 309 [M+2H-nH2O] 327 371 C 1288 2- C [M+2H-nH2O] 744 1279 401 335 377 1310 726 804 726 744 445 804 406 1301 419 786 463 708 786 300 400 500 600 700 800 900 1000 1100 1200 1300 300 400 500 600 700 800 900 1000 1100 1200 1300 m/z m/z authentic palytoxin standard by Qtof LC-MS/MS authentic palytoxinstandard byQtof High-resolution LC-MS/MS productionspectraobtainedfor 216.1024 234.1132 252.1233 327.1907 377.2084 406.2214 419.2178 542.2970 726.4079 744.4179 786.4265 804.4369 1013.6194 1057.6464 1075.6543 m/z * 1388.7583 1416.7519 1496.7788 1514.7936 2281.2503 Ovatoxin-a ACbyQtof LC-MS/MS High-resolution LC-MS/MS productionspectraobtainedfor 216.1019 234.1130 252.1231 327.1913 377.2072 406.2218 419.2167 542.2967 726.4047 744.4158 786.4308 804.4359 997.6144 m/z * 1372.7596 1400.7532 2249.2609 Proposed fragmentation diagram of palytoxin -H2O -H2O 252.12 234.11 216.10 OO 726.41 744.42 786.43 -H2O -H2O HO N N OH H H HO OH 2 OH OH 804.44 O O HO OH OH m/z 327; C H N O HO O OH 78 16 27 2 5 OH (560) +H -H2O O HO (460) 542.30 OH -3H2O OH 419.22 73 OH 115 406.22 OH -3H O +2H H2N 2 -H2O (2335) 2281.26 -4H2O OH OH 2249.27 327.19 (345) (491) HO OH O OOOH HO +H OH 9 16 OH OH HO N N 1 8 O 1400.75 H H H OH OH +H OH 1416.75 HO HO 377.21 431.23 -2H O -3H O 20 2 OH 2 OH O O (1452) O OH HO 997.62 -2H2O OH 1013.62 (1049) 42 OH O 49 50 53 41 OH HO OH OH HO OH -2H O+2H 1057.65 1075.65 (1093) OH 2 (1422) 1388.75 -H2O -H2O +H -4H2O+H -H2O (1585) 1514.79 1496.78 1372.76 Elemental formulae of palytoxin analogues determined by QTOF LC-MS spectra on the positive mode m/z Formula Tolerance (measured (ppm) value) Ovatoxin-a AC 2647.5062 C129 H224 N3O 52 3.2 Ovatoxin-d AC 2663.4918 C129 H224 N3O 53 -0.3 Ovatoxin-e AC 2663.4841 C129 H224 N3O 53 -3.2 Clades classified by the phylogenetic analysis reported in our previous study (Sato et al., 2011) 100% collected inJapanand Italy(*1)analyzedbyMRMLC-MS/MS Toxin profilesofseveral 20% 40% 60% 80% 0% s0743 (A) s0752 (A) KAC85 (Italy) (A) *1 s0662 (A) s0758 (A) s0788 (A) s0579 (A-2) s0772 (B) T80624-6 (B) Ostreopsis WK27 ( B) WK51 ( B) Ostreopsis s0618 (B) strains s0737 (B) HF66 (B) CT4 (B) KM5 (B) strains s0716 (B) MB80828-3 (B) s0577 (C-1) O07421-2 (C-2) s0806 (C-3) IR33 (D-1) OU11 (D-1) s0587 (D-2) palytoxin AC ovatoxin-a AC ovatoxin-b ovatoxin-c AC AC ovatoxin-d ovatoxin-e AC ostreocin-d pg collected inJapanand Italy(*1)analyzedbyMRMLC-MS/MS Total cellulartoxincontents ofseveral 10 12 14 16 0 2 4 6 8 s0743 (A) s0752 (A) KAC85 (Italy) (A) *1 s0662 (A) s0758 (A) s0788 (A) s0579 (A-2) s0772 (B) T80624-6 (B) Ostreopsis WK27 (B) WK51 (B) s0618 (B) strains s0737 (B) HF66 (B) CT4 (B) KM5 (B) s0716 (B) Ostreopsis MB80828-3 (B) s0577 (C-1) O07421-2 (C-2) s0806 (C-3) IR33 (D-1) OU11 (D-1) strains s0587 (D-2) Summary • Novel isomers of ovatoxin-a, -b, -d, -e were found in Japanese Ostreopsis.
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