697:(PKC) is likely to be responsible for the antiproliferative and tumor-promoting activities of aplysiatoxin-related compounds. Tumor promoters like PDBu and ATX bound potently to the C1 domains of both conventional and novel PKCs, while antiproliferative compounds such as aplog-1 and bryo-1 exhibited some selectivity for novel PKCs other than PKCε, that is, PKCδ, PKCη, and PKCθ. The affinity of DAT for the PKC C1 domains is quite similar to that of aplysiatoxin. The introduction of a methylgroup group into position 4 could enhance the affinity for conventional PKCs rather than for novel PKCs, and the introduction of a methyl group into position 10 would enhance the affinity for both conventional and novel PKCs. Activation of
225:
723:
moiety of aplog-1 would enhance antiproliferative activities but not tumor-promoting activity. The antiproliferative activities of the analogs to not simply depend on molecular hydrophobicity, and the local hydrophobicity around position 10 plays an important role in enhancing antiproliferative activities. Because the analogues possess the skeleton of tumor-promoting aplysiatoxin and debromoaplysiatoxin, the adverse effects would be most likely tumor promotion.
24:
1395:
114:
722:
groups at position 6 are indispensable to these activities, but that the hydroxyl group at position 18 is not necessary. Of note, the more hydrophobic 12,12-dimethyl-aplog-1 did not show any tumor-promoting activity in vitro or in vivo. These results suggest that hydrophobicity around the spiroketal
824:
In the aplysiatoxin class, debromoaplysiatoxin, aplysiatoxin, and 19-bromoaplysiatoxin have been found to be tumor promoters in mouse skin. Also rat tracheal cells in culture are sensitive indicators for the presence of the polyacetates, aplysiatoxin and debromoaplysiatoxin. It causes increase in
713:
Aplog-1, a simple and less hydrophobic analog of aplysiatoxin, is a PKC ligand with little tumor-promoting activity that showed growth-inhibitory activities against several cancer cell lines. Multiple derivatives were evaluated for their antiproliferative activity against several human cancer cell
494:
The first reported case of seaweed dermatitis was from 1958 in Hawaii on Oahu island. About 125 people who had been swimming in the sea get suffered from symptoms like itching, burning, blisters, rash and desquamation. The causative substance of this seaweed dermatitis was not known till 1968 when
755:
The response of animals to debromoaplysiatoxin is variable. For example, the response of mice with P-388 lymphocytic leukemia to injections of debromoaplysiatoxin. The result was that the mice had good antileukemia response after treatment with debromoaplysiatoxin. The disadvantage was that these
735:
and was found to cause dermatitis. It has been found to be active at concentrations of 0.005 nmol per ear. The compound was first isolated from the digestive tract of the sea hare
Stylocheilus longicauda. Accidental skin contact with sea hare toxin extract led to skin irritations. This phenolic
820:
In rabbits and hairless mice topical application of debromoaplysiatoxin produced severe cutaneous inflammatory reactions. DAT produces dermatitis on the murine ear at a very low dose. This inflammation response and the mechanism of tumor promotion is likely to be mediated through activation of
543:
Because of the sterically complex and particular molecular structure, debromoaplysiatoxin is an attractive target for total synthesis. This compound combines spiro acetal, hemiacetal and diolide functionalities, which result in peculiar biological activities. To this date, only
Yoshita Kishi's
677:
Debromoaplysiatoxin has two effects on cell-growth: it has a tumor-promoting-activity as well as an anti-proliferation activity. Therefore, this compound is of interest for study: by finding which groups cause the tumor-promoting activity, and removing them, the new compound will only have an
825:
colony formation and is in agreement with a proliferative activation ('triggering') of the basal cell population from the normally quiescent Go state found in intact tracheal epithelium. The results also suggest that the polyacetates are good candidates for tumor promoters in vivo.
816:
growing on the dorsa of manatees would cause 24 h per day exposure to the toxin. It may be hypothesized that the continual presence of these toxin-producing cyanobacteria on the skin of these clinically ill animals may be contributing to their dermatologic disease. (5)
248:
InChI=1S/C32H48O10/c1-18(11-12-24(38-7)22-9-8-10-23(34)13-22)29-20(3)26-16-32(41-29)30(5,6)15-19(2)31(37,42-32)17-28(36)39-25(21(4)33)14-27(35)40-26/h8-10,13,18-21,24-26,29,33-34,37H,11-12,14-17H2,1-7H3/t18-,19+,20-,21+,24-,25+,26?,29+,31-,32-/m0/s1
682:
is found to be a cause for the tumor-promoting activity, and removal of the methoxy-group causes the antiproliferation activity to increase, without changing the tumor-promoting activity. Studies with analogs of debromoaplysiatoxin show that the
971:
Kikumori, M.; Yanagita, R.C.; Tokuda, H.; Suzuki, N.; Nagai, H.; Suenaga, K.; Irie, K. (June 2012). "Structure–Activity
Studies on the Spiroketal Moiety of a Simplified Analogue of Debromoaplysiatoxin with Antiproliferative Activity".
767:
against mice is also shown in Table 1. Aplysiatoxin was twice as toxic to mice as debromoaplysiatoxin. The characteristic symptom of these toxins in mice was diarrhea, which usually occurred 30 minutes after injection of toxins.
1165:
Horowitz, A.D.; Fujiki, H.; Weinstein, I.B.; Jeffrey, A.; Okin, E.; Moore, R.E.; Sugimara, T. (1983). "Comparative
Effects of Aplysiatoxin, Debromoaplysiatoxin, and Teleocidin on Receptor Binding and Phospholipid Metabolism".
1185:
Mass, M.J.; Lasley, J.A.; Marr, C.M.; Arnold, J.T.; Steele, V.E. (January 1987). "Colony formation enhancement of rat tracheal and nasal epithelial cells by polyacetate, indole alkaloid, and phorbol ester tumor promoters".
804:-dominated mats were also collected from the walls of manatee holding tanks. Manatee feces was sampled from the anal opening and debromoaplysiatoxin was identified in multiple samples, proving the exposure of manatees to
922:
Okamura, H.; Kuroda, S.; Ikegami, S.; Tomita, K.; Sugimoto, Y.; Sakaguchi, S.; Ito, Y.; Katsuki, T.; Yamaguchi, M. (November 1993). "A Formal
Synthesis of Aplysiatoxin - Enantioselective Synthesis of Kishi Aldehyde".
872:
Fujiki, H.; Ikegami, K.; Hakii, H.; Suganuma, M.; Yamaizumi, Z.; Yamazato, K.; Moore, R.E.; Sugimara, T. (1985). "A blue-green alga from
Okinawa contains aplysiatoxins, the third class of tumor promoters".
743:
of debromoaplysiatoxin are relatively nontoxic. Examination of the structure–activity relationship (SAR) of this hydrophobic region showed that the absence of the brominated molecule in moieties of
1103:
Harr, K.E.; Szabo, N.J.; Cichra, M.; Phlips, E.J. (August 2008). "Debromoaplysiatoxin in
Lyngbya-dominated mats on manatees (Trichechus manatus latirostris) in the Florida King's Bay ecosystem".
789:(a sea slug) has been established. This indicates that the compound isn't excreted by the animals causing a higher risk of death related to the amount of food consumed by the animal and its age.
517:
Years later, in 1994, local people of Hawaii, Maui and Oahu island in Hawaii were poisoned by food. The local residents of these islands often eat various types of algae including the red alga
808:
toxins. It is highly plausible that dermal disease in the manatee population is linked with exposure to
Lyngbyatoxins. In contrast to humans who would likely have periodic exposure to
779:
Furthermore, scientists speculate that debromoaplysiatoxin is accumulated in marine organisms by trophic transfer. In particular, trophic transfer of debromoaplysiatoxin from
523:. After taking samples of this red alga it turned out that they contained two toxins which were identical with aplysiatoxin and debromoaplysiatoxin. Moreover, they observed
895:
Nagai, H.; Yasumoto, T.; Hokama, Y. (July 1996). "Aplysiatoxin and debromoaplysiatoxin as the causative agents of a red alga
Gracilaria coronopifolia poisoning in Hawaii".
665:
formation must be achieved between the C.7 ketone and the C.11 hydroxygroup, after which lactone formation can seal the deal. This can be achieved by a method called
559:, followed by exposure to the epoxide. Hereby, a diastereomeric mixture of sulfones is formed. After reductive desulfurization and methylation, the formation of a
1046:
Mynderse, J.S.; Moore, R.E.; Kashiwagi, M.; Norton, T.R. (1977). "Antileukemia
Activity in the Oscillatoriaceae: Isolation of Debromoaplysiatoxin from Lyngbya".
261:
563:
side group can be achieved. This intermediate can be converted into a terminal epoxide by usage of classical synthetical operations, such as introducing
555:
that originates from optically active starting materials. This coupling reaction is most efficient when the sulfone is transformed into a dianion with
655:
1231:
1073:
Capper, A.; Tibbetts, I.R.; O'Neil, J.M.; Shaw, G.R. (July 2005). "The fate of Lyngbya majuscula toxins in three potential consumers".
842:
Hashimoto, Y.; Kamiya, H.; Yamazato, K.; Nozawa (1975). "Occurrence of a toxic blue-green alga inducing skin dermatitis in okinawa".
586:
The following step involves introducing an acidic sidechain on the C.9 hydroxyl group. This carboxylic, acidic side group is made of
736:
bislactones has been shown to have potent tumor promoting activities. Debromoaplysiatoxin produces erythema, blisters and necrosis.
690:
at position 3 and/or the methoxy group at position 15 in debromoaplysiatoxin would be responsible for the tumor-promoting activity.
239:
658:(DDQ) treatment, this β-keto thioester can be converted into an unstable diol, which is the acyclic precursor of the end product.
626:
614:. In order to produce the primary alcohol, it is necessary to adjust the protecting group of the C.30 once again, back to BOM.
495:
people in Okinawa, Japan, suffered from the same symptoms as the people in Hawaii. After researchers took samples in 1973 from
420:
457:
535:
produce aplysiatoxin and debromoaplysiatoxin, it's probable that they are the true origin of this food poisoning case.
203:
1271:
396:
378:
1224:
519:
23:
772:(a state of tiredness, weariness, fatigue, or lack of energy), muscular contractions and sometimes hind leg
607:
1138:
Solomon, A.E.; Stoughton, R.B. (1978). "Dermatitis from purified sea algae toxin (debromoaplysiatoxin)".
785:
666:
568:
355:
36:
622:
1424:
1419:
1398:
1217:
599:
560:
220:
740:
732:
651:
640:
580:
80:
1299:
479:
126:
756:
responses were only measured by a dose at which nearly 50 percent of the mice died of toxicity (
594:. The introduction is realized by protecting the C.29 and C.30 hydroxylgroups with respectively
661:
In order to introduce the ring system that characterizes debromoaplysiotoxin in this molecule,
591:
1429:
1120:
1028:
989:
474:
146:
1434:
1195:
1147:
1112:
1082:
1055:
1020:
981:
932:
904:
851:
714:
lines and binding activity for PKCδ, which plays a tumor suppressor role and is involved in
694:
344:
284:
90:
1380:
647:
618:
595:
551:
is formed in 22 steps of common chemistry. This sulfone is coupled with a straightforward
483:
224:
502:
In 1980 there was a new outbreak of seaweed dermatitis on Oahu island Hawaii. Samples of
68:)-13-Hydroxy-9--3--4,14,16,16-tetramethyl-2,6,10,17-tetraoxatricyclooctadecane-7,11-dione
1370:
1308:
611:
556:
511:
451:
368:
1024:
936:
792:
Also, dermal diseases in the manatee population is likely to be caused by exposure to
776:
were observed. Death was observed by 1.2 g of each algae in the mouse toxicity assay.
1413:
1355:
1350:
908:
855:
687:
679:
603:
610:(TBDPS). Thereafter, the carboxylic acid can successfully attach to the backbone by
514:. These three substances appeared to be the causative toxins of seaweed dermatitis.
486:
which has an anti-proliferative activity against various cancer cell lines in mice.
191:
1375:
1330:
1266:
544:
approach to synthesize debromoaplysiatoxin from scratch was found to be effective.
507:
1116:
1345:
1340:
1335:
1304:
1291:
1151:
564:
439:
606:, and subsequently replacing the C.30 protecting group with a more stable one,
1276:
1261:
1256:
1248:
1240:
1086:
684:
524:
312:
269:
123O((C)CC1(C)C)(CC(O((C)O)(CC(OC(C2)(C)(O3)((CC(C=4C=CC=C(C4)O)OC)C))=O))=O)O
137:
1199:
800:. Other algae were present in very low quantities and varied in composition.
1360:
1314:
1281:
773:
715:
698:
662:
625:
is formed out of the alcohol by a quadruplet of reactions with respectively
1124:
1059:
1032:
993:
621:
first, the yield of this idea has shown to be insufficient. Therefore, the
678:
anti-proliferation activity, and can be used as a therapy for cancer. The
769:
719:
576:
572:
1007:
Osborne, N.J.T.; Webb, P.M.; Shaw, G.R. (November 2001). "The toxins of
796:. The algal mat samples collected from manatee dorsum were dominated by
552:
548:
333:
178:
985:
587:
747:
toxins reduced malignant transformation and DNA synthesis in cells.
499:
they found out that this was the causative agent of the dermatitis.
450:
Except where otherwise noted, data are given for materials in their
166:
948:
946:
702:
113:
103:
705:
to play a tumor suppressor role and to be involved in apoptosis.
757:
617:
Although it would seem more logical to esterify the C.29 with a
434:
Carcinogenic, dermitis, oral and gastrointestinal inflammations
157:
1213:
1209:
821:
calcium activated, phospholipid-dependent protein kinase C.
208:
506:
revealed that this blue-green alga contained a mixture of
867:
865:
701:
is suggested to be involved in cancer cell growth, and
763:
Toxicity of aplysiatoxin and debromoaplysiatoxin from
731:
Debromoaplysiatoxin has activity against P-388 mouse
531:. In view of the fact that some blue-green alga like
1323:
1290:
1247:
472:is a toxic agent produced by the blue-green alga
1011:and their human and ecological health effects".
190:
89:
890:
888:
478:. This alga lives in marine waters and causes
1225:
8:
1098:
1096:
1232:
1218:
1210:
223:
145:
15:
656:2,3-dichloro-5,6-dicyano-1,4-benzoquinone
966:
964:
955:The Total Synthesis of Natural Products
834:
527:of a blue-green alga on the surface of
266:
244:
219:
602:(BOM), activating the sidechain with
7:
875:Japanese Journal of Cancer Research
579:derived anion interacts to form an
181:
165:
14:
1394:
1393:
296:
22:
953:Apsimon, John (February 1992).
454:(at 25 °C , 100 kPa).
974:Journal of Medicinal Chemistry
718:. The results showed that the
421:Occupational safety and health
302:
290:
1:
1117:10.1016/j.toxicon.2008.05.016
1025:10.1016/s0160-4120(01)00098-8
937:10.1016/s0040-4020(01)81547-7
909:10.1016/0041-0101(96)00014-1
856:10.1016/0041-0101(75)90034-3
1152:10.1001/archderm.114.9.1333
1075:Journal of Chemical Ecology
1451:
510:, debromoaplysiatoxin and
1389:
1087:10.1007/s10886-005-5800-5
1013:Environment International
637:-dicyclohexylcarbodiimide
448:
418:
413:
277:
257:
235:
73:
35:
30:
21:
652:1,1'-carbonyldiimidazole
520:Gracilaria coronopifolia
1140:Archives of Dermatology
608:tert-butyldiphenylsilyl
482:. Furthermore, it is a
1200:10.1093/carcin/8.1.179
1060:10.1126/science.403608
569:substitution reactions
957:. Wiley-Interscience.
786:Stylocheilus striatus
547:At first, a specific
17:Debromoaplysiatoxin
1366:Debromoaplysiatoxin
931:(46): 10531–10554.
733:lymphatic leukaemia
673:Mechanism of action
470:Debromoaplysiatoxin
345:Solubility in water
320: g·mol
127:Beilstein Reference
18:
1300:Cylindrospermopsin
751:Effects on animals
693:The activation of
667:macrolactonization
644:-chlorosuccinimide
480:seaweed dermatitis
458:Infobox references
16:
1407:
1406:
1054:(4289): 538–540.
1009:Lyngbya majuscula
986:10.1021/jm300566h
980:(11): 5614–5626.
497:Lyngbya majuscula
475:Lyngbya majuscula
466:Chemical compound
464:
463:
204:CompTox Dashboard
115:Interactive image
1442:
1397:
1396:
1234:
1227:
1220:
1211:
1204:
1203:
1182:
1176:
1175:
1162:
1156:
1155:
1146:(9): 1333–1335.
1135:
1129:
1128:
1100:
1091:
1090:
1081:(7): 1595–1606.
1070:
1064:
1063:
1043:
1037:
1036:
1004:
998:
997:
968:
959:
958:
950:
941:
940:
919:
913:
912:
892:
883:
882:
869:
860:
859:
839:
812:while swimming,
765:G. coronopifolia
695:protein kinase C
635:
623:β-keto thioester
529:G. coronopifolia
319:
304:
298:
292:
285:Chemical formula
228:
227:
212:
210:
194:
183:
169:
149:
117:
93:
26:
19:
1450:
1449:
1445:
1444:
1443:
1441:
1440:
1439:
1410:
1409:
1408:
1403:
1385:
1381:Aetokthonotoxin
1319:
1286:
1243:
1238:
1208:
1207:
1184:
1183:
1179:
1174:(4): 1529–1535.
1168:Cancer Research
1164:
1163:
1159:
1137:
1136:
1132:
1102:
1101:
1094:
1072:
1071:
1067:
1045:
1044:
1040:
1006:
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1001:
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969:
962:
952:
951:
944:
921:
920:
916:
894:
893:
886:
871:
870:
863:
841:
840:
836:
831:
753:
739:The dehydrated
729:
711:
709:Available forms
675:
648:sodium chlorite
633:
619:Blaise reaction
600:benzyloxymethyl
596:p-methoxybenzyl
561:cyclohexylidene
541:
492:
467:
460:
455:
431:
405:
387:
347:
317:
307:
301:
295:
287:
273:
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265:
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231:
213:
206:
197:
184:
172:
152:
129:
120:
107:
96:
83:
69:
12:
11:
5:
1448:
1446:
1438:
1437:
1432:
1427:
1422:
1412:
1411:
1405:
1404:
1402:
1401:
1390:
1387:
1386:
1384:
1383:
1378:
1373:
1371:Lyngbyatoxin-a
1368:
1363:
1358:
1353:
1348:
1343:
1338:
1333:
1327:
1325:
1321:
1320:
1318:
1317:
1312:
1309:Microcystin-LR
1302:
1296:
1294:
1288:
1287:
1285:
1284:
1279:
1274:
1269:
1264:
1259:
1253:
1251:
1245:
1244:
1239:
1237:
1236:
1229:
1222:
1214:
1206:
1205:
1194:(1): 179–181.
1188:Carcinogenesis
1177:
1157:
1130:
1111:(2): 385–388.
1092:
1065:
1038:
1019:(5): 381–392.
999:
960:
942:
914:
903:(7): 753–761.
884:
861:
833:
832:
830:
827:
752:
749:
728:
725:
710:
707:
674:
671:
612:esterification
557:n-butyllithium
540:
537:
512:lyngbyatoxin A
491:
488:
484:tumor promoter
465:
462:
461:
456:
452:standard state
449:
446:
445:
444:239.0±26.4 °C
442:
436:
435:
432:
429:
426:
425:
416:
415:
411:
410:
407:
403:
393:
392:
389:
385:
375:
374:
371:
369:Vapor pressure
365:
364:
361:
352:
351:
350:0.00911 mg/mL
348:
343:
340:
339:
336:
330:
329:
326:
322:
321:
315:
309:
308:
305:
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221:DTXSID80880084
216:
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177:
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125:
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98:
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94:
86:
84:
79:
76:
75:
71:
70:
39:
33:
32:
28:
27:
13:
10:
9:
6:
4:
3:
2:
1447:
1436:
1433:
1431:
1428:
1426:
1423:
1421:
1418:
1417:
1415:
1400:
1392:
1391:
1388:
1382:
1379:
1377:
1374:
1372:
1369:
1367:
1364:
1362:
1359:
1357:
1356:Cyanopeptolin
1354:
1352:
1351:Cyanobacterin
1349:
1347:
1344:
1342:
1339:
1337:
1334:
1332:
1329:
1328:
1326:
1322:
1316:
1313:
1310:
1306:
1303:
1301:
1298:
1297:
1295:
1293:
1289:
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1280:
1278:
1275:
1273:
1270:
1268:
1265:
1263:
1260:
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1255:
1254:
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1250:
1246:
1242:
1235:
1230:
1228:
1223:
1221:
1216:
1215:
1212:
1201:
1197:
1193:
1189:
1181:
1178:
1173:
1169:
1161:
1158:
1153:
1149:
1145:
1141:
1134:
1131:
1126:
1122:
1118:
1114:
1110:
1106:
1099:
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1088:
1084:
1080:
1076:
1069:
1066:
1061:
1057:
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1049:
1042:
1039:
1034:
1030:
1026:
1022:
1018:
1014:
1010:
1003:
1000:
995:
991:
987:
983:
979:
975:
967:
965:
961:
956:
949:
947:
943:
938:
934:
930:
926:
918:
915:
910:
906:
902:
898:
891:
889:
885:
881:(4): 257–259.
880:
876:
868:
866:
862:
857:
853:
849:
845:
838:
835:
828:
826:
822:
818:
815:
811:
807:
803:
799:
795:
790:
788:
787:
782:
777:
775:
771:
766:
761:
759:
750:
748:
746:
742:
741:anhydrotoxins
737:
734:
726:
724:
721:
717:
708:
706:
704:
700:
696:
691:
689:
688:hydroxy group
686:
681:
680:methoxy-group
672:
670:
668:
664:
659:
657:
653:
649:
645:
643:
638:
636:
629:
624:
620:
615:
613:
609:
605:
604:acid chloride
601:
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589:
584:
582:
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570:
566:
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398:
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384:
380:
377:
376:
373:0.0±2.7 mmHg
372:
370:
367:
366:
362:
360:
359:
354:
353:
349:
346:
342:
341:
338:1.2±0.1 g/cm
337:
335:
332:
331:
328:White powder
327:
324:
323:
316:
314:
311:
310:
289:
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245:
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38:
34:
29:
25:
20:
1376:Microviridin
1365:
1331:Aplysiatoxin
1305:Microcystins
1292:Hepatotoxins
1267:Antillatoxin
1191:
1187:
1180:
1171:
1167:
1160:
1143:
1139:
1133:
1108:
1104:
1078:
1074:
1068:
1051:
1047:
1041:
1016:
1012:
1008:
1002:
977:
973:
954:
928:
924:
917:
900:
896:
878:
874:
850:(2): 95–96.
847:
843:
837:
823:
819:
813:
809:
805:
801:
797:
793:
791:
784:
781:L. majuscula
780:
778:
764:
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738:
730:
712:
692:
676:
660:
654:(CDI). With
641:
631:
627:
616:
585:
546:
542:
533:L. majuscula
532:
528:
518:
516:
508:aplysiatoxin
504:L. majuscula
503:
501:
496:
493:
473:
469:
468:
430:Main hazards
419:
400:
382:
357:
74:Identifiers
65:
61:
57:
53:
49:
45:
41:
1425:Phycotoxins
1420:Cyanotoxins
1346:Coibamide A
1341:Caldoramide
1336:Apratoxin A
1249:Neurotoxins
1241:Cyanotoxins
925:Tetrahedron
798:Lyngbya spp
685:hemi-acetal
565:acetic acid
440:Flash point
424:(OHS/OSH):
325:Appearance
278:Properties
1414:Categories
1277:Kalkitoxin
1262:Guanitoxin
1257:Anatoxin-a
829:References
598:(MPM) and
575:. Next, a
525:parasitism
313:Molar mass
138:ChemSpider
102:3D model (
91:52423-28-6
81:CAS Number
37:IUPAC name
1361:Cyclamide
1315:Nodularin
1282:Saxitoxin
774:paralysis
716:apoptosis
663:hemiketal
592:arabidose
573:tosylates
539:Synthesis
1430:Lactones
1399:Category
1125:18585400
1033:11757852
994:22625994
770:Lethargy
727:Toxicity
720:dimethyl
577:dithiane
414:Hazards
397:Basicity
132:4624539
1435:Phenols
1105:Toxicon
1048:Science
897:Toxicon
844:Toxicon
814:Lyngbya
810:Lyngbya
806:Lyngbya
802:Lyngbya
794:Lyngbya
745:Lyngbya
646:(NCS),
639:(DCC),
581:alcohol
553:epoxide
549:sulfone
490:History
379:Acidity
334:Density
318:592.726
192:5352033
179:PubChem
147:4509004
1307:(e.g.
1123:
1031:
992:
588:xylose
262:SMILES
167:C05148
31:Names
1324:Other
783:into
571:with
391:9.36
240:InChI
104:JSmol
1272:BMAA
1121:PMID
1029:PMID
990:PMID
758:LD50
703:PKCδ
699:PKCα
650:and
590:and
363:4.2
356:log
158:KEGG
1196:doi
1148:doi
1144:114
1113:doi
1083:doi
1056:doi
1052:196
1021:doi
982:doi
933:doi
905:doi
852:doi
760:).
567:or
409:-3
209:EPA
182:CID
64:,14
60:,13
1416::
1190:.
1172:43
1170:.
1142:.
1119:.
1109:52
1107:.
1095:^
1079:31
1077:.
1050:.
1027:.
1017:27
1015:.
988:.
978:55
976:.
963:^
945:^
929:49
927:.
901:34
899:.
887:^
879:76
877:.
864:^
848:13
846:.
669:.
583:.
406:)
399:(p
388:)
381:(p
306:10
300:48
294:32
56:,9
52:,5
48:,4
44:,3
40:(1
1311:)
1233:e
1226:t
1219:v
1202:.
1198::
1192:8
1154:.
1150::
1127:.
1115::
1089:.
1085::
1062:.
1058::
1035:.
1023::
996:.
984::
939:.
935::
911:.
907::
858:.
854::
642:N
634:′
632:N
630:,
628:N
404:b
401:K
386:a
383:K
358:P
303:O
297:H
291:C
211:)
207:(
106:)
66:R
62:S
58:R
54:S
50:S
46:R
42:S
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