127:
209:
InChI=1S/C96H136Cl3NO35/c1-3-4-15-23-47(98)75(109)79(113)80(114)76(110)49(102)35-50(103)88(135-96-85(119)78(112)74(43-101)132-96)51(104)38-70-77(111)81(115)82(116)94(131-70)95-84(118)83(117)93-62(130-95)31-30-61(129-93)90-54(107)39-72-87(133-90)48(99)34-71(126-72)91-55(108)40-73-92(134-91)53(106)36-64(125-73)57-26-27-58-63(121-57)33-44(2)86(127-58)59-28-29-60-89(128-59)52(105)37-65-67(123-60)42-68-69(124-65)41-66-56(122-68)25-24-46(120-66)22-18-14-17-21-45(100)20-16-12-10-8-6-5-7-9-11-13-19-32-97/h1,8,10,12,14,16-19,22,32,44-96,101-119H,7,9,20-21,23-31,33-43,100H2,2H3/b10-8+,16-12+,17-14+,22-18+,32-19+/t44-,45+,46+,47-,48+,49?,50?,51?,52+,53+,54-,55+,56-,57+,58+,59?,60-,61?,62+,63-,64?,65-,66-,67-,68+,69+,70+,71?,72+,73+,74+,75?,76?,77-,78+,79?,80?,81+,82-,83+,84-,85+,86-,87+,88?,89+,90+,91+,92+,93-,94?,95+,96+/m0/s1
186:
24:
611:
459:
Prymnesin-2 causes hemolysis by direct interaction between toxin and cell surface. Partly due to interaction with cellular lipids, mainly to interaction with a specific binding site on the blood cell surface. This is supported by the observation of competitive inhibition by the prymnesin-2 analogues,
468:
Prymnesin-2 is an ichthyotoxic compound with the ability to hemolyze blood. 2.5 nM is needed for a 50% hemolysis rate of a 1% rat blood cell suspension, and 9 nM is enough for killing freshwater fish. The hemolytic and ichthyotoxic properties increase when the pH of the solution rises from 7 to 8.
410:
and prymnesin-2 is the glycosidic residues: L-arabinose, D-galactose and D-ribose, yet prymnesin-2 and prymnesin-1 show comparable activities. Prymnesins also have unique features: The possession of only one methyl, but three chlorine atoms, four C-C triple bonds, sugars and an amino group.
827:
Fallon, Timothy R.; Shende, Vikram V.; Wierzbicki, Igor H.; Pendleton, Amanda L.; Watervoort, Nathan F.; Auber, Robert P.; Gonzalez, David J.; Wisecaver, Jennifer H.; Moore, Bradley S. (2024-08-09). "Giant polyketide synthase enzymes in the biosynthesis of giant marine polyether toxins".
419:
Prymnesin-1 and prymnesin-2 are both are derived from acetate-related (i.e. polyketide) metabolism, based on knowledge about the structure of the prymnesins. In general primary and secondary metabolites such as fatty acids, polyketides and non-ribosomal peptides are synthesised by the
233:
C1C2()O(C3C(4()O(C5C(6()O(C7CC8()O(C9O(((9O)O)O)CC(C(C(CC(C(C(C(C((CC#CC#C)Cl)O)O)O)O)O)O)O%10O((%10O)O)CO)O)((8()O7)O)O)(C6()O5)O)Cl)(C4()O3)O)O)CC2()O1C%11CC%12()O%13()C%14()O%15()CC(/C=C/C=C/C(C/C=C/C=C/C#CCCC#C/C=C/Cl)N)O%15()C%14()O%13()C(%12()O%11)O
952:
Morohashi, Akio; Satake, Masayuki; Oshima, Yasukatsu; Igarashi, Tomoji; Yasumoto, Takeshi (2001). "Absolute configuration at C14 and C85 in prymnesin-2, a potent hemolytic and ichthyotoxic glycoside isolated from the red tide alga
Prymnesium parvum".
662:
Igarashi, Tomoji; Satake, Masayuki; Yasumoto, Takeshi (1999). "Structures and
Partial Stereochemical Assignments for Prymnesin-1 and Prymnesin-2: Potent Hemolytic and Ichthyotoxic Glycosides Isolated from the Red Tide AlgaPrymnesium parvum".
1100:
Miller, Carrie J.; Roelke, Daniel L.; Davis, Stephen E.; Li, Hsiu-Ping; Gable, George (2008). "The role of inflow magnitude and frequency on plankton communities from the
Guadalupe Estuary, Texas, USA: Findings from microcosm experiments".
1056:
Buyukates, Yesim; Roelke, Daniel (2005-10-01). "Influence of Pulsed
Inflows and Nutrient Loading on Zooplankton and Phytoplankton Community Structure and Biomass in Microcosm Experiments Using Estuarine Assemblages".
66:-((4aS,5aS,6aR,7aS,10S,11aS,12aR,13aS,15R,15aR)-10-((R,1E,3E,8E,10E,18E)-6-amino-19-chlorononadeca-1,3,8,10,18-pentaen-12,16-diyn-1-yl)-15-hydroxyoctadecahydropyranopyranopyranopyranooxepin-2-yl)-8'-chloro-3',3
995:
James T. L., De La Cruz A.. Prymnesium parvum Carter (Chrysophyceae) as a suspect of mass mortalities of fish and shellfish communities in western Texas, Texas
Journal of Science, 1989, vol. 41 (pp. 429-430).
72:-methyldotriacontahydro-pyran]-6-yl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)-11-chloro-3-(((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)hexadeca-13,15-diyne-2,4,6,7,8,9,10-heptaol
460:
which assume the presence of a specific binding site on the blood cell surface. Also the process of toxin molecule aggregation may be involved in the main mechanism of the haemolytic activity.
432:
The mechanism of action of prymnesin-2 remains to be determined. Prymnesin-2 and prymnesin-1 show comparable activities. Prymnesin-2 has shown multiple functionalities, such as potent
595:
blooms dramatically increased in the US, where the organism has invaded lakes and rivers throughout southern regions and most recently into northern regions. The magnitude of
703:
Igarashi, Tomoji; Satake, Masayuki; Yasumoto, Takeshi (1996). "Prymnesin-2: A Potent
Ichthyotoxic and Hemolytic Glycoside Isolated from the Red Tide Alga Prymnesium parvum".
475:
As seen in the table below, prymnesin-2 is highly hemolytic for blood cells of different animal species, even when compared to the already highly hemolytic toxin saponin.
362:
worldwide, causing massive fish killings. When these algal blooms occur, this compound poses a threat to the local fishing industry. This is especially true for
1005:
Roelke, Daniel; Augustine, Sarah; Buyukates, Yesim (2003-11-01). "Fundamental
Predictability in Multispecies Competition: The Influence of Large Disturbance".
398:, which means that it can act both as base and an acid. This is because all 16 hydroxyls, except for one at C32, are concentrated on carbons C48-84, and there
1187:
225:
424:. In 2024 the backbone of A-type prymnesins like prymnesin-2 was reported to be made by giant polyketide synthase enzymes dubbed the "PKZILLAs".
406:
moiety at C77. This might lead to interaction with biomembranes, which is thought to be the basis of its toxicity. The difference between
866:
Igarashi, T.; Aritake, S.; Yasumoto, T. (1998). "Biological activities of prymnesin-2 isolated from a red tide alga
Prymnesium parvum".
200:
879:
909:
Granéli, Edna; Salomon, Paulo S. (1 February 2010). "Factors
Influencing Allelopathy and Toxicity in Prymnesium parvum".
310:
472:
Besides the lytic effect on blood cells, hepatocytes, Hela cells and artificial liposomes are affected by prymnesin-2.
1162:
164:
1167:
1152:
421:
1157:
1147:
599:
blooms are also increasing over the past decade compared to 30 years ago, with massive fish killings as result.
1177:
591:
bloom occurred in 1985 in a semi-arid region of the country (Pecos River, Texas). Since then, the incidence of
391:
36:
1182:
1142:
1110:
918:
437:
181:
1192:
359:
93:
620:
1082:
1038:
1074:
1030:
1022:
978:
970:
934:
891:
883:
845:
809:
758:
750:
680:
338:
1118:
1066:
1014:
962:
926:
875:
837:
799:
789:
742:
733:
Yasumoto, Takeshi (2001). "The chemistry and biological function of natural marine toxins".
712:
672:
469:
Prymnesin-2 causes calcium ion influx into C6 rat glioma cells at a concentration of 70 nM.
326:
248:
103:
1172:
185:
778:"Prymnesins: Toxic Metabolites of the Golden Alga, Prymnesium parvum Carter (Haptophyta)"
1114:
922:
616:
804:
777:
452:
influx into cultured cells. The hemolytic potency of prymnesin-2 exceeds that of plant
363:
304:
152:
23:
1136:
930:
1086:
1042:
639:
351:
634:
395:
1122:
1070:
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1026:
974:
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849:
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684:
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841:
433:
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347:
343:
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1034:
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762:
895:
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139:
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676:
880:
10.1002/(SICI)1522-7189(199802)6:1<35::AID-NT7>3.0.CO;2-7
746:
436:
activity and diverse biological activities, such as mouse lethality,
399:
303:
Except where otherwise noted, data are given for materials in their
1018:
479:
Table1. Sensitivities of blood cells from different animal species
354:
properties. In a purified form it appears as a pale yellow solid.
126:
116:
366:, as the compound can reach critical concentrations more easily.
169:
911:
JAWRA Journal of the
American Water Resources Association
776:
Manning, Schonna R.; La Claire, John W. (2010-03-16).
671:(37). American Chemical Society (ACS): 8499–8511.
151:
728:
726:
102:
8:
374:The structural formula of prymnesin-2 is: C
698:
696:
694:
184:
15:
803:
793:
705:Journal of the American Chemical Society
665:Journal of the American Chemical Society
477:
651:
230:
205:
180:
212:Key: WCHCDYFGLWOFCV-NSPCONBQSA-N
7:
1103:Estuarine, Coastal and Shelf Science
861:
859:
1188:Halogen-containing natural products
142:
14:
390:. The compound exhibits multiple
931:10.1111/j.1752-1688.2009.00395.x
609:
272:
266:
260:
40:(11S)-1-((2R,3R,4R,5S)-6-((2'R,2
22:
307:(at 25 °C , 100 kPa).
587:In the US, the first recorded
275:
254:
1:
1209:
1123:10.1016/j.ecss.2008.07.006
1071:10.1007/s10750-005-5195-x
394:centers. The molecule is
301:
241:
221:
196:
86:
78:
35:
30:
21:
370:Structure and reactivity
1007:The American Naturalist
842:10.1126/science.ado3290
358:is responsible for red
440:and activity inducing
346:family and has potent
492:Relative to saponin
360:harmful algal blooms
342:. It belongs to the
1115:2008ECSS...80...67M
923:2010JAWRA..46..108G
735:The Chemical Record
480:
428:Mechanism of action
297: g·mol
58:S,8R,8aR,8'R,8'aS,8
18:
1163:Secondary alcohols
619:has a profile for
583:Effects on animals
478:
311:Infobox references
16:
1168:Conjugated enynes
1153:Conjugated diynes
967:10.1002/chir.1184
836:(6709): 671–678.
795:10.3390/md8030678
717:10.1021/ja9534112
677:10.1021/ja991740e
625:
580:
579:
486:Prymnesin-2 (nM)
456:by 50.000 times.
403:
339:Prymnesium parvum
319:Chemical compound
317:
316:
165:CompTox Dashboard
128:Interactive image
1200:
1158:Primary alcohols
1148:Polyether toxins
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26:
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1178:Organochlorides
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438:ichthyotoxicity
430:
422:acetate pathway
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70:-pentahydroxy-7
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1128:
1092:
1065:(1): 233–249.
1048:
1019:10.1086/378750
1013:(5): 615–623.
997:
988:
961:(9): 601–605.
944:
917:(1): 108–120.
901:
868:Natural Toxins
855:
819:
788:(3): 678–704.
768:
741:(3): 228–242.
722:
711:(2): 479–480.
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1059:Hydrobiologia
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489:Saponin (nM)
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404:-xylofuranose
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20:
1109:(1): 67–73.
1106:
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958:
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874:(1): 35–41.
871:
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822:
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782:Marine Drugs
781:
771:
738:
734:
708:
704:
668:
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640:Prymnesin-B1
622:prymnesin-2
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418:
415:Biosynthesis
373:
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352:ichthyotoxic
337:
322:
321:
87:Identifiers
79:Other names
71:
69:
63:
61:
55:
53:
49:
48:R,4aR,4'aR,4
47:
43:
41:
17:Prymnesin 2
1183:Halohydrins
1143:Phycotoxins
635:Prymnesin-1
624:(Q55630719)
408:prymnesin-1
323:Prymnesin-2
242:Properties
104:168010-52-4
1193:Glycosides
1137:Categories
646:References
396:amphoteric
335:haptophyte
286:Molar mass
115:3D model (
94:CAS Number
37:IUPAC name
1079:0018-8158
1027:0003-0147
975:1520-636X
955:Chirality
939:1752-1688
888:1056-9014
850:0036-8075
755:1528-0691
685:0002-7863
597:P. parvum
593:P. parvum
589:P. parvum
434:hemolytic
356:P. parvum
348:hemolytic
344:prymnesin
153:132524596
1087:40194710
1043:19980618
1035:14618539
983:11579456
814:20411121
763:11895121
603:See also
553:Chicken
464:Toxicity
331:secreted
329:that is
1111:Bibcode
919:Bibcode
896:9851510
830:Science
805:2857367
617:Scholia
511:Rabbit
454:saponin
333:by the
140:PubChem
54:aR,6R,6
44:R,3'S,3
1173:Amines
1085:
1077:
1041:
1033:
1025:
981:
973:
937:
894:
886:
848:
812:
802:
761:
753:
683:
573:11500
559:17000
548:38000
545:23000
539:Sheep
534:50000
531:25000
517:15000
503:17000
497:Mouse
392:chiral
325:is an
226:SMILES
68:,7,8,8
56:S,7S,7
31:Names
1083:S2CID
1039:S2CID
576:7200
567:Carp
562:8900
520:8800
506:6800
201:InChI
117:JSmol
64:aS)-6
1075:ISSN
1031:PMID
1023:ISSN
979:PMID
971:ISSN
935:ISSN
892:PMID
884:ISSN
846:ISSN
810:PMID
759:PMID
751:ISSN
681:ISSN
570:1.6
556:1.9
542:0.6
528:0.5
525:Dog
514:1.7
500:2.5
350:and
81:PRM2
62:aR,8
50:aR,4
1119:doi
1067:doi
1063:548
1015:doi
1011:162
963:doi
927:doi
876:doi
838:doi
834:385
800:PMC
790:doi
743:doi
713:doi
709:118
673:doi
669:121
380:136
295:.47
293:970
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