Table 2.
Physicochemical characteristics of brevetoxin (BTX) metabolites reported in marine organisms.
| Group | Compound Identification Number (ID) |
Metabolite | Other Existing Names | Molecular Formula |
Monoisotopic Mass (Da) | LogP 1 | Sample | References |
|---|---|---|---|---|---|---|---|---|
| A-type BTXs | #4 | Oxidized BTX-1 | Oxidized PbTx-1; PbTx-1-carboxylic acid |
C49H70O14 | 882.5 | / | Clams (mercenaria sp.) | [22] |
| #6 | Open A-ring, oxidized BTX-1 | Open A-ring of oxidized PbTx-1; A-type opened A-ring derivative |
C49H72O15 | 900.5 | / | Clams (mercenaria sp.); Oysters (Crassostrea virginica) |
[22,35] | |
| #7 | Open A-ring BTX-7 | Open A-ring PbTx-7 | C49H74O14 | 886.5 | / | Oysters (Crassostrea virginica); Pinfish (Lagodon rhomboides); Spot (Leiostomus xanthurus) |
[35,39,48] | |
| #52 | Taurine-BTX-A | N-taurine conjugate of oxidized BTX-1 | C51H75NO16S | 989.5 | / | Clams (mercenaria sp.) | [22] | |
| #53 | Cysteine–BTX-A | Cysteine–PbTx-A; Cysteine-PbTx-1; Cysteine-BTX-1 |
C52H79NO15S | 989.5 | / | Clams (mercenaria sp.); Oysters (Crassostrea virginica); Pinfish (Lagodon rhomboides); Spot (Leiostomus xanthurus) |
[23,35,39,48] | |
| #54 | Cysteine–BTX-A sulfoxide | Cysteine–PbTx-A sulfoxide; Sulfoxide cysteine conjugate of PbTx-1 |
C52H79NO16S | 1005.5 | / | Clams (mercenaria sp.); Oysters (Crassostrea virginica); Pinfish (Lagodon rhomboides); Spot (Leiostomus xanthurus) |
[23,35,39,48] | |
| #55 | Open A-ring cysteine-BTX-A | Open A-ring cysteine–PbTx-A | C52H81NO16S | 1007.5 | / | Clams (mercenaria sp.); Oysters (Crassostrea virginica) |
[22,34,35,39] | |
| #56 | Glutathione-BTX-A | Glutathione-PbTx-A | C59H89N3O19S | 1175.6 | / | Oysters (Crassostrea virginica) | [23,34,39] | |
| #57 | Glycine-cysteine-BTX-A | Glycine-cysteine-PbTx-A | C54H82N2O16S | 1046.5 | / | Clams (mercenaria sp.); Oysters (Crassostrea virginica) |
[23,39] | |
| #58 | N-hexadecanoyl-cysteine–BTX-A | N-hexadecanoyl-cysteine–PbTx-A | C68H109NO16S | 1227.7 | / | Oysters (Crassostrea virginica) | [39] | |
| #59 | Metabolite not named | / | C51H76O16S | 976.5 | / | Oysters (Crassostrea virginica) | [39] | |
| B-type BTXs | #8 | BTX-2 | PbTx-2; T47; GB-2; T34; BTX-B | C50H70O14 | 894.5 | 6.2 | Cockles (Austrovenus stutchburyi); Mussels (Perna canaliculus); Oysters (Crassostrea virginica, Crassostrea gigas); Sharks (Rhizoprionodon terraenovae, Sphyrna tiburo); Shrimps (Litopenaeus vannamei) |
[10,21,30,31,32,49,64,112] |
| #9 | BTX-3 | PbTx-3; GB-3; T17; dihydro-BTX-B; aldehyde-reduced PbTx-2 | C50H72O14 | 896.5 | 6.4 | Bottlenose dolphins (Tursiops Truncatus); Clams (Mercenaria sp.); Cockles (Austrovenus stutchburyi); Gastropods (Triplofusus giganteus, Sinistrofulgur sinistrum, Cinctura hunteria, Strombus alatus, Fulguropsis spirata); Mussels (Perna canaliculus); Oysters (Crassostrea gigas, Crassostrea virginica); Pinfish (Lagodon rhomboides); Rays (Dasyatis sabina); Sharks (Carcharhinus limbatus, Rhizoprionodon terraenovae, Sphyrna tiburo); Spot (Leiostomus xanthurus) |
[10,17,20,21,22,31,32,33,48,49,50,66] | |
| #16 | Open A-ring BTX-3 | Open-ring PbTx-3 | C50H74O15 | 914.5 | / | Gastropods (Triplofusus giganteus, Sinistrofulgur sinistrum, Cinctura hunteria, Strombus alatus, Fulguropsis spirata); Oysters (Crassostrea virginica); Pinfish (Lagodon rhomboides); Spot (Leiostomus xanthurus) |
[17,35,48] | |
| #12 | BTX-9 | Reduced-BTX-2 | C50H74O14 | 898.5 | 6.3 | Oysters (Crassostrea virginica) | [34,39] | |
| #13 | BTX-B5 | Oxidized BTX-2; Oxidized PbTx-2; PbTx-2-carboxylic acid |
C50H70O15 | 910.5 | 6.7 | Clams (Mercenaria sp., Macrocallista nimbosa);
Cockles (Austrovenus stutchburyi); Gastropods (Triplofusus giganteus, Sinistrofulgur sinistrum, Cinctura hunteria, Strombus alatus, Fulguropsis spirata); Mussels (Perna canaliculus); Oysters (Crassostrea gigas, Crassostrea virginica) |
[17,22,23,31,32,33,39] | |
| #15 | Open A-ring, oxidized BTX-2 | Open ring, oxidized PbTx-2; Open A-ring BTX-B5; PbTx-2-open ring-carboxylic acid |
C50H72O16 | 928.5 | / | Clams (mercenaria sp.); Oysters (Crassostrea virginica) |
[22,23,35] | |
| #60 | Oxidized, open D-ring tetradecanoyl-BTX-2 | BTX-B3; Oxidized, open D-ring myristoyl-BTX-2 |
C64H96O17 | 1136.7 | / | Mussels (Perna canaliculus) | [36] | |
| #61 | Oxidized, open D-ring hexadecanoyl-BTX-2 | BTX-B3; Oxidized, open D-ring palmitoyl-BTX-2 |
C66H100O17 | 1164.7 | / | Mussels (Perna canaliculus) | [36] | |
| #62 | Taurine-BTX-B | BTX-B1; N-taurine conjugate of oxidized PbTx-2; N-taurine conjugate of BTX-B5 |
C52H75NO17S 2 | 1017.5 2 | / | Clams (Mercenaria sp.; Macrocallista nimbosa); Cockles (Austrovenus stutchburyi); Gastropods (Triplofusus giganteus, Sinistrofulgur sinistrum, Cinctura hunteria, Strombus alatus, Fulguropsis spirata); Mussels (Perna canaliculus); Oysters (Crassostrea gigas) |
[17,20,22,23,31,32,33,37] | |
| #63 | Cysteine-BTX-B | S-desoxy-BTX-B2; S-deoxy-BTX-B2; Cysteine-BTX-B; Cysteine-PbTx; Cysteine-PbTx-B; Cysteine conjugate of PbTx-2 |
C53H79NO16S | 1017.5 | / | Clams (Mercenaria sp.; Macrocallista nimbosa); Gastropods (Triplofusus giganteus, Sinistrofulgur sinistrum, Cinctura hunteria, Strombus alatus, Fulguropsis spirata); Oysters (Crassostrea virginica); Pinfish (Lagodon rhomboides); Sharks (Carcharhinus limbatus, Rhizoprionodon terraenovae, Sphyrna tiburo); Spot (Leiostomus xanthurus); Rays (Dasyatis sabina) |
[17,22,23,28,34,35,48,49] | |
| #64 | Cysteine-BTX-B sulfoxide | BTX-B2; Cysteine-PbTx-B sulfoxide; Cysteine-PbTx sulfoxide; Oxidised-S-desoxy-BTX-B2 |
C53H79NO17S | 1033.5 | 4.3 | Clams (Mercenaria sp., Macrocallista nimbosa); Gastropods (Triplofusus giganteus, Sinistrofulgur sinistrum, Cinctura hunteria, Strombus alatus, Fulguropsis spirata); Mussels (Perna canaliculus); Oysters (Crassostrea virginica); Pinfish (Lagodon rhomboides); Sharks (Carcharhinus limbatus, Rhizoprionodon terraenovae, Sphyrna tiburo); Spot (Leiostomus xanthurus); Rays (Dasyatis sabina) |
[17,22,23,28,34,35,38,48,49] | |
| #65 | Oxidized cysteine-BTX-2 | Cysteine conjugate of oxidized PbTx-2 | C53H77NO17S | 1031.5 | / | Oysters (Crassostrea virginica) | [39] | |
| #66 | Open A-ring cysteine-BTX-B | Open A-ring S-desoxy-BTX-B2; Open A-ring cysteine–PbTx-B; Open A-ring cysteine–PbTx-2 |
C53H81NO17S | 1035.5 | / | Clams (mercenaria sp.); Oysters (Crassostrea virginica) |
[22,34,35,39] | |
| #67 | Glycine-cysteine-BTX-B | Glycine-cysteine-PbTx-B | C55H82N2O17S | 1074.5 | / | Clams (mercenaria sp.); Oysters (Crassostrea virginica) |
[22,34,39] | |
| #68 | γ-glutamyl-cysteine-BTX-B | γ-glutamyl-cysteine-PbTx-B | C58H86N2O19S | 1146.6 | / | Clams (mercenaria sp.); Oysters (Crassostrea virginica) |
[22,34,39] | |
| #69 | Glutathione-BTX-B | Glutathione-PbTx-B | C60H89N3O20S | 1203.6 | / | Clams (mercenaria sp.); Oysters (Crassostrea virginica) |
[22,34,39] | |
| #70 | N-tetradecanoyl-cysteine-BTX-B sulfoxide | BTX-B4; N-tetradecanoyl-BTX-B2; N-myristoyl-BTX-B2; N-myristoyl-cysteine- PbTx-B sulfoxide |
C67H105NO18S | 1243.7 | 11.3 | Mussels (Perna canaliculus); Oysters (Crassostrea virginica) | [39,40] | |
| #71 | N-hexadecanoyl-cysteine-BTX-B sulfoxide | BTX-B4; N-hexadecanoyl-BTX-B2; N-palmitoyl-BTX-B2; N-hexadecanoyl-cysteine–PbTx-B sulfoxide |
C69H109NO18S | 1271.7 | 12.3 | Clams (mercenaria sp.); Mussels (Perna canaliculus); Oysters (Crassostrea virginica) |
[22,39,40] | |
| #72 | N- (hydroxy-hexadecenoyl)-cysteine-BTX-B sulfoxide |
N- (hydroxy-hexadecenoyl)-BTX-B2 |
C69H107NO19S | 1285.7 | / | Clams (mercenaria sp.) | [22] | |
| #73 | N-octadecanoyl-cysteine-BTX-B sulfoxide | N-octadecanoyl-BTX-B2 | C71H113NO18S | 1299.8 | / | Clams (mercenaria sp.) | [22] | |
| #74 | N-octadecenoyl-cysteine-BTX-B sulfoxide | N-octadecenoyl-BTX-B2 | C71H111NO18S | 1297.8 | / | Clams (mercenaria sp.) | [22] | |
| #75 | N- (hydroxy-eicosanoyl)-cysteine-BTX-B sulfoxide |
N- (hydroxy-eicosanoyl)-BTX-B2 |
C73H117NO19S | 1343.8 | / | Clams (mercenaria sp.) | [22] | |
| #76 | N-arachidonyl-cysteine-BTX-B sulfoxide | N-arachidonyl-BTX-B2 | C73H109NO18S | 1319.7 | / | Clams (mercenaria sp.) | [22] | |
| #77 | N-didecenoyl-cysteine-BTX-B sulfoxide | N-didecenoyl-BTX-B2 | C73H115NO18S | 1325.8 | / | Clams (mercenaria sp.) | [22] | |
| #78 | N-tetradecanoyl-cysteine-BTX-B | N-tetradecanoyl-cysteine–PbTx-B | C67H105NO18S | 1243.7 | / | Oysters (Crassostrea virginica) | [39] | |
| #79 | N-hexadecanoyl-cysteine-BTX-B | N-hexadecanoyl-cysteine–PbTx-B; N-hexadecanoyl-S-deoxy-BTX-B2 |
C69H109NO17S | 1255.7 | / | Clams (mercenaria sp.); Oysters (Crassostrea virginica) |
[22,39] | |
| #80 | N-(hydroxy-hexadecenoyl)-cysteine-BTX-B | N-(hydroxy-hexadecenoyl)-S-deoxy-BTX-B2 | C69H107NO18S | 1269.7 | / | Clams (mercenaria sp.) | [22] | |
| #81 | N-octadecanoyl-cysteine-BTX-B | N-octadecanoyl-cysteine–PbTx-B; N-octadecanoyl-S-deoxy-BTX-B2 |
C71H113NO17S | 1283.8 | / | Clams (mercenaria sp.); Oysters (Crassostrea virginica) |
[22,39] | |
| #82 | N-octadecenoyl-cysteine-BTX-B | N-octadecenoyl-cysteine–PbTx-B | C71H111NO17S | 1281.8 | / | Oysters (Crassostrea virginica) | [39] | |
| #83 | N-eicosenoyl-cysteine-BTX-B | N-eicosenoyl-cysteine–PbTx-B | C73H115NO17S | 1309.8 | / | Oysters (Crassostrea virginica) | [39] | |
| #84 | N- (hydroxy-eicosanoyl)-cysteine-BTX-B |
N-(hydroxy-eicosanoyl)-cysteine–PbTx-B; N-(hydroxy-eicosanoyl)-S-deoxy-BTX-B2 |
C73H117NO18S | 1327.8 | / | Clams (mercenaria sp.); Oysters (Crassostrea virginica) |
[22,39] | |
| #85 | Glycine-(N-tetradecanoyl)-cysteine-BTX-B | Glycine-(N-tetradecanoyl-cysteine)–PbTx-B | C69H108N2O18S | 1284.7 | / | Oysters (Crassostrea virginica) | [39] | |
| #86 | Glycine-(N-hexadecanoyl)-cysteine-BTX-B | Glycine-(N-hexadecanoyl-cysteine)– PbTx-B |
C71H112N2O18S | 1312.8 | / | Oysters (Crassostrea virginica) | [39] | |
| #87 | Glycine–(N-hydroxy-eicosanoyl)-cysteine-BTX-B | Glycine–(N-hydroxy-eicosanoyl)-cysteine–PbTx-B | C75H120N2O19S | 1384.8 | / | Oysters (Crassostrea virginica) | [39] | |
| #88 | Metabolite not named | / | C52H76O17S | 1004.5 | / | Oysters (Crassostrea virginica) | [30,39] |