Neurotoxic Alkaloids: Saxitoxin and Its Analogs

Maria Wiese; Paul M. D’Agostino; Troco K. Mihali; Michelle C. Moffitt; Brett A. Neilan

doi:10.3390/md8072185

Table 1

The paralytic shellfish toxins.


Toxin	R1	R2	R3	^Ω R4	R5	Origin	Ref.
STX	H	H	H	OCONH₂	OH	Alexandrium andersoni	[46]
						A. catenella	[47–49]
						A. fundyense	[50–52]
						A. tamarense	[53–56]
						A. circinalis	[35,57–59]
						Aphanizomenon flos-aquae	[60–63]
						Aph. gracile	[20,64]
						Aph. issatschenkoi	[65]
						Anabaena lemmermannii	[66]
						C. raciborskii	[16,36,67–69]
						Gymnodinium catenatum	[70–72]
						Pyrodinium bahamense	[10]
						Planktothrix sp.	[73]
neoSTX	OH	H	H	OCONH₂	OH	A. andersoni	[46]
						A. catenella	[47–49]
						A. fundyense	[50–52]
						A. tamarense	[53–56]
						Aph. flos-aquae	[60–63]
						Aph. gracile	[20,64]
						Aph. issatschenkoi	[65]
						Aph. sp.	[74]
						C. raciborskii	[16,36,69]
						G. catenatum	[70,71]
						P. bahamense	[10]

Mono-Sulfated
GTX1	OH	H	OSO₃⁻	OCONH₂	OH	A. catenella	[47–49,75,76]
						A. fundyense	[50–52]
						A. minutum	[77–79]
						A. tamarense	[53–56]
						Aph. flos-aquae	[37]
						G. catenatum	[9,70,72]
GTX2	H	H	OSO₃⁻	OCONH₂	OH	A. catenella	[48,49]
						A. fundyense	[50–52]
						A. minutum	[77–79]
						A. ostenfeldii	[80]
						A. tamarense	[53–56]
						A. circinalis	[35,57–59]
						C. raciborskii	[36,67]
						G. catenatum	[9,70,72]
GTX3	H	OSO₃⁻	H	OCONH₂	OH	A. catenella	47–49]
						A. fundyense	[50–52]
						A. minutum	[77–79]
						A. ostenfeldii	[80]
						A. tamarense	[53–56]
						A. circinalis	[35,57–59]
						Aph. flos-aquae	[37]
						C. raciborskii	[36,67]
						G. catenatum	[9,70,72]
GTX4	OH	OSO₃⁻	H	OCONH₂	OH	A. catenella	[47–49,75,76]
						A. fundyense	[50–52]
						A. minutum	[77–79]
						A. tamarense	[53–56]
						Aph. flos-aquae	[37]
						G. catenatum	[9,70,72]
GTX5 (B1)	H	H	H	OCONHSO₃⁻	OH	A. catenella	[48,49,75,76]
						A. fundyense	[50–52]
						A. tamarense	[54,56]
						A. circinalis	[35,57,59]
						Aph. flos-aquae	[60,63]
						Aph. gracile	[20]
						Aph. issatschenkoi	[37,65]
						G. catenatum	[9,71,81]
						P. bahamense	[10]
GTX6 (B2)	OH	H	H	OCONHSO₃⁻	OH	A. catenella	[47,49,75,76]
						A. fundyense	[52]
						A. ostenfeldii	[80]
						A. tamarense	[54]
						Aph. flos-aquae	[63]
						C. raciborskii	[69]
						G. catenatum	[9,71,72,81]
						P. bahamense	[10]

Di-Sulfated
C1	H	H	OSO₃⁻	OCONHSO₃⁻	OH	A. catenella	[48,49,75,76]
						A. fundyense	[50–52]
						A. ostenfeldii	[80]
						A. tamarense	[53–56]
						A. circinalis	[35,57–59]
						C. raciborskii	[68]
						G. catenatum	[9,71,72,81]
C2	H	OSO₃⁻	H	OCONHSO₃⁻	OH	A. catenella	[48,49,75]
						A. fundyense	[50–52]
						A. ostenfeldii	[80]
						A. tamarense	[53–56]
						A. circinalis	[35,57–59]
						C. raciborskii	[68]
						G. catenatum	[9,71,72,81]
C3	OH	H	OSO₃⁻	OCONHSO₃⁻	OH	A. catenella	[48,49,75,76]
						G. catenatum	[9,72,81]
C4	OH	OSO₃⁻	H	OCONHSO₃⁻	OH	A. catenella	[48,49,75,76]
						G. catenatum	[9,72,81]

Decarbamoylated
dcSTX	H	H	H	OH	OH	A. catenella	[49]
						A. circinalis	[35,59]
						Aph. flos-aquae	[60,63]
						Aph. gracile	[20]
						Aph. issatschenkoi	[65]
						Aph. sp.	[74]
						C. raciborskii	[16,67,69]
						Lyngbya wollei	[82]
						G. catenatum	[9,71,72]
						P. bahamense	[10]
dcneoSTX	OH	H	H	OH	OH	C. raciborskii	[69]
dcGTX1	OH	H	OSO₃⁻	OH	OH	G. catenatum	[83]
dcGTX2	H	H	OSO₃⁻	OH	OH	A. catenella	[49]
						A. fundyense	[52]
						A. circinalis	[35,57–59]
						G. catenatum	[9,71]
						L. wollei	[14,82]
dcGTX3	H	OSO₃⁻	H	OH	OH	A. catenella	[49]
						A. fundyense	[50,52]
						A. circinalis	[35,57–59]
						Aphanizomenon sp.	[74]
						L. wollei	[14,82]
						G. catenatum	[9,71]
dcGTX4	OH	OSO₃⁻	H	OH	OH	G. catenatum	[83]

Deoxy-Decarbomoylated
doSTX	H	H	H	H	OH	G. catenatum	[9,84]
doGTX1	OH	H	OSO₃⁻	H	OH	G. catenatum	[9,84]
doGTX2	H	H	OSO₃⁻	H	OH	G. catenatum	[9,84]

**L. wolleitoxins**
LWTX1	H	H	OSO₃⁻	OCOCH₃	H	L. wollei	[82]
LWTX2	H	H	OSO₃⁻	OCOCH₃	OH	L. wollei	[82]
LWTX3	H	OSO₃⁻	H	OCOCH₃	OH	L. wollei	[82]
LWTX4	H	H	H	H	H	L. wollei	[82]
LWTX5	H	H	H	OCOCH₃	OH	L. wollei	[82]
LWTX6	H	H	H	OCOCH₃	H	L. wollei	[82]

Mono-Hydroxy-Benzoate Analogs
GC1	H	H	OSO₃⁻	OCOPhOH	OH	G. catenatum	[83]
GC2	H	OSO₃⁻	H	OCOPhOH	OH	G. catenatum	[83]
GC3	H	H	H	OCOPhOH	OH	G. catenatum	[83]
^*GC4	OH	H	OSO₃⁻	OCOPhOH	OH	G. catenatum	[85]
^*GC5	OH	OSO₃⁻	H	OCOPhOH	OH	G. catenatum	[85]
^*GC6	OH	H	H	OCOPhOH	OH	G. catenatum	[85]

Di-Hydroxy Benzoate Analogs
^ŧGC1a	H	H	OSO₃⁻	DHB	OH	G. catenatum	[85]
^ŧGC2a	H	OSO₃⁻	H	DHB	OH	G. catenatum	[85]
^ŧGC3a	H	H	H	DHB	OH	G. catenatum	[85]
^ŧGC4a	OH	H	OSO₃⁻	DHB	OH	G. catenatum	[85]
^ŧGC5a	OH	OSO₃⁻	H	DHB	OH	G. catenatum	[85]
^ŧGC6a	OH	H	H	DHB	OH	G. catenatum	[85]

Sulfated Benzoate Analogs
^ŧGC1b	H	H	OSO₃⁻	SB	OH	G. catenatum	[85]
^ŧGC2b	H	OSO₃⁻	H	SB	OH	G. catenatum	[85]
^ŧGC3b	H	H	H	SB	OH	G. catenatum	[85]
^ŧGC4b	OH	H	OSO₃⁻	SB	OH	G. catenatum	[85]
^ŧGC5b	OH	OSO₃⁻	H	SB	OH	G. catenatum	[85]
^ŧGC6b	OH	H	H	SB	OH	G. catenatum	[85]

Other PST Analogs
M1	H	OH	H	OCONHSO₃⁻	OH	Metabolic transformation	[56,81]
M2	H	OH	H	OCONH₂	OH	Metabolic transformation	[56]
M3	H	OH	OH	OCONHSO₃⁻	OH	Metabolic transformation	[56]
M4	H	OH	OH	OCONH₂	OH	Metabolic transformation	[56]
^*M5						Metabolic transformation	[56]
^*A						Unknown	[86]
^*B						Unknown	[86]
^*C						Unknown	[86]
^*D						Unknown	[86]
SEA	H	CCOO⁻	H	OCONH₂	OH	Atergatis floridus	[87]
STX-uk	H	H	H	OCONHCH₃	OH	Tetraodon cutcutia	[88]
Zetekitoxin AB						Atelopus zeteki	[89]

^*Not structurally characterized

^ŧR₄ group putatively assigned based on major ions obtained via MS [85]

^ΩOCONH₂

An external file that holds a picture, illustration, etc.
Object name is marinedrugs-08-02185f5.jpg

^ΩOCONHSO₃⁻

An external file that holds a picture, illustration, etc.
Object name is marinedrugs-08-02185f6.jpg

^ΩOCOCH₃

An external file that holds a picture, illustration, etc.
Object name is marinedrugs-08-02185f7.jpg

^ΩOCOPhOH

An external file that holds a picture, illustration, etc.
Object name is marinedrugs-08-02185f8.jpg

^ΩOCONHCH₃

An external file that holds a picture, illustration, etc.
Object name is marinedrugs-08-02185f9.jpg

^ΩDHB: Di-hydroxyl-benzoate

^ΩSB: Sulfated-benzoate