Pheromones and Semiochemicals of Alexandrium tamarense (Gonyaulacales: Ostreopsidaceae)

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Semiochemicals of Alexandrium tamarense

Phylum:	Myzozoa
Subphylum:	Dinozoa
Class:	Dinophyceae
Order:	Gonyaulacales
Family:	Ostreopsidaceae
Subfamily:
Genus:	Alexandrium
Tribe:
Author:	Lebour

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Semiochemical(s):

Dell'Aversano C

2008

J. Nat. Prod.

71:

1518

STX

�Relative ratio of the component�

�(*) indicates that compound is active�

P �Category of the chemical signal

A -	Attractant
Al -	Allomone
K -	Kairomone
P -	Pheromone
Sy -	Synomone�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Nova Scotia, Canada

neoSTX

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

GTX 1

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

GTX 2

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

GTX 3

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

GTX 4

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

GTX 5

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

toxin C1

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

toxin C2

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Oikawa H

2004

Toxicon

43:

713

toxin C1

�Relative ratio of the component�

�(*) indicates that compound is active�

P �Category of the chemical signal

A -	Attractant
Al -	Allomone
K -	Kairomone
P -	Pheromone
Sy -	Synomone�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Onahama, Fukushima Prefecture, Japan

toxin C2

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

GTX 1

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

GTX 3

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

GTX 4

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Ichimi K

2002

J. Exp. Mar. Biol. Ecol.

273:

STX

�Relative ratio of the component�

�(*) indicates that compound is active�

P �Category of the chemical signal

A -	Attractant
Al -	Allomone
K -	Kairomone
P -	Pheromone
Sy -	Synomone�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Sendai Bay, Miyagi Prefecture, Japan

neoSTX

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

GTX 1

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

GTX 2

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

GTX 3

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

GTX 4

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

toxin C1

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

toxin C2

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Parkhill J

1999

J. Plankton Res.

21:

939

STX

�Relative ratio of the component�

�(*) indicates that compound is active�

P �Category of the chemical signal

A -	Attractant
Al -	Allomone
K -	Kairomone
P -	Pheromone
Sy -	Synomone�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

St. Lawrence River, Qu�bec, Canada

neoSTX

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

GTX 1

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

GTX 2

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

GTX 3

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

GTX 4

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

toxin C1

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

toxin C2

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Yu R

1998

Chromatographia

48:

671

STX

�Relative ratio of the component�

�(*) indicates that compound is active�

P �Category of the chemical signal

A -	Attractant
Al -	Allomone
K -	Kairomone
P -	Pheromone
Sy -	Synomone�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Tianjing, Rizhao, Jiaozhou, Zhoushan, China

neoSTX

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

GTX 1

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

GTX 2

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

GTX 3

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

GTX 4

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

GTX 5

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

GTX 6

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

toxin C1

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

toxin C2

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Carreto JI

1996

Rev. Invest. Desarr. Pesq.

10:

101

GTX 1

�Relative ratio of the component�

�(*) indicates that compound is active�

P �Category of the chemical signal

A -	Attractant
Al -	Allomone
K -	Kairomone
P -	Pheromone
Sy -	Synomone�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Mar del Plata Coast, Argentina

GTX 2

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

GTX 3

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

GTX 4

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

toxin C1

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

toxin C2

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

neoSTX

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

STX

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

dcGTX 3

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

dcGTX 2

�Relative ratio of the component�

�(*) indicates that compound is active�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Kodama M

1996

Toxicon

34:

1101

TTX

�Relative ratio of the component�

�(*) indicates that compound is active�

P �Category of the chemical signal

A -	Attractant
Al -	Allomone
K -	Kairomone
P -	Pheromone
Sy -	Synomone�

�Source of the chemical signal

F -	Female
H -	Host (could be of plant or animal origin)
L -	Lure
M -	Male
M&F -	Male and Female
S -	Solider
Q -	Queen
W -	Worker�

�Amount

pg -	Picogram
ng -	Nanogram
�g -	Microgram
mg -	Milligram
g -	Gram�

Ofunato Bay, Iwate Prefecture, Japan

Reference(s):

Dell'Aversano, C., Walter, J.A., Burton, I.W., Stirling, D.J., Fattorusso, E., and Quilliam, M.A. 2008. Isolation and structure elucidation of new and unusual saxitoxin analogues from mussels. J. Nat. Prod. 71:1518-1523.

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