Pheromones and Semiochemicals of Gambierdiscus toxicus (Gonyaulacales: Goniodomataceae)

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Semiochemicals of Gambierdiscus toxicus

Phylum:	Mollusca
Subphylum:	Dinozoa
Class:	Dinophyceae
Order:	Gonyaulacales
Family:	Goniodomataceae
Subfamily:	Gambierdiscoideae
Genus:	Gambierdiscus
Tribe:
Author:	Adachi & Fukuyo

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Semiochemical(s):

Watanabe R

2013

Tetrahedron Lett.

54:

10299

gambieroxide

�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�

Papeete, Tahiti, French Polynesia

Yasumoto T

2000

J. Am. Chem. Soc.

122:

4988

P-CTX 3C

�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�

Japan

P-CTX 4A

�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�

P-CTX 4B

�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�

P-CTX 3B

�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�

M-seco-CTX 3C

�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�

M-seco-4-O-methyl-CTX 3C

�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�

M-seco-CTX 4A

�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�

Satake M

1997a

Biosci. Biotechn. Biochem.

60:

2103

P-CTX 4A

�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�

Tuamotu Archipelago, French Polynesia

Satake M

1993b

J. Am. Chem. Soc.

115:

361

gambierol

�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�

Rangiroa Atoll, Tuamotu Archipelago, French Polynesia

Satake M

1993a

Tetrahedron Lett.

34:

1975

P-CTX 3C

�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�

Tuamotu Archipelago, French Polynesia

P-CTX 4B

�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�

Murata M

1992

J. Am. Chem. Soc.

114:

6594

MTX

�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�

Japan

Nagai H

1992

J. Org. Chem.

57:

5448

gambieric acid A

�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�

Japan

gambieric acid B

�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�

gambieric acid C

�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�

gambieric acid D

�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�

Reference(s):

Watanabe, R., Uchida, H., Suzuki, T., Matsushima, R., Nagae, M., Toyohara, Y., Satake, M., Oshima, Y., Inoue, A., and Yasumoto, T. 2013. Gambieroxide, a novel epoxy polyether compound from the dinoflagellate Gambierdiscus toxicus GTP2 strain. Tetrahedron Lett. 54:10299-10303.

Yasumoto, T., Igarashi, T., Legrand, A.-M., Cruchet, P., Chinain, M., Fujita, T., and Naoki, H. 2000. Structural elucidation of ciguatoxin congeners by fast-atom bombardment tandem mass spectroscop. J. Am. Chem. Soc. 122:4988-4989.

Satake, M., Ishibashi, Y., Legrand, A.-M., and Yasumoto, T. 1997a. Isolation and structure of ciguatoxin-4A, a new ciguatoxin precursor, from cultures of dinoflagellate Gambierdiscus toxicus and Parrotfish Scarus gibbus. Biosci. Biotechn. Biochem. 60:2103-2105.

Satake, M., Murata, M., and Yasumoto, T. 1993b. Gambierol: a new toxic polyether compound isolated from the marine dinoflagellate Gambierdiscus toxicus. J. Am. Chem. Soc.115:361-362.

Satake, M., Murata, M., and Yasumoto, T. 1993a. The structure of CTX 3C, a ciguatoxin congener isolated from cultured Gambierdiscus toxicus. Tetrahedron Lett. 34:1975-1978.

Murata, M., Iwashita, T., Yokohama, A., Sasaki, M., and Yasumota, T. 1992. Partial structures of maitotoxin, the most potent marine toxin from dinoflagellate Gambierdiscus toxicus. J. Am. Chem. Soc. 114:6594-6596.

Nagai, H., Murata, M., Torigoe, K., Satake, M., and Yasumoto, T. 1992. Gambieric acids, new potent antifungal substances with unprecedented polyether structures from a marine dinoflagellate Gambierdiscus toxicus. J. Org. Chem. 57:5448-5453.

Citation: El-Sayed AM 2024. The Pherobase: Database of Pheromones and Semiochemicals. <http://www.pherobase.com>.
Ⓒ 2003-2024 The Pherobase - Extensive Database of Pheromones and Semiochemicals. Ashraf M. El-Sayed.
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