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Semiochemicals of Genus Gambierdiscus

Phylum: Mollusca
Subphylum: Dinozoa
Class: Dinophyceae
Order: Gonyaulacales
Family: Goniodomataceae
Subfamily: Gambierdiscoideae
Tribe: 
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Bedoukain RussellIPM

Semiochemical(s):

Gambierdiscus australes Chinian & Faust
 
               Murray JS  2019  Tetrahedron Lett.  60: 621   
    MTX3    ¦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
µg -   Microgram
mg -   Milligram
g -   Gram¦
   		Kermadec Island, New Zealand 
 
 
Gambierdiscus belizeanus Faust
 
               Rodriguez IS  2015  Org. Lett.  17: 2392   
    gambierone    ¦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
µg -   Microgram
mg -   Milligram
g -   Gram¦
   		Spain 
 
 
Gambierdiscus excentricus Fraga
 
               Yon T  2021  Mar. Drugs  19: 657   
    sulfo-gambierone    ¦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
µg -   Microgram
mg -   Milligram
g -   Gram¦
   		Bahamas & Florida Keys, USA 
    dihydro-sulfo-gambierone    ¦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
µg -   Microgram
mg -   Milligram
g -   Gram¦
   		 
 
               Pisapia F  2017  Mar. Drugs  15: 220   
    MTX4    ¦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
µg -   Microgram
mg -   Milligram
g -   Gram¦
   		France 
 
 
Gambierdiscus toxicus Adachi & Fukuyo
 
               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
µg -   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
µg -   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
µg -   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
µg -   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
µg -   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
µg -   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
µg -   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
µg -   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
µg -   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
µg -   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
µg -   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
µg -   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
µg -   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
µg -   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
µg -   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
µg -   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
µg -   Microgram
mg -   Milligram
g -   Gram¦
   		 
 
 
Reference(s):

Yon, T., Sibat, M., Robert, E., Lhaute, K., Holland, W.C., Litaker, R.W., Bertrand, S., Hess, P., and Réveillon, D. 2021. Sulfo-gambierones, two new analogs of gambierone produced by Gambierdiscus excentricus. Mar. Drugs. 19:657-676.
 
Murray, J.S., Selwood, A.I., Harwood, D.T., van Ginkel, R., Puddick, J., Rhodes, L.L., Rise, F., and Wilkins, A.L. 2019. 44-Methylgambierone, a new gambierone analogue isolated from Gambierdiscus australes. Tetrahedron Lett. 60:621-625.
 
Pisapia, F., Sibat, M., Herrenknecht, C., Lhaute, K., Gaiani, G., Ferron, P.-J., Fessard, V., Fraga, S., Nascimento, S.M., and Litaker, R.W. 2017. Maitotoxin-4, a novel MTX analog produced by Gambierdiscus excentricus. Mar. Drugs. 15:220-250.
 
Rodríguez, I.S., Genta-Jouve, G.G., Alfonso, C., Calabro, K., Alonso, E., Sánchez, J.A., Alfonso, A., Thomas, O.P., and Botana, L.M. 2015. Gambierone, a ladder-shaped polyether from the dinoflagellate Gambierdiscus belizeanus. Org. Lett. 17:2392-2395.
 
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.
Page created on 13-February-2024