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Semiochemicals of Genus Karenia

Phylum: Myzozoa
Subphylum: Dinozoa
Class: Dinophyceae
Order: Gymnodiniales
Family: Kareniaceae
Subfamily: 
Tribe: 
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Bedoukain RussellIPM

Semiochemical(s):

Karenia brevisulcata Chang
 
               Satake M  2021  Toxins  13: 82   
    KBT-A1    ¦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¦
   		Wellington Harbour, New Zealand 
    KBT-A2    ¦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  2018  Heterocycles  96: 2096   
    KBT-H    ¦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¦
   		Wellington Harbour, New Zealand 
    KBT-I    ¦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¦
   		 
    KBT-G    ¦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¦
   		 
 
               Irie R  2016  Heterocycles  92: 45   
    BSX-2    ¦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¦
   		Wellington Harbour, New Zealand 
    BSX-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
µg -   Microgram
mg -   Milligram
g -   Gram¦
   		 
    BSX-7    ¦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¦
   		 
    BSX-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
µg -   Microgram
mg -   Milligram
g -   Gram¦
   		 
    BSX-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
µg -   Microgram
mg -   Milligram
g -   Gram¦
   		 
 
               Suzuki R  2014  Org. Lett.  16: 5850   
    BSX-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
µg -   Microgram
mg -   Milligram
g -   Gram¦
   		Wellington Harbour, New Zealand 
    BSX-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
µg -   Microgram
mg -   Milligram
g -   Gram¦
   		 
 
               Hamamoto Y  2012  J. Am. Chem. Soc.  134: 4963   
    KBT-F    ¦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¦
   		Wellington Harbour, New Zealand 
 
               Shi F  2012  Thesis Uni. Lincoln  : 1   
    BSX-3    ¦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¦
   		Wellington Harbour, New Zealand 
    BSX-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
µg -   Microgram
mg -   Milligram
g -   Gram¦
   		 
    BSX-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
µg -   Microgram
mg -   Milligram
g -   Gram¦
   		 
    BSX-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
µg -   Microgram
mg -   Milligram
g -   Gram¦
   		 
    BSX-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
µg -   Microgram
mg -   Milligram
g -   Gram¦
   		 
 
               Holland PT  2012  Harmful Algae  13: 47   
    KBT-F    ¦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¦
   		Wellington Harbour, New Zealand 
    KBT-G    ¦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¦
   		 
    BSX-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
µg -   Microgram
mg -   Milligram
g -   Gram¦
   		 
    BSX-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
µg -   Microgram
mg -   Milligram
g -   Gram¦
   		 
    BSX-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
µg -   Microgram
mg -   Milligram
g -   Gram¦
   		 
    BSX-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
µg -   Microgram
mg -   Milligram
g -   Gram¦
   		 
 
 
Karenia mikimotoi Miyake, Kominami & Oda
 
               Tanaka Y  2013  Heterocycles  87: 2037   
    gymnocin A carboxylic acid    ¦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¦
   		Kushimoto Bay, Wakayama, Japan 
    gymnocin A2    ¦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¦
   		 
 
               Tsukano C  2006  Tetrahedron Lett.  47: 6803   
    gymnocin 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 
 
               Satake M  2005  Tetrahedron Lett.  46: 3537   
    gymnocin B    ¦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¦
   		Kushimoto Bay, Wakayama, Japan 
 
               Satake M  2002  Tetrahedron Lett.  43: 5829   
    gymnocin 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¦
   		Kushimoto Bay, Wakayama, Japan 
 
 
Karenia selliformis Haywood
 
               Miles CO  2003  J. Agric. Food Chem.  51: 4838   
    GYM-C    ¦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¦
   		Foveaux Strait, New Zealand 
    GYM-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¦
   		 
 
               Miles CO  2000  J. Agric. Food Chem.  48: 1373   
    GYM-B    ¦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¦
   		Foveaux Strait, New Zealand 
 
 
Reference(s):

Satake, M., Irie, R., Holland, P.T., Harwood, D.T., Shi, F., Itoh, Y., Hayashi, F., and Zhang, H. 2021. Brevisulcenals-A1 and A2, sulfate esters of brevisulcenals, isolated from the red tide dinoflagellate Karenia brevisulcata. Toxins. 13:82-91.
 
Satake, M., Irie, R., Hamamoto, Y., Tachibana, K., Holland, P.T., Harwood, D.T., Shi, F., Beuzenberg, V., Itoh, Y., Hayashi, F., and Zhang, H.-P. 2018. Brevisulcenal-G, -H, and -I, polycyclic ether marine toxins from the dinoflagellate Karenia brevisulcata. Heterocycles. 96:2096-2105.
 
Irie, R., Suzuki, R., Tachibana, K., Holland, P.T., Harwood, D.T., Shi, F., McNabb, P., Beuzenberg, V., Hayashi, F., Zhang, H., and Satake, M. 2016. Brevisulcatic acids from a marine microalgal species implicated in a toxic event in New Zealand. Heterocycles. 92:45-54.
 
Suzuki, R., Irie, R., Harntaweesup, Y., Tachibana, K., Holland, P.T., Harwood, D.T., Shi, F., Beuzenberg, V., Itoh, Y., Pascal, S., Edwards, P.J.B., and Satake, M. 2014. Brevisulcatic acids, marine ladder-frame polyethers from the red tide dinoflagellate Karenia brevisulcata in New Zealand. Org. Lett. 16:5850-5853.
 
Tanaka, Y., Satake, M., Yotsu-Yamashita, M., and Oshima, Y. 2013. Gymnocin-A carboxylic acid and gymnocin-A2, cytotoxic polyethers from the red tide dinoflagellate Karenia mikimotoi. Heterocycles. 87:2037-2046.
 
Hamamoto, Y., Tachibana, K., Holland, P.T., Shi, F., Beuzenberg, V., Itoh, Y., and Statake, M. 2012. Brevisulcenal-F: a polycyclic ether toxin associated with massive fish-kills in New Zealand. J. Am. Chem. Soc. 134:4963-4968.
 
Holland, P.T., Shi, F.,; Satake, M., Hamamoto, Y., Ito, E., Beuzenberg, V., McNabb, P., Munday, R., Briggs, L., Truman, P., Gooneratne, R., Edwards, P., and Pascal, S.M. 2012. Novel toxins produced by the dinoflagellate Karenia brevisulcata. Harmful Algae. 13:47-57.
 
Shi, F. 2012. Chemical and toxicological investigation of the toxic dinoflagellate, Karenia brevisulcata; Thesis Uni. Lincoln. :1.
 
Tsukano, C., and Sasaki, M. 2006. Structure–activity relationship studies of gymnocin-A. Tetrahedron Lett. 47:6803-6807.
 
Satake, M., Tanaka, Y., Ishikura, Y., Oshima, Y., Naoki, H., and Yasumoto, T. 2005. Gymnocin-B with the largest contiguous polyether rings from the red tide dinoflagellate, Karenia (formerly Gymnodinium) mikimotoi. Tetrahedron Lett. 46:3537-3540.
 
Miles, C.O., Wilkins, A.L., Stirling, D.J., and MacKenzie, A.L. 2003. Gymnodimine C, an isomer of gymnodimine B, from Karenia selliformis. J. Agric. Food Chem. 51:4838-4840.
 
Satake, M., Shoji, M., Oshima, Y., Naoki, H., Fujita, T., and Yasumoto, T. 2002. Gymnocin-A, a cytotoxic polyether from the notorious red tide dinoflagellate, Gymnodinium mikimotoi. Tetrahedron Lett. 43:5829-5832.
 
Miles, C.O., Wilkins, A.L., Stirling, D.J., and MacKenzie, A.L. 2000. New analogue of gymnodimine from a Gymnodinium species. J. Agric. Food Chem. 48:1373-1376.
 

 
Citation: El-Sayed AM 2025. The Pherobase: Database of Pheromones and Semiochemicals. <http://www.pherobase.com>.
Ⓒ 2003-2025 The Pherobase - Extensive Database of Pheromones and Semiochemicals. Ashraf M. El-Sayed.
Page created on 19-January-2025