Pheromones and Semiochemicals of Aaptos aaptos (Suberitida: Suberitidae), the Okinawan sponge

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Semiochemicals of Aaptos aaptos, the Okinawan sponge

Phylum:	Porifera
Subphylum:
Class:	Demospongiae
Order:	Suberitida
Family:	Suberitidae
Subfamily:
Genus:	Aaptos
Tribe:
Author:	Schmidt

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Distribution: Google

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Semiochemical(s):

Hamada T

2019

NPC

14:

methylenedioxyaaptamine

�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�

Sepanggar Island, Sabah, Borneo, Malaysia

dimethylketal demethyl(oxy)aaptamine

�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�

Utkina NK

2016

NPC

11:

1259

demethylaaptanone

�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�

Tho Chu Island, Vietnam

aaptamine

�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�

isoaaptamine

�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�

9-demethylaaptamine

�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�

aaptanone

�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�

Utkina NK

2009b

Tetrahedron Lett.

50:

2580

aaptanone

�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�

Cu Lao Re Island, Vietnam

aaptamine

�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�

isoaaptamine

�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�

Herlt A

2004

Tetrahedron

60:

6101

bisdemethylaaptamine

�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�

Bunaken Island, Indonesia

bisdemethylaaptamine-9-sulfate

�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�

Coutinho AF

2002

Heterocycles

57:

1265

4me-aaptamine

�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�

Bahia, Brazil

9-demethyloxyaaptamine

�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�

Tinto WF

1998

Heterocycles

48:

2089

aaptosamine

�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�

Rust Bay, Trinidad

9-demethyloxyaaptamine

�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�

Rudi A

1993a

Tetrahedron Lett.

34:

4683

aaptosine

�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�

Red Sea

Kashman Y

1990

New J. Chem.

14:

729

isoaaptamine

�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�

Red Sea

Nakamura H

1987

J. Chem. Soc. Perkin Trans.

173

9-demethylaaptamine

�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�

Okinawa Island, Japan

9-demethyloxyaaptamine

�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�

Nakamura H

1982

Tetrahedron Lett.

23:

5555

aaptamine

�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�

Okinawa Island, Japan

Reference(s):

Hamada, T., Matsumoto, Y., Phan, C.-S., Kamada, T., Onitsuka, S., Okamura, H., Iwagawa, T., Arima, N., Tani, F., and Vairappan, C.S. 2019. Aaptamine-related alkaloid from the marine sponge Aaptos aaptos. NPC. 14:

Utkina, N.K., and Denisenko, V.A. 2016. N-Demethylaaptanone, a new congener of aaptamine alkaloids from the Vietnamese marine sponge Aaptos aaptos. NPC. 11:1259-1260.

Utkina, N.K., Denisenko, V.A., and Pushilin, M.A. 2009b. Aaptanone, a novel zwitterionic metabolite of the aaptamine class with an oxygenated 1,6-naphthyridine core from the Vietnamese marine sponge Aaptos aaptos. Tetrahedron Lett. 50:2580-2582.

Herlt, A., Mander, L., Rombang, W., Rumampuk, R., Soemitro, S., Steglich, W., Tarigan, P., and von Nussbaum, F. 2004 Alkaloids from marine organisms. Part 8: Isolation of bisdemethylaaptamine and bisdemethylaaptamine-9-O-sulfate from an Indonesian Aaptos sp marine sponge. Tetrahedron. 60:6101-6104.

Coutinho, A.F., Chanas, B., Souza, T.M.L., Frugrulhetti, I.C.C.P., and Epifanio, R. 2002. Anti HSV-1 alkaloids from a feeding deterrent marine sponge of the genus Aaptos. Heterocycles. 57:1265-1272.

Tinto, W.F. 1998. Aaptosamine, a new 5,8-diazabenz[cd]azulene alkaloid from the Caribbean sponge Aaptos aaptos. An unprecedented base-catalyzed rearrangement of 9-demethyloxyaaptamine. Heterocycles. 48:2089-2093.

Rudi, A., and Kashman, Y. 1993a. Aaptosine - a new cytotoxic 5,8-diazabenz[cd]azulene alkaloid from the Red sea sponge Aaptos aaptos. Tetrahedron Lett. 34:4683-4684.

Kashman, Y., Rudi, A., Hirch, S., Isaacs, S., Green, D., Blasberger, D., and Carmely, S. 1990. Recent developments in research on metabolites from Red sea invertebrates. New J. Chem. 14:729-740.

Nakamura, H., Kobayashi, J., and Ohizumi, Y. 1987. Aaptamines. Novel benzo[de][1,6]naphthyridines from the Okinawan marine sponge Aaptos aaptos. J. Chem. Soc. Perkin Trans. 1:173-176.

Nakamura, H., Kobayashi, J., Ohizumi, Y., and Hirata, Y. 1982. Isolation and structure of aaptamine a novel heteroaromatic substance possessing a-blocking activity from the sea sponge Aaptos aaptos. Tetrahedron Lett. 23:5555-5558. .

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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