Pheromones and Semiochemicals of Amphimedon sp (Haplosclerida: Niphatidae)

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Semiochemicals of Amphimedon sp

Phylum:	Porifera
Subphylum:
Class:	Demospongiae
Order:	Haplosclerida
Family:	Niphatidae
Subfamily:
Genus:	Amphimedon
Tribe:
Author:	Duchassaing & Michelotti

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Semiochemical(s):

Campos PE

2017b

Tetrahedron Lett.

58:

3901

amphimedonoic 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
�g -	Microgram
mg -	Milligram
g -	Gram�

Mitsio Island, Madagascar

psammaplysene E

�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�

3,5-dibromo-4-methoxybenzoic acid

�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�

Kubota T

2017

J. Nat. Prod.

80:

1196

zamamidine D

�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�

Zamami-jima, Okinawa, Japan

Sakurada T

2010

J. Med. Chem.

53:

6089

1me9me-8-oxoisoguanine

�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�

Republic of Palau

1me3me-8-oxoisoguanine

�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�

3me9me-8-oxoisoguanine

�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�

9me-8-oxoisoguanine

�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�

Takekawa Y

2006

J. Nat. Prod.

69:

1503

amphimedoside 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�

Hachijo Island, Japan

amphimedoside 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�

amphimedoside 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�

amphimedoside 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�

amphimedoside E

�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�

Emura C

2005

J. Org. Chem.

70:

3031

amphimelibioside 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�

Orono Island, Fukuoka Prefecture, Japan

amphimelibioside 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�

amphimelibioside 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�

amphimelibioside 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�

amphimelibioside E

�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�

amphimelibioside F

�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�

Tsukamoto S

2000

J. Nat. Prod.

63:

682

hachijodine E

�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�

Hachijo-jima Island, Japan

hachijodine F

�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�

hachijodine 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
�g -	Microgram
mg -	Milligram
g -	Gram�

Tsuda M

1999c

Heterocycles

50:

485

1,2,3,4-tetrahydromanzamine 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
�g -	Microgram
mg -	Milligram
g -	Gram�

Okinawa Island, Japan

Ovenden SPB

1999a

J. Org. Chem.

64:

1140

amphilactam 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�

Great Australian Bight, Australia

amphilactam 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�

amphilactam 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�

amphilactam 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�

Watanabe D

1998

J. Nat. Prod.

61:

689

manzamine M

�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�

Kerama Island, Okinawa, Japan

3,4-dihydromanzamine J

�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�

3,4-dihydro-6-hydroxymanzamine A

�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�

Nemoto T

1997

Tetrahedron

53:

16699

amphimic 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�

Great Barrier Reef, Australia

amphimic 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�

amphimic 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�

Tsuda M

1997

Heterocycles

46:

765

keramaphidin 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
�g -	Microgram
mg -	Milligram
g -	Gram�

Kise, Okinawa, Japan

keramaphidin 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�

ircinol A

�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�

ircinol 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�

keramamine 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�

manzamine L

�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�

manzamine Y

�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�

3,4-dihydromanzamine A

�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�

keramamine A

�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�

manzamine 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�

manzamine 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�

manzamine 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�

manzamine H

�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�

ircinal A

�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�

ircinal 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�

manzamine 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
�g -	Microgram
mg -	Milligram
g -	Gram�

Tsuda M

1994a

Tetrahedron Lett.

35:

4387

keramaphidin 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
�g -	Microgram
mg -	Milligram
g -	Gram�

Kerama Island, Okinawa, Japan

keramamine 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�

Schmitz FJ

1983a

J. Am. Chem. Soc.

105:

4835

amphimedine

�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�

Guam Island

Reference(s):

Campos, P.-E., Wolfender, J.-L., Queiroz, E.F., Marcourt, L., Al-Mourabit, A., e Voogd, N.J., Illien, B., and Gauvin-Bialecki, A. 2017b. Amphimedonoic acid and psammaplysene E, novel brominated alkaloids from Amphimedon sp. Tetrahedron Lett. 58:3901-3904.

Kubota, T., Nakamura, K., Kurimoto, S.-I., Sakai, K., Fromont, J., Gonoi, T., and Kobayashi, J. 2017. Zamamidine D, a manzamine alkaloid from an Okinawan Amphimedon sp. marine sponge. J. Nat. Prod. 80:1196-1199.

Sakurada, T., Gill, M.B., Frausto, S., Copits, B., Noguchi, K., Shimamoto, K., Swanson, G.T., and Sakai, R. 2010. Novel N-methylated 8-oxoisoguanines from pacific sponges with diverse neuroactivities. J. Med. Chem. 53:6089-6099.

Takekawa, Y., Matsunaga, S., van Soest, R.W.M., and Fusetani, N. 2006. Amphimedosides, 3-alkylpyridine glycosides from a marine sponge Amphimedon sp. J Nat Prod. 69:1503-1505.

Emura, C., Higuchi, R., and Miyamoto, T. 2005. Amphimelibiosides A-F, six new ceramide dihexosides isolated from a Japanese marine sponge Amphimedon sp. J. Org. Chem. 70:3031-3038.

Tsukamoto, S., Takahashi, M., Matsunaga, S., Fusetani, N., and van Soest, R.W.M. 2000. Hachijodines A-G: seven new cytotoxic 3-alkylpyridine alkaloids from two marine sponges of the genera Xestospongia and Amphimedon. J. Nat. Prod. 63:682-684.

Tsuda, M., Watanabe, D., and Kobayashi, J. 1999c. A new manzamine congener from marine sponge Amphimedon sp. Heterocycles. 50:485-488.

Ovenden, S.P.B., Capon, R.J., Lacey, E., Gill, J.H., Friedel, T., and Wadsworth, D. 1999a. Amphilactams A-D: novel nematocides from southern Australian marine sponges of the genus Amphimedon. J. Org. Chem. 64:1140-1144.

Watanabe, D., Tsuda, M., and Kobayashi, J. 1998. Three new manzamine congeners from Amphimedon sponge. J. Nat. Prod. 61:689-692.

Nemoto, T., Yoshino, G., Ojika, M., and Sakagami, Y. 1997. Amphimic acids and related long-chain fatty acids as DANN topoisomerase I inhibitors from an Australian sponge, Amphimedon sp.: isolation, structure, synthesis, and biological evaluation. Tetrahedron. 53:16699-16710.

Tsuda, M., and Kobayashi, J. 1997. Structures and biogenesis of manzamines and related alkaloids. Heterocycles. 46:765-794.

Tsuda, M., Kawasaki, N., and Kobayashi, J. 1994a. Keramaphidin C and keramamine C, plausible biogenetic precursors of manzamine C from an Okinawan marine sponge. Tetrahedron Lett. 35:4387-4388.

Schmitz, F.J., Agarwal, S.K., Gunasekera, S.P., Schmidt, P.G., and Shoolery, J.N. 1983a. Amphimedine, new aromatic alkaloid from a Pacific sponge, Amphimedon sp. carbon connectivity determination from natural abundance 13C-13C coupling constants. J. Am. Chem. Soc. 105:4835-4836.

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