Marine-derived macrocyclic alkaloids.
Althagbi HI, Alarif WM, Al-Footy KO, Abdel-Lateff A. Marine-Derived Macrocyclic Alkaloids (MDMAs): Chemical and Biological Diversity. Mar Drugs.2020 18(7):E368. PMID: 3270904
Subclasses Name of Compounds Marine Organism Biological Activities
Pyrroles Densanins A and B Haliclona densaspicula Anti-inflammatory
Quinolines Njaoamines A–F Reniera sp. Cytotoxic and
Njaoamines G–H Neopetrosia sp. Anti-HIV
Njaoamine I Reniera sp.
Bis-Quinolizidines Petrosin Petrosia seriata
Petrosins A and B
Aragupetrosine A Xestospongia sp.
Xestosin A Xestospongia exigua
Xestospongin A (Araguspongine D)
Xestospongin B
Xestospongin C (Araguspongine E)
Xestospongin D (Araguspongine A) Xestospongia sp.
Xestospongins J Oceanapia sp.
(+)-7S-Hydroxyxestospongin A Xestospongia sp.
Demethylxestospongin B Xestospongia sp.
3β,3ʹβ-Dimethylxestospongin C and
9′-epi-3β,3′β–Dimethyl-xestospongin C Neopetrosia exigua
Araguspongine B Antimicrobial and Cytotoxic
Araguspongine C Xestospongia muta
Araguspongines F–H and J Xestospongia sp.
3a-Araguspongin C Haliclona exigua
Araguspongines K and L Neopetrosia exigua
Araguspongine M
Araguspongines N–P Xestospongia muta
meso-araguspongine C
3-Alkyl piperidines Saraines 1–3 Reniera sarai Cytotoxic
Isosaraines 1–3 Antimicrobial
Saraines A-C
Madangamines A–E Xestospongia ingens Cytotoxic
Madangamine F Pachychalina alcaloidifera
(10E,12Z)-haliclonadiamine Halichondria panicea Antimicrobial
(10Z,12E)-Haliclonadiamine Halichondria panacea
Papuamine Haliclona sp.
Haliclonadiamine Haliclona sp.
Ingamines A and B Xestospongia ingens Antimalarial
Ingenamine
Ingenamines B–F
Ingenamine G Pachychalina sp.
Dihydroingenamine D Petrosid Ng5 Sp5
22(S)-Hydroxyingamine A
Xestocyclamine Xestospongia sp. protein kinase C inhibitor
Halicyclamines A-B Xestospongia sp. Cytotoxic
Haliclonacyclamines A–B Haliclona sp.
22-Hydroxyhaliclon-acyclamine B Halichondria sp.
2-epi-Tetradehydro-haliclonacyclamine Halichondria sp.
Tetradehydrohaliclonacyclamine A mono-N-oxide Halichondria sp.
Tetradehydrohaliclonacyclamine A Halichondria sp.
Haliclonacyclamine C Haliclona sp.
Haliclonacyclamine D Haliclona sp.
Haliclonacyclamine E Arenosclera brasiliensis Antimalarial,
Haliclonacyclamine F P. alcaloidifera Cytotoxic,
Halichondramine Halichondria sp. Proteasome and Immunoproteasome inhibition
Neopetrosiamine A Neopetrosia proxima
Tetradehydrohali-cyclamine B Acanthostrongylophora ingens
Arenosclerins A–C A. brasiliensis Cytotoxic,
Arenosclerins D and E P. alcaloidifera Anti-leishmanial,
Manzamines Manzamine A (Keramamine A) Haliclona sp. and Anti-HIV
8-Hydroxymanzamine A (Manzamine G) Amphimedon sp. and Pachypellina sp.
3,4-Dihydromanzamine A Amphimedon sp.
6-Hydroxymanzamine A (Manzamine Y) Amphimedon sp. and Haliclona sp.
1,2,3,4-Tetrahydro-8-hydroxymanza-mine A Cribochalina sp. and Petrosia sp.
(8-Hydroxymanzamine D)
1,2,3,4-Tetrahydro-2-N-methyl-8-hyd-roxymanzamine A (8-Hydroxy-2-N-methylmanzamine D)
Manzamine D (1,2,3,4-Tetrahydromanzamine A) Ircinia sp.
3,4-Dihydro-6-hydroxymanzamine A Amphimedon sp.
Manzamine M
N-Methyl-epi-manzamine D Unidentified Paluan sponge
epi-Manzamine D
12,34-Oxamanzamine A Sponge 011ND 35
ent-8-Hydroxymanzamine A Unidentified Indo-Pacific sponge
12,28-Oxamanzamine A Acanthostrongylophora sp.
12,28-Oxa-8-hydroxymanzamine A
Manzamine A N-oxide Xestospongia ashmorica
3,4-Dihydromanzamine A N-oxide
Acanthomanzamines A and B Acanthostrongylophora sp.
Pre-neo-kauluamine Acanthostrongylophora ingens
Zamamidine C Amphimedon sp.
Zamamidine D
Nakadomarin A
Ircinol A
Ircinal A Ircinia sp.
Ircinal E
12,28-Oxaircinal A
Manzamine E Xestospongia sp.
Manzamine F (Keramamine B)
ent-Manzamine F
ent-12,34-Oxamanzamines E and F Sponge 011ND 35
12,34-Oxamanzamine E Acanthostrongylophora sp.
6-Hydroxymanzamine E
12,28-Oxamanzamine E
12,34-Oxa-6-hydroxymanzamine E
31-Keto-12,34-oxa-32,33-dihydroircinal A
Manzamine B Haliclona sp.
Manzamines H, J Ircinia sp.
Manzamine J N-oxide Xestospongiaashmorica
8-Hydroxymanzamine B Acanthostrongylophora sp.
Manzamine L Amphimedon sp.
Manzamine B N-oxide Acanthostrongylophora sp.
3,4-Dihydromanzamine B N-oxide
11-Hydroxymanzamine J
Ma’eganedin A Amphimedon sp.
8-Hydroxymanzamine J Acanthostrongylophora
3,4-Dihydromanzamine J Amphimedon sp.
Acanthomanzamines D and E Acanthostrongylophora sp.
Zamamidines A and B Amphimedon sp.
Ircinal B Ircinia sp.
Ircinol B Amphimedon sp.
Manzamine C Haliclona sp. Cytotoxic
Keramamine C Amphimedon sp.
Acanthomanzamine C Acanthostrongylophora sp.
Kepulauamine A
Acantholactam
Acantholactone Acanthostrongylophora sp.
32,33-Dihydro-31-hydroxymanzamine A Indonesian sponge
32,33-Dihydro-6-hydroxymanzamine A-35-one
32,33-Dihydro-6,31-dihydroxymanzamine A
Manzamine X Xestospongia sp.
6-Deoxymanzamine X X. ashmorica
Manadomanzamines A and B Acanthostrongylophora sp.
Keramaphidin B Amphimedon sp.
Kauluamine Prianos sp.
3-Alkyl pyridinium salts Cyclostellettamines A–F Stelletta maxima Antimicrobial and
Cyclostellettamines G–I, K, and L Pachychalina sp. Cytotoxic
Dehydrocyclostellettamines D, E Xestospongia sp.
8,8‘-Dienecyclostellettamine Amphimedon compressa
Cyclostellettamines N, R, O, Q Haliclona sp.
Cyclostellettamines Haliclona sp.
Cyclostellettamine P Xestospongia exigua
Njaoaminiums A–C Reniera sp. Cytotoxic
Motuporamines Motuporamines A–I Xestospongia exigua Anti-invasion
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