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