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. Author manuscript; available in PMC: 2013 May 14.
Published in final edited form as: Angew Chem Int Ed Engl. 2012 May 3;51(20):4802–4836. doi: 10.1002/anie.201107204

Table 10.

Enantiomeric manzamine alkaloids.

Manzamine Species Biological Activity
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(+)-8-hydroxymanzamine A		 Indonesian sponge Pachypellina sp.,[187] Okinawan sponge Xestospongia sp.,[188] Okinawan sponge Amphimedon sp.[188] Anticancer[183]
(−)-8-hydroxymanzamine A Unidentified Indo-Pacific sponge (family Petrosiidae, order Haplosclerida)[189] Anticancer,[183] Antimalarial[183]
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(+)-manzamine F		 Xestospongia sp.[190] Antimicrobial,[183] Anticancer[183]
(−)-manzamine F Unidentified Indo-Pacific sponge (family Petrosiidae, order Haplosclerida)[189] Activity against Mycobacterium tuberculosis[183]
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(±) keramaphidin B		 Amphimedon sp.,[191] Xestospongia ingens [optically active, [α]D +29.8° (c 1.1; MeOH)][192] Anticancer[183]