Just look at the structure of this alkaloid!

Sometimes you just have to step back and marvel at the structures that are found in nature.  Check out zamamiphidin A, a new manzamine alkaloid isolated from an Okinawan sponge by J. Kobayashi and co-workers (Organic Letters).  Heptacyclic.  Quaternary ammonium.  Massively bridged.  Well done, sponges!

Zamamiphidin A

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7 responses to “Just look at the structure of this alkaloid!”

  1. DrFreddy says :


    I wonder if you would take out your mercury lamp and shine on it — would it be possible to bridge it even further via an internal [2+2]?

    Then ponder over the correct IUPAC name for the desired product.

    • Will says :

      That would be diabolical. As would the name. I notice the authors didn’t tackle the nomenclature issue. I guess it will be up to someone at CAS when it gets abstracted!

  2. nitrosonium says :

    i have wondered for years……why do so many biologically interesting structures of such molecular complexity come (apparently more often) from sponges?? i realize there’s tons of heterocycle diversity/complexity in nature but it seems like a disproportionate number of reports describe sponges as the source for the new yet-to-be-synthesized alkaloid.

    • Will Pearson says :

      I guess when you’re firmly attached to a rock, unable to run from things that want to eat you, you have plenty of time to try new things to defend yourself. Nothing better to do!

      • milkshake says :

        plus they get colonized by symbiotic bacteria who are waging chemical warfare against other organisms – this has been apparently going on for long time – multicelular organisms existed in oceans for about 1 billion years, single-cell based ones for at least 3 times as long

  3. Dave says :

    Of course, the structure needs to be correct to be that impressive.

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