Prodigiosin alkaloid

For an excellent review on the chemistry and biology of273 and the related prodigiosin alkaloids, see Fiirstner A (2003) Angew Chem Int Ed 42 3582... 

The deep-red colored prodigiosin alkaloids are endowed with potent antibacterial, cytotoxic, and antimalaria properties. Additionally, in a series of recent reports it has been claimed that this family also displays a significant immunosuppressive activity. This finding is particularly noteworthy since the mechanism of action seems to be distinctly different from that of... 

Chemistry and biology of roseophilin and the prodigiosin alkaloids 03AG(E)3582. 

Heptyl prodigiosin (43) [Fig. (13)] is another antimalarial alkaloid isolated from a tunicate. Precisely, this pigment was purified from a culture of a-proteobacteria isolated from a marine tunicate and showed an antimalarial activity similar to that of quinine against the chloroquine -sensitive strain P. falciparum 3D7 with an in vitro activity that was about 20 times the in vitro cytotoxic activity against mouse lymphocytes. When this molecule was tested in vivo, a single administration of 5 mg/Kg significantly extended the survival of P. berghei ANKA strain-infected mice but, unfortunately, the same dose caused sclerotic lesions at the site of injection [62],... 

In this chapter, prodigiosin, obtained from the cultured broth of Serratia marcescens stachydrine, isolated from Fabaceae plants and pyrrole-2-carboxyUc acid, isolated from the culture broth of Streptomyces sp. No. 82-85 are described. Regarding these alkaloids, it was established that labeled prohne is incorporated into these alkaloids. It was also determined that alanine and glycine are incorporated into prodigiosin, in addition to proline [1]. However, intact incorporation of proline into prodigiosin as a unit retaining the nitrc en atom was observed, and consequendy this alkaloid is described in this chapter. 

Here, these alkaloids will be described in this chapter as alkaloids based on a porphine skeleton. Their biosynthesis is completely different from that of prodigiosin described in the chapter on alkaloids derived from proline (Chapter 5). Total synthesis of chlorophyll a was achieved [2,3], and the assignment of all resonances in the nuclear magnetic resonance (NMR) spectrum of chlorophyll b has been accomplished [4]. Also the biosynthesis and chemistry of the chlorophylls have been reviewed [5—8]. 

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