Manzamines biogenesis

Biogenesis of manzamine alkaloids ((3-carboline marine alkaloids) 97H(46)765, 97YGK1114. 

The motuporamines are considered as manzamine-related alkaloids owing to their structural relationship with manzamine C (57), the simplest alkaloid of this family of compounds. Baldwin and Whitehead have proposed a plausible biogenesis for these 3-alkylpiperidine alkaloids, suggesting that they could be formed from three basic building blocks ammonia, a C3 unit, and a Cio unit [54]. The motuporamines, which contain a spermidine-like side chain instead of the alkylated p-carboline substructure of manzamine C, appear to be biogenetically derived from the same precursors, ammonia, acrolein, and a long-chain dialdehyde involved in the Baldwin-Whitehead pathway (Scheme 9.2). 

A proposed biogenesis for the formation of monomeric, dimeric and oligomeric 3-alkylpiperidine alkaloids. The proposal is based on Baldwin and Whitehead s proposed biogenesis for the manzamines [58]. 

As outlined above, the Baldwin and Whitehead proposal for the biogenesis of the manzamines has provided a mechanistic framework that can be used to formulate rather detailed step by step hypotheses for the formation of all known 3-alkylpiperidine alkaloids. Figure 3.11 shows an overall scheme for the biogenesis of the 3-alkylpiperidine alkaloids that incorporates elements of all of the individual proposals that have been put forth to date. 

Fig (4). Baldwin Etnd Withehead proposed biogenesis path for the manzamine alkaloids... 

Scheme 1. The Baldwin-Whitehead hypothesis for the biogenesis of manzamine B (2) and related alkaloids.

Biogenesis of manzamine alkaloids 0-carbohne marine alkaloids) 97YGK1114. 

Structure and biogenesis of manzamines and related alkaloids (review). Tsuda, M., Kobayashi, J. (1997), 46, 765-794. 

Figure 19.80 Biogenesis of manzamines A-C (according to Baldwin and Whitehead, 1992).

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