Polyamine alkaloids

Abstract

An overview of polyamine alkaloids from natural sources covering the period of 2000 until the end of 2004 is provided. The new and revised structures of such alkaloids are shown, some of the more elaborate new total syntheses published within that period of time are presented, and some biosynthetic considerations are discussed.

Evolutionarily Distinct BAHD N-acyltransferases are Responsible for Natural Variation of Aromatic Amine Conjugates in Rice

“…Phenolamides (PAs), also referred to as hydroxycinnamic acid amides or phenylamides, are the hydroxycinnamoyl acylated products of the mono-, di-, or triphenolic acid (coumaric, caffeic, or ferulic acid) substitutions of polyamines (putrescine, spermidine, agmatine, tryptamine, and serotonin) or arylmonoamines such as tyramine, octopamine, and anthranilate ( Figure 1; Bienz et al, 2005;Edreva et al, 2007;Bassard et al, 2010). PAs are a diverse group of specialized metabolites found in many plants, including wheat (Triticum aestivum), barley (Hordeum vulgare), rice (Oryza sativa), and maize (Zea mays) (Martin-Tanguy et al, 1978;Martin et al, 1985;Facchini et al, 2002;Edreva et al, 2007;Bassard et al, 2010).…”

Polyamines of Plant Origin - An Important Dietary Consideration for Human Health

“…The most common hydroxycinnamoyl substituants of spermidine include the coumaroyl, caffeoyl, feruloyl, hydroxyferuloyl, and sinapoyl acyl groups (Bienz et al, 2005). Mono-, di-, and trisubstituted hydroxycinnamoyl spermidine conjugates have also been reported (Bienz et al, 2005). Other HCAAs found in crop plants include diferuloylputrescine, diferuloylspermidine, and feruloyltyramine in Oryza sativa (rice) (Bonneau et al, 1994), hydroxycinnamoyl agmatine in Hordeum vulgare (barley) (Smith & Best, 1978), and 4-coumaroyltryptamine and feruloyltryptamine in Zea mays (maize) (Collins, 1989).…”

“…HCAAs are found in many families of higher plants (Martin-Tanguy, 1985). The most common hydroxycinnamoyl substituants of spermidine include the coumaroyl, caffeoyl, feruloyl, hydroxyferuloyl, and sinapoyl acyl groups (Bienz et al, 2005). Mono-, di-, and trisubstituted hydroxycinnamoyl spermidine conjugates have also been reported (Bienz et al, 2005).…”

Practical Synthesis of Spermine, Thermospermine and Norspermine

“…1. Structures of Spermine (1), Thermospermine (2) and Norspermine (3) pane 18b in the presence of Cs 2 CO 3 and a catalytic amount of n-tetrabutylammonium iodide, the desired double alkylation reaction proceeded readily to provide 19a and b, respectively. This one-step construction is superior to the stepwise-elongation of protected spermine and norspermine from diaminopropane.…”

“…[1][2][3][4] They interact with nucleic acids and modulate DNA synthesis and cell proliferation. [5][6][7] Due to their biological significance, practical and versatile synthetic methods are needed, but the lability of these compounds to oxidation, as well as their highly polar nature, makes handling difficult.…”