sym-Homospermidine, a naturally occurring polyamine

Kuttan, Ramadasan; Radhakrishnan, A. N.; Spande, Thomas F.; Witkop, Bernhard

doi:10.1021/bi00779a001

Cited by 52 publications

(12 citation statements)

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“…This was the first record of Homospd in bacteria. Homospd had previously been found in the leaves of the sandal wood tree (Santalum album L.) (81,82). The * Spermidine sporadically occurs in cultured rhizobia, but possibly due to uptake or contamination from growth media (33).…”

Section: Polyamines In Plant-associated Bacteriamentioning

confidence: 99%

Biogenic Amines in Rhizobia and Legume Root Nodules

Fujihara

2009

Microb. Environ.

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Root-nodule bacteria (rhizobia) are of great importance for nitrogen acquisition through symbiotic nitrogen fixation in a wide variety of leguminous plants. These bacteria differ from most other soil microorganisms by taking dual forms, i.e. a free-living form in soils and a symbiotic form inside of host legumes. Therefore, they should have a versatile strategy for survival, whether inhabiting soils or root nodules formed through rhizobia-legume interactions. Rhizobia generally contain large amounts of the biogenic amine homospermidine, an analog of spermidine which is an essential cellular component in most living systems. The external pH, salinity and a rapid change in osmolarity are thought to be significant environmental factors affecting the persistence of rhizobia. The present review describes the regulation of homospermidine biosynthesis in response to environmental stress and its possible functional role in rhizobia. Legume root nodules, an alternative habitat of rhizobia, usually contain a variety of biogenic amines besides homospermidine and the occurrence of some of these amines is closely associated with rhizobial infections. In the second half of this review, novel biogenic amines found in certain legume root nodules and the mechanism of their synthesis involving cooperation between the rhizobia and host legume cells are also described.

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Section: Polyamines In Plant-associated Bacteriamentioning

confidence: 99%

Biogenic Amines in Rhizobia and Legume Root Nodules

Fujihara

2009

Microb. Environ.

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“…Second, we used homospermidine, also a naturally occurring polyamine (16), as an alternative tool to study the site of metabolism by BPAO, since extension of one methylene group would abrogate the acrolein elimination side reaction that results in the above-described mechanistic conundrum. Our results reaffirm the initial conclusions of the Tabors and Bachrach that PAO metabolism of polyamines occurs strictly at the primary amino termini.…”

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Reaffirmation That Metabolism of Polyamines by Bovine Plasma Amine Oxidase Occurs Strictly at the Primary Amino Termini

Lee

Sayre

1998

Journal of Biological Chemistry

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Oxidation of the biologically important polyamines spermine and spermidine by plasma amine oxidase (PAO) was specified many years ago to occur at the terminal primary rather than internal secondary amine positions. However, the finding of sequential enzymatic conversion of spermine to spermidine and then to putrescine (1,4-butanediamine) is superficially suggestive of metabolism at the secondary amine positions, and a recent publication (Houen, G., Bock, K., and Jensen, A. L. (1994) Acta Chem. Scand. 48, 52-60) claimed that the original interpretation of preferential "terminal" deamination does not stand up to scrutiny with modern methods of analysis. We herein demonstrate that the findings cited in support of secondary amine deamination can arise artifactually from spontaneous elimination/addition reactions following initial metabolism at the terminal positions of 3-(aminopropyl)amines. We further find no evidence for the ability of PAO to metabolize the secondary amine position in homospermidine, which is devoid of such complicating side reactions. Our results support the original claimed specificity of PAO for the primary amino termini of polyamines, all of which are consistent with the general finding that the quinone-dependent copper amine oxidases specifically metabolize primary amines.In the early days of clarification of the substrate specificity of the soluble amine oxidase present in mammalian plasma (PAO), 1 the Tabor group (1) demonstrated that the naturally occurring polyamines spermine and spermidine are metabolized at the primary amino termini, in contrast to several bacterial amine oxidases that metabolize polyamines at the secondary nitrogen atoms (2, 3). The soluble plasma enzyme (EC 1.4.3.6), now known as one class of a family of coppercontaining amine enzymes, is thereby distinguished from the flavin-dependent amine oxidases present in mammalian mitochondria, which although primarily involved in metabolism of primary amines, can also dehydrogenate certain secondary and tertiary amines (4). With the recognition that the copper-containing amine oxidases metabolize amines through a transamination process mediated by an active site 2,4,5-trihydroxyphenylalanine quinone cofactor derived post-translationally from a conserved tyrosine (5), the restriction to primary amine substrates might be viewed as a simple consequence of the need to form a neutral Schiff base with the quinone cofactor in the first step of the enzymatic mechanism. However, secondary amines could theoretically also fulfill a transamination mechanism via initial formation of an iminium quinone-derived intermediate. In fact, there have been isolated claims of the ability of certain secondary amines to be processed by the copper-containing plasma amine oxidases (6, 7). Nonetheless, in these cases (Nmethyl-␤-aminopropionitrile and ␤,␤'-iminodipropionitrile), we suspected that the commercial materials contained traces of the corresponding primary amine ␤-aminopropionitrile, a known substrate/inactivator of PAO (8) and inactivator of ly...

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“…Assuming that this is true, the enzyme systems which transfer the aminobutyl moiety to PUT or to SPD must be present in sword bean seed. The pathway of homoSPD synthesis from two molecules of PUT via Shifts base formation has been proposed by several workers (15,25,26). However, a selective aminobutyl transfer reaction to the aminopropyl group of SPD has not been hitherto recognized.…”

Section: Discussionmentioning

confidence: 99%

“…Recently, we found two unusual polyamines, homoSPD and CAN, in the seed of sword bean Canavalia gladiata (5). HomoSPD, NH2(CH2)4NH(CH2)4NH2, has been found in a wide variety of organisms such as bacteria (11,18,22,26), algae (10, 20), lower and higher plants (15,28,29), and certain vertebrates (14,17 (7,8). The mechanism of biosynthesis and the potential role of these rare polyamines in plants, however, remain to be worked out.…”

mentioning

confidence: 99%

“…Recently, we found two unusual polyamines, homoSPD and CAN, in the seed of sword bean Canavalia gladiata (5). HomoSPD, NH2(CH2)4NH(CH2)4NH2, has been found in a wide variety of organisms such as bacteria (11,18,22,26), algae (10,20), lower and higher plants (15,28,29), and certain vertebrates (14,17). On the other hand, CAN, NH2(CH2)4NH(CH2)3NH(CH2)4NH2, appears to be a unique tetraamine, since, to our knowledge, the occurrence of CAN in nature has not been demonstrated.…”

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confidence: 99%

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Distribution and Metabolism of sym-Homospermidine and Canavalmine in the Sword Bean Canavalia gladiata cv Shironata

Fujihara

Nakashima²,

Kurogochi³

et al. 1986

Plant Physiol.

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The unusual polyamines, sym-homospermidine (homoSPD) and canavalmine (CAN), were found in the seed of Canavalia species such as C. gladiata, C. ensiformis, and C. brasilensis, but not in those of other leguminous crops. To examine the distribution and metabolism of homoSPD and CAN in sword bean, C. gladiata cv Shironata, polyamine analysis was carried out throughout the life cycle of this plant. During seed germination, putrescine (PUT), spermidine (SPD), and spermine (SPM) were accumulated in the radicle and hypocotyl. HomoSPD and CAN were, however, maintained at very low levels over a 6-day period of germination. In nodulated sword bean plants, a large quantity of homoSPD was found in the root nodule. CAN was detected exclusively in the senescent nodule at very low concentrations. These polyamines were not detected in any other organs including root, stem, leaf, vine, flower, and pod, while PUT, SPD, and SPM were always found in those organs. As plants reached the reproductive stage, homoSPD and CAN appeared in the immature seed and their concentrations increased as seed formation progressed. By contrast, the level of SPM continuously decreased during seed development. In developing seeds, considerable accumulation of canavanine, an analog of arginine, which is a precursor in polyamine biosynthesis, was also observed.The aliphatic polyamines, PUT,' SPD, and SPM, occur ubiquitously in living organisms. These organic polycations are known to be involved in various cellular metabolic processes including synthesis of proteins and nucleic acids (1). The physiological and biochemical significance of polyamines in plant growth and development has recently been reviewed (21,24). In addition to the widespread usual polyamines, structural analogs, in which the length of methylene chain or the arrangement of aliphatic groups in the amines differs from the usual polyamines, have been found in certain organisms (19). Hamana and Matsuzaki (10) proposed that these unusual polyamines could serve as chemical phylogenic and taxonomic markers. Recently, we found two unusual polyamines, homoSPD and CAN, in the seed of sword bean Canavalia gladiata (5). HomoSPD, NH2(CH2)4NH(CH2)4NH2, has been found in a wide variety of organisms such as bacteria (11,18,22,26), algae (10, 20), lower and higher plants (15,28,29), and certain vertebrates (14,17 (7,8). The mechanism of biosynthesis and the potential role of these rare polyamines in plants, however, remain to be worked out. The present paper describes the distribution and metabolism ofhomoSPD and CAN throughout the growth period of sword bean plants (C. gladiata cv Shironata). The occurrence of polyamines in various leguminous seeds, including other species of Canavalia, has also been demonstrated. MATERIALS AND METHODS Plant Materials. A variety of leguminous seeds includingGlycine max, Phaseolus angularis, P. mungo, P. vulgaris, P. lunatus, Pisum sativum, Vicia faba, Vigna sinensis, Arachis hypogaea, Dolicos lablab, and Canavalia gladiata were supplied by the Seed Storage Lab...

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sym-Homospermidine, a naturally occurring polyamine

Cited by 52 publications

References 28 publications

Biogenic Amines in Rhizobia and Legume Root Nodules

Biogenic Amines in Rhizobia and Legume Root Nodules

Reaffirmation That Metabolism of Polyamines by Bovine Plasma Amine Oxidase Occurs Strictly at the Primary Amino Termini

Distribution and Metabolism of sym-Homospermidine and Canavalmine in the Sword Bean Canavalia gladiata cv Shironata

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