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Putrescine and Cadaverine in Thehuman Gut 1993; 34:489-493 489 Presence ofN-acyl and acetoxy derivatives of putrescine and cadaverine in the human gut Gut: first published as 10.1136/gut.34.4.489 on 1 April 1993. Downloaded from K E Murray, K J Shaw, R F Adams, P L Conway Abstract from isolates of gut micro-organisms. Identifica- N-acyl and acetoxy derivatives of putrescine tion of the compounds was obtained in 1-10 .tg and cadaverine have been found in the faeces samples by thin layer chromatography (TLC), of children and in cultures of isolates of gut FDMS, and accurate mass measurement of the bacteria. The evidence was accumulated from molecular ions of the 1-dimethylaminonaphtha- two dimensional, thin layer chromatography, lene-5-sulphonyl- (DANS) derivatives of the field desorption mass spectrometry, and amines concerned. accurate mass measurement of the DANS derivatives of the amines. The acetoxy com- pounds of putrescine and cadaverine have not Methods previously been reported (Gut 1993; 34: 489-493) SUBJECTS AND SOURCES OF SPECIMENS An initial source of faecal specimens was a group of five infants admitted to hospital with salmon- Monoacetylcadaverine (N-acetyl-1,5-diamino- ellosis (Table I). The specimens were taken pentane) and monopropionylcadaverine (N- before antibiotic treatment was begun. A group propionyl-1,5-diaminopentane) have been of 13 children (reported previously6) provided shown to occur frequently in the urine of a second source of faecal specimens. These schizophrenic patients, of psychotic or mentally children had been admitted to hospital for defective patients, and of mentally normal reasons unrelated to gastric problems and were patients in hospital.' These same compounds not receiving any drug treatment. Spent culture have since been reported in human blood, where fluids of faecal smears, single cell isolates from their levels were found to be significantly higher duodenal biopsy specimens, and a specimen of in schizophrenic patients than in normal sub- caecal fluid obtained at necropsy from a child http://gut.bmj.com/ jects.2 3 Acetylputrescine (N-acetyl-l ,4-diamino- with suspected infant botulism were the non- butane), and to a lesser degree acetylcadaverine, faecal samples used. The cultures were incu- along with other acetyl polyamines, occur in bated anaerobically for four days at 37°C in increased amounts in the urine of cancer patients prereduced supplemented brain-heart infusion compared with normal subjects.4 broth.7 Many methods have been developed for analysing these compounds as biochemical on September 30, 2021 by guest. Protected copyright. markers to aid diagnosis and to monitor the MICROBIOLOGY regression of cancerous tumours after chemo- When faecal samples were inadequate for pro- Division of Food therapy.5 In a recent study in this laboratory, cessing directly to determine the concentration Processing, CSIRO, PO tentative identifications were made of mono-N- of amines, faecal smears were taken with sterile Box 52, North Ryde, New acyl-diamines in the faeces of 35 of 44 infants swabs. The tips of the swabs were transferred to South Wales, Australia K E Murray, with gastroenteritis, by field desorption mass 5 ml aliquots of Stuart's transport medium and K J Shaw, spectrometry (FDMS) of the fluorescamine individual smears and medium were used to R F Adams, derivatives.6 We present here evidence for the inoculate 100 ml prereduced supplemented P L Conway presence of N-acyl- and acetoxy-putrescines and brain-heart infusion broth (SBHI) containing Correspondence to: Dr K J Shaw. cadaverines in a variety of samples associated haemin (5 .g/ml), vitamin K (10 [ig/ml), and Accepted for publication with the human gut, namely: faeces from yeast extract (0 5%). The SBHI was prereduced 1 September 1992 children, caecal fluid, and spent culture fluid with resazurin and cysteine.7 The inoculated medium was incubated anaerobically in 5% hydrogen and 95% nitrogen for four days at TABLE I Thepresence ofdansyl-diamine and related molecular ions in material recoveredfrom 37°C. After incubation, the bacterial cells were thin layer chromatography separationsfollowed byfield desorption mass spectrometry separated by centrifugation at 10000 g and the Acyldiamines Diamines Acetoxydiamines spent medium was processed to concentrate any (m/z) (m/z) (m/z) diamines as described below. Duodenal biopsy and aspirate samples were Source 363 377 391 540 554 568 612 626 collected by endoscopy, placed immediately in At Faeces ++* ++ + +++ ++ Stuart's and inserted in an B Faeces + + + + +++ + + transport medium, C Faeces + + + + +++ + anaerobic atmosphere inside a Biobag (Marion D Faeces +++ ++± +++ +++ Scientific Industries, USA). Microbiological Et Faeces + + +++ F§ Caecal fluid + + + + +++ culturing was carried out within four hours of sampling. Necropsy samples from the ascending * Semiquantitative assessment of the relative amounts was made from the intensity of the spots where of one of from possible and from the ion intensity in the FD spectra. colon subject suspected suffering Relative abundance of ion: + + + + very large, + + + large, + + medium, + small. infant botulism were transferred immediately t Subjects A-D were infants aged 6-12 months, admitted to hospital with salmonellosis. after collection to an anaerobic atmosphere t Subject E was a hyperactive child, aged 6 years. § Subject F was a child aged 3 years with suspected infant botulism. inside a Biobag and stored overnight at 40C. All 490 Murray, Shaw, Adams, Conway TABLE II Presence ofdiamtine-dansvl and related molecular ions infield desorption spectra ofDANS amines in faeces and microbial cultures Acyldiamines Diamines Acetoxdia5ines (m/z) (mn/z) Gut: first published as 10.1136/gut.34.4.489 on 1 April 1993. Downloaded from 363 377 39! 405 540 554 568 584 598 612 626 640 SubjecLtsource: Faeces - infants* A F 4 Hospital ++t ++ + ++ ++ B M 7 Hospital + ++++ +++ T ± ++++ C M 4 Hospital ± ++ D F 12 Hospital + ++ + + E M 10 Hospital + + T + +++± F M 12 Home + + ± + ±±±+ + +++ ++ ++ G F 9 Home +++ + T ±++ + +++ ++ H F 8 Home + + + +++ +± ± I F 6 Home + + + ±++ +± +++ J M 12 Home ++ ++ K F 4 Home + ++ ++ ++ + ++ L F 4 Home + + ±++ + + +++ ++± M F 11 Home ± + T ++ ++ Culturest 1 Faecal smear ++ + 2 Faecal smear + ++ + +±+ 3 Faecal smear + ++++ 4 Isolate from gut + ± 5 Isolate from gut +± +±+++ 6 Isolate from gut T + ± ± 7 Isolate from gut + 8 Isolate from gut ++ +++ + * Subjects listed with sex and age in months. All subjects were healthy and were studied previously (reference 6). t Faecal smears were from hyperactive children (1, 2) and a child with suspected infant botulism (3). Isolates of single microbial strains were from gut biopsy tissue of two children (4, 5, 6 and 7, 8). i Assessment of relative abundance of ions was as described in Table I. T= trace. samples were serially diluted in 10 fold steps in were steamed, equilibrated to 50°C in a water prereduced phosphate buffered saline (0 01 M, bath, and then spun to distribute the culture pH 7-2). Aliquots (100 1.) of the dilutions were medium uniformly on their walls before they inoculated into prereduced SBHI containing 2% were inoculated. After incubation at 37°C for five agar. Tubes containing 10 ml sterile SBHI agar days, dominant colonies were subcultured and purified by spirally inoculating prespun tubes of http://gut.bmj.com/ prereduced SBHI agar. The spiral tubes were further incubated for five days at 37°C. All manipulations of dilutions and SBHI agar tubes 320 *-278 were performed under a stream of carbon ,_334 dioxide gas. Purified cultures were finally grown 306-. in prereduced SBHI broth with 20% glycerol and stored at -20°C in the culture medium. Before on September 30, 2021 by guest. Protected copyright. 354- the cultures were frozen, spent culture fluid was prepared by inoculation of 0-1% in SBHI broth with 1% glucose. After three days' incubation at 278 *-'603(589) 37°C, the cultures were centrifuged at 10 000 g to *-264 remove the bacterial cells. RECOVERY AND DERIVATISATION OF AMINES The recovery of amines from samples by ion 568 _..250 exchange chromatography and their derivatisa- tion was as previously described.' The FDMS 540 -640 method had a limit of detection of about 100 nmol/g faeces, based on a sample size of 1 g, one 393a /-6626 294 412 tenth of the sample applied to the FD emitter and an MS sensitivity of about 10 nmol in the ion 391 source. The limit of detection of the TLC b54 ' methodology was previously estimated to be 377 2. 363'e 0-2 nmol." Figure 1: Composite molecular ion-thin layer chromatography (TLC) map ofj 1-dimethylaminonaphthalene-5-sulphonyl (DANS)-amines (free) recovered by ion exchange TLC from thefaeces ofchildren. Identity ofmolecular ions (m/z), upper left to origin. Centre ofspots Two dimensional TLC (2-D TLC) was shown. 318 - piperidine, 278 - dimethylamine (from reagent in reaction), 334 - based on 5-aminopentanal (from cadaverine), 320 - isopentylamine (mixed 2- and 3-methvlbutvlamines the methodology of Seiler and Weichmann.' The (from isoleucine and leucine respectively), 306 - isobutylamine (from valine), 354 - solvents of choice were: first direction, ethyl 2-phenylethylamine, 278 - ethvlamine, 603 - p-tyramine, 589 - p-hydroxvbenzylamine likelv acetate:cyclohexane (3:2 v/v); and second (present onlv when p-tyramine is large) 264 - methylamine, 250 - ammonia, 568 - cadaverine, 540 - 1,3-diaminopropane, 393 - tryptamine, 554 - putrescine, 612 - 2-acetoxyputrescine, 626 direction, benzene:triethylamine (5: 1). A second - 2-(or 3)-acetoxvcadaverine, 640 - 2-(or 3)-propionvloxycadaverine, 294 - ethanolamine, solvent combination found to separate diamines 412 - acetyltyramine (present when tyramine is large), 391 - mono-N-propionvlcadaverine, and acetoxydiamines was: first direction, as 377 - mono-N-acetylcadaverine, 363 - mono-N-acetylputrescine. Experimental conditions: 2-D TLC solvent combination ofSeiler and Weichmann. s above; second direction, chloroform: isopropanol Presence ofN-acyl and acetoxy derivatives ofputrescine and cadaverine in the human gut 491 100 - to establish the identities of the DANS-amine d CAD derivatives separated by 2-D TLC, after solvent 80 recovery from the fluorescent spots.
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