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Thermophilic Eubacteria Thermoleophilum, Bacillus Biochem. J. (1992) 284, 741-747 (Printed in Great Britain) 741 Novel linear and branched polyamines in the extremely thermophilic eubacteria Thermoleophilum, Bacillus and Hydrogenobacter Koei HAMANA,*t Masaru NIITSU,tI Shigeru MATSUZAKI,§ Keijiro SAMEJIMA,4 Yasuo IGARASHI 11 and Tohru KODAMAII *College of Medical Care and Technology, Gunma University, Maebashi, Gunma 371, Japan, tDepartment of Analytical Chemistry, Faculty of Pharmaceutical Sciences, Josai University, Sakado, Saitama 350-02, Japan, §Department of Physiology, Institute of Endocrinology, Gunma University, Maebashi 371, Japan, and (lDepartment of Agricultural Chemistry, The University of Tokyo, Tokyo 113, Japan Novel tertiary branched tetra-amines, quaternary branched penta-amines, linear penta-amines and linear hexa-amines were distributed as the major polyamines in six obligately extremely thermophilic eubacteria belonging to Thermoleo- philum, Bacillus or Hydrogenobacter. The major polyamine of Thermoleophilum album and Thermoleophilum minutum was identified as a quaternary branched penta-amine, 4,4-bis(3-aminopropyl)- 1,8-diamino-4-azaoctane {NH2[CH2]3N+([CH2]3NH2)2[CH2]4NH2} by h.p.l.c., t.l.c. and g.c.-m.s. Hydrogenobacter thermophilus and Hydrogeno- bacter halophilus contained another quaternary branched penta-amine, 4,4-bis(3-aminopropyl)- 1 ,7-diamino-4- azaheptane {NH2[CH2]3N+([CH2]3NH2)2[CH2]3NH2} as the major polyamine, and tertiary branched tetra-amines (4-(3- aminopropyl)- 1 ,7-diamino-4-azaheptane {NH2[CH2]3N([CH2]3NH2)[CH2]3NH2}, 4-(3-aminopropyl)- 1,8-diamino-4-aza- octane {NH2[CH2]3N([CH2]3NH2)[CH2]4NH2}) and 4,4-bis(3-aminopropyl)-1,8-diamino-4-azaoctane were confirmed as minor components. Bacillus schlegelii contained a branched tetra-amine, 4-(3-aminopropyl)-1,8-diamino-4-azaoctane, a branched penta-amine, 4,4-bis(3-aminopropyl)-1,8-diamino-4-azaoctane, a linear penta-amine, 1,16-diamino-4,8,13- triazahexadecane (NH2[CH2]3NH[CH2]3NH[CH2]4NH[CH2]3NH2) and linear hexa-amine(s), 1 ,20-diamino-4,8,12,17- tetra-azaeicosane (NH2[CH2]3NH[CH2]3NH[CH2]3NH[CH2]4NH[CH2]3NH2) and/or 1 ,20-diamino-4,8, 13,17-tetra- azaeicosane (NH2[CH2]3NH[CH2]3NH[CH2]4NH[CH2]3NH[CH2]3NH2). INTRODUCTION isolated extremely thermophilic aerobic Gram-negative non- sporulating hydrogen-oxidizing eubacteria, Hydrogenobacter Linear penta-amines and hexa-amines were found in extremely thermophilus (Kawasumi et al., 1984) and Hydrogenobacter thermophilic aerobic Gram-negative non-sporulating eubacteria, halophilus (Nishihara et al., 1990), growing at 70-75 'C. It various species of Thermus (Oshima, 1982; Oshima & Kawahata, seemed to us of interest to investigate the possible relationship 1983; Oshima et al., 1987; Hamana et al., 1990b, 1991) and between their thermophily and polyamine-distribution patterns. Thermomicrobium roseum (Hamana et al., 1990c), growing at A list of all polyamines described in this report is shown in 70-80 'C. Thermus thermophilus also contains a tertiary branched Table 1. tetra-amine, XXI, and a quaternary branched penta-amine, XXIV, as minor polyamines (Oshima et al., 1987; Humana et al., 1991). We have previously reported the occurrence oftwo tertiary MATERIALS AND METHODS branched tetra-amines, XXI and XXII, in extremely thermophilic Gram-negative eubacteria, Thermoleophilum album and Thermo- Culture leophilum minutum (Hamana et al., 1990a). We re-analysed Culture of Thermoleophilum album YS-3 (A.T.C.C. 35264) and polyamines of Thermoleophilum to detect quaternary branched Thermoleophilum minutum PTA-1 (A.T.C.C. 35268) was carried penta-amines. Some thermophiles have been isolated in Gram- out as described previously (Hamana et al., 1990a). positive aerobic sporulating rods belonging to Bacillus (Claus & B. schlegelii MA-48 (A.T.C.C. 43741 = DSM 2000), an Berkely, 1986). The occurrence of polyamine IX is limited to the obligately thermophilic facultatively chemolithoautotrophic moderate thermophiles such as Bacillus stearothermophilus, bacterium which oxidizes molecular hydrogen, was grown Bacillus thermodenitrificans and Bacillus acidocaldarius (Stevens heterotrophically in the polyamine-free basal mineral medium & Morrison, 1968; Hamana et al., 1989) and is associated with containing NH4+/pyruvate medium, pH 7.0 at 60 or 75 'C their moderate thermophily. The moderately thermophilic bacilli (Schenk & Aragno, 1979). For autotrophic growth, NaHCO3 growing at 50-65 'C lack long and branched polyamines. Since was added to the basal mineral medium, pH 7.1, and cultures the occurrence of long linear or branched polyamines is limited were then incubated under 02/CO2/H2 (HCO3-/H2 medium) at to the extremely thermophilic eubacteria and these polyamines 60 'C (Schenk & Aragno, 1979). are not found in archaebacteria including extreme thermophiles H. thermophilus strains TK-6 and TK-G were autotrophically (Kneifel et al., 1986), the presence of these polyamines is cultivated in the basal medium, pH 7.2, at 70 'C under a gas apparently associated with their extreme thermophily and rel- mixture consisting of H2, 02 and CO2 (15:3:2, by vol.) evant to chemotaxonomy within thermophilic eubacteria. (Kawasumi et al., 1984). Cultivation of a halophile, H. halophilus In order to survey the distribution of polyamines in thermo- TH-1 12, was performed autotrophically in the basal medium, philic bacilli, we analysed polyamines in an extreme thermophile, pH 7.0, containing 0.5 M-NaCl at 70 'C under the gas phase, Bacillus schlegelii (Schenk & Aragno, 1979). Previously, we H2/02/CO2 = 7:1:1, by vol. (Nishihara et al., 1990). t To whom all correspondence should be addressed. Vol. 284 742 K. 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I) 0m 324' _ = v = z = Y x = Y g *;E,-- 42 0. 6w U) C) 0~~~~~~~~~~~~~~~~~~~~~~~~~r 0~~~~~~~ 3~~~~~~~X3 10 O r: o o o Cd Cd C.'-C: W 0 . 40 '@4 C)~~d0 !0 !. -0 4 .I 0 r > 14 4 0 C)4uE0 0~~~~~~~~~~~~~~~~~0c Cl CU CUO ~~~~~~~ C"O0 U)00 40 CU 0 ~ ~ ~ ~*02~~ 04 040 040 0 0 0 . ~C 0C 0~ B WO E U0cd CU0 ZZ~ ~~~~~~Ou ZVI)-Xz~ <Ud HU-4 =O HF. 41 U)~~~~~~~~~~~~~~A( U)~~~~~~~~~~~~~~( C) C) ~ ~~~~~~~.0 0 0 C.)~~Cd0 *6 CU C) C)~~~~~~~~~4C 04.2 Ei ~~~~~C) CUC) CUC)-d~ * C 0 0 0- 0C)~ Cy 1992 Polyamines in thermophilic Thermoleophilum, Bacillus and Hydrogenobacter 743 Polyamine analysis (a) > x The organisms were harvested and homogenized in equal N volumes of cold I M-HC104. The HC104 extracts were analysed for their polyamine contents by h.p.l.c. on a column of cation- exchange resin as described previously (Matsuzaki et al., 1982). (b) > G.c. of polyamines was performed on a GC-9A gas chromato- graph (Shimadzu Co. Ltd., Tokyo, Japan) after treatment of the xX polyamine samples with heptafluorobutyrate (Matsuzaki et al., 1989). The Pyrex glass column (2.1 m, 3 mm internal diameter) was packed with 3 % SE-30 on 100-120-mesh Chromosorb WHP (Gasukuro Kogyo Inc., Tokyo, Japan). Helium was used as the carrier gas with a flow rate of40 ml/min. The column oven (c) > Ji I I temperature was raised from 120 to 280 °C (16 °C/min) or I I I 200-280 °C (8 'C/min) and the injector temperature was 300 'C. > The identity of polyamines was confirmed by g.c.-m.s. on a JMS- DX 300 (JEOL Co. Ltd., Tokyo, Japan) which was operated in (d I the electron-impact mode at an ionization energy of 70 eV. The x %", identity of major polyamines was also confirmed by t.l.c. on cellulose (Avicel SF, Funakoshi, Tokyo, Japan) using the solvent (d) 5; system propan-2-ol/ammonia (7:3, v/v) (Hamana & Matsuzaki, 1984). Various linear tetra-amines, penta-amines and hexa- amines, and tertiary branched tetra-amines (XXI, XXII and C.) XXIII) and quaternary branched penta-amines (XXIV, XXV C and XXVI) were synthesized according to our previous report C.)0 (Niitsu & Samejima, 1986) or Oshima et al. (1987). NN-Bis(3- 0 aminopropyl)methylamine was purchased from Tokyo Kasei 0 (Tokyo, Japan). (e) a) cc RESULTS Thermoleophilum H.p.l.c. analysis of the polyamines extracted from the normal culture of the two species of Thermoleophilum showed that the major unknown peak was XXV (Fig. la and 11). Minor peaks (f) corresponding to polyamines I, II, IV, V, XXI, XXII and XXIV were also detected (Fig. If). When the polyamine fraction was analysed by g.c., two major peaks corresponding to tertiary branched tetra-amines, XXI and XXII, were found (Fig. 2a). The identity of these tetra-amines was confirmed by m.s. On the other hand, the g.c. analysis of synthesized authentic polyamine XXV I 5 also gave the two tertiary tetra-amines and two peaks corre- sponding to the degradation products (NH2CH2CH CH2 and X NH2CH2CH2CH-CH2), as shown in Fig. 3. The products were *1 also detected during g.c.
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