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J. Gen. Appl. Microbiol., 62(6): 334–339 (2016)

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J. Gen. Appl. Microbiol., 62(6): 334–339 (2016) J. Gen. Appl. Microbiol., 62, 334–339 (2016) doi 10.2323/jgam.2016.05.007 „2016 Applied Microbiology, Molecular and Cellular Biosciences Research Foundation Short Communication Occurrence of two novel linear penta-amines, pyropentamine and homopyropentamine, in extremely thermophilic Thermus composti (Received May 7, 2016; Accepted May 26, 2016; J-STAGE Advance publication date: November 22, 2016) Koei Hamana,1,* Takemitsu Furuchi,2 Hidenori Hayashi,1 Takashi Itoh,3 Moriya Ohkuma,3 and Masaru Niitsu2 1 Faculty of Engineering, Maebashi Institute of Technology, Maebashi, Gunma 371-0816, Japan 2 Faculty of Pharmaceutical Sciences, Josai University, Sakado, Saitama 350-0295, Japan 3 Japan Collection of Microorganisms (JCM), RIKEN BioResource Center, Tsukuba, Ibaraki 305-0074, Japan Key Words: homopyropentamine; penta-amine; polyamine; pyropentamine; thermophilic bacteria; Thermus Cellular polyamine distribution profiles in extremophilic N4-aminopropyl-N8-aminobutylspermidine, Furuchi et al., bacteria and archaea are related to their optimum growth 2015b) (3344) and homopyropentamine (formerly temperature, pH, and salt concentrations, as well as their bis(aminopropyl)homospermidine, Furuchi et al., 2015b) phylogenetically classified locations (Hamana, 2002a; (3443) were found in an acid-extract from Thermus Hamana and Hosoya, 2006; Hamana and Matsuzaki, 1992). composti grown at 75∞C. The distribution of linear penta-amines, linear hexa- T. composti JCM 19902T, T. islandicus JCM 19901T, T. amines, and branched penta-amines, have been reported antranikianii JCM 19900T, and T. igniterrae JCM 19899T in extensive bacterial and archaeal hyper-/extreme were provided by JCM (Japan Collection of Microorgan- thermophiles (Hamana et al., 1990, 1991b, 1992a, 1996, isms, RIKEN BioResource Center (BRC), Tsukuba, 1998, 1999, 2008, 2009, 2014; Hosoya et al., 2004). These Ibaraki, Japan) through the National Bio-Resource Project highly basic long polyamines are possibly associated with of MEXT and cultivated aerobically at 60–75∞C in the their thermophily to stabilize cellular nucleic acids and organic liquid media R2A (pH 7.2) or 162 (pH 7.2) (JCM other acidic components under high thermal growth envi- Catalogue of Strains, 2016). Organisms harvested at the ronments (Oshima et al., 2011; Terui et al., 2005). early stationary phase were homogenized in 5% perchrolic Where each linear penta-amine is abbreviated as the acid (PCA). The PCA extract was subjected to a column number of methylene (CH2) groups between amino or of cation-exchange resin, Dowex 50WX8 (1 cm I.D. ¥ 3 imino (NH2 or NH) groups, four structural isomers of cm), and eluted with 6M HCl to concentrate the aliphatic linear penta-amines consisting of two polyamines. The concentrated polyamines were analyzed aminopropyl and two aminobutyl moieties, by high-performance (high speed) liquid chromatography 3434 [NH2(CH2)3NH(CH2)4NH(CH2)3NH(CH2)4NH2], (HPLC) on a Hitachi L6000 equipped with a column of 3344 [NH2(CH2)3NH(CH2)3NH(CH2)4NH(CH2)4NH2], cation-exchange resin, Hitachi 2619F (4 mm I.D. ¥ 50 mm) 3443 [NH2(CH2)3NH(CH2)4NH(CH2)4NH(CH2)3NH2], kept at 70∞C. Polyamines were eluted by a linear gradient and 4334 [NH2(CH2)4NH(CH2)3NH(CH2)3NH(CH2)4NH2] of NaCl in citrate buffers (0.045 M sodium citrate-0.061 can exist and be chemically synthesized (Furuchi et al., M citric acid-0.063 M NaCl, pH 3.9 and 0.20 M sodium 2015b). Although the isomer aminopropylcanavalmine citrate-2.0 M NaCl, pH 7.6) and detected by post-labeled (3434) has been found in the leguminous seeds of fluorometry using a Hitachi F1050 fluorescence Canavania gladiate (Matsuzaki et al., 1990) and Pisum spectrometer after heating with o-phthalaldehyde reagent sativum (Hamana et al., 1992b), and the flesh of a sea cu- at 70∞C (Hamana, 2002b). Minor polyamines were non- cumber (Hamana et al., 1991a), the other three isomers, detectable in the HPLC. After heptafluorobutyrization 3344, 3443 and 4334, have not been detected in natural (HFB) of the concentrated polyamines, high-performance sources, including bacterial and archaeal thermophiles. gas chromatography (HPGC) on a SHIMADZU GC-17A In the present study, through the polyamine analyses of and HPGC-mass spectrometry (HPGC-MS) on a JEOL four additional extremely thermophilic Thermus species, JMS-700, equipped with a long capillary column of Inert two novel linear penta-amines, pyropentamine (formerly Cap 1MS (0.32 mm I.D. ¥ 30 m) (GL Sciences), instead *Corresponding author: Koei Hamana, Faculty of Engineering, Maebashi Institute of Technology, Maebashi, Gunma 371-0816, Japan. Tel: +81-27-234-4611 Fax: +81-27-234-4611 E-mail: [email protected] None of the authors of this manuscript has any financial or personal relationship with other people or organizations that could inappropriately influence their work. Penta-amines in Thermus 335 Table 1. Cellular concentrations of polyamines of Thermus, Marinithermus and Vulcanithermus belonging to the bacterial order Thermales. Ref. ∞CpH Polyamines (mmol/g wet wt. cell): 34333444 333 3(3)3 3(3)4 343 334 344 T Thermus composti K-39 R2A Med. JCM 19902 70 7.2 æ 0.03 0.02 0.30 1.05 0.30 * * 0.20 1.20 1.05 R2A Med. 75 7.2 æ 0.04 0.14 0.35 1.00 0.05 * * 0.30 1.20 0.92 162 Med. 60 7.2 0.05 0.03 0.10 0.57 1,10 0.45 0.02 æ 0.36 1,40 0.08 162 Med. 70 7.2 æ 0.20 0.20 0.61 0.72 0.10 * * 0.15 1.20 0.25 162 Med. 75 7.2 0.01 0.17 0.05 0.37 0.81 0.15 * * 0.15 1.22 1.00 T Thermus islandicus PRI 3838 R2A Med. JCM 19901 70 7.2 0.03 0.10 0.32 0.50 0.73 0.67 ææ0.30 1.20 0.02 T Thermus aquaticus YT-1 ATCC 25104 2004 70 7.6 æ 0.26 0.14 0.68 1.38 1.06 ææ0.21 0.80 0.05 T JCM 10724 2014 75 7.6 æ 0.10 0.10 0.33 0.75 1.50 ææ0.12 1.24 æ T Thermus antranikianii HN3-7 ATCC 700961 2004 70 7.6 æ 0.10 0.01 0.25 1.00 0.32 ææ0.10 0.30 0.05 T R2A Med. JCM 19900 70 7.2 0.01 0.15 0.17 0.37 1.20 0.70 ææ0.20 0.90 0.05 Thermus antranikianii AZM44c05 NBRC 106113 2014 70 7.2 0.04 0.16 0.11 0.35 0.51 0.16 ææ0.11 0.45 æ T Thermus arciformis HT91 JCM 15153 2014 70 8.2 æ 0.05 0.08 0.37 1.35 1.00 ææ0.30 0.95 0.12 2014 75 8.2 æ 0.02 0.03 0.52 0.80 0.77 ææ0.02 1.35 0.19 T Thermus brockianus YS38 NCIMB 12676 2004 70 7.6 æ 0.10 0.10 0.75 1.30 0.80 ææ0.20 2.50 0.20 Thermus brockianus AZM44c06 NBRC 106112 2014 70 7.2 æ 0.10 0.26 0.87 0.49 0.55 ææ0.65 1.20 0.01 T Thermus filiformis Wai33 A1 JCM 11600 2014 65 8.2 æ 0.10 æ 0.80 0.15 0.03 ææ0.40 0.05 0.02 T ATCC 43280 1998 70 7.6 0.04 0.20 0.09 0.88 1.04 0.16 0.02 æ 0.10 0.41 0.09 Thermus filiformis T351 ATCC 31674 1998 70 7.2 æ 0.25 0.05 0.22 0.11 0.26 ææ0.20 0.82 0.02 T Thermus igniterrae RF-4 ATCC 700962 2004 70 7.6 æ 0.15 0.01 0.10 1.00 0.38 ææ0.05 0.10 0.05 T R2A Med. JCM 19899 70 7.2 0.02 0.10 0.10 0.60 0.80 1.06 ææ0.50 1.00 0.05 T Thermus kawarayensis JCM 12314 2008 70 7.2 0.04 0.04 0.40 0.25 0.75 0.98 ææ0.10 0.48 0.20 Thermus kawarayensis 273 Med. NBRC 106110 2014 70 7.2 0.10 0.10 0.22 1.20 0.60 0.91 ææ0.92 0.48 0.05 1121 Med. 2014 70 7.5 0.05 0.16 0.10 1.19 0.67 0.38 ææ1.02 0.39 æ Thermus kawarayensis 273 Med. NBRC 106111 2014 70 7.2 0.07 0.17 0.12 1.05 1.00 0.38 ææ0.96 1.07 0.06 1121 Med. 2014 70 7.5 0.05 0.20 0.25 0.67 0.91 0.26 ææ0.28 1.19 0.07 T Thermus oshimai SPS17 JCM 11603 2014 65 8.2 æ 0.20 0.10 0.45 1.60 0.10 ææ0.20 0.45 0.10 T NCIMB 13400 1996b 70 8.2 0.01 0.02 0.05 0.18 0.42 0.60 ææ0.20 1.40 0.06 T Thermus scotoductus SE-1 JCM 11601 2014 65 8.2 æ 0.10 0.03 0.30 1.17 0.05 ææ0.20 0.78 0.10 T ATCC 51532 1998 65 7.2 æ 0.15 æ 0.24 1.70 0.30 ææ0.22 1.50 0.45 Thermus scotoductus NH NCIMB 11245 1999 60 8.2 ææ0.08 1.05 2.50 0.39 ææ0.08 0.12 0.28 Thermus scotoductus DI NCIMB 11246 1999 65 8.2 ææ0.04 0.30 1.90 1.40 ææ0.10 0.15 0.12 Thermus scotoductus X-1 ATCC 27978 1998 70 7.2 æ 0.30 0.02 0.06 0.30 0.21 ææ0.10 0.41 0.05 Thermus sp.
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