Skip to main content
Erschienen in: Journal of Natural Medicines 1/2018

05.12.2017 | Original Paper

Dehydropropylpantothenamide isolated by a co-culture of Nocardia tenerifensis IFM 10554T in the presence of animal cells

verfasst von: Yasumasa Hara, Midori A. Arai, Kanae Sakai, Naoki Ishikawa, Tohru Gonoi, Takashi Yaguchi, Masami Ishibashi

Erschienen in: Journal of Natural Medicines | Ausgabe 1/2018

Einloggen, um Zugang zu erhalten

Abstract

A new amide, named dehydropropylpantothenamide (1), was obtained by a co-culture of Nocardia tenerifensis IFM 10554T in the presence of the mouse macrophage-like cell line J774.1 in modified Czapek-Dox (mCD) medium. Compound 1 was synthesized from d-pantothenic acid calcium salt in 6 steps. The absolute configuration of natural compound 1 was determined by comparisons of the optical rotation and CD spectra of synthetic 1. In the present study, a new method for producing secondary metabolites was demonstrated using a “co-culture” in which the genus Nocardia was cultured in the presence of an animal cell line.
Anhänge
Nur mit Berechtigung zugänglich
Literatur
2.
Zurück zum Zitat Schatz A, Bugie E, Waksman SA (1944) Streptomycin, a substance exhibiting antibiotic activity against gram-positive and gram-negative bacteria. Proc Soc Exp Biol Med 55:66–69CrossRef Schatz A, Bugie E, Waksman SA (1944) Streptomycin, a substance exhibiting antibiotic activity against gram-positive and gram-negative bacteria. Proc Soc Exp Biol Med 55:66–69CrossRef
3.
Zurück zum Zitat McGuire JM, Bunch RL, Anderson RC, Boaz HE, Flynn EH, Powell HM, Smith JW (1952) Ilotycin, a new antibiotic. Antibiot Chemother 2:281–283 McGuire JM, Bunch RL, Anderson RC, Boaz HE, Flynn EH, Powell HM, Smith JW (1952) Ilotycin, a new antibiotic. Antibiot Chemother 2:281–283
4.
Zurück zum Zitat Umezawa H, Ueda M, Maeda K, Yagishita K, Kondo S, Okami Y, Utahara R, Osato Y, Nitta K, Takeuchi T (1957) Production and isolation of a new antibiotic: kanamycin. J Antibiot 10:181–188 Umezawa H, Ueda M, Maeda K, Yagishita K, Kondo S, Okami Y, Utahara R, Osato Y, Nitta K, Takeuchi T (1957) Production and isolation of a new antibiotic: kanamycin. J Antibiot 10:181–188
5.
Zurück zum Zitat Bentley SD, Chater KF, Cerdeño-Tárraga AM, Challis GL, Thomson NR, James KD, Harris DE, Quail MA, Kieser H, Harper D, Bateman A, Brown S, Chandra G, Chen CW, Collins M, Cronin A, Fraser A, Goble A, Hidalgo J, Hornsby T, Howarth S, Huang CH, Kieser T, Larke L, Murphy L, Oliver K, O’Neil S, Rabbinowitsch E, Rajandream MA, Rutherford K, Rutter S, Seeger K, Saunders D, Sharp S, Squares R, Squares S, Taylor K, Warren T, Wietzorrek A, Woodward J, Barrell BG, Parkhill J, Hopwood DA (2002) Complete genome sequence of the model actinomycete Streptomyces coelicolor A3(2). Nature 417:141–147CrossRefPubMed Bentley SD, Chater KF, Cerdeño-Tárraga AM, Challis GL, Thomson NR, James KD, Harris DE, Quail MA, Kieser H, Harper D, Bateman A, Brown S, Chandra G, Chen CW, Collins M, Cronin A, Fraser A, Goble A, Hidalgo J, Hornsby T, Howarth S, Huang CH, Kieser T, Larke L, Murphy L, Oliver K, O’Neil S, Rabbinowitsch E, Rajandream MA, Rutherford K, Rutter S, Seeger K, Saunders D, Sharp S, Squares R, Squares S, Taylor K, Warren T, Wietzorrek A, Woodward J, Barrell BG, Parkhill J, Hopwood DA (2002) Complete genome sequence of the model actinomycete Streptomyces coelicolor A3(2). Nature 417:141–147CrossRefPubMed
6.
7.
Zurück zum Zitat Bode HB, Bethe B, Höfs R, Zeeck A (2002) Big effects from small changes: possible ways to explore nature’s chemical diversity. ChemBioChem 3:619–627CrossRefPubMed Bode HB, Bethe B, Höfs R, Zeeck A (2002) Big effects from small changes: possible ways to explore nature’s chemical diversity. ChemBioChem 3:619–627CrossRefPubMed
8.
Zurück zum Zitat Hosaka T, Ohnishi-Kameyama M, Muramatsu H, Murakami K, Tsurumi Y, Kodani S, Yoshida M, Fujie A, Ochi K (2009) Antibacterial discovery in actinomycetes strains with mutations in RNA polymerase or ribosomal protein S12. Nat Biotechnol 27:462–464CrossRefPubMed Hosaka T, Ohnishi-Kameyama M, Muramatsu H, Murakami K, Tsurumi Y, Kodani S, Yoshida M, Fujie A, Ochi K (2009) Antibacterial discovery in actinomycetes strains with mutations in RNA polymerase or ribosomal protein S12. Nat Biotechnol 27:462–464CrossRefPubMed
9.
Zurück zum Zitat Laureti L, Song L, Huanga S, Corre C, Leblond P, Challis GL, Aigle B (2011) Identification of a bioactive 51-membered macrolide complex by activation of a silent polyketide synthase in Streptomyces ambofaciens. Proc Natl Acad Sci Unit States Am 108:6258–6263CrossRef Laureti L, Song L, Huanga S, Corre C, Leblond P, Challis GL, Aigle B (2011) Identification of a bioactive 51-membered macrolide complex by activation of a silent polyketide synthase in Streptomyces ambofaciens. Proc Natl Acad Sci Unit States Am 108:6258–6263CrossRef
10.
Zurück zum Zitat Onaka H, Mori Y, Igarashi Y, Furumai T (2011) Mycolic acid-containing bacteria induce natural-product biosynthesis in Streptomyces species. Appl Environ Microbiol 77:400–406CrossRefPubMed Onaka H, Mori Y, Igarashi Y, Furumai T (2011) Mycolic acid-containing bacteria induce natural-product biosynthesis in Streptomyces species. Appl Environ Microbiol 77:400–406CrossRefPubMed
11.
Zurück zum Zitat Hoshino S, Zhang L, Awakawa T, Wakimoto T, Onaka H, Abe I (2015) Arcyriaflavin E, a new cytotoxic indolocarbazole alkaloid isolated by combined-culture of mycolic acid-containing bacteria and Streptomyces cinnamoneus NBRC 13823. J Antibiot 68:342–344CrossRef Hoshino S, Zhang L, Awakawa T, Wakimoto T, Onaka H, Abe I (2015) Arcyriaflavin E, a new cytotoxic indolocarbazole alkaloid isolated by combined-culture of mycolic acid-containing bacteria and Streptomyces cinnamoneus NBRC 13823. J Antibiot 68:342–344CrossRef
12.
Zurück zum Zitat Sugiyama R, Nishimura S, Ozaki T, Asamizu S, Onaka H, Kakeya H (2015) 5-Alkyl-1,2,3,4-tetrahydroquinolines, new membrane-interacting lipophilic metabolites, produced by combined culture of Streptomyces nigrescens and Tsukamurella pulmonis. Org Lett 17:1918–1921CrossRefPubMed Sugiyama R, Nishimura S, Ozaki T, Asamizu S, Onaka H, Kakeya H (2015) 5-Alkyl-1,2,3,4-tetrahydroquinolines, new membrane-interacting lipophilic metabolites, produced by combined culture of Streptomyces nigrescens and Tsukamurella pulmonis. Org Lett 17:1918–1921CrossRefPubMed
13.
Zurück zum Zitat Sakai K, Komaki H, Gonoi T (2015) Identification and Functional Analysis of the Nocardithiocin Gene Cluster in Nocardia pseudobrasiliensis. PLoS ONE 10:e0143264CrossRefPubMedPubMedCentral Sakai K, Komaki H, Gonoi T (2015) Identification and Functional Analysis of the Nocardithiocin Gene Cluster in Nocardia pseudobrasiliensis. PLoS ONE 10:e0143264CrossRefPubMedPubMedCentral
14.
Zurück zum Zitat Weber T, Blin K, Duddela S, Krug D, Kim HU, Bruccoleri R, Lee SY, Fischbach MA, Müller R, Wohlleben W, Breitling R, Takano E, Medema MH (2015) antiSMASH 3.0-a comprehensive resource for the genome mining of biosynthetic gene clusters. Nucl Acids Res 43:W237–243CrossRefPubMedPubMedCentral Weber T, Blin K, Duddela S, Krug D, Kim HU, Bruccoleri R, Lee SY, Fischbach MA, Müller R, Wohlleben W, Breitling R, Takano E, Medema MH (2015) antiSMASH 3.0-a comprehensive resource for the genome mining of biosynthetic gene clusters. Nucl Acids Res 43:W237–243CrossRefPubMedPubMedCentral
15.
Zurück zum Zitat Larkin MA, Blackshields G, Brown NP, Chenna R, McGettigan PA, McWilliam H, Valentin F, Wallace IM, Wilm A, Lopez R, Thompson JD, Gibson TJ, Higgins DG (2007) Clustal W and Clustal X version 2.0. Bioinformatics 23:2947–2948CrossRefPubMed Larkin MA, Blackshields G, Brown NP, Chenna R, McGettigan PA, McWilliam H, Valentin F, Wallace IM, Wilm A, Lopez R, Thompson JD, Gibson TJ, Higgins DG (2007) Clustal W and Clustal X version 2.0. Bioinformatics 23:2947–2948CrossRefPubMed
16.
Zurück zum Zitat Tamura K, Stecher G, Peterson D, Filipski A, Kumar S (2013) MEGA6: molecular evolutionary genetics analysis version 6.0. Mol Biol Evol 30:2725–2729CrossRefPubMedPubMedCentral Tamura K, Stecher G, Peterson D, Filipski A, Kumar S (2013) MEGA6: molecular evolutionary genetics analysis version 6.0. Mol Biol Evol 30:2725–2729CrossRefPubMedPubMedCentral
17.
Zurück zum Zitat Hoshino Y, Chiba K, Ishino K, Fukai T, Igarashi Y, Yazawa K, Mikami Y, Ishikawa J (2011) Identification of Nocobactin NA biosynthetic gene clusters in Nocardia farcinica. J Bacteriol 193:441–448CrossRefPubMed Hoshino Y, Chiba K, Ishino K, Fukai T, Igarashi Y, Yazawa K, Mikami Y, Ishikawa J (2011) Identification of Nocobactin NA biosynthetic gene clusters in Nocardia farcinica. J Bacteriol 193:441–448CrossRefPubMed
19.
Zurück zum Zitat Mukai A, Fukai T, Hoshino Y, Yazawa K, Harada K, Mikami Y (2009) Nocardithiocin, a novel thiopeptide antibiotic, produced by pathogenic Nocardia pseudobrasiliensis IFM 0757. J Antibiot 62:613–619CrossRef Mukai A, Fukai T, Hoshino Y, Yazawa K, Harada K, Mikami Y (2009) Nocardithiocin, a novel thiopeptide antibiotic, produced by pathogenic Nocardia pseudobrasiliensis IFM 0757. J Antibiot 62:613–619CrossRef
20.
Zurück zum Zitat O̅mura S, Eda S, Funayama S, Komiyama K, Takahashi Y, Woodruff B (1989) Studies on a novel antitumor antibiotic, phenazinomycin: taxonomy, fermentation, isolation, and physicochemical and biological characteristics. J Antibiot 42:1037–1042CrossRef O̅mura S, Eda S, Funayama S, Komiyama K, Takahashi Y, Woodruff B (1989) Studies on a novel antitumor antibiotic, phenazinomycin: taxonomy, fermentation, isolation, and physicochemical and biological characteristics. J Antibiot 42:1037–1042CrossRef
21.
Zurück zum Zitat Pridham TG, Anderson P, Foley C, Lindenfelser LA, Hessetime CW, Benedict RG (1956–1957) A selection of media for maintenance and taxonomic study of streptomycetes. Antibiot Annu 1956–1957:947–953 Pridham TG, Anderson P, Foley C, Lindenfelser LA, Hessetime CW, Benedict RG (1956–1957) A selection of media for maintenance and taxonomic study of streptomycetes. Antibiot Annu 1956–1957:947–953
22.
Zurück zum Zitat Sugie Y, Dekker KA, Hirai H, Ichiba T, Ishiguro M, Shiomi Y, Sugiura A, Brennan L, Duignan J, Huang LH, Sutcliffe J, Kojima Y (2001) CJ-15, 801, a novel antibiotic from a fungus, Seimatosporium sp. J Antibiot 54:1060–1065CrossRef Sugie Y, Dekker KA, Hirai H, Ichiba T, Ishiguro M, Shiomi Y, Sugiura A, Brennan L, Duignan J, Huang LH, Sutcliffe J, Kojima Y (2001) CJ-15, 801, a novel antibiotic from a fungus, Seimatosporium sp. J Antibiot 54:1060–1065CrossRef
23.
Zurück zum Zitat Nicolaou KC, Mathison CJN (2005) Synthesis of Imides, N-Acyl vinylogous carbamates and ureas, and nitriles by oxidation of amides and amines with Dess–Martin periodinane. Angew Chem Int Ed 44:5992–5997CrossRef Nicolaou KC, Mathison CJN (2005) Synthesis of Imides, N-Acyl vinylogous carbamates and ureas, and nitriles by oxidation of amides and amines with Dess–Martin periodinane. Angew Chem Int Ed 44:5992–5997CrossRef
24.
Zurück zum Zitat El-Tayeb O, Knight SG, Sih CJ (1964) Steroid epoxide cleavage by Cylindrocarpon radicicola. Biochim Biophys Acta 93:402–410CrossRefPubMed El-Tayeb O, Knight SG, Sih CJ (1964) Steroid epoxide cleavage by Cylindrocarpon radicicola. Biochim Biophys Acta 93:402–410CrossRefPubMed
25.
Zurück zum Zitat Makino T, Katsuyama Y, Otomatsu T, Misawa N, Ohnishi Y (2014) Regio- and stereospecific hydroxylation of various steroids at the 16α position of the D ring by the Streptomyces griseus cytochrome P450 CYP154C3. Appl Environ Microbiol 80:1371–1379CrossRefPubMedPubMedCentral Makino T, Katsuyama Y, Otomatsu T, Misawa N, Ohnishi Y (2014) Regio- and stereospecific hydroxylation of various steroids at the 16α position of the D ring by the Streptomyces griseus cytochrome P450 CYP154C3. Appl Environ Microbiol 80:1371–1379CrossRefPubMedPubMedCentral
26.
Zurück zum Zitat Choudhary MI, Sultan S, Khan MT, Yasin A, Shaheen F, Atta-ur-Rahman (2004) Biotransformation of (+)-androst-4-ene-3,17-dione. Nat Prod Res 18:529–535CrossRefPubMed Choudhary MI, Sultan S, Khan MT, Yasin A, Shaheen F, Atta-ur-Rahman (2004) Biotransformation of (+)-androst-4-ene-3,17-dione. Nat Prod Res 18:529–535CrossRefPubMed
27.
Zurück zum Zitat Le Pera A, Leggio A, Siciliano C, Di Gioia ML, Napoli A, Sindona G, Liguori A (2003) A straightforward chemical synthesis of 17-ketosteroids by cleavage of the C-17-dihydroxy acetone side chain in corticosteroids. Steroids 68:139–142CrossRefPubMed Le Pera A, Leggio A, Siciliano C, Di Gioia ML, Napoli A, Sindona G, Liguori A (2003) A straightforward chemical synthesis of 17-ketosteroids by cleavage of the C-17-dihydroxy acetone side chain in corticosteroids. Steroids 68:139–142CrossRefPubMed
28.
Zurück zum Zitat Komura K, Ozaki A, Ieda N, Sugi Y (2008) FeCl3·6H2O as a versatile catalyst for the esterification of steroid alcohols with fatty acids. Synthesis 21:3407–3410 Komura K, Ozaki A, Ieda N, Sugi Y (2008) FeCl3·6H2O as a versatile catalyst for the esterification of steroid alcohols with fatty acids. Synthesis 21:3407–3410
29.
Zurück zum Zitat Sugawara H, Ohyama A, Mori H, Kurokawa K (2009) Microbial genome annotation pipeline (MiGAP) for diverse users. In: the 20th International Conference on Genome Informatics (GIW2009) Poster and Software Demonstrations (Yokohama):S001–1–2 Sugawara H, Ohyama A, Mori H, Kurokawa K (2009) Microbial genome annotation pipeline (MiGAP) for diverse users. In: the 20th International Conference on Genome Informatics (GIW2009) Poster and Software Demonstrations (Yokohama):S001–1–2
30.
Zurück zum Zitat Altschul SF, Gish W, Miller W, Myers EW, Lipman DJ (1990) Basic local alignment search tool. J Mol Biol 215:403–410CrossRefPubMed Altschul SF, Gish W, Miller W, Myers EW, Lipman DJ (1990) Basic local alignment search tool. J Mol Biol 215:403–410CrossRefPubMed
Metadaten
Titel
Dehydropropylpantothenamide isolated by a co-culture of Nocardia tenerifensis IFM 10554T in the presence of animal cells
verfasst von
Yasumasa Hara
Midori A. Arai
Kanae Sakai
Naoki Ishikawa
Tohru Gonoi
Takashi Yaguchi
Masami Ishibashi
Publikationsdatum
05.12.2017
Verlag
Springer Singapore
Erschienen in
Journal of Natural Medicines / Ausgabe 1/2018
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-017-1161-y

Weitere Artikel der Ausgabe 1/2018

Journal of Natural Medicines 1/2018 Zur Ausgabe