دورية أكاديمية

Bacillimidazoles A-F, Imidazolium-Containing Compounds Isolated from a Marine Bacillus .

التفاصيل البيبلوغرافية
العنوان: Bacillimidazoles A-F, Imidazolium-Containing Compounds Isolated from a Marine Bacillus .
المؤلفون: Yan JX; Pharmaceutical Sciences Division, University of Wisconsin-Madison, 777 Highland Ave, Madison, WI 53705, USA., Wu Q; Pharmaceutical Sciences Division, University of Wisconsin-Madison, 777 Highland Ave, Madison, WI 53705, USA., Helfrich EJN; Harvard Medical School, Harvard University, 240 Longwood Ave, Boston, MA 02115, USA., Chevrette MG; Department of Bacteriology, University of Wisconsin-Madison, 1550 Linden Ave, Madison, WI 53706, USA., Braun DR; Pharmaceutical Sciences Division, University of Wisconsin-Madison, 777 Highland Ave, Madison, WI 53705, USA., Heyman H; Bruker Daltonics, Bruker Scientific LLC., 40 Manning Rd, Billerica, MA 01821, USA., Ananiev GE; The Small Molecule Screening Facility (SMSF), University of Wisconsin-Madison, 600 Highland Ave, Madison, WI 53792, USA., Rajski SR; Pharmaceutical Sciences Division, University of Wisconsin-Madison, 777 Highland Ave, Madison, WI 53705, USA., Currie CR; Department of Bacteriology, University of Wisconsin-Madison, 1550 Linden Ave, Madison, WI 53706, USA., Clardy J; Harvard Medical School, Harvard University, 240 Longwood Ave, Boston, MA 02115, USA., Bugni TS; Pharmaceutical Sciences Division, University of Wisconsin-Madison, 777 Highland Ave, Madison, WI 53705, USA.; The Small Molecule Screening Facility (SMSF), University of Wisconsin-Madison, 600 Highland Ave, Madison, WI 53792, USA.
المصدر: Marine drugs [Mar Drugs] 2022 Jan 01; Vol. 20 (1). Date of Electronic Publication: 2022 Jan 01.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: MDPI Country of Publication: Switzerland NLM ID: 101213729 Publication Model: Electronic Cited Medium: Internet ISSN: 1660-3397 (Electronic) Linking ISSN: 16603397 NLM ISO Abbreviation: Mar Drugs Subsets: MEDLINE
أسماء مطبوعة: Original Publication: Basel, Switzerland : MDPI, [2003]-
مواضيع طبية MeSH: Bacillus* , Porifera*, Anti-Bacterial Agents/*pharmacology, Animals ; Anti-Bacterial Agents/chemistry ; Aquatic Organisms ; Methicillin-Resistant Staphylococcus aureus/drug effects ; Microbial Sensitivity Tests
مستخلص: Chemical investigations of a marine sponge-associated Bacillus revealed six new imidazolium-containing compounds, bacillimidazoles A-F ( 1 - 6 ). Previous reports of related imidazolium-containing natural products are rare. Initially unveiled by timsTOF (trapped ion mobility spectrometry) MS data, extensive HRMS and 1D and 2D NMR analyses enabled the structural elucidation of 1 - 6 . In addition, a plausible biosynthetic pathway to bacillimidazoles is proposed based on isotopic labeling experiments and invokes the highly reactive glycolytic adduct 2,3-butanedione. Combined, the results of structure elucidation efforts, isotopic labeling studies and bioinformatics suggest that 1 - 6 result from a fascinating intersection of primary and secondary metabolic pathways in Bacillus sp. WMMC1349. Antimicrobial assays revealed that, of 1 - 6 , only compound six displayed discernible antibacterial activity, despite the close structural similarities shared by all six natural products.
References: Nat Prod Rep. 2016 Oct 26;33(11):1268-1317. (PMID: 27714029)
Angew Chem Int Ed Engl. 2014 Oct 20;53(43):11583-6. (PMID: 25197007)
Nat Prod Rep. 2013 Jun;30(6):869-915. (PMID: 23644572)
Org Lett. 2013 Jul 5;15(13):3262-5. (PMID: 23767821)
PLoS One. 2010 Jun 25;5(6):e11147. (PMID: 20593022)
J Nat Prod. 2003 Aug;66(8):1101-3. (PMID: 12932133)
J Nat Prod. 2004 May;67(5):817-22. (PMID: 15165143)
J Nat Prod. 2021 Jan 22;84(1):136-141. (PMID: 33337146)
Bioorg Med Chem Lett. 2010 Jan 15;20(2):581-5. (PMID: 20006501)
Molecules. 2016 Jan 26;21(2):150. (PMID: 26821008)
J Nat Prod. 2017 Sep 22;80(9):2551-2555. (PMID: 28840714)
J Nat Prod. 2009 Apr;72(4):696-9. (PMID: 19236031)
Anal Chem. 2012 May 15;84(10):4277-83. (PMID: 22519562)
Microbiome. 2017 Sep 15;5(1):116. (PMID: 28911333)
Nat Prod Rep. 2001 Feb;18(1):95-128. (PMID: 11245403)
Nat Prod Rep. 2002 Aug;19(4):454-76. (PMID: 12195812)
Angew Chem Int Ed Engl. 2020 Jul 13;59(29):12105-12112. (PMID: 32277730)
Nat Prod Rep. 2011 Jun;28(6):1143-91. (PMID: 21472175)
Biotechnol Biofuels. 2016 Dec 16;9:266. (PMID: 28018484)
J Am Chem Soc. 2019 Oct 30;141(43):17098-17101. (PMID: 31600443)
J Org Chem. 2011 Aug 19;76(16):6542-7. (PMID: 21736356)
mSystems. 2020 Aug 25;5(4):. (PMID: 32843538)
Nat Protoc. 2015 Jun;10(6):845-58. (PMID: 25950237)
Genome Res. 2017 May;27(5):722-736. (PMID: 28298431)
Org Lett. 2015 Mar 20;17(6):1529-32. (PMID: 25730523)
Nat Prod Rep. 2017 Mar 17;34(3):235-294. (PMID: 28290569)
Med Chem Res. 2015 Jul;24(7):2838-2861. (PMID: 26446298)
Mar Drugs. 2014 Feb 14;12(2):940-63. (PMID: 24534840)
J Am Chem Soc. 2013 Sep 11;135(36):13387-92. (PMID: 23984625)
Bioinformatics. 2010 Mar 15;26(6):841-2. (PMID: 20110278)
Bioorg Med Chem. 2014 Mar 1;22(5):1690-9. (PMID: 24508308)
J Nat Prod. 2004 Dec;67(12):2113-6. (PMID: 15620266)
Nucleic Acids Res. 2019 Jul 2;47(W1):W81-W87. (PMID: 31032519)
معلومات مُعتمدة: multiple funds through School of Pharmacy & the Graduate School University of Wisconsin-Madison; OIA-9977484 National Science Foundation; unknown United States Department of Agriculture; U19 AI109673 United States AI NIAID NIH HHS; RR02781 National Institute of Health; BIR-9214394 National Science Foundation; U19AI141720 United States NH NIH HHS; U19AI109673 National Institute of Health; Postdoctoral Mobility Fellowship Switzerland SNSF_ Swiss National Science Foundation; P41GM103399 National Institute of Health; U19 AI142720 United States AI NIAID NIH HHS; R01AT009874 National Institute of Health; RR08438 National Institute of Health; DMB-8415048 National Science Foundation
فهرسة مساهمة: Keywords: antibacterial; biosynthetic gene cluster; heterocycles; imidazolium; isotopic enrichment; marine-derived Bacillus
المشرفين على المادة: 0 (Anti-Bacterial Agents)
تواريخ الأحداث: Date Created: 20220120 Date Completed: 20220316 Latest Revision: 20230110
رمز التحديث: 20231215
مُعرف محوري في PubMed: PMC8779896
DOI: 10.3390/md20010043
PMID: 35049898
قاعدة البيانات: MEDLINE
الوصف
تدمد:1660-3397
DOI:10.3390/md20010043