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Genome-based discovery and total synthesis of janustatins, potent cytotoxins from a plant-associated bacterium (Record no. 1663)

MARC details
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100 10 - MAIN ENTRY--PERSONAL NAME
Personal name Ueoka, Reiko
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9 (RLIN) 1375
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Title Genome-based discovery and total synthesis of janustatins, potent cytotoxins from a plant-associated bacterium
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Date of publication, distribution, etc. 2022-09-05.
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General note /pmc/articles/PMC7613652/
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General note /pubmed/36064972
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Summary, etc. Host-associated bacteria are increasingly recognized as underexplored sources of bioactive natural products with unprecedented chemical scaffolds. A recently identified example is the plant root-associated marine bacterium Gynuella sunshinyii of the chemically underexplored order Oceanospirillales. Its genome contains at least 22 biosynthetic gene clusters suggesting a rich and mostly uncharacterized specialized metabolism. In this work, in silico chemical prediction of a non-canonical polyketide synthase cluster led to the discovery of janustatins, structurally unprecedented polyketide alkaloids with potent cytotoxicity that are produced at minute quantities. A combination of MS and 2D NMR experiments, density functional theory calculations of (13)C chemical shifts, and semiquantitative interpretation of T-ROESY data were conducted to determine the relative configuration, which enabled the total synthesis of both enantiomers and assignment of the absolute configuration. Janustatins feature a previously unknown pyridodihydropyranone heterocycle and an unusual biological activity consisting of delayed, synchronized cell death at subnanomolar concentrations.
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Terms governing use and reproduction
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Terms governing use and reproduction https://www.springernature.com/gp/open-research/policies/accepted-manuscript-termsUsers may view, print, copy, and download text and data-mine the content in such documents, for the purposes of academic research, subject always to the full Conditions of use: https://www.springernature.com/gp/open-research/policies/accepted-manuscript-terms
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Language note en
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Topical term or geographic name as entry element Article
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Genre/form data or focus term Text
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Personal name Sondermann, Philipp
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9 (RLIN) 1376
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Personal name Leopold-Messer, Stefan
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9 (RLIN) 1377
700 10 - ADDED ENTRY--PERSONAL NAME
Personal name Liu, Yizhou
Relator term author
9 (RLIN) 1378
700 10 - ADDED ENTRY--PERSONAL NAME
Personal name Suo, Rei
Relator term author
9 (RLIN) 1379
700 10 - ADDED ENTRY--PERSONAL NAME
Personal name Bhushan, Agneya
Relator term author
9 (RLIN) 1380
700 10 - ADDED ENTRY--PERSONAL NAME
Personal name Vadakumchery, Lida
Relator term author
9 (RLIN) 1381
700 10 - ADDED ENTRY--PERSONAL NAME
Personal name Greczmiel, Ute
Relator term author
9 (RLIN) 1382
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Personal name Yashiroda, Yoko
Relator term author
9 (RLIN) 1383
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Personal name Kimura, Hiromi
Relator term author
9 (RLIN) 1384
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Personal name Nishimura, Shinichi
Relator term author
9 (RLIN) 1385
700 10 - ADDED ENTRY--PERSONAL NAME
Personal name Hoshikawa, Yojiro
Relator term author
9 (RLIN) 1386
700 10 - ADDED ENTRY--PERSONAL NAME
Personal name Yoshida, Minoru
Relator term author
9 (RLIN) 1387
700 10 - ADDED ENTRY--PERSONAL NAME
Personal name Oxenius, Annette
Relator term author
9 (RLIN) 1388
700 10 - ADDED ENTRY--PERSONAL NAME
Personal name Matsunaga, Shigeki
Relator term author
9 (RLIN) 1389
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Personal name Williamson, R. Thomas
Relator term author
9 (RLIN) 1390
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Personal name Carreira, Erick M.
Relator term author
9 (RLIN) 1391
700 10 - ADDED ENTRY--PERSONAL NAME
Personal name Piel, Jörn
Relator term author
9 (RLIN) 1392
786 0# - DATA SOURCE ENTRY
Note Nat Chem
856 41 - ELECTRONIC LOCATION AND ACCESS
Uniform Resource Identifier <a href="http://dx.doi.org/10.1038/s41557-022-01020-0">http://dx.doi.org/10.1038/s41557-022-01020-0</a>
Public note Connect to this object online.

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