TY - JOUR
T1 - Structural Elucidation of Cryptic Algaecides in Marine Algal-Bacterial Symbioses by NMR Spectroscopy and MicroED
AU - Park, Jong Duk
AU - Li, Yuchen
AU - Moon, Kyuho
AU - Han, Esther J.
AU - Lee, Seoung Rak
AU - Seyedsayamdost, Mohammad R.
N1 - Funding Information:
We are grateful to Dr. J. Schreiber, Dr. P. Shao, and Dr. N. Yao at the Princeton Imaging & Analysis Center and Dr. Lingbo Yu and Dr. Francis Reyes at Thermo‐Fisher for technical assistance and helpful discussions regarding MicroED; to Dr. Y.‐H. Shin at Harvard Medical School for assistance in calculating eCD spectra of sinatryptin B; to Jinseok Lee at Princeton University for assistance with analysis software; and to the National Institutes of Health (1R01GM140034 to M.R.S.), the Edward C. Taylor Third Year Graduate Fellowship in Chemistry (to J.‐D.P. and Y.L.), and a postdoctoral fellowship from the National Research Foundation of Korea (#2020R1A6A3A03037782 to S.R.L.) for financial support.
Publisher Copyright:
© 2021 Wiley-VCH GmbH
PY - 2022/1/21
Y1 - 2022/1/21
N2 - Microbial secondary metabolite discovery is often conducted in pure monocultures. In a natural setting, however, where metabolites are constantly exchanged, biosynthetic precursors are likely provided by symbionts or hosts. In the current work, we report eight novel and architecturally unusual secondary metabolites synthesized by the bacterial symbiont Phaeobacter inhibens from precursors that, in a native context, would be provided by their algal hosts. Three of these were produced at low titres and their structures were determined de novo using the emerging microcrystal electron diffraction method. Some of the new metabolites exhibited potent algaecidal activity suggesting that the bacterial symbiont can convert algal precursors, tryptophan and sinapic acid, into complex cytotoxins. Our results have important implications for the parasitic phase of algal-bacterial symbiotic interactions.
AB - Microbial secondary metabolite discovery is often conducted in pure monocultures. In a natural setting, however, where metabolites are constantly exchanged, biosynthetic precursors are likely provided by symbionts or hosts. In the current work, we report eight novel and architecturally unusual secondary metabolites synthesized by the bacterial symbiont Phaeobacter inhibens from precursors that, in a native context, would be provided by their algal hosts. Three of these were produced at low titres and their structures were determined de novo using the emerging microcrystal electron diffraction method. Some of the new metabolites exhibited potent algaecidal activity suggesting that the bacterial symbiont can convert algal precursors, tryptophan and sinapic acid, into complex cytotoxins. Our results have important implications for the parasitic phase of algal-bacterial symbiotic interactions.
UR - http://www.scopus.com/inward/record.url?scp=85120880671&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85120880671&partnerID=8YFLogxK
U2 - 10.1002/anie.202114022
DO - 10.1002/anie.202114022
M3 - Article
C2 - 34852184
AN - SCOPUS:85120880671
SN - 1433-7851
VL - 61
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 4
M1 - e202114022
ER -