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Hybrid biosynthesis of roseobacticides from algal and bacterial precursor molecules.

Seyedsayamdost MR, Wang R, Kolter R, Clardy J - J. Am. Chem. Soc. (2014)

Bottom Line: Roseobacticides are biosynthesized from the algal growth promoter, the major food molecule provided by the algal cells, and the algal senescence signal that initiates the mutualist-to-parasite switch.Thus, molecules that are beneficial during mutualism are diverted to the synthesis of toxins during parasitism.A plausible mechanism for assembling roseobacticides from these molecules is proposed.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Princeton University , Princeton, New Jersey 08544, United States.

ABSTRACT
Roseobacticides regulate the symbiotic relationship between a marine bacterium (Phaeobacter inhibens) and a marine microalga (Emiliania huxleyi). This relationship can be mutualistic, when the algal host provides food for the bacteria and the bacteria produce growth hormones and antibiotics for the algae, or parasitic, when the algae senesce and release p-coumaric acid. The released p-coumaric acid causes the bacteria to synthesize roseobacticides, which are nM-μM toxins for the algae. We examined the biosynthesis of roseobacticides and report that all roseobacticide precursors play critical roles during the mutualist phase of the symbiosis. Roseobacticides are biosynthesized from the algal growth promoter, the major food molecule provided by the algal cells, and the algal senescence signal that initiates the mutualist-to-parasite switch. Thus, molecules that are beneficial during mutualism are diverted to the synthesis of toxins during parasitism. A plausible mechanism for assembling roseobacticides from these molecules is proposed.

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ExpectedPatterns of Isotope Incorporation into Roseobacticide Bfrom 1,2-13C- and 11
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sch1: ExpectedPatterns of Isotope Incorporation into Roseobacticide Bfrom 1,2-13C- and 11


Hybrid biosynthesis of roseobacticides from algal and bacterial precursor molecules.

Seyedsayamdost MR, Wang R, Kolter R, Clardy J - J. Am. Chem. Soc. (2014)

ExpectedPatterns of Isotope Incorporation into Roseobacticide Bfrom 1,2-13C- and 11
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4227733&req=5

sch1: ExpectedPatterns of Isotope Incorporation into Roseobacticide Bfrom 1,2-13C- and 11
Bottom Line: Roseobacticides are biosynthesized from the algal growth promoter, the major food molecule provided by the algal cells, and the algal senescence signal that initiates the mutualist-to-parasite switch.Thus, molecules that are beneficial during mutualism are diverted to the synthesis of toxins during parasitism.A plausible mechanism for assembling roseobacticides from these molecules is proposed.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Princeton University , Princeton, New Jersey 08544, United States.

ABSTRACT
Roseobacticides regulate the symbiotic relationship between a marine bacterium (Phaeobacter inhibens) and a marine microalga (Emiliania huxleyi). This relationship can be mutualistic, when the algal host provides food for the bacteria and the bacteria produce growth hormones and antibiotics for the algae, or parasitic, when the algae senesce and release p-coumaric acid. The released p-coumaric acid causes the bacteria to synthesize roseobacticides, which are nM-μM toxins for the algae. We examined the biosynthesis of roseobacticides and report that all roseobacticide precursors play critical roles during the mutualist phase of the symbiosis. Roseobacticides are biosynthesized from the algal growth promoter, the major food molecule provided by the algal cells, and the algal senescence signal that initiates the mutualist-to-parasite switch. Thus, molecules that are beneficial during mutualism are diverted to the synthesis of toxins during parasitism. A plausible mechanism for assembling roseobacticides from these molecules is proposed.

Show MeSH