Isolation of sulfonosphingolipids from the rosette-inducing bacterium <i>Zobellia uliginosa</i> and evaluation of their rosette-inducing activity

Peng, Chia-Chi; Dormanns, Nils; Regestein, Lars; Beemelmanns, Christine

doi:10.1039/d3ra04314b

“…What factor in the media prepared from P. umbilicalis induces S. rosetta to develop into rosettes? We first thought the factor may come from a bacterium, for only bacterial cues have previously been described to induce rosette development 38,5,6,4,39 . Furthermore, P. umbilicalis can harbor the epiphytic bacteria Z. galactanivorans that induces rosette development 5 .…”

Section: Resultsmentioning

confidence: 99%

A red algal polysaccharide influences the multicellular development of the choanoflagellateSalpingoeca rosetta

Perotti,

Esparza,

Booth

2024

Preprint

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We uncovered an interaction between a choanoflagellate and alga, in which porphyran, a polysaccharide produced by the red alga Porphyra umbilicalis, induces multicellular development in the choanoflagellate Salpingoeca rosetta. We first noticed this possible interaction when we tested the growth of S. rosetta in media that was steeped with P. umbilicalis as a nutritional source. Under those conditions, S. rosetta formed multicellular rosette colonies even in the absence of any bacterial species that can induce rosette development. In biochemical purifications, we identified porphyran, a extracellular polysaccharide produced by red algae, as the rosette inducing factor The response of S. rosetta to porphyran provides a biochemical insight for associations between choanoflagellates and algae that have been observed since the earliest descriptions of choanoflagellates. Moreover, this work provides complementary evidence to ecological and geochemical studies that show the profound impact algae have exerted on eukaryotes and their evolution, including a rise in algal productivity that coincided with the origin of animals, the closest living relatives of choanoflagellates.

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Strukturrevision von Halisphingosin A durch Totalsynthese und Bioaktivitätsstudien

Sauer,

Kany,

Götze

et al. 2024

Angewandte Chemie

0

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Sphingoid bases are important bioactive lipids found in a variety of organisms, serving as the backbone of sphingolipids, which regulate essential physiological processes. Here we describe the total synthesis and structure revision of halisphingosine A, a sphingoid base initially isolated from marine sponges. To address inconsistencies in the NMR interpretation of this natural product, we developed a synthetic route involving a late‐stage enantioselective Henry reaction that allows access to multiple stereoisomers of the proposed halisphingosine core structure. Our library of 32 fully characterized synthetic stereoisomers enabled us to rectify the structure of halisphingosine A as (2R,3R,8R,Z)‐2‐aminooctadec‐9‐ene‐1,3,8‐triol, and to pursue further structure‐activity relation (SAR) studies regarding their antimicrobial and cytotoxic potential. In summary, our study offers a yet unreported compound library along with validated analytical datasets of marine sphingoid base derivatives, which significantly affects future ecometabolomic marine research and will facilitate the identification of inhibitors of sphingolipid metabolism or antagonists of sphingolipid base‐sensing receptors.

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Structure Revision of Halisphingosine A via Total Synthesis and Bioactivity Studies

Sauer,

Kany,

Götze

et al. 2024

Angew Chem Int Ed

0

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Sphingoid bases are important bioactive lipids found in a variety of organisms, serving as the backbone of sphingolipids, which regulate essential physiological processes. Here we describe the total synthesis and structure revision of halisphingosine A, a sphingoid base initially isolated from marine sponges. To address inconsistencies in the NMR interpretation of this natural product, we developed a synthetic route involving a late‐stage enantioselective Henry reaction that allows access to multiple stereoisomers of the proposed halisphingosine core structure. Our library of 32 fully characterized synthetic stereoisomers enabled us to rectify the structure of halisphingosine A as (2R,3R,8R,Z)‐2‐aminooctadec‐9‐ene‐1,3,8‐triol, and to pursue further structure‐activity relation (SAR) studies regarding their antimicrobial and cytotoxic potential. In summary, our study offers a yet unreported compound library along with validated analytical datasets of marine sphingoid base derivatives, which significantly affects future ecometabolomic marine research and will facilitate the identification of inhibitors of sphingolipid metabolism or antagonists of sphingolipid base‐sensing receptors.

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Isolation of sulfonosphingolipids from the rosette-inducing bacterium Zobellia uliginosa and evaluation of their rosette-inducing activity

Abstract: The choanoflagellate Salpingoeca rosetta transitions from unicellular to multicellular forms in the presence of bacterial signaling molecules, such as sulfonosphingolipids (RIFs).

Cited by 4 publications

References 26 publications

A red algal polysaccharide influences the multicellular development of the choanoflagellateSalpingoeca rosetta

A red algal polysaccharide influences the multicellular development of the choanoflagellateSalpingoeca rosetta

Strukturrevision von Halisphingosin A durch Totalsynthese und Bioaktivitätsstudien

Structure Revision of Halisphingosine A via Total Synthesis and Bioactivity Studies

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