Ochromonas danica
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ABSTRACT:
PROVIDER: PRJNA12717 | ENA |
REPOSITORIES: ENA
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Project description:Many halogenases interchangeably incorporate chlorine and bromine into organic molecules. On the basis of an unsubstantiated report that the alga Ochromonas danica, a prodigious producer of chlorosulfolipids, was able to produce bromosulfolipids, we have investigated the promiscuity of its halogenases toward bromine incorporation. We have found that bromosulfolipids are produced with the exact positional and stereochemical selectivity as in the chlorosulfolipid danicalipin A when this alga is grown under modified conditions containing excess bromide ion.
| S-EPMC6020021 | biostudies-literature
Project description:An EST project has begun for this organism
| PRJNA12748 | ENA
Project description:An EST project for this organism has begun
| PRJNA12690 | ENA
Project description:An EST project for this organism has begun
| PRJNA12703 | ENA
Project description:Golden brown chrysophyte algae capable of degrading phenol in axenic culture
| PRJNA12714 | ENA
Project description:An EST sequencing project has begun for this organism
| PRJNA12701 | ENA
Project description:The chlorosulfolipids are amphiphilic natural products with stereochemically complex patterns of chlorination and sulfation. Despite their role in toxic shellfish poisoning, potential pharmacological activities, and unknown biological roles, they remain understudied due to the difficulties in purifying them from natural sources. The structure of these molecules, with a charged sulfate group in the middle of the hydrophobic chain, appears incompatible with the conventional lipid bilayer structure. Questions about chlorosulfolipids remain unanswered partly due to the unavailability of structural analogues with which to conduct structure-function studies. We approach this problem by combining enantioselective total synthesis and membrane biophysics. Using a combination of Langmuir pressure-area isotherms of lipid monolayers, fluorescence imaging of vesicles, mass spectrometry imaging, natural product isolation, small-angle X-ray scattering, and cryogenic electron microscopy, we show that danicalipin A (1) likely inserts into lipid bilayers in the headgroup region and alters their structure and phase behavior. Specifically, danicalipin A (1) thins the bilayer and fluidizes it, allowing even saturated lipid to form fluid bilayers. Lipid monolayers show similar fluidizing upon insertion of danicalipin A (1). Furthermore, we show that the halogenation of the molecule is critical for its membrane activity, likely due to sterically controlled conformational changes. Synthetic unchlorinated and monochlorinated analogues do not thin and fluidize lipid bilayers to the same extent as the natural product. Overall, this study sheds light on how amphiphilic small molecules interact with lipid bilayers and the importance of stereochemistry and halogenation for this interaction.
| S-EPMC8557392 | biostudies-literature
Project description:An EST project has begun for this protist
| PRJNA12813 | ENA
Project description:An EST project has begun for this protist
| PRJNA12785 | ENA