Isolation and characterization of a novel lipid, 1(3),2-diacylglyceryl-(3)-O-4'-(N,N,N-trimethyl)homoserine, from Ochromonas danica

Brown, Anne; Elovson, John

doi:10.1021/bi00714a009

Cited by 77 publications

(10 citation statements)

References 29 publications

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“…As demonstrated in fig.2a [4]. In accordance with [4] our results are consistent with the structure shown in fig.3.…”

Section: Resultssupporting

confidence: 91%

“…Since molybdenum blue [11] and anthrone reagent [12] gave no reaction, both phosphorus and sugar are absent from lipid X unlike in known major lipids of green plants. However properties are very similar to lipid A detected in Ochromonas danica [3] and later shown to be 1 (3),2-diacylglyceryl-(3)-O-4'-(N,N,N-trime thyl) homoserine (DGTS) [4]. The aim of the work presented here was to demonstrate the identity of lipid A from Ochromonas and lipid X from Chlamydomonas.…”

Section: Resultssupporting

confidence: 51%

“…The results presented here demonstrate that the compound is identical with lipid A from Ochromonas danica [2~3], which has the structure of a diacylglyceryl-(3)-0-4'-(N,N,N-t rime thyl)-homoserine [4].…”

Section: Introductionmentioning

confidence: 57%

“…The demethylation was carried out as in [4] ; 0.23 g lipid X propionate were mixed with 1.2 g Na-benzenethiolate and 6 ml dioxane (distilled over LiAIH4) and the mixture refluxed for 1 h. The solvent was evaporated and the residue extracted with isopropanol. The residue of the isopropanol solution was acidified with conc.…”

Section: Demethylation Of Lipid X Propionatementioning

confidence: 99%

“…On a thin-layer chromatographic plate (solvent A), the R F value of the demethylated lipid X propionate was slightly greater than the one of lipid X propionate. For mass spectrometric analysis the demethylated alcohol component was silylated with pyridine-bis(trimethylsilyl)acetamide-trimethylsilyl chloride, 2:2:1 (v/v/v) for 30 min [4].…”

Section: Demethylation Of Lipid X Propionatementioning

confidence: 99%

See 4 more Smart Citations

Occurrence of 1(3),2‐diacylglyceryl‐(3)‐04′‐(N,N,N‐trimethyl)‐homoserine in Chlamydomonas reinhardi

Eichenberger

Boschetti

1978

FEBS Letters

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“…As demonstrated in fig.2a [4]. In accordance with [4] our results are consistent with the structure shown in fig.3.…”

Section: Resultssupporting

confidence: 91%

Section: Resultssupporting

confidence: 51%

Section: Introductionmentioning

confidence: 57%

Section: Demethylation Of Lipid X Propionatementioning

confidence: 99%

Section: Demethylation Of Lipid X Propionatementioning

confidence: 99%

See 3 more Smart Citations

Occurrence of 1(3),2‐diacylglyceryl‐(3)‐04′‐(N,N,N‐trimethyl)‐homoserine in Chlamydomonas reinhardi

Eichenberger

Boschetti

1978

FEBS Letters

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Nutraceutical Fatty Acid Production in Marine Microalgae and Cyanobacteria

Nilsson

Jiménez

Wulff

2020

Nutraceutical Fatty Acids From Oleaginous Microalgae

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Biological Investigations of (+)‐Danicalipin A Enabled Through Synthesis

2015

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At otal synthesis of the chlorosulfolipid (+ +)-danicalipin Ahas been accomplished in 12 steps and 4.4 %overall yield. The efficient and scalable synthesis enabled in-depth investigations of the lipids biological properties,i np articular cytotoxicity towards various mammalian cell lines.F urthermore,the ability of (+ +)-danicalipin Atoincrease the uptake of fluorophores into bacteria and mammalian cells was demonstrated, indicating it may enhance membrane permeability.By comparing (+ +)-danicalipin Aw ith racemic 1,14-docosane disulfate,a nd the diol precursor of (+ +)-danicalipin A, we have shown that both chlorine and sulfate functionalities are necessary for biological activity.Chlorosulfolipids are au nique family of natural lipids,t he first of which were isolated in the 1960s independently by the groups of Haines and Elovson from the fresh water alga Ochromonas danica.[1] Since then, several additional chlorosulfolipids have been isolated and characterized, namely malhamensilipin Af rom Poterioochromonas malhamensis [2] and mytilipin A-C ( Figure 1a)f rom unspecified, harmful microalgae,w hich accumulate in Mediterranean sea mussels Mytilus galloprovincialis rendering them toxic.[3] These chiral lipids are characterized by polychlorinated, sulfated aliphatic chains,s tructural features uncommon in nature.[4] Despite an umber of total syntheses of these structurally complex chlorosulfolipids, [5] little is known about their biological properties.H erein, we disclose as calable total synthesis of (+ +)-danicalipin A( 1)a nd evidence that this lipid has as ignificant effect on the membranes of mammalian cells and the walls of Gram-negative bacteria.Chlorosulfolipids are most abundant in O. danica,c ontributing to 14.4 %o ft he total lipid weight, whereas they account for only 2.3 %o ft he total lipid weight of P. malhamensis.[6] Furthermore,i nt he case of O. danica,t hese lipids comprise more than 80 mol %o ft he total polar lipid content of the entire cell. [7] This observation has led to the speculation that the larger contribution of the chlorinated lipids is related to an unspecified important role in membrane structure and function in O. danica.[1f]Most membrane lipids have well defined domains including hydrophilic heads and hydrophobic tails ( Figure 1b); these structural attributes enable formation of lipid bilayers through self-assembly.[8] Ac omparison of the conventional phospholipid structure to that of 1 reveals an umber of differences.F irstly,i nc ontrast to typical phospholipids, 1 is water soluble and highly polar. [1f, 9] This is presumably ac onsequence of the pair of anionic O-sulfates.S econdly, the charged domains of phospholipids are localized at one extremity of the lipid chain, which facilitates interaction between the extra-and/or intracellular space of the cell with the interior of the membrane.[8] Chlorosulfolipid 1 has two charged O-sulfates separated by an expanse of fourteen methylenes.I th as been proposed that the O-sulfate positioned towards the center of the lipi...

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Isolation and characterization of a novel lipid, 1(3),2-diacylglyceryl-(3)-O-4'-(N,N,N-trimethyl)homoserine, from Ochromonas danica

Cited by 77 publications

References 29 publications

Occurrence of 1(3),2‐diacylglyceryl‐(3)‐04′‐(N,N,N‐trimethyl)‐homoserine in Chlamydomonas reinhardi

Occurrence of 1(3),2‐diacylglyceryl‐(3)‐04′‐(N,N,N‐trimethyl)‐homoserine in Chlamydomonas reinhardi

Nutraceutical Fatty Acid Production in Marine Microalgae and Cyanobacteria

Biological Investigations of (+)‐Danicalipin A Enabled Through Synthesis

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