Synthesis of 1-Monoglycerides Having C11-20 Branched Chain Fatty Acids and Their Hemolysis Effects.

Xu, Ping; Usuki, Yoshinosuke; Akeda, Yukihiro; Taniguchi, Makoto

doi:10.7164/antibiotics.52.345

Cited by 3 publications

(3 citation statements)

References 6 publications

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“…155 Deprotection of 71a-g and 72a-b gave the desired products 58a-g and 59a-b in excellent yields. The characterisation data of all MAGs was in accordance with previously reported racemic iso-branched 167 and short chain 107,168,169 MAGs.…”

Section: Synthesis Of Sn-1 and Sn-3 Mags 58a-g And -Branched Mags 59...supporting

confidence: 89%

The Synthesis and Biological Evaluation of Ligands for C-Type Lectin Receptors

Khan¹

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<p>Macrophage inducible C-type lectin (Mincle), expressed on antigen presenting cells (APCs), is an important player in innate immunity due to its capacity to recognise pathogen-associated molecular patterns (PAMPs) and damage-associated molecular patterns (DAMPs), which are involved in pathogen recognition and in tissue homeostasis, respectively. Several ligands can bind Mincle and activate APCs to generate an inflammatory immune response, with prominent examples including the mycobacterial glycolipid, trehalose dimycolate (TDM), and the synthetic analogue thereof, trehalose dibehenate (TDB). Trehalose glycolipids exhibit anti-tumour properties and an ability to switch the phenotype of macrophages from one that is tumour promoting to one that is tumour suppressive. Insomuch, Mincle ligands have potential as adjuvants for both prophylactic and therapeutic (e.g. cancer) vaccines. Maradolipids, which were originally extracted from the nematode Caenorhabditis elegans, are glycolipids containing trehalose with symmetrical or asymmetrical iso-branched and straight chain fatty acids. The incorporation of the iso-branch makes them distinct from linear trehalose diesters (TDEs) and might provide the compounds with enhanced immunomodulatory properties. </p>

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Section: Synthesis Of Sn-1 and Sn-3 Mags 58a-g And -Branched Mags 59...supporting

confidence: 89%

The Synthesis and Biological Evaluation of Ligands for C-Type Lectin Receptors

Khan¹

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“…Bioactivity-guided fractionation of the MeOH extract has afforded four new acetylenic acids. 11 In our continuing study on the cytotoxic compounds of the same sponge, two new lysophosphatidylcholines (1,2) and four new monoglycerides (5)(6)(7)(8), together with two known monoglycerides (3, 4) 12,13 and two known ω-hydroxy fatty acid methyl esters, 14,15 were isolated. The isolation, structure elucidation, and cytotoxicity evaluation of these compounds are described herein.…”

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confidence: 99%

“…The known compounds 1- O -(13-methyltetradecanoyl)- sn -glycerol ( 3 ) and 1- O -pentadecanoyl- sn -glycerol ( 4 ) were identified by comparing the physical properties, 1 H NMR, and MS data with those reported. , The configuration at C-2 was established from the positive optical rotation, which is a general feature of the long-chain 1- O -acyl- sn -glycerols …”

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confidence: 99%

New Lysophosphatidylcholines and Monoglycerides from the Marine Sponge Stelletta sp.

et al. 2003

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Two new lysophosphatidylcholines (1, 2) and four new monoglycerides (5-8) were isolated from the marine sponge Stelletta sp. by bioactivity-guided fractionation. The planar structures of the new compounds were established on the basis of NMR and MS analyses. The stereochemistry was defined by comparison of the optical rotation. The compounds were evaluated for cytotoxicity against a small panel of five human tumor cell lines.

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