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Stereochemistry and biological activity of chlorinated lipids: a study of danicalipin A and selected diastereomers.

ABSTRACT: The syntheses of (+)-16-epi- and (+)-11,15-di-epi-danicalipin A (2 and 3) are reported. The conformations of the parent diols 5 and 6 as well as the corresponding disulfates 2 and 3 were determined on the basis of J-based configuration analysis and supported by calculations. The impact of configuration on membrane permeability in Gram-negative bacteria and mammalian cell lines was assessed as well as cytotoxicity. Although diastereomer 2 showed similar behavior to natural (+)-danicalipin A (1), strikingly, the more flexible C11,C15-epimer 3 had no effect on permeability and proved equally or more toxic towards multiple cell lines.

SUBMITTER: Boshkow J

PROVIDER: S-EPMC5632803 | biostudies-other | 2017 Oct

REPOSITORIES: biostudies-other

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Stereochemistry and biological activity of chlorinated lipids: a study of danicalipin A and selected diastereomers.

Boshkow J J Fischer S S Bailey A M AM Wolfrum S S Carreira E M EM

Chemical science 20170809 10

The syntheses of (+)-16-epi- and (+)-11,15-di-epi-danicalipin A (2 and 3) are reported. The conformations of the parent diols 5 and 6 as well as the corresponding disulfates 2 and 3 were determined on the basis of J-based configuration analysis and supported by calculations. The impact of configuration on membrane permeability in Gram-negative bacteria and mammalian cell lines was assessed as well as cytotoxicity. Although diastereom ...[more]

PMID: 29147515

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Project description:Mentha species are widely used as food, medicine, spices, and flavoring agents. Thus, chemical composition is an important parameter for assessing the quality of mints. In general, the contents of menthol, menthone, eucalyptol, and limonene comprise one of the major parameters for assessing the quality of commercially important mints. Building further on the phytochemical characterization of the quality of Mentha species, this work was focused on the composition of phenolic compounds in methanolic extracts. Thirteen Mentha species were grown under the same environmental conditions, and their methanolic extracts were subjected to the LC-MS/MS (liquid chromatography-tandem mass spectrometry) profiling of phenolics and the testing their biological activities, i.e., antioxidant and tyrosinase inhibition activities, which are important features for the cosmetic industry. The total phenolic content (TPC) ranged from 14.81 ± 1.09 mg GAE (gallic acid equivalents)/g for Mentha cervina to 58.93. ± 8.39 mg GAE/g for Mentha suaveolens. The antioxidant activity of examined Mentha related with the content of the phenolic compounds and ranged from 22.79 ± 1.85 to 106.04 ± 3.26 mg TE (Trolox equivalents)/g for M. cervina and Mentha x villosa, respectively. Additionally, Mentha pulegium (123.89 ± 5.64 mg KAE (kojic acid equivalents)/g) and Mentha x piperita (102.82 ± 15.16 mg KAE/g) showed a strong inhibition of the enzyme tyrosinase, which is related to skin hyperpigmentation. The most abundant compound in all samples was rosmarinic acid, ranging from 1363.38 ± 8323 to 2557.08 ± 64.21 μg/g. In general, the levels of phenolic acids in all examined mint extracts did not significantly differ. On the contrary, the levels of flavonoids varied within the species, especially in the case of hesperidin (from 0.73 ± 0.02 to 109. 39 ± 2.01 μg/g), luteolin (from 1.84 ± 0.11 to 31.03 ± 0.16 μg/g), and kaempferol (from 1.30 ± 0.17 to 33.68 ± 0.81 μg/g). Overall results indicated that all examined mints possess significant amounts of phenolic compounds that are responsible for antioxidant activity and, to some extent, for tyrosinase inhibition activity. Phenolics also proved to be adequate compounds, together with terpenoids, for the characterization of Mentha sp. Additionally, citrus-scented Mentha x villosa could be selected as a good candidate for the food and pharmaceutical industry, especially due its chemical composition and easy cultivation, even in winter continental conditions.

Dataset Information

Stereochemistry and biological activity of chlorinated lipids: a study of danicalipin A and selected diastereomers.

Publications

Stereochemistry and biological activity of chlorinated lipids: a study of danicalipin A and selected diastereomers.

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