An improved synthesis for the (Z)-14-methyl-9-pentadecenoic acid and its topoisomerase I inhibitory activity

Carballeira, Néstor M.; Sanabria, David; Oyola, Delise

doi:10.3998/ark.5550190.0008.806

Cited by 6 publications

(4 citation statements)

References 12 publications

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“…Terminal alkynes with various substituents were easily available, unless deprotection of the TMS group of some substituted ethynyltrimethylsilane ( 3a – c ) was failed due to the volatile nature or side reactions. To solve this problem, tetrabutylammonium fluoride trihydrate (TBAF·3H 2 O) was added to the Sonogashira coupling reaction system to achieve the “one-pot” method …”

Section: Resultsmentioning

confidence: 99%

A Novel Approach toward Polyfulvene: Cationic Polymerization of Enediynes

Chen

Sun

et al. 2017

Macromolecules

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Enediyne compounds have found limited applications in polymer science and material chemistry due to the poor regioselectivity and/or the step-growth nature in their radical polymerizations. However, the cationic cyclization of enediynes exhibits a high regioselective 5-exo-dig mechanism, providing a new strategy for the synthesis of polyfulvene derivatives. The expected polymers were successfully produced by cationic polymerization of enediynes induced by CF 3 SO 3 H, and a well-defined conjugated structure was confirmed by NMR, IR, and UV−vis spectroscopy. GPC analysis shows a relatively narrow molecular weight distribution, and the molecular weight reaches up to 62.9 kDa. On the other hand, the structural features of the obtained polymers and the mechanism of the cationic polymerization were investigated through kinetic study and MALDI-TOF MS analysis, which revealed a second-order consumption of enediyne monomer and the polymerization being probably terminated through intramolecular abstraction of proton from the neighboring group.

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Section: Resultsmentioning

confidence: 99%

A Novel Approach toward Polyfulvene: Cationic Polymerization of Enediynes

Chen

Sun

et al. 2017

Macromolecules

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“…Cis-MUFA (C14–C22) have been shown to inhibit the enzyme topoisomerase I, a key enzyme in the breakdown and repair of DNA strands. The enzyme is necessary for topological changes in DNA for key cellular processes (replication, transcription, recombination) [ 57 ]. It seems that the decrease in C15:1 observed in the AKG group, a known bacterial FA, cannot be considered beneficial.…”

Section: Discussionmentioning

confidence: 99%

Cholesterol Content, Fatty Acid Profile and Health Lipid Indices in the Egg Yolk of Eggs from Hens at the End of the Laying Cycle, Following Alpha-Ketoglutarate Supplementation

Tomaszewska

Muszyński

Arczewska-Włosek

et al. 2021

Foods

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The current study aimed to assess the effects of dietary alpha-ketoglutarate (AKG) supplementation to laying hens on the fatty acid (FA) profile and cholesterol levels of the egg yolk at the end of production cycle. The experiment was performed on forty-eight Bovans Brown laying hens randomly assigned to either a control group (CONT) or a group supplemented with AKG. The CONT group was fed the basal diet, and the AKG group was fed the basal diet plus 1.0% AKG from the 31st until the 60th week of age, when FA profile, fat and cholesterol content of the egg yolks were determined. No significant changes in the cholesterol and total fat content of the egg yolks were observed. However, there were positive (the decrease in n-6 FA and the increase in MUFA), and negative (decrease in PUFA and n-3 FA, increase in TI and n-6/n-3 ratio) changes in FA profile following AKG supplementation. In conclusion, it was shown that dietary AKG after a 30-week long supplementation influence FA profile in egg yolk and its nutritional value.

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“…284 (Z)-14-Methyl-9-pentadecenoic acid, a metabolite of terrestrial 285 and marine bacteria 286 and of sponges, 287 was an inhibitor of human placental DNA topoisomerase I. 288 The known marine microbial metabolites, asperflavin 289,290 and tetrahydroauroclaucin 291 exhibited cytotoxicity against sex cells of the sea urchin Strongylocentrotus intermedius, 292 while the ubiquitous dinoflagellate carotenoid peridinin 293 induced apoptosis in apoptotic DLD-1 human colorectal cancer cells by activation of caspase-8 and caspase-9. 294 Pitipeptolide A from the cyanobacterium Lyngbya majuscula from Guam 295 was a feeding deterrent to urchins, two species of amphipods and small herbivorous crabs, 296 while lingshuiol, a polyhydroxy metabolite of the dinoflagellate Amphidinium sp., 297 exhibited potent membrane-permeabilising effects.…”

Section: Marine Microorganisms and Phytoplanktonmentioning

confidence: 99%

Marine natural products

et al. 2009

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This review covers the literature published in 2007 for marine natural products, with 948 citations(627 for the period January to December 2007) referring to compounds isolated from marine microorganisms and phytoplankton, green algae, brown algae, red algae, sponges, cnidarians,bryozoans, molluscs, tunicates, echinoderms and true mangrove plants. The emphasis is on new compounds (961 for 2007), together with the relevant biological activities, source organisms and country of origin. Biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.1 Introduction, 2 Reviews, 3 Marine microorganisms and phytoplankton, 4 Green algae, 5 Brown algae, 6 Red algae, 7 Sponges, 8 Cnidarians, 9 Bryozoans, 10 Molluscs, 11 Tunicates (ascidians),12 Echinoderms, 13 Miscellaneous, 14 Conclusion, 15 References.

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An improved synthesis for the (Z)-14-methyl-9-pentadecenoic acid and its topoisomerase I inhibitory activity

Cited by 6 publications

References 12 publications

A Novel Approach toward Polyfulvene: Cationic Polymerization of Enediynes

A Novel Approach toward Polyfulvene: Cationic Polymerization of Enediynes

Cholesterol Content, Fatty Acid Profile and Health Lipid Indices in the Egg Yolk of Eggs from Hens at the End of the Laying Cycle, Following Alpha-Ketoglutarate Supplementation

Marine natural products

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