- The development of a general strategy for the synthesis of tyramine-based natural products by using continuous flow techniques
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A flowing future! A multistep, general flow chemistry protocol has been developed for the preparation of tyramine-based natural products. The process integrates room-temperature reactions with high-temperature Heck coupling reactions, where the heat has been supplied by microwave irradiation. As a proof of concept for 'scaling out' to attain larger quantities of the desired products, the four primary tyramine-based natural products were prepared on a gram scale using this synthetic protocol.
- Achanta, Srinivas,Liautard, Virginie,Paugh, Robert,Organ, Michael G.
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supporting information; experimental part
p. 12797 - 12800
(2011/02/22)
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- Formation of hydroxycinnamoylamides and α-hydroxyacetovanillone in cell cultures of Solanum khasianum
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In elicitor-elicited photomixotrophic Solanum khasianum cell cultures, nine phenolic compounds accumulated in the cell culture medium. They were isolated and structurally identified at the cis- and trans-isomers of N-p- coumaroyloctopamine, N-feruloyloctopamine, N-p-coumaroyltyramine and N- feruloyltyramine as well as α-hydroxyacetovanillone. The cis-isomers of the hydroxycinnamoyl moieties were only formed during illumination of the cultures. The hydroxycinnamoylamides showed a transient accumulation with maximum values between 6 and 24 hr after elicitation, depending on the compound. The decrease of the compounds is very likely a peroxidase-mediated reaction.
- Muehlenbeck, Ute,Kortenbusch, Albertus,Barz, Wolfgang
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p. 1573 - 1579
(2007/10/03)
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- Inhibition of in vitro prostaglandin and leukotriene biosyntheses by cinnamoyl-β-phenethylamine and N-acyldopamine derivatives
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N-trans- and N-cis-Feruloyltyramines were isolated as the inhibitors of in vitro prostaglandin (PG) synthesis from an Indonesian medicinal plant, Ipomoea aquatica (Convolvulaceae). In order to clarify structure activity relationships, cinnamoyl-β-phenethylamines with possible combinations of naturally occurring cinnamic acids and β-phenethylamines were synthesized and tested for their inhibitory activities against PG synthetase and arachidonate 5-lipoxygenase. The compounds containing catechol groups such as N-caffeoyl-β-phenethylamine (CaP) showed higher inhibitory effects on PG synthetase. The catechol group was found to M essential for the inhibition of arachidonate 5-lipoxygenase. The investigation of concentration dependent effects on PG biosynthesis revealed that CaP enhanced PG biosynthesis at a lower concentration range, whereas it inhibited the reaction at a higher concentration. The effects of CaP on each reaction step were investigated with purified PG endoperoxide synthase and microsomal PG synthetase. CaP inhibited the cyclooxygenase reaction, while it enhanced the hydroperoxidase reaction. N-Acyldopamines which contain catechol and lipophylic group were synthesized from dopamine and fatty acids to test their inhibitory effects on arachidonate 5-lipoxygenase. N-Linoleoyldopamine was the most active compound and its IC50 value was 2.3 nM in our assay system, in which an IC50 value of AA 861, a specific inhibitor of 5-lipoxygenase, was 8 nM.
- Tseng,Iwakami,Mikajiri,Shibuya,Hanaoka,Ebizuka,Padmawinata,Sankawa
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p. 396 - 400
(2007/10/02)
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