Synthesis of bis, tris and tetra(dihydrocaffeoyl)polyamine conjugates as antibacterial agents against VRSA

Yingyongnarongkul, Boon‐ek; Apiratikul, Nuttapon; Aroonrerk, Nuntana; Suksamrarn, Apichart

doi:10.1007/s12272-001-1215-4

Cited by 15 publications

(23 citation statements)

References 21 publications

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“…By analysis of the NMR spectroscopic data and comparison with the literature, the known compounds were respectively identified as N 1 , N 10 -bis(dihydrocaffeoyl)spermidine ( 2 ) [ 12 ], N - trans -coumaroyltyramine ( 3 ) [ 13 ], N - trans -feruloyltyramine ( 4 ) [ 14 ], N - trans -feruloyl 3′-O-methyldopamine ( 5 ) [ 15 ], N - trans -feruloyloctopamine ( 6 ) [ 14 ], N - cis -coumaroyltyramine ( 7 ) [ 16 ], N - cis -feruloyltyramine ( 8 ) [ 14 ], and N - cis -feruloyloctopamine ( 9 ) [ 14 ].…”

Section: Resultsmentioning

confidence: 99%

A Novel Flavonoid Glucoside from the Fruits of Lycium ruthenicun

Yan

Cheng

et al. 2018

Molecules

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A novel flavonoid glucoside, ruthenicunoid A (1), together with eight known substances, were isolated from the fruits of Lycium ruthenicun Murr. Their structures were elucidated by extensive spectroscopic data and chemical methods. Especially, the absolute configuration of glucose residue in 1 was assigned by acid hydrolysis followed by derivatization and GC analysis. Biological evaluation towards Sirtuin 1 (SIRT1) found that compounds 1 and 2 exhibit inhibitory activity against SIRT1 in a concentration-dependent manner, indicating its potential on SIRT1-associated disorders.

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Section: Resultsmentioning

confidence: 99%

A Novel Flavonoid Glucoside from the Fruits of Lycium ruthenicun

Yan

Cheng

et al. 2018

Molecules

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“…The elucidation and specific assignments of these compounds were in supporting information. Other known compounds are isolated as scopolamine3940 ( 1 ), anisodamine4142 ( 2 ), hyoscyamine4344 ( 3 ), anisodine31 ( 4 ), N-Caffeoylputrescine364546 ( 14 ), N1,N10-di-dihydrocaffeoylspermidine2147 ( 17 ), Scotanamine D21 (19), and N1-caffeoyl-N3-dihydrocaffeoyl spermidine48 ( 20 )…”

Section: Resultsmentioning

confidence: 99%

Discovery of new muscarinic acetylcholine receptor antagonists from Scopolia tangutica

Liu

Zhang

et al. 2017

Sci Rep

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Scopolia tangutica (S. tangutica) is a traditional Chinese medicinal plant used for antispasmodics, anesthesia, analgesia and sedation. Its pharmacological activities are mostly associated with the antagonistic activity at muscarinic acetylcholine receptors (mAchRs) of several known alkaloids such as atropine and scopolamine. With our recent identification of four hydroxycinnamic acid amides from S. tangutica, we hypothesized that this plant may contain previously unidentified alkaloids that may also contribute to its in vivo effect. Herein, we used a bioassay-guided multi-dimension separation strategy to discover novel mAchR antagonists from S. tangutica. The core of this approach is to use label-free cell phenotypic assay to first identify active fractions, and then to guide purification of active ligands. Besides four tropanes and six cinnamic acid amides that have been previously isolated from S. tangutica, we recently identified two new tropanes, one new cinnamic acid amide, and nine other compounds. Six tropane compounds purified from S. tangutica for the first time were confirmed to be competitive antagonists of muscarinic receptor 3 (M3), including the two new ones 8 and 12 with IC50 values of 1.97 μM and 4.47 μM, respectively. Furthermore, the cinnamic acid amide 17 displayed 15-fold selectivity for M1 over M3 receptors. These findings will be useful in designing lead compounds for mAchRs and elucidating mechanisms of action of S. tangutica.

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“…For example, spermidine hydroxycinnamate conjugates have antioxidant [31, 32], antibacterial [33], antiviral [34], insecticidal [35] and antiparasitic [36] activities. Other studies have demonstrated the inhibitory activity of polysubstituted p -coumaroyl polyamines on brain transporters for which a genetic polymorphism is associated with psychological disorders [37, 38].…”

Section: Resultsmentioning

confidence: 99%

Exploiting members of the BAHD acyltransferase family to synthesize multiple hydroxycinnamate and benzoate conjugates in yeast

et al. 2016

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BackgroundBAHD acyltransferases, named after the first four biochemically characterized enzymes of the group, are plant-specific enzymes that catalyze the transfer of coenzyme A-activated donors onto various acceptor molecules. They are responsible for the synthesis in plants of a myriad of secondary metabolites, some of which are beneficial for humans either as therapeutics or as specialty chemicals such as flavors and fragrances. The production of pharmaceutical, nutraceutical and commodity chemicals using engineered microbes is an alternative, green route to energy-intensive chemical syntheses that consume petroleum-based precursors. However, identification of appropriate enzymes and validation of their functional expression in heterologous hosts is a prerequisite for the design and implementation of metabolic pathways in microbes for the synthesis of such target chemicals.ResultsFor the synthesis of valuable metabolites in the yeast Saccharomyces cerevisiae, we selected BAHD acyltransferases based on their preferred donor and acceptor substrates. In particular, BAHDs that use hydroxycinnamoyl-CoAs and/or benzoyl-CoA as donors were targeted because a large number of molecules beneficial to humans belong to this family of hydroxycinnamate and benzoate conjugates. The selected BAHD coding sequences were synthesized and cloned individually on a vector containing the Arabidopsis gene At4CL5, which encodes a promiscuous 4-coumarate:CoA ligase active on hydroxycinnamates and benzoates. The various S. cerevisiae strains obtained for co-expression of At4CL5 with the different BAHDs effectively produced a wide array of valuable hydroxycinnamate and benzoate conjugates upon addition of adequate combinations of donors and acceptor molecules. In particular, we report here for the first time the production in yeast of rosmarinic acid and its derivatives, quinate hydroxycinnamate esters such as chlorogenic acid, and glycerol hydroxycinnamate esters. Similarly, we achieved for the first time the microbial production of polyamine hydroxycinnamate amides; monolignol, malate and fatty alcohol hydroxycinnamate esters; tropane alkaloids; and benzoate/caffeate alcohol esters. In some instances, the additional expression of Flavobacterium johnsoniae tyrosine ammonia-lyase (FjTAL) allowed the synthesis of p-coumarate conjugates and eliminated the need to supplement the culture media with 4-hydroxycinnamate.ConclusionWe demonstrate in this study the effectiveness of expressing members of the plant BAHD acyltransferase family in yeast for the synthesis of numerous valuable hydroxycinnamate and benzoate conjugates.Electronic supplementary materialThe online version of this article (doi:10.1186/s12934-016-0593-5) contains supplementary material, which is available to authorized users.

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Synthesis of bis, tris and tetra(dihydrocaffeoyl)polyamine conjugates as antibacterial agents against VRSA

Cited by 15 publications

References 21 publications

A Novel Flavonoid Glucoside from the Fruits of Lycium ruthenicun

A Novel Flavonoid Glucoside from the Fruits of Lycium ruthenicun

Discovery of new muscarinic acetylcholine receptor antagonists from Scopolia tangutica

Exploiting members of the BAHD acyltransferase family to synthesize multiple hydroxycinnamate and benzoate conjugates in yeast

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