Synthesis of Diverse Hydroxycinnamoyl Phenylethanoid Esters Using Escherichia coli
7
Citation
34
Reference
10
Related Paper
Citation Trend
Abstract:
Caffeic acid phenethyl ester (CAPE) is an ester of a hydroxycinnamic acid (phenylpropanoid) and a phenylethanoid (2-phenylethanol; 2-PE), which has long been used in traditional medicine. Here, we synthesized 54 hydroxycinnamic acid-phenylethanoid esters by feeding 64 combinations of hydroxycinnamic acids and phenylethanols to Escherichia coli harboring the rice genes OsPMT and Os4CL. The same approach was applied for ester synthesis with caffeic acid and eight different phenyl alcohols. Two hydroxycinnamoyl phenethyl esters, p-coumaroyl tyrosol and CAPE, were also synthesized from glucose using engineered E. coli by introducing genes for the synthesis of substrates. Consequently, we synthesized approximately 393.4 mg/L p-coumaroyl tyrosol and 23.8 mg/L CAPE with this approach. Overall, these findings demonstrate that the rice PMT and 4CL proteins can be used for the synthesis of diverse hydroxycinnamoyl phenylethanoid esters owing to their promiscuity and that further exploration of the biological activities of these compounds is warranted.Keywords:
Phenylethanoid
Tyrosol
Phenylpropanoid
Hydroxycinnamic acid
Verbascoside
Caffeic acid phenethyl ester (CAPE) is an ester of a hydroxycinnamic acid (phenylpropanoid) and a phenylethanoid (2-phenylethanol; 2-PE), which has long been used in traditional medicine. Here, we synthesized 54 hydroxycinnamic acid-phenylethanoid esters by feeding 64 combinations of hydroxycinnamic acids and phenylethanols to Escherichia coli harboring the rice genes OsPMT and Os4CL. The same approach was applied for ester synthesis with caffeic acid and eight different phenyl alcohols. Two hydroxycinnamoyl phenethyl esters, p-coumaroyl tyrosol and CAPE, were also synthesized from glucose using engineered E. coli by introducing genes for the synthesis of substrates. Consequently, we synthesized approximately 393.4 mg/L p-coumaroyl tyrosol and 23.8 mg/L CAPE with this approach. Overall, these findings demonstrate that the rice PMT and 4CL proteins can be used for the synthesis of diverse hydroxycinnamoyl phenylethanoid esters owing to their promiscuity and that further exploration of the biological activities of these compounds is warranted.
Phenylethanoid
Tyrosol
Phenylpropanoid
Hydroxycinnamic acid
Verbascoside
Cite
Citations (7)
Verbascoside
Cite
Citations (373)
Twenty-one samples of Sideritis species (S. scardica, S. raeseri, S. taurica, S. syriaca and S. perfoliata) from various locations on the Balkan Peninsula were evaluated for their chemical constituents. Chemical analyses were focused on secondary metabolites, particularly phenolic compounds, which have several roles in the plant physiological processes and have demonstrated significant health beneficial effects. The occurrence of hydroxycinnamic acids, phenylethanoid glycosides and flavonoids has been investigated in taxonomically related taxa of the genus Sideritis. A systematic method for phenolic compounds identification was developed using tandem mass spectrometry coupled to high performance liquid chromatography with diode array detection. Scanning for precursor ions of commonly found phenolics in Sideritis species using LC/MS11 with an ion trap instrument permitted the specific determination of hydroxycinnamic acid derivatives, and phenylethanoid and flavonoid glycosides. Further characterization of each phenolic compound was performed using MS/MS product-ion analysis and common-neutral-loss analysis. This on-line technique allowed identification of three hydroxycinnamic acid derivatives, eight phenylethanoid glycosides, and twenty-four flavonoid glycosides. All the taxa analysed produced very similar phenolic patterns characterized by the presence of 5-caffeoylquinic acid, lavandulifolioside, verbascoside, hypolaetin 7-O-[6'''-O-acetyl]-allosyl(1-->2)glucoside, apigenin 7-(4"-p-coumaroylglucoside), 4'-O-methylisoscutellarein 7-O-[6'''-O-acetyl]-allosyl(1-->2)glucoside, and minor amounts of isoverbascoside, apigenin 7-O-allosyl(1-->2)glucoside, isoscutellarein 7-O-allosyl-(1-->2)-[6"-O-acetyl]-glucoside, hypolaetin 7-O-allosyl-(1-->2)-[6"-O-acetyl]-glucoside and 4'-O-methylhypolaetin 7-O-[6'''-O-acetyl]-allosyl-(1-->2)-[6"-O-acetyl]-glucoside. These results show that the investigated species are systematically very closely related. Phenylethanoid glycosides and flavonoid acetylglycosides are dominant and constitute 90% of the total phenolic compounds compared with hydroxycinnamic acid and flavonoid 7-O-glycosides. Principal component analysis (PCA) was performed for the nature and content of the different compounds to be correlated to the particular Sideritis species and also to the locations.
Verbascoside
Phenylethanoid
Hydroxycinnamic acid
Glucoside
Cite
Citations (49)
Abstract From the aerial parts of Phlomis longifolia var. longifolia four iridoid glucosides, shanzhiside methyl ester (1), 5-deoxypulchelloside I (2), lamalbide (3), phlomiol (4) and three phenylethanoid glycosides, verbascoside (5), forsythoside B (6). leucosceptoside A (7) along with the caffeic acid ester, chlorogenic acid (8) were isolated. The structures of the isolated compounds were established by spectroscopic (UV, IR, ID- and 2D-NMR, FABMS) and chemical evidence. The structure elucidation of the iridoid compounds 2 and 3 are discussed in detail. Key Words: Phlomis longifolia var. longifolia LamiaceaeIridoidsPhenylethanoids
Phenylethanoid
Verbascoside
Glucoside
Cite
Citations (17)
Phenylethanoid
Verbascoside
Glucoside
Cite
Citations (4)
新 phenylethanoid glycoside ， sculponiside ( 1 )从 Isodon sculponeatus ( Vaniot )的天线部分被孤立名声与六已知的混合物 martynoside ( 2 )一起， verbascoside ( 3 )，(+) -hydroxypinoresinol-8-O--d-glucoside ( 4 )， cedrusin ( 5 )， 7-megastigmene-3S,5R,6R,7E,9S-tetrol ( 6 )和 4-oxo--ionol--d-glucopyranoside ( 7 )。他们的化学结构从物理化学的数据并且由酸的水解作用被阐明。
Phenylethanoid
Verbascoside
Glucoside
Cite
Citations (0)
From the aerial parts of Verbascum salviifolium Boiss., 2 neolignan glucosides, dehydrodiconiferyl alcohol-9'-O-b -D-glucopyranoside (1) and dehydrodiconiferyl alcohol-9-O-b- D-glucopyranoside (2), along with 5 phenylethanoid glycosides, acteoside (= verbascoside) (3), b -hydroxyacteoside (4), forsythoside B (5), angoroside A (6) and martynoside (7), were isolated. The structure elucidation of the isolated compounds was established on the basis of spectroscopic evidence. Compounds 1-7 demonstrated scavenging properties toward the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical in TLC autographic and spectroscopic assays.
Phenylethanoid
Verbascoside
Glucoside
Cite
Citations (21)
Phenylethanoid
Verbascoside
Aucubin
Moiety
Plantaginaceae
Glucoside
Cite
Citations (25)
Four phenylethanoid glucosides were isolated from the flower of Buddleja officinalis. On the basis of specteral data, they were identified as salidroside(1), verbascoside(2), isoverbascoside(3) and echinacoside(4). Compounds 1, 3 and 4 were obtained from the plant for the first time. Compound 2 showed antibacterial and anticancer activities.
Phenylethanoid
Verbascoside
Flos
Glucoside
Cite
Citations (4)
Verbascoside
Phenylethanoid
Glucoside
Anti-inflammatory
Cite
Citations (94)