Novel fatty acid esters of p-coumaryl alcohol in epicuticular wax of apple fruit

被引:42
作者
Whitaker, BD [1 ]
Schmidt, WF
Kirk, MC
Barnes, S
机构
[1] USDA ARS, Beltsville Agr Res Ctr, Produce Qual & Safety Lab, Inst Plant Sci, Beltsville, MD 20705 USA
[2] USDA ARS, Beltsville Agr Res Ctr, Environm Qual Lab, Anim & Nat Sci Inst, Beltsville, MD 20705 USA
[3] Univ Alabama, Dept Pharmacol & Toxicol, Birmingham, AL 35294 USA
[4] Univ Alabama, Ctr Comprehens Canc, Mass Spectrometry Shared Facil, Birmingham, AL 35294 USA
关键词
p-coumaryl alcohol; fatty acid esters; monolignol; epicuticular wax; apple fruit; Malus domestica;
D O I
10.1021/jf010409n
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
Hexane extracts of epicuticular wax from ev. Gala apples were noted to have an unusual, broad absorbance maximum at similar to 258 nm, which led us to isolate and identify the primary UV-absorbing compounds. Column and thin-layer chromatography yielded a fraction that gave a series of paired, 260-nm-absorbing peaks on C(18) HPLC. These were shown to be a family of phenolic fatty acid esters, for which retention times increased with increasing fatty acid chain length, and paired peaks were esters of two related phenolics with the same fatty acid moiety. Alkaline hydrolysis of the esters released two water-soluble phenolics separable by C(18) HPLC. Electrospray ionization mass spectrometry gave a molecular mass of 150 for both, and (1)H NMR plus U-V absorbance spectra identified them as E and Z isomers of p-coumaryl alcohol. Alkaline cleavage of the fatty acid esters in the presence of methanol or ethanol resulted in partial derivatization of E-p-coumaryl alcohol to the corresponding gamma -O-methyl or O-ethyl ether. Gradient HMQC NMR of the HPLC-purified stearate ester of E-p-coumaryl alcohol indicated that fatty acid esterification occurs at the gamma -OH rather than at the 4-OH on the phenyl ring. This is the first report of fatty acid esters of monolignols as a natural plant product.
引用
收藏
页码:3787 / 3792
页数:6
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