Characterization of (E,E)-farnesol and its fatty acid esters from anal scent glands of nutria (Myocastor coypus) by gas chromatography-mass spectrometry and gas chromatography-infrared spectrometry

Characterization of (E,E)-farnesol and its fatty acid esters from anal scent glands of nutria (Myocastor coypus) by gas chromatography-mass spectrometry and gas chromatography-infrared spectrometry
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DOI:
10.1016/j.chroma.2007.06.041
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发表时间:
2007-09-21
影响因子:
4.1
通讯作者:
Attygalle, Athula B.
Attygalle, Athula B.
中科院分区:
化学2区
文献类型:
--
作者:
Lee, Hyeunjoo;Finckbeiner, Steven;Attygalle, Athula B.

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从海棠肛香腺的溶剂提取物中鉴定出几种挥发性化合物,包括萜类、脂肪醇、脂肪酸及其一些酯类化合物。Coypu),一种肆虐美国湿地的严重鼠害。通过气相色谱保留时间、电子电离(EI)、化学电离(CI)和化学电离(CI)质谱图的比较,确定主要的萜类成分为(E,E)-法呢醇及其酯类化合物。四种法尼醇异构体的电致电致发射光谱非常相似,然而,当从参考样品中编制高质量的质谱库并用于搜索时,ChemStation(Agilent)和GC-MS Solution(岛津)软件算法能够将天然化合物鉴定为(E,E)-异构体。类似地,这些酯被鉴定为(E,E)-法尼醇的酯。与电致发光光谱相反,(E,E)-和(EZ)-异构体的氯离子光谱明显不同于(ZE)-和(Z,Z)-异构体。CI谱中m/z137和121离子峰的强度(1)提供了一种确定Famesol的C-2双键构型的方法(对于2E异构体I-137和gt;I-121,而对于2Z异构体I-137和lt;I-121)。此外,(E,E)-异构体的红外光谱在2962-2968 cm(-1)和2918-2922 cm(-1)波段明显不同于其他三个异构体,它们分别代表CH3和CH的不对称伸缩振动。最后,用从正品中测定的法米索和金合欢酯异构体的GC保留指数来确认所有的鉴定。(C)2007年,爱思唯尔出版。
Several volatile compounds, including terpenoids, fatty alcohols, fatty acids and some of their esters, were identified from solvent extracts prepared from anal scent glands of nutria (a.k.a. coypu), a serious rodent pest ravaging wetlands in the USA. The major terpenoid constituents were identified as (E,E)-farnesol and its esters by a comparison of their gas chromatographic retention times, and electron-ionization (EI) and chemical-ionization (CI) mass spectra with those of authentic compounds. El mass spectra of the four farnesol isomers are very similar, however, the ChemStation (Agilent) and GC-MS Solution (Shimadzu) software algorithms were able to identify the natural compound as the (E,E)-isomer, when a high-quality mass spectral library was compiled from reference samples and used for searching. Similarly, the esters were identified as those of (E,E)-farnesol. In contrast to El spectra, the Cl spectra of the (E,E)- and (EZ)-isomers are distinctly different from those of the (ZE)- and (Z,Z)-isomers. The intensities (1) of the peaks for the m/z 137 and 121 ions in the CI spectra offer a way of determining the configuration of the C-2 double bond of famesols (for 2E isomers I-137 > I-121, whereas for 2Z isomers I-137 < I-121). Moreover, the infrared spectrum of the (E,E)-isomer is distinctly different from those of the other three isomers in the 2962-2968 cm(-1) and 2918-2922 cm(-1) bands, which represent asymmetric CH3 and CH stretching vibrations, respectively. Finally, the GC retention indices of famesol and farnesyl ester isomers determined from authentic samples were used to confirm all identifications. (c) 2007 Published by Elsevier B.V.