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. 2017 Nov 10;22(11):1935.
doi: 10.3390/molecules22111935.

Rapid Determination of Major Compounds in the Ethanol Extract of Geopropolis from Malaysian Stingless Bees, Heterotrigona itama, by UHPLC-Q-TOF/MS and NMR

Lingling Zhao  1   2 , Mengjiao Yu  3 , Minghui Sun  4 , Xiaofeng Xue  5 , Tongtong Wang  6 , Wei Cao  7 , Liping Sun  8
Affiliations

Rapid Determination of Major Compounds in the Ethanol Extract of Geopropolis from Malaysian Stingless Bees, Heterotrigona itama, by UHPLC-Q-TOF/MS and NMR

Lingling Zhao et al. Molecules. .

Abstract

A reliable, rapid analytical method was established for the characterization of constituents of the ethanol extract of geopropolis (EEGP) produced by Malaysian stingless bees-Heterotrigona itama-by combining ultra-high-performance liquid chromatography with quadruple time-of-flight mass spectrometry (UHPLC-Q-TOF/MS). Based on known standards, the online METLIN database, and published literature, 28 compounds were confirmed. Phenolic acids, flavones, triterpenes and phytosterol were identified or tentatively identified using characteristic diagnostic fragment ions. The results indicated that terpenoids were the main components of EEGP, accompanied by low levels of phenolic acids, flavonoids, and phytosterol. Two major components were further purified by preparative high-performance liquid chromatography (PHPLC) and identified by nuclear magnetic resonance (NMR) as 24(E)-cycloart-24-ene-26-ol-3-one and 20-hydroxy-24-dammaren-3-one. These two triterpenes, confirmed in this geopropolis for the first time, are potential chemical markers for the identification of geopropolis from Malaysian stingless bees, H. itama.

Keywords: Heterotrigona itama; UHPLC-Q-TOF/MS; geopropolis; stingless bees.

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Conflict of interest statement

The authors declare no conflicts of interest.

Figures

Figure 1
Figure 1
The total ion chromatograms from ultra-high-performance liquid chromatography with quadruple time-of-flight mass spectrometry (UHPLC-Q-TOF/MS) in positive mode.
Figure 2
Figure 2
(a) 1H-NMR and (b) 13 C-NMR spectral data of 24(E)-cycloart-24-ene-26-ol-3-one.
Figure 2
Figure 2
(a) 1H-NMR and (b) 13 C-NMR spectral data of 24(E)-cycloart-24-ene-26-ol-3-one.
Figure 3
Figure 3
The structure of 24(E)-cycloart-24-ene-26-ol-3-one.
Figure 4
Figure 4
(a) 1H-NMR and (b) 13C-NMR spectral data of 20-hydroxy-24-dammaren-3-one.
Figure 5
Figure 5
The structure of 20-hydroxy-24-dammaren-3-one.
See this image and copyright information in PMC

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