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. 2025 Feb 21;14(5):659.
doi: 10.3390/plants14050659.

Gynoxys hallii Hieron., Gynoxys calyculisolvens Hieron., and Gynoxys azuayensis Cuatrec. Essential Oils-Chemical and Enantioselective Analyses of Three Unprecedented Volatile Fractions from the Ecuadorian Biodiversity

Yessenia E Maldonado  1 , María Del Carmen Rodríguez  2 , María Emilia Bustamante  2 , Stefanny Cuenca  2 , Omar Malagón  3 , Nixon Cumbicus  4 , Gianluca Gilardoni  3
Affiliations

Gynoxys hallii Hieron., Gynoxys calyculisolvens Hieron., and Gynoxys azuayensis Cuatrec. Essential Oils-Chemical and Enantioselective Analyses of Three Unprecedented Volatile Fractions from the Ecuadorian Biodiversity

Yessenia E Maldonado et al. Plants (Basel). .

Abstract

The present study is the first report on the chemical and enantiomeric compositions of essential oils from the Ecuadorian species Gynoxys hallii Hieron., Gynoxys calyculisolvens Hieron., and Gynoxys azuayensis Cuatrec. All the volatile fractions presented a sesquiterpene-based chemical profile, typical of other volatile fractions from this genus. Both qualitative (GC-MS) and quantitative (GC-FID) chemical analyses were carried out on two stationary phases of different polarity (non-polar and polar). The main constituents of G. hallii essential oil on the two columns, respectively, were α-pinene (33.6-31.5%), (E)-β-caryophyllene (6.2-6.4%), germacrene D (35.7-38.3%), and bicyclogermacrene (3.8-4.0%). In G. calyculisolvens, the major compounds were α-pinene (11.2-11.0%), p-cymene (4.0-3.7%), α-copaene (3.6-3.7%), (E)-β-caryophyllene (8.1-8.3%), germacrene D (20.8-22.0%), and germacrene D-4-ol (8.4-8.6%). Finally, the main components of G. azuayensis were α-pinene (4.5-4.1%), germacrene D (14.1-12.4%), bicyclogermacrene (2.6-3.0%), tridecanal (6.4-6.2%), and spathulenol (7.8-7.1%). Furthermore, enantioselective analyses were conducted on the three volatile fractions, using two stationary phases based on β-cyclodextrins. As a result, twelve chiral components were investigated, detecting both enantiomerically pure compounds and scalemic mixtures with various enantiomeric excess.

Keywords: Asteraceae; chiral separation; enantiomers; gas chromatography; mass spectrometry.

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Conflict of interest statement

The authors declare no conflicts of interest.

Figures

Figure 1
Figure 1
Compared GC–MS profiles of G. hallii (black), G. calyculisolvens (red), and G. azuayensis (blue) EOs on a 5% phenyl methylpolysiloxane stationary phase. The numbers refer to column N in Table 1.
Figure 2
Figure 2
Compared GC–MS profiles of G. hallii (black), G. calyculisolvens (red), and G. azuayensis (blue) EOs on a polyethylene glycol stationary phase. The numbers refer to column N in Table 1.
Figure 3
Figure 3
Molecular structures of the major compounds whose abundance is ≥3.0% on at least one column in at least one EO. According to Table 1, these molecules are α-pinene (2), p-cymene (15), α-copaene (64), (E)-β-caryophyllene (75), germacrene D (89), bicyclogermacrene (93), tridecanal (101), germacrene D-4-ol (108), and spathulenol (109).
Figure 4
Figure 4
Compared abundance of major compounds (≥3.0% in at least one oil) in the EOs of G. hallii (black), G. calyculisolvens (red), and G. azuayensis (blue). Abundances correspond to the mean values of the quantitative results on both columns.
Figure 5
Figure 5
Compared enantiomeric composition of some chiral compounds in the EOs of G. hallii (black), G. calyculisolvens (red), and G. azuayensis (blue).
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