## 2 Results and Discussion
### Enantiomeric Distribution of Terpene Isomers  
Enantiomeric configuration and ratio are important in terms of organoleptic and biological properties [8; 29]. Also, the enetomeric distribution could be effectively applied to the recognition of honey authenticity [30]. In the present study, the optical isomers were separated into individual components at different chromatographic retention times using an enantioselective column. In particular, the following nine compounds were determined as enantiomeric isomers using a Cyclodex-B column: \(\alpha\)-pinene, sabinene, limonene, \(\beta\)-phellandrene, 4-terpineol, bornyl acetate, \(\gamma\)-muurolene, caryophyllene, and \(\gamma\)-curcumene. Chirality was identified for all of these enantiomers except for sabinene, \(\gamma\)-muurolene, and \(\gamma\)-curcumene, using authentic chiral standards or retention indices. All (5)-(\(-\))-isomers identified using Kovats retention index and/or positive identification were eluted prior to their corresponding (R)-(+)-isomers. The enantiomeric distribution of the nine chiral compounds in the three cultivars differed according to their chemotypes and according to the extraction method used with respect to the contents of oxygenated monoterenes and sesquiterpene hydrocarbons, but not monoterpene hydrocarbons (Table 4).The enantiomers of monoterechrocarbons were (\(-\))-\(\alpha\)-pinene (mh3), (\(+\))-\(\alpha\)-pinene (mh4), (\(+\) or \(-\))-sabinene (mh7), (\(+\) or \(-\))-sabinene (mh10), (\(-\))-limonene (mh17), (\(+\))-limonene (mh18), (\(-\))-\(\beta\)-phellandrene (mh19), and (\(+\))-\(\beta\)-phellandrene (mh20). In all cultivar samples, the predominant isomer of \(\alpha\)-pinene was expressed as the (\(+\))-configuration (mh4). Its enantiomeric excess was high in all samples, with the highest optical purity being observed for CO. Both mh7 and mh10 were only detected in CO and TO. Unfortunately, enantiomers of sabinene could not be positively identified based on the authentic chiral standard compounds used, and hence the predominant chirality could not be determined. The enantiomeric excess value of sabinene was 100%in CO, while it was below 50% in TO regardless of the extraction method. Furthermore, the optical configuration of limonene was not affected by the extraction method in all samples investigated, and a higher enantiomeric excess value was observed in CO for (\(+\))-isomer (91.52%-97.48%). The chiral activities of limonene, which is one of the major compounds in _Anethum sowa_, have been studied for psychological effects such as antibacterial and antifungal properties. (\(R\))-(\(+\))-Limonene induced an increase in systolic blood pressure with subjective alertness and restlessness of the nervous system, whereas inhalation of (\(-\))-isomer led to increased systolic blood pressure with no effects on psychological activity [8]. In terms of their odor properties on configuration, (+)-limonene is associated with the orange citrus odor of the _Citrus_ species, while its (\(-\))-isomer gives off the minty odor note of the _Mentha_ species [25]. [PERSON] and [PERSON] found that the enantiomeric ratios of chiral monoterpene hydrocarbons such as \(\alpha\)-pinene, camphene, \(\beta\)-pinene, and limonene did not differ significantly between using SD and SPME [29]. Consistent with that study, the enantiomeric excess values of \(\alpha\)-pinene and limonene in all cultivar samples in this study were not affected by the extraction method used. On the other hand, in the present study, the enantiomer distribution of \(\beta\)-phellandrene in CP differed between SD and SE. Interestingly, \(\beta\)-phellandrene was present as the (+)-form with low optical purity in the essential oils from CO, whereas the predominant isomer was the (-)-form in the other samples studied. Consequently, the differences of enantiomeric excess for monoterpene hydrocarbons, except for \(\beta\)-phellandrene, in three coniferous needle samples were not influenced by extraction methods.