The essential oil composition of selected Hemerocallis cultivars and their biological activity

Katarzyna Szewczyk 1 , Danuta Kalemba 2 , Małgorzata Miazga-Karska 3 , Barbara Krzemińska 1 , Agnieszka Dąbrowska 4 ,  and Renata Nowak 1
  • 1 Department of Pharmaceutical Botany, Medical University of Lublin, Lublin, Poland
  • 2 Lodz University of Technology, Institute of Natural Products and Cosmetics, Łódź, Poland
  • 3 Department of Biochemistry and Biotechnology; Medical University of Lublin, Lublin, Poland
  • 4 Botanical Garden of Lublin; University of Maria Sklodowska-Curie, Lublin, Poland
Katarzyna Szewczyk, Danuta Kalemba
  • Lodz University of Technology, Institute of Natural Products and Cosmetics, Łódź, Poland
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, Małgorzata Miazga-Karska
  • Department of Biochemistry and Biotechnology; Medical University of Lublin, Lublin, Poland
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, Barbara Krzemińska, Agnieszka Dąbrowska and Renata Nowak

Abstract

The horticultural cultivars of Hemerocallis (daylily) have been used to treat diseases such as insomnia, inflammation and depression, and also as a vegetable in eastern Asia. Taking into consideration the fact, that the volatile compounds in Hemerocallis cultivars have not been investigated to date, we decided to study the composition of the essential oils (EOs) from the aerial parts of ten varieties collecting in Poland. EOs, obtained by hydrodistillation, were analyzed by GC/MS method that resulted in identification of 23-36 volatile compounds comprising 89.5%–96.3% of the total amount. The essential oils differed in their composition and they can be classified into three groups. The antibacterial and antioxidant activities of EOs were also evaluated. Gram-negative strains were most strongly inhibited by all tested oils. Two model systems have been used for the antioxidant efficacy, 2,2-diphenyl-1-picryl-hydrazyl (DPPH•) andβ-carotene bleaching assays. The essential oils with the high presence of oxygenated monoterpenes and monoterpene hydrocarbons showed higher antioxidant activity. The chemical composition of EOs of Hemerocallis cultivars and their biological activity is reported for the first time. Thus, the findings presented here suggest that the aerial parts of Hemerocallis cultivars may be candidates for the development of new phytomedicine.

1 Introduction

The essential oil-producing species are extensively arranged among the plant kingdom. The volatile compounds are not only important in plant physiology but also in pharmaceutical, food and cosmetics industries. Numerous studies showed that essential oils possess therapeutic properties and can prevent and cure many diseases [1].

The genus Hemerocallis, belonging to Asphodelaceae family (Hemerocallidoideae subfamily), is mainly of East Asia origin and contains hardy plants surviving from North American Zones [2]. According to the American Daylily Society [3], more than 80 000 Hemerocallis cultivars exist in the world. They have usually been created by interspecific, intraspecific or interploidy cross [4,5]. These perennial plants are cultivated as ornamental species in Europe and America, as well as important ingredients in food and traditional medicine [6, 7, 8]. Crude extracts of daylilies have been used in Asia as diuretic, anthelmintic, antiemetic, antispasmodic, sedative and antiphlogistic remedies [9, 10, 11]. From the aerial parts and roots of these plants various kinds of constituents including polyphenols [12, 13, 14, 15], carotenoids [8], anthraquinones [9], naphthalene glycosides [6], steroidal saponins [16], and lactams [17,18], have been isolated. The pharmacological studies have shown that Hemerocallis species demonstrate the biological activities, such as antioxidant [6,14,19, 20, 21], neurological [22], cytoprotection [10], anti-inflammatory [23,24], antidepressant [25,26], and anticancer [27].

To the best of our knowledge, there is only one report on chemical composition of the essential oils of Hemerocallis. Consequently, the purpose of the present research was carried out to investigate the chemical composition, and also antioxidant and antibacterial activities of the essential oils of the aerial parts of ten Hemerocallis cultivars.

2 Experimental

2.1 Plant material and essential oils isolation

Flowers, leaves and stems of ten Hemerocallis cultivars, as shown in Table 1, were collected in the Maria Curie-Skłodowska University (UMCS) Botanical Garden in Lublin (Poland), at altitude of 181.2 m a.s.l. (coordinates 51°15’46” N; 22°30’51” E) in August 2017, in their full flowering phase. Taxonomical identification was confirmed by Dr. A. Dąbrowska.

Table 1

Hemerocallis cultivars used in the experiment for EOs determination. *Year of introduction to cultivation in Botanical Garden in Lublin (Poland).

Inventory no.NameOriginYear*
2427Hemerocallis citrina BaroniBotanical Garden of the Adam Mickiewicz University in Poznań, Poland

52°25’11’’ N; 16°52’55’’ E
1967
75Hemerocallis fulva (L.) L.

(Hemerocallis fulva (L.) L. var. kwanso Regel)
Botanical Garden of the Adam Mickiewicz University in Poznań, Poland

52°25’11’’ N; 16°52’55’’ E
1967
243Hemerocallis ‘Aten’Private collection, Chocznia near/ Andrychów, Poland

49°51’51’’ N; 19°26’39’’ E
1981
158/2004Hemerocallis ‘Bożena’Arboretum Wojsławice, Poland

50°42’40’’ N; 16°51’18’’ E
2004
297Hemerocallis ‘Catherine Woodbuery’Private collection, Chocznia near/ Andrychów, Poland

49°51’51’’ N; 19°26’39’’ E
1981
3/2008Hemerocallis ‘Chicago Apache’Garden Center, Zemborzycka Street, Lublin, Poland

2008
156/2004Hemerocallis ‘Danuta’Arboretum Wojsławice, Poland

50°42’40’’ N; 16°51’18’’ E
2004
96/2014Hemerocallis ‘Jaskółka’Arboretum Wojsławice, Poland

50°42’40’’ N; 16°51’18’’ E
2014
396Hemerocallis ‘Pink Solace’Botanical Garden in Powsin, Poland

52°06’16’’ N; 21°05’42’’ E
1989
249Hemerocallis ‘Rebel Cause’Botanical Garden in Powsin, Poland

52°06’16’’ N; 21°05’42’’ E
1983

The plants were dried in a drying chamber at 35°C, immediately after the harvest. The essential oils were obtained by 4-h hydrodistillation using the Clevenger apparatus. The ratio of dried material and distilled water was 1:7 (weight/volume). The weight of essential oils was measured after the process and according to the formula described in our previous study [28]. The oil yields are given in Table 2 and 3.

Table 2

Composition of essentials oils of Hemerocallis cultivars aerial parts: 2H. citrina Baroni; 7H. ‘Pink Solace’; 8H. ‘Bożena’; 9H. ‘Jaskółka’. RIexp, experimental retention index; RIlit, literature retention index; t, trace – percentage value less than 0.05%; n.i., not identified.

No.ConstituentRIexpRIlit2789Class of compound
Content [%]
furfuryl alcohol8428440.1---O
α-thujene9309320.1-0.10.1MTH
α-pinene9319341.40.51.91.9MTH
camphene947950tt0.1tMTH
sabinene9689730.50.20.40.5MTH
β-pinene9709780.60.20.60.7MTH
myrcene9839820.2t0.10.1MTH
p-cymene91510150.10.7t1.4MTH
1,8-cineole1025102483.473.785.583.7MTO
limonene10261025t2.2ttMTH
trans-linalool oxide10601062t-t-MTO
cis-linalool oxide10731072t-t-
linalool108610870.20.30.20.1MTO
trans-pinocarveol113511370.10.20.10.1MTO
δ-terpineol115211550.10.2-0.1MTO
terpinen-4-ol116211640.91.50.80.8MTO
α-terpineol117811784.211.33.73.4MTO
carvone121512140.10.1ttMTO
geranial124212450.2t0.2tMTO
α-terpinyl acetate133313331.43.51.11.1MTO
n.i. 79, 109, 91,1351336-1.81.0t0.3
β-caryophyllene14161418t0.1ttSTH
geranylacetone14281430t---STH
aromadendrene14391443t0.10.10.1STH
bicyclogermacrene14921494t0.2t0.1STH
spathulenol15681572t0.30.1tSTO
caryophyllene oxide15751578ttttSTO
tricosane230023000.1tttAH
pentacosane250025000.1tt0.1AH
heptacosane270027000.1tttAH
Total identified95.796.395.094.6
Monoterpene hydrocarbons MTH2.93.83.24.7
Oxygenated monoterpenes MTO90.690.891.689.3
Sesquiterpene hydrocarbons STH-0.40.10.2
Oxygenated sesquiterpenes STO-0.30.1-
Aliphatic hydrocarbons AH0.3--0.1
Other O0.1---
Oil yield0.0340.0340.0270.024
Table 3

Composition of essentials oils of Hemerocallis cultivars aerial parts: 1H. ‘Rebel Cause’; 3H. ‘Catherine Woodbuery’; 4H. fulva; 5H. ‘Chicago Apache’; 6H. ‘Danuta’; 10H. ‘Aten’. RIexp, experimental retention index; RIlit, literature retention index; t, trace – percentage value less than 0.05%; n.i., not identified; *tentatively identified according to MS.

No.ConstituentRIexpRIlit1345610Class of compound
Content [%]
2-methybutanal6346433.6---3.02.0AO
2-methybutanal6446402.7---3.52.0AO
2-methylenebutanal*651-7.2---39.07.3AO
trans-2-methylbut-2-enal7247244.9---0.71.1AO
2-methylbutanol7267264.5---1.11.4AO
hexanal775770-----0.3AO
furfural7907940.5---t0.4O
furfuryl alcohol8468465.6---0.73.0O
6-methylhept-5-en-2-one966965-0.3---0.5AO
2-pentylfuran979981-0.3-0.1-tO
phenylacetaldehyde101010120.6-----O
p-cymene10121015-0.2--t0.5MTH
1,8-cineole10221024-4.9-1.00.313.6MTO
limonene10231025-0.3---0.2MTH
linalool108310860.94.22.55.82.50.6MTO
terpinen-4-ol11621164-0.2t-0.50.1MTO
α-terpineol117411760.20.50.70.6t0.7MTO
n.i. 79, 109, 91,1351336-55.931.439.821.634.249.9
(E)- β-damascenone13611363t1.90.9t0.1tO
methyleugenol13711369-2.6---0.3O
dihydrodehydro-β-ionone*1397-0.11.10.90.40.7tO
geranylacetone142914300.31.71.10.90.50.5O
β-ionone14651468t0.80.40.4ttO
elemicin151915220.113.0-0.5-0.3O
hexadec-1-ene158715880.31.00.51.50.2-AH
octadec-1-ene178717880.30.80.61.30.3-AH
hexahydrofarnesylacetone182618270.95.63.07.51.21.0O
farnesylacetone189018900.31.21.21.20.50.3O
isophytol193519360.22.00.50.50.30.3DT
palmitic acid194319420.6-0.3--0.3AO
eicos-1-ene198719880.1t0.20.3ttAH
eicosane20002000t0.50.10.90.3tAH
phytol210421050.52.25.00.70.30.4DT
tricosane230023000.52.97.76.90.91.0AH
tetracosane240024000.20.91.81.80.20.2AH
pentacosane250025001.78.316.321.51.73.0AH
hexacosane26002600t0.50.81.10.10.2AH
heptacosane270027000.63.45.510.20.81.0AH
nonacosane29002900t1.11.92.80.20.3AH
Total identified93.393.891.789.593.892.7
Monoterpene hydrocarbons-0.5---0.7
MTH
Oxygenated monoterpenes MTO1.19.83.27.43.315.0
Diterpenes DT0.74.25.51.20.60.7
Aliphatic hydrocarbons AH3.719.435.448.34.75.7
Oxygenated aliphatic com- pounds AO23.50.30.3-47.314.9
Other O8.428.27.511.03.75.8
Oil yield0.0330.0320.0290.0280.0330.028

2.2 Chemicals and reagents

2,6-di-tert-butyl-4-methylphenol (BHT), 2,2-diphenyl-1-picrylhydrazyl radical (DPPH•), β-carotene, linoleic acid was purchased from Sigma-Aldrich (St. Louis, MO, USA). All chemical reagents used in the experiment were of analytical grade and were provided by POCH (Gliwice, Poland).

2.3 GC-MS analysis

The composition of essential oils of Hemerocallis cultivars was analyzed using GC-MS on a Trace GC Ultra apparatus (Thermo Electron Corporation, Milan, Italy) with FID and the MS DSQ II detector after dilution in diethyl ether (10 μL in 1 mL). More details of chromatographic conditions and quantitation methods can be found in the study of Szewczyk and co-authors [28]. The percentage data shown are mean values of three injections.

Figure 1
Figure 1

Pictures of some Hemerocallis cultivars under study: A. H. ‘Bożena’, B. H. ‘Catherine Woodbuery’, C. H. ‘Danuta’, D. H. fulva, E. H. ‘Rebel Cause’, F. H. ‘Jaskółka’.

Citation: Open Chemistry 17, 1; 10.1515/chem-2019-0160

2.4 Antioxidant activity

Both assays were performed using 96-well microplates (Nunclon, Nunc, Roskilde, Denmark) and were measured in an Elisa Reader Infinite Pro 200F (Tecan Group Ltd., Männedorf, Switzerland).

2,2-diphenyl-1-picryl-hydrazyl (DPPH•) free radical scavenging activity of the essential oils and BHT was tested using a previously described method [29]. 180 μL of methanolic DPPH• solution (0.07 mg/mL) was mixed with 20 μL of various concentrations of EOs. After shaking and incubation at 28°C for 30 min in the dark, absorbance was measured at 517 nm. To determine EC50 values a dose response curves were plotted.

β-carotene bleaching method was carried out according to previously described method [30] and modified by Deba and co-authors [31]. The absorbance was measured at 470 nm.

2.5 Antibacterial assay

Zones of bacterial growth inhibition caused by tested samples were evaluated for the reference microorganisms from the American Type Culture Collection (ATCC) including Gram-positive bacteria (Staphylococcus aureus ATCC 25923, Staphylococcus epidermidis ATCC 12228) and Gram-negative bacteria (Escherichia coli ATCC 25992, Pseudomonas aeruginosa ATCC 27853). Clinical strains (Escherichia coli and Pseudomonas aeruginosa isolated from infected urine and wounds, respectively) were obtained from University Hospital No 4, 8 Jaczewskiego Street in Lublin, and stored in the micro banks at the Department of Biochemistry and Biotechnology, Medical University of Lublin, Poland. The strains were maintained at -70°C until the study was performed. Before the experiments, the bacterial strains were passaged onto fresh Mueller-Hinton agar (M-H) (Oxoid, UK) at 37°C for 48 h. Each inoculum was prepared with fresh microbial culture in sterile 0.9% NaCl to match the turbidity of 0.5 McFarland.

The antibacterial activity of samples against bacteria was evaluated by measuring the zones of inhibition in the standard disk diffusion method (Kirby-Bauer Disk Diffusion Susceptibility Test Protocol). Antibacterial disc diffusion assays were carried out on Petri plates with solid medium (M-H agar). Suitable strain culture was separately spread over the agar surface using cotton swab. Next, 10 μL of the undiluted essential oils were brought using sterile disc (disc dispenser BioMaxima, Poland) on Petri plates with agar medium. After 18 h of incubation at 37°C zones of microbial growth produced around the tested samples were measured and recorded as the diameters of inhibition [mm]. All experiments were performed in fivefold.

2.6 Statistical analysis

All the results were expressed as means ± standard deviation (SD) of three independent experiments. One-way ANOVA with Tukey’s post hoc test was used for the statistical analysis of significance of differences between means. P values below 0.05 were accepted as statistically significant. Calculations were done in Statistica 10.0 (StatSoft Poland, Cracow, Poland).

Ethical approval: The conducted research is not related to either human or animal use.

3 Results and discussion

From ancient time, Hemerocallis species have been cultivated in their native regions of Asia where these plants are still an important source of remedies and food. In Chinese and Japanese medicine daylilies have been used to treat ailments such as insomnia, fever, diuretic, inflammation, depression, and anemia [8,23,32]. In Europe, Hemerocallis spp. appeared in the late sixteenth century where they were cultivated especially for ornamental purpose [8].

Although phytochemical studies conducted on various organs of Hemerocallis have revealed the presence of many kinds of active compounds such as flavonoids [6,14,33,34], antraquinones [9,11], alkaloids [34], triterpenes [11], and caffeoylquinic acid derivatives [14,35], there is only one report about volatile oils in this genus [36].

In the present study, the essential oils (EOs) of ten Hemerocallis cultivars were obtained by hydrodistillation from air-dried aerial parts (flowers, leaves and stems). All EOs were collected as a fragrant and pale-yellow liquids. The yield of EOs (expressed in percentage; % v/w relative to dry material weight) was comparable in all samples and ranged from 0.024% (H. ‘Jaskółka’) to 0.034% (H. ‘Pink Solace’). The chemical composition was analyzed by the GC-MS method, that resulted in identification of 23-36 volatile compounds comprising from 89.5%–96.3% of the total volume in individual oils. All identified compounds in the aerial parts of Hemerocallis cultivars oils are given in Table 2 and 3.

The investigated essential oils differed in chemical composition. According to chemical profile they can be classified into three groups. The first group is composed of four EOs, 2 (H. citrina Baroni), 7 (H. ‘Pink Solace’), 8 (H. ‘Bożena’), and 9 (H. ‘Jaskółka’) (Table 2). These oils contained mainly oxygenated monoterpenes with 1,8-cineole being the major constituent (73.7-85.5%), followed by α-terpineol, α-terpinyl acetate, and terpinen-4-ol.

EOs classified to the second group [1 (H. ‘Rebel Cause’), 6 (H. ‘Danuta’), 10 (H. ‘Aten’)] and third group [3 (H. ‘Catherine Woodbuery’), 4 (H. fulva), 5 (H. ‘Chicago Apache’)] (Table 3) had a lot of common constituents such as C13 ketones ((E)-β-damascenone, β-ionone, and geranylacetone), C18 ketones (farnesylacetone and hexahydrofarnesylacetone) as well as long chain aliphatic hydrocarbons, both saturated and unsaturated. All these constituents are present in EOs of the third group in significantly higher amounts than in the second group. To the contrary, the second group EOs were characterized by pronounced amounts of very volatile C5 aliphatic aldehydes with the same skeleton, 2- and 3-methylbutanal, 2-methylenebutanal (2-ethylacrolein), and trans-2-methylbut-2-enal (tiglic aldehyde) as well as furfural and furfuryl alcohol. EO 3 contained elemicin (13.0%) and methyleugenol (2.6%).

In all EOs the same unidentified constituent was found (RI 1336), its mass spectrum is presented in Figure 2. This compound was the main constituent of EOs from the second (34.2-55.9%) and third group (21.6-39.8%) and minor component of the first group EOs (traces to 1.8%).

Figure 2
Figure 2

GC-MS chromatogram of unidentified constituent (RI 1336).

Citation: Open Chemistry 17, 1; 10.1515/chem-2019-0160

Only one report on essential oil composition of daylily Hemerocallis flava from China was found. The essential oil obtained by simultaneous distillation-extraction (SDE) contained 3-furfuryl alcohol (47.9%) and 2-furfural (10.4%) as main out of 51 constituents [36]. Considering the fact that composition of volatile oils depends on many factors, such as botanical traits, cultivation and climatic factors, as well as plant materials storage and/or treatments applied during the processing of raw material [37], it is hard to make a reliable comparison with only one published work on the essential oils in Hemerocallis species. Further investigation of composition and bioactivity of EOs in relation to other populations of Hemerocallis cultivars are needed.

It is known, as a result of bacterial resistance, that the efficacy of antibiotic therapy decreases, which needs new and safe drug strategies [38,39]. There it was favourable to examine safe therapies based on plants materials, which can prevent bacterial resistance.

Essential oils samples were determined for activity against medically relevant microorganisms, not only reference, but also clinical strains: Gram-negative (E. coli and P. aeruginosa) and Gram- positive (S. aureus and S. epidermidis). Favourable, big zones of inhibition, on solid M-H medium around all tested EOs (1-10) were against Gram-negative strains. Gram-negative strains were most strongly inhibited by samples 8 (H. ‘Bożena’), 6 (H. ‘Danuta’) (33 mm-25 mm), and also 3 (H. ‘Catherine Woodbuery’), and 2 (H. citrina Baroni) (29 mm -18 mm). The high content of 1,8-cineole that is well-known compound with pronounced antibacterial potential [40] may be responsible for strong activity of studied EOs.

Importantly, this significant activity was directed against the Gram-negative strains of both reference and troublesome clinical pathogens derived from patients’ urine or infected wounds (Figure 3).

Figure 3
Figure 3

Zones of bacterial growth inhibition of EOs of Hemerocallis cultivars tested against Gram-negative and Gram-positive bacterial strains.

Citation: Open Chemistry 17, 1; 10.1515/chem-2019-0160

None of the tested strains, in tested concentration, showed significant activity against Gram-positive bacteria. This means that Hemerocallis oils have a narrow spectrum of action directed against Gram-negative pathogens (Figure 4).

Figure 4
Figure 4

Range of antibacterial spectrum of EOs of Hemerocallis cultivars tested against Gram-negative and Gram-positive bacterial strains.

Citation: Open Chemistry 17, 1; 10.1515/chem-2019-0160

Recently, attention is focused on the protective function of naturally occurring antioxidants [40]. The present research was also undertaken to investigate the antioxidant activities of essential oils from ten Hemerocallis cultivars using two protocols with 2,2-diphenyl-1-picryl-hydrazyl (DPPH•) radicals and β-carotene/linoleic acid. The results are summarized in Table 4. The essential oils with the high presence of oxygenated monoterpenes and monoterpene hydrocarbons [2 (H. citrina), 7 (H. ‘Pink Solace’), 8 (H. ‘Bożena’), 9 (H. ‘Jaskółka’, 10 (H. ‘Aten’)] showed higher scavenging ability and they had IC50 values from 4.49±0.28 μg/mL to 19.62±0.11 μg/mL, whereas those of the synthetic antioxidant (BHT) activity was 18.32±0.92 μg/mL. Our results are in agreement with those obtained by Ruberto and Baratta [41], who showed that some monoterpene hydrocarbons and oxygenated compounds like allylic alcohols have an appreciable antioxidant activity. The essential oils of H. fulva (4) and H. ‘Rebel Cause’ (1) were found to be less efficient in the DPPH• assay with IC50 values of 60.72±1.10 and 51.59±1.13 μg/mL, respectively.

Table 4

The antioxidant activity of essential oils of Hemerocallis cultivars measured in DPPH and β-carotene/linoleic acid tests. Values are expressed as mean ± SD (n=3). The different letters (a-g) in the same column indicate a significant difference between oils (p<0.05). IC50 (μg/mL) is the concentration of the oil at which 50% is inhibited.

Essential oilIC50 (μg/mL) of DPPHIC50 (μg/mL) of β-carotene/linoleic acid
151.59±1.13b26.54±0.27c
29.78±0.22f3.70±0.07e
338.79±0.73c34.04±0.68c
460.72±1.10a2.87±0.14e
525.86±0.64d8.58±0.21d
621.07±0.23d53.12±0.16b
719.62±0.11e70.44±0.80a
84.49±0.28g1.81±0.22e
917.66±0.43e12.68±0.39d
1019.59±0.37e67.42±0.32a
BHT18.32±0.9238.24±0.25

In the second method that measures the ability to inhibit lipid peroxidation, the essential oils of 8 (H. ‘Bożena’), 4 (H. fulva), 2 (H. citrina), 5 (H. ‘Chicago Apache’), and also 1 (H. ‘Rebel Cause’) had a great activity with IC50 values even twenty one times lower than BHT used as lipophilic antioxidant reference.

From the obtained results, it can be concluded that the essential oil of Hemerocallis ‘Bożena’ (8) and H. citrina (2) had the best antioxidant activity in both performed assays.

4 Conclusions

The present study reported the composition, antibacterial and antioxidant activity of essential oils from Hemerocallis cultivars. The examined essential oils contained mainly oxygenated monoterpenes with 1,8-cineole being the major constituent. In all EOs the same unidentified constituent (RI 1336) was found in a great quantity. The obtained EOs, especially from H. ‘Bożena’, H. ‘Danuta’, and also H. ‘Catherine Woodbuery’, and H. citrina demonstrated strong antimicrobial activity against Gram-negative bacteria. Moreover, our observations suggest that essential oils from the aerial parts of Hemerocallis ‘Bożena’ and H. citrina possess strong antioxidative activity and they might be a good potential source of preservatives used in cosmetics, food and pharmaceutical industries.

Conflicts of Interest: The authors declare no conflict of interest.

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    Fu M.R., He Z., Zhao Y., Yang J., Mao L., Antioxidat properties and involved compounds of daylily flowers in relation to maturity. Food Chem. 2009, 114, 1192-1197.

    • Crossref
    • Export Citation
  • [13]

    Griesbach, R.J.; Batdorf, L. Flower pigments within Hemerocallis fulva H. rosea and H. disticha Hortscience., 1995, 30, 353-354.

    • Crossref
    • Export Citation
  • [14]

    Lin Y., Lu C., Huang Y., Chen H., Antioxidative caffeoylquinic acids and flavonoids from Hemerocallis fulva flowers. J. Agric. Food Chem., 2011, 59, 8789-95.

    • Crossref
    • PubMed
    • Export Citation
  • [15]

    Zhang Y., Cichewicz R.H., Nair M.G., Lipid peroxidation inhibitory compounds from daylily Hemerocallis fulva leaves. Life Sci., 2004, 75, 753–763.

    • Crossref
    • PubMed
    • Export Citation
  • [16]

    Konishi T., Fujiwara Y., Konoshima T., Kiyosawa S., Nishi M., Miyahara K., Steroidal saponins from Hemerocallis fulva var. kwanso Chem. Pharm. Bull., 2001, 49, 318-320.

    • Crossref
    • PubMed
    • Export Citation
  • [17]

    Inoue T., Iwagoe K., Konishi T., Kiyosawa S., Fujiwara Y., Novel 2,5-dihydrofuryl-γ-lactam derivatives from Hemerocallis fulva L. var. kwanzo Regel. Chem. Pharm. Bull., 1990, 38, 3187–3189.

    • Crossref
    • Export Citation
  • [18]

    Inoue T., Konishi T., Kiyosawa S., Fujiwara Y., 2,5-Dihydrofuryl-γ-lactam derivatives from Hemerocallis fulva L. var. kwanso Regel. II. Chem. Pharm. Bull., 1994, 42, 154–155.

    • Crossref
    • Export Citation
  • [19]

    Chen H.Y., Bor J.Y., Huang W.H., Yen G.C., Effect of sulfite-treated daylily Hemerocallis fulva L.) flower on production of nitric oxide and DNA damage in macrophages. J. Food Drug Anal., 2007, 15, 63-70.

  • [20]

    Que F., Mao L.C., Zheng X.J.,In vitro and in vivo antioxidant activities of daylily flowers and the involvement of phenolic compounds. Asia Pac. J. Clin. Nutr., 2007, 16, 196-203.

  • [21]

    Mao L.C., Pan X., Que, F., Fang X.H., Antioxidant properties of water and ethanol extracts from hot air-dried and freeze-dried daylily flowers. Eur. Food Res. Technol., 2006, 222, 236-241.

    • Crossref
    • Export Citation
  • [22]

    Uezu E., Effects of Hemerocallis on sleep in mice. Psychiatry Clin Neurosci., 1998, 52, 136–137.

    • Crossref
    • PubMed
    • Export Citation
  • [23]

    Fan C., Hui-Zi J., Wu L., Zhang Y., Ye R., Zhang W., Zhang Y., An exploration of Traditional Chinese Medicinal plants with anti-inflammatory activities. Evid. Based Complement. Alternat. Med., 2017, 1231820, https://doi.org/10.1155/2017/1231820

    • PubMed
    • Export Citation
  • [24]

    Kao F., Chiang W., Liu H., Inhibitory effect of daylily buds at various stages of maturity on nitric oxide production and the involved phenolic compounds. LWT - Food Sci. Technol., 2015, 61, 130-137.

    • Crossref
    • Export Citation
  • [25]

    Du B., Tang X., Liu F., Zhang C., Zhao G., Ren F., Leng X., Antidepressant-like effects of the hydroalcoholic extracts of Hemerocallis citrina and its potential active components. BMC Complement. Altern. Med., 2014, doi: 10.1186/1472-6882-14-326.

    • PubMed
    • Export Citation
  • [26]

    Lin, S.; Chang, H.; Chen, P.; Hsieh, C.; Su, K.; Sheen, L. The Antidepresant – like effect of ethanol extract of daylily flowers in rats. J. Tradit. Complement. Med. 2013, 3, 53-61.

    • Crossref
    • Export Citation
  • [27]

    Cichewicz R., Zhang Y., Seeram N., Nair M., Inhibition of human tumor cell proliferation by novel anthraquinones from daylilies. Life Sci., 2004, 74, 1791-1799.

    • Crossref
    • PubMed
    • Export Citation
  • [28]

    Szewczyk K., Kalemba D., Komsta Ł., Nowak R., Comparison of the essential oil composition of selected Impatiens species and its antioxidant activities. Molecules, 2016, 21, 1162.

    • Crossref
    • Export Citation
  • [29]

    Olech M., Nowacka-Jechalke N., Masłyk M., Martyna A., Pietrzak W., Kubiński K., Załuski D., Nowak R., Polysaccharide-rich fractions from Rosa rugosa Thunb. – composition and chemopreventive potential. Molecules, 2019, 24, 1354, https://doi.org/10.3390/molecules24071354

    • Crossref
    • Export Citation
  • [30]

    Siddhuraju P., Becker K., Studies on antioxidant activities of mucuna seed Mucuna pruriens var. utilis extract and various nonprotein amino/imino acids through in vitro models. J. Sci. Food Agric., 2003, 83, 1517–1524.

    • Crossref
    • Export Citation
  • [31]

    Deba F., Xuan T.D., Yasuda M., Tawata S., Chemical composition and antioxidant, antibacterial and antifungal activities of the essential oils from Bidens pilosa Linn. var. radiata Food Control., 2008, 19, 346-352.

    • Crossref
    • Export Citation
  • [32]

    Nguyen N.T.H., Arima S., Konishi T., Ogawa Y., Tran X.D., Adaniya S., Motomura K., Influence of three soil types in Okinawa, Japan and N, P, K fertilizations on growth, yield, and oxypinnatanine concentration of Hemerocallis fulva L. var. sempervirens Trop. Agr. Dev., 2016, 60, 109–118.

  • [33]

    Zhang Y., Cichewicz R.H., Nair M.G., Lipid peroxidation inhibitory compounds from daylily Hemerocallis fulva leaves. Life Sci., 2004, 75, 753–763.

    • Crossref
    • PubMed
    • Export Citation
  • [34]

    Sun J., Liu W., Zhang M., Geng P., Shan Y., Li G., Zhao Y., Chen P., The analysis of phenolic compounds in daylily using UHPLC-HRMSn and evaluation of drying processing method by fingerprinting and metabolomic approaches. J. Food Process. Preserv., 2017, 42, e13325.

  • [35]

    Clifford M.N., Wu W., Kuhnert N., The chlorogenic acids of Hemerocallis Food Chem., 2006, 95, 574-578.

    • Crossref
    • Export Citation
  • [36]

    Lin P., Cai J., Li J., Sang W., Su Q., Constituents of the essential oil of Hemerocallis flava day lily. Flavour Fragr. J., 2003, 18, 539–541.

    • Crossref
    • Export Citation
  • [37]

    Kowalski R., Kowalska G., Jankowska M., Nawrocka A., Kałwa K., Pankiewicz U., Włodarczyk-Stasiak M., Secretory structures and essential oil composition of selected industrial species of Lamiaceae. Acta Sci. Pol. Hortorum Cultus., 2019, 18, 53-69.

    • Crossref
    • Export Citation
  • [38]

    Ventola C.L., The antibiotic resistance crisis: part 2: management strategies and new agents. P. T., 2015, 40, 344-352.

    • PubMed
    • Export Citation
  • [39]

    Wang L., Wang H., Song D., Xu M., Liebmen M., New strategies for targeting drug combinations to overcome mutation-driven drug resistance. Semin. Cancer Biol., 2017, 42, 44-51.

    • Crossref
    • PubMed
    • Export Citation
  • [40]

    Candan F., Unlu M., Tepe B., Daferera D., Polissiou M., Sökmen A., Aşkin Akpulat H., Antioxidant and antimicrobial activity of the essential oil and methanol extracts of Achillea millefolium subsp. millefolium Afan. (Asteraceae). J. Ethnopharm., 2003, 87, 215-220.

    • Crossref
    • Export Citation
  • [41]

    Ruberto G., Baratta M.T., Antioxidant activity of selected essential oil components in two lipid model systems. Food Chem., 2000, 69, 167-174.

    • Crossref
    • Export Citation

If the inline PDF is not rendering correctly, you can download the PDF file here.

  • [1]

    Rehman R., Hanif M.A., Mushtaq Z., Al-Sadi A.M., Biosynthesis of essential oils in aromatic plants: A review. Food Rev. Int., 2016, 32, 117-160.

    • Crossref
    • Export Citation
  • [2]

    The Angiosperm Phylogeny Group. Chase M.W., Christenhusz M.J.M., Fay M.F., Byng J.W., Judd W.S., Soltis D.E., Mabberley D.J., Sennikov A.N., Soltis P.S., Stevens P.F., An update of the Angiosperm Phylogeny Group classification for the orders and families of flowering plants: APG IV. J. Linn. Soc., Bot., 2016, 181, 1–20. doi: 10.1111/boj.12385.

    • Crossref
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  • [3]

    https://daylilies.org Available online: 08.11.2019.

  • [4]

    Jia H.-Y., Cai W.-T., Zhang H., Gao Y.-K., He Q., Gao S.-Y., Variation of flower opening and closing times in F1 hybrids of diurnally and nocturnally flowering daylilies. Acta Hortic., 2012, 977, 149–156.

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    Zhao J., Xue L., Bi X., Lei J., Compatibility of interspecific hybridization between Hemerocallis liloasphodelus and daylily cultivars. Sci. Hortic., 2017, 220, 267-274.

    • Crossref
    • Export Citation
  • [6]

    Cichewicz, R.H., NairM.G., Isolation and characterization of stelladerol, a new antioxidan naphthalene glycoside, and other antioxidant glycosides from edible daylily Hemerocallis flowers. J. Agric. Food Chem., 2002, 50, 87–91.

    • Crossref
    • Export Citation
  • [7]

    Mlcek J., Rop O., Fresh edible flowers of ornamental plants – A new source of nutraceutical foods. Trends Food Sci. Technol., 2011, 22, 561-569.

    • Crossref
    • Export Citation
  • [8]

    Tai C.Y., Chen B.H., Analysis and stability of carotenoids in the flowers of Daylily Hemorocallis disticha as affected by various treatments. J. Agric. Food Chem., 2000, 48, 5962-5968.

    • Crossref
    • PubMed
    • Export Citation
  • [9]

    Cichewicz R.H., Lim K.C., McKerrow J.H., Nair M.G., Kwanzoquinones A-G and other constituents of Hemerocallis fulva ‘Kwanzo’ roots and their activity against the human pathogenic trematode Schistosoma mansoni Tetrahedron., 2002, 58, 8597-8606.

    • Crossref
    • Export Citation
  • [10]

    Taguchi K., Yamasaki K., Maesaki H., Tokuno M., Okazaki S., Moriuchi H., Takeshita K., Otagiri M., Seo H., An evaluation of novel biological activity in a crude extract from Hemerocallis fulva L. var. sempervirens M. Hotta. Nat. Prod. Res., 2014, 28, 2211-2213.

    • Crossref
    • Export Citation
  • [11]

    Wang Y., Xu T., Fan B., Zhang L., Lu C., Wang D., Liu X., Wang F., Advances in researches on chemical composition and functions of Hemerocallis plants. Med. Plant., 2018, 9, 16-21.

  • [12]

    Fu M.R., He Z., Zhao Y., Yang J., Mao L., Antioxidat properties and involved compounds of daylily flowers in relation to maturity. Food Chem. 2009, 114, 1192-1197.

    • Crossref
    • Export Citation
  • [13]

    Griesbach, R.J.; Batdorf, L. Flower pigments within Hemerocallis fulva H. rosea and H. disticha Hortscience., 1995, 30, 353-354.

    • Crossref
    • Export Citation
  • [14]

    Lin Y., Lu C., Huang Y., Chen H., Antioxidative caffeoylquinic acids and flavonoids from Hemerocallis fulva flowers. J. Agric. Food Chem., 2011, 59, 8789-95.

    • Crossref
    • PubMed
    • Export Citation
  • [15]

    Zhang Y., Cichewicz R.H., Nair M.G., Lipid peroxidation inhibitory compounds from daylily Hemerocallis fulva leaves. Life Sci., 2004, 75, 753–763.

    • Crossref
    • PubMed
    • Export Citation
  • [16]

    Konishi T., Fujiwara Y., Konoshima T., Kiyosawa S., Nishi M., Miyahara K., Steroidal saponins from Hemerocallis fulva var. kwanso Chem. Pharm. Bull., 2001, 49, 318-320.

    • Crossref
    • PubMed
    • Export Citation
  • [17]

    Inoue T., Iwagoe K., Konishi T., Kiyosawa S., Fujiwara Y., Novel 2,5-dihydrofuryl-γ-lactam derivatives from Hemerocallis fulva L. var. kwanzo Regel. Chem. Pharm. Bull., 1990, 38, 3187–3189.

    • Crossref
    • Export Citation
  • [18]

    Inoue T., Konishi T., Kiyosawa S., Fujiwara Y., 2,5-Dihydrofuryl-γ-lactam derivatives from Hemerocallis fulva L. var. kwanso Regel. II. Chem. Pharm. Bull., 1994, 42, 154–155.

    • Crossref
    • Export Citation
  • [19]

    Chen H.Y., Bor J.Y., Huang W.H., Yen G.C., Effect of sulfite-treated daylily Hemerocallis fulva L.) flower on production of nitric oxide and DNA damage in macrophages. J. Food Drug Anal., 2007, 15, 63-70.

  • [20]

    Que F., Mao L.C., Zheng X.J.,In vitro and in vivo antioxidant activities of daylily flowers and the involvement of phenolic compounds. Asia Pac. J. Clin. Nutr., 2007, 16, 196-203.

  • [21]

    Mao L.C., Pan X., Que, F., Fang X.H., Antioxidant properties of water and ethanol extracts from hot air-dried and freeze-dried daylily flowers. Eur. Food Res. Technol., 2006, 222, 236-241.

    • Crossref
    • Export Citation
  • [22]

    Uezu E., Effects of Hemerocallis on sleep in mice. Psychiatry Clin Neurosci., 1998, 52, 136–137.

    • Crossref
    • PubMed
    • Export Citation
  • [23]

    Fan C., Hui-Zi J., Wu L., Zhang Y., Ye R., Zhang W., Zhang Y., An exploration of Traditional Chinese Medicinal plants with anti-inflammatory activities. Evid. Based Complement. Alternat. Med., 2017, 1231820, https://doi.org/10.1155/2017/1231820

    • PubMed
    • Export Citation
  • [24]

    Kao F., Chiang W., Liu H., Inhibitory effect of daylily buds at various stages of maturity on nitric oxide production and the involved phenolic compounds. LWT - Food Sci. Technol., 2015, 61, 130-137.

    • Crossref
    • Export Citation
  • [25]

    Du B., Tang X., Liu F., Zhang C., Zhao G., Ren F., Leng X., Antidepressant-like effects of the hydroalcoholic extracts of Hemerocallis citrina and its potential active components. BMC Complement. Altern. Med., 2014, doi: 10.1186/1472-6882-14-326.

    • PubMed
    • Export Citation
  • [26]

    Lin, S.; Chang, H.; Chen, P.; Hsieh, C.; Su, K.; Sheen, L. The Antidepresant – like effect of ethanol extract of daylily flowers in rats. J. Tradit. Complement. Med. 2013, 3, 53-61.

    • Crossref
    • Export Citation
  • [27]

    Cichewicz R., Zhang Y., Seeram N., Nair M., Inhibition of human tumor cell proliferation by novel anthraquinones from daylilies. Life Sci., 2004, 74, 1791-1799.

    • Crossref
    • PubMed
    • Export Citation
  • [28]

    Szewczyk K., Kalemba D., Komsta Ł., Nowak R., Comparison of the essential oil composition of selected Impatiens species and its antioxidant activities. Molecules, 2016, 21, 1162.

    • Crossref
    • Export Citation
  • [29]

    Olech M., Nowacka-Jechalke N., Masłyk M., Martyna A., Pietrzak W., Kubiński K., Załuski D., Nowak R., Polysaccharide-rich fractions from Rosa rugosa Thunb. – composition and chemopreventive potential. Molecules, 2019, 24, 1354, https://doi.org/10.3390/molecules24071354

    • Crossref
    • Export Citation
  • [30]

    Siddhuraju P., Becker K., Studies on antioxidant activities of mucuna seed Mucuna pruriens var. utilis extract and various nonprotein amino/imino acids through in vitro models. J. Sci. Food Agric., 2003, 83, 1517–1524.

    • Crossref
    • Export Citation
  • [31]

    Deba F., Xuan T.D., Yasuda M., Tawata S., Chemical composition and antioxidant, antibacterial and antifungal activities of the essential oils from Bidens pilosa Linn. var. radiata Food Control., 2008, 19, 346-352.

    • Crossref
    • Export Citation
  • [32]

    Nguyen N.T.H., Arima S., Konishi T., Ogawa Y., Tran X.D., Adaniya S., Motomura K., Influence of three soil types in Okinawa, Japan and N, P, K fertilizations on growth, yield, and oxypinnatanine concentration of Hemerocallis fulva L. var. sempervirens Trop. Agr. Dev., 2016, 60, 109–118.

  • [33]

    Zhang Y., Cichewicz R.H., Nair M.G., Lipid peroxidation inhibitory compounds from daylily Hemerocallis fulva leaves. Life Sci., 2004, 75, 753–763.

    • Crossref
    • PubMed
    • Export Citation
  • [34]

    Sun J., Liu W., Zhang M., Geng P., Shan Y., Li G., Zhao Y., Chen P., The analysis of phenolic compounds in daylily using UHPLC-HRMSn and evaluation of drying processing method by fingerprinting and metabolomic approaches. J. Food Process. Preserv., 2017, 42, e13325.

  • [35]

    Clifford M.N., Wu W., Kuhnert N., The chlorogenic acids of Hemerocallis Food Chem., 2006, 95, 574-578.

    • Crossref
    • Export Citation
  • [36]

    Lin P., Cai J., Li J., Sang W., Su Q., Constituents of the essential oil of Hemerocallis flava day lily. Flavour Fragr. J., 2003, 18, 539–541.

    • Crossref
    • Export Citation
  • [37]

    Kowalski R., Kowalska G., Jankowska M., Nawrocka A., Kałwa K., Pankiewicz U., Włodarczyk-Stasiak M., Secretory structures and essential oil composition of selected industrial species of Lamiaceae. Acta Sci. Pol. Hortorum Cultus., 2019, 18, 53-69.

    • Crossref
    • Export Citation
  • [38]

    Ventola C.L., The antibiotic resistance crisis: part 2: management strategies and new agents. P. T., 2015, 40, 344-352.

    • PubMed
    • Export Citation
  • [39]

    Wang L., Wang H., Song D., Xu M., Liebmen M., New strategies for targeting drug combinations to overcome mutation-driven drug resistance. Semin. Cancer Biol., 2017, 42, 44-51.

    • Crossref
    • PubMed
    • Export Citation
  • [40]

    Candan F., Unlu M., Tepe B., Daferera D., Polissiou M., Sökmen A., Aşkin Akpulat H., Antioxidant and antimicrobial activity of the essential oil and methanol extracts of Achillea millefolium subsp. millefolium Afan. (Asteraceae). J. Ethnopharm., 2003, 87, 215-220.

    • Crossref
    • Export Citation
  • [41]

    Ruberto G., Baratta M.T., Antioxidant activity of selected essential oil components in two lipid model systems. Food Chem., 2000, 69, 167-174.

    • Crossref
    • Export Citation
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Open Chemistry is a peer-reviewed, open access journal that publishes original research, reviews and short communications in the fields of chemistry in an ongoing way. Our central goal is to provide a hub for researchers working across all subjects to present their discoveries, and to be a forum for the discussion of the important issues in the field.

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  • View in gallery
  • View in gallery

    Pictures of some Hemerocallis cultivars under study: A. H. ‘Bożena’, B. H. ‘Catherine Woodbuery’, C. H. ‘Danuta’, D. H. fulva, E. H. ‘Rebel Cause’, F. H. ‘Jaskółka’.

  • View in gallery

    GC-MS chromatogram of unidentified constituent (RI 1336).

  • View in gallery

    Zones of bacterial growth inhibition of EOs of Hemerocallis cultivars tested against Gram-negative and Gram-positive bacterial strains.

  • View in gallery

    Range of antibacterial spectrum of EOs of Hemerocallis cultivars tested against Gram-negative and Gram-positive bacterial strains.