Chemical Composition and Antimicrobial and Antioxidant Activities of Essential Oil of Sunflower (Helianthus annuus L.) Receptacle
Abstract
:1. Introduction
2. Results and Discussion
2.1. Yield and Chemical Composition of SEO
2.2. Antimicrobial Activities of SEO against Bacteria and Fungi
2.2.1. Antibacterial Activities
2.2.2. Antifungal Activities
2.3. Antioxidant Activity
2.3.1. ABTS Radical Scavenging Activity
2.3.2. DPPH Radical Scavenging Activity
2.3.3. Iron Ion Reduction Ability Analysis
3. Materials and Methods
3.1. Chemical Reagents and Solvents
3.2. Plant Materials and Extraction of Essential Oil
3.3. Analysis of Chemical Compositions of Essential Oil
3.4. Antimicrobial Effects
3.4.1. Microbial Cultures of Three Bacterial Strains
3.4.2. Detection of Antimicrobial Activities
3.5. Determination of Antioxidant Activities
3.5.1. ABTS Radical Scavenging
3.5.2. DPPH Radical Scavenging
3.5.3. Iron Ion Reducing Assay
3.6. Statistical Analysis
4. Conclusions
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
Abbreviations
SEO | Essential oil from the receptacle of sunflower |
GC-MS | Gas chromatography–mass spectrometry |
DPPH | 2,2-Diphenyl-1-picrylhydrazyl |
ABTS | 2,2-Azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) |
MIC | Minimum inhibitory concentration |
MBC | Minimum bactericidal concentration |
P. aeruginosa | Pseudomonas aeruginosa |
S. aureus | Staphylococcus aureus |
S. cerevisiae | Saccharomyces cerevisiae |
E. coli | Escherichiacoli |
RT | Peak time |
RI | Retention indices |
NIST | National institute of standards and technology |
LB | Lysogeny broth |
YPDA | Yeast extract peptone dextrose medium and adenine |
DMSO | Dimethyl sulfoxide |
ANOVA | One-way analysis of variance |
Appendix A
Peak Area | Content (%) | |
---|---|---|
α-Pinene | 11,517,282 | 26.00% |
Verbenone | 3,393,766 | 7.40% |
Terpinolene | 562,092 | 1.69% |
α-Terpineol | 168,387 | 1.27% |
E. coli | P. aeruginosa | S. aureus | ||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
MIC | Mean a | SD | MBC | Mean | SD | MIC | Mean | SD | MBC | Mean | SD | MIC | Mean | SD | MBC | Mean | SD | |
Essential oil | 6.4 | 0.15 | 0.126 | 12.8 | 0.06 | 0.016 | 0.2 | 0.03 | 0.005 | 0.2 | 0.03 | 0.005 | 0.2 | 0.161 | 0.007 | 0.4 | 0.045 | 0.01 |
α-Pinene | 12.8 | 0.13 | 0.028 | >12.8 | - | - | 6.4 | 0.287 | 0.085 | 12.8 | 0.074 | 0.062 | 6.4 | 0.041 | 0.007 | 6.4 | 0.041 | 0.007 |
α-Terpineol | 6.4 | 0.027 | 0.002 | 6.4 | 0.027 | 0.002 | 3.2 | 0.075 | 0.04 | 6.4 | 0.032 | 0.012 | 6.4 | 0.034 | 0.002 | 6.4 | 0.034 | 0.002 |
Terpinolene | >12.8 | - | - | >12.8 | - | - | >12.8 | - | - | >12.8 | - | - | 6.4 | 0.065 | 0.009 | 6.4 | 0.065 | 0.009 |
Verbenone | 12.8 | 0.119 | 0.032 | >12.8 | - | - | >12.81.6 | - | - | >12.8 | - | - | 3.2 | 0.08 | 0.013 | 3.2 | 0.08 | 0.013 |
Mixture b | 1.6 | 0.069 | 0.009 | 3.2 | 0.069 | 0.009 | - | 0.034 | 0.001 | 1.6 | 0.034 | 0.001 | 1.6 | 0.039 | 0.008 | 1.6 | 0.039 | 0.008 |
Tetracycline c | - | - | - | <0.05 | 0.032 | 0.002 | - | - | <0.05 | 0.032 | 0.002 | - | - | - | <0.05 | 0.037 | 0.007 |
S. cerevisiae (yeast) | Candida albicans | |||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
MIC (mg/mL) | Mean | SD | MBC (mg/mL) | Mean | SD | MIC (mg/mL) | Mean | SD | MBC (mg/mL) | Mean | SD | |
Essential oil | 3.2 | 0.144 | 0.016 | 3.2 | 0.144 | 0.016 | 6.4 | 0.085 | 0.009 | 12.8 | 0.043 | 0.112 |
α-Pinene | 0.8 | 0.082 | 0.076 | 1.6 | 0.043 | 0.003 | 3.2 | 0.053 | 0.01 | 3.2 | 0.053 | 0.01 |
α-Terpineol | 3.2 | 0.043 | 0.009 | 3.2 | 0.043 | 0.009 | 6.4 | 0.037 | 0.001 | 6.4 | 0.037 | 0.001 |
Terpinolene | 1.6 | 0.037 | 0.005 | 1.6 | 0.037 | 0.005 | 1.6 | 0.036 | 0.005 | 1.6 | 0.036 | 0.005 |
Verbenone | 12.8 | 0.038 | 0.001 | 12.8 | 0.038 | 0.001 | 6.4 | 0.227 | 0.45 | 12.8 | 0.043 | 0.002 |
Miconazole nitrate a | - | - | - | <0.05 | 0.041 | −0.003 | - | - | - | <0.05 | 0.062 | 0.006 |
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NO. | Compound | Molecular Formula | RT a | RI b | MF c | RMF d | Content (%) | Identification e |
---|---|---|---|---|---|---|---|---|
1 | α-Pinene | C10H16 | 3.70 | 930 | 953 | 954 | 26.00 | 1,2,3 |
2 | Camphene | C10H16 | 3.87 | 943 | 906 | 911 | 0.21 | 1,2 |
3 | 2,4-Thujadiene | C10H14 | 3.93 | 957 | 844 | 858 | 0.76 | 1,2 |
4 | β-Terpinene | C10H16 | 4.26 | 964 | 876 | 918 | 0.15 | 1,2 |
5 | l-β-Pinene | C10H16 | 4.31 | 969 | 926 | 935 | 0.38 | 1,2 |
6 | Epoxycyclooctane | C8H14O | 4.39 | 971 | 896 | 912 | 0.22 | 1,2 |
7 | 2,3-Dehydro-1,8-cineole | C10H16O | 4.50 | 1041 | 791 | 835 | 0.33 | 1,2 |
8 | 1,3,8-p-Menthatriene | C10H14 | 4.56 | 1042 | 872 | 913 | 0.25 | 1,2 |
9 | E,E-2,6-Dimethyl-1,3,5,7-octatetraene | C10H14 | 4.79 | 1049 | 902 | 915 | 0.27 | 1,2 |
10 | 4-Isopropenyltoluene | C10H12 | 4.87 | 1073 | 849 | 895 | 0.07 | 1,2 |
11 | o-Cymene | C10H14 | 5.10 | 1079 | 929 | 939 | 0.62 | 1,2 |
12 | Isosylvestrene | C10H16 | 5.27 | 1083 | 879 | 923 | 0.11 | 1,2 |
13 | γ-Terpinen | C10H16 | 5.83 | 1101 | 908 | 918 | 0.18 | 1,2 |
14 | trans-p-Mentha-2,8-dienol | C10H16O | 5.99 | 1111 | 746 | 747 | 1.30 | 1,2 |
15 | Berbenol | C10H16O | 6.16 | 1117 | 824 | 830 | 0.13 | 1,2 |
16 | Campholenal | C10H16O | 6.24 | 1119 | 854 | 875 | 0.10 | 1,2 |
17 | 4-Isopropenyltoluene | C10H12 | 6.31 | 1123 | 919 | 940 | 0.33 | 1,2 |
18 | Terpinolene | C10H16 | 6.40 | 1124 | 901 | 925 | 1.69 | 1,2,3 |
19 | Benzyl ethyl carbinol | C10H14O | 7.05 | 1131 | 761 | 799 | 0.35 | 1,2 |
20 | l-Pinocarveol | C10H16O | 7.24 | 1143 | 920 | 928 | 0.17 | 1,2 |
21 | cis-Verbenol | C10H16O | 7.32 | 1146 | 862 | 899 | 0.82 | 1,2 |
22 | d-Verbenol | C10H16O | 7.41 | 1149 | 917 | 919 | 4.11 | 1,2 |
23 | Pinocarvone | C10H14O | 7.54 | 1157 | 873 | 891 | 1.14 | 1,2 |
24 | l-Terpinen-4-ol | C10H18O | 8.00 | 1158 | 909 | 920 | 0.56 | 1,2 |
25 | p-Cymen-8-ol | C10H14O | 8.07 | 1160 | 906 | 920 | 0.61 | 1,2 |
26 | Myrtenal | C10H14O | 8.13 | 1169 | 927 | 933 | 0.07 | 1,2 |
27 | α-Terpineol | C10H18O | 8.19 | 1172 | 821 | 839 | 1.27 | 1,2,3 |
28 | Verbenone | C10H14O | 8.34 | 1198 | 908 | 917 | 7.40 | 1,2,3 |
29 | cis-Carveol | C10H16O | 8.76 | 1207 | 942 | 944 | 2.20 | 1,2 |
30 | l-Carveol | C10H16O | 8.95 | 1213 | 704 | 719 | 0.25 | 1,2 |
31 | Carvol | C10H14O | 9.02 | 1217 | 857 | 894 | 0.25 | 1,2 |
32 | Hotrienol | C10H16O | 9.10 | 1218 | 657 | 747 | 0.17 | 1,2 |
33 | 3,5-Diethylphenol | C10H14O | 9.17 | 1219 | 762 | 799 | 0.16 | 1,2 |
34 | trans-2-Caren-4-ol | C10H16O | 9.38 | 1224 | 734 | 750 | 0.19 | 1,2 |
35 | Bornyl acetate | C12H20O2 | 9.95 | 1259 | 887 | 892 | 0.72 | 1,2 |
36 | (−)-trans-Pinocarvyl acetate | C12H18O2 | 10.16 | 1264 | 742 | 754 | 0.15 | 1,2 |
37 | 4-Vinylguaiacol | C9H10O2 | 10.25 | 1271 | 818 | 845 | 0.25 | 1,2 |
38 | 1,4-p-Menthadien-7-ol | C10H16O | 10.65 | 1291 | 739 | 774 | 0.31 | 1,2 |
39 | Aromadendrene, dehydro- | C15H22 | 12.42 | 1407 | 747 | 778 | 0.25 | 1,2 |
40 | Calarene | C15H24 | 12.55 | 1412 | 903 | 930 | 5.27 | 1,2 |
41 | 4,5,9,10-dehydro-Isolongifolene | C15H20 | 12.91 | 1424 | 752 | 764 | 0.25 | 1,2 |
42 | 2-Tridecanone | C13H26O | 13.39 | 1439 | 885 | 896 | 0.33 | 1,2 |
43 | Bisabolene | C15H24 | 13.69 | 1450 | 896 | 912 | 0.52 | 1,2 |
44 | Cadina-3,9-diene | C15H24 | 13.86 | 1456 | 835 | 851 | 0.30 | 1,2 |
45 | Juniper camphor | C15H26O | 14.20 | 1467 | 790 | 801 | 0.30 | 1,2 |
46 | (−)-Spathulenol | C15H24O | 14.52 | 1478 | 842 | 849 | 0.51 | 1,2 |
47 | Caryophyllene oxide | C15H24O | 14.59 | 1480 | 661 | 689 | 0.18 | 1,2 |
48 | Isoaromadendrene epoxide | C15H24O | 14.90 | 1490 | 775 | 791 | 0.70 | 1,2 |
49 | cis-Lanceol | C15H24O | 15.00 | 1494 | 749 | 805 | 0.43 | 1,2 |
50 | 3,3,5,6,7-Pentamethyl-1-indanone | C14H18O | 15.35 | 1505 | 790 | 791 | 2.96 | 1,2 |
51 | Trans-Longipinocarveol | C15H24O | 16.09 | 1530 | 723 | 758 | 0.52 | 1,2 |
52 | Dehydro-cyclolongifolene oxide | C15H22O | 16.87 | 1556 | 740 | 752 | 4.81 | 1,2 |
53 | Tetradecanoic acid | C14H28O2 | 17.20 | 1567 | 701 | 778 | 0.15 | 1,2 |
54 | 9-Hexadecenoic acid | C16H30O2 | 19.40 | 1701 | 661 | 669 | 0.22 | 1,2 |
55 | Androst-2,16-diene | C19H28 | 19.62 | 1709 | 738 | 743 | 0.19 | 1,2 |
56 | Phellopterin | C17H16O5 | 19.77 | 1773 | 766 | 786 | 2.17 | 1,2 |
57 | Hexadecanoic acid | C16H32O2 | 19.84 | 1775 | 878 | 895 | 2.26 | 1,2 |
58 | Manoyl oxide | C20H34O | 20.12 | 1945 | 868 | 889 | 0.23 | 1,2 |
59 | Androstane-3,11-diol | C19H32O2 | 20.81 | 1985 | 711 | 736 | 0.32 | 1,2 |
60 | Methyl isopimarate | C21H32O2 | 21.35 | 1998 | 742 | 802 | 0.37 | 1,2 |
61 | Linoleic acid | C18H32O2 | 21.57 | 2008 | 793 | 847 | 1.00 | 1,2 |
62 | trans-Oleic acid | C18H34O2 | 21.65 | 2012 | 629 | 691 | 0.27 | 1,2 |
63 | Kaur-16-ene | C20H32 | 22.23 | 2037 | 852 | 872 | 3.51 | 1,2 |
64 | 16-Kauran-16-ol | C20H34O | 22.30 | 2040 | 870 | 888 | 1.65 | 1,2 |
75 | Kauran-16-ol | C20H34O | 22.43 | 2045 | 847 | 869 | 0.99 | 1,2 |
66 | Cryptopinon | C20H30O | 22.59 | 2052 | 769 | 798 | 0.29 | 1,2 |
67 | Pimaric acid | C20H30O2 | 23.71 | 2101 | 739 | 741 | 3.09 | 1,2 |
68 | Abietic acid | C20H30O2 | 24.26 | 2125 | 785 | 786 | 3.78 | 1,2 |
Pentadecane f | ||||||||
Total compounds | 92.07 | |||||||
Oxygenated monoterpenes | 54.65 | |||||||
Sesquiterpenoids | 22.73 | |||||||
Others | 14.69 |
Compound | Receptacle | Capitula a [9] | Pollen b [10] | |||
---|---|---|---|---|---|---|
RI c | Content (%) | RI | Content (%) | RI | Content (%) | |
α-Pinene | 930 | 26.00 | 940 | 74.50 | 941 | 20.57 |
Verbenone | 1198 | 7.40 | 1206 | 0.2 | 1205 | 1.52 |
Calarene | 1412 | 5.27 | - | - | - | - |
Dehydro-cyclolongifolene oxide | 1556 | 4.81 | - | - | - | - |
d-Verbenol | 1149 | 4.11 | - | - | - | - |
Abietic acid | 2125 | 3.78 | - | - | - | - |
Kaur-16-ene | 2037 | 3.51 | - | - | - | - |
Pimaric acid | 2101 | 3.09 | - | - | - | - |
3,3,5,6,7-Pentamethyl-1-Indanone | 1505 | 2.96 | - | - | - | - |
Hexadecanoic acid | 1775 | 2.26 | - | - | - | - |
cis-Carveol | 1207 | 2.20 | - | - | - | - |
Phellopterin | 1773 | 2.17 | - | - | - | - |
Terpinolene | 1124 | 1.69 | 1089 | 0.2 | - | - |
16-Kaur-16-ol | 2040 | 1.65 | - | - | - | - |
α-Terpineol | 1172 | 1.27 | 1020 | 0.4 | - | - |
trans-p-Mentha-2,8-dienol | 1111 | 1.30 | 1126 | 0.05 | - | - |
Pinocarvone | 1157 | 1.14 | 1164 | 0.1 | - | - |
Linoleic acid | 2008 | 1.00 | - | - | - | - |
Kauran-16-ol | 2045 | 0.99 | - | - | - | - |
cis-Verbenol | 1146 | 0.82 | 1143 | 0.7 | - | - |
Sample | E. coli | P. aeruginosa | S. aureus | |||
---|---|---|---|---|---|---|
MIC (mg/mL) | MBC (mg/mL) | MIC (mg/mL) | MBC (mg/mL) | MIC (mg/mL) | MBC (mg/mL) | |
SEO | 6.4 | 12.8 | 0.2 | 0.2 | 0.2 | 0.4 |
α-Pinene | 12.8 | >12.8 | 6.4 | 12.8 | 6.4 | 6.4 |
α-Terpineol | 6.4 | 6.4 | 3.2 | 6.4 | 6.4 | 6.4 |
Terpinolene | >12.8 | >12.8 | >12.8 | >12.8 | 6.4 | 6.4 |
Verbenone | 12.8 | >12.8 | >12.8 | >12.8 | 3.2 | 3.2 |
Mixture a | 1.6 | 3.2 | 1.6 | 1.6 | 1.6 | 1.6 |
Tetracycline b | ND | <0.05 | ND | <0.05 | ND | <0.05 |
Sample | S. cerevisiae | Candida albicans | ||
---|---|---|---|---|
MIC (mg/mL) | MBC (mg/mL) | MIC (mg/mL) | MBC (mg/mL) | |
SEO | 3.2 | 3.2 | 6.4 | 12.8 |
α-Pinene | 0.8 | 1.6 | 3.2 | 3.2 |
α-Terpineol | 3.2 | 3.2 | 6.4 | 6.4 |
Terpinolene | 1.6 | 1.6 | 1.6 | 1.6 |
Verbenone | 12.8 | 12.8 | 6.4 | 12.8 |
Miconazole nitrate a | ND | <0.05 | ND | <0.05 |
Sample Availability: Samples of the compounds are not available from the authors. |
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Liu, X.-S.; Gao, B.; Li, X.-L.; Li, W.-N.; Qiao, Z.-A.; Han, L. Chemical Composition and Antimicrobial and Antioxidant Activities of Essential Oil of Sunflower (Helianthus annuus L.) Receptacle. Molecules 2020, 25, 5244. https://doi.org/10.3390/molecules25225244
Liu X-S, Gao B, Li X-L, Li W-N, Qiao Z-A, Han L. Chemical Composition and Antimicrobial and Antioxidant Activities of Essential Oil of Sunflower (Helianthus annuus L.) Receptacle. Molecules. 2020; 25(22):5244. https://doi.org/10.3390/molecules25225244
Chicago/Turabian StyleLiu, Xin-Sheng, Bo Gao, Xin-Lu Li, Wan-Nan Li, Zi-An Qiao, and Lu Han. 2020. "Chemical Composition and Antimicrobial and Antioxidant Activities of Essential Oil of Sunflower (Helianthus annuus L.) Receptacle" Molecules 25, no. 22: 5244. https://doi.org/10.3390/molecules25225244