Metabolite profiles of Chinese native Citrus species and their taxonomic implications
Li Jing 1,2,3, Zhentian Lei 2, Guiwei Zhang 1, 3, Alan Cesar Pilon2, 4, David V Huhman2, RangjinXie5, Wanpeng Xi 1, 3, Zhiqin Zhou1, 3*, Lloyd W Sumner 2*
1 College of Horticulture and Landscape Architecture, Southwest University, Chongqing 400716, China
2 Plant Biology Division, the Samuel Roberts Noble Foundation, 2510 Sam Noble Parkway, Ardmore, OK 73401
3 Key Laboratory of Horticulture Science for Southern Mountainous Regions, Ministry of Education, Chongqing 400715, China
4 Nucleus of Bioassays, Biosynthesis and Ecophysiology of Natural Products -NuBBE, São Paulo State University - UNESP, Rua Prof. Francisco Degni 55, Araraquara, 14800-900, São Paulo, Brazil
5Citrus research institute, Chinese Academy of Agricultural Sciences/Southwest University, Chongqing 400712, China
*Corresponding authors: Plant biology division, The Samuel Roberts Noble Foundation, 2510 Sam Noble Parkway, Ardmore, OK 73401. Tel: 1-580-224-6710; Fax: 1-580-224-6692; Email: r College of Horticulture and Landscape Architecture, Southwest University, Chongqing 400716, China. Tel: 86-23-68250229; Fax: 86-23-68251274; Email: .
Supplemental Table 1 Phytochemical components of citrus essential oils
# / RT / Ri-RI(lib) / Score / Library / Name / Citrus essential oil(min) / (min) / Mi / Ta / Su / Dao / Go / We / Ba / Dai / Chi / Zh
1 / 15.0376 / -7.8 / 83 / Adam / α-Thujene / 0.01±0.00 / 0.01±0.00 / 0.01±0.01 / 0.88±0.01 / 1.23±0.01 / 0.45±0.04 / tr / 0.01±0.00 / 0.01±0.00 / 1.51±0.14
2 / 15.4750 / -5.1 / 98 / Adam / α-Pinene / 0.98±0.07 / 1.19±0.04 / 1.23±0.15 / 3.11±0.10 / 4.07±0.08 / 2.04±0.13 / 1.23±0.01 / 0.85±0.08 / 1.22±0.08 / 4.93±0.31
3 / 17.3848 / 4.4 / 97 / Adam / Sabinene / 1.12±0.23 / 0.74±0.07 / 0.59±0.28 / 0.21±0.04 / 2.54±0.10 / 0.19±0.03 / 0.15±0.03 / 0.11±0.02 / 0.36±0.03 / 0.17±0.06
4 / 18.0693 / 2.1 / 95 / Adam / Myrcene / 5.70±0.44 / 5.85±0.21 / 5.83±0.35 / 4.95±0.12 / 4.67±0.10 / 4.81±0.13 / 5.63±0.02 / 11.05±0.13 / 5.50±0.11 / 3.87±0.13
5 / 18.8887 / 2.3 / 79 / Noble / α-Phellandrene / 0.02±0.01 / 0.01±0.00 / 0.08±0.01 / tr / tr / tr / tr / tr / tr / tr
6 / 19.3785 / 2.3 / 79 / Noble / α-Terpinene / 0.05±0.01 / 0.03±0.00 / 0.04±0.00 / 0.19±0.03 / 0.29±0.01 / 0.10±0.01 / 0.01±0.00 / 0.01±0.00 / 0.02±0.00 / 0.41±0.02
7 / 19.9738 / 3.6 / 95 / Noble / R-(+)-Limonene / 90.21±0.98 / 90.87±0.00 / 91.06±1.05 / 68.93±0.86 / 62.72±0.32 / 78.87±0.35 / 90.31±1.02 / 85.09±0.18 / 90.03±0.12 / 57.99±0.71
8 / 20.2929 / 6.2 / 78 / Noble / Eucalyptol / tr / tr / tr / tr / 0.01±0.00 / tr / tr / 0.01±0.00 / tr / tr
9 / 21.1755 / -2.2 / 67 / Adam / para-Mentha-3,8-diene / 0.19±0.01 / 0.11±0.01 / 0.19±0.03 / 18.45±0.20 / 21.83±0.10 / 11.39±0.20 / 0.04±0.01 / 0.11±0.03 / 0.10±0.02 / 28.04±0.43
10 / 22.1857 / 0 / 95 / Noble / Terpinolene / 0.09±0.01 / 0.06±0.00 / 0.12±0.00 / 0.72±0.01 / 1.05±0.04 / 0.40±0.01 / 0.04±0.01 / 0.04±0.00 / 0.09±0.01 / 1.44±0.09
11 / 22.5936 / Unknown / 0.61±0.10 / 0.42±0.04 / 0.03±0.02 / 1.49±0.20 / 0.79±0.12 / 1.20±0.20 / 1.42±0.18 / 0.11±0.05 / 0.65±0.11 / 0.30±0.06
12 / 22.8511 / Unknown / 0.09±0.00 / 0.10±0.00 / 0.04±0.01 / 0.64±0.97 / 0.11±0.01 / 0.10±0.01 / 0.61±0.88 / 0.11±0.00 / 0.12±0.01 / 0.04±0.00
13 / 23.1121 / Unknown / — / — / tr / — / — / — / — / tr / tr / tr
14 / 23.7966 / Unknown / tr / tr / tr / 0.01±0.00 / 0.01±0.00 / tr / 0.01±0.00 / tr / 0.01±0.00 / 0.01±0.00
15 / 24.0737 / Unknown / 0.01±0.00 / tr / 0.01±0.00 / 0.01±0.00 / 0.02±0.00 / 0.01±0.00 / 0.01±0.00 / 0.01±0.00 / 0.01±0.00 / 0.02±0.00
16 / 24.3212 / Unknown / tr / 0.01±0.00 / 0.01±0.00 / 0.01±0.01 / 0.02±0.00 / 0.01±0.00 / 0.01±0.00 / tr / 0.01±0.00 / 0.02±0.02
17 / 24.5631 / 5.2 / 82 / Adam / Isopulegol / tr / tr / tr / tr / tr / tr / tr / — / — / tr
18 / 26.3636 / 3.7 / 64 / Adam / Octanol acetate / 0.36±0.04 / 0.34±0.01 / 0.24±0.06 / 0.13±0.02 / 0.30±0.03 / 0.24±0.01 / 0.03±0.01 / 0.76±0.07 / 0.47±0.01 / 0.22±0.03
19 / 27.9811 / Unknown / 0.01±0.00 / 0.01±0.00 / 0.01±0.00 / 0.01±0.00 / 0.01±0.00 / tr / 0.01±0.00 / 0.02±0.00 / 0.02±0.00 / 0.01±0.00
20 / 28.1059 / Unknown / 0.01±0.00 / 0.01±0.00 / 0.01±0.00 / 0.01±0.00 / 0.02±0.00 / 0.01±0.00 / tr / 0.03±0.00 / 0.02±0.00 / 0.01±0.00
21 / 28.3492 / Unknown / 0.21±0.10 / 0.06±0.02 / 0.08±0.06 / 0.01±0.00 / 0.01±0.00 / 0.01±0.00 / 0.01±0.01 / 0.11±0.01 / 0.14±0.00 / 0.01±0.00
22 / 29.4755 / Unknown / 0.01±0.00 / 0.01±0.00 / 0.01±0.00 / 0.01±0.00 / 0.02±0.00 / 0.01±0.00 / 0.01±0.00 / 0.03±0.00 / 0.02±0.00 / 0.01±0.00
23 / 30.3954 / Unknown / — / — / — / tr / — / tr / tr / — / tr / —
24 / 30.5727 / -0.3 / 61 / Adam / Citronellyl acetate / 0.01±0.00 / 0.01±0.00 / 0.01±0.01 / 0.03±0.02 / 0.04±0.00 / 0.03±0.01 / 0.06±0.01 / 0.07±0.01 / 0.04±0.00 / 0.05±0.00
25 / 30.7500 / Unknown / tr / — / tr / tr / tr / tr / tr / tr / tr / tr
26 / 30.8450 / Unknown / 0.01±0.00 / 0.01±0.00 / 0.01±0.00 / 0.01±0.00 / 0.30±0.00 / 0.02±0.01 / 0.15±0.03 / 0.29±0.03 / 0.28±0.01 / 0.28±0.02
27 / 31.3843 / Unknown / tr / tr / tr / 0.01±0.01 / 0.20±0.00 / tr / 0.06±0.01 / 0.79±0.14 / 0.60±0.02 / 0.01±0.00
28 / 31.5269 / Unknown / tr / tr / tr / tr / tr / tr / tr / tr / tr / tr
29 / 31.6301 / -2.7 / 63 / Adam / 7-epi-Sesquithujene / tr / — / tr / tr / tr / tr / tr / tr / tr / tr
30 / 31.9340 / Unknown / 0.02±0.00 / 0.01±0.00 / 0.01±0.00 / 0.07±0.02 / 0.60±0.00 / tr / 0.01±0.00 / tr / tr / tr
31 / 32.3138 / Unknown / tr / tr / tr / tr / 0.01±0.01 / tr / tr / 0.06±0.01 / 0.04±0.00 / 0.02±0.01
32 / 32.5449 / Unknown / 0.01±0.00 / tr / 0.01±0.01 / 0.01±0.00 / 0.01±0.00 / 0.01±0.00 / 0.01±0.00 / 0.03±0.01 / 0.01±0.00 / 0.01±0.00
33 / 32.8427 / Unknown / 0.02±0.00 / 0.01±0.00 / 0.03±0.01 / 0.01±0.00 / 0.03±0.00 / 0.01±0.00 / 0.02±0.00 / 0.09±0.01 / 0.04±0.00 / 0.01±0.00
34 / 32.9142 / -2.6 / 82 / Noble / (-)-trans-Caryophyllene / tr / tr / tr / tr / tr / tr / tr / tr / tr / tr
35 / 33.0699 / -1.5 / 79 / Adam / cis-Prenyl limonene / tr / — / tr / tr / tr / tr / — / tr / tr / tr
36 / 33.1566 / Unknown / 0.03±0.00 / 0.01±0.00 / 0.01±0.00 / tr / tr / tr / 0.02±0.01 / tr / tr / 0.01±0.00
37 / 33.1999 / Unknown / 0.02±0.00 / 0.01±0.00 / 0.01±0.00 / tr / tr / 0.01±0.00 / 0.02±0.00 / 0.02±0.01 / 0.01±0.00 / 0.01±0.00
38 / 33.4176 / Unknown / 0.04±0.04 / tr / 0.01±0.01 / tr / tr / tr / 0.02±0.01 / 0.04±0.01 / 0.07±0.00 / 0.26±0.05
39 / 33.8017 / Unknown / tr / tr / tr / 0.01±0.00 / 0.01±0.00 / tr / tr / tr / tr / tr
40 / 33.8684 / Unknown / tr / tr / tr / tr / tr / tr / tr / tr / tr / tr
41 / 34.4533 / Unknown / 0.01±0.00 / 0.01±0.00 / 0.01±0.01 / 0.02±0.01 / 0.01±0.00 / 0.03±0.01 / 0.02±.001 / 0.14±0.01 / 0.05±0.01 / 0.15±0.03
42 / 34.5122 / 3.6 / 90 / Adam / trans-Muurola-4(14),5-diene / 0.01±0.00 / 0.01±0.00 / 0.01±0.00 / 0.01±0.01 / tr / 0.03±0.00 / 0.02±0.01 / 0.01±0.00 / 0.05±0.00 / 0.15±0.03
43 / 34.5742 / Unknown / — / — / tr / — / — / — / — / — / — / —
44 / 34.7472 / 1 / 89 / Adam / α-Farnesene / 0.07±0.00 / 0.06±0.01 / 0.17±0.06 / tr / tr / tr / 0.01±0.00 / tr / 0.01±0.00 / 0.01±0.00
45 / 34.8604 / Unknown / 0.03±0.01 / 0.02±0.01 / 0.07±0.03 / tr / tr / tr / 0.01±0.00 / tr / tr / tr
46 / 34.9696 / 1.1 / 80 / Adam / β-Curcumene / tr / tr / 0.01±0.00 / tr / tr / tr / tr / tr / tr / tr
47 / 35.3234 / 1.6 / 64 / Adam / Zonarene / 0.02±0.01 / 0.01±0.00 / 0.02±0.01 / 0.02±0.01 / 0.02±0.00 / 0.01±0.00 / 0.02±0.01 / tr / 0.01±0.00 / 0.01±0.00
Metabolite derivatives were tentatively identified by matching retention time as well as mass spectra with those in NF-GOLM-ADAM-2011 Mass Spectral library. Metabolites were considered tentatively identified with a spectral match score higher than 60 and RI-deviation (Ri-RI(lib)) lower than 8. Data were normalized to the total area for each chromatogram. Values are expressed as mean ± SD of three determinations.
tr, trace amount (<0.01%);
-: not detected.
SupplementalTable 1 Phytochemical components of citrus essential oils (continued)
# / RT / Ri-RI(lib) / Score / Library / Name / Citrus essential oils(min) / (min) / Gu / Ji / Vo / Me / Al / Ra / Bu / St / Cht / Chp
1 / 15.0376 / -7.8 / 83 / Adam / α-Thujene / 1.11±0.02 / 0.08±0.01 / 0.15±0.02 / 1.05±0.13 / 0.05±0.02 / 0.94±0.11 / 0.67±0.01 / tr / 0.30±0.02 / 0.01±0.00
2 / 15.4750 / -5.1 / 98 / Adam / α-Pinene / 5.26±0.15 / 1.35±0.04 / 1.82±0.14 / 3.24±0.50 / 1.21±0.11 / 4.30±0.56 / 3.67±0.34 / 0.49±0.28 / 1.74±0.03 / 0.82±0.04
3 / 17.3848 / 4.4 / 97 / Adam / Sabinene / 3.19±0.44 / 7.54±1.98 / 13.64±2.06 / 0.28±0.01 / 4.48±1.71 / 2.39±0.17 / 0.06±0.01 / 0.23±0.19 / 0.07±0.03 / 0.20±0.04
4 / 18.0693 / 2.1 / 95 / Adam / Myrcene / 3.94±0.03 / 5.65±0.12 / 5.86±0.25 / 4.40±0.06 / 7.07±1.50 / 3.62±0.17 / 7.82±0.24 / 9.31±2.72 / 9.02±0.15 / 11.32±0.19
5 / 18.8887 / 2.3 / 79 / Noble / α-Phellandrene / tr / tr / 0.01±0.00 / tr / tr / tr / tr / tr / tr / tr
6 / 19.3785 / 2.3 / 79 / Noble / α-Terpinene / 0.41±0.08 / 0.18±0.05 / 0.51±0.14 / 0.22±0.02 / 0.19±0.07 / 0.31±0.03 / 0.02±0.01 / 0.03±0.01 / 0.07±0.02 / tr
7 / 19.9738 / 3.6 / 95 / Noble / R-(+)-Limonene / 61.24±1.28 / 83.08±1.95 / 75.51±1.23 / 70.37±0.27 / 84.38±0.78 / 64.09±0.40 / 55.05±2.26 / 84.28±0.75 / 64.28±0.74 / 85.67±0.36
8 / 20.2929 / 6.2 / 78 / Noble / Eucalyptol / 0.36±0.12 / tr / 0.01±0.00 / 0.12±0.02 / tr / 0.20±0.05 / tr / 0.01±0.00 / tr / 0.01±0.00
9 / 21.1755 / -2.2 / 67 / Adam / para-Mentha-3,8-diene / 21.42±0.73 / 0.70±0.12 / 1.53±0.42 / 18.00±0.22 / 1.03±0.38 / 21.26±0.50 / 19.18±1.33 / 0.40±0.10 / 16.09±0.11 / 0.16±0.08
10 / 22.1857 / 0 / 95 / Noble / Terpinolene / 0.95±0.08 / 0.16±0.03 / 0.31±0.06 / 0.90±0.02 / 0.18±0.03 / 0.81±0.03 / 0.47±0.09 / 0.10±0.04 / 0.42±0.02 / 0.03±0.00
11 / 22.5936 / Unknown / 0.01±0.00 / tr / 0.03±0.01 / 0.06±0.01 / tr / 0.01±0.00 / 0.03±0.00 / 0.09±0.08 / 0.01±0.00 / 0.03±0.00
12 / 22.8511 / Unknown / 0.06±0.00 / 0.03±0.01 / 0.05±0.02 / 0.04±0.00 / 0.02±0.00 / 0.05±0.00 / 0.04±0.00 / 0.17±0.08 / 0.05±0.01 / 0.02±0.00
13 / 23.1121 / Unknown / tr / — / tr / tr / — / tr / tr / tr / tr / tr
14 / 23.7966 / Unknown / 0.03±0.01 / tr / tr / tr / tr / 0.02±0.00 / 0.01±0.00 / tr / tr / 0.01±0.00
15 / 24.0737 / Unknown / 0.01±0.00 / 0.01±0.00 / 0.01±0.00 / 0.02±0.00 / 0.01±0.00 / 0.01±0.00 / 0.05±0.01 / 0.01±0.00 / 0.01±0.00 / 0.01±0.00
16 / 24.3212 / Unknown / 0.04±0.04 / tr / tr / 0.01±0.00 / 0.01±0.00 / 0.02±0.01 / 0.07±0.023 / tr / 0.01±0.00 / —
17 / 24.5631 / 5.2 / 82 / Adam / Isopulegol / 0.02±0.01 / tr / 0.02±0.01 / tr / tr / 0.02±0.00 / tr / tr / tr
18 / 26.3636 / 3.7 / 64 / Adam / Octanol acetate / 0.23±0.01 / 0.10±0.02 / 0.10±0.01 / 0.03±0.01 / 0.10±0.04 / 0.18±0.00 / 0.11±0.05 / 1.91±1.26 / 0.46±0.03 / 0.02±0.01
19 / 27.9811 / Unknown / 0.02±0.00 / 0.01±0.00 / 0.01±0.00 / 0.01±0.00 / 0.02±0.01 / 0.01±0.00 / 0.09±0.02 / 0.03±0.02 / 0.01±0.01 / 0.01±0.00
20 / 28.1059 / Unknown / 0.04±0.00 / 0.01±0.00 / 0.02±0.00 / 0.01±0.00 / 0.01±0.01 / 0.07±0.01 / 0.07±0.00 / 0.03±0.01 / 0.01±0.00 / 0.01±0.00
21 / 28.3492 / Unknown / 0.04±0.01 / 0.01±0.00 / 0.01±0.00 / 0.10±0.02 / 0.01±0.01 / 0.07±0.01 / 5.24±1.55 / 0.20±0.18 / 0.02±0.00 / 0.05±0.02
22 / 29.4755 / Unknown / 0.04±0.01 / 0.02±0.00 / 0.02±0.01 / 0.03±0.00 / 0.02±0.01 / 0.03±0.01 / 0.07±0.01 / 0.06±0.04 / 0.06±0.01 / 0.01±0.00
23 / 30.3954 / Unknown / tr / tr / — / tr / tr / tr / tr / tr / 0.01±0.00 / tr
24 / 30.5727 / -0.3 / 61 / Adam / Citronellyl acetate / 0.13±0.00 / 0.50±0.03 / 0.15±0.05 / 0.02±0.00 / 0.59±0.28 / 0.14±0.01 / 0.19±0.01 / 0.19±0.13 / 0.20±0.03 / 0.15±0.02
25 / 30.7500 / Unknown / tr / — / tr / 0.01±0.00 / — / tr / tr / tr / tr / tr
26 / 30.8450 / Unknown / 0.02±0.00 / 0.30±0.02 / 0.01±0.00 / 0.06±0.00 / 0.29±0.06 / 0.02±0.00 / 2.52±0.21 / 0.08±0.06 / 0.27±0.01 / 0.29±0.02
27 / 31.3843 / Unknown / 0.02±0.00 / 0.08±0.01 / 0.01±0.00 / 0.01±0.00 / 0.09±0.05 / 0.02±0.00 / 4.10±0.89 / 0.56±0.47 / 0.15±0.02 / 0.69±0.04
28 / 31.5269 / Unknown / tr / tr / tr / tr / tr / tr / tr / tr / tr / tr
29 / 31.6301 / -2.7 / 63 / Adam / 7-epi-Sesquithujene / tr / tr / tr / 0.02±0.00 / tr / tr / tr / tr / tr / —
30 / 31.9340 / Unknown / 0.05±0.01 / tr / tr / 0.09±0.00 / tr / 0.04±0.01 / tr / 0.04±0.05 / 0.05±0.03 / tr
31 / 32.3138 / Unknown / 0.02±0.00 / tr / 0.01±0.01 / 0.01±0.00 / 0.01±0.01 / 0.01±0.00 / 0.01±0.00 / 0.09±0.10 / 0.08±0.01 / 0.01±0.00
32 / 32.5449 / Unknown / 0.05±0.00 / 0.03±0.00 / 0.02±0.00 / 0.02±0.00 / 0.03±0.01 / 0.05±0.00 / 0.07±0.00 / 0.02±0.01 / 0.01±0.00 / 0.01±0.00
33 / 32.8427 / Unknown / 0.25±0.04 / 0.05±0.00 / 0.07±0.02 / 0.01±0.00 / 0.05±0.01 / 0.20±0.01 / 0.05±0.01 / 1.02±0.79 / 0.10±0.00 / 0.25±0.01
34 / 32.9142 / -2.6 / 82 / Noble / (-)-trans-Caryophyllene / 0.01±0.00 / tr / tr / tr / tr / 0.01±0.00 / tr / 0.03±0.04 / tr / tr
35 / 33.0699 / -1.5 / 79 / Adam / cis-Prenyl limonene / tr / tr / tr / tr / tr / tr / tr / 0.01±0.01 / tr / tr
36 / 33.1566 / Unknown / 0.03±0.00 / 0.02±0.00 / 0.01±0.01 / 0.01±0.00 / 0.01±0.00 / 0.03±0.01 / 0.01±0.00 / 0.01±0.01 / 0.03±0.01 / tr
37 / 33.1999 / Unknown / 0.04±0.01 / 0.02±0.00 / 0.01±0.00 / 0.02±0.01 / 0.03±0.02 / 0.04±0.01 / 0.05±0.00 / 0.02±0.01 / 0.06±0.01 / 0.01±0.00
38 / 33.4176 / Unknown / 0.06±0.00 / 0.01±0.00 / 0.01±0.00 / 0.24±0.00 / 0.01±0.01 / 0.06±0.00 / 0.13±0.00 / 0.17±0.16 / 0.73±0.09 / 0.10±0.01
39 / 33.8017 / Unknown / 0.04±0.00 / 0.02±0.00 / 0.01±0.00 / 0.02±0.00 / 0.02±0.00 / 0.04±0.00 / 0.02±0.00 / 0.02±0.02 / 0.02±0.00 / tr
40 / 33.8684 / Unknown / tr / tr / tr / tr / tr / tr / tr / tr / tr / tr
41 / 34.4533 / Unknown / 0.29±0.12 / 0.03±0.00 / 0.01±0.00 / 0.19±0.03 / 0.03±0.01 / 0.31±0.04 / 0.06±0.01 / 0.18±0.10 / 3.84±0.73 / 0.05±0.00
42 / 34.5122 / 3.6 / 90 / Adam / trans-Muurola-4(14),5-diene / 0.29±0.12 / 0.02±0.00 / tr / 0.18±0.01 / 0.01±0.01 / 0.29±0.03 / tr / 0.06±0.07 / 1.63±0.59 / 0.01±0.00
43 / 34.5742 / Unknown / tr / — / — / — / — / tr / tr / — / — / —
44 / 34.7472 / 1 / 89 / Adam / α-Farnesene / 0.03±0.00 / tr / tr / 0.01±0.00 / tr / 0.20±0.00 / tr / 0.02±0.03 / 0.04±0.03 / 0.02±0.00
45 / 34.8604 / Unknown / 0.05±0.06 / tr / 0.02±0.02 / 0.03±0.02 / tr / 0.13±0.01 / 0.02±0.00 / 0.01±0.01 / 0.01±0.01 / 0.01±0.00
46 / 34.9696 / 1.1 / 80 / Adam / β-Curcumene / 0.12±0.02 / 0.03±0.00 / 0.02±0.01 / 0.03±0.00 / 0.02±0.01 / 0.12±0.00 / 0.02±0.00 / tr / 0.01±0.00 / tr
47 / 35.3234 / 1.6 / 64 / Adam / Zonarene / 0.08±0.01 / tr / tr / 0.03±0.00 / tr / 0.08±0.00 / tr / 0.13±0.13 / 0.15±0.05 / 0.02±0.00
Metabolite derivatives were tentatively identified by matching retention time as well as mass spectra with those in NF-GOLM-ADAM-2011 Mass Spectral library. Metabolites were considered tentatively identified with a spectral match score higher than 60 and RI-deviation (Ri-RI(lib)) lower than 8. Data were normalized to the total area for each chromatogram. Values are expressed as mean ± SD of three determinations.
tr, trace amount (<0.01%);
-: not detected.