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Original article
32 (
2
); 1562-1568
doi:
10.1016/j.jksus.2019.12.012

Chemical components and functions of Taxus chinensis extract

, , , , ,
 School of Materials Science and Engineering & Hunan Green Home Engineering Research Center, Central South University of Forestry and Technology, 410004 Changsha, China
Received: , Accepted: ,
© The Author(s) 2019
Disclaimer:
This article was originally published by Elsevier and was migrated to Scientific Scholar after the change of Publisher.

Peer review under responsibility of King Saud University.

Abstract

Taxus chinensis is a National level protected plant and has been for a long time, since it grows slowly and has low regenerative capacity. Consequently, no large base of raw material forest of taxus was formed. This study used Taxus chinensis as the study object, for analyzing the chemical composition of T. chinensis extract via fourier transform infrared spectroscopy (FT-IR) and gas chromatography/mass spectrometry (GC/MS). 37 types of chemical components were detected. These were mainly ethers (asarone, dibutyl phthalate, diisobutyl phthalate), alcohols (nerolidol, Myo-inositol, 4-C-methyl-, trans-Sinapyl alcohol), acids (3,4-dimethoxycinnamic acid, palmitic acid, oleic Acid), flavonoids (macckiain, formononetin), ketone (4-hydroxy-.beta.-ionone, pseudobaptigenin), phenols (methyleugenol), esters (triacetin), aldehydes (sinapinaldehyde), and pyridines (alpha-methylstyrene). This chemical component could be directly or indirectly used for bioengineering, pharmaceutical engineering, the cosmetic industry, and other chemical industries.

Keywords

Taxus chinensis
Extract
Function
FT-IR
GC/MS
1

1 Introduction

Taxus chinensis is endemic to China and its main distribution is in the provinces south of the Yangtze River Basin. T. chinensis is a member of the family Taxaceae and the genus Taxus. All species of taxus contain highly toxic ingredients but provide a potentially rich source of biological active diterepenoids (Li et al., 2008; Qiu et al., 2009) They grow slowly and are protected at National level. Taxol (paclitaxel) has been one of the best natural anticancer drugs in the past few decades (Mu and Feng, 2003). It has been widely used for the treatment of breast cancer, lung cancer, ovarian cancer, and part of head and neck cancer. The supply of taxol is extracted from taxus bark (Shen et al., 2017). Relying on other chemical component from taxus due to the scarcity of taxol, slow growth and low paclitaxel. Therefore, study of the extract of chemical components and functions of T. chinensis has become very meaningful.

2

2 Material and methods

The material of this study was obtained from the T. chinensis trunk. First, we ground three parts of the material (bark, sapwood, and heartwood of T. chinensis) in a micro plant grinding machine to obtain wood powder, and the powder was put into a drying oven, set at a temperature of 100 °C and dry for 6 h to evaporate all free water from the sample.

Then, we used four different experiment levels: “0” represented the untreated wood powder; “1”, “2”, and “3” represented the material for the extraction experiment using ethanol, ethanol & methanol, and ethanol & benzene as solvent (Table 1).

Table 1 Sample number.
Solvent Bark Sapwood Heartwood
Untreated – B0 S0 H0
Extractive Ethanol B1 S1 H1
Ethanol & Methanol B2 S2 H2
Ethanol & Benzene B3 S3 H3

2.1

2.1 FT-IR analysis

The dried T. chinensis powder was filtered through a 200-mesh sieve. This experiment used pure KBr as a solid dispersion medium (Mi et al., 2019). The finely ground T. chinensis powder was dispersed in KBr at 1:100. The range of the spectrum was set to 400–4000 cm−1 (Castaldi et al., 2010; Li et al., 2017a, 2017b; Maréchal and Chanzy, 2000).

2.2

2.2 GC/MS analysis

The chromatographic column was HP-5MS (30 m × 250 μm × 0.25 μm), capillary column was elastic quartz, carrier gas was high purity He, flow rate was 1 mL/min, and the shunting mode was used with a split ratio of 20:1. The temperature of GC program started at 50 °C, increased to 250 °C at a rate of 8℃/min, increased to 300℃ at a rate of 5℃/min. MS program scanning quality range was 30–600 amu, ionization voltage was 70 eV, and ionization current (EI) was 150 μA. The ion source temperature was 230℃, quadrupole temperature was 150℃ (Daferera et al., 2000; Ma et al., 2008a, 2008b; Wang et al., 2005).

3

3 Results and discussion

3.1

3.1 Analysis of FT-IR

This analysis used materials extracted via different slovents. Due to the ubiquitous solvent effect, interactions between sample molecules and solvent molecules would change the frequency and intensity of vibration of the sample molecule (Peng et al., 2017a, 2017b). For the same raw material, this may thus obtain different results due to the different solvents.

Fig. 1 and Table 2 show the results of FT-IR spectra of T. chinensis bark. We could see that in different experimental levels, the same part of the FT-IR spectrum of wood powder differed. The spectrograms show that transmittance of B0 was 76.24% at 3341 cm−1, transmittance of B1, B2, and B3, respective were 61.07%, 58.31%, and 43.87% at 3441 cm−1 (O–H stretching vibration). Furthermore, according to other studies we know that the characterized absorption peaks of cellulose were 2900 cm−1, 1425 cm−1, 1370 cm−1, and 895 cm−1. Transmittance of B0 was 85.21% at 2934 cm−1, transmittance of B1, B2, and B3, respective were 81.58%, 79.75%, and 68.29% at 3441 cm−1 (C–H stretching vibration). At 1370 cm−1 (C–H flexural vibration), transmittance of B0, B1, B2, and B3 were 89.58%, 78.30%, 79.73%, and 68.95%, respectively. This showed that cellulose was hydrolyzed to differently extent and it was hydrolyzed more in mixed solvent of ethanol and benzene.

FT-IR spectrum of T. chinensis bark under four treatment methods.
Fig. 1
FT-IR spectrum of T. chinensis bark under four treatment methods.
Table 2 Analytical results of FT-IR spectra of T. chinensis bark.
Absorption peak attribution Absorption peak (cm−1) Chemical component
B0 B1 B2 B3
O–H Stretching vibration 3341 3441 3441 3441 Cellulose, Hemicellulose, carboxylic acid, alcohol
C–H Stretching vibration 2934 2903 2903 2903 Cellulose
Benzene ring stretching vibration 1618 1618 1618 1618 Lignin
1522 1516 1516 1516 Lignin
1452 1454 1454 1454 Lignin
C–H Flexural vibration 1373 1369 1369 1369 Cellulose, Hemicellulose
S-ring, 5-substituted G-ring 1317 1317 1317 1317 Lignin
C–O Stretching vibration 1059 1056 1056 1056 Cellulose, Hemicellulose

At 1618 cm−1 (benzene ring stretching vibration), transmittance of B0, B1, B2, and B3 were 79.15%, 61.62%, 60.32%, and 45.55%, respectively. At about 1518 cm−1 (benzene ring stretching vibration), transmittance of B0, B1, B2, and B3 were 89.43%, 71.92%, 72.44%, and 59.73%, respectively (Peng et al., 2017a, 2017b). At about 1454 cm−1 (benzene ring stretching vibration), transmittance of B0, B1, B2, and B3 were 88.22%, 76.08%, 77.88%, and 65.47%, respectively. At 1317 cm−1 (S-ring, 5-substituted G-ring), transmittance of B0, B1, B2, and B3 were 88.48%, 76.85%, 77.60%, and 66.90%, respectively. This shows that the transmittance of B1 was close to B2 and their transmittances were weaker than that of B0. The transmittance of B3 was the weakest. This shows that lignin was partially hydrolyzed in the mix solvent of ethanol and benzene, and a small amount of hydrolyed in the ethanol solvent and the mixed solvent of ethanol and methanol.

At about 1056 cm−1 (C–O Stretching vibration), transmittance of B0, B1, B2, and B3 were 81.61%, 66.46%, 65.02%, and 53.70%, respectively. In combination with the above data, this shows that hemicelluloses was partially hydrolyzed by organic solvents (Ma et al., 2008a, 2008b; Río et al., 2007; Schwanninger et al., 2004).

Fig. 2 and Table 3 show the results of FT-IR spectra of T. chinensis sapwood. The characterized absorption peaks of cellulose, at about 2898 cm−1 (C–H Stretching vibration), transmittance of B0, B1, B2, and B3 were 79.08%, 86.75%, 78.24%, and 81.12%, respectively. At about 1426 cm−1 (CH2 Flexural vibration, CH2 Scissor vibration), transmitance of B0, B1, B2, and B3 are 80.59%, 86.04%, 81.34%, and 75.80%, respectively. At about 1373 cm−1 (C–H Stretching vibration), transmittance of B0, B1, B2, and B3 are 81.78%, 89.72%, 84.33%, and 77.23%, respectively. The results show that cellulose was hydrolyzed in small amount. The characterized absorption peaks of hemicellulose, at 1742 cm−1 (C=O Stretching vibration), transmittance of B0, B1, B2, and B3 were 85.05%, 79.01%, 75.14%, and 79.02%, respectively. The results show that a small amount of hemicellulose was hydrolyzed. The characterized absorption peaks of lignin, at about 1653 cm−1 (C=O Stretching vibration), transmittance of B0, B1, B2, and B3 were 81.14%, 76.87%, 74.97%, and 75.48%, respectively. At 1512 cm−1 (benzene ring stretching vibration), transmittance of B0, B1, B2, and B3 were 78.23%, 70.36%, 66.33%, and 69.21%, respectively. At about 1460 cm−1 (C–H Flexural vibration, CH2, CH3 asymmetric flexural), transmittance of B0, B1, B2, and B3 were 80.44%, 80.52%, 76.73%, and 74.56%, respectively. The results show that a small amount of lignin was hydrolyzed.

FT-IR spectrum of T. chinensis sapwood under four treatment methods.
Fig. 2
FT-IR spectrum of T. chinensis sapwood under four treatment methods.
Table 3 Analytical results of FT-IR spectra of T. chinensis sapwood.
Absorption peak attribution Absorption peak (cm−1) Chemical component
S0 S1 S2 S3
O–H Stretching vibration 3360 3412 3412 3412 Cellulose, Hemicellulose, carboxylic acid, alcohol
C–H Stretching vibration 2899 2897 2899 2897 Cellulose
C=O Stretching vibration 1742 1742 1744 1740 Hemicellulose
1655 1653 1653 1653 Lignin
Benzene ring stretching vibration 1512 1512 1514 1512 Lignin
C–H Flexural vibration, CH2, CH3 Asymmetric flexural vibration 1458 1462 1462 1456 Lignin
CH2 Flexural vibration, CH2 Scissor vibration 1427 1425 1425 1427 Cellulose, Lignin
C–H Stretching vibration 1373 1379 1369 1371 Cellulose, Hemicellulose,
G-ring, Acyloxy CO–O stretching vibration 1269 1271 1269 1269 Lignin
C–O Stretching vibration 1030 1024 1026 1014 Cellulose, Hemicellulose, Lignin

Fig. 3 and Table 4 show the results of FT-IR spectra of T. chinensis heartwood. The characterized absorption peaks of cellulose, at about 2902 cm−1 (C–H Stretching vibration), transmittance of B0, B1, B2, and B3 were 75.01%, 81.94%, 82.15%, and 92.46%, respectively. At about 1426 cm−1 (CH2 Flexural vibration, CH2 Scissor vibration), transmittance of B0, B1, B2, and B3 were 76.57%, 84.74%, 78.73%, and 91.43%, respectively. The results show that a small amount of cellulose was hydrolyzed. The characterized absorption peaks of hemicellulose, at 1740 cm−1 (C=O Stretching vibration), transmittance of B0, B1, B2, and B3 were 85.26%, 87.79%, 75.88%, and 85.02%, respectively. The results show that a small amount of hemicellulose was hydrolyzed. The characterized absorption peaks of lignin, at about 1650 cm−1 (C=O Stretching vibration), transmittance of B0, B1, B2, and B3 were 77.63%, 83.51%, 67.08%, and 84.60%, respectively. At 1513 cm−1 (Benzene ring stretching vibration), transmittance of B0, B1, B2, and B3 were 70.47%, 81.23%, 65.93%, and 77.87%, respectively. At about 1458 cm−1 (C–H Flexural vibration, CH2, CH3 Asymmetric flexural), transmittance of B0, B1, B2, and B3 were 74.74%, 84.23%, 76.30%, and 87.96%, respectively. The results show that lignin was partially hydrolyzed in the mix solvent of ethanol and methanol, and a small amount of hydrolyed in the others solvent.

FT-IR spectrum of T. chinensis heartwood under four treatment methods.
Fig. 3
FT-IR spectrum of T. chinensis heartwood under four treatment methods.
Table 4 Analytical results of FT-IR spectra of T. chinensis heartwood.
Absorption peak attribution Absorption peak (cm−1) Chemical component
H0 H1 H2 H3
O–H Stretching vibration 3360 3393 3360 3433 Cellulose, Hemicellulose, carboxylic acid, alcohol
C–H Stretching vibration 2907 2900 2900 2897 Cellulose
C=O Stretching vibration 1740 1740 1740 1744 Hemicellulose
C=O Stretching vibration 1647 1651 1651 1653 Lignin
Benzene ring stretching vibration 1514 1512 1514 1514 Lignin
C–H Flexural vibration, CH2, CH3 Asymmetric flexural vibration 1458 1456 1456 1462 Lignin
CH2 Flexural vibration, CH2 Scissor vibration 1427 1427 1425 1423 Cellulose, Lignin
G-ring, Acyloxy CO-O stretching vibration 1271 1271 1267 1271 Lignin
C-O Stretching vibration 1030 1030 1030 1020 Cellulose, Hemicellulose, Lignin

According to FT-IR analysis, the absorption peaks did not indicate significant migration. This indicates that in the extraction process, the chemical components of the samples did not change too much.

3.2

3.2 Analysis of GC/MS

Table 5 shows that: via analysis of GC–MS, in the bark of T. chinensis, the experiment of extracting with ethanol solution, nine types of chemical components which occupied 53.93% of total peaks areas were identified. There were benzene,1,2,3-trimethoxy-5-(2-propenyl)- (47.50%), 4,6-diamino-3-[4-methoxybenzyl]-1H-pyrazolo[3,4-d]pyrimidine (3.21%), 1,2-Benzenedicarboxylic acid, butyl 8-methylnonyl ester (0.63%), nerolidol (0.55%) and estra-1,3,5(10)-trien-17.beta.-ol (0.55%).

Table 5 Analytical results of T. chinensis bark powder by GC/MS.
No. Compound B1 B2 B3
RT (min) Area (%) RT (min) Area (%) RT (min) Area (%)
1 .alpha.-Methylstyrene – – – – 5.51 0.59
2 Triacetin – – – – 11.83 0.29
3 Methyleugenol 12.76 0.32 12.76 0.23 12.75 0.27
4 Benzene,1,4-dimethoxy-2,3,5,6-tetramethyl- 14.51 0.33 14.51 0.36 14.51 0.39
5 Benzene,1,2,3-trimethoxy-5-(2-propenyl)- 15.12 47.50 15.12 29.53 15.14 46.23
15.19 0.36
6 4-Hydroxy-.beta.-ionone 15.19 0.46 – – 15.19 0.43
7 Asarone – – 15.22 0.53 – –
8 Nerolidol 15.22 0.55 – – 15.23 0.58
9 4-Allyl-2,6-Dimethoxyphenol – – 15.82 0.15 – –
10 Benzene,1,2,3-trimethoxy-5-(2-propenyl)- – – 16.48 0.31 16.48 0.25
11 1,2-Benzenedicarboxylic acid, bis(2-methylpropyl) – – – – 19.39 3.31
12 3,4-Dimethoxycinnamic acid – – – – 19.89 0.59
13 2,2-Dimethyl-6-methylene-1-[3,5-dihydroxy-1- – – – – 20.45 0.26
14 Estra-1,3,5(10)-trien-17.beta.-ol 20.46 0.55 20.46 0.35 – –
15 1,2-Benzenedicarboxylic acid, butyl 8-methylnonyl ester 20.55 0.63 – – – –
16 Dibutyl phthalate – – – – 20.55 2.32
17 .gamma.-Sitosterol – – – – 25.59 0.34
18 1H-2,8a-Methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one, 1a,2,5,5a,6,9,10,10a-octahydro-5,5a,6-trihydroxy-1,4-bis(hydroxymethyl)-1,7,9-trimethyl-, [1S-(1.alpha.,1a.alpha.,2.alpha.,5.beta.,5a.beta.,6.beta.,8a.alpha.,9.alpha.,10a.alpha.)]- 25.72 0.38 – – 25.72 0.36
19 4,6-Diamino-3-[4-methoxybenzyl]-1H-pyrazolo[3,4-d]pyrimidine 27.33 3.21 – – 27.33 3.11

In the experiment of extracting the mixed solution of ethanol and methanol, seven types of chemical components were identified which occupied 31.82% of total peaks areas. There were benzene,1,2,3-trimethoxy-5-(2-propenyl)- (29.89%) and asarone (0.53%).

In the experiment for extracting the mixed solution of ethanol and benzene, 15 types of chemical components were identified, which occupied 59.32% of total peaks areas. These were: benzene,1,2,3-trimethoxy-5-(2-propenyl)- (46.23%), 1,2-benzenedicarboxylic acid, bis(2-methylpropyl) (3.11%), 4,6-diamino-3-[4-methoxybenzyl]-1H-pyrazolo[3,4-d]pyrimidine (3.11%), dibutyl phthalate (2.32%), alpha-methylstyrene (0.59%), 3,4-dimethoxycinnamic acid (0.59%), nerolidol (0.58%) and 4-hydroxy-.beta.-ionone (0.43%).

Table 6 shows that via analysis of GC–MS, in the sapwood of T. chinensis, the experiment of extracting with ethanol solution, eight types of chemical components were identified, which occupied 35.09% of total peaks areas. These were benzene,1,2,3-trimethoxy-5-(2-propenyl)- (30.61%), gamma-sitosterol (2.29%) and 1 h-2,8a-Methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one,1a,2,5,5a,6,9,10,10a-octahydro-5,5a,6-trihydroxy-1,4-bis(hydroxymethyl)-1,7,9-trimethyl-,[1S-(1.alpha.,1a.alpha.,2.alpha.,5.beta.,5a.beta.,6.beta.,8a.alpha.,9.alpha.,10a.alpha.)]- (1.20%).

Table 6 Analytical results of T. chinensis sapwood powder via GC/MS.
No. Compound S1 S2 S3
RT (min) Area (%) RT (min) Area (%) RT (min) Area (%)
1 .alpha.-Methylstyrene – – – – 5.51 0.61
2 Triacetin – – – – 11.83 0.19
3 Methyleugenol 12.76 0.19 – – 12.75 0.25
4 Benzene,1,4-dimethoxy-2,3,5,6-tetramethyl- 14.51 0.23 14.51 0.30 14.51 0.23
5 Benzene,1,2,3-trimethoxy-5-(2-propenyl)- 15.11 30.61 15.12 18.10 15.12 29.69
15.18 0.14
6 4-Hydroxy-.beta.-ionone 15.18 0.18 – – 15.19 0.19
7 6-epi-Shyobunol 15.22 0.16 – – 15.22 0.22
8 Myo-Inositol, 4-C-methyl- – – – – 17.61 5.16
9 Diisobutyl phthalate – – – – 19.39 2.13
10 Dibutyl phthalate – – – – 20.55 1.49
11 Benzene,1,2,3-trimethoxy-5-(2-propenyl)- – – 20.85 0.23 – –
12 2-[4-methyl-6-(2,6,6-trimethylcyclohex-1-enyl)hexa-1,3,5-trienyl]cyclohex-1-en-1-carboxaldehyde 23.62 0.23 – – 23.29 0.21
23.62 0.25
13 1H-2,8a-Methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one, 1a,2,5,5a,6,9,10,10a-octahydro-5,5a,6-trihydroxy-1,4-bis(hydroxymethyl)-1,7,9-trimethyl-, [1S-(1.alpha.,1a.alpha.,2.alpha.,5.beta.,5a.beta.,6.beta.,8a.alpha.,9.alpha.,10a.alpha.)]- 25.50 1.2 23.62 0.1 24.18 0.21
24.38 0.27
14 .gamma.-Sitosterol 25.68 2.29 – – 25.50 0.52
25.68 2.00
15 4,6-Diamino-3-[4-methoxybenzyl]-1H-pyrazolo[3,4-d]pyrimidine – – 27.33 2.57 – –
16 S-Indacene-1,7-dione,2,3,5,6-tetrahydro-3,3,4,5,5,8-hexamethyl- – – 27.67 14.46 – –
17 Macckiain – – 28.67 1.62 – –
29.11 3.50

In the experiment for extracting the mixed solution of ethanol and methanol, seven types of chemical components were identified, which occupied 41.02% of total peaks areas. These were benzene,1,2,3-trimethoxy-5-(2-propenyl)- (18.24%), s-indacene-1,7-dione,2,3,5,6-tetrahydro-3,3,4,5,5,8-hexamethyl- (14.46%), macckiain (5.12%) and 4,6-diamino-3-[4-methoxybenzyl]-1H-pyrazolo[3,4-d]pyrimidine (2.57%).

In the experiment for extracting the mixed solution of ethanol and benzene, 13 types of chemical components were identified, which occupied 43.62% of total peaks areas. These were benzene,1,2,3-trimethoxy-5-(2-propenyl)- (29.69%), Myo-inositol, 4-c-methyl- (5.16%), gamma-sitosterol (2.52%), diisobutyl phthalate (2.13%) and dibutyl phthalate (1.49%).

Table 7 shows that vie analysis of GC–MS, in the heartwood of T. chinensis, the experiment of extracting with ethanol solution, 12 types of chemical components were identified, which occupied 43.28% of total peaks areas. These were formononetin (17.71%), Myo-inositol, 4-C-methyl- (8.19%), pseudobaptigenin (5.40%), pseudobaptigenin (4.79%), macckiain (2.32%), nerolidol (1.51%), dibenz[a,c]cyclohexane,2,4,7-trimethoxy- (1.07%) and oleic acid (0.82%).

Table 7 Analytical results of T. chinensis heartwood powder via GC/MS.
No. Compound H1 H2 H3
RT (min) Area (%) RT (min) Area (%) RT (min) Area (%)
1 .alpha.-Methylstyrene – – – – 5.51 0.91
2 Triacetin – – – – 11.83 0.37
3 Benzene,1,4-dimethoxy-2,3,5,6-tetramethyl- – – 14.45 0.28 – –
4 Benzene,1,2,3-trimethoxy-5-(2-propenyl)- 14.12 0.42 15.03 4.69 15.09 1.81
15.09 0.28
5 Nerolidol 15.21 1.51 15.15 1.27 15.21 7.04
6 Phenol,2,6-dimethoxy-4-(2-propenyl) – – 15.77 0.19 – –
7 [1,1′-Bicyclopropyl]-2-octanoic acid, 2′-hexyl-, methyl ester – – 16.26 0.11 16.35 0.49
16.32 0.09
8 Benzene,1,2,3-trimethoxy-5-(2-propenyl)- – – 16.44 0.13 – –
9 3-O-Methyl-d-glucose – – – – 17.23 3.33
10 Myo-Inositol, 4-C-methyl- 18.76 8.19 18.18 3.79 18.39 2.50
18.44 0.81
18.75 7.91
18.80 3.26
11 1,2-Benzenedicarboxylic acid, bis(2-methylpropyl) easter – – – – 19.39 3.82
12 Palmitic acid 20.46 0.31 – – – –
13 Dibutyl phthalate – – – – 20.55 2.76
14 Sinapinaldehyde 20.82 0.18 20.78 0.3 – –
15 trans-Sinapyl alcohol – – 20.90 0.46 – –
16 Oleic Acid 22.56 0.82 – – – –
17 Phenol,4-methyl-2-[5-(2-thienyl)pyrazol-3-yl]- – – 23.38 0.83 – –
18 1H-Cyclopropa[3,4]benz[1,2-e]azulene-5,7b,9,9a-tetrol,1a,1b,4,4a,5,7a,8,9-octahydro-3-(hydroxymethyl)-1,1,6,8-tetramethyl-,5,9,9a-triacetate,[1aR-(1a.alpha.,1b.beta.,4a.beta.,5.beta.,7a.alpha.,7b.alpha.,8.alpha.,9.beta.,9a.alpha.)]- 25.64 0.28 – – – –
19 .gamma.-Sitosterol – – – – 25.67 4.99
20 Dibenz[a,c]cyclohexane,2,4,7-trimethoxy- 25.87 0.47 – – – –
26.55 0.60
21 S-Indacene-1,7-dione,2,3,5,6-tetrahydro-3,3,4,5,5,8-hexamethyl- 27.67 4.79 – – – –
22 Macckiain 29.12 2.32 – – – –
23 Formononetin 31.57 17.71 – – – –
24 Pseudobaptigenin 32.00 5.40 – – – –

In the experiment for extracting the mixed solution of ethanol and methanol, 10 types of chemical components were identified, which occupied 12.14% of total peaks areas. There were benzene,1,2,3-trimethoxy-5-(2-propenyl)- (4.69%), Myo-inositol, 4-C-methyl- (3.79%) and nerolidol (1.27%).

In the experiment for extracting the mixed solution of ethanol and benzene, 10 types of chemical components were identified, which occupied 40.00% of total peaks areas. These were Myo-inositol, 4-C-methyl- (14.48%), nerolidol (7.04%), gamma-sitosterol (4.99%), 1,2-benzenedicarboxylic acid, bis(2-methylpropyl) easter (3.82%), 3-O-methyl-d-glucose (3.33%), dibutyl phthalate (2.76%), benzene,1,2,3-trimethoxy-5-(2-propenyl)- (1.81%) and alpha-methylstyrene (0.91%).

In conclusion, the extractive chemical components differed depending on the solvent used and the part of the wood. The chemical components of bark were the least, only about 10% of the whole tree; therefore, the extracts of bark were fewest. There was less cellulose and pentose in the bark. Heartwood had more organic solvent extraction and fewer lignin and cellulose than sapwood.

3.3

3.3 Functions of chemical components

Triacetin is also called Glyceryl Triacetate. It can be used as a cosmetic biocide, solvent and plasticizer of cosmetic. Experts have concluded that the use of triacetin in cosmetic formulations is safe. It is often used as a carrier for flavors and fragrances (Fiume, 2003). Transesterification of triacetin and methanol can be used with homogeneous alkali catalysts to produce biodiesel (López et al., 2005).

Methyleugenol has many functions, such as anti-fungal, anti-bacterial, anti-nematode, toxic effects on pathogens, and causing antifeedant and anti-pollination in insect herbivores (Huang et al., 2002; Tan and Nishida, 2012). As an added flavoring substance, methyleugenol is also a component present in the traditional diet (Smith et al., 2002).

Isolated asarone can function against excitotoxic neuronal death in primary cultured rat cortical cells. It has neuroprotective action (Cho et al., 2002). Asarones from the rhizomes of Acorus tatarinowii is considered as a new drugs for treating depression (Han et al., 2013), Asarone is the active components in Acorus tatarinowii Schott, which is the traditional Chinese medicine and has been used to treat epilepsy for several thousands of years (Deng et al., 2010).

Nerolidol is widely used in different industries, used in food flavoring, detergents and cleansers (Chan et al., 2016) Nerolidol has antifungal activity (Lee et al., 2007) and antiulcerogenic activity (Klopell et al., 2014a, 2014b). It can be used for the skin to improve skin lesions infected by M. gypseum. Nerolidol may be an effective supplement to topical antifungal drugs for clinical relief of dermatophytosis. Significantly improved oxidative stability using 4-allyl-2,6-dimethoxyphenol as an additive (Klopell et al., 2014a, 2014b). 3,4-Dimethoxycinnamic acid is a prospective dietary compound for prophylaxis of neurodegenerative diseases (Zanyatkin et al., 2017).

Dibutyl phthalate is used as a plasticizer in elastomers, resin solvent, textile lubricating agent and adhesives. Dibutyl phthalate can also be used as a perfume solvent in the production of cosmetics and as a lubricant for aerosol valves, a skin emollient, a suspension agent for solids in aerosols, and an antifoamer. Dibutyl phthalate is known to be a developmental and repreoductive toxicant. It may have an adverse effect on the uterus of rodents, at least in part of which is responsible for the loss of early embryos (Ema et al., 2000; Higuchi et al., 2003).

For FT-IR analysis, the absorption peaks did not migrate significantly. This shows that the chemical components of the samples did not change severely in the process of extraction. The absorption peak of FT-IR had some change due to the difference of extract solvents, and the chemical components were hydrolyzed to some extent.

In the analysis of GC/MS, 37 types of chemical components were detected. The extractive chemical components were different depending on the solvent used and the part of the wood. The chemical components of bark were fewest with only about 10% of the whole tree; therefore, the extracts of bark were the fewest. There was less cellulose and pentose in the bark. Heartwood had more organic solvent extraction and fewer lignin and cellulose than sapwood.

The following is part of the chemical components and functions:

Triacetin can be used as a cosmetic biocide, solvent in cosmetic formulations, plasticizer, and is commonly used as carrier for flavors and fragrances. Methyleugenol has anti-fungal, anti-bacterial, anti-nematode, and toxic effects on pathogens and is a traditional diet and as added flavoring substance. Asarone has neuroprotective action and it is a new therapeutic agent for curing depression. Nerolidol is widespread across shampoos, perfumes, detergents, cleansers, food flavoring, and antifungal drugs. 3,4-Dimethoxycinnamic acid can prevent neurodegenerative diseases. Dibutyl phthalate is used as a plasticizer in elastomers, textile lubricating agent, resin solvent, and in safety glass, printing inks, paper coatings, adhesives, skin emollient, and lubricants for aerosol valves.

Conflict of interest

All the authors hereby agreed and confirm that there is no conflict of interest for this research work and publication of this paper.

Acknowledgments

This work was financially supported by the National Natural Science Fundation of China (31872697). The Hunan Science Fund for Distinguished Young Scholars (16JJ1028).

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