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Molecules and functions of rosewood: Pterocarpus cambodianus
⁎Corresponding author at: School of Forestry, Henan Agricultural University, Zhengzhou 450002, China. pengwanxi@163.com (Wanxi Peng)
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Received: ,
Accepted: ,
This article was originally published by Elsevier and was migrated to Scientific Scholar after the change of Publisher.
Abstract
Pterocarpus is a high-end, expensive furniture materials collectively. Pterocarpus products have a certain human health function. In this paper, Pterocarpus cambodianus Pierre as an example, we study its human health components by using PY–GC–MS, TDS–GC–MS and GC–MS. The composition of known human health functions was studied by reviewing the literature. 1-Heptatriacotanol has anti-hypercholesterolemic effects. Cryptomeridiol is a natural product of anti-Alzheimer's disease and antispasmodic nature, and has a significant medicinal value. 7-Methyl-Z-tetradecen-1-ol acetate has the effect of heat and heat cough. .alpha.-Bisabolol can be used to treat leishmaniasis caused by Lactobacillus infants.
Keywords
Pterocarpus
Pterocarpus cambodianus Pierre
PY–GC–MS
GC–MS
TDS–GC–MS
Health care ingredients
1 Introduction
Pterocarpus cambodianus Pierre mainly grown in Vietnam, Laos, Malaysia, Thailand, belonging to Leguminosae, Pterocarpus L. Dalbergia cochinchinensis Pierre wood for the bulk material, tube hole can be seen with the eye, heartwood was reddish brown or purple red brown, with a strong woody flavor, rich in oil. Wood with high strength, big hardness, the surface with the depth of the stripes or landscape-like pattern, air dry density of 0.94–1.01 g/cm3. Its wood water leaching solution has obvious blue fluorescence phenomenon. Pterocarpus cambodianus Pierre commonly used to produce high-grade furniture, ornamental works of art and musical instruments. Traditionally, the Pterocarpus cambodianus Pierre is considered to be useful for human health functions. In this paper, the Pterocarpus cambodianus Pierre powder was analyzed by PY–GC–MS, TDS–GC–MS, TG and FT-IR; The extracts of ethanol, ethanol/benzene and ethanol/methanol in the Pterocarpus cambodianus Pierre were analyzed by GC–MS and FT-IR; To determine the active molecules of Pterocarpus cambodianus Pierre, figurative effect of human care function.
2 Material and methods
2.1 Materials
The Pterocarpus cambodianus Pierre used in the experiment was produced in Vietnam. When we do the experiment, the Pterocarpus cambodianus Pierre are first pulverized and then tested with the obtained wood powder. The ethanol, benzene and methanol used in the experiments were purely chromatographed. Quantitative filter paper should be extracted with ethanol for 12 h. The three extracts used in the experiment were ethanol, ethanol/benzene (volume ratio of 1:2) and ethanol/methanol (volume ratio of 1:1).
2.2 Experimental methods
2.2.1 Extraction method
The crushed and processed Pterocarpus cambodianus Pierre’s powder was weighed 3 parts and the mass was 10 g (accuracy was 1.0 mg). A well-weighed powder and 250 mL of ethanol, ethanol/benzene (1:2 by volume) and ethanol/methanol (1:1 by volume) were added in the three round bottom flasks respectively. And then refluxed at 85 °C, 82 °C and 80 °C for 4.5 h. The obtained extract was subjected to suction filtration on a circulating water type vacuum pump (YUHUA SHZ-D (III)) using a quantitative filter paper subjected to ethanol extraction treatment for 12 h. Finally, the obtained extract was steamed and concentrated by a rotary evaporator (YUHUA RE-2000A).
2.2.2 FT-IR method
Diospyros celebica’s powder and the concentrated extract refluxed by three kinds of extractants were subjected to FT-IR detection (ThermoFisher Nicolet, 670FT-IR). The scanning of each powder was collected at a spectral resolution of 4 cm−1 and the spectral range was 400–4000 cm−1 (Maruyama et al., 2001; Sukor et al., 2017).
2.2.3 TG method
The powder of Diospyros celebica was analyzed by thermogravimetric analyzer (TGA Q50 V20.8 Build 34). The carrier gas used in the experiment was high purity nitrogen and the nitrogen release rate was 60 mL/min. The temperature program of TG starts at 30 °C and rises to 250 °C at a rate of 5 °C/min. During the test, the sample's weight (%), Deriv. Weight (%/°C) were recorded (Zhang et al., 2009; Basheer et al., 2017).
2.2.4 GC–MS method
The three extracts were analyzed using a gas chromatography–mass spectrometer (Agilent GC–MS 7890B 5977A). Column HP-5MS (30 m × 250 μm × 0.25 μm). Elastic quartz capillary column, the carrier gas used for high purity helium, flow rate of 1 mL/min. The split ratio is 20:1. The temperature program of the GC starts at 50 °C, rises to 250 °C at a rate of 8 °C/min, and then rises to 300 °C at a rate of 5 °C/min. MS program scan mass range of 30–600 amu, ionization voltage of 70 eV, ionization current of 150 μA electron ionization (EI). The ion source and the quadrupole temperature were set at 230 °C and 150 °C, respectively.
2.2.5 TDS–GC–MS method
The Diospyros celebica’ powder was analyzed with thermal desorption-gas chromatography-mass spectrometry. TDS starting temperature of 30 °C, for 1 min, at 10 °C/min rate rose to 100 °C, keep 5 min, then 10 °C/min rate rose to 200 °C, the transmission line temperature of 230 °C. CIS starting temperature of −50 °C, hold 0.1 min, and then 10 °C/s rate rose to 230 °C, keep 1 min. Gas Chromatography–Mass Spectrometer (Agilent GC–MS 7890B 5977A). The temperature program of the GC starts at 50 °C, rises to 250 °C at a rate of 8 °C/min, and then rises to 300 °C at a rate of 5 °C/min. MS program scan mass range of 30–600 amu, ionization voltage of 70 eV, ionization current of 150 μA electron ionization (EI). The ion source and the quadrupole temperature were set at 230 °C and 150 °C, respectively. The analytical standard library was analyzed by NIST14.L.
2.2.6 PY–GC–MS method
The powder of Diospyros celebica was analyzed by thermal cracking-gas chromatography-mass spectrometry (CDS5200-trace1310 ISQ). The carrier gas used for high purity helium, the pyrolysis temperature was 500 °C, the heating rate was 20 °C/ms, and the pyrolysis time was 15 s. The pyrolysis product transfer line and the injection valve temperature are set to 300 °C; Column TR-5MS; Capillary column (30 m × 0.25 mm × 0.25 μm); Shunt mode, split ratio of 1:60, shunt rate of 50 mL/min. The temperature of the GC program starts at 40 °C for 2 min, rises to 120 °C at a rate of 5 °C/min, and then rises to 200 C at a rate of 10 °C/min for 15 min. Ion source (EI) temperature of 280 °C, scanning range of 28–500 amu.
3 Results
3.1 FT-IR analysis
Fig. 1 shows the infrared comparison spectra of the Pterocarpus cambodianus Pierre powder and the three extracts. The infrared spectrum of 3360 cm−1 is the O—H stretching vibration in the cellulose, phenol, alcohol, carboxylic acid compounds (Iwaki and Dlott, 2000; Ismail and Hanafiah, 2017). The infrared spectrum of 2900 cm−1 is C—H stretching vibration and C—H bending vibration in cellulose and hemicellulose (Maroni et al., 2005; Halim and Phang, 2017). The infrared spectrum of 1738 cm−1 is C⚌O stretching vibration in hemicellulose, lipid, ketone compounds; There is the lignin aromatic carbon skeleton vibration at 1600 cm−1, 1510 cm−1. The infrared spectrum of 1425 cm−1 is the CH2 bending vibration and the CH2 shear vibration in the lignin, the cellulose (Ito and Nakanaga, 2010; Aziz and Hanafiah, 2017). The infrared spectra of 1266 cm−1, 1227 cm−1 are G ring and acyloxy CO—O stretching vibration, C—C and C—O stretching vibration (Zhang et al., 2009; Shamsudin et al., 2017). The infrared spectra of 1126 cm−1 and 1033 cm−1 are C—H aromatic in-plane bending vibrations (Ricca et al., 2011).
FT-IR comparison spectra of Pterocarpus cambodianus Pierre powders and three extracts.
3.2 TG analysis
Fig. 2 shows the TG curve of the Pterocarpus cambodianus Pierre. 15–60 °C temperature section in the figure, the quality of Pterocarpus cambodianus Pierre change faster, mainly for water and a small amount of oil evaporation; 60–180 °C temperature section is the continuous endothermic process of wood flour; Pterocarpus cambodianus Pierre powder more violent pyrolysis reaction in the 190–250 °C temperature, making the quality of wood powder decreased faster.
Pterocarpus cambodianus Pierre's TG curve.
3.3 GC–MS analysis
Figs. 3–5 show the total ion chromatograms of the extracts of ethanol, ethanol/benzene and ethanol/methano, respective.
Total ion chromatogram of ethanol extract of Pterocarpus cambodianus Pierre.
Total ion chromatogram of ethanol/benzene extract of Pterocarpus cambodianus Pierre.
Total ion chromatogram of ethanol/methano extract of Pterocarpus cambodianus Pierre.
The chemical constituents of three extracts of Pterocarpus cambodianus Pierre were determined by GC–MS qualitative analysis technique (Jiye et al., 2005; Khan et al., 2017). A total of 25 peaks were isolated by GC–MS gas chromatographic analysis of the ethanol extract of Pterocarpus cambodianus Pierre, and 5 compounds were identified; A total of 49 peaks were isolated by GC–MS gas chromatographic analysis of the Ethanol/benzene extract, and 11 compounds were identified; A total of 47 peaks were isolated by GC–MS gas chromatographic analysis of the Ethanol/methanol extract, and 7 compounds were identified. Tables 1–3 were the results of GC–MS analysis of extracts of ethanol, ethanol/benzene and ethanol/methanol of Pterocarpus cambodianus Pierre.
No.
Retention time (min)
Peak area (%)
Compounds
1
13.385
0.58
4-Methoxybenzene-1,2-diol
2
15.164
0.51
Benzene, 1,2,3-trimethoxy-5-(2-propenyl)-
3
17.092
1.86
.alpha.-Bisabolol
4
20.514
0.82
(1S,2R,4S,7R)-7-((E)-5-Hydroxy-4-methylpent-3-en-1-yl)-1,7-dimethylbicyclo[2.2.1]heptan-2-ol
5
26.937
1.03
cis-Trismethoxyresveratrol
No.
Retention time (min)
Peak area (%)
Compounds
1
11.011
1.05
2(3H)-Furanone, 5-butyldihydro-4-methyl-, cis-
2
12.739
0.57
1,4-Benzenediol, 2-methoxy-
3
13.392
1.05
4-Methoxybenzene-1,2-diol
4
14.776
0.55
3,4-Dihydroxy-5-methoxybenzaldehyde
5
15.164
1.39
Benzene, 1,2,3-trimethoxy-5-(2-propenyl)-
6
17.092
3.89
.alpha.-Bisabolol
7
19.466
1.23
1,2-Benzenedicarboxylic acid, bis(2-methylpropyl) ester
8
20.514
1.62
(1S,2R,4S,7R)-7-((E)-5-Hydroxy-4-methylpent-3-en-1-yl)-1,7-dimethylbicyclo[2.2.1]heptan-2-ol
9
20.63
1.01
1,2-Benzenedicarboxylic acid, butyl 2-methylpropyl ester
10
20.786
0.9
cis-Z-.alpha.-Bisabolene epoxide
11
26.937
1.69
cis-Trismethoxyresveratrol
12
27.791
2.14
S-Indacene-1,7-dione, 2,3,5,6-tetrahydro-3,3,4,5,5,8-hexamethyl-
No.
Retention time (min)
Peak area (%)
Compounds
1
11.018
0.56
2(3H)-Furanone, 5-butyldihydro-4-methyl-
2
13.398
1.67
4-Methoxybenzene-1,2-diol
3
15.164
0.99
Benzene, 1,2,3-trimethoxy-5-(2-propenyl)-
4
17.092
2.11
.alpha.-Bisabolol
5
27.74
3.55
S-Indacene-1,7-dione, 2,3,5,6-tetrahydro-3,3,4,5,5,8-hexamethyl-
6
28.438
3.67
10,11-Dihydro-10-hydroxy-2,3,6-trimethoxydibenz(b,f)oxepin
7
29.176
1.26
6a,12a-Dihydro-6H-(1,3)dioxolo(5,6)benzofuro(3,2-c)chromen-3-ol
3.4 TDS–GC–MS analysis
There is the total ion chromatogram of the Pterocarpus cambodianus Pierre powder in Fig. 6.
Total ion chromatogram of Pterocarpus cambodianus Pierre powder.
The chemical constituents of Pterocarpus cambodianus Pierre powder were determined by TDS–GC–MS qualitative analysis technique. A total of 61 peaks were isolated by TDS–GC–MS gas chromatographic analysis of Diospyros celebica Bakh powder, and 22 compounds were identified; Table 4 shows the results of TDS–GC–MS analysis of Pterocarpus cambodianus Pierre powder.
No.
Retention time (min)
Peak area (%)
Compounds
1
8.254
1.14
Z-8-Methyl-9-tetradecenoic acid
2
8.796
0.76
Undec-10-ynoic acid, tetradecyl ester
3
9.301
1.31
2,5,5,8a-Tetramethyl-4-methylene-6,7,8,8a-tetrahydro-4H,5H-chromen-4a-yl hydroperoxide
4
10.725
2.65
tert-Hexadecanethiol
5
10.952
8.87
1-Dodecanol, 3,7,11-trimethyl-
6
11.128
9.3
.delta.-Dodecalactone
7
11.292
0.63
1-Dodecanol, 3,7,11-trimethyl-
8
12.25
3.27
tert-Hexadecanethiol
9
12.363
0.86
2-Dodecen-1-yl(−)succinic anhydride
10
12.451
3.34
tert-Hexadecanethiol
11
12.577
8.49
Tetradecane, 2,6,10-trimethyl-
12
12.766
1.23
Undec-10-ynoic acid, tetradecyl ester
13
12.93
9.87
Methyleugenol
14
13.22
1.83
2-Pentanone, 4-(1,3,3-trimethyl-7-oxabicyclo[4.1.0]hept-2-yl)-
15
13.434
4.35
tert-Hexadecanethiol
16
14.556
3.29
Formic acid, 3,7,11-trimethyl-1,6,10-dodecatrien-3-yl ester
17
15.438
100
Benzene, 1,2,3-trimethoxy-5-(2-propenyl)-
18
15.665
4.31
10-Methyl-8-tetradecen-1-ol acetate
19
15.955
1.21
2-Dodecen-1-yl(−)succinic anhydride
20
16.043
0.87
5,6,6-Trimethyl-5-(3-oxobut-1-enyl)-1-oxaspiro[2.5]octan-4-one
21
16.144
4.92
tert-Hexadecanethiol
22
16.384
1.71
2-Dodecen-1-yl(−)succinic anhydride
23
16.522
4.86
1-Heptatriacotanol
24
16.673
1.64
2-Dodecen-1-yl(−)succinic anhydride
25
16.736
1.16
tert-Hexadecanethiol
26
16.837
13.75
Cryptomeridiol
27
17.001
5.56
tert-Hexadecanethiol
28
17.089
2.54
tert-Hexadecanethiol
29
17.253
20.07
.alpha.-Bisabolol
30
17.316
1.56
7-Methyl-Z-tetradecen-1-ol acetate
31
17.581
2.68
1-Heptatriacotanol
32
18.476
2.4
7-Methyl-Z-tetradecen-1-ol acetate
33
19.383
0.68
Phen-1,4-diol, 2,3-dimethyl-5-trifluoromethyl-
34
19.585
14.08
Phthalic acid, 5-methylhex-2-yl butyl ester
35
20.769
2.03
Ethyl 9-hexadecenoate
36
20.996
19.52
cis-Z-.alpha.-Bisabolene epoxide
3.5 PY–GC–MS analysis
The powder of Pterocarpus cambodianus Pierre was analyzed by thermal cracking-gas chromatography-mass spectrometry (CDS5200-trace1310 ISQ). The carrier gas used for high purity helium, the pyrolysis temperature was 500 °C, the heating rate was 20 °C/ms, and the pyrolysis time was 15 s. The pyrolysis product transfer line and the injection valve temperature are set to 300 °C; Column TR-5MS; Capillary column (30 m × 0.25 mm × 0.25 μm); Shunt mode, split ratio of 1:60, shunt rate of 50 mL/min. The temperature of the GC program starts at 40 °C for 2 min, rises to 120 °C at a rate of 5 °C/min, and then rises to 200 C at a rate of 10 °C/min for 15 min. Ion source (EI) temperature of 280 °C, scanning range of 28–500 amu. There is the Relative abundance curve of the Pterocarpus cambodianus Pierre powder in Fig. 7.
Relative abundance curve of the Pterocarpus cambodianus Pierre powder.
The chemical constituents of Pterocarpus cambodianus Pierre powder were determined by PY–GC–MS qualitative analysis technique (Gao et al., 2013; Rahman et al., 2017). A total of 50 peaks were isolated by PY–GC–MS gas chromatographic analysis of Pterocarpus cambodianus Pierre, and 11 compounds were identified; Table 5 shows the results of PY–GC–MS analysis of Pterocarpus cambodianus Pierre powder.
No.
Retention time (min)
Peak area (%)
Compounds
1
10.23
4.17
2(3H)-Furanone, 5-methyl
2
11.42
3.05
4-Cyclopentene-1,3-dione
3
14.52
23.03
2-Furancarboxaldehyde, 5-methyl-
4
18.83
2.52
Pentanoic acid, 4-oxo-
5
19.80
8.30
Phenol, 2-methoxy-
6
21.85
150.89
Levoglucosenone
7
26.96
59.88
1,4:3,6-Dianhydro-à-d-glucopyranose
8
27.47
25.41
5-Hydroxymethylfurfural
9
33.09
23.93
Phenol, 2,6-dimethoxy-
10
37.01
13.31
Phenol, 2-methoxy-4-propyl-
11
38.53
8.41
2-Propanone, 1-(4-hydroxy-3-methoxyphenyl)-
3.6 Functional analysis
Pterocarpus and Pterocarpus products have a certain human health function. The PY–GC–MS, TDS–GC–MS and GC–MS techniques were used to qualitatively analyze the Pterocarpus cambodianus Pierre, and the related compounds were obtained. By reviewing the relevant literature and reports, we have obtained the proven, human health function composition. Benzene, 1,2,3-trimethoxy-5-(2-propenyl)- has antioxidant, anti-inflammatory, anti-thrombotic and hypolipidemic functions (Ghafar et al., 2017). .alpha.-Bisabolol can be used to treat leishmaniasis caused by Lactobacillus infants (Moralesyuste et al., 2009; Hassan et al., 2017). 6a, 12a-Dihydro-6H-(1,3) dioxolo (5,6) benzofuro (3,2-c) chromen-3-ol has anti-angiogenic activity (Mathi et al., 2016; Razali and Said, 2017). .delta.-Dodecalactone can be used as a biological preservative and flavoring agent. It exhibits strong antifungal activity against Aspergillus fumigatus, Shichangpu, Ochrathecalomyces, Aspergillus nidulans and Penicillium, and it can produce pleasant sensory characteristics (Yang et al., 2011; Halim et al., 2017). 1-Heptatriacotanol has anti-hypercholesterolemic effects (Baskaran et al., 2015). Cryptomeridiol is a natural product of anti-Alzheimer's disease and antispasmodic nature, and has a significant medicinal value (Tebbaa, 2011). 7-Methyl-Z-tetradecen-1-ol acetate has the effect of heat and heat cough (Hu-Baiyila, 2011). 2-Furancarboxaldehyde, 5-methyl- has a high antimicrobial activity against NCIM 2501 and NCIM 5021 (Jadhav et al., 2010).
4 Conclusions
GC–MS analysis, a total of 25 peaks were isolated by GC–MS gas chromatographic analysis of the ethanol extract of Pterocarpus cambodianus Pierre, and 5 compounds were identified; a total of 49 peaks were isolated by GC–MS gas chromatographic analysis of ethanol/benzene extract, and 11 were identified; a total of 47 peaks were isolated by GC–MS gas chromatographic analysis of ethanol/methanol extract, and 7 compounds were identified.
TDS–GC–MS analysis, a total of 61 peaks were isolated by TDS–GC–MS gas chromatographic analysis of Pterocarpus cambodianus Pierre powder, and 22 compounds were identified.
PY–GC–MS analysis, a total of 50 peaks were isolated by PY–GC–MS gas chromatographic analysis of Pterocarpus cambodianus Pierre powder, and 11 compounds were identified.
Through access to the literature and related reports, we clear the Pterocarpus cambodianus Pierre contains human health ingredients and functions. 6a, 12a-Dihydro-6H-(1,3) dioxolo (5,6) benzofuro (3,2-c) chromen-3-ol has anti-angiogenic activity. 1-Heptatriacotanol has anti-hypercholesterolemic effects. Cryptomeridiol is a natural product of anti-Alzheimer's disease and antispasmodic nature, and has a significant medicinal value. 7-Methyl-Z-tetradecen-1-ol acetate has the effect of heat and heat cough. 2-Furancarboxaldehyde, 5-methyl- has a high antimicrobial activity against NCIM 2501 and NCIM 5021.
Acknowledgments
This research was supported by the Planned Science and Technology Project of Hunan Province, China (No. 2016SK2089; No. 2016RS2011), Major scientific and technological achievements transformation projects of strategic emerging industries in Hunan Province (2016GK4045), Academician reserve personnel training plan of lift engineering technical personnel of Hunan Science and Technology Association (2017TJ-Y10).
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