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Molecules and functions of rosewood: Pterocarpus santalinus
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Received: ,
Accepted: ,
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
People raise redwood, and mahogany will last a lifetime. In China, there have always been the sayings of “sleeping Pterocarpus indicus Willd. and sitting on Dalbergia cochinchinensi”. Among them, the health of mahogany furniture is rarely scientifically and systematically elaborated. Therefore, the active ingredients in the Pterocarpus santalinus extract were analyzed in detail by using advanced detection techniques, and it was found that 54 active ingredients were detected in the Pterocarpus santalinus extract. Mainly include alkanes, phenols, alcohols, terpenes (alkenes), and acids. In the Pterocarpus santalinus extract, the majority components of Pterocarpus santalinus are healthy and abundant; the main representative of the active ingredient were .alpha.-Bisabolol, Squalene, cedrol, Propanoic acid, 2-methyl-, 3-hydroxy-2,2,4-trimethylpentyl ester, P-Cresol, (-) - Spathulenol and Heptacosane. It also has potential application prospects in the fields of bio-energy, bio-medicine, cosmetics, skin care products, and spices. The study of the chemical composition of Pterocarpus santalinus provides a scientific basis for the development and utilization of the plant.
Keywords
Pterocarpus santalinus
Chemical composition
Extract
Redwood
GC–MS
1 Introduction
Pterocarpus santalinus belongs to the butterfly-shaped red sandalwood flowers, classified as rosewood mahogany, are medium arbor, found mainly in India, has deep and white stripes, and is slightly fragrant. Because of the pterocarpin, it is soluble in alcohol and ether; wood chips in the alcohol were orange, and the fingers dipped in alcohol or water and wood friction was red (Anuradha and Pullaiah, 1999; Manjunatha, 2006).
The chemical composition of wood is complex and diverse—mainly consisting of carbohydrates, phenols, terpenes, fatty acids, etc.—which can also be divided into fiber hemicellulose, lignin, and extract (Esteves et al., 2008). The chemical composition of different woods is varied, but the chemical composition of the same wood is usually more fixed. This chemical composition affects the physical mechanics, natural durability, color, smell, and taste of the wood, as well as its processing and utilization (Esteves and Pereira, 2009; Mohareb et al., 2012). Wood moisture absorption is mainly due to the presence of hydrophilic and free hydroxyl groups on the cellulose (Endo et al., 2016; Peng et al., 2018). Lignin is a kind of complex aromatic substance; the chemical structure of lignin and wood species has an important impact on the color of the wood (Huang et al., 2016; Wang et al., 2015). Experimental results from Zhang Shuangyan et al. (2013) show that the content of lignin and a single fiber elastic modulus positively correlated with a higher cellulose content and fiber tensile strength. Hemicellulose and lignin as a bonding material and hard solid material give the wood elasticity and compressive strength (Esteves et al., 2008; Fidêncio, 2011; Shen et al., 2017). In addition to the three elements, wood also contains certain types and quantities of extracts, such as volatile oils, resins, and other phenolic compounds (Aydemir et al., 2011; Tumen et al., 2010). The wood has a different color, which is associated with the cell cavity, whether the cell wall is filled or deposited extract. Some species contain natural pigments, such as flavonoids and ketones, etc.; the heartwood was red because the redwood heartwood contains redwood pigment, while the mahogany contains magenta hematoxylin pigment, so that redwood was red. Balaban (2004) studied the phenolic compounds of sapwood and heartwood by GC–MS. Arias et al. (2012) also detected and analyzed lignin heat transfer decomposition of the material by GC–MS of pyrolysis pine at different high temperatures.
In order to scientifically and systematically explain the mahogany in depth, so that people can have a clearer understanding of the way of redwood health; at the same time, studying the chemical composition of wood can provide a basis for the processing and utilization of wood. Therefore, sandalwood was used as the research object, and the organic solvent extracts were analyzed by advanced detection methods (such as FT-IR, TG, GC–MS, PY-GC–MS, and TDS-GC–MS). The molecular composition of sandalwood extract was deeply analyzed through comparative analysis, and the prospect of resource utilization was prospected (Mi et al., 2019).
2 Material and methods
Extraction methods: Samples were crushed into 40–60 mesh powder by a crusher. Then, dry 10%, take 10 g (accuracy: 0.1 mg) of dried Pterocarpus santalinu sample, put into distillation bottles, add 300 mL (accuracy: 1 mL) of ethanol, ethanol/benzene (1:1), and methanol/ethanol (1:1) solvent was used to extract, respectively. The extraction were named B1, B2, and B3 samples. The mixture of reagents was extracted for 5 h at 85 °C, then the solid powder was named B1-1, B2-2, and B3-3 samples, respectively.
To determine the functional groups and chemical bonding present in the extract of the Pterocarpus santalinu, FT-IR analysis was conducted with a FT-IR spectrophotometer (Thermo Fisher Scientific iS100) at 4000–400 cm−1. FT-IR test sample was prepared by mixing the sample with KBr in a ratio of 1:100. The instrument records infrared molecular absorption, infrared spectrum acquisition, spectral smoothing and baseline correction. Infrared spectroscopy usually takes wave (σ) as abscissa to indicate the position of absorption peak, and vertical axis transmittance to indicate absorption intensity (Jiang et al., 2017; Peng et al., 2014; Xue et al., 2014).
The chemical components present in the samples were determined by a GC–MS (Agilent 7890B-5977A). The column used was elastic quartz capillary column named HP-5MS (30 m × 250 μm × 0.25 μm). High purity helium (1 mL/min) was used as the carrier gas and the split ratio was 2:1. The GC oven was started at 50 °C, and heated to 250 °C (ramping rate = 8 °C/min), and then further heated up to 280 °C (ramping rate = 5 °C/min). For the MS, compounds in the mass range of 30–600 amu were detected. Meanwhile, the ionization voltage and current were 70 eV and 150 μA EI, respectively. The quadrupole and the ion source temperature were set at 150 °C and 230 °C, respectively.
Fast pyrolysis of Pterocarpus santalinu were performed and analyzed via thermogravimetry (TG), and pyrolysis/GC–MS (Py/GC–MS). The performance of the four samples were investigated and compared. The thermogravimetric analyzer (TGA) is used to study the thermal stability and composition of materials. For TG analysis, 4–7 mg of the samples were analyzed using TGA Q50 V20.8 Build 34. Instruments to determine the thermal decomposition of the samples. The sample was from 30 °C to 250 °C under nitrogen flow (60 mL/min) with two different ramping rates of 5 °C/min. Py/GC–MS (CDS5200-trace1310 ISQ) equipped with TR-5MS capillary column (30 m × 0.25 mm × 0.25 μm) was used during Py/GC–MS test. The sample was from 30 °C to 500 °C (ramping rate = 20 °C/ms) under inert helium flow (50 mL/min) for 15 s, before the product sample was subjected to GC. The GC was operated under split mode with split ratio of 60:1. The GC oven was started at 40 °C (holding time = 2 min), heated to 120 °C (ramping rate = 5 °C/min), and then further increased to 200 °C (ramping rate = 10 °C/min, holding time = 15 min. For the MS, the ion source [electron ionization (EI)] temperature and scanning range were set at 280 °C and 28–500 amu. TD/GC–MS: First, the sample was from 30 °C to 100 °C (ramping rate = 10 °C/min, retained for 5 min), then 100 °C–200 °C (ramping rate = 10 °C/min, retained for 0 min) (Peng et al., 2012).
3 Results and discussion
3.1 Analysis of FT-IR
The infrared spectrum of Pterocarpus santalinus was analyzed. Fig. 1 shows the infrared contrast spectra of the Pterocarpus santalinus and the three extracts. The absorption peak in infrared spectrum is the stretching vibration of free hydroxyl above 3400 cm−1. The broad peak is an intermolecular association absorption peak near 3400 cm−1. The absorption peak is the stretching vibration of the saturated C–H bond at 3000–2750 cm−1. The absorption peak at 1800–1580 cm−1 was attributed to the C=O stretching vibration. The absorption peak at 1480–1300 cm−1 is mostly CH2 and CH3 bending vibration absorption. The absorption peaks near 1450 cm−1 and 1350 cm−1 are CH2 stretching vibration and CH3 stretching vibration, respectively. The absorption peak is mainly caused by C–C stretching vibration, C–O stretching vibration, and C–H bending vibration at 1300–650 cm−1 (Huang et al., 2008; Müller et al., 2009; Yao et al., 2010). The absorption peaks of cellulose (2948 cm−1), hemicellulose (1730 cm−1), and lignin (1739 cm−1, 1611 cm−1, 1501 cm−1, and 812 cm−1) in the chemical composition of sandalwood were slightly weakened, indicating that part of it underwent hydrolysis (Honyet al., 2000; Wen et al., 2014). From the FTIR analysis, it was determined that the main chemical components of Pterocarpus santalinus extracts are phenols, alcohols, ethers, fatty acids, ketones, polysaccharides, and fatty acids (Fig. 2).
FT-IR spectra of samples B0, B1, B2, and B3.
FT-IR spectra of samples B0, B1-1, B2-2, and B3-3.
3.2 Analysis of TGA and DTG
Fig. 3, presents the thermogravimetric (TG) and derivative thermogravimetric (DTG) curves. From the figure, the changes in mass loss rate of the samples can be elucidated. T1wt%, T5wt% and T10wt% for weight loss of 1 wt%, 5 wt% and 10 wt%, respectively (Mathi et al., 2016). T1wt%, T5wt% and T10wt% are 34 °C, 75 °C and 224 °C, respectively. TGA is divided into two stages: water evaporates mainly at low temperature, while the other is the high temperature phase of coke through aerobic combustion. Between 50 and 250 °C, Pterocarpus santalinus thermo-gravimetric is only approximately 13% and thermal weightlessness is less, this phenomenon shows that Pterocarpus santalinus thermal stability is better. Moreover, the TGA and DTG tests showed that at 250 °C below, only a small amount of hemicellulose, cellulose and lignin pyrolysis was found in Pterocarpus santalinus, showing good thermal stability. Overall, Pterocarpus santalinus has better thermal stability.
TGA and DTG thermal curves of Pterocarpus santalinus.
3.3 Analysis of GC–MS
The total ion chromatograms and component distribution obtained from GC–MS analysis of the AB wood waste in the form of extracts are shown in Figs. 4–6.
Total ion chromatograms of Pterocarpus santalinus which were extracted by ethanol.
Total ion chromatograms of Pterocarpus santalinus which were extracted by ethanol/benzene (1:2).
Total ion chromatograms of Pterocarpus santalinus which were extracted by ethanol/benzene (1:1).
There is a total of 56 chemical components being identified from the 76 peaks generated by GC–MS analysis of B1 extracts. The results show that the content of more substances are as follows: 2-Naphthalenemethanol, 2-Naphthalenemethanol, decahydro-.alpha.,.alpha.,4a-trimethyl-8-methylene-, [2R-(2.alpha.,4a.alpha.,8a.beta.)]- (23.7%), .alpha.-Bisabolol (11.32%), Alloaromadendrene oxide-(1) (5.51%), 2-Propen-1-ol, 3-(2,6,6-trimethyl-1-cyclohexen-1-yl)- (13.44%), Estra-1,3,5(10)-trien-17.beta.-ol (5.3%), cis-Z-.alpha.-Bisabolene epoxide (6.78%), cis-Z-.alpha.-Bisabolene epoxide (45.01%), 1-Heptatriacotanol (6.08%), 9,12-Octadecadienoic acid (Z,Z)- (5.08%), Oleic Acid (5.36%), 9-Octadecenamide, (Z)- (6.81%), Heptacosane (10.67%), and Squalene (10.5%). The results show that 56 chemical components being identified from the 76 peaks generated by GC–MS analysis of B2 extracts. The show that the content of more substances are as follows: .alpha.-Bisabolol (14.18%), Alloaromadendrene oxide-(1) (6.81%), (1R,4aR,7R,8aR)-7-(2-Hydroxypropan-2-yl)-1,4a-dimethyldecahydronaphthalen-1-ol (6.01%), Isospathulenol (11.23%), 2-Propen-1-ol, 3-(2,6,6-trimethyl-1-cyclohexen-1-yl)- (15.04%), 2,4-Dimethyl-5,6-dimethoxy-8-aminoquinoline (10.45%), Isoaromadendrene epoxide (8.81%), cis-Z-.alpha.-Bisabolene epoxide (50.02%), 2H-1-benzopyran-2-one, and 7-hydroxy-3-(4-methoxyphenyl)- (21.69%). The results show that 57 chemical constituents were identified in B3. The content of more substances are as follows: 2-Naphthalenemethanol, 1,2,3,4,4a,5,6,7-octahydro-.alpha.,.alpha.,4a,8-tetramethyl-, (2R-cis)- (7.18%), .alpha.-Bisabolol (14.71%), Alloaromadendrene oxide-(1) (7.3%), (1R,4aR,7R,8aR)-7-(2-Hydroxypropan-2-yl)-1,4a-dimethyldecahydronaphthalen-1-ol (6.62%), (-)-Spathulenol (100%), Isospathulenol (10.53%), 2-Propen-1-ol, 3-(2,6,6-trimethyl-1-cyclohexen-1-yl)- (15.54%), 2,4-Dimethyl-5,6-dimethoxy-8-aminoquinoline (9.02%), cis-Z-.alpha.-Bisabolene epoxide (8.15%), Ledene oxide-(I) (22.5%), and 10,11-Dihydro-10-hydroxy-2,3,6-trimethoxydibenz(b,f)oxepin (5.23%) (Fig. 7).
Total ion chromatograms of Pterocarpus santalinus by TDS-GC–MS.
3.4 Analysis of TDS-GC–MS
According to the results of TDS-GC–MS analysis, 48 chemical constituents were identified in 58 peaks of Pterocarpus santalinus volatiles. The results show that the components are: Naphthalene, 1,2,4a,5,8,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-,(1.alpha.,4a.beta.,8a.alpha.)-(.+/-.)- (18.26%), 2-((2R,4aR,8aS)-4a-Methyl-8-methylenedecahydronaphthalen-2-yl)prop-2-en-1-ol (11.48%), Benzene, 1,2,3-trimethoxy-5-(2-propenyl)- (40.97%), cis-Z-.alpha.-Bisabolene epoxide (11.25%), 2-Naphthalenemethanol, .alpha.-Bisabolol (60.04%), 6-Isopropenyl-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-ol (27.31%), 2-((2R,4aR,8aS)-4a-Methyl-8-methylenedecahydronaphthalen-2-yl)prop-2-en-1-ol (12.42%), 6-Isopropenyl-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-ol (24.85%), and 4-(2,2,6-Trimethyl-7-oxabicyclo[4.1.0]hept-4-en-1-yl)pent-3-en-2-one (11.43%) (Fig. 8).
Total ion chromatograms of Pterocarpus santalinus by Py-GC–MS.
3.5 Analysis of Py-GC–MS
The results of Py-GC–MS show that 50 compounds were identified in Pterocarpus santalinus, and the peak area accounted for 47.54% of the total peak area, of which the content was higher: Carbamic acid, monoammonium salt (5.14%), Acetone (3.52%), Glycolaldehyde dimer (5.03%), Acetic acid (3.92%), Phenol, 2-methoxy- (5.02%), Creosol (5.35%), m-Guaiacol (5.77%), 2-Methoxy-4-vinylphenol (5.87%), Phenol, 2,6-dimethoxy- (3.65%), and trans-Isoeugenol (3.76%).
3.6 Analysis of function
Pterocarpus santalinus is a high-end, expensive furniture material. Pterocarpus santalinus and Pterocarpus santalinus products have a certain human health function. The Py-GC–MS, TDS-GC–MS, and GC–MS techniques were used to analyze the Pterocarpus santalinus, obtaining the related compounds. Through literature analysis found that the .alpha.-Bisabolol has anti-inflammatory, antispasmodic, and antiulcer effects, though it also has increased skin defense ability and reduce skin tension. Furthermore, the .alpha.-Bisabolol can efficiently inhibit the human dendritic cell pro-inflammatory activity (Marongiu et al., 2014). Squalene can inhibit the body to absorb cholesterol, which has the function of lowering cholesterol (Smeriglio et al., 2016).
Moreover, the cedrol is a sesquiterpene compound, which is an important component of wood flavor and sandalwood. Not only that, but it can also be used as a disinfectant, which has the effect of inhibiting human lung cancer cells (Dayawansa et al., 2003). To continue, (-) - Spathulenol has an immune effect (Ziaei et al., 2011). Heptacosane is key in banana leaf volatile oil. Pterocarpus santalinus mainly contains unsaturated fatty acids, phytosterols, and polyphenols, which can be used as an antioxidant, anti-aging, lowering blood pressure, improving memory, and other effects. In general, most of the ingredients of sandalwood are healthy and rich, indicating that it contains natural healthy ingredients in terms of health and is a treasure of human health care.
4 Conclusion
In the TG, FTIR, TDS-GC–MS, Py-GC–MS, and GC–MS test, 117 active ingredients were identified in Pterocarpus santalinus extract. The main chemical components of Pterocarpus santalinus extracts are phenols, alcohols, ethers, ketones, polysaccharides and fatty acids, some of which can be used in high-end perfumes, cosmetics, food and biomedical products. It can be observed from the above studies that the effective components in Pterocarpus santalinus are antibacterial, antitumor, and insecticidal activity, of which the .alpha.-Bisabolol has anti-inflammatory, antispasmodic, and antiulcer effects, while also having increased skin defense ability and reduced skin tension. Squalene can inhibit the body to absorb cholesterol, ultimately lowering cholesterol. The cedrol is a sesquiterpene compound, which is an important component of wood flavor and sandalwood. It can also be used as a disinfectant, which has the effect of inhibiting human lung cancer cells, indicating that it contains natural healthy ingredients in terms of health and is a treasure of human health care.
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). Yanqiang Wei’s contribution as same as the first author, he was also co-first author.
Declaration of Competing Interest
The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
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