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New insights in the chemical composition of benzoin balsams
... 23 000 ha. 4 Siam benzoin consists mainly of coniferyl benzoate, benzoic acid, and triterpenoids including 6β-and 19α-hydroxylated oleanolic acid derivatives such as sumaresinolic acid and siaresinolic acid, 5−8 while Sumatra benzoin contains pinoresinol, sumaresinolic acid, and large amounts of cinnamic acid and esters such as p-coumaryl cinnamate and cinnamyl cinnamate. 8 Cinnamic acid esters have been reported to exhibit antibacterial and antifungal activity. 9, 10 We recently found that Sumatra benzoin and its major constituent, p-coumaryl cinnamate, may have a potential to be developed as an agricultural fungicide. ...
... 11 Several phytochemical investigations have been performed on Sumatra benzoin. They include gas chromatography (GC) analysis of volatile constituents, 12,13 the detection and quantification of phenolic constituents by highperformance liquid chromatography with ultraviolet-evaporative light scattering detection (HPLC-UV-ELSD) analysis, 8 the analysis of triterpenoids and benzyl and cinnamyl esters by HPLC coupled with photodiode array detection and fluorimetry (HPLC-PDA-fluorimetry), 14 and the analysis of free and ester bound benzoic and cinnamic acids by GC−MS and HPLC−frit-fast atom bombardment−MS (HPLC−frit FAB−MS). 15 Sumatra benzoin was also included in a large study comparing the chemical profiles of various balsams. ...
... A total of 13 compounds ( Figure 2) corresponding to the major peaks detected by the different detectors were identified after preparative isolation by ESIMS and NMR analysis (Tables S1−S3). They included compounds which had been previously identified in Sumatra benzoin such as vanillin (1), 13 benzoic acid (2), 13 pinoresinol (3), 16 cinnamic acid (4), 13 p-coumaryl cinnamate (5), 8 coniferyl cinnamate (6), 8 benzyl cinnamate (7), 8 cinnamyl benzoate (8), 8 cinnamyl cinnamate (9), 8 sumaresinolic acid (11), 7,8 and oleanolic acid (13), 7,19 as well as 6β-hydroxy-3oxo-12-oleanen-28-oic acid (12), previously reported in Siam benzoin. 7 In addition, a new secondary metabolite 10 was isolated and its structure established. ...
Sumatra benzoin, a resin produced by Styrax benzoin and Styrax paralleloneurum, is used as an aromatic agent and may have the potential to be developed as a new agricultural fungicide. In this context, we performed a comprehensive metabolite profiling of a commercial grade A resin by high-performance liquid chromatography coupled with photodiode array detection, evaporative light scattering detection, and mass spectrometry (HPLC-PDA-ELSD-MS) analysis in combination with 1H NMR. Thirteen compounds including a new cinnamic acid ester containing two p-coumaroyl residues were identified after preparative isolation. These compounds accounted for an estimated 90% of the crude resin according to 1H NMR analysis. The two major constituents, p-coumaryl cinnamate (5) and sumaresinolic acid (11), were quantified by HPLC analysis. In a next step, the chemical profiles and the content in p-coumaryl cinnamate were compared in a large set of resin samples of different quality grades that were obtained from various commercial suppliers in Sumatra. The qualitative profiles of the samples were very similar, but significant quantitative differences were observed between different quality grades and origins of the samples for the relative contents.
... There are 15 pentacyclic triterpenoids (Figure 3), which are all oleanane-type triterpenoids, as well as only one special sesquiterpenoid discovered in benzoin [4,24,[26][27][28][29]. The bioactivities of their cytotoxic and differentiation-inducing effects demonstrate their potential for anticancer treatments [29,30]. ...
... There are eight lignans isolated from benzoin ( Figure 2), including benzofuran lignans, tetrahydrofuranoid lignans, neolignane and oxyneolignan [4,6,[23][24][25]. ...
... There are 15 pentacyclic triterpenoids (Figure 3), which are all oleanane-type triterpenoids, as well as only one special sesquiterpenoid discovered in benzoin [4,24,[26][27][28]30]. The bioactivities of their cytotoxic and differentiation-inducing effects demonstrate their potential for anticancer treatments [29,30]. ...
Benzoin is a pathologic exudation produced by plants of the family Styrax. It is secreted by traumatic resin ducts after injury, which are derived from parenchymal cells in secondary xylem by schizolysigeny. Some 63 chemical constituents have been isolated and identified from this resin, including balsamic acid esters, lignans and terpenoids. It has a long history of applications, including as incense along with olibanum, a flavor enhancer in the food industry, materials in the daily chemistry industry as well as therapeutic uses. Up to now, high-performance liquid chromatography (HPLC) and gas chromatography mass spectrometry (GC-MS) have been widely used in qualitative and quantitative analysis of benzoin. Other technologies, including near-infrared reflectance spectroscopy (NIR), proton transfer reaction time-of-flight mass spectrometry (PTR-ToF-MS) and Fourier-transform infrared spectroscopy (FT-IR), have also been used to distinguish different resins. Herein, this paper provides a comprehensive overview of the production process, phytochemistry, traditional uses and quality control of benzoin and looks to the future for promoting its further research and applications.
... Cinnamic acid esters are found in benzoin balsams [1]. Cinnamic acid esters show biological activities such as antifungal [2], antidiabetic [3], antituberculosis, antimalarial [4], antioxidant [5], antiprotozoal [6], anti-inflammatory [7], and antiproliferative activities [8]. ...
... The solvent was removed under reduced pressure, and the crude product was purified using "dry-column" flash column chromatography with ethyl acetate/n-hexane (1/25) eluant to afford 4-methoxyphenethyl (E)-3-(o-tolyl)acrylate (1) as a yellowish liquid (0.22 g, 51%). 1 ...
... The reaction was conducted in triplicate. The percentage of α-glucosidase inhibition can be calculated by Equation (1), and the IC 50 value was obtained from the linear regression analysis by several test concentrations. ...
4-Methoxyphenethyl (E)-3-(o-tolyl)acrylate (1) was obtained in a good yield by the reaction of 2-methylcinnamic acid, 4-methoxyphenethyl alcohol, 2-methyl-6-nitrobenzoic anhydride, 4-dimethylaminopyridine, and triethylamine at room temperature for 40 min. The structure of 4-methoxyphenethyl (E)-3-(o-tolyl)acrylate (1) was established by FTIR, NMR, and the high resolution of mass spectroscopies. 4-Methoxyphenethyl (E)-3-(o-tolyl)acrylate (1) showed higher α-glucosidase inhibition activity than standard drug acarbose. The molecular docking study exhibited that the title compound 1 had a good affinity for α-glucosidase (PDB ID: 3W37) and formed some interactions with the α-glucosidase active site residue.
... The growing attention to styrax resin refers to various aromatic compounds content. Some volatile compounds are presented, with benzyl benzoate (76.1%), cinnamic acid (3.5%) and benzyl cinnamate (3.3%) as the major constituents [3,4]. These pharmacological contents have been used for muscle pain, anxiety, nervous disorders, treatment of skin diseases, arthritis, wounds, etc. [4,5]. ...
... Some volatile compounds are presented, with benzyl benzoate (76.1%), cinnamic acid (3.5%) and benzyl cinnamate (3.3%) as the major constituents [3,4]. These pharmacological contents have been used for muscle pain, anxiety, nervous disorders, treatment of skin diseases, arthritis, wounds, etc. [4,5]. ...
... In another essential oil extraction, such as lavender, hydrosol or distilled water have a very pleasant aroma with commercial applications [7]. This aromatic water is applied in cosmetics, fragrances, food flavoring, aromatherapy, and traditional therapy [3][4][5]7,8]. Hydrosols have also some biological activities with high potential for global economic products [8]. ...
Styrax resins or benzoin contain aromatic compounds that applied for medicine, perfumery, food ingredients and others. The resins harvested from Styrax trees were distilled to produce essential oils and hydrosols. Unfortunately, the distillate water usually discarded when separating the primary oils. The objective of study was to evaluate the hydrosol production derived from steam distillation process using various qualities of styrax resin. The materials used are the first grade and harvesting waste resin collected from community’s forests in Humbang Hasundutan, North Sumatra, Indonesia. Three replicates of both resin quality were analysed for moisture content, then steam distillation applied for essential oils and hydrosols production. The research shows that at termination of distillation, the best quality resins produced approximately 3.18 kg (31.8%) and 2.74 kg (27.4%) hydrosol from the waste resin. The essential oils production from first quality is higher than the lowest, approximately 64 g (yield 0.64%), while residue resins produce 53 g (0.53%). It is estimated 7.7% of water in hydrosol derive from waste resin assuming all water contained evaporates and condenses to hydrosol. Considering harvesting residues disposed and unutilized, distillation of lowest quality resin for hydrosol production proposes an alternative strategy for optimizing the forest resources utilization.
... Unfortunately, almost all cosmetic and healthy products use synthetic fragrances and ingredient, while limited cosmetic's manufacturers use essential oils to produce high quality products. Various studies have shown that incense resin contains phyto-chemical content which is important both as antiviral, anti-septic with a relaxing aroma [5][6][7][8][9]. Incense oil can also be used for skin beauty. ...
... Despite limited influence in saponication effectiveness, the addition of styrax essential oil enhanced the soap aroma. This is due to the essential oil contains various volatile compounds which have a fragrant aroma [5][6][7]. Chemical composition of volatile extracts of styrax essential oil along with their aroma is shown in Table 4. ...
... For aromatherapy application, styrax essential oil aroma has a relaxing effect [6,7,17,18]. In topical application, styrax oil can relieve inflammation, insect bites, acne, itching, irritation, rashes, sprains, and muscular aches and pains [5][6][7]. ...
Styrax resin is the main non-timber forest product from North Sumatra, Indonesia. Unfortunately, the precious resin known as benzoin still have not been developed into various domestic and innovative organic personal care products. The objective of study is to initiate the distilled styrax resins utilization into personal care products in form of organic and healthy washing hand soaps. Research was carried out by distilling styrax resin, formulating and producing soaps, and assessing the products acceptance. Product application tests were applied including soap properties (hardness, cleansing, conditioning, bubbly and creamy), feeling and preference tests (sensibility, moisturizing, smoothness, scent). Forty respondents were surveyed, which 35 individuals (87.5%) expressed their pleasure utilizing the soaps, related to good consistency and cleaning performance, smoothness, moisturizing, as well as easily rinsed from hands after washing with a pleasant long lasting aroma. The phytochemical content contained is also reveals soap potential application to reducing anxiety and increase immune system. The results showed the idea about processing styrax resin into organic and healthy personal care products is highly feasible for replication in wide-scale applications. Regarding the products contains organic ingredient, it is considered better, healthier and support the local economy development.
... Although Hu et al. (2019) also identified eight lignans from S. tonkinensis leaves, the majority of S. tonkinensis study has been concentrated on the plant's resin. Benzoin resin, sometimes called Siam benzoin balsam (Burger et al., 2016), is the resin of this plant and has been used for thousands of years in traditional Chinese medicine (Wang et al., 2016) as a medication for analgesia and blood circulation. As of right now, benzoin resin has yielded 11 triterpenes (Wang et al., 2015;Wang et al., 2006a;Zhen-feng, 2012), 11 phenylpropanoids (Burger et al., 2016;Huang et al., 2009;Wang et al., 2006b;Zhenfeng, 2012), and a few aromatics (Wang et al., 2020;Wang et al., 2012). ...
... Benzoin resin, sometimes called Siam benzoin balsam (Burger et al., 2016), is the resin of this plant and has been used for thousands of years in traditional Chinese medicine (Wang et al., 2016) as a medication for analgesia and blood circulation. As of right now, benzoin resin has yielded 11 triterpenes (Wang et al., 2015;Wang et al., 2006a;Zhen-feng, 2012), 11 phenylpropanoids (Burger et al., 2016;Huang et al., 2009;Wang et al., 2006b;Zhenfeng, 2012), and a few aromatics (Wang et al., 2020;Wang et al., 2012). ...
Among the genera in this family, Styrax is unique in that it yields benzoin resin, a resinous substance. Usually, when sharp items lacerate the bark, this resin is secreted. Because of its fragrant qualities, it has been used for centuries in cosmetics and fragrances all over the world. Additionally, Styrax species have long been employed in herbal remedies for a variety of ailments. The antibacterial characteristics of Styrax tonkinensis essential oil (STEO) were the focus of this study. The antimicrobial activity was compared to bacteria, both Gram-positive (G ⁺ ) and Gram-negative (G ⁻ ), using inhibition zones in agar media, minimum inhibitory concentration (MIC) bioassays and in vapour phase on fruits and vegetables model. The findings showed that STEO was very successful in inhibiting bacteria that were G ⁺ ( Bacillus sutbtilis subsp. Spizizenii CCM 1999, Bacillus thuringiensis CCM 19, and Priestia ( Bacillus ) megaterium CCM 2007) as well as G- ( Citrobacter koseri CCM 2535, Enterobacter aerogenes CCM 2531, Escherichia coli CCM 3954). The range of maximal inhibition zones and MIC values was determined to be 4.67 to 8.33 mm and 3.49 to 7.71 mg.mL ⁻¹ , respectively. Furthermore, B. thiriangensis , P. megaterium , and E. coli were all susceptible to the antimicrobial effects of the (STEO) on the fruit and vegetable model. According to research findings, STEO is a valuable source of organic chemicals that have the potential to be innovative antibacterial agents against microbes.
... Mass concentration in ppm except for N, K, Mg and Ca in % (Breulmann et al., 1998) Benzoin is an Asian phenolic resin which is exuded by tree tapping from Styrax of the Styracaceae family with a major production in Southeast Asia (Sumatra, Java, Laos, Thailand) (Table 48). There are two main sources: i-Siam styrax which is from Styrax tonkinensis and Styrax benzoides, and ii-Sumatra styrax from Styrax benzoin and Styrax paralleloneurum (Langenheim, 2003;Burger et al., 2016). Benzoin was introduced into alcohol-based varnishes in the mid-16 th c. in Europe (Merrifield, 1967). ...
... Benzoin comprises benzoic and cinnamic acids, classified as carboxylic acids and deriving from the benzene and styrene groups, as well as their ester such as coniferyl benzoate and some triterpenes (Mills and White, 1987;Langenheim, 2003;Burger et al., 2016) (Figure 14). Figure 14. Benzoic and cinnamic acids, the most abundant molecules in benzoin resin (Mills and White, 1987). ...
The PhD study presented here explores the feasibility and the limits of adapting two advanced techniques currently used in archaeometry: 14C geochronology (MICADAS) and isotope geochemistry (MC-ICP-MS NEPTUNE), to the issues of the instrumentarium of the modern period kept in museum collections. The research focused on linseed oil/colophony varnishes; the material corpus was extended to varnishes of pieces of furniture and horse-drawn carriages mainly from the early 18th c. and also includes early gut strings as a testimony of the material history of uses. The 14C geochronology study led to the development of sampling protocols and chemical treatments for analyzing materials according to their nature. The study also provided new insights to deepen our knowledge of the analyzed objects and their uses (impact of restorations, reuse of materials, ingredients, etc.). The Sr isotope study (geographical provenance) was tested on organic binders from the current market. The conservation of the 87Sr/86Sr signature from the bedrocks to the pine resin and colophony (after distillation) was validated for a corpus of pine soil/resin/colophony with a known provenance. The selected colophony provided 87Sr/86Sr measurements consistent with geochemical maps. The state of advancement in the methodological adaptations for both approaches highlights the possibility of overcoming pitfalls such as the sample size or the contamination levels. Three articles were published (Durier et al. 2019, 2021, 2022). This research opens up new perspectives to address the issues of counterfeiting, retouching, maintenance or restoration on musical instruments, and on the provenance study of organic binders for vanishes used in violin making, extended to other heritage objects.
... Flavonoids were mostly identified through LC-MS, and their abundance showed many obvious change trends within clusters I (45), IV (41), VI (33) and VII (37). Fatty acyls were also mainly identified by LC-MS, and had high levels in early stages within clusters I (32), II (26), III (27), V (30), and VIII (46). And, glycerophospholipids (130) and steroids and steroid derivatives (127) were mainly identified by LC-MS. ...
... As bark produces the abundant benzoin used in incense, perfumes and medicines [27], S. tonkinensis has high economic and medicinal value [28,29] with abundant secondary metabolites. Flavonoids, as important plant secondary metabolites, are present in plant fruits, leaves and roots, such as Polygonum minus Huds. ...
Background:
Styrax tonkinensis is an economic tree species with high timber, medicine, oil, and ornamental value. Its seed, containing a particularly high oil content, are widely studied for their biodiesel properties by nutritional components and oil body ultrastructure. However, their comprehensive biochemical compositions have not been studied.
Methods:
During S. tonkinensis kernel development, we collected samples from four time points for metabolite profiling and classification through gas chromatography-mass spectrometry and liquid chromatography-mass spectrometry.
Results:
A total of 187 and 1556 metabolites were obtained, respectively. All of the metabolites were grouped into 19 and 21 classes by their chemical properties and into 8 clusters based on their change trends, respectively. Among all the metabolites, carboxylic acids and derivatives, flavonoids, fatty acyls, glycerophospholipids, organooxygen compounds, prenol lipids, and steroids and steroid derivatives were the main components. Alanine, glutamine, tryptophan, tyrosine and valine were the five most abundant amino acids. Palmitic acid, stearic acid, oleic acid and linoleic acid were the four major free fatty acids. Flavans, flavonoid glycosides and o-methylated flavonoids were the three major flavonoids. The differential metabolites distributions between different time points were identified. A pathway enrichment was performed, which was mainly focused on three groups, amino acids metabolism, carbon flow from sucrose to lipid and secondary metabolites biosynthesis.
Conclusions:
It's the first time to analyze the metabolite fingerprinting for developing S. tonkinensis kernels and identify varied kinds of flavonoids. We performed metabolite profiling, classification and pathway enrichment to assess the comprehensive biochemical compositions. Our results described the change in major metabolites and main metabolic processes during S. tonkinensis kernel development and provided a variety of bases for seed applications as biofuel or medicine.
... While the differences in both are the presence of methyl benzoate (1.5%), benzoate acid (12.5%), and allyl benzoate (1.5%) in Siam benzoin. Whereas in Sumatra benzoin contains benzyl cinnamate (3.3%) and cinnamic acid (3.5%) [3,14]. ...
... These studies generally focus on identifying both aromatic and non-aromatic components that make up the two resins. On the other hand, unfortunately, food and beverage producers have been looking for more economical flavor enhancers, in addition to the high consumer demand for non-synthetic natural flavor-enhancing products [14]. ...
Benzoin absolute essential oil is a high-value oleoresin derived from the dried sap of the Styrax benzoin tree. One type of Styrax benzoin traded in Indonesia is black Sumatran incense. Reflux extraction method with ethanol is used to gain the benzoin absolute essential oil. The purpose of this study is to investigate the antioxidant activity of benzoin absolute essential oil produced using ethanol reflux extraction. Antioxidant test showed that black Sumatran Incense has active antioxidant properties with IC50 value is 90.03; the antioxidant activity shows potential alternative utilization of this essential oil industry, especially those derived from incense resin and its derivatives.
... Benzoic resin is a balsamic resin that is synthesized using different species of tree bark from the genus Styrax. 5,16 Actually, it is an incense, which is commonly used by Indians, Chinese, Japanese, and Russians for ritual and other similar purposes 8 (Figure 1 shows a typical image of a benzoic resin solid pellet). In this paper, we claim that the benzoic resin is a potential solid fuel, which mainly has a gross calorific value (GCV) of 26 004.92 kJ/kg, and for many decades, its potential has not been fully realized. ...
... The origin and chemical composition of this benzoic resin biomass can be explored in the literature. 16 The comparison of benzoic resin to a coal is possible through their chemical compositions, which are similar. A tree bark can be considered as a biomass, whereas a coal is a fossil. ...
... Regarding the hydrocarbons, the main compounds detected were styrene and 3methylpentadecane. Styrene was first identified in storax [46], a resin used in perfumery, and it is responsible for the sweet balsamic characteristic of some plants [47]. Conversely, reports on the odor or incidence of 3-methylpentadecane are scarce, but few studies report its incidence in vegetables [48,49]. ...
Intermediate wheatgrass (IWG) is a promising perennial grain explored for mainstream food applications. This study investigated the effects of different germination temperatures (10, 15, and 20 °C) and durations (2, 4, and 6 days) on IWG’s volatile and fatty acid (FA) profiles. A method using headspace solid-phase microextraction coupled with gas chromatography–mass spectrometry (HS-SPME-GC-MS) was optimized through response surface design to extract the volatile compounds, achieving ideal extraction conditions at 60 °C for 55 min. Multiple headspace extraction (MHE) was used for volatile compound quantification. Fifty-eight compounds were identified and quantified in IWG flour, mainly alcohols, aldehydes, hydrocarbons, terpenes, esters, organic acids, and ketones. The main FAs found were linoleic acid (C18:2), oleic acid (C18:1), palmitic acid (C16:0), and linolenic acid (C18:3). Principal component analysis showed a direct correlation between volatile oxidation products and FA composition. Germination at 15 °C for 6 days led to a reduced presence of aldehydes and alcohols such as nonanal and 1-pentanol. Therefore, optimized germination was successful in reducing the presence of potential off-odor compounds. This study provides valuable insights into the effects of germination on IWG flour, showing a way for its broader use in food applications.
... Current research on benzoin resin and balsam mainly focuses on the analysis of the different volatile and nonvolatile components in various species or different places of origin [4][5][6][7][8], and little information is available about authenticity assessment. Concerning flavor authenticity and traceability, IRMS has been widely used due to the high precision of the method, the requirement for small samples, and the fact that the same technique can be used for almost any type of food or beverage [9][10][11][12][13]. ...
Authenticity assessment of (E)-cinnamic acid, vanillin, and benzoic acid from various origins (n = 26) was performed using gas chromatography-isotope ratio mass spectrometry coupled with combustion and pyrolysis mode (GC-C/P-IRMS). For that reason, the above three compounds (1–3) from synthetic, natural, and Sumatra benzoin balsam (laboratory prepared, adulterated, and commercial) were investigated. The δ13CV-PDB and δ2HV-SMOW values for compounds 1–3 from synthetic samples (S1–S5) ranging from −26.9 to −31.1‰ and 42 to 83‰, respectively, were clearly different from those of authentic samples (N1–N4, L1–L9) varying from −29.8 to −41.6‰ and −19 to −156‰. In adulteration verification testing, for compounds 1 and 3, both δ13CV-PDB and δ2HV-SMOW data of A1 (5.0% added) and A2 (2.5% added) except A3 (0.5% added) fell into the synthetic region, whereas for compound 2, the δ2HV-SMOW data of adulterated samples (A1–A3) fell into the synthetic region, and even the lowest adulterated sample A3 is no exception. With this conclusion, some commercial Sumatra benzoin balsam samples were identified to be adulterated with synthetic 1 (C1, C3, and C5) and synthetic 2 (C3, C4, and C5) but not with synthetic 3. GC-C/P-IRMS allowed clear-cut differentiation of the synthetic and natural origin of 1, 2, and 3 and definite identification of whether a Sumatra benzoin balsam was adulterated or not.
... The flowers of S. tonkinensis are in strings with a light fragrance and can be used as medicine to relieve pain [14]. Its bark is the source of benzoin, which can be used as a flavoring agent and can produce incense, perfume, and medicine [15,16]. Previous research has indicated that the FA concentration in S. tonkinensis seeds is high, and the UFA concentration increases with seed development, while the saturated fatty acid (SFA) concentration decreases [17,18]. ...
Styrax tonkinensis, whose seeds are rich in unsaturated fatty acids (UFAs), is a high oil value tree species, and the seed oil has perfect biodiesel properties. Therefore, the elucidation of the effect of 24-epibrassinolide (EBL) on fatty acid (FA) concentration and the expression of FA biosynthesis-related genes is critical for deeply studying the seed oil in S. tonkinensis. In this study, we aimed to investigate the changing trend of FA concentration and composition and identify candidate genes involved in FA biosynthesis under EBL treatment using transcriptome sequencing and GC-MS. The results showed that 5 μmol/L of EBL (EBL5) boosted the accumulation of FA and had the hugest effect on FA concentration at 70 days after flowering (DAF). A total of 20 FAs were identified; among them, palmitic acid, oleic acid, linoleic acid, and linolenic acid were the main components. In total, 117,904 unigenes were detected, and the average length was 1120 bp. Among them, 1205 unigenes were assigned to ‘lipid translations and metabolism’ in COG categories, while 290 unigenes were assigned to ‘biosynthesis of unsaturated fatty acid’ in KEGG categories. Twelve important genes related to FA biosynthesis were identified, and their expression levels were confirmed by quantitative real-time PCR. KAR, KASIII, and accA, encoding FA biosynthesis-related enzymes, all expressed the highest at 70 DAF, which was coincident with a rapid rise in FA concentration during seed development. FAD2 and FATB conduced to UFA and saturated fatty acids (SFA) accumulation, respectively. EBL5 induced the expression of FA biosynthesis-related genes. The concentration of FA was increased after EBL5 application, and EBL5 also enhanced the enzyme activity by promoting the expression of genes related to FA biosynthesis. Our research could provide a reference for understanding the FA biosynthesis of S. tonkinensis seeds at physiological and molecular levels.
... The flowers of S. tonkinensis are in strings with light fragrance and can be used as medicine to relieve pain (Chen et al. 2019a, b). Its bark is the source of benzoin, which can be used as a flavoring agent and produce incense, perfume and medicine (Burger et al. 2016;Courel et al. 2019). Moreover, S. tonkinensis is a vital oil plant, and previous research has elaborated the changing trend of crude fat (CF) concentration in its seeds at different days after flowering (DAF). ...
Due to the increasing demand for biofuel feedstock production, Styrax tonkinensis, as a woody oilseed tree species, has received much more attention. However, the effects of various plant growth regulators on its seed development haven’t been explored deeply. Here, we applied 24-epibrassinolide (EBL) and methyl jasmonate (MJ) on the whole trees, and the aim of our study was to explore their effects on seed development of S. tonkinensis as well as seed chemical compositions, especially seed lipid metabolism. The results showed that EBL and MJ promoted the seed development, which was reflected in the increase of fresh and dry weight, as well as transverse and longitudinal diameter. The concentration of crude fat (CF) exhibited an ‘increase–decrease-increase’ trend, and the peak appeared at 70 days after flowering. EBL (in concentration of 5 μM, EBL5) and MJ (in concentration of 200 μM, MJ200) had the most significant effect on the accumulation of CF and the CF content in single seed. In addition, the activities of enzymes related to fatty acid (FA) synthesis were also higher under the two treatments. 12 FAs were detected using gas chromatography-mass spectrometry, among which palmitic acid, oleic acid, and linoleic acid were the main components. EBL5, EBL10, and MJ200 favored the accumulation of soluble sugar, especially in the middle and late stages. The starch concentration in seeds was lower, but it significantly increased after the application of EBL5. Furthermore, our results demonstrated that EBL and MJ enhanced SOD and POD activity while decreased MDA content. We highlighted that EBL and MJ promoted seed development of S. tonkinensis, affected seed chemical compositions and contributed to the accumulation of CF and FA.
... It is native to Laos, Vietnam, Cambodia, Thailand, and southern China (Pinyopusarerk, 1994). This species is a deciduous tree with high timber, seed oil, medicine, and ornamental value (Hieu et al., 2011;Xu and Yu, 2015;Burger et al., 2016). It also has great potential as a biofuel due to its excellent fatty acid composition and over 50% oil content in its kernels . ...
As a promising oil species, Styrax tonkinensis has great potential as a biofuel due to an excellent fatty acid composition. However, frequent flooding caused by global warming and the low tolerance of the species to waterlogging largely halted its expansion in waterlogged areas. To explore endogenous hormones and phytohormone-related molecular response mechanism of S. tonkinensis under waterlogging, we determined 1-aminocyclopropane-1-carboxylic acid (ACC) and three phytohormone content (ABA, abscisic acid; SA, salicylic acid; IAA, indole-3-acetic acid) and analyzed the transcriptome of its seedlings under waterlogged condition of 3–5 cm. The sample collecting time was 0, 9, 24, and 72 h, respectively. It was concluded that ACC presented an upward trend, but other plant hormones showed a downward trend from 0 to 72 h under waterlogging stress. A total of 84,601 unigenes were assembled with a total length of 81,389,823 bp through transcriptome analysis. The GO enrichment analysis of total differentially expressed genes (DEGs) revealed that 4,637 DEGs, 8,238 DEGs, and 7,146 DEGs were assigned into three main GO functional categories in 9 vs. 0 h, 24 vs. 0 h, and 72 vs. 0 h, respectively. We also discovered several DEGs involved in phytohormone synthesis pathway and plant hormone signaling pathway. It was concluded that the decreased transcription of PYL resulted in the weak ABA signal transduction pathway. Moreover, decreased SA content caused by the low-expressed PAL might impact the resistance of S. tonkinensis seedlings under waterlogging stress. Our research may provide a scientific basis for the understanding of the endogenous hormone response mechanism of S. tonkinensis to waterlogging and lay a foundation for further exploration of the waterlogging defect resistance genes of S. tonkinensis and improving its resistance to waterlogging stress.
... Benzoin, a water-insoluble resin obtained from styrax species, has been widely used in perfume, antiseptic and topical adhesive agents. The major constituents of benzoin resin are conifeyl benzoate, benzoic acid, cinnamic acid and p-carmaryl cinnamate, as well as triterpenoids as minor compounds 11 . These components exhibit antibacterial and antioxidant activities 12 . ...
... There have been many studies on bioactive [2], therapeutic effect [3]. The chemical compositions of Benzoin resin are Benzoic acid, Cinnamic acid, Vanillin, Benzyl benzoate, Cinnamyl cinnamate, Benzyl cinnamate, Coniferilic alcohol, and Siaresinolic acid [4,5,6]. ...
Today, fixatives from natural raw materials are gradually replacing fixatives synthesized from chemicals. The arm of this research is the study of same useful resin in Vietnam for fixative substance in blending fragrance. We obtained Benzoin resin from Styrax tonkenensis Pierre plant in Ha Giang province, Canarium resin from Canarium Album L. in Dak Nong district, Dak Lak province, and Agarwood pulp of Aquilaria crassna plant in Binh Thuan province Vietnam. The material used in the experiment for the natural fragrance was taken from the project of Vietnam essential oils and related natural products. The method of this process is resin extraction by volatile solvents. The resin is dissolved in alcohol 96% and the distilled alcohol is removed to obtain absolute. The method of assessment of product quality in this study is using the olfactory to assess the odour of samples over time. Benzoin resin, Canarium resin, and Agarwood resin of Vietnam are useful fixatives in blending fragrance. The fixative ability of Benzoin resin absolute is not equal to the ability of Agarwood resin absolute but better than the ability of Canarium resin absolute. Through research and experiment, we can see Benzoin resin, Canarium resin and Agarwood resin are precious. They can be used as a good fixative in aromatherapy. This is a natural resin, a kind of resource available in Vietnam. Therefore, it is recommended for further research, exploitation, and effective use of this resource.
... 6 The bark is a source of benzoin, used as a flavoring agent and for incense, perfumes and medicines. 7,8 Its seed has a high oil concentration based on dry mass (about 60%) and excellent fatty acid (FA) composition with a high percent of unsaturated FAs, 9 especially oleic acid (C18:1) and linoleic acid (C18:2), meeting the biodiesel standards of the USA, Germany, the European Union and China. ...
BACKGROUND
Styrax tonkinensis is a white‐flowered tree with considerable potential as a feedstock source for biodiesel production from the oily seed contained within its nutlike drupes. Transcriptome changes during oil accumulation have been previously reported, but not concurrent changes in the proteome.
RESULTS
Using proteomic analysis of samples collected at 50, 70, 100 and 130 days after flowering (DAF), we identified 1472 differentially expressed proteins (DEPs). Based on their expression patterns, we grouped the DEPs into nine clusters and analyzed the pathway enrichment. Proteins related to starch and sucrose metabolism were most abundant at 50 DAF. Proteins involved in fatty acid (FA) biosynthesis were mainly grouped into a cluster that peaked at 70 DAF. Proteins related to protein processing in endoplasmic reticulum had two major patterns, trending either upwards or downwards, while proteins involved in amino acid biosynthesis showed more complex relationships. We identified 42 key enzymes involved in lipid accumulation during kernel development, including the acetyl‐CoA carboxylase complex (ACC) and the pyruvate dehydrogenase complex (PDC). One oil body membrane protein, oleosin, continuously increased during kernel development.
CONCLUSION
A regulatory network of oil accumulation processes was built based on protein and available transcriptome expression data, which were in good temporal agreement. This analysis placed ACC and PDC in the center of the network, suggesting that the glycolytic provision of substrate plays a central regulatory role in FA biosynthesis and oil accumulation. © 2021 Society of Chemical Industry.
... [3][4][5][6] Benzoin, as an important organic synthesis intermediate, has wide applications in the production of medicines, spices and daily chemicals. [7][8][9] However, the current catalytic oxidation synthesis of benzoin usually uses highly toxic cyanide as a catalyst, which is likely to cause pollution during the operation, signicantly limiting its further applications. 10 Therefore, there is an urgent need to design and construct a cheap and environmentally friendly heterogeneous photocatalyst for efficient benzoin condensation reaction. ...
Photocatalytic organic synthesis is mostly limited by the shortcomings of insufficient light absorption, high photogenerated electron-hole recombination rate and inadequate reactive sites of photocatalysts. To solve these problems, phosphorus-doped g-C3N4with a porous structure was constructed. Benefiting from enhanced light absorption and electron-hole separation efficiency, PCNT has intensive oxygen activation ability to generate superoxide radicals, and is highly active in organic synthesis. In addition, PCNT has enhanced surface nucleophilicity, which is conducive to the carbon-carbon coupling process of the intermediate product benzaldehyde molecules and benzyl alcohol molecules in the benzoin condensation reaction. Metal-free PCNT is expected to replace the previously used highly toxic cyanide catalysts and provide a new way for the low-cost and efficient photocatalytic synthesis of benzoin.
... Styrax benzoin is acrid, impressively aromatic and have strong vanilla like smell [9]. Main components of Styrax benzoin are benzaldehyde, benzoic acid, benzyl benzoate, cinnamic acid and vanillin [6]. ...
Styrax benzoin (benzoin resin) is a perennial tree belonging to the family (Styracaceae). It has been cultivated in the different regions of the world for thousands of year for incense and pharmaceutical preparations. Styrax benzoin usually contains benzaldehyde, benzoic acid, benzyl benzoate cinnamic acid and vanillin. Its chemical composition is influenced by the place of its origin, geographical, and climatic conditions. Styrax benzoin has been used traditionally for the treatment of skin diseases, arthritis, wounds, muscle pain, anxiety, and nervous disorders. Benzoin oil is widely used in the food, drinks and alcoholic beverage to give flavor, and for varnishing woods. The methods of production of resins are much traditional so there is a growing need to develop the new methods to maximize the production of resins.
... The chemical properties of benzoic resin have been investigated. [5,6], and [7]. Certainly, this product is a potential supplement to a solid and pulverized coal. ...
... The history of medicine and pharmacy is well known for using plant oleo-gumresins and extracts in curing diseases; these are known to have analgesic, antioxidant, antifungal, antiseptic, antibacterial, astringent, sedative, and stimulant therapeutic properties, among others [12][13][14][15][16][17][18][19][20][21]. The bioactivity of oils and extracts obtained species Commiphora myrrha, Styrax benzoin, and Boswellia papyrifera has been investigated by several researches [22][23][24][25][26][27][28][29][30][31]; these aromatic resins basically consist of monoterpenes (C10H16), triterpenes (C30H48), and sesquiterpenes (C15H24) with unique combinations, besides benzoic, myrrholic, and boswellic acids, respectively [32][33][34][35][36][37]; the demonstration of the presence of secondary metabolites in medicinal plants oils, extracts, and resins provides a scientific validation for the popular use of these plants [38][39][40][41][42]. ...
This experimental study investigates the bioactive potential of filaments produced via hot melt extrusion (HME) and intended for fused deposition modeling (FDM) 3D printing purposes. The oleo-gum-resins from benzoin, myrrha, and olibanum in pure state and also charged with 10% of metal oxide nanoparticles, TiO 2 , P25, Cu 2 O, and MoO 3 , were characterized by ultraviolet-visible (UV-Vis) and Fourier transform infrared (FTIR) spectroscopy, energy-dispersive X-ray microanalysis (EDXMA), scanning electron microscopy (SEM), and differential scanning calorimetry (DSC). Disks were 3D-printed into model geometries (10 × 5 mm) and the disk-diffusion methodology was used for the evaluation of antimicrobial and antifungal activity of materials in study against the clinical isolates: Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli , and Candida albicans . Due to their intrinsic properties, disks containing resins in pure state mostly prevent surface-associated growth; meanwhile, disks loaded with 10% oxides prevent planktonic growth of microorganisms in the susceptibility assay. The microscopy analysis showed that part of nanoparticles was encapsulated by the biopolymeric matrix of resins, in most cases remaining disorderly dispersed over the surface of resins. Thermal analysis shows that plant resins have peculiar characteristics, with a thermal behavior similar to commercial available semicrystalline polymers, although their structure consists of a mix of organic compounds.
... La résine de S. tonkinensis compte parmi ses constituants l'acide benzoïque sous sa forme libre, le benzaldéhyde (P3), le coniféraldéhyde (P4), la vanilline (P5) -ou l'isovanilline (P6) selon Hovaneissian et al. (2008)-, l'acide vanillique (P7), l'alcool coniférylique (désigné également par le terme de lubanol, P8), le benzoate de benzyle (P9), le benzoate de p-coumaryle (P10) et le benzoate de coniféryle (P11;Fernandez et al., 2003, Wang et al., 2006b, Hovaneissian et al., 2008, Burger et al., 2016. Ce dernier est, de par son abondance, considéré comme le marqueur chimiotaxonomique de l'espèce(Hovaneissian et al., 2008). ...
Ces travaux d'archéométrie concernent l’étude moléculaire par GC-MS de marqueurs lipidiques (biomarqueurs) préservés au sein de sols archéologiques et de substances végétales impliquées en tant qu'ingrédients dans la confection d’artefacts. Des analyses complémentaires en isotopie du carbone de composés individuels et des mesures de datation au 14C (AMS MICADAS) de la matière organique totale des sols, d'extraits lipidiques et d'un composé individuel (miliacine) ont également été effectuées. Cette approche a permis:- de montrer l’existence de la culture de millet dès l’âge du Bronze en Alsace, les sols associés à cette culture et leur contenu organique ayant été piégés et préservés dans des silos à grains enterrés datés de l’âge du Fer.- d'identifier la nature de structures archéologiques comme étant d'anciennes latrines et une aire de stabulation de bétail via l'identification de stéroïdes fécaux.- d'établir des critères chimiotaxonomiques fiables basés sur l'analyse des lipides pour l’authentification de résines de styrax et de liquidambars.- d'identifier la nature d'une résine issue de Styrax officinalis ayant été incorporée dans l’enduit organique ornant un crâne décoré (IXème millénaire av. J.-C., site de Nahal Hemar, Israël).- de mettre en évidence l’emploi de brai de bouleau comme agent collant lors de la confection d’un bijou daté du Premier âge du Fer.
... Except for compound 6, which is a metabolic phenolic precursor, these compounds can be classified as phenolics. Besides compound 1, which is a position isomer of 3, all of the selected compounds are known as polar constituents of styrax [19][20][21][22][23]. ...
In this study the first supercritical fluid based protocol for the extraction, analysis, and isolation of six polar compounds, i.e., o-vanillin (1), styracin (2), vanillin (3), trans-cinnamic acid (4), vanillic acid (5), and shikimic acid (6), was developed. First, eight styrax resin products (R1-R8) obtained from various Liquidambar tree species, which are known to contain compounds 2-6, were extracted with a 1 : 1 mixture of supercritical CO2 and EtOH. Within 4 minutes, the compounds were successfully baseline separated on an Acquity UPC(2) BEH 2-EP (3.0 × 100 mm, 1.7 µm) column using a mobile phase of supercritical CO2 and MeOH with 0.1 % phosphoric acid. The compounds were quantified and the method was validated according to current ICH guidelines. Scaling up to preparative supercritical fluid chromatography using a Viridis BEH 2-EP (10 × 250 mm, 5 µm) column allowed for a fast separation and isolation of the selected constituents 2 and 4 from R6 within 7 minutes. This supercritical fluid protocol is easily adaptable to compounds of similar polarity. The increase in speed and its environmental friendliness underline its superiority over conventional set-ups.
Indonesia is known for its rich biodiversity and the production of several endemic essential oils that are popular in the cosmetics industry. Essential oils are highly concentrated aromatic liquids derived from various plant materials, such as flowers, leaves, bark, stems, or roots. The pleasing fragrance, therapeutic effects, and potential benefits for skin care make essential oils a common ingredient in cosmetics. Various essential oils in Indonesia are native to the region and frequently applied in cosmetics. These include patchouli, clove, citronella, cananga, vetiver, lemongrass, oud, sandalwood and benzoin oils. Other common oils include lavender, tea tree, chamomile, rose, peppermint, and frankincense. Various methods for extracting essential oils include steam distillation, cold pressing and solvent extraction. The chemical composition can vary significantly depending on species, growing conditions, extraction method, and harvest time. Essential oils comprise a complex mixture of volatile organic compounds, including terpenes, aldehydes, phenols, ketones, alcohols, esters, and oxides. These compounds possess numerous beneficial properties, such as antimicrobial, analgesic, antiseptic, anti-inflammatory, and antioxidant effects. Essential oils can also have antifungal and sedative effects, contributing to their pleasant aroma. They are often employed in skin care products like creams, lotions, and serums to help with skin irritation and relaxation. Some essential oils are highly valued for their pleasing aroma and are applied in perfumes, hair care items, and moisturizers. The biomass of certain plants can also be involved in cosmetics, including leaves, flowers, stems, and other parts. However, it is crucial to properly formulate and understand the potential effects on the skin, as essential oils are highly concentrated and should be diluted appropriately before application. It is advisable to perform patch tests and consult a qualified expert to ensure safety and efficacy.
Studies on drug discovery from natural ingredients are important to determine the pharmacological effects of the compound’s content so that it can be used to treat diseases. Kemenyan (Styrax benzoin) resin has been widely used by the local community for various purposes, including medicine. This review article aims to provide a comprehensive view of the potency of Kemenyan resin and its active compounds so that they could be used and developed to treat diseases in the future. The method used was based on searching for scientific literature in national and international journals. The results showed that the Kemenyan resin contains active compounds, including cinnamic acid, benzoic acid, benzaldehyde, benzyl benzoate, vanillin, styrene, styracin, coniferyl benzoate, benziresinol resin, resinotannol, sterols, phthalic acid, and sumaresorcinol. These compounds are known to have various pharmacological effects, including antibacterial, anesthetic, anti-inflammatory, antispasmodic, antimutagenic, fungicidal, herbicidal, tyrosinase inhibitory, and LDL synthesis inhibitory effects. Based on these studies, it can be concluded that the Kemenyan resin has great potential for the treatment of various diseases.
The tree species in the Martelu Purba Nature Reserve has been identified. There were 39 plant species from 27 families. Publication of the benefits of each tree species in Martelu Purba Nature Reserve has not been well done. The trees have good potential for further exploration to discover their real benefits for human welfare. This research aims to identify the benefits of the Martelu Purba Nature Reserve. The method used in this study was an exploratory method of tree species in the Ancient Martelu Nature Reserve, and then the benefit categories of each type were determined with reference to the book Indonesian Useful Plants by K. Heyne. Based on research results, the benefits of trees are classified into six categories: raw materials for medicines, food sources for humans and animals, trees to improve environmental conditions, heavy and light construction materials, natural dyes, and paper-making materials. Each type has more than one benefit. Around 35%, or 24 species, are used for consumption; as many as 29%, or 20 species, are used as medicinal plants and as building materials. 21%, or 14 species; besides that, there are tree species for which the local community uses the sap and Gamblea malayana (MRHend.) CBShang, Lowry & Frodin as a phytoremediation plant.
Introduction:
Depending on their terpenoid and phenolic constituents plant resins can be classified as diterpenoid, triterpenoid or phenolic resins; thereby the profile of diterpenes and triterpenes is considered as genus- or even species-specific.
Objectives:
We aimed to develop a simple, rapid, inexpensive, sensitive and specific method for the identification of resin-specific triterpenoid and phenolic compounds in plant resins using (HP)TLC [(high-performance) thin-layer chromatography] combined with APCI-MS (atmospheric pressure chemical ionisation mass spectrometry) and post-chromatographic detection reactions.
Methods:
Twenty resin samples from different plant species were analysed. Different extraction procedures, post-chromatographic detection reagents as well as various sorbents and solvents for planar chromatography were tested. To evaluate the potential of the optimised (HP)TLC-APCI-MS methods, parameter such as limit of detection (LOD) was determined for selected marker compounds.
Results:
Our protocol enabled qualitative analyses of chemotaxonomic molecular markers in natural resins such as dammar, mastic, olibanum and benzoin. For the first time, the application of thionyl chloride-stannic chloride reagent for a specific post-chromatographic detection of triterpenes is reported, sometimes even allowing discrimination between isomers based on their characteristic colour sequences. For triterpene acids, triterpene alcohols and phenolic compounds, detection limits of 2-20 ng/TLC zone and a system precision with a relative standard deviation (RSD) in the range of 3.9%-7.0% were achieved by (HP)TLC-APCI-MS. The applicability of the method for the analysis of resin-based varnishes was successfully tested on a mastic-based varnish. Thus, the method we propose is a helpful tool for the discrimination of resins and resin-based varnishes with respect to their botanical origin.
Nine pairs of undescribed enantiomers, (±)-styraxoids A-I (1-9), were isolated from the resin of Styrax tonkinensis (Pierre) Craib ex Hart, and their structures were assigned by spectroscopic and computational methods. Compound (±)-1 is a pair of degraded lignans, and the remaining compounds (±)-(2-9) are phenylpropanoid skeletons. Compounds (±)-8 and (±)-9 feature a 1,3-dioxolane moiety. The biological evaluation showed that both enantiomers of 1 could inhibit LPS-induced INOS and COX-2 in RAW264.7 cells in a dose-dependent manner.
Benzoin is an incomplete lithified resin secreted from the trunk of the Styrax Linn. that is known as "semipetrified amber" and has been widely used in medicine due to its blood circulation-promoting and pain-relieving properties. However, the lack of an effective species identification method due to the numerous sources of benzoin resin and the difficulty of DNA extraction has led to the uncertainty of species of benzoin in the trade process. Here, we report the successful extraction of DNA from benzoin resin containing bark-like residues and the evaluation of commercially available benzoin species using molecular diagnostic techniques. By performing a BLAST alignment of ITS2 primary sequences and homology prediction analysis of ITS2 secondary structures, we found that commercially available benzoin species were derived from Styrax tonkinensis (Pierre) Craib ex Hart. and Styrax japonicus Sieb. et Zucc. of the genus Styrax Linn. In addition, some of the benzoin samples were mixed with plant tissues from other genera, accounting for 29.6%. Therefore, this study provides a new method to solve the problem of species identification of semipetrified amber benzoin using information from bark residues.
Benzoin, also known as semipetrified amber, is the resin secreted from the trunk of the benzoin plant. This medicinal material has blood circulation-promoting and pain-relieving properties. There are approximately 130 species of benzoin plants in the world, and the resin of many plants in the benzoin genus is used, so there is confounding of the species of origin. In this study, DNA was successfully extracted from the semipetrified amber medicinal material benzoin, and the species of benzoin in the medicinal herb market were evaluated by DNA barcoding. BLAST comparison of ITS2 primary sequences and homology prediction analysis of ITS2 secondary structures showed that the commercially available benzoin base originated from Styrax tonkinensis (Pierre) Craib ex Hart. and Styrax japonicus Sieb. et Zucc. of the genus Styrax Linn., and tissue from other genera was also detected to be mixed in with some samples, accounting for 29.6% of the samples. There is a risk that benzoin resin medical materials will be mixed with tissues from other plants. This is the first report on the subject, and the approach taken provides technical feasibility for the identification of the basis of the benzoin resin medical materials.
Natural resins such as benzoin, propolis and rosin have been widely employed in the pharmaceuticals. In this study, in situ forming gels (ISG) were prepared using natural resins as matrix forming agents to deliver vancomycin hydrochloride (VH) for periodontitis treatment. The formulations were investigated for their physicochemical properties, drug release and antimicrobial activities. Transformation from a solution to a solid matrix was achieved after the formulas were exposed to a simulated crevicular fluid. The rate of resin matrix formation was found to decrease with time and became more opaque owing to gradual phase separation with resin network formation. They flowed with pseudo-plastic behavior and provided appropriate injectability as well as good mechanical properties. Sustained VH release was attained for a 5-day period. VH-loaded natural resin ISGs inhibited against Staphylococcus aureus, Porphyromonas gingivalis, Candida albicans, and Streptococcus mutans. Natural resin-based ISGs comprising of propolis or benzoin showed a more effective delivery of VH than that of rosin. Thus, VH-loaded benzoin and propolis ISGs were found to have a possible application for infected periodontitis treatment.
Two triterpenes (1 and 2) and eight lignans (3–10) were isolated from the ethyl acetate-soluble fraction of the leaves of Styrax tonkinensis (Pierre) Craib ex Hartw (Styracaceae). Their structures were established as ursolic acid (1), pomolic acid (2), 3,3′-bis(3,4-dihydro-6-methoxy-2H-1-benzopyran) (3), rac-(8α,8′β)-4,4′-dihydroxy-3,3′-dimethoxylignan-9,9′-diyldiacetate (4), (-)-secoisolariciresinol (5), (+)-pinoresinol (6), 4,4′-dihydroxy-3,3′-dimethoxy-9-ethoxy-9,9′-epoxylignan (7), (2S,3R, 4R)-4-[1-ethoxy-1-(4-hydroxy-3-methoxy)phenyl]methyl-2-(4-hydroxy-3-methoxy)phenyl-3-hydroxymethyl-tetrahydrofuran (8), (-)-neo-olivil-(9-O-9″)-seco-isolariciresinol (9) and isolariciresinol (10) based on MS, ¹H-and ¹³C-NMR spectral data. All these compounds (1–10) were firstly isolated from this plant, and compounds 2–5 and 7–9 were reported from the Styrax genus for the first time. Furthermore, the chemotaxonomic significance of the isolated compounds was discussed.
Ethnopharmacological relevance:
Benzoinum (Styraceae) is a traditional Chinese medicine used to treat stroke and other cardio-cerebrovascular diseases for thousands of years. Benzoinum has also proven to have diverse pharmacological activity, but the neuroprotection mechanism of apoptosis in ischaemic stroke was not determined.
Aim of this study:
To investigate the protective effect of a neurovascular unit (NVU) and the mechanisms of benzoinum on cerebral ischaemic rats.
Materials and methods:
The neuroprotective activity of benzoinum against middle cerebral artery occlusion (MCAO)-induced cerebral ischaemic injury. Neurological scores, 2,3,5-Triphenyltetrazolium chloride (TTC) staining, and hematoxylin-eosin staining (HE) staining were conducted to evaluate the neurological damage. Infarction rate and denatured cell index (DCI) were also calculated. The ultrastructure of neuron and blood-brain-barrier (BBB) was observed by transmission electron microscopy (TEM). Immunohistochemistry and reverse transcription-polymerase chain reaction (RT-PCR) were used to detect Bax, Bcl-2 and Caspase 3 expression. Furthermore, Claudin 5 also was detected through immunohistochemistry.
Results:
Benzoinum could significantly improve neurological function score and reduce cerebral infarction rate and DCI. In addition, benzoinum alleviated pathomorphological change and apoptosis in the brain tissue of MCAO rats. The results of TEM and claudin 5 expression of immunohistochemistry showed that benzoinum could play a neuroprotective effect in NVU. Also, benzoinum-enhanced Bcl2, and reduced Bax and Bax/Bcl-2 and Caspase 3, suggest that benzoinum provided a neuroprotective effect by inhibited cell apoptosis.
Conclusion:
Benzoinum could play a neuroprotective role and regulate apoptosis for repair and stabilisation of NVU. This anti-apoptosis activity might be associated with the downregulation of Bax and Caspase 3, and the upregulation of Bcl2. Our present findings provide a promising medication for the treatment of ischaemic stroke.
Two new phenylpropanoids, named stytonkinol A (1) and stytonkinol B (2), have been isolated from the resin of Styrax tonkinensis (Pierre) Craib ex Hartw. Their structures were determined by spectroscopic analysis, including 1D and 2D NMR, and HR-ESI–MS. Two isolated compounds were assayed for cytotoxic activities against five tumor cell lines (HepG-2, A549, Hela, MCF-7, and PC-3) by Cell Counting Kit-8 (CCK-8) test in vitro. The cytotoxic effectiveness observed against Hela, and MCF-7 cell lines of compound 1 were superior or similar to the positive control cisplatin (IC50 values of 40.95 and 47.36 μM), with IC50 values of 26.75 and 45.16 μM, respectively, while it showed moderate cytotoxic activities against the HepG-2 and PC-3 cell lines. Compound 2 showed moderate cytotoxic activities on cells MCF-7 with IC50 values of 57.1 μM.Graphic abstract
Background:
Styrax tonkinensis (Pierre) Craib ex Hartwich has great potential as a woody biodiesel species having seed kernels with high oil content, excellent fatty acid composition and good fuel properties. However, no transcriptome information is available on the molecular regulatory mechanism of oil accumulation in developing S. tonkinensis kernels.
Results:
The dynamic patterns of oil content and fatty acid composition at 11 time points from 50 to 150 days after flowering (DAF) were analyzed. The percent oil content showed an up-down-up pattern, with yield and degree of unsaturation peaking on or after 140 DAF. Four time points (50, 70, 100, and 130 DAF) were selected for Illumina transcriptome sequencing. Approximately 73 million high quality clean reads were generated, and then assembled into 168,207 unigenes with a mean length of 854 bp. There were 5916 genes that were differentially expressed between different time points. These differentially expressed genes were grouped into 9 clusters based on their expression patterns. Expression patterns of a subset of 12 unigenes were confirmed by qRT-PCR. Based on their functional annotation through the Basic Local Alignment Search Tool and publicly available protein databases, specific unigenes encoding key enzymes, transmembrane transporters, and transcription factors associated with oil accumulation were determined. Three main patterns of expression were evident. Most unigenes peaked at 70 DAF, coincident with a rapid increase in oil content during kernel development. Unigenes with high expression at 50 DAF were associated with plastid formation and earlier stages of oil synthesis, including pyruvate and acetyl-CoA formation. Unigenes associated with triacylglycerol biosynthesis and oil body development peaked at 100 or 130 DAF.
Conclusions:
Transcriptome changes during oil accumulation show a distinct temporal trend with few abrupt transitions. Expression profiles suggest that acetyl-CoA formation for oil biosynthesis is both directly from pyruvate and indirectly via acetaldehyde, and indicate that the main carbon source for fatty acid biosynthesis is triosephosphate originating from phosphohexose outside the plastid. Different sn-glycerol-3-phosphate acyltransferases are implicated in diacylglycerol biosynthesis at early versus late stages of oil accumulation. Triacylglycerol biosynthesis may be accomplished by both diacylglycerol and by phospholipid:diacylglycerol acyltransferases.
Benzoin is an important feedstock with high additional value for its extensive use in chemical industry. Benzoin condensation characterized by C–C coupling between benzaldehyde requires the use of nucleophilic catalysts including cyanide or N-heterocyclic carbene and is restricted to organic medium such as MeCN, diethyl ether, etc. Construction of efficient and non-toxic catalysts for benzoin synthesis still remains a challenge. Herein, highly selective (97%) benzoin synthesis from benzyl alcohol was achieved over potassium modified g-C3N4 via light-driven tandem selective oxidation and C–C coupling. The outstanding performance was attributed to alkali modifications on the electronic structure and surface chemical environment of g-C3N4. K⁺ intercalation not only facilitated the light harvesting as well as the transport of charge carriers, but also induced surface deprotonation of g-C3N4 and thus remarkable nucleophilicity for prompting the C–C coupling reactions. This work sheds light on the design of earth-abundant inorganic photocatalysts for C–C coupling reactions such as the green synthesis of benzoin under ambient conditions.
The Styracaceae contains 11 genera and approximately 160 species consisting of small trees and shrubs, mostly native to tropical and subtropical regions. This family is well-known by the genus Styrax, which is notorious due to the production of resinous material, a pathological product, harvested by making incisions into the trees bark. The gum is used in perfumes, as antiseptic, expectorant, incense, and fumigating material. This paper reviews the phytochemical and biological studies carried out on 11 species of this family. A total of 92 papers were consulted, and 130 compounds were described, thus these data indicate that Styrax is by far the largest genus in the family, and the only which has been extensively investigated.
Contribution of analytical chemistry to the study of styrax and benzoin botanical exudates. For several resins, gaps in botanical classification and ambiguities in their designation induce difficulties to correlate with precision botanical species and chemical composition. It is the case of balsamic resins called styrax and benzoins, for which there are important linguistic, botanical and chemical confusions. This study by Fourier Transform Infrared (FTIR) spectroscopy and High-Performance Liquid Chromatography (HPLC) of several resinous samples made it possible to specify the chemical and botanical membership of these substances at the origin of many interrogations. It also provided interesting information about the ways to obtain or to transform the resinous matters while evoking the possibility of adulterations or confusions with dammar resin issued from geographically close vegetable species. To cite this article: M. Hovaneissian et al., C. R. Chimie 9 (2006).
The volatile extract composition of two different benzoin gums, Siam and Sumatra, were analysed by GC–MS. Twenty components representing more than 99.1% of the oil from Siam and 29 components representing more than 97.4% of the oil from Sumatra were analysed. The major components were benzyl benzoate (76.1–80.1%) for the two oils and benzoic acid (12.5%), methyl benzoate (1.5%) and allyl benzoate (1.5%) for Siam, and styrene (2.3%), cinnamic acid (3.5%) and benzyl cinnamate (3.3%) for Sumatra. Volatile compounds of oils and crushed benzoins were also studied using solid-phase microextraction (SPME) employing carboxen/polydimethylsiloxane and carbowax/divinylbenzene fibres. Copyright © 2003 John Wiley & Sons, Ltd.
The quality control of natural raw materials is a challenging issue for the food, cosmetic, perfume and tobacco industries. The applicability of an electronic nose for the discrimination of origin, qualities and harvesting year of a natural raw material (benzoin gum) currently used by all those industries was tested. An electronic nose including 18 metal oxide sensors was used to analyse and discriminate 56 benzoin gum samples according to their origin (Siam and Sumatra), quality grade, variety (mixture of gums traded as benzoin gums) and year of harvesting. Thanks to its sensitivity, the electronic nose based on metal oxide sensors demonstrated a high ability to assess both the quality and the organoleptic features of the benzoin gum samples. Fast analysis and ease of use make this instrument a good quality control tool. A comparison with an electronic nose based on fingerprint mass spectrometry was also studied. Copyright © 2006 John Wiley & Sons, Ltd.
Static-headspace (S-HS), headspace–solid phase microextraction (HS-SPME) and headspace sorptive extraction (HSSE) have been applied to the analysis of different grades of benzoin gums Siam and Sumatra. This study led to the identification of 58 compounds by GC-RI and GC-MS: 42 of them were characterized in Siam benzoin gum (grades 3 and 5) and 40 of them in Sumatra (grades B and D). SPME using divinylbenzene[sol ]carboxen[sol ]polydimethylsiloxane fiber and HSSE are complementary in these conditions and seem to be the most suitable techniques to identify volatile compounds of benzoin gums. S-HS is less sensitive but represents a good method for the quality control of these gums. For this reason it has been applied directly coupled to mass spectrometry for a rapid differentiation between several benzoin gum qualities. Copyright © 2005 John Wiley & Sons, Ltd.
An HPLC and GC study has been conducted on the aromatic oleoresins styrax and benzoin produced by several American, Mediterranean and East-Asian trees, and widely used in ancient civilisations for their therapeutic and odoriferous properties. Initial experiments were performed by HPLC-PAD-fluorimetry for the analysis of several aromatic components, and then completed by GC-MS for the characterisation of both aromatic and triterpenic derivatives. In this work, it was crucial to isolate from fresh natural exudates, and to characterise by two-dimensional NMR, some of the major constituents in order to extend the standard molecular pool prior to chromatographic identifications. This study reveals coniferyl benzoate as an excellent distinctive fluorescent biomarker of Siam benzoin substrate. It also confirms that fluorimetric-coupled detection is a powerful analytical tool for the identification of compounds in Hamamelidaceae extracts that are almost undetectable by UV. GC-MS was successfully applied to the determination of the botanical origin of Sumatra benzoin, and to the identification of lupeol [3beta-lup-20(29)-en-3-ol] for the first time in such balsam-type materials.
Sumatra benzoin resins originating from two species of Styrax were studied using modern analytical techniques. Analysis of these types of resins usually involves several steps including alkaline hydrolysis, derivatization of the polar groups and chromatography. Two different resins, and three different qualities from each resin, were investigated using a fast analytical method which omits the hydrolysis step and makes it possible to identify all of the individual components of the resin in one gas-chromatography–mass spectrometry measurement. Resins from both Styrax benzoin Dryand and S. paralleloneurum Perk contain free cinnamic and benzoic acids and their corresponding esters with p-coumaryl and coniferyl alcohols, although in different relative amounts. Pinoresinol and some higher molecular weight esters of cinnamic and benzoic acids were also found. The structure of these compounds was verified by high performance liquid chromatography–continuous flow fast atom bombardment mass spectrometry. For quantitation, gas chromatography with flame ionization detection was performed. Molecular response factors of the identified compounds were calculated as correction factors of the peak areas. © 1997 by John Wiley & Sons, Ltd.
Siam Benzoin gum and coniferyl benzoate isolated from the gum were reduced with lithium aluminium hydride. In addition to the anticipated coniferyl alcohol, p-coumaryl alcohol was isolated from the phenolic fraction and it was found that the benzoate in Siam Benzoin gum contains 15 per cent p-coumaryl alcohol; sinapyl and caffeyl alcohol were shown to be absent. By use of a lithium aluminum hydride reduction coniferyl alcohol can be obtained directly from Siam Benzoin gum, whereas attempted saponification only results in polymerization of the benzoate ester.
Two novel tetrahydropyran sesquineolignans with a new carbon skeleton, named morinols A (1) and B (2), and other ten novel neolignans, named morinols C-L (3–12), along with two known lignans, pinoresinol (13) and lariciresinol (14), have been isolated from the roots of Chinese medicinal herb, Morina chinensis. The structures of all of the compounds have been determined mainly on the basis of modern spectroscopic evidences (1NMR, 13C NMR, DEPT, 1H-1H COSY, NOESY, HSQC, HMBC and HRMS), as well as chemical transformation. The inhibitory effects of the isomers, morinols A (1) and B (2), on cytokine production have been studied, the results indicated that morinol B (2) has more stronger activity than morinol A (1). Morinols B (2), E (5) and G (7) were verified should be enantiomeric natural products by means of MTPA and 2NMA.
A new sesquiterpene was isolated from extracts of Sumatra benzoin gum. Its structure was elucidated by means of mass spectrometry and two-dimensional NMR. This new compound presented an acenaphthylene-type skeleton unpreviously described among the family of sesquiterpene hydrocarbons.
Chromatographic separation of 10 triterpenoids (alpha-amyrin, beta-amyrin, delta-amyrin, lupeol, lupenon, lupeol acetate, cycloartenol, cycloartenol acetate, ursolic acid, oleanolic acid) and 2 sterols (stigmasterol and beta-sitosterol) was studied. The chromatographic techniques included silica gel and reversed-phase (C18 RP) thin-layer chromatography (TLC) and C18 RP high-performance liquid chromatography (HPLC) using UV and mass spectrometric (MS) detection with atmospheric pressure chemical ionization (APCI). The TLC separation of the isomeric triterpenols lupeol, alpha-amyrin, beta-amyrin and cycloartenol was achieved for the first time using C18 RP-HPTLC plates. Cycloartenol could be separated from related compounds only on C18 RP-TLC but not on the C18 RP-HPLC. delta-Amyrin isolated from the tomato fruit surface extract could be separated from other amyrins only by HPLC. Tandem mass spectrometry allowed discrimination between the isomers lupeol, alpha-amyrin, beta-amyrin, delta-amyrin, cycloartenol and between lupeol acetate and cycloartenol acetate. The combination of 3 TLC methods and 2 HPLC methods enables qualitative determination of all 12 compounds and proves to be useful for the analysis of plant extracts. It is recommended that TLC screening on silica gel and C18 RP be performed before HPLC analysis.
An analytical procedure based on alkaline hydrolysis, solvent extraction and trimethyl-silylation followed by gas chromatography-mass spectrometry (GC-MS) analysis was used to study the chemical composition of benzoe and storax resins, water-insoluble exudates of trees of the Styrax and Liquidambar genus. They are chemically characterised by having aromatic acids, alcohols and esters as their main components and are thus known as aromatic and/or balsamic resins. This analytical procedure allowed us to characterise the main components of the two resins and, even though cinnamic acid is the main component of both the resins, the presence of other characteristic aromatic compounds and triterpenes permitted us to distinguish between the two materials. All the compounds identified in benzoe resin were detected in an archaeological organic residue from an Egyptian ceramic censer (fifth to seventh centuries a.d.), thus proving that this resin was used as one of the components of the mixture of organic materials burned as incense. These results provide the first chemical evidence of the presence of benzoe resin in an archaeological material from Mediterranean area.
Aromatic natural raw materials-Vocabulary (Indice de classement: T 75-006)
- Afnor Nf T
AFNOR NF T 75-006 (1998). Aromatic natural raw materials-Vocabulary (Indice de
classement: T 75-006). ICS. 01.040.71; 71.100.60.
Benzoe tonkinensis. 01 Chapter 10 Benzoin, a resin produced by Styrax trees in North Sumatra Province, Indonesia Forest products, livelihoods and conservation. Case studies of non-timbers forest product systems
- European Pharmacopoeia
European Pharmacopoeia, (2016) (8th ed.). Benzoe tonkinensis. 01/2016:2158.
Fernández, C. G. (2004). Chapter 10 Benzoin, a resin produced by Styrax trees in
North Sumatra Province, Indonesia. In K. Kusters & B. Belcher (Eds.), Forest
products, livelihoods and conservation. Case studies of non-timbers forest product
systems. Volume 1-Asia (pp. 151-168). Jakarta, Indonesia: CIFOR.
Monograph on benzoin
- M Kashio
- D V Johnson
Kashio, M., & Johnson, D. V. (2001). Monograph on benzoin.Thailand: Food and
Agriculture Organization of the United Nations Regional Office for Asia and the
Pacific Bangkok.
Pharmacognosie, phytochimie, plantes médicinales
- J Bruneton
Bruneton, J. (2009). Pharmacognosie, phytochimie, plantes médicinales (4th ed.
p. 1292). Paris: Tec & Doc Lavoisier.
High-performance thin-layer chromatography for the analysis of medicinal plants
- E Reich
- A Schibli
Reich, E., & Schibli, A. (2006). High-performance thin-layer chromatography for the
analysis of medicinal plants. Thieme Medical Publishers, p. 264.
Compendium of food additive specifications, 74th meeting
- Agriculture Food
- Organization
Food and Agriculture Organization (2011). Compendium of food additive
specifications, 74th meeting. FAO JECFA Monograph 11.
Perfume and flavor materials of natural origin (p. 736). Carol Stream
- S Arctander
Arctander, S. (1960). Perfume and flavor materials of natural origin (p. 736). Carol
Stream: Allured Publishing Corporation.
Evaluation of certain food additives and contaminants
World Health Organization (2011). Evaluation of certain food additives and
contaminants. 74th report of the Joint FAO/WHO Expert Committee on Food
Additives, WHO technical report series, 966, p. 136.
Forest products, livelihoods and conservation. Case studies of non-timbers forest product systems
- C G Fernández
Fernández, C. G. (2004). Chapter 10 Benzoin, a resin produced by Styrax trees in
North Sumatra Province, Indonesia. In K. Kusters & B. Belcher (Eds.), Forest
products, livelihoods and conservation. Case studies of non-timbers forest product
systems. Volume 1 -Asia (pp. 151-168). Jakarta, Indonesia: CIFOR.
Benzoe tonkinensis, Chemical and Technical Assessment (CTA) prepared by Susanne Rath, PhD, and reviewed by Harriet Wallin
JECFA -Chemical and Technical Assessment (2014). Benzoe tonkinensis,
Chemical and Technical Assessment (CTA) prepared by Susanne Rath, PhD, and
reviewed by Harriet Wallin, MSc.