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New insights in the chemical composition of benzoin balsams

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... 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]. ...
... 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]. ...
... 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. ...
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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.
... 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. ...
... 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]. ...
Conference Paper
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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.
... 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 Langenheim, 2003;Burger et al., 2016) (Figure 14). Figure 14. Benzoic and cinnamic acids, the most abundant molecules in benzoin resin . ...
Thesis
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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.
... 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 . ...
... 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]. ...
Article
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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.
... 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]. ...
Article
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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.
... 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). ...
Thesis
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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.
... 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 . ...
Article
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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.
... 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. ...
Article
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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. This article is protected by copyright. All rights reserved.
... 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). ...
Article
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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.
... 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. ...
... 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]. ...
Article
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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.
... 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]. ...
Article
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.
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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.
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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.
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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
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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.
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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.
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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.
Article
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.
Article
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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 tree’s 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.
Article
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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).
Article
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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.
Article
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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.
Article
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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.
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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.
Article
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.
Article
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.
Article
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.
Article
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.
Article
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.
Article
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.
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