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A Straightforward Synthesis of Pinocembrin. 皮诺曹蛋白的直接合成。
IF 1.6 4区 农林科学 Q3 CHEMISTRY, APPLIED Pub Date : 2025-01-01 DOI: 10.5650/jos.ess24245
Kento Iwai, Nagatoshi Nishiwaki

A simple synthetic method for pinocembrin from cinnamic acid and 1,3,5-trihydroxybenzene was provided. This method can be performed in one-pot two steps reaction using inexpensive chemical reagents, whereas conventional methods need multiple steps from somewhat expensive starting reagents. The experimental procedure is facilitated, that is, to a DMF solution of cinnamoyl chloride generated in situ, a solution of 1,3,5-trihydroxybenzene and AlCl 3 in DCE/PhNO 2 was added, and the resultant mixture was heated to afford pinocembrin. This method does not require protection of phenolic hydroxy groups.

提出了一种以肉桂酸和1,3,5-三羟基苯为原料合成肉桂素的简便方法。该方法可以在一锅两步反应中使用便宜的化学试剂,而传统的方法需要从一些昂贵的起始试剂进行多次反应。实验步骤简便,即在原位生成的肉桂酰氯DMF溶液中,加入DCE/ phno2中1,3,5-三羟基苯和AlCl 3的溶液,加热得到肉桂酰氯。这种方法不需要保护酚羟基。
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引用次数: 0
Preparation and Structural Properties of Gel Coating Films Containing Lipophilized Nanocarbon Particles Functionalized with Thixotropic Chains. 触变链功能化脂化纳米碳凝胶涂膜的制备及结构性能。
IF 1.6 4区 农林科学 Q3 CHEMISTRY, APPLIED Pub Date : 2025-01-01 DOI: 10.5650/jos.ess24166
Yuka Hasunuma, Shoma Sakamoto, Yui Yamagishi, Atsuhiro Fujimori

Gel coating films comprising nanodiamonds organo-modified with 12-hydroxystearic (12-OHC18 ) and stearic acids were prepared and characterized. Because molecules with 12-OHC18 groups can convert solvents into thixotropic gels, Gemini-type diamide derivatives with two 12-OHC18 chains were also introduced as thixotropic additives into the gel coating films. Although the 12-OHC18 -modified nanodiamonds did not lead to solvent gelation on their own, they displayed an affinity for the thixotropic additive molecules. The 12-OHC18 -modified nanodiamonds were localized near the surface of the nanofibers formed by the Gemini-type diamide derivative in the solvent, and the thixotropic properties of the supramolecular gel were confirmed. Nanoparticle aggregation and nanofiber crystallinity were found to be suppressed by the effect of 12-OHC18 modification in the gel coating films, making them suitable for cosmetic coating applications.

制备了由12-羟基硬脂酸(12-OHC18)和硬脂酸有机修饰的纳米金刚石凝胶涂层并对其进行了表征。由于含有12-OHC18基团的分子可以将溶剂转化为触变性凝胶,因此将具有两条12-OHC18链的gemini型二胺衍生物作为触变性添加剂引入到凝胶涂层中。虽然12-OHC18修饰的纳米金刚石本身不会导致溶剂凝胶化,但它们对触变性添加剂分子表现出亲和力。在溶剂中,12-OHC18修饰的纳米金刚石被定位在gemini型二胺衍生物形成的纳米纤维表面附近,并证实了超分子凝胶的触变性。经12-OHC18改性后的凝胶包衣膜可抑制纳米粒子聚集和纳米纤维结晶度,使其适合化妆品包衣。
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引用次数: 0
Analysis of Total, Free, and Esterified Sterols and Triterpene Alcohols in Edible Oils using a Gas Chromatography-Flame Ionization Detector.
IF 1.6 4区 农林科学 Q3 CHEMISTRY, APPLIED Pub Date : 2025-01-01 DOI: 10.5650/jos.ess24091
Kazuki Tada, Yuriko Suganuma, Aya Yoshinaga-Kiriake, Shota Koishi, Kazuaki Yoshinaga

Sterols and triterpene alcohols exist in free and esterified forms in edible oils. To date, only few studies have determined the content of free or esterified sterols and triterpene alcohols using gas chromatography-flame ionization detection (GC-FID). In this study, analytical conditions were optimized using free and esterified sterol standards. To analyze total sterol and triterpene alcohol (Method A), edible oil sample was saponified in the presence of an internal standard (IS, 5α-cholestan- 3β-ol). However, to analyze free sterol and triterpene alcohol (Method B), the sample was dissolved in hexane/ethyl acetate (90:10, v/v) in the presence of the IS, and the free sterol and triterpene alcohol fractions were isolated via silica gel chromatography. The fractions obtained from Methods A and B were derivatized separately as trimethylsilyl (TMS) ether and analyzed using GC-FID. The esterified sterol and triterpene alcohol contents of edible oil were calculated by subtracting the free sterol content (Method B) from the total content (Method A). The major sterols and triterpene alcohols in canola, soybean, rice bran oil, and lard were separated using a column coated with 5% diphenyl/95% dimethylpolysiloxane. The recovery rates of free sterols spiked into canola oil were 86-106% and 87-109%, while those of esterified sterols (sitosteryl palmitate) spiked into canola oil were 94-105% and -4-2% based on Methods A and B, respectively. The sterol and triterpene alcohol compositions of lard, canola, soybean, and rice bran oils were also determined using Methods A and B, and the results aligned well with those reported in the literature. Altogether, our methods can be successfully used to quantify the levels of sterols and triterpene alcohols in edible oils.

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引用次数: 0
NaturalEssential Oils: A Promising Therapy Way for Treating Ischemic Stroke. 天然精油:治疗缺血性中风的有效疗法。
IF 1.6 4区 农林科学 Q3 CHEMISTRY, APPLIED Pub Date : 2024-11-01 Epub Date: 2024-10-17 DOI: 10.5650/jos.ess24125
Yuanyuan Wu, Leying Gao, Yue Hu, Xiaofang He, Wenli Ye, Yu Long, Xiaoqiu Li, Jie Deng, Yin Ma, Huiyi Feng, Haolin Liu, Qianqian Wu, Nan Li

Stroke is an acute cerebrovascular disease with high morbidity, mortality, and disability, making it the second leading cause of death worldwide. Ischemic stroke (IS) accounts for the majority of strokes, and its pathogenesis is complex, often involving complications and sequelae. Currently, conventional clinical approaches are ineffective, with few drugs available for intravenous thrombolysis and mechanical thrombolysis limited by a short time window. With the poor efficacy of monotherapy, the search for new complementary or alternative therapies has become the focus of researchers. In traditional medicine, Chinese aromatherapy has a long history of using aromatic medicines to treat IS. Natural essential oils (EOs), as the main pharmacological substances in aromatic drugs, are composed of different ratios of active metabolites with multi-targets and multi-components, which makes EOs have a wide range of pharmacological effects. Modern studies have also shown that EOs extracts and isolated monomers are beneficial for pathologically complex CIS. Therefore, this paper summarizes the EOs and monomers obtained from EOs that can prevent and treat IS in the last 20 years, and finds that EOs exert their anti-CIS effects mainly through anti-oxidative stress, anti-inflammation, anti-apoptosis, and inhibition of excitotoxicity. The amelioration of IS complications by natural EOs and their active monomer components for the treatment of IS are further discussed.

脑卒中是一种急性脑血管疾病,发病率高、死亡率高、致残率高,是全球第二大死亡原因。缺血性脑卒中(IS)占脑卒中的绝大多数,其发病机制复杂,常伴有并发症和后遗症。目前,传统的临床方法效果不佳,可用于静脉溶栓的药物很少,而机械溶栓又受限于较短的时间窗。在单一疗法疗效不佳的情况下,寻找新的辅助或替代疗法成为研究人员关注的焦点。在传统医学中,中国芳香疗法使用芳香药物治疗 IS 的历史悠久。天然精油(EOs)作为芳香药物中的主要药理物质,由不同比例的活性代谢产物组成,具有多靶点、多成分的特点,使其具有广泛的药理作用。现代研究也表明,环氧乙烷提取物和分离单体对病理复杂的 CIS 有益。因此,本文总结了近 20 年来从环氧乙烷中提取的可预防和治疗 IS 的环氧乙烷和单体,发现环氧乙烷主要通过抗氧化应激、抗炎、抗细胞凋亡和抑制兴奋毒性来发挥抗 CIS 作用。该研究进一步探讨了天然环氧乙烷及其活性单体成分在治疗 IS 方面对 IS 并发症的改善作用。
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引用次数: 0
ChemicalComposition, Health Benefits and Future Prospects of Hairless Canary Seed (Phalariscanariensis L.): A Review. 无毛金丝雀种子(Phalaris canariensis L.)的化学成分、健康益处和未来前景:综述。
IF 1.6 4区 农林科学 Q3 CHEMISTRY, APPLIED Pub Date : 2024-11-01 Epub Date: 2024-10-17 DOI: 10.5650/jos.ess24108
Ayoub Amahrous, Mehdi Taib, Said Meftah, Elhassan Oukani, Bouyazza Lahboub

The increasing global population and the rise of health-conscious consumers have led to a growing demand for innovative foods and functional ingredients. Hairless canary seed (Phalaris canariensis L.), which has recently obtained regulatory food approval from Health Canada and the United States Food and Drug Administration (US-FDA), has the potential to meet these demands due to its unique nutrient profile and characteristics. Canary seed stands out among cereals and pseudo-cereals (gluten-free cereals) as it has the highest protein content and is gluten-free. Additionally, it contains significant amounts of tryptophan, an amino acid typically lacking in cereals. It is considered a true cereal grain that can be processed into flour, starch, and oil for various food and non-food applications. This article provides a comprehensive overview of the chemical composition, functional properties, and biological activities of canary seeds. It also explores the processing methods for incorporating these seeds into food and cosmetic products. Furthermore, suggestions for future research directions are presented to enhance the utilization of this plant. Overall, it is evident that Phalaris canariensis holds considerable potential as a sustainable crop that can be further developed.

随着全球人口的不断增长和注重健康的消费者的增多,对创新食品和功能性配料的需求也在不断增长。无毛金丝雀种子(Phalaris canariensis L.)最近获得了加拿大卫生部和美国食品药品管理局(US-FDA)的食品监管批准,由于其独特的营养成分和特性,有可能满足这些需求。金丝雀籽在谷物和假谷物(无麸质谷物)中脱颖而出,因为它的蛋白质含量最高,而且不含麸质。此外,它还含有大量色氨酸,这是谷物中通常缺乏的一种氨基酸。它被认为是一种真正的谷物,可加工成面粉、淀粉和油,用于各种食品和非食品用途。本文全面概述了金丝雀种子的化学成分、功能特性和生物活性。文章还探讨了将这些种子加工成食品和化妆品的方法。此外,文章还对未来的研究方向提出了建议,以提高这种植物的利用率。总之,金丝雀种子作为一种可持续发展的作物,显然具有相当大的潜力,可以进一步开发。
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引用次数: 0
Monitoring of Fatty Acid Derivatives and Vegetable Oils by the Quartz Crystal Microbalance. 用石英晶体微天平监测脂肪酸衍生物和植物油。
IF 1.6 4区 农林科学 Q3 CHEMISTRY, APPLIED Pub Date : 2024-11-01 Epub Date: 2024-10-17 DOI: 10.5650/jos.ess24121
Yasushi Endo

This study investigated the characterization of fatty acid derivatives and vegetable oils by the quartz crystal microbalance (QCM). Resonant frequency and resistance were monitored for fatty acid derivatives and vegetable oils by a QCM sensor at 35℃ and 55℃. The resonant resistance depended on varieties of fatty acid derivatives, although the resonant frequency was similar for them. Oleic acid showed higher resonant resistance than methyl and ethyl oleate and oleyl alcohol. The resonant resistance of fatty acid methyl esters showed lower value according to the unsaturation (numbers of double bonds). Glyceryl oleate showed remarkably higher resonant resistance than oleic acid and its esters. Triolein showed the highest resonant resistance among glyceryl oleate. The resonant resistances of vegetable oils also depended on their varieties and iodine value (IV). Olive oil with the lowest IV showed the highest resonant resistance, while linseed oil with the highest IV showed the lowest resonant resistance among tested vegetable oils. The resonant resistances of vegetable oils reduced with their IV. These results suggested QCM may be effective for identification of vegetable oils.

本研究利用石英晶体微天平(QCM)研究了脂肪酸衍生物和植物油的特性。通过石英晶体微天平传感器监测了脂肪酸衍生物和植物油在 35℃ 和 55℃ 下的共振频率和电阻。虽然脂肪酸衍生物的共振频率相似,但共振电阻取决于脂肪酸衍生物的品种。油酸的共振电阻高于油酸甲酯、油酸乙酯和油醇。脂肪酸甲酯的共振电阻值随不饱和度(双键数)的不同而降低。油酸甘油酯的共振电阻明显高于油酸及其酯类。在甘油油酸酯中,三油酸酯的共振电阻最高。植物油的共振电阻还取决于其品种和碘值(IV)。在测试的植物油中,碘值最低的橄榄油显示出最高的共振电阻,而碘值最高的亚麻籽油显示出最低的共振电阻。植物油的共振电阻随其碘值的升高而降低。这些结果表明 QCM 可以有效地鉴定植物油。
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引用次数: 0
Studies on the Enzymatic Synthesis and Antioxidant Properties of Phenolic Acid Glycerols. 酚酸甘油酯的酶合成和抗氧化特性研究。
IF 1.6 4区 农林科学 Q3 CHEMISTRY, APPLIED Pub Date : 2024-11-01 Epub Date: 2024-10-17 DOI: 10.5650/jos.ess24065
Hong Li, Yanyan Li, Xuezhi Yin, Ziyi Li, Xintian Qiao, Huiling Mu, Ruiling Shen, Tao Wei

The potentially wide application of Phenolic acids (PAs) in industries was severely limited by their inadequate solubility and stability in polar/non-polar media. To overcome these limits, studies on the enzymatic esterification of PAs with glycerol were carried out to reach a yield of 95% of phenolic acid glycerols (PAGs) under the following reaction conditions: 1:150 molar ratio of PAs to glycerol; 25% of Lipozyme 435 relative to the weight of total substrates; 80°C, 500 rpm, 86.7 kPa and 10 h. Three resulting PAGs including caffeoyl glycerol (CG), feruloyl glycerol (FG), and p-hydroxycinnamoyl glycerol (p-HCG) were confirmed by MS, 1H NMR and 13C NMR. Among them, CG showed a comparative free radical scavenging ability to CA, indicating its potential use as a water-soluble antioxidant alternative to CA for food and cosmetic applications.

酚酸(PA)在极性/非极性介质中的溶解度和稳定性不足,严重限制了其在工业中的广泛应用。为了克服这些限制,我们对 PA 与甘油的酶法酯化进行了研究,在以下反应条件下,酚酸甘油(PAGs)的产量达到 95%:通过质谱、1H NMR 和 13C NMR 确认了生成的三种 PAG,包括咖啡酰甘油(CG)、阿魏酰甘油(FG)和对羟基肉桂酰甘油(p-HCG)。其中,阿魏酰甘油(CG)的自由基清除能力与阿魏酰甘油(CA)相当,这表明阿魏酰甘油(CG)可作为阿魏酰甘油(CA)的水溶性抗氧化剂替代品,应用于食品和化妆品领域。
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引用次数: 0
Prediction of Fatty Acid Intake from Serum Fatty Acid Levels Using Machine Learning Technique in Women Living in Toyama Prefecture. 利用机器学习技术从血清脂肪酸水平预测富山县女性的脂肪酸摄入量
IF 1.6 4区 农林科学 Q3 CHEMISTRY, APPLIED Pub Date : 2024-10-01 Epub Date: 2024-09-20 DOI: 10.5650/jos.ess24119
Hiroyuki Takeuchi, Sae Sakai, Akane Takahashi, Momoko Ejiri, Miyu Matsui, Yumiko Oota

Preventing lifestyle-related diseases requires understanding and managing the intake of total fats and specific types of fatty acids, especially trans fatty acids. There are several methods for measuring fat intake, each with its own strengths and limitations. Guidelines for nutritional epidemiology studies recommend employing objective biomarkers. This study aimed to estimate fatty acid intake based on serum fatty acid levels using multiple regression analysis and a machine learning technique, and to compare their accuracy. The subjects were healthy women aged 18 to 64 living in Toyama, Japan. A dietary survey to determine fatty acid intake was conducted using a 3-day dietary record completed by the participant. Blood samples were collected after an overnight fast, and serum was obtained through centrifugation. A total of 300 women participated in the study. The fatty acid levels in serum were determined using gas chromatography with a capillary column. Using multiple regression analysis and neural networks, the intakes of saturated, monounsaturated, n-6 polyunsaturated, n-3 polyunsaturated, and trans fatty acids from serum fatty acid levels were predicted. Significant correlations were observed between the intakes of the five classified fatty acids and the predicted intakes obtained from the multiple regression analysis (r = 0.39 - 0.49, p < 0.01). Significant correlations were also observed between the five classified fatty acid intakes and the intakes predicted by the neural network (r = 0.52 - 0.79, p < 0.01), and the correlation coefficient showed a significantly higher value than that predicted by the multiple regression analysis. These results suggest that serum fatty acid levels may be used as biomarkers to estimate the intake of fatty acids, including that of trans fatty acids, and that machine learning may be able to predict fatty acid intake with higher accuracy than multiple regression analysis.

预防与生活方式相关的疾病需要了解并控制总脂肪和特定类型脂肪酸的摄入量,尤其是反式脂肪酸。测量脂肪摄入量的方法有多种,每种方法都有自己的优势和局限性。营养流行病学研究指南建议采用客观的生物标志物。本研究旨在使用多元回归分析和机器学习技术,根据血清脂肪酸水平估算脂肪酸摄入量,并比较其准确性。研究对象是居住在日本富山的 18 至 64 岁的健康女性。我们使用受试者填写的 3 天饮食记录进行饮食调查,以确定脂肪酸摄入量。在一夜禁食后采集血液样本,并通过离心分离获得血清。共有 300 名女性参与了这项研究。使用毛细管柱气相色谱法测定血清中的脂肪酸水平。利用多元回归分析和神经网络,从血清脂肪酸水平预测饱和脂肪酸、单不饱和脂肪酸、n-6 多不饱和脂肪酸、n-3 多不饱和脂肪酸和反式脂肪酸的摄入量。五种分类脂肪酸的摄入量与多元回归分析得出的预测摄入量之间存在显著相关性(r = 0.39 - 0.49,p < 0.01)。五种分类脂肪酸的摄入量与神经网络预测的摄入量之间也存在显著相关性(r = 0.52 - 0.79,p < 0.01),相关系数明显高于多元回归分析预测的值。这些结果表明,血清脂肪酸水平可作为生物标记物来估计脂肪酸(包括反式脂肪酸)的摄入量,而机器学习预测脂肪酸摄入量的准确性可能高于多元回归分析。
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引用次数: 0
Effect of Surface Freezing of Sodium Hexadecyl Sulfate - Hexadecanol Mixed Adsorbed film on OW Emulsion Stability. 十六烷基硫酸钠-十六烷醇混合吸附膜表面冷冻对 OW 乳液稳定性的影响
IF 1.6 4区 农林科学 Q3 CHEMISTRY, APPLIED Pub Date : 2024-10-01 Epub Date: 2024-09-20 DOI: 10.5650/jos.ess24114
Hiroki Matsubara, Keigo Kato

The adsorbed film of Sodium Hexadecyl Sulfate (SHS) at the dodecane - water interface showed a first-order phase transition to a surface frozen monolayer upon cooling by the lateral van der Waals attraction between their hydrophobic tails and those of hexadecanol (C16OH) incorporated from the dodecane phase. The surface freezing transition of the SHS - C16OH monolayer was then utilized to stabilize an oil-in-water (OW) emulsion. The obtained results were compared to those examined previously for the cetyltrimethylammonium chloride (CTAC) - C16OH surface frozen monolayer. The main conclusion of this study was that the interfacial density of SHS significantly increased at the surface freezing by the cooperative adsorption with C16OH which gave rise to a higher surface freezing temperature (35°C) compared to CTAC (25°C). The formation of the surface freezing monolayer in the ambient temperature range could have a significant importance when it is applied to practical applications.

十二烷-水界面上的十六烷基硫酸钠(SHS)吸附膜在其疏水尾部与十二烷相中的十六烷醇(C16OH)尾部之间的侧向范德华吸引力作用下,在冷却时显示出向表面冻结单层的一阶相变。然后利用 SHS - C16OH 单层的表面冻结转变来稳定水包油(OW)乳液。获得的结果与之前研究的十六烷基三甲基氯化铵(CTAC)- C16OH 表面冷冻单层的结果进行了比较。这项研究的主要结论是,通过与 C16OH 的协同吸附,SHS 的界面密度在表面冷冻时显著增加,从而使表面冷冻温度(35°C)高于 CTAC(25°C)。在环境温度范围内形成表面冻结单层对实际应用具有重要意义。
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引用次数: 0
Effects of Different Manufacturing Processes on Thermal and Photo-oxidative Stability of Sesame Oil. 不同生产工艺对芝麻油热稳定性和光氧化稳定性的影响
IF 1.6 4区 农林科学 Q3 CHEMISTRY, APPLIED Pub Date : 2024-10-01 Epub Date: 2024-09-20 DOI: 10.5650/jos.ess24084
Halida Rahmania, Tomomi Nakanishi, Satomi Oi, Rika Onishi, Eiichiro Yamagami, Kazuyuki Yamane, Yurika Otoki, Shunji Kato, Kiyotaka Nakagawa

The roasting process of sesame oil is expected to alter its internal composition and stability under oxidation condition. Presumably, the effect of roasting may differ with oxidation conditions (i.e., thermal and photo-oxidation), but such studies have not been undertaken. To further evaluate this notion, several type of sesame oils (raw and refined as unroasted oil, and roasted oil) and rapeseed oils as comparison were subjected to thermal oxidation (120℃) and photo-oxidation (50,000 lx) for 5 and 10 hours. The result revealed that the roasting sesame oil exhibited good stability under thermal oxidation, possibly due to the change on antioxidant agents such as sesamol and Maillard products during the roasting process. In contrast, the refined sesame oil (unroasted) demonstrated high stability under photo-oxidation, indicating that the refining process has a more significant impact on the oxidative stability in sesame oil compared to the alterations in its components caused by the roasting process. Taken together, this study is the first to show that the roasting and refining processes of sesame oil alter its internal composition and show different variations in sesame oils' oxidative stability under thermal and photo-oxidation, which holds significance considering its global consumption.

芝麻油的焙烧过程预计会改变其内部成分和在氧化条件下的稳定性。据推测,焙烧的效果可能因氧化条件(即热氧化和光氧化)的不同而不同,但此类研究尚未开展。为了进一步评估这一观点,我们对几种芝麻油(生芝麻油、精炼芝麻油和焙烧芝麻油)和菜籽油进行了 5 小时和 10 小时的热氧化(120℃)和光氧化(50,000 lx)试验。结果表明,烘焙芝麻油在热氧化条件下表现出良好的稳定性,这可能是由于在烘焙过程中芝麻酚和 Maillard 产物等抗氧化剂发生了变化。相比之下,精炼芝麻油(未经烘焙)在光氧化条件下表现出较高的稳定性,这表明与烘焙过程中芝麻油成分的变化相比,精炼过程对芝麻油氧化稳定性的影响更为显著。综上所述,这项研究首次表明芝麻油的烘焙和精炼过程会改变其内部成分,并在热氧化和光氧化条件下显示出芝麻油氧化稳定性的不同变化。
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引用次数: 0
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Journal of oleo science
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