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CHEMISTRY & BIODIVERSITY · 2020 ·Vol. 17 ·期 8 ·e2000243 · IF 2.039

Investigation of the Effects of Squalene and Squalene Epoxides on the Homeostasis of Coenzyme Q10 in Rats by UPLC-Orbitrap MS

Wenjing Yu,Kaiju Sun,Liying Zhang,Xilin Wan,Changbao Chen,Rui Su,Yifei Liu,Hongfeng Wang,Hongmei Yang

Squalene has been used as a dietary supplement for a long history due to its potential cancer-preventive function. However, the mechanism has not been investigated in detail yet. Therefore, the aim of this study is to see if the plasma coenzyme Q10 (CoQ10) level will be altered by gavage of squalene and oxidosqualenes to rats. In the present work, a sensitive and simple high-performance analytical method based on ultra-high-performance liquid chromatography coupled with an Orbitrap mass spectrometry (UPLC-Orbitrap-MS) was developed for the quantification of CoQ10 in rat plasma. Coenzyme Q9 (CoQ9) was employed as the internal standard. CoQ10 was determined after acetonitrile-mediated plasma protein precipitation using UPLC-Orbitrap-MS in negative ion mode. Intragastric administration of squalene and the two squalene epoxides into rats once daily for several days elevated the level of CoQ10 in their plasma, but there was no significant difference between high-dose (286 mg/kg) and low-dose (143 mg/kg) groups. Intragastric administration of squalene once a day for 5 consecutive days and oxidosqualenes once a day for 3 consecutive days is necessary for reaching the steady-state level of CoQ10. Our present findings indicate that squalene and oxidosqualenes may be useful for stimulating the synthesis of CoQ10 in rats.

CAS / MDL: 937-14-4 303-97-9
研究领域: 药理学 · 分析化学 · 生物化学
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SEPARATION AND PURIFICATION TECHNOLOGY · 2016 · IF 3.299

Extraction of squalene from camellia oil by silver ion complexation

H. Xiao,Z. Yao,Q. Peng,F. Ni,Y. Sun,C.X. Zhang,Z.X. Zhong

Separation of squalene, a type of terpenoid hydrocarbons with important biological properties, from camellia oil by silver ion complexation was studied. We showed that the UV–visible absorption wavelength of squalene in AgNO 3 -methanol solution was obviously red-shifted, and the infra-red vibration wavelength of C C bond slightly decreased, indicating that complexation between squalene and Ag + took place. The distributions of squalene in AgNO 3 methanol solution/petroleum ether under different conditions were further investigated. We found that the fraction of squalene in AgNO 3 -methanol phase was enhanced with increased percentage of methanol and AgNO 3 concentration and decreased extraction temperature. The distribution coefficient of squalene was up to 7.87 under optimum extraction conditions with 70% methanol (v/v), 0.6   mol/L AgNO 3 , reaction time of 12   h, and at the temperature of 0   °C. Furthermore, under the optimum conditions, extraction of squalene from the unsaponifiable portion of camellia oil exhibited high selectivity with a raffinate rate and a back-extraction rate of 73.9% and 72.5%, respectively. The purity of extracted squalene was 37.8%, 108   times more concentrated than that in the starting material.

研究领域: 生物化学 · 分离技术
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Food Analytical Methods · 2021 ·Vol. 14 ·期 8 ·1567-1576 · IF 3.366

Simultaneous Determination of Tocopherols, Phytosterols, and Squalene in Vegetable Oils by High Performance Liquid Chromatography-Tandem Mass Spectrometry

Liu Shanshan,Hu Huiyu,Yu Yanpeng,Zhao Jiahui,Liu Lichun,Zhao Shanshan,Xie Jianhua,Li Chang,Shen Mingyue

Vegetable oil is one of the principal sources of minor bioactive substances such as tocopherol, phytosterol, and squalene. In order to obtain the distribution of these substances in vegetable oil, this study developed and validated high performance liquid chromatography-tandem mass spectrometry (HPLC-MS) method for the simultaneous analysis of tocopherols (α-, β-, γ-, and δ-tocopherol), phytosterols (β-sitosterol, stigmasterol, brassicasterol, and campesterol), and squalene in vegetable oils. An automatic gel permeation chromatography (GPC) system was used to remove triglycerides from oils, avoiding the heat treatment of traditional saponification. Method validation revealed the accuracy and reliability of this method. The current approach achieved the successful separation of β- and γ-tocopherol, which solved the problem of coelution and inaccurate quantification for β- and γ-tocopherol in previous study. Additionally, this method was applied to detect tocopherols, phytosterols, and squalene in 9 categories of vegetable oils.

研究领域: 食品科学 · 分析化学
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FOOD CHEMISTRY · 2019 · IF 5.399

1H NMR combined with PLS for the rapid determination of squalene and sterols in vegetable oils

Ting Shi,MengTing Zhu,XingYu Zhou,Xi Huo,You Long,XiangZhong Zeng,Yi Chen

Proton nuclear magnetic resonance ( 1 H NMR) combined with partial least squares (PLS) was developed for the rapid determination of squalene and sterols (brassicasterol, campesterol, stigmasterol and β-sitosterol) in 119 vegetable oils from 7 different species. The 1 H NMR spectra of these oil samples were correlated to the reference value determined by gas chromatography-mass spectrometry (GC–MS) method by PLS regression, using outlier removal, selection of input X-variables and data pretreatments. Auto-scaling (UV) was chosen as the best pre-processing for the PLS models of stigmasterol, β-sitosterol, and squalene. Pareto variance (Par) was more suitable for the PLS model of brassicasterol. The model for squalene was further improved by a reduced number of variables with variable importance for the projection (VIP) scores technique. The study demonstrated the potential application of NMR coupled with PLS as a rapid and nondestructive technique for the routine analysis of squalene and sterols in vegetable oils.

研究领域: 食品科学 · 分析化学
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Journal of Biobased Materials and Bioenergy · 2020 ·Vol. 14 ·期 5 ·657-663 · IF 1.126

Effect of Se Enrichment on Improving the Quality of Camellia Oil from Different Source Varieties

Liu Jie,Wu Lichao,Tan Yimin

Se-enriched camellia oil has received increasing attention because it can improve the Se intake of diet for Se deficiency areas and has a wide spectrum of biological effects. Six main cultivars of camellia oil in Guangxi, including Camellia oleifera cenxiruanzhi 2 (CR2), CR3, C. oleifera xianglin 4 (XL4), XL40, C. oleifera changlin 1 (CL1), and CL210, were selected for fertilization experiment to produce Se-enriched camellia oil and investigated the effect of Se enrichment on quality. The Se content in camellia oil of six varieties was significantly increased by Se fertilizer application. CR2 had the maximum Se content and raise ratio compared to CK, which was 0.87 mg kg−1 and fourfold, respectively. The Se contents in XL1, XL210, CR3, CL4, and CL40 improved by 2.14-, 2.77-, 3.58-, 2.56-, and 3.79-fold, respectively. Se fertilizer reduced the acid and peroxide values and increased the squalene and tocopherol contents. The acid value decreased by 38.29%–61.30%, the peroxide value decreased by 20.66%–61.79%, the tocopherol content increased by 7.76%–32.78%, and the squalene content increased by 13.53%–77.39%. The quality indices were significantly different among camellia oil varieties. Principal component analysis showed that CR2 obtained the highest score by comprehensive evaluation. Se fertilization, particularly for CR2 species, can significantly increase the contents of Se as well as functional components, such as squalene and tocopherol, and thus improve the quality of camellia oil

研究领域: 植物学 · 营养学 · 食品科学
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ANALYTICAL CHEMISTRY · 2025 · IF 6.7

A Facile Workflow for Sebum Fatty Acids and Squalene Identification via Advanced Lipidomic Methodologies

Lerong Qi,Xiangzi Li,Yachen Ren,Tingxiang Yang,Yang Guan,Dong Hao Wang,Zhen Wang

Sebum fatty acids and squalene are major components of skin secretions and play a critical role in the pathogenesis of dermatological conditions through their compositional alterations. Human sebum fatty acids are uniquely diverse in their chain length, double bond positions, and chain branching; squalene is a rare component of skin secretions with six double bonds. We introduce a facile workflow for the analysis of sebum fatty acids and squalene for elucidating their contribution to the state of skin health or disease using advanced mass spectrometric methods for qualitative and quantitative analyses. Sebum from dermatologically healthy individuals was extracted, and covalent adduct chemical ionization (CACI), electron ionization (EI), and Paternò–Büchi (PB) tandem mass spectrometry (MS/MS) techniques were employed for the identification of fatty acids with varying methyl branch and/or carbon–carbon double bond positions. A method for the full structural characterization of squalene via CACI tandem mass spectrometry was also developed. In sebum, we report for the first time unusual straight-chain polyunsaturated fatty acid isomers (n18:2n-7, n18:2n-3, n20:2n-12, and n20:2n-7), a series of previously unreported branched-chain saturated fatty acids with C19–C26, and a novel branched-chain monounsaturated fatty acid i15:1n-9. A total of 64 fatty acids were identified, exceeding the previous reports. Our study established a comprehensive qualitative and quantitative workflow for the analysis of sebum fatty acids and squalene, with the potential to advance dermatological research and clinical diagnostics.

研究领域: 皮肤病学 · 脂质组学 · 分析化学
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JOURNAL OF FOOD BIOCHEMISTRY · 2025 ·Vol. 2025 ·期 1 ·8349248 · IF 4.2

Tanshinone IIA Combined With Rutin and Squalene Improves Hyperlipidemia to Alleviate Atherosclerosis in New Zealand Rabbits Through Upregulation of the SREBP2/LDLR Pathway

Yuanjie Wu,Yuntian Zhang,Xike Wu,Ziyan Zhang,Junhui Shen,Nan Tian,Chunlei Fan

This study investigated the effects of tanshinone IIA combined with rutin and squalene (RTS) on atherosclerosis (AS) associated with hyperlipidemia and the underlying mechanisms. Female New Zealand rabbits were subjected to a hyperlipidemia and AS model. Treatment with RTS for 4 weeks reduced the weight, and some serum lipid levels include serum TC, serum TG, serum LDL-C. RTS also improved lesions of the liver and aorta. In vitro analyses showed that RTS significantly activated LDLR-mediated hepatic lipid endocytosis, but blocking LDLR activation with si-SREBP2 attenuated the therapeutic effect, which demonstrated that RTS can activate the SREBP2/LDLR pathway mediating liver clearance of blood lipids. This study highlights the therapeutic potential of RTS in hyperlipidemia and AS. As a convenient form of a combination drug, RTS has shown considerable potential in the improvement of hyperlipidemia combined with AS.

CAS / MDL: 9005-38-3
研究领域: 药理学 · 心血管病学 · 分子生物学
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Catalysts · 2023 ·Vol. 13 ·期 11 ·1392 · IF 3.9

Integrating Fermentation Engineering and Organopalladium Chemocatalysis for the Production of Squalene from Biomass-Derived Carbohydrates as the Starting Material

Cuicui Wu,Kaifei Tian,Xuan Guo,Yunming Fang

The transition from fossil resources to renewable biomass for the production of valuable chemicals and biobased fuels is a crucial step towards carbon neutrality. Squalene, a valuable chemical extensively used in the energy, healthcare, and pharmaceutical fields, has traditionally been isolated from the liver oils of deep-sea sharks and plant seed oils. In this study, a biochemical synergistic conversion strategy was designed and realized to convert glucose to squalene by combining fermentation technology in yeast with reductive coupling treatment of dienes. First, glucose derived from hydrolysis of cellulose was used as a renewable resource, using genetically engineeredSaccharomyces cerevisiaeas the initial biocatalyst to produce β-farnesene with a titer of 27.6 g/L in a 2.5 L bioreactor. Subsequently, intermediate β-farnesene was successfully converted to squalene through the organopalladium-catalyzed reductive coupling reaction involving the formation of Pd(0)L2species. Under mild reaction conditions, impressive β-farnesene conversion (99%) and squalene selectivity (100%) were achieved over the Pd(acac)2catalyst at a temperature of 75 °C in an ethanol solvent after 5 h. This advancement may provide insights into broadening squalene production channels and accessing the complex skeletons of natural terpenoids from biorenewable carbon sources, offering practical significance and economic benefits.Keywords:squalene;β-farnesene;fermentation technology;reductive coupling of dienes;Saccharomyces cerevisiae

研究领域: 生物化学 · 化学工程 · 微生物学
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Plant Stress · 2024 · IF 6.8

Identification of reference genes via real-time quantitative PCR for investigation of the transcriptomic basis of the squalene biosynthesis in different tissues on olives under drought stress

Haiyang Chi,Shasha Bai,Chenxiao Chen,Yuying Bao,Xiaoxin Qu,Shitao Sun,Jiangpeng Pan,Xiushi Yang,Chunsheng Hou,Yanchun Deng

Squalene plays a crucial role in plant growth, development, and stress tolerance. To select the best reference genes (RGs) for expression profile analysis of genes involved in squalene biosynthesis in olives under stress tolerance, the expression stability of 22 candidate RGs across four tissues (root, stem, leaf, and fruit) and five representative cultivars under drought stress was assessed using six methods. Our study showed that, ubiquitin-conjugating enzyme1 ( UBC1 ) and 60S ribosomal protein L18-2-like ( 60S ) were the most stable RGs across five different cultivars and various tissues. Additionally, elongation factor 1-alpha-like ( EF1-α2) and UBC1 were the most stable RG in olives under drought stress. UBC1 was the appropriate RG for further study, qPCR analysis showed that five certain genes involved in the squalene biosynthesis exhibited significant differential expression under varying conditions. Specially, the expression level of squalene synthase (SQS) in the leaves was highest, and HPLC analysis showed that squalene content was the highest in leaves. Likewise, the expression levels of SQS and farnesyl diphosphate synthase ( FPPS ) in the leaves of the cultivar Arbosana and Chelmsford Lal were significantly higher than those of the other cultivars, respectively, and HPLC analysis also showed that squalene content was highest in the two cultivars. Interestingly, the amount of squalene increased dramatically in olive under drought stress, as lupeol synthase ( LUPS ) was significantly up-regulated. To date, this study firstly provided the comprehensive analysis of RGs related to squalene biosynthesis in various cultivars and tissues of olives under drought stress.

CAS / MDL: 111-02-4
研究领域: 植物科学 · 分子生物学 · 胁迫生理学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2020 · IF 4.192

Metabolic Engineering of Saccharomyces cerevisiae To Overproduce Squalene

Tian Li,Guo-Song Liu,Wei Zhou,Min Jiang,Yu-Hong Ren,Xin-Yi Tao,Min Liu,Ming Zhao,Feng-Qing Wang,Bei Gao,Dong-Zhi Wei

Squalene has wide applications in the food and pharmaceutical industries. Engineering microbes to produce squalene is a promising alternative for traditional production approaches. In this study, squalene production was enhanced to 978.24 mg/L through stepwise overexpression of the enzymes that catalyze acetyl-CoA to squalene. Subsequently, to increase the activity of HMG-CoA reductase and alleviate the high dependence on NADPH, the HMG-CoA reductase (NADH-HMGR) from Silicibacter pomeroyi, highly specific for NADH, was introduced, which increased squalene production to 1086.31 mg/L. Native ethanol dehydrogenase ADH2 and acetaldehyde dehydrogenase ADA from Dickeya zeae were further overexpressed, which enhanced the capability to utilize ethanol for squalene synthesis and endowed the engineered strain with greater adaptability to high ethanol concentrations. Finally, a remarkable squalene production of 9472 mg/L was obtained from ethanol via carbon source-controlled fed-batch fermentation. This study will greatly accelerate the process of developing microbial cell factories for squalene production.

CAS / MDL: 111-02-4
研究领域: 生物技术 · 代谢工程 · 微生物生物技术
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Food Bioscience · 2025 · IF 5.9

Enhanced amelioration of Camellia Oil on Colitis with the supplementation of Squalene and α-Tocopherol

Jingyang Liu,Jihang Hou,Zhiyi Zhang,Yongkang Liu,Rong Liu,Zeyuan Deng,Ting Luo

Ulcerative colitis (UC) is a chronic, recurring gastrointestinal disease that not only threatens human health but also increases the risk of colon cancer. Camellia oil has potential for the treatment of colitis. However, bioactive compounds, namely squalene and α-tocopherol, vary greatly in Camellia oil from different regions, and their therapeutic efficacy in colitis varies. We therefore investigated the effect of Camellia oil with different concentrations of squalene and α-tocopherol on colitis. Our results showed that Camellia oil attenuated the weight loss, decreased disease activity index (DAI), increased colon length, improved colon histology in DSS-induced colitis in mice, and reduced the gene expression and serum concentrations of TNF-α and IL-6. Camellia oil supplemented with squalene (final concentration of 375 mg/kg of Camellia oil) and α-tocopherol (final concentration of 600 mg/kg of Camellia oil) had the most potent effects on the alleviation of colitis symptoms. In conclusion, the intake of Camellia oil relieved DSS-induced colitis, and the modulation of squalene and α-tocopherol contents in Camellia oil further impacted its efficacy, which provides a theoretical basis for the development of novel Camellia oil with potent therapeutic potential to lower the risk of colitis.

CAS / MDL: 64-17-5 9011-18-1
研究领域: 医学 · 营养学 · 药理学
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CATALYSIS COMMUNICATIONS · 2023 · IF 3.7

Purification of artemisinin precursor amorphadiene from microbial metabolites containing isomeride farnesene: Solid-Pd chemocatalysis of farnesene to squalene with high boiling point

Cuicui Wu,Pan Feng,Xuan Guo,Yunming Fang

Due to complex chemical mechanism of sesquiterpene synthases, amorpha-4, 11-diene (AD) from microbial fermentation contained isomeride β-farnesene (FA) with similar boiling point. For purifying AD, FA was converted to biofuel-valued squalene (SQ) with high boiling point using solid Pd catalysts. (NHT)OS-Pd catalysts resulted in FA conversion of >99.9% and SQ selectivity of >99.0% at 80 °C for 5 h. Moreover, this catalyst exhibited great stability and recycling performance. When (NHT)OS-Pd was applied to AD mixture, almost FA was converted to SQ and AD remained in the pre-reaction state. As SQ had a higher boiling point, AD was easily distilled out.

研究领域: 化学工程 · 生物技术 · 有机化学
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