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Sciadonic acid
MICROCHEMICAL JOURNAL · 2025 · IF 5.1

A rapid strategy to enrich high-purity sciadonic acid from Torreya grandis kernel oil using silver ion-loaded molecular imprinted polymers

Chengyu Jin,Siyuan Chen,Jue Ding,Qin Ye,Xianghe Meng

Sciadonic acid (SA, Δ5,11,14–20:3) is an unusual fatty acid found in Torreya grandis kernel oil with significant health benefits and functional value. However, obtaining high-purity SA from crude oil remains a challenge. In this study, we developed an efficient, eco-friendly, and selective method for SA enrichment using silver ion (Ag + )-loaded molecularly imprinted polymers (MIPs). Methacrylic acid (MAA) was selected as the functional monomer, with SA as the template molecule and AgNO 3 as the complexing agent. The polymerization was carried out using reversible addition-fragmentation chain transfer (RAFT)-modified Fe 3 O 4 @SiO 2 . Furthermore, adsorption studies revealed that the process followed the Langmuir isotherm model, while the adsorption kinetics were best described by the Pseudo-second-order model, with a maximum binding capacity of 97.04 mg/g. Then, Optimization experiments showed that the highest adsorption efficiency (84.62 %) was achieved using 20 mg of MIPs at 30 °C for 30 min. Desorption was most effective with n-hexane/acetic acid (9:1, v/v) for 8 h, yielding a desorption efficiency of 70.65 %. As a result, the final SA purity reached 93.11 %, with a recovery rate of 65.03 %. This novel Ag + -loaded MIPs strategy provides a rapid, selective, and environmentally friendly approach for SA enrichment, demonstrating the great potential for industrial application.

研究领域: 食品科学 · 生物化学
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JOURNAL OF FOOD COMPOSITION AND ANALYSIS · 2025 · IF 4.6

Mass spectrometry differentiation of sciadonic acid isomers and estimate of long-chain polyunsaturated fatty acid intake from fresh and processed duck eggs

Chuanshun Dai,Lerong Qi,Tingxiang Yang,Zhen Wang,Dong Hao Wang

Sciadonic acid, or 20:3(5Z,11Z,14Z), is an unusual polyunsaturated fatty acid (PUFA) found in certain gymnosperm nuts and marine invertebrates. However, no study has detected it in commonly consumed food items. This study analyzed the fatty acid compositions of fresh, salted, and preserved duck eggs thoroughly via gas chromatography coupled with covalent adduct chemical ionization mass spectrometry (GC/CACI-MS). A multiple reaction monitoring method was developed to specifically characterize three 20:3 isomers found in duck eggs. Sciadonic acid was quantified at 0.13 % and 0.07 % (wt/wt of total fatty acids) in fresh and processed duck eggs, respectively. The major n-3 PUFA is DHA, with average concentrations of 1.44 %, 0.79 %, and 0.98 % in fresh, preserved, and salted duck eggs, respectively. For an average Chinese individual, the daily intake of DHA and total long-chain n-3 PUFA from all types of duck eggs is estimated to be 7.6 mg/day and 10.6 mg/day, respectively.

CAS / MDL: 77-76-9
研究领域: 营养学 · 食品科学 · 分析化学
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JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE · 2024 · IF 3.3

Sciadonic acid ameliorates cyclophosphamide-induced immunosuppression by modulating the immune response and altering the gut microbiota

Lin Chen,Qihong Jiang,Shiwei Yao,Chenkai Jiang,Hongling Lu,Wenjun Hu,Shaofang Yu,Mingqian Li,Yongcai Feng,Chin Ping Tan,Xingwei Xiang,Guoxin Shen

BACKGROUND Cyclophosphamide (Cy) is a frequently used chemotherapeutic drug, but long-term Cy treatment can cause immunosuppression and intestinal mucosal damage. The intestinal mucosal barrier and gut flora play important roles in regulating host metabolism, maintaining physiological functions and protecting immune homeostasis. Dysbiosis of the intestinal flora affects the development of the intestinal microenvironment, as well as the development of various external systemic diseases and metabolic syndrome. RESULTS The present study investigated the influence of sciadonic acid (SA) on Cy-induced immunosuppression in mice. The results showed that SA gavage significantly alleviated Cy-induced immune damage by improving the immune system organ index, immune response and oxidative stress. Moreover, SA restored intestinal morphology, improved villus integrity and activated the nuclear factor κB signaling pathway, stimulated cytokine production, and reduced serum lipopolysaccharide (LPS) levels. Furthermore, gut microbiota analysis indicated that SA increased t beneficial bacteria ( Alistipes , Lachnospiraceae_NK4A136_group , Rikenella and Odoribacter ) and decreased pathogenic bacteria ( norank-f-Oscillospiraceae , Ruminococcus and Desulfovibrio ) to maintain intestinal homeostasis. CONCLUSION The present study provided new insights into the SA regulation of intestinal flora to enhance immune responses. © 2024 Society of Chemical Industry.

CAS / MDL: 16595-80-5
研究领域: 药理学 · 免疫学 · 微生物学 · 分子生物学
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BIOCHEMICAL ENGINEERING JOURNAL · 2023 · IF 3.9

Silver ion assisted urea complexation for the enrichment of sciadonic acid from Torreya fargesii kernel oil

Xianghe Meng,Jue Ding,Qin Ye

Sciadonic acid (SA), a unique polymethylene-interrupted polyunsaturated fatty acids from Torreya grandi , drew increasing attention due to its multi healthy function. The one-step preparation for high purity SA by using urea crystallization method assisted by silver ion was investigated. Silver(I) tied the triunsaturated SA to stay in solution, while urea crystallization drawn the saturated and monounsaturated oleic acid into its channel to form complexes, these bidirectional enrichment effects increased the purity of SA to 89.3 % from initial 9.95 % with SA recovery of 32 %. The 1:1 silver ion/SA molar ratio produced the optimal purification performances. Raman spectra analysis of various molar ratio silver complex with SA supported this finding. Optimization on inclusion parameters suggested that urea concentration of 40 %, the mass ratio of fatty acid ethyl ester to urea is 1:4, cool rate at 0.5 °C /min were fit. In addition, the recycling of silver ion, urea and ethanol was performed over four cycles, and the results showed that the purity and recovery of SA among cycles were stable, and the purification performances were acceptable. Therefore, the developed silver ion assisted urea complexation strategy for the preparation of high purity SA is simple, economic, effective and has the potential for application on scale.

研究领域: 植物化学 · 食品科学 · 分析化学
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FOOD CHEMISTRY · 2026 · IF 10.4

Enzymatic preparation of a sciadonic acid-enriched phospholipid fraction and its in-vitro lipid-accumulation-inhibitory effect

Qin Ye,Siyuan Chen,Shuyi Wang,Xianghe Meng

Ionic-liquid-assisted transesterification produced SCA-enriched phospholipids. • Novozym 435-[C4MIM]Tf 2 N system favored SCA incorporation. • Optimized conditions achieved 25.96% SCA incorporation in purified PC. • SCA-enriched phospholipids inhibited lipid accumulation in HepG2 cells. Sciadonic acid (SCA) is an unusual Δ5 polyunsaturated fatty acid reported to affect lipid metabolism and inflammation. Because phospholipid forms of bioactive fatty acids may improve bioavailability and modify biological activity, this study prepared SCA-enriched phospholipid fractions. SCA ethyl ester (SCA-EE) derived from Torreya grandis seed oil was transesterified with phosphatidylcholine (PC) in [C₄MIM]Tf₂N using Novozym 435. Under optimized conditions (PC/SCA-EE molar ratio 1:7, 20% enzyme loading, 55 °C, 24 h), SCA incorporation into the purified PC fraction reached 25.96%, as determined by GC/FID. Molecular docking and FTIR were used to investigate possible lipase–substrate interactions and lipase secondary-structure changes in ionic-liquid systems, respectively. In an oleic-acid-induced HepG2 model, the SCA-enriched phospholipid fraction inhibited intracellular lipid accumulation more strongly than PC and SCA-EE at the tested mass doses. These results support ionic-liquid-assisted enzymatic transesterification as a feasible laboratory-scale approach for preparing SCA-enriched phospholipid fractions with improved lipid-accumulation-inhibitory activity. Download: Download high-res image (245KB) Download: Download full-size image

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BIOCHEMICAL ENGINEERING JOURNAL · 2025 · IF 3.8

An Ag+-assisted high-speed countercurrent chromatography and column chromatography for effective separating sciadonic acid from Torreya grandis oils

Meng Xianghe,Wang Shuyi,Lu Yuanchao,Nie Xiaohua,Ye Qin

Sciadonic acid (△5,11,14–20:3, SCA) is a rare versatile non-methylene-interrupted polyunsaturated fatty acid. To prepare high purity SCA from Torreya oils with 8.04 % purity, Ag + -assisted high-speed countercurrent chromatography (HSCCC) combined with urea complexation (UC) or argentation column chromatography (CC) was investigated. Results showed that n -hexane: acetonitrile (1:1, v/v) was suitable mobile phase for HSCCC, and SCA with purity of 23.74 % and recovery of 61.74 % (SCA purity>20 %) were obtained. When the Ag + addition was 0.50 %, one round of Ag + -HSCCC resulted in a recovery of SCA up to 95.38 % with purity around 21 %. It was believed that the enhanced performance originated from the reversible complexes between Ag + and C C in SCA through π-s * and d-π* bonds. Starting with low purity SCA of 8.04 %, HSCCC (23.74 %), UC (62.67 %), or Ag + -CC (60.41 % ) alone failed to produce SCA with high-purity (>90 %). However, Ag + -HSCCC combined with Ag + -UC or Ag + -CC yielded SCA with purities of 76.21 % and 97.74 %, and overall recovery of 21.38 % and 19.31 %, respectively. Thus, Ag + -HSCCC was an efficient method for the pre-enrichment of SCA, which could effectively facilitate coupling with UC, Ag + -CC or other PUFA purification techniques, resulted in significant improved purification performances.

研究领域: 植物化学 · 分离技术
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INDUSTRIAL CROPS AND PRODUCTS · 2019 · IF 4.191

Positional distribution of Δ5-olefinic acids in triacylglycerols from Torreya grandis seed oil: Isolation and purification of sciadonic acid

Xianghe Meng,Dan Xiao,Qin Ye,Xiaohua Nie,Jiasheng Wu,Lili Song

In recent years, in concern for human health, increasing attention was focused on sciadonic acid (SA), a unique Δ5-olefinic acid. Torreya grandis ( T. grandis ), a large, evergreen coniferous tree, whose seed yields rare and is known for a high level of SA. Triacylglycerols (TAGs) from the seeds of four different T. grandis varieties (Yuanfei, Xifei, Xiangyafei, and Zhimafei), were analyzed with respect to fatty acid profiles and positional distributions. The results indicated that SA represented the majority of the Δ5-olefinic acids in T. grandis seed oil. Irrespective of the variety, SA was naturally abundant at the sn-3 position of TAGs where they accounted for approximately 7.52%–12.00%. Based on this specific characteristic of Δ5-olefinic acids, T. grandis seed oil was subjected to a two-step enrichment process involving specific lipase-catalyzed ethanolysis and urea complexing. The content of SA in the fatty acid ethyl ester was increased to 80.14% from an initial value of 9.95%. These results suggested that the developed enrichment strategy was simple and effective in concentrating SA, and had the potential for commercial application.

研究领域: 植物学 · 生物化学
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Frontiers in Nutrition · 2022 · IF 6.59

Antidiabetic effect of sciadonic acid on type 2 diabetic mice through activating the PI3K-AKT signaling pathway and altering intestinal flora

Chen Lin,Jiang Qihong,Lu Hongling,Jiang Chenkai,Hu Wenjun,Yu Shaofang,Xiang Xingwei,Tan Chin Ping,Feng Yongcai,Zhang Jianfang,Li Mingqian,Shen Guoxin

Type 2 diabetes mellitus (T2DM) is a metabolic disease characterized by hyperglycemia. The aim of this work was to investigate the effect of sciadonic acid (SA) on disorders of glucolipid metabolism and intestinal flora imbalance and to further investigate its potential molecular mechanism of anti-diabetes. The experimental data indicated that SA could alleviate hyperlipidemia, insulin resistance, oxidative stress, the inflammatory response, repair liver function damage, and promote glycogen synthesis caused by T2DM. SA could also activate the PI3K/AKT/GLUT-2 signaling pathway, promote glucose metabolism gene expression, and maintain glucose homeostasis. Furthermore, 16S rRNA analysis revealed that SA could reduce the Firmicutes/Bacteroidota (F/B) ratio; promote norank_f__Muribaculaceae, Allobaculum, Akkermansia, and Eubacterium_siraeum_group proliferation; increase the levels of major short-chain fatty acids (SCFAs), such as acetic acid, propionic acid, and butyric acid; and maintain the homeostasis of the intestinal flora. In conclusion, these results suggested that SA could reshape the structural composition of intestinal microbes, activate the PI3K/AKT/GLUT2 pathway, improve insulin resistance, and decrease blood glucose levels.

研究领域: 药理学 · 内分泌学 · 微生物学 · 代谢学
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