Co-reporter:Xiaoxu Wang, Suyuan Tao, Peixu Cong, Yuming Wang, Jie Xu, Changhu Xue
Journal of Functional Foods 2017 Volume 33(Volume 33) pp:
Publication Date(Web):1 June 2017
DOI:10.1016/j.jff.2017.03.030
•The neuroprotection of sea urchin gangliosides was studied in PC12 and AD mice.•SU-GLSs exhibited a dose-dependent and structure-selective neuroprotection in PC12.•SU-GLSs resulted in a dramatic reduction of Aβ1-40 and Aβ1-42 in SAMP8 mice.•SU-GLSs resisted AD via ameliorating neurite loss and mitochondrial apoptosis.Gangliosides (GLSs), abundant in the mammalian brain, have been shown to affect neuronal plasticity and neurodegenerative diseases, especially Alzheimer’s disease. However, the biological activity and neuroprotective mechanism have not yet been established for sea urchin GLSs (SU-GLSs). Herein, we evaluated the neuroprotective effect of Strongylocentrotus nudus GM4(1S), GD4(1S), GD4(2A), and GD4(2G) in Aβ25-35-induced PC12 cells and in vivo using a GLSs mixture administered to SAMP8 mice. It was established that the pre-treatment of SU-GLSs decreased the loss of cell viability and the levels of Aβ1-40 and Aβ1-42 in the hippocampus significantly, and relieved the cognitive deficiency of SAMP8 mice. Mechanistic studies found that SU-GLSs down regulated the expression of Bax, Caspase-3, and Caspase-9, while it upregulated the expression of Bcl-2, synaptophysin, and GAP-43 significantly. Thus, SU-GLSs promoted resistance to AD in a dose-dependent and structure-selective manner, probably via reducing the loss of neurites and blocking the mitochondrial apoptosis pathway.
Co-reporter:Qiping Zhan;Xiong Gui;Fei Wang;Peng Yu;Meihui Zhao;Jingfeng Wang
Food & Function (2010-Present) 2017 vol. 8(Issue 3) pp:1094-1104
Publication Date(Web):2017/03/22
DOI:10.1039/C6FO01346E
Osteoporosis is a common disease in the elderly, which is related to fracture healing delay. In this study, the effects of treatment with sialoglycoprotein isolated from the eggs of Gadus morhua (Gm-SGP) on tibial fracture healing in ovariectomized (OVX) osteoporotic female C57BL/6J mice for 56 days post-fracture were investigated. The result showed that Gm-SGP treatment significantly increased serum angiogenic factors and bone formation markers on day 5 and 11 post-fracture when compared with the OVX group. In addition, histological results in the Gm-SGP group showed a stronger endochondral ossification, a stronger bony consolidation and a stronger bony callus remodeling capability on day 11, 24 and 35 post-fracture, respectively, in comparison with the OVX group. Meanwhile, micro-computerized tomography revealed that the Gm-SGP group had stronger bony callus remodeling capability as evidenced by higher BV/TV and Tb.N but lower Tb.Sp and shorter lengths of callus maximum cross section than the OVX group on day 24 post-fracture. Besides, the tibial callus bending stiffness was significantly enhanced in the Gm-SGP group as compared with the OVX group on day 56 post-fracture. Moreover, gene expression suggested that Gm-SGP promoted vascular invasion and endochondral ossification on day 11 post-fracture as well as bone formation on day 11 and 24 post-fracture via up-regulating the expression of angiogenesis factors (including VEGF, PDGF and Ang1), entochondrostosis factors (including Col2a1, Aggrecan, Col10a1 and MMP-13) and osteogenesis markers (including Col1a1, BMP-2 and OCN). This research suggests that Gm-SGP significantly improve fracture healing which is delayed by OVX-induced osteoporosis. The present study may contribute to providing important implications for the utilization of Gm-SGP from fish eggs as a functional food to enhance fracture healing.
Co-reporter:Min Wen, Lin Ding, Lingyu Zhang, Miaomiao Zhou, Jie Xu, Jingfeng Wang, Yuming Wang, Changhu Xue
Journal of Functional Foods 2016 Volume 22() pp:417-430
Publication Date(Web):April 2016
DOI:10.1016/j.jff.2016.02.004
•DHA-PS has more significant effect on Aβ-induced cognitive deficiency than DHA-PC.•.DHA-PLs improved Aβ-induced brain dysfunction uncoupled with brain DHA increase.•The mechanism of DHA-PLs involved in ameliorating Aβ induced oxidative stress, inflammation cascade and Tau pathology.•The effect of DHA-PLs on Aβ-induced cognitive deficiency is closely related with the polar group of phospholipid.Neurotoxicity of amyloid β (Aβ) plays an important role in Alzheimer's disease (AD) pathogenesis. In the present study, we investigated the comparative effects of docosahexaenoic acidphosphatidylcholine (DHA-PC) and docosahexaenoic acid-phosphatidylserine (DHA-PS) on Aβ-induced AD rats and studied further protective mechanisms underlying their effects. The administration of DHA-PC and DHA-PS (300 mg/kg, i.g., 27 days) had no effect on brain DHA levels but significantly improved Aβ-induced cognitive deficiency. Further mechanism research indicated that both DHA-PC and DHA-PS alleviated Aβ-induced neurotoxicity including oxidative stress, apoptosis, the neuroinflammation cascade, and hyper-phosphorylated tau. These results suggest that DHA-PC and DHA-PS represent a potential novel therapeutic candidate for the treatment of neurodegenerative diseases such as AD. Such an effect uncoupled with an increase in brain DHA but has an intimate relationship with the phospholipid polar groups, and DHA-PS has a particular advantage.
Co-reporter:Min Wen, Jie Xu, Lin Ding, Lingyu Zhang, Lei Du, Jingfeng Wang, Yuming Wang, Changhu Xue
Journal of Functional Foods 2016 Volume 24() pp:537-548
Publication Date(Web):June 2016
DOI:10.1016/j.jff.2016.04.034
•This is the first study to demonstrate the protective effect of EPA-PL on Aβ-induced cognitive deficiency in AD model rats.•EPA-PL improved Aβ-induced brain dysfunction uncoupled with brain DHA increase.•The mechanism of EPA-PL involved in ameliorating Aβ-induced oxidative stress, inflammation and hyper-phosphorylated Tau.Abundant studies have proven that the protective effects of omega-3 polyunsaturated fatty acids enriched phospholipids (n-3 PUFA-PLs) mainly derived from fish roe and Antarctic krill have beneficial effects on cognition. However, the n-3 PUFA-PLs are usually a mixture of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) enriched phospholipids. Hence, the effects of EPA-PLs alone on cognitive deficiency are still unclear. In the present study, we obtained almost pure EPA-PLs (EPA:DHA = 47.9:2.08) from the sea cucumber, Cucumaria frondosa, and investigated its effects on Aβ-induced cognitive impairment in rats. Administration of EPA-PLs (150 and 300 mg/kg⋅day, i.g., 27 days) did not increase brain DHA but significantly improved Aβ-induced cognitive deficiency. Further mechanism research indicated that EPA-PLs alleviated Aβ-induced neurotoxicity including oxidative stress, apoptosis, neuro-inflammation cascade, and hyper-phosphorylated tau in a dose-dependent pattern. These findings first suggest that EPA-PLs could also improve Aβ induced cognitive deficiency in a similar mechanism with DHA-PLs.
Co-reporter:Yanjun Liu;Qingxin Zhou;Jie Xu;Yong Xue
Environmental Geochemistry and Health 2016 Volume 38( Issue 1) pp:111-122
Publication Date(Web):2016 February
DOI:10.1007/s10653-015-9689-9
The objective of this study is to investigate the levels, inter-species-specific, locational differences and seasonal variations of vanadium in sea cucumbers and to validate further several potential factors controlling the distribution of metals in sea cucumbers. Vanadium levels were evaluated in samples of edible sea cucumbers and were demonstrated exhibit differences in different seasons, species and sampling sites. High vanadium concentrations were measured in the sea cucumbers, and all of the vanadium detected was in an organic form. Mean vanadium concentrations were considerably higher in the blood (sea cucumber) than in the other studied tissues. The highest concentration of vanadium (2.56 μg g−1), as well as a higher degree of organic vanadium (85.5 %), was observed in the Holothuria scabra samples compared with all other samples. Vanadium levels in Apostichopus japonicus from Bohai Bay and Yellow Sea have marked seasonal variations. Average values of 1.09 μg g−1 of total vanadium and 0.79 μg g−1 of organic vanadium were obtained in various species of sea cucumbers. Significant positive correlations between vanadium in the seawater and Vorg in the sea cucumber (r = 81.67 %, p = 0.00), as well as between vanadium in the sediment and Vorg in the sea cucumber (r = 77.98 %, p = 0.00), were observed. Vanadium concentrations depend on the seasons (salinity, temperature), species, sampling sites and seawater environment (seawater, sediment). Given the adverse toxicological effects of inorganic vanadium and positive roles in controlling the development of diabetes in humans, a regular monitoring programme of vanadium content in edible sea cucumbers can be recommended.
Co-reporter:Yanchao Wang;Yaoguang Chang;Li’ang Yin;Yong Xue
Food and Bioprocess Technology 2016 Volume 9( Issue 4) pp:621-627
Publication Date(Web):2016 April
DOI:10.1007/s11947-015-1658-x
Antarctic krill (Euphausia superba) offers a high potential for development of innovative food products due to its large reserves and satisfied nutritional values. Defatted krill powder by-product generates from the process of krill oil, which is rich in various types of amino acids. This study aimed at recovering tyrosine from defatted krill by-product through enzymatic hydrolysis. Defatted krill by-product was hydrolyzed with three types of protease under optimum conditions with different incubation time. Free tyrosine dissociated from protein through hydrolysis by trypsin and was detected in the protein hydrolysates. Content of tyrosine increased with the increasing of incubation time till 5 h. Tyrosine extract contained 6.43 mg/kg fluorine and over 95 % of tyrosine, which demonstrated its high purity and safety. Tyrosine extract showed rod-shaped microstructure through scanning electron microscope analysis. Crystalline structure and thermal properties of tyrosine extract agreed well with those of l-tyrosine standard. During this process, both tyrosine of high purity and bioactive peptide products were obtained.
Co-reporter:Yanchao Wang, Ruo Wang, Yaoguang Chang, Ying Gao, Zhaojie Li, Changhu Xue
Food Chemistry 2015 Volume 188() pp:170-176
Publication Date(Web):1 December 2015
DOI:10.1016/j.foodchem.2015.04.126
•Protein isolate was effectively recovered from defatted Antarctic krill byproducts.•This protein demonstrated its excellent nutritional values and good solubility.•Dispersions of this protein generated self-supported gels without additives.•Protein gels displayed a thermo-reversible behavior depending on hydrogen bonds.•Network strength of protein gels was strongly dependent on protein concentrations.Protein isolate was prepared from defatted Antarctic krill (Euphausia superba) byproducts by 0.1 M NaOH extraction. Maximum yield of krill protein isolate reached 28.66% by precipitation at pH 4.6. Krill protein isolate demonstrated its excellent nutritional values through amino acid composition and in vitro digestibility. Thermal transition of krill protein isolate was determined by differential scanning calorimetry measurement. Extrapolated values of glass transition temperature (Tg) and denaturation temperature (Td) of krill protein isolate were 33.8 °C and 80.3 °C when the heating rate was 2 °C/min. Dispersions of krill protein isolate generated self-supported gels at concentrations above 100 g/L without the addition of salt or other additives. A noticeable enhancement of gel strength was induced through cooling. Gels with krill protein isolate displayed a thermo-reversible behavior under repeating heating/cooling cycles, which was primarily due to the formation and disruption of hydrogen bonds. Network strength of protein gels was strongly dependent on protein concentrations.
Co-reporter:Pei-Xu Cong, Rui-chang Gao, Chang-Hu Xue, Zhao-Jie Li, Hong-Wei Zhang, Muhammad Naseem Khan, Yong Xue, Tatsuya Sugawara, Jie Xu
Food Chemistry 2015 Volume 166() pp:473-478
Publication Date(Web):1 January 2015
DOI:10.1016/j.foodchem.2014.06.028
•The paper demonstrated the identification of sia 2-6 hexose by ESI-MS/MS.•The cleavage pathway of sulfated sialic acid was proposed.•The retention versus ceramide carbon numbers were fitted to exponential equations.Sea urchin gangliosides have been proved to contain neuritogenic activities, which related to their molecular compositions. This study reports a method utilizing reversed-phase chromatography coupled to mass spectrometry for structure investigation and molecular species determination of the monosialogangliosides from sea urchin Strongylocentrotus nudus. Two types of sulfated and nonsulfated monosialogangliosides were isolated from the sea urchin ovary. In MS2 spectra of both nonsulfated monosialoganglioside and sulfated monosialoganglioside, 2-6 linked sialic acids were identified by the characteristic fragments of 0,4A2-CO2 and 0,2A1. Fragment ions at m/z 139.1 and m/z 169.1 of nonsulfated monosialoganglioside might be characteristic for 8-sulfated sialic acid residue. Retention time of the molecules was effectively used in the characterization of unknown molecules, and molecules that differ in mass by only 0.04 Da were easily differentiated.
Co-reporter:Guanghua Xia, Shanshan Wang, Min He, Xiaochun Zhou, Yanlei Zhao, Jingfeng Wang, Changhu Xue
Journal of Functional Foods 2015 Volume 15() pp:137-150
Publication Date(Web):May 2015
DOI:10.1016/j.jff.2015.03.021
•Anti-osteoporotic activity of Ca-SGP is reported for the first time.•Ca-SGP promoted osteogenesis.•Ca-SGP increased OPG/RANKL ratio in MC3T3-E1 cells and bilateral ovariectomized rats.•Ca-SGP improved tibia BMD of osteoporotic rats induced by bilateral ovariectomy.•Ca-SGP is a novel and significant functional factor for the treatment of osteoporosis.The anti-osteoporotic activities of a sialoglycoprotein isolated from the eggs of Carassius auratus (Ca-SGP). Ca-SGP was composed of 14.33% protein, 62.81% hexose, and 19.72% N-acetylneuraminic acid (Neu5Ac). In vitro experimental results showed that Ca-SGP significantly increased MC3T3-E1 pre-osteoblastic cells' proliferation activities, promoted cell differentiation and mineralization as evidenced by increasing the contents or activities of major markers, i.e. collagen type I (COL I), osteocalcin (OCN), alkaline phosphatase (ALP) and bone nodules. Ca-SGP significantly augmented protein expressions and secretions of bone morphogenetic protein 2 (BMP-2) and osteoprotegerin (OPG), meanwhile, decreased that of receptor activator of nuclear factor κB ligand (RANKL). In vivo experimental data further revealed that Ca-SGP significantly reduced bone turnover rates, increased serum OPG/RANKL ratio and enhanced tibia bone mineral density (BMD) in the model rats of ovariectomized (OVX)-induced osteoporosis. These results suggest that Ca-SGP could improve osteoporosis by promoting osteogenesis and inhibiting bone resorption via increasing OPG/RANKL ratio, which indicates that Ca-SGP is a potential candidate functional factor for osteoporosis prevention.
Co-reporter:Hui Xu, Fei Wang, Jingfeng Wang, Jie Xu, Yuming Wang and Changhu Xue
Food & Function 2015 vol. 6(Issue 7) pp:2396-2404
Publication Date(Web):03 Jun 2015
DOI:10.1039/C5FO00273G
Both adipocyte hypertrophy and hyperplasia lead to obesity. Here, we isolated cerebrosides from the sea cucumber Cucumaria frondosa (CFC) and examined its anti-adipogenic activity in vitro. CFC inhibited the lipid accumulation of 3T3-L1 cells and suppressed PPARγ and C/EBPα expressions, proving its anti-adipogenic activity. Furthermore, CFC suppressed lipogenesis in mature adipocytes. The WNT/β-catenin pathway acts as an anti-adipogenic factor. CFC enhanced β-catenin expression, promoted its nuclear translocation and up-regulated the expression of CCND1 and c-myc, two target genes of β-catenin. Moreover, after cells were treated with the β-catenin inhibitor 21H7, β-catenin nuclear translocation and transcription activity can be recovered by CFC. These findings suggested that CFC promoted the activation of the WNT/β-catenin pathway. Besides, CFC enhanced the expressions of Fz1, LRP5 and LRP6, while it had no effect on the expressions of Wnt10b and GSK3β. These findings indicated that CFC exhibits anti-adipogenic activity through enhancing the activation of the WNT/β-catenin pathway, which was mediated by FZ and LRPs.
Co-reporter:Shiwei Hu, Jingfeng Wang, Hui Xu, Yuming Wang, Zhojie Li, Changhu Xue
Journal of Functional Foods 2014 Volume 7() pp:517-526
Publication Date(Web):March 2014
DOI:10.1016/j.jff.2014.01.004
•Repair of pancreatic islets by Cf-CHS are reported for the first time.•Cf-CHS inhibited hyperglycemia induced-pancreatic islets apoptosis.•Cf-CHS blocked cytochrome c release to cytoplasm from mitochondria.•Inactivation of mitochondrial pathway caused the inhibition of apoptosis by Cf-CHS.•Cf-CHS is a novel and significant functional factor for insulin resistant therapy.Hyperglycaemia can induce pancreatic islets apoptosis. We previously found that fucosylated chondroitin sulphate from Cucumaria frondosa (Cf-CHS) exhibited anti-hyperglycaemic effects; however, its effects on pancreatic islets are lacking. This study investigated the effects of Cf-CHS on inhibition pancreatic islets apoptosis in high-fat high-sucrose diet (HFSD)-induced insulin resistant mice for 19 weeks. Results showed that Cf-CHS significantly repaired HFSD-injured pancreatic islets, decreased blood glucose, insulin, TNF-α levels, and increased adiponectin level. Cf-CHS significantly reduced Bid, Bax, cytochrome c, caspase 9, and caspase 3 mRNA expressions, and increased Bcl-2 and Bcl-xL mRNA expressions. Cf-CHS also caused significant down-regulation of t-Bid, Bax, cytochrome c in cytoplasm, caspase 9, and cleaved-caspase 3 proteins, and up-regulation of Bcl-2 and Bcl-xL proteins. Furthermore, Cf-CHS enhanced the effects of rosiglitazone (RSG). These indicate that Cf-CHS inhibits pancreatic islets apoptosis via inhibition mitochondrial pathway. These findings may provide a dietary intervention hyperglycaemia-induced pancreatic islets apoptosis.
Co-reporter:Xiaofang Liu;Jie Cui;Zhaojie Li;Jie Xu;Jingfeng Wang;Yuming Wang
European Journal of Lipid Science and Technology 2014 Volume 116( Issue 3) pp:255-265
Publication Date(Web):
DOI:10.1002/ejlt.201300407
Recent reports have shown that n-3 PUFA-enriched phospholipids have various beneficial effects. The proportion of DHA and eicosapentaenoic acid (EPA) in the phospholipids might affect their biological functions. In the present study, marine DHA-enriched phospholipids (DHA-PL) and EPA-enriched phospholipids (EPA-PL) were administered to high fat (HF) diet-induced obese C57BL/6J mice for 8 weeks to compare their effects on obesity-related metabolic disorders. DHA-PL and EPA-PL significantly decreased epididymal and perirenal adipose tissue weights, reduced blood pressures and lowered serum and hepatic triacylglycerol levels in HF diet-induced obese mice. Serum insulin, MCP-1 and IL-6 levels were also efficiently reduced by treatment with DHA-PL and EPA-PL. The anti-obesity and lipid-lowering effects of EPA-PL were superior to DHA-PL, while DHA-PL exhibited better anti-hypertension effects than EPA-PL. The effects of DHA-PL and EPA-PL on glucose intolerance and inflammation were basically equivalent. DHA-PL and EPA-PL up-regulated genes involved in insulin-sensitizing actions in the adipose tissue and suppressed hepatic SREBP-1c mediated lipogenesis. EPA-PL also significantly activated PPARα mediated fatty acid β-oxidation in the liver. These results indicate that DHA-PL and EPA-PL could efficaciously alleviate obesity-related metabolic disorders but the ameliorative degree and regulatory mechanisms are not identical.
Practical applications: This investigation would be useful in the selective development of functional foods containing DHA-PL or EPA-PL contributing to the prevention and treatment of chronic metabolic disease in humans. The study also showed the chemical compositions of phospholipids fractions of squid (Sthenoteuthis oualaniensis) egg and sea cucumber (Cucumaria frondosa) that may be useful for further studies.
Co-reporter:Shiwei Hu, Guanghua Xia, Jingfeng Wang, Yuming Wang, Zhaojie Li, Changhu Xue
Journal of Functional Foods 2014 10() pp: 128-138
Publication Date(Web):
DOI:10.1016/j.jff.2014.05.012
Co-reporter:QIAO-MING LOU;YU-MING WANG;CHANG-HU XUE
Journal of Food Biochemistry 2013 Volume 37( Issue 3) pp:296-301
Publication Date(Web):
DOI:10.1111/j.1745-4514.2011.00631.x
ABSTRACT
Analyses of lipid profile and fatty acid compositions of muscle and viscera of two commercially cultured abalone, namely Haliotis discus hannai Ino and Haliotis diversicolor Reeve, have been carried out. The total lipid levels of the viscera of both abalone were much higher than those of muscle. Phospholipids were the predominant lipid components in muscle, whereas triacylglycerol in viscera. The major fatty acids identified in muscle and viscera were C16:0, C18:0, C20:4n–6, C20:5n–3 and C22:5n–3. Polyunsaturated fatty acids (PUFAs) accounted for over 40% of total fatty acids, and C20:4n–6 and C20:5n–3 were the most abundant PUFAs. Moreover, different fatty acid compositions were found between the muscle and viscera. Compared with muscle, viscera contained higher percentage of 4,8,12-trimethyltridecanoic acid and C18-PUFA, but lower percentage of C22-PUFA and dimethyl acetals. This study would increase awareness of the nutritional value of these two abalone and also contribute some important information to abalone aquaculture.
PRACTICAL APPLICATIONS
Haliotis discus hannai Ino and Haliotis diversicolor Reeve are the main commercially farmed species of abalone and have become the most important species of molluscan mariculture in China and occupied the important position in terms of commercial value among farmed molluscan products. This study analyzed the lipid profile and fatty acid compositions of muscle and viscera of the above two abalone species. The results would provide some useful nutrition information for the consumption and aquaculture of abalone. Meanwhile, the viscera of abalone are rich in total lipids and polyunsaturated fatty acid, indicating that the viscera would have great potential of exploitation and comprehensive utilization in lipids.
Co-reporter:Hongbo Cui;Yong Xue;Wei Su
Journal of Food Science and Technology 2013 Volume 50( Issue 6) pp:1137-1143
Publication Date(Web):2013 December
DOI:10.1007/s13197-011-0430-0
Three water-activity-lowering agents (composite phosphate, sorbitol and glycerol) were used to develop a kind of shelf-stable, ready-to-eat (RTE) shrimp. Formula of water-activity- lowering agents was optimized by response surface methodology (RSM) using a central composite design. Model equation was proposed with regard to the contents of composite phosphate (X1), sorbitol (X2) and glycerol (X3) : \( Y = {1}.000{4} - 0.{5851}{{\text{X}}_1} - 0.0{322}{{\text{X}}_2} - 0.0{243}{{\text{X}}_3} + 0.0{167}{{\text{X}}_1}{{\text{X}}_2} + 0.0{156 }{{\text{X}}_1}{{\text{X}}_3} + {1}.0000 \times {1}{0^{ - {3}}}{{\text{X}}_2}{{\text{X}}_3} + {1}.0{\text{844X}}_1^2 + {3}.{35}00 \times {1}{0^{ - {3}}}{\text{X}}_2^2 + {2}.{6}000 \times {1}{0^{ - {3}}}{\text{X}}_3^2 \). The model with a very low probability value (P < 0.0003) was highly significant and the value of lack-of-fit was 0.4028, indicating that the model could predict water activity of shrimps using different agents. Composite phosphate of 0.22%, sorbitol of 3.12% and glycerol of 2.51% were found to be the optimal condition to obtain the lowest water activity of 0.884. Compared to the control shrimps, RTE shrimps treated with water-activity-lowering agents had a longer shelflife and higher sensorial acceptability. During storage at temperature of 35 °C, the quality of RTE shrimps in term of appearance, flavor and texture was found to be superior to the untreated ones. Texture profile, TBARS value, contents of astaxanthin and free amino acid of treated samples were found to be decreased slower from origin value compared to that of untreated samples. These RTE shrimps were biologically safe and sensorially acceptable after 30 days of storage at temperature of 35 °C. Briefly, the application of water-activity-lowering agents extent the shelflife of RTE shrimps obviously and would be beneficial for the exploitation of white shrimp.
Co-reporter:QIAO-MING LOU;YU-MING WANG;XIAO-FANG LIU ;CHANG-HU XUE
Journal of Food Biochemistry 2012 Volume 36( Issue 3) pp:317-321
Publication Date(Web):
DOI:10.1111/j.1745-4514.2011.00544.x
ABSTRACT
The lipid profile and fatty acid compositions in the body wall of Apostichopus japonicus (Selenka) have been analyzed. The level of total lipids in the body wall that was 3.93 ± 0.27% of dry weight (w/w) and the amount of phospholipids was 43.32 ± 2.10% of total lipids (w/w), exceeded that of neutral lipids and glycolipids. Phosphatidylcholine (PC) and phosphatidylethanolamine (PE) were the major phospholipids, and the contents were 58.93 ± 3.42% and 24.77 ± 1.34% of total phospholipids (w/w), respectively. Polyunsaturated fatty acids (PUFAs) were abundant in total lipids, PC and PE, and the main PUFAs were arachidonic acid (AA), eicosapentaenoic acid (EPA) and docosahexaenoic acid. PE contained much higher C18:0 dimethyl acetals and AA, but lower C18:1 and EPA compared with PC. The results indicated that there were some differences in the fatty acid compositions between PE and PC.
PRACTICAL APPLICATIONS
The cultivation scale of Apostichopus japonicus (Selenka) is on the increase in Northern China, and the consumption of A. japonicus becomes a fashion due to its nutritional and supposed medicinal properties. This study analyzes the lipid profile and phospholipid compositions of the body wall of A. japonicus, and compares the fatty acid compositions between phosphatidylethanolamine and phosphatidylcholine. The results could provide some useful information in the nutritional value of lipids for the exploitation of A. japonicus as a valuable functional and health food.
Co-reporter:Shiguo Chen, Changhu Xue, Li’ang Yin, Qingjuan Tang, Guangli Yu, Wengang Chai
Carbohydrate Polymers 2011 Volume 83(Issue 2) pp:688-696
Publication Date(Web):10 January 2011
DOI:10.1016/j.carbpol.2010.08.040
Fucosylated chondroitin sulfates (fCSs) were isolated from four sea cucumbers Pearsonothuria graeffei (Indo-Pacific), Stichopus tremulus (Western Indian Ocean), Holothuria vagabunda (Norwegian coast), and Isostichopus badionotus (Western Atlantic). The detailed sequences of fCSs, particularly their fucose branches, were characterized and compared. 1H and 13C NMR of the polysaccharides clearly identified three different sulfation patterns on the branched fucoses, 4-O-mono-, 2,3-O-di- and 2,4-O-di-sulfation, variously distributed in the four fCSs. The chondroitin sulfate backbones were established based on the monosaccharide composition of the polysaccharides and two-dimensional NMR of their oligosaccharide fragments. Anticoagulant activities of the four fCSs were assessed and compared. The results indicated that the difference in their anticoagulant activities can be attributed to the difference in sulfation pattern of the fucose branch of the chondroitin sulfate, and 2,4-O-disulfation is important for anticoagulant activity.
Co-reporter:Lingzhao Wang, Changhu Xue, Yuming Wang, and Bao Yang
Journal of Agricultural and Food Chemistry 2011 Volume 59(Issue 11) pp:6108-6112
Publication Date(Web):May 4, 2011
DOI:10.1021/jf201009t
The extraction of proteins with low fluoride level (LFP) from Antarctic krill (Euphausia superba) was investigated in this work. The optimal conditions for protein solubilization were determined to be pH 11.5 and 4 °C. The proteins were solubilized two times; a water/krill ratio (mL/g) of 6 and a time of 30 min were used for the first step, whereas the second used a water/krill residue ratio (mL/g) of 3 and a time of 30 min. The optimum pH for protein precipitation was 4.6. A LFP with fluoride content of 9.86 mg/kg (dry weight) was finally obtained through a fluoride removal program. The protein yield of LFP was 52.68%. Composition analysis of LFP indicated it was composed of 66.96% of crude proteins (dry weight) and 33.01% of total lipids (dry weight),, and all nine essential amino acids were in sufficient amounts to meet FAO/WHO/UNU requirements for adults and infants. In addition, LFP could be taken as a good source of EPA and DHA for consideration of use as a food item for human consumption.
Co-reporter:Jie Xu, Jingjing Duan, Changhu Xue, Tingyu Feng, Ping Dong, Tatsuya Sugawara, and Takashi Hirata
Journal of Agricultural and Food Chemistry 2011 Volume 59(Issue 22) pp:12246-12253
Publication Date(Web):October 17, 2011
DOI:10.1021/jf203556s
Sphingolipids constitute a highly diverse and complex class of molecules and exhibit important physiological functions. Glucocerebrosides are anticipated to play a positive role in human nutrition. In this study, complicated glucocerebrosides from three specimens of edible sea cucumbers, specifically, Acaudina molpadioides, Cucumaria frondosa, and Apostichopus japonicus, were rapidly identified using liquid chromatography–ion trap–time-of-flight mass spectrometry (LCMS-IT-TOF), which is a powerful analysis tool. [M + H]+, [M + Na]+, and [M + H – H2O]+ in positive electrospray ionization (ESI) mode were used for MS/MS analysis to obtain product ion spectra. Various long-chain bases of glucocerebrosides were found in these sea cucumbers. Two of the most common long-chain bases were 2-amino-1,3-dihydroxy-4-heptadecene (d17:1) and 4,8-sphingadienine (d18:2), which were acylated to form saturated and monounsaturated nonhydroxy and monohydroxy fatty acids with 18–25 carbon atoms. The glucocerebroside molecular species were the most complicated in the sea cucumber C. frondosa and were the simplest in the sea cucumber A. molpadioides.
Co-reporter:Qin Zhao;Zhi-dong Liu;Yong Xue
Journal of Zhejiang University-SCIENCE B 2011 Volume 12( Issue 7) pp:534-544
Publication Date(Web):2011 July
DOI:10.1631/jzus.B1000217
Ds-echinoside A (DSEA), a non-sulfated triterpene glycoside, was isolated from the sea cucumber Pearsonothuria graeffei. In vitro and in vivo investigations were conducted on the effects of DSEA on tumor cell adhesion, migration, invasion, and angiogenesis. In this study, we found that DSEA inhibited the proliferation of human hepatocellular liver carcinoma cells Hep G2, with a half-maximal inhibitory concentration (IC50) of 2.65 μmol/L, and suppressed Hep G2 cell adhesion, migration, and invasion in a dose-dependent manner. DSEA also reduced tube formation of human endothelial cells ECV-304 on matrigel in vitro and attenuated neovascularization in the chick embryo chorioallantoic membrane (CAM) assay in vivo. Immunocytochemical analysis revealed that DSEA significantly decreased the expression of matrix metalloproteinase-9 (MMP-9), which plays an important role in the degradation of basement membrane in tumor metastasis and angiogenesis. DSEA also increased the protein expression level of tissue inhibitor of metalloproteinase-1 (TIMP-1), an important regulator of MMP-9 activation. From the results of Western blotting, the expressions of nuclear factor-kappa B (NF-κB) and vascular endothelial growth factor (VEGF) were found to be remarkably reduced by DSEA. These findings suggest that DSEA exhibits a significant antimetastatic activity through the specific inhibition of NF-κB-dependent MMP-9 and VEGF expressions.
Co-reporter:Shiguo Chen, Jingfeng Wang, Changhu Xue, Hui Li, Beibei Sun, Yong Xue, Wengang Chai
Carbohydrate Polymers 2010 Volume 81(Issue 3) pp:560-566
Publication Date(Web):7 July 2010
DOI:10.1016/j.carbpol.2010.03.009
This paper is the first to report the preparation, characterization, and potential biological activities of a chemically sulfated polysaccharide isolated from the ink of the squid, Ommastrephes bartrami. The squid ink polysaccharides (SIPs) were firstly sulfated with the pyridine–sulfur-trioxide complex in dimethyl sulfoxide. Structural characterization of sulfated SIP using nuclear magnetic resonance indicated that sulfation mainly occurred at the 4,6-position of GalNAc. The effects of the sulfated SIP (TBA-1) on tumor cell growth, invasion, and migration were examined in vitro, and its effects on angiogenesis were measured in vivo using the chick embryo chorioallantoic membrane (CAM) assay. TBA-1 did not have any obvious effects on the proliferation of HepG2 tumor cells, but induced the dose-dependent suppression of cell invasion and migration in HepG2. Moreover, TBA-1 obviously inhibited angiogenesis in a CAM model. Thus, our results indicate that TBA-1 is a potential candidate compound for the prevention of tumor metastasis.
Co-reporter:Feng Li, Hong-ying Liu, Chang-hu Xue, Xue-qian Xin, Jie Xu, Yao-guang Chang, Yong Xue, Li-ang Yin
Journal of Chromatography A 2009 Volume 1216(Issue 31) pp:5924-5926
Publication Date(Web):31 July 2009
DOI:10.1016/j.chroma.2009.06.038
An ion chromatography method with non-suppressed conductivity detection was developed for the simultaneous determination of dimethylamine (DMA), trimethylamine (TMA) and trimethylamine-n-oxide (TMAO) in aquatic products. They were separated by means of cation-exchange chromatography using a 3.0 mmol/L methanesulfonic acid solution as eluent and an IonPac CS17 column (250 mm × 4 mm i.d.) as the separation column. Detection limits of dimethylamine, trimethylamine and trimethylamine-n-oxide were 0.06, 0.08 and 0.10 mg/L, respectively. The relative standard deviations (RSDs) of peak area were less than 3.53%. The recoveries were between 93.7% and 104.1%. Unlike traditional methods, this validated method is inexpensive and stable.
Co-reporter:Qi-Long Shi, Ya Zhao, Hai-Hua Chen, Zhao-Jie Li, Chang-Hu Xue
Thermochimica Acta 2009 Volume 493(1–2) pp:55-60
Publication Date(Web):10 September 2009
DOI:10.1016/j.tca.2009.04.006
Glass transition temperatures of freeze-dried horse mackerel muscle conditioned at various water activities at 25 °C were determined by differential scanning calorimetry (DSC). High moisture content (>0.33 g/g, d.b.) samples obtained by adding liquid water into freeze-dried samples, were also analyzed. The state diagram was composed of the freezing curve and the glass transition line, which were fitted according to Clausius–Clapeyron model and Gordon–Taylor model, respectively. The state diagram yielded maximally freeze-concentrated solutes at 0.786 solids with the characteristic temperature of glass formation being −83.1 °C. The state diagram of horse mackerel muscle developed in this work could be used to predict the stability during frozen storage and in dried conditions as well as in designing drying and freezing processes.
Co-reporter:Rui-chang Gao, Li Yuan, Qi Wang, Yong Xue, Hui Feng, Li-ang Yin, Jing-feng Wang, Chang-hu Xue
Journal of Chromatography A 2008 Volume 1208(1–2) pp:239-241
Publication Date(Web):24 October 2008
DOI:10.1016/j.chroma.2008.08.099
A precise analytical assay was developed and validated for the determination of Pacific oyster glycogen using ion chromatography. The Pacific oyster glycogen was quantified by the determination of glucose-6-phosphate (Glc-6-P), which was derived from glucose that was hydrolyzed from glycogen. Glc-6-P, adenosine triphosphate, and adenosine diphosphate were separated by ion chromatography. The method was validated over the curve range 0.5–100 mg/L for the abovementioned analytes. The recoveries were between 95% and 102%. The relative standard deviations (RSDs, c = 10 mg/L, n = 9) were less than 4.37%. Unlike a traditional method, this validated method was inexpensive and stable.
Co-reporter:Ping Dong, Chang-hu Xue, Lin-fang Yu, Jie Xu and Shi-guo Chen
Journal of Agricultural and Food Chemistry 2008 Volume 56(Issue 13) pp:4937-4942
Publication Date(Web):June 17, 2008
DOI:10.1021/jf800893r
A creative and sensitive method has been developed for the determination of triterpene glycosides concentrations in sea cucumber (Stichopus japonicus) and related products by using d-quinovose (6-deoxyglucose) as the measurement standard by reverse-phase high-performance liquid chromatography (HPLC) and variable-wavelength detection. d-quinovose, which is a unique monosaccharide in holostane triterpene glycosides, was liberated by acid hydrolysis and precolumn derivatized by 1-phenyl-3-methyl-5-pyrazolone (PMP). PMP−quinovose was analyzed by HPLC with 22% acetonitrile in 0.05 M KH2PO4 aquatic solution (pH 5.2) as mobile phase. The calibration curves of d-quinovose were linear within the range of 6.56−164 mg/L (r2 > 0.995). The contents of triterpene glycosides in various S. japonicus products were determined after appropriate pretreatment methods. The concentration of triterpene glycosides was calculated by the formula C = Cqui × α (α = 8.5). The result showed that this method was a simple, rapid, and stable method for the determination of triterpene glycosides in S. japonicus products.
Co-reporter:Yongqin Zhang, Changhu Xue, Zhaojie Li, Yani Zhang, Xueyan Fu
Carbohydrate Polymers 2006 Volume 65(Issue 3) pp:229-234
Publication Date(Web):15 August 2006
DOI:10.1016/j.carbpol.2005.08.066
A novel rapid preparation of half-deacetylated chitosan with relatively large molecular weight was studied. Chitin from shrimp was first undergone forced penetration in vacuum and then deacetylated using concentrated NaOH with control of the reaction time. The degree of deacetylation (DD) was monitored using potentiometric titration and 1H NMR. The half-deacetylated chitosan showed a distinct change in Scanning electronic microscopy (SEM) compared to chitin material, and behaved viscous and translucent in water. They were turned into microfibrils with a diameter of around 1 μm, which facilitate near homogeneous deacetylation. After degradation by pectinase, they were soluble in aqueous solution at all pH. The results of Intrinsic viscosity, FT-IR, and powder X-ray diffraction (XRD) show that the molecular weight and DD are collectively responsible for the solubility in the condition of random deacetylation of acetyl groups, which resulted from the intermolecular force.
Co-reporter:Rui-chang Gao, Chang-hu Xue, Li Yuan, Zhao-jie Li, Yong Xue, Fengxia Cui, Yan Sun
Journal of Chromatography A 2006 Volume 1118(Issue 2) pp:278-280
Publication Date(Web):23 June 2006
DOI:10.1016/j.chroma.2006.04.066
A method for the determination of adenosine triphosphatase (ATPase) activity of myofibrils of big head carp by using ion chromatography was introduced. Adenosine triphosphate (ATP), adenosine diphosphate (ADP) and orthophosphate (Pi) were separated completely. Recoveries for ATP, ADP and Pi were 98 ± 5%, 97 ± 4% and 98 ± 5%, respectively. Pi liberated from ATP during reaction was monitored by ion chromatography using the suggested method. This method was applicable to the determination of myofibrils ATPase activity for quick quality evaluation of surimi.
Co-reporter:Yanchao Wang, Shanshan Wang, Jingfeng Wang, Changhu Xue, Yaoguang Chang, Yong Xue
Peptides (June 2015) Volume 68() pp:239-245
Publication Date(Web):1 June 2015
DOI:10.1016/j.peptides.2014.10.004
•Phosphorylated protein was prepared from krill protein isolate by dry-heating.•Phosphorylated peptides from krill were hydrolyzed from phosphorylated protein.•These peptides contained two types of phosphate groups (OP and OP).•They dose-dependently preserved BMD and bone strength in osteoporotic rats.•Their anti-osteoporosis activity was due to the suppression of bone remodeling.Antarctic krill (Euphausia superba) protein serves as a novel sustainable protein source for human. Krill protein isolate was phosphorylated by the dry-heating method with sodium pyrophosphate. Phosphorylated peptides from Antarctic krill (PP-AKP) were obtained from phosphorylated protein through tryptic hydrolysis. Two types of phosphate bonds were introduced by phosphorylation, i.e. PO and PO bonds. The anti-osteoporotic activities of PP-AKP at two doses (400 and 800 mg/kg body weight) were investigated with an osteoporotic rat model, which was established with bilateral ovariectomy surgery. Different doses of PP-AKP were given intraperitoneal injections to rats once a day with alendronate as a positive control. Phosphorylated peptides from Antarctic krill dose-dependently preserved bone mineral density in osteoporotic rats by increasing the degree of bone mineralization. Both trabecular and cortical bone strength in osteoporotic rats was significantly improved with PP-AKP treatment. The mechanism by which PP-AKP augmented bone mineral density and bone strength was relation to the reduction in osteoclast-mediated bone remodeling, as was supported by the decrease in bone resorption markers. Phosphorylated peptides from Antarctic krill could be developed as functional food or nutritional supplements.Download full-size image
Co-reporter:Yiming Wang, Jingfeng Wang, Yanlei Zhao, Shiwei Hu, ... Changhu Xue
Journal of Bioscience and Bioengineering (January 2016) Volume 121(Issue 1) pp:36-42
Publication Date(Web):1 January 2016
DOI:10.1016/j.jbiosc.2015.05.012
The present study investigated the anti-hyperglycemic properties and mechanisms of fucoidan, isolated from Cucumaria frondosa (Cf-FUC), in insulin resistant mice. Male C57BL/6J mice were fed regular diet or high-fat/high-sucrose diet for 19 weeks. Model animals were dietary administrated either rosiglitazone (RSG, 1 mg/kg·bw), fucoidan (Cf-FUC, 80 mg/kg·bw) or their combinations. Results showed that Cf-FUC significantly reduced fasting blood glucose and insulin levels, and enhanced glucose tolerance and insulin tolerance in insulin-resistant mice. Quantitative real-time PCR analysis showed that Cf-FUC increased the mRNA expressions of insulin receptors (IR), insulin receptor substrate 1 (IRS-1), phosphatidylinositol 3 kinase (PI3K), protein kinase B (PKB), and glucose transporter 4 (GLUT4). Western blot assays demonstrated that Cf-FUC showed no effect on total protein expression but nevertheless enhanced the phosphorylation of proteins listed above and increased translocation of GLUT4 to the cell membrane. Furthermore, Cf-FUC enhanced the effects of RSG. These results indicated that Cf-FUC exhibited significant anti-hyperglycemic effects via activating PI3K/PKB pathway and GLUT4 in skeletal muscle and adipose tissue.
Co-reporter:Xiangzhao Mao, Qianqian Liu, Yongqian Qiu, Xiaoqin Fan, Qingqing Han, Yanjun Liu, Lujia Zhang, Changhu Xue
Journal of Biotechnology (10 May 2017) Volume 249() pp:51-58
Publication Date(Web):10 May 2017
DOI:10.1016/j.jbiotec.2017.03.029
•PS and DHA-PS were effectively synthesized by a novel phospholipase D without byproduct.•The novel phospholipase D was firstly cloned from Acinetobacter radioresistens strain.•The phospholipase D revealed both high transphosphatidylation conversion rate and selectivity.•The conversion rate and selectivity of PS and DHA-PS in 12 h reaction were all about 100%.•The catalytic selectivity mechanism was explained by utilizing homology modeling.Phosphatidylserine (PS) and docosahexaenoic acid-phosphatidylserine (DHA-PS) have significant nutritional and biological functions, which are extensively used in functional food industries. Phospholipase D (PLD)-mediated transphosphatidylation of phosphatidylcholine (PC) or DHA-PC with l-serine, is an effective method for PS and DHA-PS preparation. However, because of the hydrolysis activity of PLD, PC and DHA-PC would be converted to the undesirable byproduct, phosphatidic acid (PA) and DHA-PA. In this study, a novel phospholipase D (PLDa2) was firstly cloned from Acinetobacter radioresistens a2 with high transphosphatidylation activity and no hydrolysis activity. In the PLD-catalyzed synthesis process (12 h), both the transphosphatidylation conversion rate and selectivity of PS and DHA-PS were about 100%, which is the only PLD enzyme reported with this superiority up till now. In comparison with the majority of other known PLDs, PLDa2 exerted the highest activity at neutral pH, and it was stable from pH 4.0 to pH 9.0. In addition, PLDa2 had excellent thermal stability, with an optimum reaction temperature of 40 °C and keeping more than 80% activity from 20 °C to 60 °C. The high catalytic selectivity mechanism of PLDa2 was explained by utilizing homology modeling, two-step docking, and binding energy and conformation analysis. PLDa2 ensured a stable supply of the biocatalyst with its most preponderant transphosphatidylation activity and PS selectivity, and had great potential in phospholipids industrial production.
Co-reporter:Yanjun Liu, Qin Zhang, Yongli Guo, Junyi Liu, Jie Xu, Zhaojie Li, Jingfeng Wang, Yuming Wang, Changhu Xue
Food Chemistry (1 July 2017) Volume 226() pp:
Publication Date(Web):1 July 2017
DOI:10.1016/j.foodchem.2017.01.066
•Lipases TLIM was more effective than phospholipases and other lipases for esterification of GPC and n−3 PUFA.•Optimal conditions were a temperature of 45 °C, a mole ratio of 1:20 (GPC to n−3 PUFA) under vacuum for 64 h.•The 1-acyl-sn-glycero-3-lysophosphatidylcholine (2-LPC) was predominant in the reaction.The n−3 polyunsaturated fatty acids (PUFA)-rich lysophosphatidylcholine (LPC) was successfully synthesized by Thermomyces lanuginosus lipase (TL IM)-catalyzed esterification of glycerylphosphorylcholine (GPC) and n−3 PUFA-rich fatty acids in a solvent-free system. Effects of reaction temperature, enzyme loading and substrate mole ratio on the yield of LPC and incorporation of n−3 PUFA were evaluated. The acyl-specificities of five enzymes were tested for direct esterification of n−3 PUFA, and Lipozyme TL IM was found to be more effective than others for production of LPC with n−3 PUFA. Substrate mole ratio and reaction temperature, however, had no significant effect on the incorporation. The maximal yield of LPC was obtained under the following conditions: temperature 45 °C, enzyme loading 15% by weight and substrate mole ratio (GPC/n−3 PUFA) 1:20. Furthermore, the composition of products were further investigated in the study. The 1-acyl-sn-glycero-3-lysophosphatidylcholine (2-LPC) was predominant in the mixtures at early stages of reaction, whereas less increment of 2-acyl-sn-glycero-3-lysophosphatidylcholine (1-LPC) and PC was observed at later stages.
![Heptadecanamide,N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-](http://img.cochemist.com/ccimg/67500/67492-16-4.png)
![Heptadecanamide,N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-](http://img.cochemist.com/ccimg/67500/67492-16-4_b.png)
![5-Heptenoic acid,7-[(2R,3S,4S)-tetrahydro-4,6-dihydroxy-2-[(1E,3S)-3-hydroxy-1-octen-1-yl]-2H-pyran-3-yl]-,(5Z)-](http://img.cochemist.com/ccimg/54400/54397-85-2.png)
![5-Heptenoic acid,7-[(2R,3S,4S)-tetrahydro-4,6-dihydroxy-2-[(1E,3S)-3-hydroxy-1-octen-1-yl]-2H-pyran-3-yl]-,(5Z)-](http://img.cochemist.com/ccimg/54400/54397-85-2_b.png)
![N-(3-METHYLBUTANOYL)-L-VALYL-N-[(3S,4S)-1-{[(2S)-1-{[(2S,3S)-1-CA<WBR />RBOXY-2-HYDROXY-5-METHYL-3-HEXANYL]AMINO}-1-OXO-2-PROPANYL]AMINO}<WBR />-3-HYDROXY-6-METHYL-1-OXO-4-HEPTANYL]-L-VALINAMIDE](http://img.cochemist.com/ccimg/39400/39324-30-6.png)
![N-(3-METHYLBUTANOYL)-L-VALYL-N-[(3S,4S)-1-{[(2S)-1-{[(2S,3S)-1-CA<WBR />RBOXY-2-HYDROXY-5-METHYL-3-HEXANYL]AMINO}-1-OXO-2-PROPANYL]AMINO}<WBR />-3-HYDROXY-6-METHYL-1-OXO-4-HEPTANYL]-L-VALINAMIDE](http://img.cochemist.com/ccimg/39400/39324-30-6_b.png)
![N-[5-(4-AMINOPHENOXY)PENTYL]FORMAMIDE](/data/chemimg/56300/484-58-2.png)
![N-[5-(4-AMINOPHENOXY)PENTYL]FORMAMIDE](/data/chemimg/56300/484-58-2_b.png)
![(2r)-2-amino-6-[4-[(2s)-2-amino-2-carboxyethyl]-3-[(3s)-3-amino-3-carboxypropyl]-5-hydroxypyridin-1-ium-1-yl]hexanoate](http://img.cochemist.com/ccimg/83500/83462-55-9.png)
![(2r)-2-amino-6-[4-[(2s)-2-amino-2-carboxyethyl]-3-[(3s)-3-amino-3-carboxypropyl]-5-hydroxypyridin-1-ium-1-yl]hexanoate](http://img.cochemist.com/ccimg/83500/83462-55-9_b.png)
