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| Research Progress on Separation, Purification, Structure Analysis and Biological Activity of Saponins in Sea Cucumber: a Review |
| LIU Guiying1, LIU Yujun1, ZHANG Yuyang2, WU Jinhao1, SONG Lun1, ZHOU Zunchun1, XIONG Shuang3, WANG Zheng4 |
1. Liaoning Ocean and Fisheries Science Research Institute, Dalian 116023, China;
2. Dalian Modern Agricultural Production Development Service Center, Dalian 116021, China;
3. Construction Engineering Center of Important Technology Innovation and Research and Development Base in Liaoning Province, Shenyang 110168, China;
4. Changhai County Ocean and Fishery Administrative Law Enforcement Team, Dalian 116500, China |
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Received: 17 November 2020
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[1]PURCELL S, SAMYN Y, CONAND C. Commercially important sea cucumbers of the world[R].Rome:Food and Agricultural Organization of the United Nations,2012:1-2.
[2]BAHRAMI Y, ZHANG W, FRANCO C M M. Distribution of saponins in the sea cucumber Holothuria lessoni;the body wall versus the viscera, and their biological activities[J].Marine Drugs,2018,16(11):423.
[3]BAHRAMI Y, FRANCO C M M. Acetylated triterpene glycosides and their biological activity from Holothuroidea reported in the past six decades[J].Marine Drugs,2016,14(8):147.
[4]MOHAMMADIZADEH F, EHSANPOR M, AFKHA-MI M, et al. Evaluation of antibacterial, antifungal and cytotoxic effects of Holothuria scabra from the north coast of the Persian Gulf[J].Journal de Mycologie Médicale,2013,23(4):225-229.
[5]MOKHLESI A, SAEIDNIA S, GOHARI A R, et al. Biological activities of the sea cucumber Holothuria leucospilota[J].Asian Journal of Animal and Veterinary Advances,2012,7(3):243-249.
[6]AFKHAMI M, EHSANPOUR M. Evaluation bioactivity of a sea cucumber, Stichopus hermanni from Persian Gulf[J].Journal of Experimental Biology,2014,4(2):254-258.
[7]芦晓芳,赵晋忠,常丽萍.三萜类酸枣仁皂苷的提取与纯化方法研究进展[J].天然产物研究与开发,2017,29(11):1976-1982.
[8]董微,郜玉钢,何忠梅,等.人参中人参皂苷提取分离研究进展[J].食品工业科技,2014,35(17):366-369.
[9]林建云,张林,傅天保.二色桌片参皂苷的分离及其理化性质[J].台湾海峡,2000,19(2):186-191.
[10]邹峥嵘,易杨华,张淑瑜,等.海参皂苷研究进展[J].中国海洋药物,2004,23(1):46-53.
[11]刘桂英,王旭达,葛坤,等.响应面法优化提取仿刺参中海参皂苷工艺[J]. 水产科学, 2021,40(6):810-817.
[12]TIAN F, ZHANG X W, TONG Y, et al. PE, a new sulfated saponin from sea cucumber, exhibits anti-angiogenic and anti-tumor activities in vitro and in vivo[J].Cancer Biology & Therapy,2005,4(8):874-882.
[13]苏永昌,刘淑集,阮伟达,等.响应面法优化海地瓜皂苷提取工艺[J].食品工业科技,2016,37(21):205-209.
[14]袁炜辉,李赫宇,李倩,等.海参皂苷的分离提取及分析方法研究进展[J].食品研究与开发,2017,38(7):220-224.
[15]YASUMOTO T, NAKAMURA K, HASHIMOTO Y. A new saponin, holothurin B, isolated from sea-cucumber, Holothuria vagabunda and Holothuria lubrica[J].Agricultural and Biological Chemistry,1967,31(1):7-10.
[16]袁文鹏.仿刺参(Apostichopus japonicus)水溶性海参皂苷的分离纯化及其药理活性研究[D].青岛:中国海洋大学,2007.
[17]YAMANOUCHI T. On the poisonous substance contained in holothurians[J].Publications of the Seto Marine Biological Laboratory,1955,4(2/3):183-203.
[18]于林芳,王超,王玉明,等.大孔树脂纯化革皮氏海参总皂苷工艺[J].食品科学,2011,32(12):1-4.
[19]KERR R G, CHEN Z. In vivo and in vitro biosynthesis of saponins in sea cucumbers[J].Journal of Natural Products,1995,58(2):172-176.
[20]KHATTAB R A, ELBANDY M, LAWRENCE A, et al. Extraction, identification and biological activities of saponins in sea cucumber Pearsonothuria graeffei[J].Combinatorial Chemistry & High Throughput Screening,2018,21(3):222-231.
[21]QU L P, XIN H L, SU Y H, et al. Combined application of macroporous resin and high speed counter-current chromatography for preparative separation of three flavonoid triglycosides from the leaves of Actinidia valvata Dunn[J].Journal of Separation Science,2012,35(7):883-892.
[22]阮伟达,刘秋凤,苏永昌.大孔吸附树脂纯化海地瓜总皂苷的研究[J].渔业研究,2017,39(5):357-364.
[23]ZHANG X M, LI X B, ZHANG S S, et al. LC-MS/MS identification of novel saponins from the viscera of sea cucumber Apostichopus japonicus[J].Chemistry of Natural Compounds,2018,54(4):721-725.
[24]CHEN C, HAN X Q, DONG P, et al. Sea cucumber saponin liposomes ameliorate obesity-induced inflammation and insulin resistance in high-fat-diet-fed mice[J].Food & Function,2018,9(2):861-870.
[25]GUO Y, HAN X Q, CHE H X, et al. Synergistic effect of eicosapentaenoic acid-enriched phospholipids and sea cucumber saponin on orotic acid-induced non-alcoholic fatty liver disease in rats[J].Royal Society Open Science,2018,5(7):172182.
[26]于林芳.八种海参中主要海参皂苷的结构特性研究[D].青岛:中国海洋大学,2011.
[27]徐蕾,宋清平,杨爽,等.仿刺参(Apostichopus japonicus)中皂苷类成分的分离鉴定及细胞毒活性研究[J].中国海洋药物,2018,37(6):38-46.
[28]DING L, ZHANG T T, CHE H X, et al. Saponins of sea cucumber attenuate atherosclerosis in ApoE-/- mice via lipid-lowering and anti-inflammatory properties[J].Journal of Functional Foods,2018,48:490-497.
[29]LI R, ZHANG L Y, LI Z J, et al. Characterization and absorption kinetics of a novel multifunctional nanoliposome stabilized by sea cucumber saponins instead of cholesterol[J].Journal of Agricultural and Food Chemistry,2020,68(2):642-651.
[30]闫冰,李玲,易杨华,等.糙海参中三萜皂苷活性成分的研究[J].第二军医大学学报,2005,26(6):626-631.
[31]张宏伟,易杨华,袁卫华,等.辐肛参中4个抗真菌活性海参皂苷[J].第二军医大学学报,2010,31(5):521-526.
[32]CARR B R, MIKHAIL G, FLICKINGER G L. Column chromatography of steroids on sephadex LH-20[J].The Journal of Clinical Endocrinology & Metabolism,1971,33(2):358-360.
[33]HAN Q, LI K F, DONG X P, et al. Function of Thelenota ananas saponin desulfated holothurin A in modulating cholesterol metabolism[J].Scientific Reports,2018,8:9506.
[34]THAO N P, LUYEN B T T, LE VIEN T, et al. Triterpene saponins from the sea cucumber Stichopus chloronotus[J].Natural Product Communications,2014,9(5):615-618.
[35]AMININ D L, MENCHINSKAYA E S, PISLIAGIN E A, et al. Anticancer activity of sea cucumber triterpene glycosides[J].Marine Drugs,2015,13(3):1202-1223.
[36]ATLABACHEW M, CHANDRAVANSHI B S, REDI-ABSHIRO M. Preparative HPLC for large scale isolation, and salting-out assisted liquid-liquid extraction based method for HPLC-DAD determination of khat (Catha edulis Forsk) alkaloids[J].Chemistry Central Journal,2017,11(1):107.
[37]ELBANDY M, RHO J R, AFIFI R. Analysis of saponins as bioactive zoochemicals from the marine functional food sea cucumber Bohadschia cousteaui[J].European Food Research and Technology,2014,238(6):937-955.
[38]WANG X H, ZOU Z R, YI Y H, et al. Variegatusides:new non-sulphated triterpene glycosides from the sea cucumber Stichopus variegates semper[J].Marine Drugs,2014,12(4):2004-2018.
[39]AVILOV S A, SILCHENKO A S, ANTONOV A S, et al. Synaptosides A and A1, triterpene glycosides from the sea cucumber Synapta maculata containing 3-O-methylglucuronic acid and their cytotoxic activity against tumor cells[J].Journal of Natural Products,2008,71(4):525-531.
[40]CAULIER G, MEZALI K, SOUALILI D L, et al. Chemical characterization of saponins contained in the body wall and the Cuvierian tubules of the sea cucumber Holothuria (Platyperona) sanctori (Delle Chiaje, 1823)[J].Biochemical Systematics and Ecology,2016,68:119-127.
[41]MONDOL M A M, SHIN H J, RAHMAN M A, et al. Sea cucumber glycosides:chemical structures, producing species and important biological properties[J].Marine Drugs,2017,15(10):317.
[42]刘玉锋.仿刺参(Apostichopus japonicus)皂苷HPLC-ELSD分析方法的建立及其定性鉴别[D].青岛:中国海洋大学,2012.
[43]DANG N H, THANH N V, KIEM P V, et al. Two new triterpene glycosides from the Vietnamese sea cucumber Holothuria scabra[J].Archives of Pharmacal Research,2007,30(11):1387-1391.
[44]DONG P, XUE C H, DU Q Z. Separation of two main triterpene glycosides from sea cucumber Pearsonothuria graeffei by high-speed countercurrent chromatography[J].Acta Chromatographica,2008,20(2):269-276.
[45]BAHRAMI Y, ZHANG W, FRANCO C. Discovery of novel saponins from the viscera of the sea cucumber Holothuria lessoni[J].Marine Drugs,2014,12(5):2633-2667.
[46]HOANG L, LE THI V, TRAN THI HONG H, et al. Triterpene glycosides from the Vietnamese sea cucumber Holothuria edulis[J].Natural Product Research,2019,34(8):1061-1067.
[47]ZHANG X M, HAN L W, SHENG W L, et al. Two novel non-holostane type glycosides from the viscera of sea cucumber Apostichopus japonicus[J].Journal of Asian Natural Products Research,2020,22(4):329-337.
[48]YU S R, YE X W, HUANG H C, et al. Bioactive sulfated saponins from sea cucumber Holothuria moebii[J].Planta Medica,2015,81(2):152-159.
[49]SILCHENKO A S, KALINOVSKY A I, AVILOV S A, et al. Triterpene glycosides from the sea cucumber Cladolabes schmeltzii.Ⅱ.Structure and biological action of cladolosides A1—A6[J].Natural Product Communications,2014,9(10):1421-1428.
[50]WANG Z L, ZHANG H W, YUAN W H, et al. Antifungal nortriterpene and triterpene glycosides from the sea cucumber Apostichopus japonicus Selenka[J].Food Chemistry,2012,132(1):295-300.
[51]SILCHENKO A S, KALINOVSKY A I, AVILOV S A, et al. Cladolosides I1, I2, J1, K1, K2 and L1, monosulfated triterpene glycosides with new carbohydrate chains from the sea cucumber Cladolabes schmeltzii[J].Carbohydrate Research,2017,445:80-87.
[52]SILCHENKO A S, KALINOVSKY A I, AVILOV S A, et al. Cladolosides C4, D1, D2, M, M1, M2, N and Q, new triterpene glycosides with diverse carbohydrate chains from sea cucumber Cladolabes schmeltzii. An uncommon 20, 21, 22, 23, 24, 25, 26, 27-okta-nor-lanostane aglycone.The synergism of inhibitory action of non-toxic dose of the glycosides and radioactive irradiation on colony formation of HT-29 cancer cells[J].Carbohydrate Research,2018,468:36-44.
[53]SILCHENKO A S, KALINOVSKY A I, AVILOV S A, et al. Cladolosides O, P, P1-P3 and R, triterpene glycosides with two novel types of carbohydrate chains from the sea cucumber Cladolabes schmeltzii. Inhibition of cancer cells colony formation and its synergy with radioactive irradiation[J].Carbohydrate Research,2018,468:73-79.
[54]SILCHENKO A S, KALINOVSKY A I, AVILOV S A, et al. Structures and biological activities of cladolosides C3, E1, E2, F1, F2, G, H1 and H2, eight triterpene glycosides from the sea cucumber Cladolabes schmeltzii with one known and four new carbohydrate chains[J].Carbohydrate Research,2015,414:22-31.
[55]CARR C, NG J, WIGMORE T. The side effects of chemotherapeutic agents[J].Current Anaesthesia & Critical Care,2008,19(2):70-79.
[56]ZHAO Q, XUE Y, WANG J F, et al. In vitro and in vivo anti-tumour activities of echinoside A and ds-echinoside A from Pearsonothuria graeffei[J].Journal of the Science of Food and Agriculture,2012,92(4):965-974.
[57]ZHAO Q, XUE Y, LIU Z D, et al. Differential effects of sulfated triterpene glycosides, holothurin A1, and 24-dehydroechinoside A, on antimetastasic activity via regulation of the MMP-9 signal pathway[J].Journal of Food Science,2010,75(9):H280-H288.
[58]TONG Y G, ZHANG X W, TIAN F, et al. Philinopside a, a novel marine-derived compound possessing dual anti-angiogenic and anti-tumor effects[J].International Journal of Cancer,2005,114(6):843-853.
[59]钟静诗,张健,刘芳,等.海参皂苷生物活性及其分子机制研究进展[J].食品与机械,2021,37(3):180-186.
[60]DAI Y L, KIM E A, LUO H M, et al. Characterization and anti-tumor activity of saponin-rich fractions of South Korean sea cucumbers (Apostichopus japonicus)[J].Journal of Food Science and Technology,2020,57(6):2283-2292.
[61]AMININ D. Immunomodulatory properties of sea cucumber triterpene glycosides[M]// GOPALAKRISHNAKONE P, HADDAD JR V, TUBARO A. Marine and Freshwater Toxins. Dordrecht: Springer Netherlands, 2016: 381-401.
[62]赵芹,王静凤,薛勇,等.3种海参的主要活性成分和免疫调节作用的比较研究[J].中国水产科学,2008,15(1):154-159.
[63]王静凤,傅佳,王玉明,等.革皮氏海参皂苷对小鼠免疫功能的调节作用[J].中国海洋大学学报(自然科学版),2010,40(2):28-32.
[64]AMININ D L, AGAFONOVA I G, KALININ V I, et al. Immunomodulatory properties of frondoside A, a major triterpene glycoside from the North Atlantic commercially harvested sea cucumber Cucumaria frondosa[J].Journal of Medicinal Food,2008,11(3):443-453.
[65]YANG W S, QI X R, XU Q Z, et al. A new sulfated triterpene glycoside from the sea cucumber Colochirus quadrangularis, and evaluation of its antifungal, antitumor and immunomodulatory activities[J].Bioorganic & Medicinal Chemistry,2021,41:116188.
[66]GRAUSO L, YEGDANEH A, SHARIFI M, et al. Molecular networking-based analysis of cytotoxic saponins from sea cucumber Holothuria atra[J].Marine Drugs,2019,17(2):86.
[67]DARYA M, SAJJADI M M, YOUSEFZADI M, et al. Antifouling and antibacterial activities of bioactive extracts from different organs of the sea cucumber Holothuria leucospilota[J].Helgoland Marine Research,2020,74:4.
[68]KITAGAWA I, KOBAYASHI M, INAMOTO T, et al. The structures of six antifungal oligoglycosides, stichlorosides A1, A2, B1, B2, C1, and C2, from the sea cucumber Stichopus chloronotus (Brandt)[J].Chemical and Pharmaceutical Bulletin,1981,29(8):2387-2391.
[69]KITAGAWA I, KOBAYASHI M, INAMOTO T, et al. Stichlorogenol and dehydrostichlorogenol, genuine aglycones of stichlorosides A1, B1, C1 and A2, B2, C2, from the sea cucumber Stichopus chloronotus (Brandt)[J].Chemical and Pharmaceutical Bulletin,1981,29(4):1189-1192.
[70]WANG Z L, GONG W, SUN G Q, et al. New holostan-type triterpene glycosides from the sea cucumber Apostichopus japonicus[J].Natural Product Communications,2012,7(11):1431-1434.
[71]YUAN W H, YI Y H, TANG H F, et al. Antifungal triterpene glycosides from the sea cucumber Bohadschia marmorata[J].Planta Medica,2009,75(2):168-173.
[72]KITAGAWA I, KOBAYASHI M, INAMOTO T, et al. Marine natural products.XIV.Structures of echinosides A and B, antifungal lanostane-oligosides from the sea cucumber Actinopyga echinites (Jaeger)[J].Chemical & Pharmaceutical Bulletin,1985,33(12):5214-5224.
[73]ESTEGHAMAT F, BROUGHTON J S, SMITH E, et al. CELA2A mutations predispose to early-onset atherosclerosis and metabolic syndrome and affect plasma insulin and platelet activation[J].Nature Genetics,2019,51(8):1233-1243.
[74]GURKA M J, GUO Y, FILIPP S L, et al. Metabolic syndrome severity is significantly associated with future coronary heart disease in Type 2 diabetes[J].Cardiovascular Diabetology,2018,17(1):17.
[75]LUO Z C, XU W C, ZHANG Y, et al. A review of saponin intervention in metabolic syndrome suggests further study on intestinal microbiota[J].Pharmacological Research,2020,160:105088.
[76]HAN X Q, ZHANG L Y, DING L, et al. Synergistic effect of sea cucumber saponins and EPA-enriched phospholipids on insulin resistance in high-fat diet-induced obese mice[J].Food & Function,2019,10(7):3955-3964.
[77]ZHAO Y C, XUE C H, ZHANG T T, et al. Saponins from sea cucumber and their biological activities[J].Journal of Agricultural and Food Chemistry,2018,66(28):7222-7237.
[78]CHEN S Y, LI X, LIU L, et al. Ophiopogonin D alleviates high-fat diet-induced metabolic syndrome and changes the structure of gut microbiota in mice[J].The FASEB Journal,2018,32(3):1139-1153.
[79]LI J, LI R G, LI N, et al. Mechanism of antidiabetic and synergistic effects of ginseng polysaccharide and ginsenoside Rb1 on diabetic rat model[J].Journal of Pharmaceutical and Biomedical Analysis,2018,158:451-460.
[80]HAN Q, JIA S L, LI K F, et al. Thelenota ananas saponin extracts attenuate the atherosclerosis in apoE-/- mice by modulating lipid metabolism[J].Journal of Functional Foods,2019,58:238-247.
[81]GUO L, GAO Z Y, ZHANG L Q, et al. Saponin-enriched sea cucumber extracts exhibit an antiobesity effect through inhibition of pancreatic lipase activity and upregulation of LXR-β signaling[J].Pharmaceutical Biology,2016,54(8):1312-1325.
[82]MENG J, HU X Q, ZHANG T T, et al. Saponin from sea cucumber exhibited more significant effects than ginsenoside on ameliorating high fat diet-induced obesity in C57BL/6 mice[J].MedChemComm,2018,9(4):725-734.
[83]巨盛楠,徐慧静,王玉明,等.海参皂苷Holothurin A和Echinoside A对肥胖小鼠尿酸代谢的影响[J].食品工业科技,2021,42(21):385-391.
[84]SONG S S, ZHANG L Y, CAO J, et al. Characterization of metabolic pathways and absorption of sea cucumber saponins, holothurin A and echinoside A, in vitro and in vivo[J].Journal of Food Science,2017,82(8):1961-1967. |
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