海星化学成分的研究进展
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摘要
海洋无脊椎动物海星中含有大量结构独特的具有生物活性的代谢产物,主要以甾醇化合物及皂苷的形式存在,且具有明显的生理活性和药理作用。本文综述了国内外近年来对海星中的甾醇化合物及皂苷的研究进展,为海星的进一步利用以及开发奠定了基础。
Marine invertebrate starfish contains a large number of unique biologically active metabolites,mainly in the form of steroid compounds and their saponins,and has obvious physiological activities and pharmacological effects.In this paper,the research progress of steroid compounds and their saponins in starfish in recent years is reviewed.It lays a foundation for the further utilization and development of starfish.
Marine invertebrate starfish contains a large number of unique biologically active metabolites,mainly in the form of steroid compounds and their saponins,and has obvious physiological activities and pharmacological effects.In this paper,the research progress of steroid compounds and their saponins in starfish in recent years is reviewed.It lays a foundation for the further utilization and development of starfish.
引文
[1]王唯玮,初学魁,吴照华.海星动物化学成份的研究:罗氏海盘车中的皂甙元[J].化学学报,1987,45(3):298-300。
[2]Hiekman C P,Roberts L S,Hiekman F M.Integartde prineiples of zoology[M].USA:Times mirror/mosby college publishing,1984:469.
[3]Brusea R C,Brusea G J.Invertibrate[M].USA:sinauer assoeiates Inc,1990:801.
[4]De'ath G,Fabricius K E,Sweatman H,et al.The 27-year decline of coral cover on the Great Barrier Reef and its causes[J].P Natl Acad Sci USA,2012,109(44):17995-17999.
[5]Wang W H,Li F M,Hong J,et al.Four new saponins from the starfish Certonardoa semiregularis[J].Chem Pharm Bull,2003,51(4):435.
[6]D'Auria M V,Minale L,Riccio R.Polyoxygenated steroids of marine origin[J].Chem Rev,1993,93(5):1839-1895.
[7]Cui J G,Wang Y,Lin C W,et al.Polyhydroxylated sterols with biological activities in marine organism[J].Nat Prod R&D,2000,12(6):94-100.
[8]Wang W H,Li F M,Jung J H,et al.Progress on the research of the chemical constitutes and activities from Asteroidea[J].Chin J Mar Drugs,2002,5:46-50.
[9]Ivanchina N V,Kicha A A,Stonik V A.Steroid glycosides from marine organisms[J].Steroids,2011,76(5):425-454.
[10]Chludil H D,Seldes A M,Maler M S.Antifungal steroidal glycosides from the Patagonian starfish Anasterias minuta:structure-activity correlations[J].J Nat Prod,2002,65(2):153-157.
[11]Xu R S.Chemistry of Natural Product[M].Beijing:Science Press,1993:786.
[12]韩力挥,袁文鹏,丛日山,等.海星生物活性物质研究进展[J].海洋湖沼通报,2006,2:104-110.
[13]Peng Y,Zheng J,Huang R,et al.Polyhydroxy steroids and saponins from China Sea starfish Asterina pectinifera and their biological activities[J].Chem Pharm Bull,2010,58(6):856-858.
[14]Palagiano E,Zollo E,Minale L,et al.Hopkins Isolation of20Glycosides from the Starfish Henricia downeyae,Collected in the Gulf of Mexico[J].J Nat Prod,1996,59(4):348-354.
[15]Marino S D,Palagiano E,Zollo F,et al.Steroid with a 7-membered 5-oxalactone B-ring from an Antarctic Starfish of the family Asteriidae[J].Tetrahedron,1997,53(25):8625-8628.
[16]Kicha A A,Kalinovsky A I,Ivanchina N V,et al.New Steroid Glycosides from the Deep-Water Starfish Mediaster murrayi[J].J Nat Prod,1999,62(2):279-282.
[17]Kicha A A,Ivanchina N V,Kalinovsky A I,et al.Sulfated steroid compounds from the starfish Aphelasterias japonica of the Kuril population[J].Russ ChemB+,2001,32(49):724-727.
[18]Ivanchina N V,Kicha A A,Kalinovsky A I,et al.New steroid glycosides from the starfish Asterias rathbuni[J].JNat Prod,2001,64(7):945-947.
[19]Chludil H D,Seldes A M,Maier M S.Antifungal steroidal glyco-sides from the patagonian starfish Anasterias minuta:structure-activity correlations[J].J Nat Prod,2002,65(2):153-157.
[20]Levina E V,Andriyashchenko P V,Kalinovsky A I,et al.Steroid compounds from the starfish Lysastrosoma anthosticta collected in the Sea of Japan[J].Russ ChemB+,2002,33(41):535-539.
[21]Levina E V,Kalinovskii A I,Andriyashchenko P V,et al.Steroid polyols from the Far-Eastern starfish Henricia sanguinolenta[J].Russ ChemB+,2002,51(12):2295-2298.
[22]Wang W H,Li F M,Alam N,et al.New saponins from the starfish Certonardoa semiregularis[J].J Nat Prod,2002,65:1649-1656.
[23]Marino S D,Borbone N,Maria I,et al.Bioactive Asterosaponins from the starfish Luidia quinaria and Psilaster cassiope.Isolation and structure characterization by two-dimensional NMR spectroscopy[J].J Nat Prod,2003,66(4):515-519.
[24]Kicha A A,Ivanchina N V,Kalinovskii A I,et al.Polar steroidal compounds from the Far-Eastern starfish Lethasterias nanimensis chelifera[J].Russ ChemB+,2004,53(2):447-454.
[25]Levina E V,Kalinovskii A I,Andriyashchenko P V,et al.A new steroidal glycoside phrygioside A and its aglycone from the starfish Hippasteria phrygiana[J].Russ ChemB+,2004,53(11):2634-2638.
[26]Levina E V,Kalinovsky A I,Levin V S.New Steroid Glycosides from the Starfish Fromia milleporella[J].Russ JBioorg Chem+,2006,32(1):84-88.
[27]Tang H F,Yi Y H,Li L,et al.Bioactive Asterosaponins from the Starfish Culcita novaeguineae[J].J Nat Prod,2005,68(8):337-341.
[28]Ivanchina N V,Kicha A A,Kalinovsky A I,et al.Polar Steroidal Compounds from the Far Estern Starfish Henricia leviuscula[J].J Nat Prod,2006,69(2):224-228.
[29]Kicha A A,Ivanchina N V,Kalinovsky A I,et al.Four new steroid glycosides from the Vietnamese starfish Linckia laevigata[J].Russ ChemB+,2004,56(4):823-830.
[30]Ivanchina N V,Malyarenko T V,Kicha A A,et al.Polar steroidal compounds from the Far Eastern starfish Lethasterias fusca[J].Russ ChemB+,2008,57(1):204-208.
[31]Kicha A A,Ivanchina N V,Kalinovsky A I,et al.Steroidal Triglycosides,Kurilensosides A,B,and C,and Other Polar Steroids from the Far Eastern Starfish Hippasteria kurilensis[J].J Nat Prod,2008,71(5):793-798.
[32]Kicha A A,Ivanchina N V,Kalinovsky A I,et al.Two New Steroid Glycosides from the Far East Starfish Hippasteria kurilensis[J].Russ J Bioorg Chem+,2009,35(4):504-509.
[33]Tang H F,Cheng G,Wu J,et al.Cytotoxic Asterosaponins Capable of Promoting Polymerization of Tubulin from the Starfish Culcita novaeguineae[J].J Nat Prod,2009,72(2):284-289.
[34]Malyarenko T V,Kicha A A,Ivanchina N V,et al.Three New Polyhydroxysteroids from the Tropical Starfish Asteropsis carinifera[J].Russ J Bioorg Chem+,2010,36(6):755-761.
[35]Ma N,Tang H F,Qiu F,et al.Polyhydroxysteroidal Glycosides from the Starfish Anthenea chinensis[J].J Nat Prod,2010,73(4):590-597.
[36]汤海峰,马宁,邱峰,等.中华五角海星中10个新的多羟基甾体苷及其肿瘤细胞毒性[C].//2010年中国药学大会暨第十届中国药师周论文集,2010:9.
[37]Kicha A A,Ivanchina N V,Huong T T T,et al.Two new asterosaponins,archasterosides A and B,from the Vietnamese starfish Archaster typicus and their anticancer properties[J].Bioorg Med Chem Lett,2010,20(12):3826-3830.
[38]Malyarenko T V,Kicha A A,Ivanchina N V,et al.Cariniferosides A-F and other steroidal biglycosides from the starfish Asteropsis carinifera[J].Steroids,2011,76(12):1280-1287.
[39]Hwang I H,Kim D W,Kim S J,et al.Asterosaponins lsolated from the Starfish Asterias amurensis[J].Chem Pharm Bull,2011,59(1):78-83.
[40]Thao N P,Cuong N X,Luyen B T,et al.Anti-inflammatory Asterosaponins from the Starfish Astropecten monacanthus[J].J Nat Prod,2013,76(9):1764-1770.
[41]Malyarenko T V,Kicha A A,Ivanchina N V,et al.Asterosaponins from the Far Eastern star?sh Leptasterias ochotensis and their anticancer activity[J].Steroids,2014,87(13):119-127.
[42]Malyarenko T V,Malyarenko O V,Ivanchina N V,et al.Four New Sulfated Polar Steroids from the Far Eastern Starfish Leptasterias ochotensis:Structures and Activities[J].Mar Drugs,2015,13(7):4418-4435.
[43]Kicha A A,Kalinovsky A I,Malyarenko T V,et al.Cyclic Steroid Glycosides from the Star?sh Echinaster luzonicus:Structures and Immunomodulatory Activities[J].J Nat Prod,2015,78(6):1397-1405.
[44]Kang J X,Kang Y F,Han H.Three New Cytotoxic Polyhydroxysteroidal Glycosides from Starfish Craspidaster hesperus[J].Mar Drugs,2016,14(10):189.
[45]Malyarenko T V,Kharchenko S D,Kicha A A,et al.Anthenosides L-U,Steroidal Glycosides with Unusual Structural Features from the Starfish Anthenea aspera[J].J Nat Prod,2016,79(12):3047-3056.
[46]Malyarenko T V,Kicha A A,Kalinovsky A I,et al.Four New Steroidal Glycosides,Protolinckiosides A-D,from the Starfish Protoreaster lincki[J].Chem Biodivers,2016,13:998-1007.
[47]Hanh T T,Vien L T,Vinh L B,et al.Further Highly Hydroxylated Steroids from the Vietnamese Star?sh Archaster typicus[J].Chem Pharm Bull,2016,64(10):1523-1527.
[48]Kicha A A,Kalinovsky A I,Ivanchina N V,et al.Furostane Series Asterosaponins and Other Unusual Steroid Oligoglycosides from the Tropical Starfish Pentaceraster regulus[J].J Nat Prod,2017,80(10):2761-2770.
[49]Malyarenko T V,Ivanchina N V,Malyarenko O S,et al.Two New Steroidal Monoglycosides,Anthenosides A1and A2,and Revision of the Structure of Known Anthenoside A with Unusual Monosaccharide Residue from the Starfish Anthenea aspera[J].Molecules,2018,23(5):1077.
[50]Lu Y,Li H,Wang M,et al.Cytotoxic Polyhydroxysteroidal Glycosides from Starfish Culcita novaeguineae[J].Mar Drugs,2018,16(3):92.
[2]Hiekman C P,Roberts L S,Hiekman F M.Integartde prineiples of zoology[M].USA:Times mirror/mosby college publishing,1984:469.
[3]Brusea R C,Brusea G J.Invertibrate[M].USA:sinauer assoeiates Inc,1990:801.
[4]De'ath G,Fabricius K E,Sweatman H,et al.The 27-year decline of coral cover on the Great Barrier Reef and its causes[J].P Natl Acad Sci USA,2012,109(44):17995-17999.
[5]Wang W H,Li F M,Hong J,et al.Four new saponins from the starfish Certonardoa semiregularis[J].Chem Pharm Bull,2003,51(4):435.
[6]D'Auria M V,Minale L,Riccio R.Polyoxygenated steroids of marine origin[J].Chem Rev,1993,93(5):1839-1895.
[7]Cui J G,Wang Y,Lin C W,et al.Polyhydroxylated sterols with biological activities in marine organism[J].Nat Prod R&D,2000,12(6):94-100.
[8]Wang W H,Li F M,Jung J H,et al.Progress on the research of the chemical constitutes and activities from Asteroidea[J].Chin J Mar Drugs,2002,5:46-50.
[9]Ivanchina N V,Kicha A A,Stonik V A.Steroid glycosides from marine organisms[J].Steroids,2011,76(5):425-454.
[10]Chludil H D,Seldes A M,Maler M S.Antifungal steroidal glycosides from the Patagonian starfish Anasterias minuta:structure-activity correlations[J].J Nat Prod,2002,65(2):153-157.
[11]Xu R S.Chemistry of Natural Product[M].Beijing:Science Press,1993:786.
[12]韩力挥,袁文鹏,丛日山,等.海星生物活性物质研究进展[J].海洋湖沼通报,2006,2:104-110.
[13]Peng Y,Zheng J,Huang R,et al.Polyhydroxy steroids and saponins from China Sea starfish Asterina pectinifera and their biological activities[J].Chem Pharm Bull,2010,58(6):856-858.
[14]Palagiano E,Zollo E,Minale L,et al.Hopkins Isolation of20Glycosides from the Starfish Henricia downeyae,Collected in the Gulf of Mexico[J].J Nat Prod,1996,59(4):348-354.
[15]Marino S D,Palagiano E,Zollo F,et al.Steroid with a 7-membered 5-oxalactone B-ring from an Antarctic Starfish of the family Asteriidae[J].Tetrahedron,1997,53(25):8625-8628.
[16]Kicha A A,Kalinovsky A I,Ivanchina N V,et al.New Steroid Glycosides from the Deep-Water Starfish Mediaster murrayi[J].J Nat Prod,1999,62(2):279-282.
[17]Kicha A A,Ivanchina N V,Kalinovsky A I,et al.Sulfated steroid compounds from the starfish Aphelasterias japonica of the Kuril population[J].Russ ChemB+,2001,32(49):724-727.
[18]Ivanchina N V,Kicha A A,Kalinovsky A I,et al.New steroid glycosides from the starfish Asterias rathbuni[J].JNat Prod,2001,64(7):945-947.
[19]Chludil H D,Seldes A M,Maier M S.Antifungal steroidal glyco-sides from the patagonian starfish Anasterias minuta:structure-activity correlations[J].J Nat Prod,2002,65(2):153-157.
[20]Levina E V,Andriyashchenko P V,Kalinovsky A I,et al.Steroid compounds from the starfish Lysastrosoma anthosticta collected in the Sea of Japan[J].Russ ChemB+,2002,33(41):535-539.
[21]Levina E V,Kalinovskii A I,Andriyashchenko P V,et al.Steroid polyols from the Far-Eastern starfish Henricia sanguinolenta[J].Russ ChemB+,2002,51(12):2295-2298.
[22]Wang W H,Li F M,Alam N,et al.New saponins from the starfish Certonardoa semiregularis[J].J Nat Prod,2002,65:1649-1656.
[23]Marino S D,Borbone N,Maria I,et al.Bioactive Asterosaponins from the starfish Luidia quinaria and Psilaster cassiope.Isolation and structure characterization by two-dimensional NMR spectroscopy[J].J Nat Prod,2003,66(4):515-519.
[24]Kicha A A,Ivanchina N V,Kalinovskii A I,et al.Polar steroidal compounds from the Far-Eastern starfish Lethasterias nanimensis chelifera[J].Russ ChemB+,2004,53(2):447-454.
[25]Levina E V,Kalinovskii A I,Andriyashchenko P V,et al.A new steroidal glycoside phrygioside A and its aglycone from the starfish Hippasteria phrygiana[J].Russ ChemB+,2004,53(11):2634-2638.
[26]Levina E V,Kalinovsky A I,Levin V S.New Steroid Glycosides from the Starfish Fromia milleporella[J].Russ JBioorg Chem+,2006,32(1):84-88.
[27]Tang H F,Yi Y H,Li L,et al.Bioactive Asterosaponins from the Starfish Culcita novaeguineae[J].J Nat Prod,2005,68(8):337-341.
[28]Ivanchina N V,Kicha A A,Kalinovsky A I,et al.Polar Steroidal Compounds from the Far Estern Starfish Henricia leviuscula[J].J Nat Prod,2006,69(2):224-228.
[29]Kicha A A,Ivanchina N V,Kalinovsky A I,et al.Four new steroid glycosides from the Vietnamese starfish Linckia laevigata[J].Russ ChemB+,2004,56(4):823-830.
[30]Ivanchina N V,Malyarenko T V,Kicha A A,et al.Polar steroidal compounds from the Far Eastern starfish Lethasterias fusca[J].Russ ChemB+,2008,57(1):204-208.
[31]Kicha A A,Ivanchina N V,Kalinovsky A I,et al.Steroidal Triglycosides,Kurilensosides A,B,and C,and Other Polar Steroids from the Far Eastern Starfish Hippasteria kurilensis[J].J Nat Prod,2008,71(5):793-798.
[32]Kicha A A,Ivanchina N V,Kalinovsky A I,et al.Two New Steroid Glycosides from the Far East Starfish Hippasteria kurilensis[J].Russ J Bioorg Chem+,2009,35(4):504-509.
[33]Tang H F,Cheng G,Wu J,et al.Cytotoxic Asterosaponins Capable of Promoting Polymerization of Tubulin from the Starfish Culcita novaeguineae[J].J Nat Prod,2009,72(2):284-289.
[34]Malyarenko T V,Kicha A A,Ivanchina N V,et al.Three New Polyhydroxysteroids from the Tropical Starfish Asteropsis carinifera[J].Russ J Bioorg Chem+,2010,36(6):755-761.
[35]Ma N,Tang H F,Qiu F,et al.Polyhydroxysteroidal Glycosides from the Starfish Anthenea chinensis[J].J Nat Prod,2010,73(4):590-597.
[36]汤海峰,马宁,邱峰,等.中华五角海星中10个新的多羟基甾体苷及其肿瘤细胞毒性[C].//2010年中国药学大会暨第十届中国药师周论文集,2010:9.
[37]Kicha A A,Ivanchina N V,Huong T T T,et al.Two new asterosaponins,archasterosides A and B,from the Vietnamese starfish Archaster typicus and their anticancer properties[J].Bioorg Med Chem Lett,2010,20(12):3826-3830.
[38]Malyarenko T V,Kicha A A,Ivanchina N V,et al.Cariniferosides A-F and other steroidal biglycosides from the starfish Asteropsis carinifera[J].Steroids,2011,76(12):1280-1287.
[39]Hwang I H,Kim D W,Kim S J,et al.Asterosaponins lsolated from the Starfish Asterias amurensis[J].Chem Pharm Bull,2011,59(1):78-83.
[40]Thao N P,Cuong N X,Luyen B T,et al.Anti-inflammatory Asterosaponins from the Starfish Astropecten monacanthus[J].J Nat Prod,2013,76(9):1764-1770.
[41]Malyarenko T V,Kicha A A,Ivanchina N V,et al.Asterosaponins from the Far Eastern star?sh Leptasterias ochotensis and their anticancer activity[J].Steroids,2014,87(13):119-127.
[42]Malyarenko T V,Malyarenko O V,Ivanchina N V,et al.Four New Sulfated Polar Steroids from the Far Eastern Starfish Leptasterias ochotensis:Structures and Activities[J].Mar Drugs,2015,13(7):4418-4435.
[43]Kicha A A,Kalinovsky A I,Malyarenko T V,et al.Cyclic Steroid Glycosides from the Star?sh Echinaster luzonicus:Structures and Immunomodulatory Activities[J].J Nat Prod,2015,78(6):1397-1405.
[44]Kang J X,Kang Y F,Han H.Three New Cytotoxic Polyhydroxysteroidal Glycosides from Starfish Craspidaster hesperus[J].Mar Drugs,2016,14(10):189.
[45]Malyarenko T V,Kharchenko S D,Kicha A A,et al.Anthenosides L-U,Steroidal Glycosides with Unusual Structural Features from the Starfish Anthenea aspera[J].J Nat Prod,2016,79(12):3047-3056.
[46]Malyarenko T V,Kicha A A,Kalinovsky A I,et al.Four New Steroidal Glycosides,Protolinckiosides A-D,from the Starfish Protoreaster lincki[J].Chem Biodivers,2016,13:998-1007.
[47]Hanh T T,Vien L T,Vinh L B,et al.Further Highly Hydroxylated Steroids from the Vietnamese Star?sh Archaster typicus[J].Chem Pharm Bull,2016,64(10):1523-1527.
[48]Kicha A A,Kalinovsky A I,Ivanchina N V,et al.Furostane Series Asterosaponins and Other Unusual Steroid Oligoglycosides from the Tropical Starfish Pentaceraster regulus[J].J Nat Prod,2017,80(10):2761-2770.
[49]Malyarenko T V,Ivanchina N V,Malyarenko O S,et al.Two New Steroidal Monoglycosides,Anthenosides A1and A2,and Revision of the Structure of Known Anthenoside A with Unusual Monosaccharide Residue from the Starfish Anthenea aspera[J].Molecules,2018,23(5):1077.
[50]Lu Y,Li H,Wang M,et al.Cytotoxic Polyhydroxysteroidal Glycosides from Starfish Culcita novaeguineae[J].Mar Drugs,2018,16(3):92.