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1 海葵化学成分及生物活性研究进展 Review of sea anemones compound and bioactivity 史文军 1, 秦松 3, 张朝晖 1,2 2, 吴建平 (1., ; 2., ; 3., ) 中图分类号 : R931.6 文献标识码 : A 文章编号 : (2013) (sea anemone), (Coelenterata) (Anthozoa) (actiniaria) 6 37 [1],,,, : (Anthopleura xanthogrammica) (A.pacifica) (Haliplanella luciae Hand) (Cereus sinensis Verrill), [2-3],,, Ap-A Ap-B, G- [4], ; [5], PsTX ; Tejuca [6] 3, 3,, [7], [8] 1 蛋白肽类成分与生物活性 ( ),,, [3] 1.1 神经毒类成分与生物活性, [2,9-10] Norton [11] 3, ~49, 6 3 ; 1 ApA ApB ATX II ; 2 RT I RT II 3 27~32,, 8 4 ; 3 DaI DaII ATX III 1 3, [12], 3, ~37, 6 3, 1 (Kv) [13] ; 1 Stichodactyla helianthus : ; : : ( AS ) : (1987-),,,, :, muzhiye080326@126.com;,, : , zzh6495@eyou.com 122 / 2013 / 37 / 12

2 ShK [14] Bunodosoma granulifera BgK [15] Anemonia erythraea AETX K [16] 2 3, 2 AsKC-1 AsKC-2 AsKC-3 [17] ; 3 Anemonia sulcata BDS-I BDS-II [18] Anthopleura elegantissima APETx1 [19] APETx2 [20] APHC1 [21],,, [22], α -,, [22-24] Cline E I [25] Urticina piscivora UpI, [26] Ap-QD1 Ap-QD2, 2 AP-A AP-B, Ap-QD1 Ap-QD2 [27] AP-Q, AP-Q I to I K I K 1, AP-Q rhk2a,,, [28] rhk2a N-, rhk2a,,, Stichodactyla helianthus ShK Kv1.3, Kv1.3 T B, ShK [29],,, : BcIV [30] AETX-II AETX-III [31], Am-I Am-II [32] BcIV Joacir Stolarz Oliveira B.caissarum, Callinectes danae, μg/kg Tomohiro Honma [33] Stichodactyla haddoni 4, SHTX I-IV, SHTX I-III, SHTXIV ; Tomohiro Honma [34] Dofleinia armata Entacmaea ramsay 2 3, 3, Kazuo Shiomi [35-36] Hiroshi Nagai [37] 1.2 溶细胞毒类成分与生物活性,,, 4 1 5~8 kda,, ; 2 20 kda,,, ; 3 30~40 kda, ; 4 80 kda,, [38-39], [40] Gary R. Grotendorst David A. Hessinger [41] Aiptasia pallida,, Yawen Wang [42] HMgIII, Wang, , min, 30%~100% Bragadeeswaran Subramanian [7] 4,, P.indicus H.magnifica P.sinensis ; S.haddoni Batista [43], EqtII 0.1 nmol/l V A,,, Jiang [44] SrcI BGC-823 BEL-7402 NSCIC, Abel Santamaria [45] Maria Cristina Pico [46] Elena V. Klyshko [47] Joacir Marine Sciences / Vol. 37, No. 12 /

3 Stolarz de Oliveira [48] 1.3 其他蛋白多肽类成分与生物活性 [49] (Src), Src (VCMC),, Src, 100 mg/l (VSMC) Src [50] Ant-5,, Kazuo Shiomi [36] gigantoxin I, 31%~33%, A431 gigantoxin I A431, Ricardo B. Cunha [51] CGX,,,, 8~12 h, CGX,, : Armando Alexei Rodriguez [52] Stichodactyla helianthus Bunodosoma granulifera, cdna, 5 APETx 5 1 Armando A.Rodriguez [53] ph Phymanthus crucifer, MALDI-TOF-MS, 2.0~3.5 kd Andre Junqueira Zaharenko [54] Bunodosoma cangicum, Sephadex G-50, 3, 3 1 : CGTX-II -AITX-Bcg1a -AITX- Bcg1b, 3, [55],, 1 48 AX-1, AX-1 - -,, Steve Peigneur [56] Anthopleura elegantissima, APEKTx1, , Kunitz APEKTx1 Kv1.1, 1 Mikiko Maeda [57] Cryptodendrum adhaesivum Heterodactyla hemprichii Thalassianthus aster 3, 3 ;, 1 -TLTX-Ca1a 2 - TLTX-Hh1a -TLTX-Hh1c 1 -TLTX- Ta1a,, 2 Andrej Razpotnik [58] Urticina crassicornis, Sephadex G-50, UcI, 30 kd 1, N-,,,,, 124 / 2013 / 37 / 12

4 表 1 部分蛋白质多肽类毒素氨基酸序列 Ap-A GVSCLCDSDGPSVRGNTLSGTLWLYPSGCPSGWHNCKAHGPTIGWCCCKQ Ap-B GVPCLCDSDGPRPRGNTLSGILWFYPSGCPSGWHNCKAHGPNIGWCCKK SHK RSCIDTIPKSRCIAICCKHSMKYRSICRKICGC BgK VCRDWFKETACRHAKSLCNCRTSCKYRANCAKTCELC AsKC-1 INKDCLLPMDVGRCRASHPRYYYNSSSKRCEKFIYGGCRGNANNFHTLEECEVCGVR AsKC-2 INKDCLLPMDVGRCRARHPRYYYNSSSRRCEKFIYGGCRGNANNFITKKECEKVCGVR AsKC-3 INGDCELPKVVGRCRARFPRYYYNLSSRRCEKFIYGGCGGNANNFHTLEECEKVCGVRS BDS-I AAPCFCSGKPGRGDLWILRGTCPGGYGYISNCYKWPNICCYPH BDS-II AAPCFCPGKPDRGDLWILRGTCPGGYGYTSNCYKWPNICCYPH APETx1 GTTCYCGKTIGIYWFGTKTCPSNRGYTGSCGYFLGICCYPVD BcIV GLPCDCCHGHTGTYWLNYYSKCPKGYGYTGRCRYLVGSCCYK APETx2 GTACSCGNSKGIYWFYRPSCPTDRGYTGSCRYFLGTCCTPAD Am-II ALLSCRCEGKTEYGDKWLFHGGCPNNYGYNYKCFMKPGAVCCYPQN CGTX-II GVACRCDSDGPTVRGDSLSGTLWLTGGCPSGWHNCRGSGPFIGYCCKK δ-aitx-bcg1a GVPCLCDSDGPSVRGNTLSGTVWVFGCPSGWHICTSDGPTIGSCCKK δ-aitx-bcg1b GVPCLCDSDGPSVRGDTLSGTVWVFGCPSGWHICTSDGPTIGSCCKK AX-1 GGVPCLCDSDGPSVRGNTLSGIIWLAGCPSGWHNCKAHGPTIGWCCKQ APEKTx1 INSICLLPKKQGFCRARFPRFYYNSSTRRCEMFYYGGCGGGNANNFNTLEECEKVCLGYGEA WKAP δ-tltx-ca1a VACKCDDDGPDVRSATFTGTVDLGSCNSGWEKCASYYTVIADCCRKPRG δ-tltx-ta1a VACKCDDDGPDIRSATLTGTVDLGSCDEGWEKCASYYTVIADCCRRPRS,,,, pi 8.0, 4 pi 5.0,, [39],, 2 酰胺类成分与生物活性 [59-61], Anthcpleura pacifica,, 7 ( 1) : 2S, 3R, 4 (E), 8 (E)- - (1) 2S, 3R, 4 (E), 8 (E)- - (2) 4,5 (E), 8,9 (E)- - (3) N- -N- -(2S, 3R)- -4(E), 8(E)- (4) N- -N-(9Z- )-(2S, 3R)- -4(E), 8(E)- (5) N- - N- -(2S, 3R)- -4(E), 8(E )- (6) N- -N-(13Z- )-(2S, 3R)- - 4(E), 8(E)- (7) 2S, 3R, 4 (E), 8 (E)- - 2S, 3R, 4 (E), 8 (E)- - 4,5 (E), 8,9 (E)- - N- -N- -(2S, 3R)- - 4(E), 8(E )- [62] 4,5 (E), 8,9 (E)- - 3 甾体类成分与生物活性 [60] Anthcpleura pacifica 5α, , (8), 2 4 糖和糖苷类成分与生物活性 [63] Marine Sciences / Vol. 37, No. 12 /

5 1 [65] Anthopleura midori [66] Anthopleura xanthogrammica (9), 3 2 Zoanthus stephensoni, 2, 2 2, I, ; II,, [64] 3 5 脂肪酸和甘油酯类成分与生物活性 [67] Anthopleura xanthogrammica / 2013 / 37 / 12

6 ( 4), 2 : 9,12- (10) 9,14- (11); 3 :1-o- -2-o-(9- )-3-o-(9,12- ) (12) 1-o- -3-o-(14- ) (13) 1-o-(9,12- )-2-o-(9,12- ) (14) [59] Anthcpleura pacifica : (15) (16) 1-o- (17) [62] SD, (8 mg/kg), ; (33 mg/kg), 4 6 生物碱类成分与生物活性 [68] HPLC Haliplanella luciae Hand, 3 ( 5): tryptoline(18) (19) - (20); 1 : (21), 5 Marine Sciences / Vol. 37, No. 12 /

7 7 结语 5,,,,,,,, ;,,,, [69-72], : [1],,,. [J]., 2002, 3: [2],. [J]., 2008, 27(2): [3],. [J]., 1987, 4: [4]. [J]., 2004, 26(2): [5],,,. [J]., 2006, 23(5): [6] Tejuca M, Anderluh G, Dalla Serra M. Sea anemone cytolysins as toxic components of immunotoxins[j]. Toxion, 2009, 54(8): [7] Bragadeeswaran Subramanian, Thangaraj Sangappellai, Rajiv Chandra Rajak, et al. Pharmacological and biomedical properties of sea anemones Paracondactylis indicus, Paracondactylis sinensis, Heteractis magnifica and Stichodactyla haddoni from East coast of India[J]. Asian Pacif J Tropl Med, 2011, 4(9): [8]. [M]. :, 1990: 284. [9],,,. [J]., 2011, 29(1): [10],,,. [J]., 2000, 2: [11] Norton R S. Structure and structure-function relationships of sea anemone proteins that interact with the sodium channel[j]. Toxicon, 1991, 29(9): [12] Yehu Moran, Dalia Gordon, Michael Gurevitz. Sea anemone toxins affecting voltage-gated sodium channels-molecular and evolutionary features[j]. Toxicon, 2009, 54(8): [13] Middleton R E, Sanchez M, Linde A R, et al. Substitution of a single residue in Stichodactyla helianthus peptide,shk-dap22, reveals a novel pharmacological profile[j]. Biochemistry, 2003, 42(46): [14] Castaneda O, Sotolongo V, Amor A M, et al. Characterization of a potassium channel toxin from the Caribbean sea anemone Stichodactyla helianthus[j]. Toxicon, 1995, 33(5): [15] Cotton J, Crest M, Bouet F, et al. A potassium-channel toxin from the sea anemone Bunodosoma granulifera, an inhibitor for Kv1 channels, revision of the amino acid sequence, disulfide-bridge assignment, chemical synthesis, and biological activity[j]. Eur J Biochem, 1997, 244(1): [16] Hasegawa Y, Honma T, Nagai H, et al. Isolation and 128 / 2013 / 37 / 12

8 cdna cloning of a potassium channel peptide toxin from the sea anemone Anemonia erythraea[j]. Toxicon, 2006, 48(5): [17] Schweitz H, Bruhn T, Guillemare E, et al. Kalicludines and kaliseptine. Two different classes of sea anemone toxins for voltage-sensitive K + channels[j]. J Biol Chem, 1995, 270(42): [18] Diochot S, Schweitz H, Beress L, et al. Sea anemone peptides with a specific blocking activity against the fast inactivating potassium channel Kv3.4[J]. J Biol Chem, 1998, 273(12): [19] Diochot S, Loret E, Bruhn T, et al. APETx1, a new toxin from the sea anemone Anthopleura elegantissima, blocks voltage-gated human ether-a-go-go-related gene potassium channels[j]. Mol Pharmacol, 2003, 64(1): [20] Diochot S, Baron A, Rash L D, et al. A new sea anemone peptide, APETx2, inhibits ASIC3, a major acid-sensitive channel in sensory neurons[j]. Embo J, 2004, 23(7): [21] Andreev Y A, Kozlov S A, Koshelev S G, et al. Analgesic compound from sea anemone Heteractis crispa is the first polypeptide inhibitor of vaniloid receptor 1 (TRPV1)[J]. J Biol Chem, 2008, 283(35): [22] Schw eit Z H, Vincent J P, Barhanin J, et al. Purification and pharmacological properties of eight sea anemone toxins from Anemonia sulcata, Anthopleura xanthogrammica, Stoichactis giganteus and Actinodendron plumosum[j]. Biochemistry, 1981, 20(18): [23],. Anthopleura xanthogrammica A. Elegantissima [J]., 1982, 2: [24] Micheal J G, Kenneth M B. Cloning and expression of wild-thpe and mutant forms of the cardiotonic polypeptide anthopleurin-b[j]. J Biol Chem, 1992, 267(20): [25] Cline E I, Wolowyk M W, Wiebe L I, et al. Isolation and characterization of a novel cardiac stimulatory and hemolytic protein from the sea anemone Urticina piscivora(sebens and Laakso)[J]. Pharm Sci, 1995, 1(4): [26],,,. [J]., 1996, 35(6): [27],,,. [J]., 2009, 44(21): [28],,,. [J]., 2011, 28(7): [29] Victor Chi, Pennington M W, Norton R S, et al. Development of a sea anemone toxin as an immunomodulator for therapy of autoimmune diseases[j]. Toxicon, 2012, 59(4): [30] Joacir Stolarz Oliveira, Andre Junqueira Zaharenko, Wilson Alves Ferreira Jr, et al. BcIV, a new paralyzing peptide obtained from the venom of the sea anemone Bunodosoma caissarum A comparison with the Na + channel toxin BcI II[J]. Biochim Biophys Acta, 2006, 1764(10): [31] Shiomi K, Qian W H, Lin X Y, et al. Novel polypeptide toxins with crab toxicity from the sea anemone Anemonia erythraea[j]. Biochim Biophys Acta, 1997, 1335(1-2): [32] Honma T, Hasegawa Y, Ishida M, et al. Isolation and molecular cloning of novel peptide toxins from the sea anemone Antheopsis maculata[j]. Toxicon, 2005a, 45(1): [33] Tomohiro Honma, Shino Kawahata, Masami Ishida, et al. Novel peptide toxins from the sea anemone Stichodactyla haddoni[j]. Peptides, 2008, 29(4): [34] Tomohiro Honma, Takeshi Iso, Masami Ishida, et al. Occurrence of type 3 sodium channel peptide toxins in two species of sea anemones (Dofleinia armata and Entacmaea ramsayi)[j]. Toxicon,2003, 41(5): [35] Kazuo Shiomi, Wen Hong Qian, Xin Yu Lin, et al. Novel polypeptide toxins with crab lethality from the sea anemone Anemonia erythraea[j]. Biochim Biophys Acta, 1997, 1335(1-2): Marine Sciences / Vol. 37, No. 12 /

9 [36] Kazuo Shiomi, Tomohiro Honmaa, Masao Ide, et al. An epidermal growth factor-like toxin and two sodium channel toxins from the sea anemone Stichodactyla gigantea[j]. Toxion, 2003, 41(2): [37] Hiroshi Nagai, Naomasa Oshiro, Kyoko Takuwa- Kuroda, et al. Novel proteinaceous toxins from the nematocyst venom of the Okinawan sea anemone Phyllodiscus semoni Kwietniewski[J]. Biochem Biophys Res Commun, 2002, 294(4): [38] Heidi Irais Monroy-Estrada, Lourdes Segura-Puertas, Sonia Galvan-Arzate, et al. The crude venom from the sea anemone Stichodactyla helianthus induces haemolysis and slight peroxidative damage in rat and human erythrocytes[j]. Toxicology in Vitro, 2007, 21(3): [39] Gregor Anderluh, Peter Macek. Cytolytic peptide and protein toxion from sea anemones(anthozoa: Actiniaria)[J]. Toxion, 2002, 40(2): [40],,,. [J]., 2005, 29(4): [41] Gary R Grotendorst, David A Hessinger. Purification and partial characterization of the phospholipase A 2 and cytolytic factor from sea anemone (Aiptasia pallida) nematocyst venom[j]. Toxicon, 1999, 37(12): [42] Yawen Wang, Kim Lee Chua, Hoon Eng Khoo. A new cytolysin from the sea anemone, Heteractis magnica: isolation, cdna cloning and functional expression[j]. Biochim Biophys Acta, 2000, 1478(1): [43] Batista U, Jezernik K. Morphological changes of V-79 cells after equinatoxin II treatment[j]. Cell Biol, 1992, 16(2): [44] Jiang X Y, Yang W L, Chen H P, et al. Cloning and characterization of an acidic cytolysin cdna from sea anemone Sagartia rosea[j]. Toxicon, 2002, 40(11): [45] Abel Santamaria, Judith Sanchez-Rodrıguez, Alejandro Zugasti, et al. A venom extract from the sea anemone Bartholomea annulata produces haemolysis and lipid peroxidation in mouse erythrocytes[j]. Toxicology, 2002, 173(3): [46] Maria Cristina Pico, Ariel Basulto, Alberto del Monte, et al. Cross-reactivity and inhibition of haemolysis by polyclonal antibodies raised against St II, a cytolysin from the sea anemone Stichodactyla helianthus[j]. Toxicon, 2004, 43(2): [47] Elena V Klyshko, Marina P Issaeva, Margarita M Monastyrnaya, et al. Isolation, properties and partial amino acid sequence of a new actinoporin from the sea anemone Radianthus macrodactylus[j]. Toxicon, 2004, 44(3): [48] Joacir Stolarz de Oliveira, André Junqueira Zaharenko, José Carlos de Freitas, et al. Caissarolysin I(Bcs I), a new hemolytic toxin from the Brazilian sea anemone Bunodosoma caissarum: Purification and biological characterization[j]. Biochim Biophys Acta, 2006, 1760(3): [49],,,. [J]., 2002, 22(11): [50],,,. 22 [J]., 2003, 19(11): [51] Cunha R B, Santana A N C, Amaral P C, et al. Primary structure, behavioral and electroencephalographic effects of an epileptogenic peptide from the sea anemone Bunodosoma cangicum[j]. Toxicon, 2005, 45(2): [52] Armando Alexei Rodriguez, Juliana Silva Cassoli, Zhi Qiang Dong, et al. Peptide fingerprinting of the neurotoxic fractions isolated from the secretions of sea anemones Stichodactyla helianthus and Bunodosoma granulifera. New members of the APETx-like family identified by a 454 pyrosequencing approach[j]. Petides, 2012, 34(1): [53] Armando A Rodriguez, Ludger Standker, Andre J Zharenko, et al. Combining multidimensional liquid chromatography and MALDI TOF-MS for the fingerprint analysis of secreted peptides from the unexplored sea anemone species Phymanthus crucifer [J]. J Chromatogr B, 2012, 903(1-2): [54] André Junqueira Zaharenko, Emanuele Schiavon, Wilson Alves Ferreira Jr, et al. Characterization of 130 / 2013 / 37 / 12

10 selectivity and pharmacophores of type 1 sea anemone toxins by screening seven Nav sodium channel isoforms[j]. Peptides, 2012, 34(1): [55],,,. AX-1 [J]., 2012, 31(2): [56] Steve Peigneur, Bert Billen, Rita Derua, et al. A bifunctional sea anemone peptide with Kunitz type protease and potassium channel inhibiting properties[j]. Biochem Pharmacol, 2011, 82(1): [57] Mikiko Maeda, Tomohiro Honma, Kazuo Shiomi. Isolation and cdna cloning of type 2 sodium channel peptide toxins from three species of sea anemones (Cryptodendrum adhaesivum, Heterodactyla hemprichii and Thalassianthus aster) belonging to the family Thalassianthidae[J]. Comp Biochem Physiol B, 2010, 157(4): [58] Andrej Razpotnik, Igor Krizaj, William R Kem, et al. A new cytolytic protein from the sea anemone Urticina crassicornis that binds to cholesterol-and sphingomyelin-rich membranes[j]. Toxicon, 2009, 53(7-8): [59],,,. (III)[J]., 2003, 18(1): [60],,,. (I)[J]., 2002, 23(3): [61],,,. [J]., 2003, 38(5): [62],,,. [J]., 2010, 32(3): [63],,,. I II [J]., 1991, 3: [64],,,. [J]., 1991, 4: [65],,,. [J]., 2001, 14(14): [66],,,. (I)[J]., 1998, 1: [67],,. (II)[J]., 1998, 3: [68],,,. [J]., 2010, 29(1): [69],,,. (Cereus sinensis Verrill) ( )[J]., 2011, 3: [70],,,. [J]., 2011, 32(4): [71],,,. (Cereus sinensis Verrill) ( )[J]., 2011, 4: 72. [72],,,. [J]., 2011, 20(6): ( 本文编辑 : 康亦兼 ) Marine Sciences / Vol. 37, No. 12 /

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