Abstract
Water-soluble marine natural products are interesting as they generally do not penetrate into the cells but exhibit biological activities through cell surface receptors, ion channels, and glycans. Some molecules, however, interact with cell membrane and disrupt it. In this review, discovery, structures, and biological activities of water-soluble marine natural heterocyclic molecules are summarized with special emphasis on their biological activity and functions.
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References
Shimizu Y (1985) J Nat Prod 48:223–235
Sakai R, Swanson GT (2014) Nat Prod Rep 31:273–309
Olivera BM, Cruz LJ, Yoshikami D (1999) Curr Opin Neurobiol 9:772–777
Fritz L, Quilliam MA, Wright JL, Beale AM, Work TM (1992) J Phycol 28:439–442
Stathakis CI, Yioti EG, Gallos JK (2012) Eur J Org Chem 2012:4661–4673
Stonik VA, Stonik IV (2020) Molecules 25:3049
Toyota M, Spencer D, Sawai-Toyota S, Jiaqi W, Zhang T, Koo AJ, Howe GA, Gilroy S (2018) Science 361:1112–1115
Sakai R, Minato S, Koike K, Koike K, Jimbo M, Kamiya H (2005) Cell Tissue Res 322:491–502
Chekan JR, McKinnie SM, Moore ML, Poplawski SG, Michael TP, Moore BS (2019) Angew Chem 131:8542–8545
Brunson JK, McKinnie SM, Chekan JR, McCrow JP, Miles ZD, Bertrand EM, Bielinski VA, Luhavaya H, Oborník M, Smith GJ (2018) Science 361:1356–1358
Maeno Y, Kotaki Y, Terada R, Cho Y, Konoki K, Yotsu-Yamashita M (2018) Sci Rep 8:1–10
Lichtenthaler HK (2010) The non-mevalonate doxp/mep (deoxyxylulose 5-phosphate/methylerythritol 4-phosphate) pathway of chloroplast isoprenoid and pigment biosynthesis. In the chloroplast. Springer, Berlin, pp 95–118
Sakai R, Kamiya H, Murata M, Shimamoto K (1997) J Am Chem Soc 119:4112–4116
Sakai R, Suzuki K, Shimamoto K, Kamiya H (2004) J Org Chem 69:1180–1185
Sakai R, Kamiya H (2006) J Antibiot 59:507–511
IJzendoorn DR, Botman PN, Blaauw RH (2006) Org Lett 8:239–242
Sakai M, Ishikawa Y, Takamizawa S, Oikawa M (2013) Tetrahedron Lett 54:5911–5912
Tanaka K, Sakai M, Takamizawa S, Oikawa M (2015) Chem Lett 44:253–255
Ridley CP, Faulkner DJ, Haygood MG (2005) Appl Environ Microbiol 71:7366–7375
Sakai R, Yoshida K, Kimura A, Koike K, Jimbo M, Koike K, Kobiyama A, Kamiya H (2008) Chembiochem 9:543–551
Donia MS, Fricke WF, Partensky F, Cox J, Elshahawi SI, White JR, Phillippy AM, Schatz MC, Piel J, Haygood MG (2011) Proc Nat Acad Sci 108:E1423–E1432
Sakai R, Swanson GT, Shimamoto K, Green T, Contractor A, Ghetti A, Tamura-Horikawa Y, Oiwa C, Kamiya H (2001) J Pharmacol Exp Ther 296:650–658
Swanson GT, Green T, Sakai R, Contractor A, Che W, Kamiya H, Heinemann SF (2002) Neuron 34:589–598
Frydenvang K, Lash LL, Naur P, Postila PA, Pickering DS, Smith CM, Gajhede M, Sasaki M, Sakai R, Pentikaïnen OT (2009) J Biol Chem 284:14219–14229
Møllerud S, Frydenvang K, Pickering DS, Kastrup JS (2017) Neuropharmacology 112:16–28
Armstrong N, Gouaux E (2000) Neuron 28:165–181
Birdsey-Benson A, Gill A, Henderson LP, Madden DR (2010) J Neurosci 30:1463–1470
Qiu C-S, Lash-Van Wyhe L, Sasaki M, Sakai R, Swanson GT, Gereau IV RW (2011) Pain 152:1052–1060
Oikawa M, Ikoma M, Sasaki M, Gill MB, Swanson GT, Shimamoto K, Sakai R (2010) Bioorg Med Chem 18:3795–3804
Oikawa M, Kasori Y, Katayama L, Murakami E, Oikawa Y, Ishikawa Y (2013) Synthesis 45:3106–3117
Chiba M, Fujimoto C, Sakai R, Oikawa M (2015) Bioorg Med Chem Lett 25:1869–1871
Gill M, Frausto S, Ikoma M, Sasaki M, Oikawa M, Sakai R, Swanson GT (2010) Br J Pharmacol 160:1417–1429
Juknaite L, Sugamata Y, Tokiwa K, Ishikawa Y, Takamizawa S, Eng A, Sakai R, Pickering DS, Frydenvang K, Swanson GT (2013) J Med Chem 56:2283–2293
Sakai R, Matsubara H, Shimamoto K, Jimbo M, Kamiya H, Namikoshi M (2003) J Nat Prod 66:784–787
Evans SV, Shing TK, Aplin RT, Fellows LE, Fleet GW (1985) Phytochemistry 24:2593–2596
Mannaioni G, Alesiani M, Carlà V, Natalini B, Marinozzi M, Pellicciari R, Moroni F (1994) Eur J Pharmacol 251:201–207
Daly J (2007) Cell Mol Life Sci 64:2153–2169
Sakurada T, Gill MB, Frausto S, Copits B, Noguchi K, Shimamoto K, Swanson GT, Sakai R (2010) J Med Chem 53:6089–6099
Yu L, Coelho JE, Zhang X, Fu Y, Tillman A, Karaoz U, Fredholm BB, Weng Z, Chen J-F (2009) Physiol Genomics 37:199–210
Sakai R, Jares-Erijman EA, Manzanares I, Silva Elipe MV, Rinehart KL (1996) J Am Chem Soc 118:9017–9023
Schmidt EW, Donia MS (2010) Curr Opin Biotechnol 21:827–833
Taylor SW, Kammerer B, Bayer E (1997) Chem Rev 97:333–346
Uchimasu H, Matsumura K, Tsuda M, Kumagai K, Akakabe M, Fujita MJ, Sakai R (2016) Tetrahedron 72:7185–7193
Jinnai D, Sawai A, Mori A (1966) Nature 212:617–617
Godecke T, Lankin DC, Nikolic D, Chen S-N, van Breemen RB, Farnsworth NR, Pauli GF (2009) J Nat Prod 72:433–437
Van Wagoner RM, Jompa J, Tahir A, Ireland CM (1999) J Nat Prod 62:794–797
Davis RA, Duffy S, Avery VM, Camp D, Hooper JN, Quinn RJ (2010) Tetrahedron Lett 51:583–585
Akizawa T, Yamazaki K, Yasuhara T, Nakajima T, Roseghini M, Erspamer GF, Erspamer V (1982) Biomed Res 3:232–234
Cesar LM, Mendes MA, Tormena CF, Marques MR, De Souza BM, Saidemberg DM, Bittencourt JC, Palma MS (2005) Toxicon 46:786–796
Wang W, Takahashi O, Oda T, Nakazawa T, Ukai K, Mangindaan RE, Rotinsulu H, Wewengkang DS, Kobayashi H, Tsukamoto S (2009) Tetrahedron 65:9598–9603
Jiang C-S, Müller WE, Schröder HC, Guo Y-W (2012) Chem Rev 112:2179–2207
Tadokoro Y, Nishikawa T, Ichimori T, Matsunaga S, Fujita MJ, Sakai R (2017) ACS Omega 2:1074–1080
Miyako K, Yasuda Y, Shinada T, Fujita M, Sakai R (2020) J Nat Prod 83:3156–3165
Angelina E, Andujar S, Moreno L, Garibotto F, Párraga J, Peruchena N, Cabedo N, Villecco M, Cortes D, Enriz RD (2015) Mol Inform 34:28–43
Nagatsu T, Matsuura S, Sugimoto T (1989) Med Res Rev 9:25–44
Turk T, Frangež R, Sepčić K (2007) Mar Drugs 5:157–167
Laville R, Thomas OP, Berrue F, Reyes F, Amade P (2008) Eur J Org Chem 2008:121–125
Tribalat M-A, Marra MV, McCormack GP, Thomas OP (2016) Planta Med 82:843–856
Timm C, Volk C, Sasse F, Köck M (2008) Org Biomol Chem 6:4036–4040
Sepčić K, Guella G, Mancini I, Pietra F, Serra MD, Menestrina G, Tubbs K, Macek P, Turk T (1997) J Nat Prod 60:991–996
McClelland D, Evans R, Abidin I, Sharma S, Choudhry F, Jaspars M, Sepčić K, Scott RH (2003) Br J Pharmacol 139:1399–1408
Malovrh P, Sepčić K, Turk T, Maček P (1999) Comp Biochem Phys Part C Pharmacol Toxicol Endocrinol 124:221–226
McLaggan D, Adjimatera N, Sepčić K, Jaspars M, MacEwan DJ, Blagbrough IS, Scott RH (2006) BMC Biotechnol 6:6
Matsunaga S, Jimbo M, Gill MB, Wyhe LL, Murata M, Nonomura K, Swanson GT, Sakai R (2011) Chembiochem 12:2191–2200
Matsunaga S, Kishi R, Otsuka K, Fujita MJ, Oikawa M, Sakai R (2014) Org Lett 16:3090–3093
Matsunaga S, Sakai R, Jimbo M, Kamiya H (2007) Chembiochem 8:1729–1735
Kröger N, Deutzmann R, Sumper M (1999) Science 286:1129–1132
Shiozaki H, Miyahara M, Otsuka K, Miyako K, Honda A, Takasaki Y, Takamizawa S, Tukada H, Ishikawa Y, Sakai R (2018) Org Lett 20:3403–3407
Irie R, Miyahara M, Nakamura S, Honda A, Sakai R, Oikawa M (2020) J Nat Prod
Guillen PO, Jaramillo KB, Genta-Jouve G, Thomas OP (2020) Nat Prod Rep 37:515–540
Matsumura K, Taniguchi T, Reimer JD, Noguchi S, Fujita MJ, Sakai R (2018) Org Lett 20:3039–3043
Kinnel RB, Gehrken HP, Scheuer PJ (1993) J Am Chem Soc 115:3376–3377
Futaki S, Nakase I (2017) Acc Chem Res 50:2449–2456
Guillen PO, Jaramillo KB, Genta-Jouve G, Sinniger F, Rodriguez J, Thomas OP (2017) Org Lett 19:1558–1561
Oda Y, Zhang Q, Matsunaga S, Fujita MJ, Sakai R (2017) Chem Lett 46:1272–1274
Goto-Inoue N, Sato T, Morisasa M, Yamashita H, Maruyama T, Ikeda H, Sakai R (2020) Sci Rep 10:1–10
Oren A, Gunde-Cimerman N (2007) FEMS Microbiol Lett 269:1–10
Shinzato C, Shoguchi E, Kawashima T, Hamada M, Hisata K, Tanaka M, Fujie M, Fujiwara M, Koyanagi R, Ikuta T (2011) Nature 476:320–323
Acknowledgement
Researches conducted by RS are supported by JSPS grants 22380114, 15H04546, 18H02270, 19H03040, and 20H04758.
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Sakai, R. (2020). Chemical and Biological Aspects of Water-Soluble Heterocyclic Marine Natural Products. In: Kiyota, H. (eds) Marine Natural Products. Topics in Heterocyclic Chemistry, vol 58. Springer, Singapore. https://doi.org/10.1007/7081_2020_46
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DOI: https://doi.org/10.1007/7081_2020_46
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