Abstract
This review covers the recent results described in our publications on several new cytotoxic macrolides isolated from dinoflagellates of the genus Amphidinium in addition to an overview of the isolation, structure elucidation, synthesis, biosynthesis, and bioactivity of a series of cytotoxic macrolides, named amphidinolides, reported so far.
Similar content being viewed by others
Article PDF
References
Kobayashi J, Ishibashi M . Bioactive metabolites of symbiotic marine microorganisms. Chem Rev 93: 1753–1769 ( 1993)
Kobayashi J, Ishibashi M . Amphidinolides: Unique macrolides from marine dinoflagellates. Heterocycles 44: 543–572 ( 1997)
Ishibashi M, Kobayashi J . Miscellaneous natural products including marine products, pheromones, plant hormones, and aspects of ecology. In: Mori K (ed). Comprehensive Natural Products Chemistry, Vol. 8. Elsevier Science, Oxford, pp. 415–650 ( 1999)
Kobayashi J, Tsuda M, Ishibashi M . Bioactive products from marine micro- and macro-organisms. Pure Appl Chem 71: 1123–1126 ( 1999)
Kobayashi J, Shimbo K, Kubota T, Tsuda M . Bioactive macrolides and polyketides from marine dinoflagellates. Pure Appl Chem 75: 337–342 ( 2003)
Kobayashi J, Tsuda M . Amphidinolides, bioactive macrolides from symbiotic marine dinoflagellates. Nat Prod Rep 21: 77–93 ( 2004)
Kobayashi J, Kubota T . Bioactive macrolides and polyketides from marine dinoflagellates of the genus Amphidinium. J Nat Prod 70: 451–460 ( 2007)
Chakraborty TK, Das S . Chemistry of potent anti-cancer compounds, amphidinolides. Curr Med Chem Anti-cancer Agents 1: 131–149 ( 2001)
Moore BS . Biosynthesis of marine natural products: microorganisms and macroalgae. Nat Prod Rep 16: 653–674 ( 1999)
Shimizu Y . Microalgal metabolites. Curr Opin Microbiol 6: 236–243 ( 2003)
Daranas AH, Norte M, Fernandez JJ . Toxic marine microalgae. Toxicon 39: 1101–1132 ( 2001)
Rein KS, Borrone J . Polyketides from dinoflagellates: origins, pharmacology and biosynthesis. Comp Biotechnol Physiol B: Biochem Mol Biol 124: 117–131 ( 1999)
Yasumoto T, Satake M . Bioactive compounds from marine microalgae. Chimia 52: 63–68 ( 1998)
Yasumoto T, Satake M . Chemistry, etiology and determination methods of ciguatera toxins. J Toxicol Toxin Rev 15: 91–107 ( 1996)
Takahashi Y, Kubota T, Kobayashi J . Amphidinolactone A, a new 13-membered macrolide from dinoflagellate Amphidinium sp. Heterocycles 72: 567–572 ( 2007)
Takahashi Y, Kubota T, Kobayashi J . Amphidinolactone B, a new 26-membered macrolide from dinoflagellate Amphidinium sp. J Antibiot 60: 376–379 ( 2007)
Tsuda M, Oguchi K, Iwamoto R, Okamoto Y, Kobayashi J, Fukushi E, Kawabata J, Ozawa T, Masuda A, Kitaya Y, Omasa K . Iriomoteolide-1a, a potent cytotoxic 20-membered macrolide from a benthic dinoflagellate Amphidinium species. J Org Chem 72: 4469–4474 ( 2007)
Tsuda M, Oguchi K, Iwamoto R, Okamoto Y, Fukushi E, Kawabata J, Ozawa T, Masuda A . Iriomoteolides-1b and -1c, 20-membered macrolides from a marine dinoflagellate Amphidinium species. J Nat Prod 70: 1661–1663 ( 2007)
Tsuda M, Endo T, Kobayashi J . Amphidinolide T, novel 19-membered macrolide from marine dinoflagellate Amphidinium sp. J Org Chem 65: 1349–1352 ( 2000)
Kobayashi J, Kubota T, Endo T, Tsuda M . Amphidinolides T2, T3, and T4, new 19-membered macrolides from the dinoflagellate Amphidinium sp. and the biosynthesis of amphidinolide T1. J Org Chem 66: 134–142 ( 2001)
Oguchi K, Tsuda M, Iwamoto R, Okamoto Y, Endo T, Kobayashi J, Ozawa T, Masuda A . Amphidinolides B6 and B7, cytotoxic macrolides from a symbiotic dinoflagellate Amphidinium species. J Nat Prod 70: 1676–1679 ( 2007)
Kobayashi J, Shimbo K, Sato M, Tsuda M . Amphidinolides H2~H5, G2, and G3, new cytotoxic 26- and 27-membered macrolides from dinoflagellate Amphidinium sp. J Org Chem 67: 6585–6592 ( 2002)
Tsuda M, Kariya Y, Iwamoto R, Fukushi E, Kawabata J, Kobayashi J . Amphidinolides B4 and B5, potent cytotoxic 26-membered. macrolides from dinoflagellate Amphidinium species. Mar Drugs 3: 1–8 ( 2005)
Kobayashi J, Ishibashi M, Murayama T, Takamatsu M, Iwamura M, Ohizumi Y, Sasaki T . Amphidinolide E, a novel antileukemic 19-membered macrolide from the cultured symbiotic dinoflagellate Amphidinium sp. J Org Chem 55: 3421–3423 ( 1990)
Kobayashi J, Shigemori H, Ishibashi M, Yamasu T, Hirota H, Sasaki T . Amphidinolides G and H: New potent cytotoxic macrolides from the cultured symbiotic dinoflagellate Amphidinium sp. J Org Chem 56: 5221–5224 ( 1991)
Kobayashi J, Shimbo K, Sato M, Shiro M, Tsuda M . Absolute stereochemistry of amphidinolides G and H. Org Lett 2: 2805–2807 ( 2000)
Oguchi K, Tsuda M, Iwamoto R, Okamoto Y, Kobayashi J, Fukushi E, Kawabata J, Ozawa T, Masuda A, Kitaya Y, Omasa K . Iriomoteolide-3a, a cytotoxic 15-membered macrolide from a marine dinoflagellate Amphidinium species. J Org Chem 73: 1567–1570 ( 2008)
Kubota T, Tsuda M, Kobayashi J . Absolute stereochemistry of amphidinolide E. J Org Chem 67: 1651–1656 ( 2002)
Va P, Roush WR . Total synthesis of amphidinolide E. J Am Chem Soc 128: 15960–15961 ( 2006)
Kim CH, An HJ, Shin WK, Yu W, Woo SK, Jung SK, Lee E . Total synthesis of (−)-amphidinolide E. Angew Chem Int Ed 45: 8019–8021 ( 2006)
Fürstner A, Bouchez LC, Fune JA, Liepins V, Porée FH, Gilmour R, Beaufils F, Laurich D, Tamiya M . Total syntheses of amphidinolide H and G. Angew Chem Int Ed 46: 9265–9270 ( 2007)
Kubota T, Tsuda M, Kobayashi J . Amphidinolide V, novel 14-membered macrolide from marine dinoflagellate Amphidinium sp. Tetrahedron Lett 41: 713–716 ( 2000)
Fürstner A, Larionov O, Flügge S . What is Amphidinolide V? Report on a likely conquest. Angew Chem Int Ed 46: 5545–5548 ( 2007)
Ishibashi M, Yamaguchi N, Sasaki T, Kobayashi J . Amphidinolide N, a novel 26-membered macrolide with remarkably potent cytotoxicity from the cultured marine dinoflagellate Amphidinium sp. J Chem Soc Chem Commun 1994: 1445–1446 ( 1994)
Bauer I, Maranda L, Young KA, Shimizu Y, Fairchild C, Cornell L, MacBeth J, Huang S . Isolation and structure of caribenolide I, a highly potent antitumor macrolide from a cultured free-swimming caribbean dinoflagellate, Amphidinium sp. S1-36-5. J Org Chem 60: 1084–1086 ( 1995)
Nicolaou KC, Brenzovich WE, Bulger PG, Francis TM . Synthesis of iso-epoxy-amphidinolide N and des-epoxy-caribenolide I structures. Initial forays. Org Biomol Chem 4: 2119–2157 ( 2006)
Nicolaou KC, Bulger PG, Brenzovich WE . Synthesis of iso-epoxy-amphidinolide N and des-epoxy-caribenolide I structures. Revised strategy and final stages. Org Biomol Chem 4: 2158–2183 ( 2006)
Seck M, Frank X, Seon-Meniel B, Hocquemiller R, Figadere B . A Baylis-Hillman approach to the synthesis of C1~C11 fragment of caribenolide I. Tetrahedron Lett 47: 4175–4180 ( 2006)
Jalce G, Frank X, Seon-Meniel B, Hocquemiller R, Figadére B . Contribution to the total synthesis of caribenolide I. Tetrahedron Lett 47: 5905–5908 ( 2006)
Tsuda M, Izui N, Shimbo K, Sato M, Fukushi E, Kawabata J, Katsumata K, Horiguchi T, Kobayashi J . Amphidinolide X, a novel 16-membered macrodiolide from dinoflagellate Amphidinium sp. J Org Chem 68: 5339–5345 ( 2003)
Tsuda M, Izui N, Shimbo K, Sato M, Fukushi E, Kawabata J, Kobayashi J . Amphidinolide Y, a novel 17-membered macrolide from dinoflagellate Amphidinium sp.: Plausible biogenetic precursor of amphidinolide X. J Org Chem 68: 9109–9112 ( 2003)
Fürstner A, Kattnig E, Lepage O . Total syntheses of amphidinolide X and Y. J Am Chem Soc 128: 9194–9204 ( 2006)
Jin J, Chen Y, Li Y, Wu J, Dai WM . Total synthesis of amphidinolide Y by formation of trisubstituted (E)-double bond via ring-closing metathesis of densely functionalized alkenes. Org Lett 9: 2585–2588 ( 2007)
Matsunaga K, Nakatani K, Ishibashi M, Kobayashi J, Ohizumi Y . Amphidinolide B, a powerful activator of actomyosin ATPase enhances skeletal muscle contraction. Biochimica et Biophysica Acta 1427: 24–32 ( 1999)
Usui T, Kazami S, Dohmae N, Mashimo Y, Kondo H, Tsuda M, Terasaki GA, Ohashi K, Kobayashi J, Osada H . Amphidinolide H, a potent cytotoxic macrolide, covalently binds on actin subdomain 4 and stabilizes actin filament. Chem Biol 11: 1269–1277 ( 2004)
Saito S, Feng J, Kira A, Kobayashi J, Ohizumi Y . Amphidinolide H, a novel type of actin-stabilizing agent isolated from dinoflagellate. Biochem Biophys Res Commun 320: 961–965 ( 2004)
Houdai T, Matsuoka S, Murata M, Satake M, Ota S, Oshima Y, Rhodes L . Acetate labeling patterns of dinoflagellate polyketides, amphidinols 2, 3 and 4. Tetrahedron 57: 5551–5555 ( 2001)
Edwards DJ, Marquez BL, Nogle LM, Mcphail K, Goeger DE, Roberts MA, Gerwick WH . Structure and biosynthesis of the jamaicamides, new mixed polyketide-peptide neurotoxins from the marine cyanobacterium Lyngbya majuscula. Chem Biol 11: 817–833 ( 2004)
Hothersall J, Wu J, Rahman AS, Shields JA, Haddock J, Johnson N, Cooper SM, Stephens ER, Cox RJ, Crosby J, Willis CL, Simpson TJ, Thomas CM . Mutational analysis reveals that all tailoring region genes are required for production of polyketide antibiotic mupirocin by Pseudomonas fluorescens: Pseudomonic acid B biosynthesis precedes pseudomonic acid A. J Biol Chem 282: 15451–15461 ( 2007)
Gu L, Jia J, Liu H, Hakansson K, Gerwick WH, Sherman DH . Metabolic coupling of dehydration and decarboxylation in the curacin A pathway: Functional identification of a mechanistically diverse enzyme pair. J Am Chem Soc 128: 9014–9015 ( 2006)
Snyder RV, Gibbs PDL, Palacios A, Abiy L, Dickey R, Lopez JV, Rein KS . Polyketide synthase genes from marine dinoflagellates. Mar Biotechnol 5: 1–12 ( 2003)
Snyder RV, Guerrero MA, Sinigalliano CD, Winshell J, Perez R, Lopez JV, Rein KS . Localization of polyketide synthase encoding genes to the toxic dinoflagellate Karenia brevis. Phytochemistry 66: 1767–1780 ( 2005)
Kubota T, Iinuma Y, Kobayashi J . Cloning of polyketide synthase genes from amphidinolide-producing dinoflagellate Amphidinium sp. Biol Pharm Bull 29: 1314–1318 ( 2006)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kobayashi, J. Amphidinolides and Its Related Macrolides from Marine Dinoflagellates. J Antibiot 61, 271–284 (2008). https://doi.org/10.1038/ja.2008.39
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1038/ja.2008.39
Keywords
This article is cited by
-
Effects of substratum and depth on benthic harmful dinoflagellate assemblages
Scientific Reports (2020)
-
New molecular insights on the response of the green alga Tetraselmis suecica to nitrogen starvation
Scientific Reports (2019)
-
Morphology, growth, toxin production, and toxicity of cultured marine benthic dinoflagellates from Brazil and Cuba
Journal of Applied Phycology (2019)
-
De novo transcriptome of the cosmopolitan dinoflagellate Amphidinium carterae to identify enzymes with biotechnological potential
Scientific Reports (2017)
-
Iriomoteolides-9a and 11a: two new odd-numbered macrolides from the marine dinoflagellate Amphidinium species
Journal of Natural Medicines (2017)