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Review

Manzamines

A potential for novel cures

, , &
Pages 1765-1772 | Published online: 01 May 2012

References

  • Sakai R, Higa T, Jefford CW, Bernardinelli G. Manzamine A, a Novel Antitumor Alkaloid from a Sponge. J Am Chem Soc 1986; 108:6404 - 5; http://dx.doi.org/10.1021/ja00280a055
  • Baldwin JE, Whitehead RC. On the biosynthesis of the manzamines. Tetrahedron Lett 1992; 33:2059 - 62; http://dx.doi.org/10.1016/0040-4039(92)88141-Q
  • Ohtani II, Ichiba T, Isobe M, Kelly-Borges M, Scheuer PJ. Kauluamine, an unprecedented manzamine dimer from an Indonesian marine sponge, Prianos sp. J Am Chem Soc 1995; 117:10743 - 4; http://dx.doi.org/10.1021/ja00148a017
  • El Sayed KA, Kelly M, Kara UAK, Ang KKH, Katsuyama I, Dunbar DC, et al. New manzamine alkaloids with potent activity against infectious diseases. J Am Chem Soc 2001; 123:1804 - 8; http://dx.doi.org/10.1021/ja002073o; PMID: 11456797
  • Peng J, Hu J-F, Kazi AB, Li Z, Avery M, Peraud O, et al. Manadomanzamines A and B: a novel alkaloid ring system with potent activity against mycobacteria and HIV-1. J Am Chem Soc 2003; 125:13382 - 6; http://dx.doi.org/10.1021/ja030087z; PMID: 14583033
  • Yousaf M, El Sayed KA, Rao KV, Lim CW, Hu JF, Kelly M, et al. 12,34-Oxamanzamines, novel biocatalytic and natural products from manzamine producing Indo-Pacific sponges. Tetrahedron 2002; 58:7397 - 402; http://dx.doi.org/10.1016/S0040-4020(02)00825-6
  • Sakai R, Kohmoto S, Higa T, Jefford CW. Bernardinelli Gr. Manzamine B and C, two novel alkaloids from the sponge haliclona sp. Tetrahedron Lett 1987; 28:5493 - 6; http://dx.doi.org/10.1016/S0040-4039(00)96762-5
  • Seki H, Nakagawa M, Hashimoto A, Hino T. The 1H- and 13C-Nuclear Magnetic Resonance Spectra of Manzamine C and Related Compounds. Chem Pharm Bull (Tokyo) 1993; 41:1173 - 6; http://dx.doi.org/10.1248/cpb.41.1173
  • Koren-Goldshlager G, Kashman Y, Schleyer M. Haliclorensin, a Novel Diamino Alkaloid from the Marine Sponge Haliclonatulearensis. J Nat Prod 1998; 61:282 - 4; http://dx.doi.org/10.1021/np970442x; PMID: 9548861
  • Guo Y, Trivellone E, Scognamiglio G, Cimino G. Misenine, a novel macrocyclic alkaloid with an unusual skeleton from the Mediterranean sponge Reniera sp. Tetrahedron 1998; 54:541 - 50; http://dx.doi.org/10.1016/S0040-4020(97)10314-3
  • Cimino G, Scognamiglio G, Spinella A, Trivellone E. Structural Studies on Saraine A. J Nat Prod 1990; 53:1519 - 25; http://dx.doi.org/10.1021/np50072a019
  • Ihara M, Fukumoto K. Recent progress in the chemistry of non-monoterpenoid indole alkaloids. Nat Prod Rep 1995; 12:277 - 301; http://dx.doi.org/10.1039/np9951200277
  • Kobayashi J, Tsuda M, Kawasaki N, Sasaki T, Mikami Y. 6-Hydroxymanzamine A and 3,4-dihydromanzamine A, new alkaloids from the Okinawan marine sponge Amphimedon Sp. J Nat Prod 1994; 57:1737 - 40; http://dx.doi.org/10.1021/np50114a021; PMID: 7714542
  • Tsuda M. Kobayashi Ji. Structures and Biogenesis of Manzamines and Related Alkaloids. Heterocycles 1997; 46:765 - 94; http://dx.doi.org/10.3987/REV-97-SR5
  • Watanabe D, Tsuda M, Kobayashi J. Three new manzamine congeners from amphimedon sponge. J Nat Prod 1998; 61:689 - 92; http://dx.doi.org/10.1021/np970564p; PMID: 9599281
  • Tsuda M, Watanabe D, Kobayashi JI. A New Manzamine Congener from Marine Sponge Amphimedon sp. 1999; 50:485-8.
  • Tsuda M, Watanabe D. Kobayashi Ji. Ma'eganedin A, a new manzamine alkaloid from Amphimedon sponge. Tetrahedron Lett 1998; 39:1207 - 10; http://dx.doi.org/10.1016/S0040-4039(97)10842-5
  • Kobayashi J, Tsuda M, Ishibashi M. Bioactive products from marine micro- and macro-organisms. Pure Appl Chem 1999; 71:1123 - 6; http://dx.doi.org/10.1351/pac199971061123
  • Tsuda M, Kawasaki N. Kobayashi Ji. Keramaphidin C and keramamine C plausible biogenetic precursors of manzamine C from an Okinawan marine sponge. Tetrahedron Lett 1994; 35:4387 - 8; http://dx.doi.org/10.1016/S0040-4039(00)73363-6
  • Tsuda M, Kawasaki N. Kobayashi Ji. Ircinols A and B, first antipodes of manzamine-related alkaloids from an Okinawan marine sponge. Tetrahedron 1994; 50:7957 - 60; http://dx.doi.org/10.1016/S0040-4020(01)85280-7
  • Ji K. Tsuda M, Kawasaki N, Matsumoto K, Adachi T. Keramaphidin B, a novel pentacyclic alkaloid from a marine sponge Amphimedon sp.: A plausible biogenetic precursor of manzamine alkaloids. Tetrahedron Lett 1994; 35:4383 - 6; http://dx.doi.org/10.1016/S0040-4039(00)73362-4
  • Ji K, Kawasaki N, Tsuda M. Absolute stereochemistry of keramaphidin B. Tetrahedron Lett 1996; 37:8203 - 4; http://dx.doi.org/10.1016/0040-4039(96)01861-8
  • Tsuda M, Inaba K, Kawasaki N, Honma K. Kobayashi Ji. Chiral resolution of (±)-keramaphidin B and isolation of manzamine L, a new Î2-carboline alkaloid from a sponge Amphimedon sp. Tetrahedron 1996; 52:2319 - 24; http://dx.doi.org/10.1016/0040-4020(95)01057-2
  • Ji K. Watanabe D, Kawasaki N, Tsuda M. Nakadomarin A, a Novel Hexacyclic Manzamine-Related Alkaloid from Amphimedon Sponge. J Org Chem 1997; 62:9236 - 9; http://dx.doi.org/10.1021/jo9715377
  • Crews P, Cheng X-C, Adamczeski M. RodrÃguez J, Jaspars M, Schmitz FJ, Traeger SC, Pordesimo EO. 1,2,3,4-tetrahydro-8-hydroxymanzamines, alkaloids from two different haplosclerid sponges. Tetrahedron 1994; 50:13567 - 74; http://dx.doi.org/10.1016/S0040-4020(01)85671-4
  • Ichiba T, Sakai R, Kohmoto S, Saucy G. New manzamine alkaloids from a sponge of the genus xestospongia. Tetrahedron Lett 1988; 29:3083 - 6; http://dx.doi.org/10.1016/0040-4039(88)85091-3
  • Kitagawa I, Kobayashi M. Antitumor Marine Natural Products. Yuki Gosei Kagaku Kyokaishi 1991; 49:1053 - 61; http://dx.doi.org/10.5059/yukigoseikyokaishi.49.1053
  • Kobayashi M, Chena Y-J, Aokia S, Inb Y, Ishidab T, Kitagawaa I. Four new β-carboline alkaloids isolated from two Okinawan marine sponges of Xestospongia sp. and Haliclona sp. Tetrahedron 1995; 51:3727 - 36; http://dx.doi.org/10.1016/0040-4020(95)95723-9
  • Rodriguez J, Crews P. Revised structure of xestocyclamine A and description of a new analogue. Tetrahedron Lett 1994; 35:4719 - 22; http://dx.doi.org/10.1016/S0040-4039(00)76950-4
  • Rodriguez J, Peters BM, Kurz L, Schatzman RC, McCarley D, Lou L, et al. An alkaloid protein kinase C inhibitor, xestocyclamine A, from the marine sponge Xestospongia sp. J Am Chem Soc 1993; 115:10436 - 7; http://dx.doi.org/10.1021/ja00075a100
  • Ohtani II, Ichiba T, Isobe M, Kelly-Borges M, Scheuer PJ. Kauluamine, an unprecedented manzamine dimer from an Indonesian marine sponge, Prianos sp. J Am Chem Soc 1995; 117:10743 - 4; http://dx.doi.org/10.1021/ja00148a017
  • Edrada RA, Proksch P, Wray V, Witte L, Müller WE, Van Soest RW. Four new bioactive manzamine-type alkaloids from the Philippine marine sponge Xestospongia ashmorica. J Nat Prod 1996; 59:1056 - 60; http://dx.doi.org/10.1021/np9604083; PMID: 8946747
  • Kong F, Andersen RJ, Allen TM. Ingamines A and B, new cytotoxic alkaloids from the marine sponge Xestospongia ingens. Tetrahedron 1994; 50:6137 - 44; http://dx.doi.org/10.1016/S0040-4020(01)80635-9
  • Kong F, Andersen RJ. Ingenamine alkaloids isolated from the sponge Xestospongia ingens: Structures and absolute configurations. Tetrahedron 1995; 51:2895 - 906; http://dx.doi.org/10.1016/0040-4020(95)00043-8
  • Kong F, Andersen RJ, Allen TM. Ingenamine, a novel pentacyclic alkaloid from the marine sponge Xestospongia ingens. Tetrahedron Lett 1994; 35:1643 - 6; http://dx.doi.org/10.1016/0040-4039(94)88308-4
  • Kong F, Andersen RJ, Allen TM. Madangamine A, a novel cytotoxic alkaloid from the marine sponge Xestospongia ingens. J Am Chem Soc 1994; 116:6007 - 8; http://dx.doi.org/10.1021/ja00092a077
  • Kong F, Graziani EI, Andersen RJ. Madangamines B-E, Pentacyclic Alkaloids from the Marine Sponge Xestospongia ingens.. J Nat Prod 1998; 61:267 - 71; http://dx.doi.org/10.1021/np970377r; PMID: 9548859
  • Kasanah N, Yousaf M, Rao KV, Wedge D, Hamann MT. The biocatalytic conversion of 8-hydroxymanzamine A to manzamine A using Fusarium solani. Tetrahedron Lett 2002; 44:1291 - 3; http://dx.doi.org/10.1016/S0040-4039(02)02816-2
  • Rao KV, Santarsiero BD, Mesecar AD, Schinazi RF, Tekwani BL, Hamann MT. New manzamine alkaloids with activity against infectious and tropical parasitic diseases from an Indonesian sponge. J Nat Prod 2003; 66:823 - 8; http://dx.doi.org/10.1021/np020592u; PMID: 12828469
  • Ichiba T, Corgiat JM, Scheuer PJ, Kelly-Borges M. 8-Hydroxymanzamine A, a beta-carboline alkaloid from a sponge, Pachypellina sp. J Nat Prod 1994; 57:168 - 70; http://dx.doi.org/10.1021/np50103a027; PMID: 8158160
  • Nakamura H, Deng S, Kobayashi J, Ohizumi Y, Tomotake Y, Matsuzaki T, et al. Physiologically active marine natural products from Porifera. XV. Keramamine-A and -B, novel antimicrobial alkaloids from the Okinawan marine sponge Pellina sp. Tetrahedron Lett 1987; 28:621 - 4; http://dx.doi.org/10.1016/S0040-4039(00)95796-4
  • Williams DE, Lassota P, Andersen RJ. Motuporamines A to C, Cytotoxic Alkaloids Isolated from the Marine Sponge Xestospongia exigua (Kirkpatrick). J Org Chem 1998; 63:4838 - 41; http://dx.doi.org/10.1021/jo980355p
  • Bourguet-Kondracki ML, Martin MT, Guyot M. A new β-carboline alkaloid isolated from the marine sponge Hyrtios erecta. Tetrahedron Lett 1996; 37:3457 - 60; http://dx.doi.org/10.1016/0040-4039(96)00573-4
  • Kondo K, Shigemori H, Kikuchi Y, Ishibashi M, Sasaki T, Kobayashi J. Ircinals A and B from the Okinawan Marine Sponge, Ircinia sp.: Plaisible Biogenetic Precoursors of Manzamine Alkaloids. Org Chem 1992; 57:2480 - 3; http://dx.doi.org/10.1021/jo00034a052
  • Zhou B-N, Slebodnick C, Johnson RK, Mattern MR, Kingston DGI. New Cytotoxic Manzamine Alkaloids from a Palaun Sponge. Tetrahedron 2000; 56:5781 - 4; http://dx.doi.org/10.1016/S0040-4020(00)00534-2
  • Williams DE, Craig KS, Patrick B, McHardy LM, van Soest R, Roberge M, et al. Motuporamines, anti-invasion and anti-angiogenic alkaloids from the marine sponge Xestospongia exigua (Kirkpatrick): isolation, structure elucidation, analogue synthesis, and conformational analysis. J Org Chem 2002; 67:245 - 58; http://dx.doi.org/10.1021/jo016101c; PMID: 11777468
  • Kasanah N, Rao K, Yousaf M, Wedge DE, Hill RT, Hamann MT. Biotransformation studies of the manzamine alkaloids. Mar Biotechnol (NY) 2004; 6:268 - 72
  • Higa T, Sakai R, Kohmoto S, Lui MS. Isolation of Antitumor Manzamines B, C, and D from Haliclona. In: application Ep, ed., 1988:44.
  • Toshima K, Ohta K, Ohashi A, Nakamura T, Nakata M, Tatsuta K, et al. Molecular Design, Chemical Synthesis, and Study of Novel Enediyne-Sulfide Systems Related to the Neocarzinostatin Chromophore. J Am Chem Soc 1995; 117:4822 - 31; http://dx.doi.org/10.1021/ja00122a012
  • El Sayed KA, Dunbar DC, Perry TL, Wilkins SP, Hamann MT, Greenplate JT, et al. Marine Natural Products as Prototype Insecticidal Agents. J Agric Food Chem 1997; 45:2735 - 9; http://dx.doi.org/10.1021/jf960746+
  • Mayer AMS, Gunasekera SP, Pomponi SA, Sennett SH. Anti-inflammatory uses of manzamine. US 2002.
  • Yousaf M, Hammond NL, Peng J, Wahyuono S, McIntosh KA, Charman WN, et al. New manzamine alkaloids from an Indo-Pacific sponge. Pharmacokinetics, oral availability, and the significant activity of several manzamines against HIV-I, AIDS opportunistic infections, and inflammatory diseases. J Med Chem 2004; 47:3512 - 7; http://dx.doi.org/10.1021/jm030475b; PMID: 15214779
  • Pc H, Frank P, Roggo S, Hamann MT. PCT International Patent Application. 2006:24.
  • Peng J, Rao KV, Choo YM, Hamann MT. Manzamine Alkaloids. Modern Alkaloids. Wiley-VCH Verlag GmbH & Co. KGaA. 2007:189-232.
  • Winkler JD, Axten JM. The First Total Syntheses of Ircinol A, Ircinal A, and Manzamines A and D. J Am Chem Soc 1998; 120:6425 - 6; http://dx.doi.org/10.1021/ja981303k
  • Peng J, Kudrimoti S, Prasanna S, Odde S, Doerksen RJ, Pennaka HK, et al. Structure-activity relationship and mechanism of action studies of manzamine analogues for the control of neuroinflammation and cerebral infections. J Med Chem 2010; 53:61 - 76; http://dx.doi.org/10.1021/jm900672t; PMID: 20017491
  • Magnier E. Langlois Yv. Manzamine Alkaloids, Syntheses and Synthetic Approaches. Tetrahedron 1998; 54:6201 - 58; http://dx.doi.org/10.1016/S0040-4020(98)00357-3
  • Hildebrand M, Waggoner LE, Lim GE, Sharp KH, Ridley CP, Haygood MG. Approaches to identify, clone, and express symbiont bioactive metabolite genes. Nat Prod Rep 2004; 21:122 - 42; http://dx.doi.org/10.1039/b302336m; PMID: 15039839
  • Abdelmohsen UR, Pimentel-Elardo SM, Hanora A, Radwan M, Abou-El-Ela SH, Ahmed S, et al. Isolation, phylogenetic analysis and anti-infective activity screening of marine sponge-associated actinomycetes. Mar Drugs 2010; 8:399 - 412; http://dx.doi.org/10.3390/md8030399; PMID: 20411105
  • Radwan M, Hanora A, Abo-Elmatty DM, Abou-El-Ela SH. Diversity of culturable actinobacteria isolated from two Red Sea sponges. Suez Canal Univ Med J 2009; 23
  • Radwan M, Hanora A, Zan J, Mohamed NM, Abo-Elmatty DM, Abou-El-Ela SH, et al. Bacterial community analyses of two Red Sea sponges. Mar Biotechnol (NY) 2010; 12:350 - 60; http://dx.doi.org/10.1007/s10126-009-9239-5; PMID: 19957096
  • Hentschel U, Usher KM, Taylor MW. Marine sponges as microbial fermenters. FEMS Microbiol Ecol 2006; 55:167 - 77; http://dx.doi.org/10.1111/j.1574-6941.2005.00046.x; PMID: 16420625
  • Piel J. Metabolites from symbiotic bacteria. Nat Prod Rep 2009; 26:338 - 62; http://dx.doi.org/10.1039/b703499g; PMID: 19240945
  • Fujii I. Heterologous expression systems for polyketide synthases. Nat Prod Rep 2009; 26:155 - 69; http://dx.doi.org/10.1039/b817092b; PMID: 19177221
  • Kao CM, Katz L, Khosla C. Engineered biosynthesis of a complete macrolactone in a heterologous host. Science 1994; 265:509 - 12; http://dx.doi.org/10.1126/science.8036492; PMID: 8036492
  • Wang Y, Boghigian BA, Pfeifer BA. Improving heterologous polyketide production in Escherichia coli by overexpression of an S-adenosylmethionine synthetase gene. Appl Microbiol Biotechnol 2007; 77:367 - 73; http://dx.doi.org/10.1007/s00253-007-1172-9; PMID: 17876579
  • Julien B, Shah S. Heterologous expression of epothilone biosynthetic genes in Myxococcus xanthus.. Antimicrob Agents Chemother 2002; 46:2772 - 8; http://dx.doi.org/10.1128/AAC.46.9.2772-2778.2002; PMID: 12183227
  • Mutka SC, Carney JR, Liu YQ, Kennedy J. Heterologous production of epothilone C and D in Escherichia coli.. Biochemistry 2006; 45:1321 - 30; http://dx.doi.org/10.1021/bi052075r; PMID: 16430229
  • Tang L, Shah S, Chung L, Carney J, Katz L, Khosla C, et al. Cloning and heterologous expression of the epothilone gene cluster. Science 2000; 287:640 - 2; http://dx.doi.org/10.1126/science.287.5453.640; PMID: 10649995
  • Pfeifer BA, Wang CCC, Walsh CT, Khosla C. Biosynthesis of Yersiniabactin, a complex polyketide-nonribosomal peptide, using Escherichia coli as a heterologous host. Appl Environ Microbiol 2003; 69:6698 - 702; http://dx.doi.org/10.1128/AEM.69.11.6698-6702.2003; PMID: 14602630
  • Jirakkakul J, Punya J, Pongpattanakitshote S, Paungmoung P, Vorapreeda N, Tachaleat A, et al. Identification of the nonribosomal peptide synthetase gene responsible for bassianolide synthesis in wood-decaying fungus Xylaria sp. BCC1067. Microbiology 2008; 154:995 - 1006; http://dx.doi.org/10.1099/mic.0.2007/013995-0; PMID: 18375793
  • Hanora A, Crow S. Exploring the Potential of Biosynthetic Gene Clusters in Sponge Associated Fungi from Red Sea, Egypt. New Egypt J Microbiol 2010; 27:182 - 98
  • Donadio S, Staver MJ, McAlpine JB, Swanson SJ, Katz L. Modular organization of genes required for complex polyketide biosynthesis. Science 1991; 252:675 - 9; http://dx.doi.org/10.1126/science.2024119; PMID: 2024119
  • Xue YQ, Zhao LS, Liu HW, Sherman DH. A gene cluster for macrolide antibiotic biosynthesis in Streptomyces venezuelae: architecture of metabolic diversity. Proc Natl Acad Sci USA 1998; 95:12111 - 6; http://dx.doi.org/10.1073/pnas.95.21.12111; PMID: 9770448
  • Julien B, Shah S, Ziermann R, Goldman R, Katz L, Khosla C. Isolation and characterization of the epothilone biosynthetic gene cluster from Sorangium cellulosum. Gene 2000; 249:153 - 60; http://dx.doi.org/10.1016/S0378-1119(00)00149-9; PMID: 10831849
  • Molnár I, Schupp T, Ono M, Zirkle RE, Milnamow M, Nowak-Thompson B, et al. The biosynthetic gene cluster for the microtubule-stabilizing agents epothilones A and B from Sorangium cellulosum So ce90. Chem Biol 2000; 7:97 - 109; http://dx.doi.org/10.1016/S1074-5521(00)00075-2; PMID: 10662695

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