Pyridoacridine alkaloids from deep-water marine organisms: Structural elucidation

Ding, 1999, Pyrroloquinoline and pyridoacridine alkaloids from marine sources, Curr Med Chem, 6, 1, 10.2174/0929867306666220207205410 Groundwater, 1998, Heterocycle-fused acridines, Adv Heterocyclic Chem, 70, 89, 10.1016/S0065-2725(08)60930-7 Molinski, 1993, Marine pyridoacridine alkaloids: structure, synthesis, and biological chemistry, Chem Rev, 93, 1825, 10.1021/cr00021a009 Marshall, 2004, Biological activities of pyridoacridines, Nat Prod Rep, 21, 731, 10.1039/b401662a Ibrahim, 2016, Marine pyridoacridine alkaloids: biosynthesis and biological activities, Chem Biodivers, 13, 37, 10.1002/cbdv.201400434 Viracaoundin, 2001, A new alkaloid from the purple Indian Ocean tunicate Eudistoma bituminis, Tetrahedron Lett, 42, 2669, 10.1016/S0040-4039(01)00257-X Rudi, 1988, Eilatin, a novel alkaloid from the marine tunicate Eudistoma sp., Tetrahedron Lett, 29, 6655, 10.1016/S0040-4039(00)82422-3 He, 1991, Eudistones A and B: two novel octacyclic alkaloids from a Seychelles tunicate, Eudistoma sp., J Org Chem, 56, 5369, 10.1021/jo00018a031 Molinski, 1989, Varamines A and B, new cytotoxic thioalkaloids from Lissoclinurn vareau, J Org Chem, 54, 4256, 10.1021/jo00278a058 Bry, 2011, New pyridoacridine alkaloids from the purple morph of the ascidian Cystodytes dellechiajei, Tetrahedron Lett, 52, 3041, 10.1016/j.tetlet.2011.04.005 Luedtke, 2002, Eilatin Ru(II) complexes display anti-HIV activity and enantiomeric diversity in the binding of RNA, ChemBioChem, 3, 766, 10.1002/1439-7633(20020802)3:8<766::AID-CBIC766>3.0.CO;2-X Kobayashi, 1991, Cystodytins D-I, new cytotoxic tetracyclic aromatic alkaloids from the Okinawan marine tunicate Cystodytes dellechiajei, J Nat Prod, 54, 1634, 10.1021/np50078a022 Schmitz, 1991, Cytotoxic aromatic alkaloids from the ascidian Amphicarpa meridiana and Leptoclinides sp.: Meridine and 11-hydroxyascididemin, J Org Chem, 56, 804, 10.1021/jo00002a055 Lindsay, 1997, Efficient and convenient pyridine ring-E formation of the cytotoxic marine alkaloid ascididemin and related analogues, Synth Commun, 27, 2587, 10.1080/00397919708004128 Bloor, 1987, A novel pentacyclic aromatic alkaloid from an ascidian, J Am Chem Soc, 109, 6134, 10.1021/ja00254a037 Barnes, 2010, Ecionines A and B, two new cytotoxic pyridoacridine alkaloids from the Australian marine sponge, Ecionemia geodides, Tetrahedron, 66, 283, 10.1016/j.tet.2009.10.109 Gellerman, 1993, Biomimetic synthesis of pyrido [2,3,4-kl]acridines, Tetrahedron Lett, 34, 1823, 10.1016/S0040-4039(00)60789-X Gunawardand, 1989, New cytotoxic acridine alkaloids from two deep water marine sponges of the family pachustrellidue, Tetrahedron Lett, 30, 4359, 10.1016/S0040-4039(00)99360-2 Gunawardana, 1992, Pyridoacridine alkaloids from deep- water marine sponges of the family Pachastrellidae: structure revision of dercitin and related compounds and correlation with the kuanoniamines, J Org Chem, 57, 1523, 10.1021/jo00031a035 Kobayashi, 1988, Cystodytins A, B, and C, novel tetracyclic aromatic alkaloids with potent antineoplastic activity from the Okinawan tunicate Cystodytes dellechiajei, J Org Chem, 53, 1800, 10.1021/jo00243a038 Ibrahim, 2013, Sagitol C, a new cytotoxic pyridoacridine alkaloid from the sponge Oceanapia sp., Bull Fac Pharm Cairo Univ, 51, 229, 10.1016/j.bfopcu.2013.05.004 Feng, 2010, Antitrypanosomal pyridoacridine alkaloids from the Australian ascidian Polysyncraton echinatum, Tetrahedron Lett, 51, 2477, 10.1016/j.tetlet.2010.02.161 Eder, 1998, Bioactive pyridoacridine alkaloids from the Micronesian sponge Oceanapia sp., J Nat Prod, 61, 301, 10.1021/np9702704 Bontemps, 2010, Structures and antimicrobial activities of pyridoacridine alkaloids isolated from different chromotypes of the ascidian Cystodytes dellechiajei, J Nat Prod, 73, 1044, 10.1021/np900751k Bishop, 1992, Total synthesis of kuanoniamines and dercitins, J Am Chem Soc, 114, 10081, 10.1021/ja00051a062 Aoki, 2003, Pyridoacridine alkaloids inducing neuronal differentiation in a neuroblastoma cell line, from marine sponge Biemna fortis, Bioorg Med Chem, 11, 1969, 10.1016/S0968-0896(03)00086-5 Gunawardana, 1988, Dercitin, a new biologically active acridine alkaloid from a deep water marine sponge, Dercitus sp., J Am Chem Soc, 110, 4856, 10.1021/ja00222a071 Carroll, 1990, Kuanoniamines A, B, C, and D: pentacyclic alkaloids from a tunicate and its prosobranch mollusk predator Chelynotus semperi, J Org Chem, 55, 4426, 10.1021/jo00301a040 Charyulu, 1989, Diplamine, a cytotoxic polyaromatic alkaloid from the tunicate Diplosoma sp., Tetrahedron Lett, 30, 4201, 10.1016/S0040-4039(01)80689-4 Delfourne, 2003, Marine pyridoacridine alkaloids and synthetic analogues as antitumour agents, Med Res Rev, 23, 234, 10.1002/med.10032 Rinehart, 1985, 119 Ausloos, 1999, The critical evaluation of a comprehensive mass spectral library, J Am Soc Mass Spectr, 10, 287, 10.1016/S1044-0305(98)00159-7 Ford, 1994, Synthesis and structural properties of the benzopentathiepins varacin and isolissoclinotoxin A, J Org Chem, 59, 5955, 10.1021/jo00099a026 Kim, 1993, Pantherinine, a cytotoxic aromatic alkaloid, and 7-deazainosine from the ascidian Aplidium pantherinum, J Nat Prod, 56, 1813, 10.1021/np50100a023 McDonald, 1994, Inhibition of topoisomerase II catalytic activity by pyridoacridine alkaloids from a Cystodytes sp. ascidian: a mechanism for the apparent intercalator-induced inhibition of topoisomerase II, J Med Chem, 37, 3819, 10.1021/jm00048a017 Appleton, 2002, Isodiplamine, cystodytin K, and lissoclinidine: novel bioactive alkaloids from the New Zealand ascidian Lissoclinum notti, Tetrahedron, 58, 9779, 10.1016/S0040-4020(02)01296-6 Copp, 1998, Styelsamines A–D: new tetracyclic pyridoacridine alkaloids from the Indonesian ascidian Eusynstyela latericius, J Org Chem, 63, 8024, 10.1021/jo980905j Clement, 2008, Discovery of new pyridoacridine alkaloids from Lissoclinum cf. badium that inhibit the ubiquitin ligase activity of Hdm2 and stabilize p53, Bioorg Med Chem, 16, 10022, 10.1016/j.bmc.2008.10.024 Rudi, 1988, Alkaloid metabolites of the tunicate Eudistoma sp.: Segoline A, isosegoline A and nor-segoline, Tetrahedron Lett, 29, 3861, 10.1016/S0040-4039(00)82134-6 Rudi, 1989, Six new alkaloids from the purple Red Sea tunicate Eudistoma sp., J Org Chem, 54, 5331, 10.1021/jo00283a029 Koren-Goldshlager, 1998, Three new alkaloids from the marine tunicate Cystodytes violatinctus, J Org Chem, 63, 4601, 10.1021/jo9721453 Bontemps, 2013, Additional cytotoxic pyridoacridine alkaloids from the ascidian Cystodytes violatinctus and biogenetic considerations, J Nat Prod, 76, 1801, 10.1021/np400284z Nilar, 2002, Three new pyridoacridine type alkaloids from a Singaporean ascidian, J Nat Prod, 65, 1198, 10.1021/np010629v Nukoolkarn, 2008, Petrosamine, a potent anticholinesterase pyridoacridine alkaloid from a Thai marine sponge Petrosia n. sp., Bioorg Med Chem, 16, 6560, 10.1016/j.bmc.2008.05.027 Wei, 2010, Evaluation of pyridoacridine alkaloids in a Zebrafish phenotypic assay, Mar Drugs, 8, 1769, 10.3390/md8061769 Carroll, 1989, A second shermilamine alkaloid from a tunicate Trididemnum sp., J Org Chem, 54, 4231, 10.1021/jo00278a048 Kashman Y, Koren-Goldshlager G, Aknin M, Gravalos DG. Cytotoxic pyridoacridine alkaloids. United State Patent, US6350743B1; 2002. Torres, 2002, Sebastianines A and B, novel biologically active pyridoacridine alkaloids from the Brazilian ascidian Cystodytes dellechiajei, J Org Chem, 67, 5429, 10.1021/jo011174h Bontemps, 1994, Cystodamine, a new cytotoxic fused polyaromatic alkaloid from the Mediterranean ascidian Cystodytes dellechiajei, Tetrahedron Lett, 35, 7023, 10.1016/0040-4039(94)88215-0 Estermeier M. Isolierung, strukturaufklärung und synthese von pyrido[2,3,4-kl]acridin-alkaloiden aus der seeanemone Calliactis parasitica (Actiniaria). Dissertation zur erlangung des doktorgrades der Fakultät für Chemie und Pharmazie der Ludwig-Maximilians-Universität München; 2004. Zeng, 1993, Two new polycyclic aromatic alkaloids from the Okinawan marine sponge Biemna sp., Tetrahedron, 49, 8337, 10.1016/S0040-4020(01)81917-7 Tran, 2014, Structure determination of pentacyclic pyridoacridine alkaloids from the Australian marine organisms Ancorina geodides and Cnemidocarpa stolonifera, Eur J Org Chem, 2014, 4805, 10.1002/ejoc.201402372 Plubrukarn, 1998, Arnoamines A and B, new cytotoxic pentacyclic pyridoacridine alkaloids from the ascidian Cystodytes sp., J Org Chem, 63, 1657, 10.1021/jo9719721 Schmitz, 1983, Amphimedine, new aromatic alkaloid from a Pacific sponge, Amphimedon sp. carbon connectivity determination from natural abundance 13C–13C coupling constants, J Am Chem Soc, 105, 4835, 10.1021/ja00352a052 de Guzman, 1999, Neoamphimedine: a new pyridoacridine topoisomerase II inhibitor which catenates DNA, J Org Chem, 64, 1400, 10.1021/jo982047x Tasdemir, 2001, Deoxyamphimedine, a new pyridoacridine alkaloid from two tropical Xestospongia sponges, J Org Chem, 66, 3246, 10.1021/jo010153k Agrawal, 2007, Nordehydrocyclodercitin, a hexacyclic pyridoacridine alkaloid from the marine ascidian, Aplidium sp., Nat Prod Res, 21, 782, 10.1080/14786410601132212 Koren-Goldshlager, 2000, A new pyridoacridine from the marine tunicate Cystodytes violatinctus, J Nat Prod, 63, 830, 10.1021/np990569h