Marine indole alkaloids

Marine Drugs

Volumn 13, Issue 8, 2015, Pages 4814-4914

  Netz, Natalie ^a   Opatz, Till ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

Alkaloids; Bisindoles; Carbolines; Diketopiperazines; Indoles; Marine natural products; Nitrogen heterocycles; Prenylated indoles

Indexed keywords

5,6 DIBROMO LEVO HYPAPHORINE; 6 HYDROXYDISCODERMINDOLE; 8,9 DIHYDROBARETTIN; AQABAMYCIN A; AQABAMYCIN G; BACILLAMIDE A; BACILLAMIDE C; BROMOBENZISOXAZOLONE BARETTIN; CYTOGLOBOSIN A; CYTOGLOBOSIN G; GRANULATAMIDE A; GRANULATAMIDE B; INDOLE ALKALOID; KORORAMIDE A; LEPTOCLINIDAMINES A; LEPTOCLINIDAMINES C; MANSOURAMYCIN D; MERIDIANIN F; MERIDIANIN G; MONOINDOLE DERIVATIVE; N 3' ETHYLAPLYSINOPSIN; OXAZININ; PHIDIANIDINE A; PHIDIANIDINE B; PLAKOHYPAPHORINE; PLAKOHYPAPHORINE A; PYRINODEMIN F; TRACHYCLADINDOLE A; TRACHYCLADINDOLE G; UNCLASSIFIED DRUG; UNINDEXED DRUG; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; BIOLOGICAL FACTOR;

ANTIBACTERIAL ACTIVITY; ANTIMALARIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; BACTERIAL CELL; CANCER CELL; CONCENTRATION RESPONSE; DRUG CYTOTOXICITY; DRUG EFFICACY; DRUG ISOLATION; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; GROWTH INHIBITION; HUMAN; MOLLUSC; NEUROPROTECTION; NONHUMAN; AQUATIC SPECIES; METABOLISM;

ANTI-INFECTIVE AGENTS; ANTINEOPLASTIC AGENTS; AQUATIC ORGANISMS; BIOLOGICAL FACTORS; HUMANS; INDOLE ALKALOIDS;

EID: 84940434438     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md13084814     Document Type: Article

References (338)

1. Aygun, A.; Pindur, U. Chemistry and Biology of New Marine Alkaloids from the Indole and Annelated Indole Series. Curr. Med. Chem. 2003, 10, 1113-1127.
2. Pelletier, S.W. The nature and definition of an alkaloid. In Alkaloids: Chemical and Biological Perspectives; John Wiley & Sons: New York, NY, USA, 1983.
3. Lin, Z.; Zhu, T.; Fang, Y.; Gu, Q. 1H and 13C NMR assignments of two new indolic enamide diastereomers from a mangrove endophytic fungus Aspergillus sp. Magn. Reson. Chem. 2008, 46, 1212-1216.
4. Izumikawa, M.; Hashimoto, J.; Takagi, M.; Shin-ya, K. Isolation of two new terpeptin analogs-JBIR-81 and JBIR-82-from a seaweed-derived fungus, Aspergillus sp. SpD081030G1f1. J. Antibiot. 2010, 63, 389-391.
5. Sonnenschein, R.N.; Farias, J.J.; Tenney, K.; Mooberry, S.L.; Lobkovsky, E.; Clardy, J.; Crews, P. A Further Study of the Cytotoxic Constituents of a Milnamide-Producing Sponge. Org. Lett. 2004, 6, 779-782.
6. Chevallier, C.; Richardson, A.D.; Edler, M.C.; Hamel, E.; Harper, M.K.; Ireland, C.M. A New Cytotoxic and Tubulin-Interactive Milnamide Derivative from a Marine Sponge Cymbastela sp. Org. Lett. 2003, 5, 3737-3739.
7. Fernández, R.; Martín, M.J.; Rodríguez-Acebes, R.; Reyes, F.; Francesch, A.; Cuevas, C. Diazonamides C-E, new cytotoxic metabolites from the ascidian Diazona sp. Tetrahedron Lett. 2008, 49, 2283-2285.
8. Cho, J.Y.; Williams, P.G.; Kwon, H.C.; Jensen, P.R.; Fenical, W. Lucentamycins A-D, Cytotoxic Peptides from the Marine-Derived Actinomycete Nocardiopsis lucentensis. J. Nat. Prod. 2007, 70, 1321-1328.
9. Sorres, J.; Martin, M.-T.; Petek, S.; Levaique, H.; Cresteil, T.; Ramos, S.; Thoison, O.; Debitus, C.; Al-Mourabit, A. Pipestelides A-C: Cyclodepsipeptides from the Pacific Marine Sponge Pipestela candelabra. J. Nat. Prod. 2012, 75, 759-763.
10. Dmitrenok, A.; Iwashita, T.; Nakajima, T.; Sakamoto, B.; Namikoshi, M.; Nagai, H. New cyclic depsipeptides from the green alga Bryopsis species; application of a carboxypeptidase hydrolysis reaction to the structure determination. Tetrahedron 2006, 62, 1301-1308.
11. Ashour, M.; Edrada, R.; Ebel, R.; Wray, V.; Wätjen, W.; Padmakumar, K.; Müller, W.E.G.; Lin, W.H.; Proksch, P. Kahalalide Derivatives from the Indian Sacoglossan Mollusk Elysia grandifolia. J. Nat. Prod. 2006, 69, 1547-1553.
12. Rao, K.V.; Na, M.; Cook, J.C.; Peng, J.; Matsumoto, R.; Hamann, M.T. Kahalalides V-Y Isolated from a Hawaiian Collection of the Sacoglossan Mollusk Elysia rufescens. J. Nat. Prod. 2008, 71, 772-778.
13. Gala, F.; D'Auria, M.V.; De Marino, S.; Sepe, V.; Zollo, F.; Smith, C.D.; Copper, J.E.; Zampella, A. Jaspamides H-L, new actin-targeting depsipeptides from the sponge Jaspis splendans. Tetrahedron 2008, 64, 7127-7130.
14. Robinson, S.J.; Morinaka, B.I.; Amagata, T.; Tenney, K.; Bray, W.M.; Gassner, N.C.; Lokey, R.S.; Crews, P. New Structures and Bioactivity Properties of Jasplakinolide (Jaspamide) Analogues from Marine Sponges. J. Med. Chem. 2010, 53, 1651-1661.
15. Li, H.; Zhang, Q.; Li, S.; Zhu, Y.; Zhang, G.; Zhang, H.; Tian, X.; Zhang, S.; Ju, J.; Zhang, C. Identification and Characterization of Xiamycin A and Oxiamycin Gene Cluster Reveals an Oxidative Cyclization Strategy Tailoring Indolosesquiterpene Biosynthesis. J. Am. Chem. Soc. 2012, 134, 8996-9005.
16. Zhang, Q.; Li, H.; Li, S.; Zhu, Y.; Zhang, G.; Zhang, H.; Zhang, W.; Shi, R.; Zhang, C. Carboxyl Formation from Methyl via Triple Hydroxylations by XiaM in Xiamycin A Biosynthesis. Org. Lett. 2012, 14, 6142-6145.
17. Xu, Z.; Baunach, M.; Ding, L.; Hertweck, C. Bacterial Synthesis of Diverse Indole Terpene Alkaloids by an Unparalleled Cyclization Sequence. Angew. Chem. Int. Ed. Engl. 2012, 51, 10293-10297.
18. Awakawa, T.; Zhang, L.; Wakimoto, T.; Hoshino, S.; Mori, T.; Ito, T.; Ishikawa, J.; Tanner, M.E.; Abe, I. A Methyltransferase Initiates Terpene Cyclization in Teleocidin B Biosynthesis. J. Am. Chem. Soc. 2014, 136, 9910-9913.
19. Ames, B.D.; Liu, X.; Walsh, C.T. Enzymatic Processing of Fumiquinazoline F: A Tandem Oxidative-Acylation Strategy for the Generation of Multicyclic Scaffolds in Fungal Indole Alkaloid Biosynthesis. Biochemistry 2010, 49, 8564-8576.
20. Kato, H.; Nakahara, T.; Yamaguchi, M.; Kagiyama, I.; Finefield, J.M.; Sunderhaus, J.D.; Sherman, D.H.; Williams, R.M.; Tsukamoto, S. Bioconversion of 6-epi-Notoamide T produces metabolites of unprecedented structures in a marine-derived Aspergillus sp. Tetrahedron Lett. 2015, 56, 247-251.
21. Kato, H.; Nakamura, Y.; Finefield, J.M.; Umaoka, H.; Nakahara, T.; Williams, R.M.; Tsukamoto, S. Study on the biosynthesis of the notoamides: Pinacol-type rearrangement of the isoprenyl unit in deoxybrevianamide E and 6-hydroxydeoxybrevianamide E. Tetrahedron Lett. 2011, 52, 6923-6926.
22. De Sá Alves, F.R.; Barreiro, E.J.; Fraga, C.A.M. From nature to drug discovery: The indole scaffold as a "privileged structure". Mini Rev. Med. Chem. 2009, 9, 782-793.
23. Xu, W.; Gavia, D.J.; Tang, Y. Biosynthesis of fungal indole alkaloids. Nat. Prod. Rep. 2014, 31, 1474-1487.
24. Güven, K.C.; Percot, A.; Sezik, E. Alkaloids in Marine Algae. Mar. Drugs 2010, 8, 269-284.
25. Pauletti, P.M.; Cintra, L.S.; Braguine, C.G.; Da Silva Filho, A.A.; Andrade e Silva, M.L.; Cunha, W.R.; Januário, A.H. Halogenated Indole Alkaloids from Marine Invertebrates. Mar. Drugs 2010, 8, 1526-1549.
26. Radwanski, E.R.; Last, R.L. Tryptophan biosynthesis and metabolism: Biochemical and molecular genetics. Plant Cell 1995, 7, 921-934.
27. Hu, J.-F.; Schetz, J.A.; Kelly, M.; Peng, J.-N.; Ang, K.K.H.; Flotow, H.; Leong, C.Y.; Ng, S.B.; Buss, A.D.; Wilkins, S.P.; et al. New Antiinfective and Human 5-HT2 Receptor Binding Natural and Semisynthetic Compounds from the Jamaican Sponge Smenospongia aurea. J. Nat. Prod. 2002, 65, 476-480.
28. Segraves, N.L.; Crews, P. Investigation of Brominated Tryptophan Alkaloids from Two Thorectidae Sponges: Thorectandra and Smenospongia. J. Nat. Prod. 2005, 68, 1484-1488.
29. Fahey, S.J.; Carroll, A.R. Natural products isolated from species of Halgerda Bergh, 1880 (Mollusca: Nudibranchia) and their ecological and evolutionary implications. J. Chem. Ecol. 2007, 33, 1226-1234.
30. Longeon, A.; Copp, B.R.; Quévrain, E.; Roué, M.; Kientz, B.; Cresteil, T.; Petek, S.; Debitus, C.; Bourguet-Kondracki, M.-L. Bioactive Indole Derivatives from the South Pacific Marine Sponges Rhopaloeides odorabile and Hyrtios sp. Mar. Drugs 2011, 9, 879-888.
31. Shen, S.; Liu, D.; Wei, C.; Proksch, P.; Lin, W. Purpuroines A-J, halogenated alkaloids from the sponge Iotrochota purpurea with antibiotic activity and regulation of tyrosine kinases. Bioorg. Med. Chem. 2012, 20, 6924-6928.
32. Campagnuolo, C.; Fattorusso, E.; Taglialatela-Scafati, O. Plakohypaphorines A-C, Iodine-Containing Alkaloids from the Caribbean Sponge Plakortis simplex. Eur. J. Org. Chem. 2003, 2003, 284-287.
33. Borrelli, F.; Campagnuolo, C.; Capasso, R.; Fattorusso, E.; Taglialatela-Scafati, O. Iodinated Indole Alkaloids From Plakortis simplex-New Plakohypaphorines and an Evaluation of Their Antihistamine Activity. Eur. J. Org. Chem. 2004, 2004, 3227-3232.
34. Li, Y.; Li, X.; Kim, D.; Choi, H.; Son, B. Indolyl alkaloid derivatives, Nb-acetyltryptamine and oxaline from a marine-derived fungus. Arch. Pharmacal Res. 2003, 26, 21-23.
35. Sauleau, P.; Martin, M.-T.; Dau, M.-E.T.H.; Youssef, D.T.A.; Bourguet-Kondracki, M.-L. Hyrtiazepine, an Azepino-indole-Type Alkaloid from the Red Sea Marine Sponge Hyrtios erectus. J. Nat. Prod. 2006, 69, 1676-1679.
36. Ashour, M.A.; Elkhayat, E.S.; Ebel, R.; Edrada, R.; Proksch, P. Indole alkaloid from the Red Sea sponge Hyrtios erectus. Arkivoc 2007, 15, 225-231.
37. Jeong, S.-Y.; Ishida, K.; Ito, Y.; Okada, S.; Murakami, M. Bacillamide, a novel algicide from the marine bacterium, Bacillus sp. SY-1, against the harmful dinoflagellate, Cochlodinium polykrikoides. Tetrahedron Lett. 2003, 44, 8005-8007.
38. Socha, A.M.; Long, R.A.; Rowley, D.C. Bacillamides from a Hypersaline Microbial Mat Bacterium. J. Nat. Prod. 2007, 70, 1793-1795.
39. Cohen, J.; Paul, G.; Gunasekera, S.; Longley, R.; Pomponi, S. 6-Hydroxydiscodermindole, A New Discodermindole from the Marine Sponge Discodermia polydiscus. Pharm. Biol. 2004, 42, 59-61.
40. El-Gamal, A.A.; Wang, W.-L.; Duh, C.-Y. Sulfur-Containing Polybromoindoles from the Formosan Red Alga Laurencia brongniartii. J. Nat. Prod. 2005, 68, 815-817.
41. Ji, N.-Y.; Li, X.-M.; Cui, C.-M.; Wang, B.-G. Terpenes and Polybromoindoles from the Marine Red Alga Laurencia decumbens (Rhodomelaceae). Helvetica Chimica Acta 2007, 90, 1731-1736.
42. Ji, N.-Y.; Li, X.-M.; Ding, L.-P.; Wang, B.-G. Aristolane Sesquiterpenes and Highly Brominated Indoles from the Marine Red Alga Laurencia similis (Rhodomelaceae). Helvetica Chimica Acta 2007, 90, 385-391.
43. Li, C.-S.; Li, X.-M.; Cui, C.-M.; Wang, B.-G. Brominated Metabolites from the Marine Red Alga Laurencia similis. Zeitschrift für Naturforschung B 2010, 65, 87-89.
44. Su, H.; Yuan, Z.H.; Li, J.; Guo, S.J.; Deng, L.P.; Han, L.J.; Zhu, X.B.; Shi, D.Y. Two new bromoindoles from red alga Laurencia similis. Chin. Chem. Lett. 2009, 20, 456-458.
45. Wang, R.-P.; Lin, H.-W.; Li, L.-Z.; Gao, P.-Y.; Xu, Y.; Song, S.-J. Monoindole alkaloids from a marine sponge Mycale fibrexilis. Biochem. Syst. Ecol. 2012, 43, 210-213.
46. Carroll, A.R.; Buchanan, M.S.; Edser, A.; Hyde, E.; Simpson, M.; Quinn, R.J. Dysinosins B-D, Inhibitors of Factor VIIa and Thrombin from the Australian Sponge Lamellodysidea chlorea. J. Nat. Prod. 2004, 67, 1291-1294.
47. Carroll, A.R.; Pierens, G.K.; Fechner, G.; de Almeida Leone, P.; Ngo, A.; Simpson, M.; Hyde, E.; Hooper, J.N.A.; Boström, S.-L.; Musil, D.; et al. Dysinosin A: A Novel Inhibitor of Factor VIIa and Thrombin from a New Genus and Species of Australian Sponge of the Family Dysideidae. J. Am. Chem. Soc. 2002, 124, 13340-13341.
48. Reyes, F.; Martín, R.; Fernández, R. Granulatamides A and B, Cytotoxic Tryptamine Derivatives from the Soft Coral Eunicella granulata. J. Nat. Prod. 2006, 69, 668-670.
49. Seldes, A.M.; Rodriguez Brasco, M.F.; Hernandez Franco, L.; Palermo, J.A. Identification of two meridianins from the crude extract of the tunicate Aplidium meridianum by tandem mass spectrometry. Nat. Prod. Res. 2007, 21, 555-563.
50. Reyes, F.; Fernández, R.; Rodríguez, A.; Francesch, A.; Taboada, S.; Ávila, C.; Cuevas, C. Aplicyanins A-F, new cytotoxic bromoindole derivatives from the marine tunicate Aplidium cyaneum. Tetrahedron 2008, 64, 5119-5123.
51. Šíša, M.; Pla, D.; Altuna, M.; Francesch, A.; Cuevas, C.; Albericio, F.; Álvarez, M. Total Synthesis and Antiproliferative Activity Screening of (±)-Aplicyanins A, B and E and Related Analogues. J. Med. Chem. 2009, 52, 6217-6223.
52. Ciminiello, P.; Dell'Aversano, C.; Fattorusso, E.; Forino, M.; Magno, S.; Ianaro, A.; Di Rosa, M. Oxazinin-1, -2 and -3-A Novel Toxic Compound and Its Analogues from the Digestive Glands of Mytilus galloprovincialis. Eur. J. Org. Chem. 2001, 2001, 49-53.
53. Ciminiello, P.; Dell'Aversano, C.; Fattorusso, C.; Fattorusso, E.; Forino, M.; Magno, S. Assignment of the absolute stereochemistry of oxazinin-1: Application of the 9-AMA shift-correlation method for β-chiral primary alcohols. Tetrahedron 2001, 57, 8189-8192.
54. Ciminiello, P.; Dell'Aversano, C.; Fattorusso, E.; Forino, M.; Magno, S.; Santelia, F.U.; Moutsos, V.I.; Pitsinos, E.N.; Couladouros, E.A. Oxazinins from toxic mussels: Isolation of a novel oxazinin and reassignment of the C-2 configuration of oxazinin-1 and -2 on the basis of synthetic models. Tetrahedron 2006, 62, 7738-7743.
55. Ciminiello, P.; Dell'Aversano, C.; Fattorusso, E.; Forino, M.; Grauso, L.; Santelia, F.U.; Tartaglione, L.; Moutsos, V.I.; Pitsinos, E.N.; Couladouros, E.A. Stereostructural Determination by a Synthetic and NMR-Based Approach of Three Oxazinins Isolated from Adriatic Mussels. Eur. J. Org. Chem. 2007, 2007, 5434-5439.
56. Bao, B.; Zhang, P.; Lee, Y.; Hong, J.; Lee, C.-O.; Jung, J. Monoindole Alkaloids from a Marine Sponge Spongosorites sp. Mar. Drugs 2007, 5, 31-39.
57. Santalova, E.A.; Denisenko, V.A.; Berdyshev, D.V.; Aminin, D.L.; Sanamyan, K.E. 6-Bromo-5- hydroxyindolyl-3-glyoxylate from the Far Eastern Ascidian Syncarpa oviformis. Nat. Prod. Commun. 2008, 3, 1617-1620.
58. Abdjul, D.; Yamazaki, H.; Ukai, K.; Namikoshi, M. Two new indole derivatives from a marine sponge Ircinia sp. collected at Iriomote Island. J. Nat. Med. 2015, 69, 416-420.
59. Řezanka, T.; Hanuš, L.O.; Dembitsky, V.M.; Sigler, K. Identification of the Eight-Membered Heterocycles Hicksoanes A-C from the Gorgonian Subergorgia hicksoni. Eur. J. Org. Chem. 2008, 2008, 1265-1270.
60. Sjögren, M.; Göransson, U.; Johnson, A.-L.; Dahlström, M.; Andersson, R.; Bergman, J.; Jonsson, P.R.; Bohlin, L. Antifouling Activity of Brominated Cyclopeptides from the Marine Sponge Geodia barretti. J. Nat. Prod. 2004, 67, 368-372.
61. Hedner, E.; Sjögren, M.; Hodzic, S.; Andersson, R.; Göransson, U.; Jonsson, P.R.; Bohlin, L. Antifouling Activity of a Dibrominated Cyclopeptide from the Marine Sponge Geodia barretti. J. Nat. Prod. 2008, 71, 330-333.
62. Hawas, U.W.; Shaaban, M.; Shaaban, K.A.; Speitling, M.; Maier, A.; Kelter, G.; Fiebig, H.H.; Meiners, M.; Helmke, E.; Laatsch, H. Mansouramycins A-D, Cytotoxic Isoquinolinequinones from a Marine Streptomycete. J. Nat. Prod. 2009, 72, 2120-2124.
63. Sugiyama, Y.; Ito, Y.; Suzuki, M.; Hirota, A. Indole Derivatives from a Marine Sponge-Derived Yeast as DPPH Radical Scavengers. J. Nat. Prod. 2009, 72, 2069-2071.
64. Qi, S.-H.; Wang, Y.-F.; Zhang, S. Steroids and alkaloids from the South China Sea sponge Axinella sp. J. Asian. Nat. Prod. Res. 2009, 11, 1040-1044.
65. Capon, R.J.; Peng, C.; Dooms, C. Trachycladindoles A-G: Cytotoxic heterocycles from an Australian marine sponge, Trachycladus laevispirulifer. Org. Biomol. Chem. 2008, 6, 2765-2771.
66. Al-Zereini, W.; Fotso Fondja Yao, C.B.; Laatsch, H.; Anke, H. Aqabamycins A-G: Novel nitro maleimides from a marine Vibrio species. I. Taxonomy, fermentation, isolation and biological activities. J. Antibiot. 2010, 63, 297-301.
67. Fotso Fondja Yao, C.B.; Zereini, W.A.; Fotso, S.; Anke, H.; Laatsch, H. Aqabamycins A-G: Novel nitro maleimides from a marine Vibrio species: II. Structure elucidation. J. Antibiot. 2010, 63, 303-308.
68. Carbone, M.; Li, Y.; Irace, C.; Mollo, E.; Castelluccio, F.; Di Pascale, A.; Cimino, G.; Santamaria, R.; Guo, Y.-W.; Gavagnin, M. Structure and Cytotoxicity of Phidianidines A and B: First Finding of 1, 2, 4-Oxadiazole System in a Marine Natural Product. Org. Lett. 2011, 13, 2516-2519.
69. Vitale, R.M.; Gatti, M.; Carbone, M.; Barbieri, F.; Felicità, V.; Gavagnin, M.; Florio, T.; Amodeo, P. Minimalist Hybrid Ligand/Receptor-Based Pharmacophore Model for CXCR4 Applied to a Small-Library of Marine Natural Products Led to the Identification of Phidianidine A as a New CXCR4 Ligand Exhibiting Antagonist Activity. ACS Chem. Biol. 2013, 8, 2762-2770.
70. Brogan, J.T.; Stoops, S.L.; Lindsley, C.W. Total synthesis and biological evaluation of phidianidines A and B uncovers unique pharmacological profiles at CNS targets. ACS Chem. Neurosci. 2012, 3, 658-664.
71. Jiang, C.-S.; Fu, Y.; Zhang, L.; Gong, J.-X.; Wang, Z.-Z.; Xiao, W.; Zhang, H.-Y.; Guo, Y.-W. Synthesis and biological evaluation of novel marine-derived indole-based 1, 2, 4-oxadiazoles derivatives as multifunctional neuroprotective agents. Bioorg. Med. Chem. Lett. 2015, 25, 216-220.
72. Carroll, A.R.; Wild, S.J.; Duffy, S.; Avery, V.M. Kororamide A, a new tribrominated indole alkaloid from the Australian bryozoan Amathia tortuosa. Tetrahedron Lett. 2012, 53, 2873-2875.
73. Gang, C.; Shen, M.-X.; Xin, W.; Fan, X.-M.; Ma, H.-M.; Wu, H.-H.; Pei, Y.-H. Indole alkaloids from the marine bacterium Pantoea agglomerans. Chem. Nat. Compd. 2013, 49, 291-293.
74. Carroll, A.R.; Avery, V.M. Leptoclinidamines A-C, Indole Alkaloids from the Australian Ascidian Leptoclinides durus. J. Nat. Prod. 2009, 72, 696-699.
75. Yamazaki, H.; Wewengkang, D.S.; Nishikawa, T.; Rotinsulu, H.; Mangindaan, R.E.P.; Namikoshi, M. Two New Tryptamine Derivatives, Leptoclinidamide and (-)-Leptoclinidamine B, from an Indonesian Ascidian Leptoclinides dubius. Mar. Drugs 2012, 10, 349.
76. Zaharenko, A.J.; Picolo, G.; Ferreira, W.A.; Murakami, T.; Kazuma, K.; Hashimoto, M.; Cury, Y.; de Freitas, J.C.; Satake, M.; Konno, K. Bunodosine 391: An Analgesic Acylamino Acid from the Venom of the Sea Anemone Bunodosoma cangicum. J. Nat. Prod. 2011, 74, 378-382.
77. Kura, K.I.; Kubota, T.; Fromont, J.; Kobayashi, J.I. Pyrinodemins E and F, new 3-alkylpyridine alkaloids from sponge Amphimedon sp. Bioorg. Med. Chem. Lett. 2011, 21, 267-270.
78. Cui, C.-M.; Li, X.-M.; Li, C.-S.; Proksch, P.; Wang, B.-G. Cytoglobosins A-G, Cytochalasans from a Marine-Derived Endophytic Fungus, Chaetomium globosum QEN-14. J. Nat. Prod. 2010, 73, 729-733.
79. Takahashi, Y.; Kubota, T.; Shibazaki, A.; Gonoi, T.; Fromont, J.; Kobayashi, J.I. Nakijinamines C-E, New Heteroaromatic Alkaloids from the Sponge Suberites Species. Org. Lett. 2011, 13, 3016-3019.
80. Takahashi, Y.; Tanaka, N.; Kubota, T.; Ishiyama, H.; Shibazaki, A.; Gonoi, T.; Fromont, J.; Kobayashi, J.I. Heteroaromatic alkaloids, nakijinamines, from a sponge Suberites sp. Tetrahedron 2012, 68, 8545-8550.
81. Prawat, H.; Mahidol, C.; Kaweetripob, W.; Wittayalai, S.; Ruchirawat, S. Iodo-sesquiterpene hydroquinone and brominated indole alkaloids from the Thai sponge Smenospongia sp. Tetrahedron 2012, 68, 6881-6886.
82. He, F.; Han, Z.; Peng, J.; Qian, P.-Y.; Qi, S.-H. Antifouling indole alkaloids from two marine derived fungi. Nat. Prod. Commun. 2013, 8, 329-332.
83. Peng, J.; Lin, T.; Wang, W.; Xin, Z.; Zhu, T.; Gu, Q.; Li, D. Antiviral Alkaloids Produced by the Mangrove-Derived Fungus Cladosporium sp. PJX-41. J. Nat. Prod. 2013, 76, 1133-1140.
84. Li, J.L.; Han, S.C.; Yoo, E.S.; Shin, S.; Hong, J.; Cui, Z.; Li, H.; Jung, J.H. Anti-inflammatory Amino Acid Derivatives from the Ascidian Herdmania momus. J. Nat. Prod. 2011, 74, 1792-1797.
85. Li, J.L.; Xiao, B.; Park, M.; Yoo, E.S.; Shin, S.; Hong, J.; Chung, H.Y.; Kim, H.S.; Jung, J.H. PPAR-γ Agonistic Metabolites from the Ascidian Herdmania momus. J. Nat. Prod. 2012, 75, 2082-2087.
86. Li, J.L.; Kim, E.L.; Wang, H.; Hong, J.; Shin, S.; Lee, C.-K.; Jung, J.H. Epimeric methylsulfinyladenosine derivatives from the marine ascidian Herdmania momus. Bioorg. Med. Chem. Lett. 2013, 23, 4701-4704.
87. Finlayson, R.; Pearce, A.N.; Page, M.J.; Kaiser, M.; Bourguet-Kondracki, M.-L.; Harper, J.L.; Webb, V.L.; Copp, B.R. Didemnidines A and B, Indole Spermidine Alkaloids from the New Zealand Ascidian Didemnum sp. J. Nat. Prod. 2011, 74, 888-892.
88. Chen, L.; Tang, X.-X.; Zheng, M.; Yi, Z.-W.; Xiao, X.; Qiu, Y.-K.; Wu, Z. A novel indole alkaloid from deep-sea sediment metagenomic clone-derived Escherichia coli fermentation broth. J. Asian. Nat. Prod. Res. 2011, 13, 444-448.
89. Wang, Y.; Tang, X.; Shao, Z.; Ren, J.; Liu, D.; Proksch, P.; Lin, W. Indole-based alkaloids from deep-sea bacterium Shewanella piezotolerans with antitumor activities. J. Antibiot. 2014, 67, 395-399.
90. Murcia, C.; Coello, L.; Fernández, R.; Martín, M.; Reyes, F.; Francesch, A.; Munt, S.; Cuevas, C. Tanjungides A and B: New Antitumoral Bromoindole Derived Compounds from Diazona cf. formosa. Isolation and Total Synthesis. Mar. Drugs 2014, 12, 1116-1130.
91. Kornsakulkarn, J.; Saepua, S.; Boonruangprapa, T.; Suphothina, S.; Thongpanchang, C. New β-carboline and indole alkaloids from Actinomycete Actinomadura sp. BCC 24717. Phytochem. Lett. 2013, 6, 491-494.
92. Huang, X.-L.; Gao, Y.; Xue, D.-Q.; Liu, H.-L.; Peng, C.-S.; Zhang, F.-L.; Li, Z.-Y.; Guo, Y.-W. Streptomycindole, an Indole Alkaloid from a Marine Streptomyces sp. DA22 Associated with South China Sea Sponge Craniella australiensis. Helvetica Chimica Acta 2011, 94, 1838-1842.
93. Guella, G.; N'Diaye, I.; Fofana, M.; Mancini, I. Isolation, synthesis and photochemical properties of almazolone, a new indole alkaloid from a red alga of Senegal. Tetrahedron 2006, 62, 1165-1170.
94. Feng, Y.; Davis, R.A.; Sykes, M.L.; Avery, V.M.; Quinn, R.J. Iotrochamides A and B, antitrypanosomal compounds from the Australian marine sponge Iotrochota sp. Bioorg. Med. Chem. Lett. 2012, 22, 4873-4876.
95. Yang, X.-W.; Zhang, G.-Y.; Ying, J.-X.; Yang, B.; Zhou, X.-F.; Steinmetz, A.; Liu, Y.-H.; Wang, N. Isolation, Characterization, and Bioactivity Evaluation of 3-((6-Methylpyrazin-2- yl)methyl)-1H-indole, a New Alkaloid from a Deep-Sea-Derived Actinomycete Serinicoccus profundi sp. nov. Mar. Drugs 2012, 11, 33-39.
96. Hanssen, K.Ø.; Schuler, B.; Williams, A.J.; Demissie, T.B.; Hansen, E.; Andersen, J.H.; Svenson, J.; Blinov, K.; Repisky, M.; Mohn, F.; et al. A Combined Atomic Force Microscopy and Computational Approach for the Structural Elucidation of Breitfussin A and B: Highly Modified Halogenated Dipeptides from Thuiaria breitfussi. Angew. Chem. Int. Ed. Engl. 2012, 51, 12238-12241.
97. Lee, Y.-J.; Lee, D.-G.; Rho, H.S.; Krasokhin, V.B.; Shin, H.J.; Lee, J.S.; Lee, H.-S. Cytotoxic 5-Hydroxyindole Alkaloids from the Marine Sponge Scalarispongia sp. J. Heterocycl. Chem. 2013, 50, 1400-1404.
98. He, W.-F.; Xue, D.-Q.; Yao, L.-G.; Li, J.-Y.; Li, J.; Guo, Y.-W. Hainanerectamines A-C, Alkaloids from the Hainan Sponge Hyrtios erecta. Mar. Drugs 2014, 12, 3982-3993.
99. Higuchi, K.; Kawasaki, T. Simple indole alkaloids and those with a nonrearranged monoterpenoid unit. Nat. Prod. Rep. 2007, 24, 843-868.
100. Li, S.-M. Prenylated indole derivatives from fungi: Structure diversity, biological activities, biosynthesis and chemoenzymatic synthesis. Nat. Prod. Rep. 2010, 27, 57-78.
101. Byun, H.-G.; Zhang, H.; Mochizuki, M.; Adachi, K.; Shizuri, Y.; Lee, W.-J.; Kim, S.-K. Novel antifungal diketopiperazine from marine fungus. J. Antibiot. 2003, 56, 102-106.
102. Schultz, A.W.; Oh, D.-C.; Carney, J.R.; Williamson, R.T.; Udwary, D.W.; Jensen, P.R.; Gould, S.J.; Fenical, W.; Moore, B.S. Biosynthesis and Structures of Cyclomarins and Cyclomarazines, Prenylated Cyclic Peptides of Marine Actinobacterial Origin. J. Am. Chem. Soc. 2008, 130, 4507-4516.
103. Motohashi, K.; Irie, K.; Toda, T.; Matsuo, Y.; Kasai, H.; Sue, M.; Furihata, K.; Seto, H. Studies on Terpenoids Produced by Actinomycetes. J. Antibiot. 2008, 61, 75-80.
104. Devi, P.; Rodrigues, C.; Naik, C.G.; D'Souza, L. Isolation and Characterization of Antibacterial Compound from a Mangrove-Endophytic Fungus, Penicillium chrysogenum MTCC 5108. Indian J. Microbiol. 2012, 52, 617-623.
105. Zhang, P.; Meng, L.-H.; Mándi, A.; Kurtán, T.; Li, X.-M.; Liu, Y.; Li, X.; Li, C.-S.; Wang, B.-G. Brocaeloids A-C, 4-Oxoquinoline and Indole Alkaloids with C-2 Reversed Prenylation from the Mangrove-Derived Endophytic Fungus Penicillium brocae. Eur. J. Org. Chem. 2014, 2014, 4029-4036.
106. Li, C.-S.; Li, X.-M.; An, C.-Y.; Wang, B.-G. Prenylated Indole Alkaloid Derivatives from Marine Sediment-Derived Fungus Penicillium paneum SD-44. Helvetica Chimica Acta 2014, 97, 1440-1444.
107. Zhou, Y.; Debbab, A.; Wray, V.; Lin, W.; Schulz, B.; Trepos, R.; Pile, C.; Hellio, C.; Proksch, P.; Aly, A.H. Marine bacterial inhibitors from the sponge-derived fungus Aspergillus sp. Tetrahedron Lett. 2014, 55, 2789-2792.
108. Carle, J.S.; Christophersen, C. Bromo-substituted physostigmine alkaloids from a marine bryozoa Flustra foliacea. J. Am. Chem. Soc. 1979, 101, 4012-4013.
109. Carle, J.S.; Christophersen, C. Marine alkaloids. 2. Bromo alkaloids from a marine bryozoan Flustra foliacea. Isolation and structure elucidation. J. Org. Chem. 1980, 45, 1586-1589.
110. Carle, J.S.; Christophersen, C. Marine alkaloids. 3. Bromo-substituted alkaloids from the marine bryozoan Flustra foliacea, flustramine C and flustraminol A and B. J. Org. Chem. 1981, 46, 3440-3443.
111. Adla, S.K.; Sasse, F.; Kelter, G.; Fiebig, H.-H.; Lindel, T. Doubly prenylated tryptamines: Cytotoxicity, antimicrobial activity and cyclisation to the marine natural product flustramine A. Org. Biomol. Chem. 2013, 11, 6119-6130.
112. Sjöblom, T.; Bohlin, L.; Christophersen, C. Studies of Swedish marine organisms. II. Muscle-relaxant alkaloids from the marine bryozoan Flustra foliacea. Acta Pharm. Suec. 1983, 20, 415-418.
113. Rivera-Becerril, E.; Joseph-Nathan, P.; Pérez-Álvarez, V.M.; Morales-Ríos, M.S. Synthesis and Biological Evaluation of (-)- and (+)-Debromoflustramine B and Its Analogues as Selective Butyrylcholinesterase Inhibitors. J. Med. Chem. 2008, 51, 5271-5284.
114. Peters, L.; König, G.M.; Terlau, H.; Wright, A.D. Four New Bromotryptamine Derivatives from the Marine Bryozoan Flustra foliacea. J. Nat. Prod. 2002, 65, 1633-1637.
115. Peters, L.; Wright, A.D.; Kehraus, S.; Gündisch, D.; Tilotta, M.C.; König, G.M. Prenylated Indole Alkaloids from Flustra foliacea with Subtype Specific Binding on NAChRs. Planta. Med. 2004, 70, 883-886.
116. Bunders, C.A.; Minvielle, M.J.; Worthington, R.J.; Ortiz, M.; Cavanagh, J.; Melander, C. Intercepting Bacterial Indole Signaling with Flustramine Derivatives. J. Am. Chem. Soc. 2011, 133, 20160-20163.
117. Sala, F.; Mulet, J.; Reddy, K.P.; Bernal, J.A.; Wikman, P.; Valor, L.M.; Peters, L.; König, G.M.; Criado, M.; Sala, S. Potentiation of human α4β2 neuronal nicotinic receptors by a Flustra foliacea metabolite. Neurosci. Lett. 2005, 373, 144-149.
118. Rochfort, S.J.; Moore, S.; Craft, C.; Martin, N.H.; Van Wagoner, R.M.; Wright, J.L.C. Further Studies on the Chemistry of the Flustra Alkaloids from the Bryozoan Flustra foliacea. J. Nat. Prod. 2009, 72, 1773-1781.
119. Williams, R.M.; Cox, R.J. Paraherquamides, Brevianamides, and Asperparalines: Laboratory Synthesis and Biosynthesis. An Interim Report. Acc. Chem. Res. 2003, 36, 127-139.
120. Ding, Y.; Wet, J.R.D.; Cavalcoli, J.; Li, S.; Greshock, T.J.; Miller, K.A.; Finefield, J.M.; Sunderhaus, J.D.; McAfoos, T.J.; Tsukamoto, S.; et al. Genome-Based Characterization of Two Prenylation Steps in the Assembly of the Stephacidin and Notoamide Anticancer Agents in a Marine-Derived Aspergillus sp. J. Am. Chem. Soc. 2010, 132, 12733-12740.
121. Qian-Cutrone, J.; Huang, S.; Shu, Y.-Z.; Vyas, D.; Fairchild, C.; Menendez, A.; Krampitz, K.; Dalterio, R.; Klohr, S.E.; Gao, Q. Stephacidin A and B: Two Structurally Novel, Selective Inhibitors of the Testosterone-Dependent Prostate LNCaP Cells. J. Am. Chem. Soc. 2002, 124, 14556-14557.
122. Whyte, A.C.; Gloer, J.B.; Wicklow, D.T.; Dowd, P.F. Sclerotiamide: A New Member of the Paraherquamide Class with Potent Antiinsectan Activity from the Sclerotia of Aspergillus sclerotiorum. J. Nat. Prod. 1996, 59, 1093-1095.
123. Liesch, J.M.; Wichmann, C.F. Novel Antinematodal and Antiparasitic Agents from Penicillium charlesii. II. Structure Determination of Paraherquamides B, C, D, E, F, and G. J. Antibiot. 1990, 43, 1380-1386.
124. Blanchflower, S.E.; Banks, R.M.; Everett, J.R.; Manger, B.R.; Reading, C. New Paraherquamide Antibiotics with Anthelmintic Activity. J. Antibiot. 1991, 44, 492-497.
125. Kato, H.; Yoshida, T.; Tokue, T.; Nojiri, Y.; Hirota, H.; Ohta, T.; Williams, R.M.; Tsukamoto, S. Notoamides A-D: Prenylated Indole Alkaloids Isolated from a Marine-Derived Fungus, Aspergillus sp. Angew. Chem. Int. Ed. Engl. 2007, 46, 2254-2256; Corrigendum in 2013, 52, 7909.
126. Tsukamoto, S.; Kato, H.; Greshock, T.J.; Hirota, H.; Ohta, T.; Williams, R.M. Isolation of Notoamide E, a Key Precursor in the Biosynthesis of Prenylated Indole Alkaloids in a Marine- Derived Fungus, Aspergillus sp. J. Am. Chem. Soc. 2009, 131, 3834-3835.
127. Tsukamoto, S.; Kato, H.; Samizo, M.; Nojiri, Y.; Onuki, H.; Hirota, H.; Ohta, T. Notoamides F-K, Prenylated Indole Alkaloids Isolated from a Marine-Derived Aspergillus sp. J. Nat. Prod. 2008, 71, 2064-2067.
128. Tsukamoto, S.; Kawabata, T.; Kato, H.; Greshock, T.J.; Hirota, H.; Ohta, T.; Williams, R.M. Isolation of Antipodal (-)-Versicolamide B and Notoamides L-N from a Marine-Derived Aspergillus sp. Org. Lett. 2009, 11, 1297-1300.
129. Tsukamoto, S.; Umaoka, H.; Yoshikawa, K.; Ikeda, T.; Hirota, H. Notoamide O, a Structurally Unprecedented Prenylated Indole Alkaloid, and Notoamides P-R from a Marine-Derived Fungus, Aspergillus sp. J. Nat. Prod. 2010, 73, 1438-1440.
130. Chen, M.; Shao, C.-L.; Fu, X.-M.; Xu, R.-F.; Zheng, J.-J.; Zhao, D.-L.; She, Z.-G.; Wang, C.-Y. Bioactive Indole Alkaloids and Phenyl Ether Derivatives from a Marine-Derived Aspergillus sp. Fungus. J. Nat. Prod. 2013, 76, 547-553; Corrigendum in 2013, 76, 1229.
131. Li, S.; Finefield, J.M.; Sunderhaus, J.D.; McAfoos, T.J.; Williams, R.M.; Sherman, D.H. Biochemical Characterization of NotB as an FAD-Dependent Oxidase in the Biosynthesis of Notoamide Indole Alkaloids. J. Am. Chem. Soc. 2012, 134, 788-791.
132. Tsukamoto, S.; Umaoka, H.; Yoshikawa, K.; Ikeda, T.; Hirota, H. Correction to Notoamide O, a Structurally Unprecedented Prenylated Indole Alkaloid, and Notoamides P-R from a Marine- Derived Fungus, Aspergillus sp. J. Nat. Prod. 2013, 76, 1232-1232.
133. Finefield, J.M.; Williams, R.M. Correction to Synthesis of Notoamide J: A Potentially Pivotal Intermediate in the Biosynthesis of Several Prenylated Indole Alkaloids. J. Org. Chem. 2013, 78, 8214-8214.
134. Zhang, P.; Li, X.-M.; Wang, J.-N.; Li, X.; Wang, B.-G. Prenylated indole alkaloids from the marine-derived fungus Paecilomyces variotii. Chin. Chem. Lett. 2015, 26, 313-316.
135. Zhang, X.-Y.; Xu, X.-Y.; Peng, J.; Ma, C.-F.; Nong, X.-H.; Bao, J.; Zhang, G.-Z.; Qi, S.-H. Antifouling potentials of eight deep-sea-derived fungi from the South China Sea. J. Ind. Microbiol. Biotechnol. 2014, 41, 741-748.
136. Kato, H.; Nakahara, T.; Sugimoto, K.; Matsuo, K.; Kagiyama, I.; Frisvad, J.C.; Sherman, D.H.; Williams, R.M.; Tsukamoto, S. Isolation of Notoamide S and Enantiomeric 6-epi-Stephacidin A from the Fungus Aspergillus amoenus: Biogenetic Implications. Org. Lett. 2015, 17, 700-703.
137. Sunderhaus, J.D.; McAfoos, T.J.; Finefield, J.M.; Kato, H.; Li, S.; Tsukamoto, S.; Sherman, D.H.; Williams, R.M. Synthesis and Bioconversions of Notoamide T: A Biosynthetic Precursor to Stephacidin A and Notoamide B. Org. Lett. 2013, 15, 22-25.
138. Li, S.; Srinivasan, K.; Tran, H.; Yu, F.; Finefield, J.M.; Sunderhaus, J.D.; McAfoos, T.J.; Tsukamoto, S.; Williams, R.M.; Sherman, D.H. Comparative analysis of the biosynthetic systems for fungal bicyclo[2.2.2]diazaoctane indole alkaloids: The (+)/(-)-notoamide, paraherquamide and malbrancheamide pathways. Med. Chem. Comm. 2012, 3, 987-996.
139. Cai, S.; Luan, Y.; Kong, X.; Zhu, T.; Gu, Q.; Li, D. Isolation and Photoinduced Conversion of 6-epi-Stephacidins from Aspergillus taichungensis. Org. Lett. 2013, 15, 2168-2171.
140. Watts, K.R.; Loveridge, S.T.; Tenney, K.; Media, J.; Valeriote, F.A.; Crews, P. Utilizing DART Mass Spectrometry to Pinpoint Halogenated Metabolites from a Marine Invertebrate-Derived Fungus. J. Org. Chem. 2011, 76, 6201-6208.
141. Peng, J.; Zhang, X.-Y.; Tu, Z.-C.; Xu, X.-Y.; Qi, S.-H. Alkaloids from the Deep-Sea-Derived Fungus Aspergillus westerdijkiae DFFSCS013. J. Nat. Prod. 2013, 76, 983-987.
142. Yang, B.; Dong, J.; Lin, X.; Zhou, X.; Zhang, Y.; Liu, Y. New prenylated indole alkaloids from fungus Penicillium sp. derived of mangrove soil sample. Tetrahedron 2014, 70, 3859-3863.
143. Wang, F.; Fang, Y.; Zhu, T.; Zhang, M.; Lin, A.; Gu, Q.; Zhu, W. Seven new prenylated indole diketopiperazine alkaloids from holothurian-derived fungus Aspergillus fumigatus. Tetrahedron 2008, 64, 7986-7991.
144. Afiyatullov, S.S.; Zhuravleva, O.; Chaikina, E.; Anisimov, M. A new spirotryprostatin from the marine isolate of the fungus Aspergillus fumigatus. Chem. Nat. Compd. 2012, 48, 95-98.
145. Zhang, M.; Wang, W.-L.; Fang, Y.-C.; Zhu, T.-J.; Gu, Q.-Q.; Zhu, W.-M. Cytotoxic Alkaloids and Antibiotic Nordammarane Triterpenoids from the Marine-Derived Fungus Aspergillus sydowi. J. Nat. Prod. 2008, 71, 985-989.
146. He, F.; Sun, Y.-L.; Liu, K.-S.; Zhang, X.-Y.; Qian, P.-Y.; Wang, Y.-F.; Qi, S.-H. Indole alkaloids from marine-derived fungus Aspergillus sydowii SCSIO 00305. J. Antibiot. 2012, 65, 109-111.
147. Wang, Y.; Li, Z.-L.; Bai, J.; Zhang, L.-M.; Wu, X.; Zhang, L.; Pei, Y.-H.; Jing, Y.-K.; Hua, H.-M. 2, 5-Diketopiperazines from the Marine-Derived Fungus Aspergillus fumigatus YK-7. Chem. Biodiversity 2012, 9, 385-393.
148. An, C.-Y.; Li, X.-M.; Li, C.-S.; Xu, G.-M.; Wang, B.-G. Prenylated Indolediketopiperazine Peroxides and Related Homologues from the Marine Sediment-Derived Fungus Penicillium brefeldianum SD-273. Mar. Drugs 2014, 12, 746-756.
149. Zhuravleva, O.I.; Afiyatullov, S.S.; Denisenko, V.A.; Ermakova, S.P.; Slinkina, N.N.; Dmitrenok, P.S.; Kim, N.Y. Secondary metabolites from a marine-derived fungus Aspergillus carneus Blochwitz. Phytochemistry 2012, 80, 123-131.
150. Peng, J.; Gao, H.; Li, J.; Ai, J.; Geng, M.; Zhang, G.; Zhu, T.; Gu, Q.; Li, D. Prenylated Indole Diketopiperazines from the Marine-Derived Fungus Aspergillus versicolor. J. Org. Chem. 2014, 79, 7895-7904.
151. Song, F.; Liu, X.; Guo, H.; Ren, B.; Chen, C.; Piggott, A.M.; Yu, K.; Gao, H.; Wang, Q.; Liu, M.; et al. Brevianamides with Antitubercular Potential from a Marine-Derived Isolate of Aspergillus versicolor. Org. Lett. 2012, 14, 4770-4773.
152. Miao, F.-P.; Li, X.-D.; Liu, X.-H.; Cichewicz, R.H.; Ji, N.-Y. Secondary Metabolites from an Algicolous Aspergillus versicolor Strain. Mar. Drugs 2012, 10, 131-139.
153. Kong, X.; Cai, S.; Zhu, T.; Gu, Q.; Li, D.; Luan, Y. Secondary metabolites of a deep sea derived fungus Aspergillus versicolor CXCTD-06-6a and their bioactivity. J. Ocean Univ. China 2014, 13, 691-695.
154. Wang, W.-L.; Lu, Z.-Y.; Tao, H.-W.; Zhu, T.-J.; Fang, Y.-C.; Gu, Q.-Q.; Zhu, W.-M. Isoechinulin-type Alkaloids, Variecolorins A-L, from Halotolerant Aspergillus variecolor. J. Nat. Prod. 2007, 70, 1558-1564.
155. Zhou, L.-N.; Zhu, T.-J.; Cai, S.-X.; Gu, Q.-Q.; Li, D.-H. Three New Indole-Containing Diketopiperazine Alkaloids from a Deep-Ocean Sediment Derived Fungus Penicillium griseofulvum. Helvetica Chimica Acta 2010, 93, 1758-1763.
156. Du, F.-Y.; Li, X.-M.; Li, C.-S.; Shang, Z.; Wang, B.-G. Cristatumins A-D, new indole alkaloids from the marine-derived endophytic fungus Eurotium cristatum EN-220. Bioorg. Med. Chem. Lett. 2012, 22, 4650-4653.
157. Wang, W.-L.; Zhu, T.-J.; Tao, H.-W.; Lu, Z.-Y.; Fang, Y.-C.; Gu, Q.-Q.; Zhu, W.-M. Three Novel, Structurally Unique Spirocyclic Alkaloids from the Halotolerant B-17 Fungal Strain of Aspergillus variecolor. Chem. Biodiversity 2007, 4, 2913-2919.
158. Li, D.-L.; Li, X.-M.; Proksch, P.; Wang, B.-G. 7-O-Methylvariecolortide A, a new spirocyclic diketopiperazine alkaloid from a marine mangrove derived endophytic fungus, Eurotium rubrum. Nat. Prod. Commun. 2010, 5, 1583-1586.
159. Chen, G.-D.; Bao, Y.-R.; Huang, Y.-F.; Hu, D.; Li, X.-X.; Guo, L.-D.; Li, J.; Yao, X.-S.; Gao, H. Three pairs of variecolortide enantiomers from Eurotium sp. with caspase-3 inhibitory activity. Fitoterapia 2014, 92, 252-259.
160. Li, D.-L.; Li, X.-M.; Li, T.-G.; Dang, H.-Y.; Wang, B.-G. Dioxopiperazine Alkaloids Produced by the Marine Mangrove Derived Endophytic Fungus Eurotium rubrum. Helvetica Chimica Acta 2008, 91, 1888-1893.
161. Yan, H.-J.; Li, X.-M.; Li, C.-S.; Wang, B.-G. Alkaloid and Anthraquinone Derivatives Produced by the Marine-Derived Endophytic Fungus Eurotium rubrum. Helvetica Chimica Acta 2012, 95, 163-168.
162. Chen, X.; Si, L.; Liu, D.; Proksch, P.; Zhang, L.; Zhou, D.; Lin, W. Neoechinulin B and its analogues as potential entry inhibitors of influenza viruses, targeting viral hemagglutinin. Eur. J. Med. Chem. 2015, 93, 182-195.
163. Meng, L.-H.; Du, F.-Y.; Li, X.-M.; Pedpradab, P.; Xu, G.-M.; Wang, B.-G. Rubrumazines A-C, Indolediketopiperazines of the Isoechinulin Class from Eurotium rubrum MA-150, a Fungus Obtained from Marine Mangrove-Derived Rhizospheric Soil. J. Nat. Prod. 2015, 78, 909-913.
164. Gao, H.; Liu, W.; Zhu, T.; Mo, X.; Mandi, A.; Kurtan, T.; Li, J.; Ai, J.; Gu, Q.; Li, D. Diketopiperazine alkaloids from a mangrove rhizosphere soil derived fungus Aspergillus effuses H1-1. Org. Biomol. Chem. 2012, 10, 9501-9506.
165. Gao, H.; Zhu, T.; Li, D.; Gu, Q.; Liu, W. Prenylated indole diketopiperazine alkaloids from a mangrove rhizosphere soil derived fungus Aspergillus effuses H1-1. Arch. Pharmacal Res. 2013, 36, 952-956.
166. Zou, X.; Li, Y.; Zhang, X.; Li, Q.; Liu, X.; Huang, Y.; Tang, T.; Zheng, S.; Wang, W.; Tang, J. A New Prenylated Indole Diketopiperazine Alkaloid from Eurotium cristatum. Molecules 2014, 19, 17839-17847.
167. Gomes, N.M.; Dethoup, T.; Singburaudom, N.; Gales, L.; Silva, A.M.S.; Kijjoa, A. Eurocristatine, a new diketopiperazine dimer from the marine sponge-associated fungus Eurotium cristatum. Phytochemistry Letters 2012, 5, 717-720.
168. Sprogøe, K.; Manniche, S.; Larsen, T.O.; Christophersen, C. Janoxepin and brevicompanine B: Antiplasmodial metabolites from the fungus Aspergillus janus. Tetrahedron 2005, 61, 8718-8721.
169. Kusano, M.; Sotoma, G.; Koshino, H.; Uzawa, J.; Chijimatsu, M.; Fujioka, S.; Kawano, T.; Kimura, Y. Brevicompanines A and B: New plant growth regulators produced by the fungus, Penicillium brevicompactum. J. Chem. Soc., Perkin Trans. 1 1998, 2823-2826.
170. Kimura, Y.; Sawada, A.; Kuramata, M.; Kusano, M.; Fujioka, S.; Kawano, T.; Shimada, A. Brevicompanine C, Cyclo-(D-Ile-L-Trp), and Cyclo-(D-Leu-L-Trp), Plant Growth Regulators from Penicillium brevi-compactum. J. Nat. Prod. 2005, 68, 237-239.
171. Du, L.; Yang, X.; Zhu, T.; Wang, F.; Xiao, X.; Park, H.; Gu, Q. Diketopiperazine Alkaloids from a Deep Ocean Sediment Derived Fungus Penicillium sp. Chem. Pharm. Bull. 2009, 57, 873-876.
172. Raju, R.; Piggott, A.M.; Huang, X.-C.; Capon, R.J. Nocardioazines: A Novel Bridged Diketopiperazine Scaffold from a Marine-Derived Bacterium Inhibits P-Glycoprotein. Org. Lett. 2011, 13, 2770-2773.
173. Che, Q.; Zhu, T.; Qi, X.; Mándi, A.; Kurtán, T.; Mo, X.; Li, J.; Gu, Q.; Li, D. Hybrid Isoprenoids from a Reeds Rhizosphere Soil Derived Actinomycete Streptomyces sp. CHQ-64. Org. Lett. 2012, 14, 3438-3441.
174. Che, Q.; Zhu, T.; Keyzers, R.A.; Liu, X.; Li, J.; Gu, Q.; Li, D. Polycyclic Hybrid Isoprenoids from a Reed Rhizosphere Soil Derived Streptomyces sp. CHQ-64. J. Nat. Prod. 2013, 76, 759-763.
175. Cai, S.; Sun, S.; Peng, J.; Kong, X.; Zhou, H.; Zhu, T.; Gu, Q.; Li, D. Okaramines S-U, three new indole diketopiperazine alkaloids from Aspergillus taichungensis ZHN-7-07. Tetrahedron 2015, 71, 3715-3719.
176. Khalil, Z.G.; Huang, X.-C.; Raju, R.; Piggott, A.M.; Capon, R.J. Shornephine A: Structure, Chemical Stability, and P-Glycoprotein Inhibitory Properties of a Rare Diketomorpholine from an Australian Marine-Derived Aspergillus sp. J. Org. Chem. 2014, 79, 8700-8705.
177. Numata, A.; Takahashi, C.; Ito, Y.; Takada, T.; Kawai, K.; Usami, Y.; Matsumura, E.; Imachi, M.; Ito, T.; Hasegawa, T. Communesins, cytotoxic metabolites of a fungus isolated from a marine alga. Tetrahedron Lett. 1993, 34, 2355-2358.
178. Hayashi, H.; Matsumoto, H.; Akiyama, K. New Insecticidal Compounds, Communesins C, D and E, from Penicillium expansum Link MK-57. Biosci. Biotechnol. Biochem. 2004, 68, 753-756.
179. Jadulco, R.; Edrada, R.A.; Ebel, R.; Berg, A.; Schaumann, K.; Wray, V.; Steube, K.; Proksch, P. New Communesin Derivatives from the Fungus Penicillium sp. Derived from the Mediterranean Sponge Axinella verrucosa. J. Nat. Prod. 2004, 67, 78-81.
180. Dalsgaard, P.W.; Blunt, J.W.; Munro, M.H.G.; Frisvad, J.C.; Christophersen, C. Communesins G and H, New Alkaloids from the Psychrotolerant Fungus Penicillium rivulum. J. Nat. Prod. 2005, 68, 258-261.
181. Lin, H.-C.; Chiou, G.; Chooi, Y.-H.; McMahon, T.C.; Xu, W.; Garg, N.K.; Tang, Y. Elucidation of the Concise Biosynthetic Pathway of the Communesin Indole Alkaloids. Angew. Chem. Int. Ed. Engl. 2015, 127, 3047-3050.
182. Belofsky, G.N.; Gloer, J.B.; Wicklow, D.T.; Dowd, P.F. Antiinsectan alkaloids: Shearinines A-C and a new paxilline derivative from the ascostromata of Eupenicillium shearii. Tetrahedron 1995, 51, 3959-3968.
183. Xu, M.; Gessner, G.; Groth, I.; Lange, C.; Christner, A.; Bruhn, T.; Deng, Z.; Li, X.; Heinemann, S.H.; Grabley, S.; et al. Shearinines D-K, new indole triterpenoids from an endophytic Penicillium sp. (strain HKI0459) with blocking activity on large-conductance calcium-activated potassium channels. Tetrahedron 2007, 63, 435-444.
184. Smetanina, O.F.; Kalinovsky, A.I.; Khudyakova, Y.V.; Pivkin, M.V.; Dmitrenok, P.S.; Fedorov, S.N.; Ji, H.; Kwak, J.-Y.; Kuznetsova, T.A. Indole Alkaloids Produced by a Marine Fungus Isolate of Penicillium janthinellum Biourge. J. Nat. Prod. 2007, 70, 906-909.
185. Smetanina, O.F.; Kalinovsky, A.I.; Khudyakova, Y.V.; Dmitrenok, P.S.; Federov, S.N.; Ji, H.; Kwak, J.-Y.; Kuznetsova, T.A. Indole Alkaloids Produced by a Marine Fungus Isolate of Penicillium janthinellum Biourge. J. Nat. Prod. 2007, 70, 906-909.
186. Belofsky, G.N.; Gloer, J.B.; Wicklow, D.T.; Dowd, P.F. Indole Antiinsectan Metabolites from the Ascostromata of Eupenicillium shearii. U.S. Patent 5, 492, 902 A, 20 February 1996.
187. You, J.; Du, L.; King, J.B.; Hall, B.E.; Cichewicz, R.H. Small-Molecule Suppressors of Candida albicans Biofilm Formation Synergistically Enhance the Antifungal Activity of Amphotericin B against Clinical Candida Isolates. ACS Chem. Biol. 2013, 8, 840-848.
188. Qiao, M.-F.; Ji, N.-Y.; Liu, X.-H.; Li, K.; Zhu, Q.-M.; Xue, Q.-Z. Indoloditerpenes from an algicolous isolate of Aspergillus oryzae. Bioorg. Med. Chem. Lett. 2010, 20, 5677-5680.
189. Tsuda, M.; Kasai, Y.; Komatsu, K.; Sone, T.; Tanaka, M.; Mikami, Y.; Kobayashi, J.I. Citrinadin A, a Novel Pentacyclic Alkaloid from Marine-Derived Fungus Penicillium citrinum. Org. Lett. 2004, 6, 3087-3089.
190. Mugishima, T.; Tsuda, M.; Kasai, Y.; Ishiyama, H.; Fukushi, E.; Kawabata, J.; Watanabe, M.; Akao, K.; Kobayashi, J.I. Absolute Stereochemistry of Citrinadins A and B from Marine-Derived Fungus. J. Org. Chem. 2005, 70, 9430-9435.
191. Nakae, K.; Hosokawa, N.; Sawa, R.; Kubota, Y.; Masuda, T.; Ohba, S.; Igarashi, M.; Nakagawa, N.; Nishimura, Y.; Akamatsu, Y. A New Teleocidin Analog from Streptomyces sp. MM216-87F4 Induces Substance P Release from Rat Dorsal Root Ganglion Neurons. J. Antibiot. 2006, 59, 11-17.
192. Izumikawa, M.; Khan, S.T.; Komaki, H.; Takagi, M.; Shin-ya, K. JBIR-31, a new teleocidin analog, produced by salt-requiring Streptomyces sp. NBRC 105896 isolated from a marine sponge. J. Antibiot. 2009, 63, 33-36.
193. Jiang, W.; Tan, S.; Hanaki, Y.; Irie, K.; Uchida, H.; Watanabe, R.; Suzuki, T.; Sakamoto, B.; Kamio, M.; Nagai, H. Two New Lyngbyatoxin Derivatives from the Cyanobacterium, Moorea producens. Mar. Drugs 2014, 12, 5788-5800.
194. Jiang, W.; Zhou, W.; Uchida, H.; Kikumori, M.; Irie, K.; Watanabe, R.; Suzuki, T.; Sakamoto, B.; Kamio, M.; Nagai, H. A New Lyngbyatoxin from the Hawaiian Cyanobacterium Moorea producens. Mar. Drugs 2014, 12, 2748-2759.
195. Huang, H.; Yao, Y.; He, Z.; Yang, T.; Ma, J.; Tian, X.; Li, Y.; Huang, C.; Chen, X.; Li, W.; et al. Antimalarial β-Carboline and Indolactam Alkaloids from Marinactinospora thermotolerans, a Deep Sea Isolate. J. Nat. Prod. 2011, 74, 2122-2127.
196. Du, L.; Li, D.; Zhu, T.; Cai, S.; Wang, F.; Xiao, X.; Gu, Q. New alkaloids and diterpenes from a deep ocean sediment derived fungus Penicillium sp. Tetrahedron 2009, 65, 1033-1039.
197. Du, L.; Feng, T.; Zhao, B.; Li, D.; Cai, S.; Zhu, T.; Wang, F.; Xiao, X.; Gu, Q. Alkaloids from a deep ocean sediment-derived fungus Penicillium sp. and their antitumor activities. J. Antibiot. 2010, 63, 165-170.
198. Ding, L.; Münch, J.; Goerls, H.; Maier, A.; Fiebig, H.-H.; Lin, W.-H.; Hertweck, C. Xiamycin, a pentacyclic indolosesquiterpene with selective anti-HIV activity from a bacterial mangrove endophyte. Bioorg. Med. Chem. Lett. 2010, 20, 6685-6687.
199. Ding, L.; Maier, A.; Fiebig, H.-H.; Lin, W.-H.; Hertweck, C. A family of multicyclic indolosesquiterpenes from a bacterial endophyte. Org. Biomol. Chem. 2011, 9, 4029-4031.
200. Zhang, Q.; Mándi, A.; Li, S.; Chen, Y.; Zhang, W.; Tian, X.; Zhang, H.; Li, H.; Zhang, W.; Zhang, S.; et al. N-N-Coupled Indolo-sesquiterpene Atropo-Diastereomers from a Marine-Derived Actinomycete. Eur. J. Org. Chem. 2012, 2012, 5256-5262.
201. Sallam, A.A.; Houssen, W.E.; Gissendanner, C.R.; Orabi, K.Y.; Foudah, A.I.; El Sayed, K.A. Bioguided discovery and pharmacophore modeling of the mycotoxic indole diterpene alkaloids penitrems as breast cancer proliferation, migration, and invasion inhibitors. Med. Chem. Comm. 2013, 4, 1360-1369.
202. Zhang, P.; Li, X.-M.; Li, X.; Wang, B.-G. New indole-diterpenoids from the algal-associated fungus Aspergillus nidulans. Phytochem. Lett. 2015, 12, 182-185.
203. Fan, Y.; Wang, Y.; Liu, P.; Fu, P.; Zhu, T.; Wang, W.; Zhu, W. Indole-Diterpenoids with Anti-H1N1 Activity from the Aciduric Fungus Penicillium camemberti OUCMDZ-1492. J. Nat. Prod. 2013, 76, 1328-1336.
204. Harms, H.; Rempel, V.; Kehraus, S.; Kaiser, M.; Hufendiek, P.; Müller, C.E.; König, G.M. Indoloditerpenes from a Marine-Derived Fungal Strain of Dichotomomyces cejpii with Antagonistic Activity at GPR18 and Cannabinoid Receptors. J. Nat. Prod. 2014, 77, 673-677.
205. Makarieva, T.N.; Ilyin, S.G.; Stonik, V.A.; Lyssenko, K.A.; Denisenko, V.A. Pibocin, the first ergoline marine alkaloid from the Far-Eastern ascidian Eudistoma sp. Tetrahedron Lett. 1999, 40, 1591-1594.
206. Makarieva, T.N.; Dmitrenok, A.S.; Dmitrenok, P.S.; Grebnev, B.B.; Stonik, V.A. Pibocin B, the First N-O-Methylindole Marine Alkaloid, a Metabolite from the Far-Eastern Ascidian Eudistoma Species. J. Nat. Prod. 2001, 64, 1559-1561.
207. Spilsbury, J.F.; Wilkinson, S. The isolation of festuclavine and two new clavine alkaloids from Aspergillus fumigatus Fres. J. Chem. Soc. 1961, 2081-2091, doi:10.1039/jr9610002085.
208. Cole, R.J.; Kirksey, J.W.; Dorner, J.W.; Wilson, D.M.; Johnson, J.C.; Johnson, A.N.; Bedell, D.M.; Springer, J.P.; Chexal, K.K. Mycotoxins produced by Aspergillus fumigatus species isolated from molded silage. J. Agric. Food Chem. 1977, 25, 826-830.
209. Zhang, D.; Satake, M.; Fukuzawa, S.; Sugahara, K.; Niitsu, A.; Shirai, T.; Tachibana, K. Two new indole alkaloids, 2-(3, 3-dimethylprop-1-ene)-costaclavine and 2-(3, 3-dimethylprop-1-ene)- epicostaclavine, from the marine-derived fungus Aspergillus fumigatus. J. Nat. Med. 2012, 66, 222-226.
210. Li, Y.-X.; Himaya, S.W.A.; Dewapriya, P.; Zhang, C.; Kim, S.-K. Fumigaclavine C from a Marine-Derived Fungus Aspergillus fumigatus Induces Apoptosis in MCF-7 Breast Cancer Cells. Mar. Drugs 2013, 11, 5063-5086.
211. Wakimoto, T.; Tan, K.C.; Abe, I. Ergot alkaloid from the sea slug Pleurobranchus forskalii. Toxicon 2013, 72, 1-4.
212. Yang, C.-G.; Huang, H.; Jiang, B. Progress in Studies of Novel Marine Bis(indole) Alkaloids. Curr. Org. Chem. 2004, 8, 1691-1720.
213. Leena, G.; Archna, T.; Prem, M.S.C. Bis and Tris Indole Alkaloids from Marine Organisms: New Leads for Drug Discovery. Curr. Med. Chem. 2007, 14, 1789-1803.
214. Veluri, R.; Oka, I.; Wagner-Döbler, I.; Laatsch, H. New Indole Alkaloids from the North Sea Bacterium Vibrio parahaemolyticus Bio2491. J. Nat. Prod. 2003, 66, 1520-1523.
215. Tsuda, M.; Takahashi, Y.; Fromont, J.; Mikami, Y.; Kobayashi, J.I. Dendridine A, a Bis-indole Alkaloid from a Marine Sponge Dictyodendrilla Species. J. Nat. Prod. 2005, 68, 1277-1278.
216. Endo, T.; Tsuda, M.; Fromont, J.; Kobayashi, J.I. Hyrtinadine A, a Bis-indole Alkaloid from a Marine Sponge. J. Nat. Prod. 2007, 70, 423-424.
217. Cai, S.-X.; Li, D.-H.; Zhu, T.-J.; Wang, F.-P.; Xiao, X.; Gu, Q.-Q. Two New Indole Alkaloids from the Marine-Derived Bacterium Aeromonas sp. CB101. Helvetica Chimica Acta 2010, 93, 791-795.
218. Yan, X.; Tang, X.-X.; Chen, L.; Yi, Z.-W.; Fang, M.-J.; Wu, Z.; Qiu, Y.-K. Two New Cytotoxic Indole Alkaloids from a Deep-Sea Sediment Derived Metagenomic Clone. Mar. Drugs 2014, 12, 2156-2163.
219. Abe, T.; Kukita, A.; Akiyama, K.; Naito, T.; Uemura, D. Isolation and Structure of a Novel Biindole Pigment Substituted with an Ethyl Group from a Metagenomic Library Derived from the Marine Sponge Halichondria okadai. Chem. Lett. 2012, 41, 728-729.
220. Li, J.L.; Huang, L.; Liu, J.; Song, Y.; Gao, J.; Jung, J.H.; Liu, Y.; Chen, G. Acetylcholinesterase inhibitory dimeric indole derivatives from the marine actinomycetes Rubrobacter radiotolerans. Fitoterapia 2015, 102, 203-207.
221. Rubnov, S.; Chevallier, C.; Thoison, O.; Debitus, C.; Laprevote, O.; Guénard, D.; Sévenet, T. Echinosulfonic acid D: An ESI MSn evaluation of a new cytotoxic alkaloid from the New-Caledonian sponge Psammoclemma sp. Nat. Prod. Res. 2005, 19, 75-79.
222. Yamada, T.; Iwamoto, C.; Yamagaki, N.; Yamanouchi, T.; Minoura, K.; Hagishita, S.; Numata, A. Leptosins O-S, cytotoxic metabolites of a strain of Leptosphaeria sp. isolated from a marine alga. Heterocycles 2004, 63, 641-653.
223. Usami, Y.; Yamaguchi, J.; Numata, A. Gliocladins A-C and glioperazine; cytotoxic dioxo- or trioxopiperazine metabolites from a Gliocladium sp. separated from a sea hare. Heterocycles 2004, 63, 1123-1129.
224. Han, X.-X.; Cui, C.-B.; Gu, Q.-Q.; Zhu, W.-M.; Liu, H.-B.; Gu, J.-Y.; Osada, H. ZHD-0501, a novel naturally occurring staurosporine analog from Actinomadura sp. 007. Tetrahedron Lett. 2005, 46, 6137-6140.
225. Wu, S.J.; Fotso, S.; Li, F.; Qin, S.; Kelter, G.; Fiebig, H.H.; Laatsch, H. N-Carboxamidostaurosporine and Selina-4(14), 7(11)-diene-8, 9-diol, New Metabolites from a Marine Streptomyces sp. J. Antibiot. 2006, 59, 331-337.
226. Reyes, F.; Fernández, R.; Rodríguez, A.; Bueno, S.; de Eguilior, C.; Francesch, A.; Cuevas, C. Cytotoxic Staurosporines from the Marine Ascidian Cystodytes solitus. J. Nat. Prod. 2008, 71, 1046-1048.
227. Jimenez, P.C.; Wilke, D.V.; Ferreira, E.G.; Takeara, R.; de Moraes, M.O.; Silveira, E.R.; da Cruz Lotufo, T.M.; Lopes, N.P.; Costa-Lotufo, L.V. Structure Elucidation and Anticancer Activity of 7-Oxostaurosporine Derivatives from the Brazilian Endemic Tunicate Eudistoma vannamei. Mar. Drugs 2012, 10, 1092-1102.
228. Fu, P.; Yang, C.; Wang, Y.; Liu, P.; Ma, Y.; Xu, L.; Su, M.; Hong, K.; Zhu, W. Streptocarbazoles A and B, Two Novel Indolocarbazoles from the Marine-Derived Actinomycete Strain Streptomyces sp. FMA. Org. Lett. 2012, 14, 2422-2425.
229. Fu, P.; Zhuang, Y.; Wang, Y.; Liu, P.; Qi, X.; Gu, K.; Zhang, D.; Zhu, W. New Indolocarbazoles from a Mutant Strain of the Marine-Derived Actinomycete Streptomyces fradiae 007M135. Org. Lett. 2012, 14, 6194-6197.
230. Warabi, K.; Matsunaga, S.; van Soest, R.W.M.; Fusetani, N. Dictyodendrins A-E, the First Telomerase-Inhibitory Marine Natural Products from the Sponge Dictyodendrilla verongiformis. J. Org. Chem. 2003, 68, 2765-2770.
231. Zhang, H.; Conte, M.M.; Khalil, Z.; Huang, X.-C.; Capon, R.J. New dictyodendrins as BACE inhibitors from a southern Australian marine sponge, Ianthella sp. RSC Advances 2012, 2, 4209-4214.
232. Iwagawa, T.; Miyazaki, M.; Okamura, H.; Nakatani, M.; Doe, M.; Takemura, K. Three novel bis(indole) alkaloids from a stony coral, Tubastraea sp. Tetrahedron Lett. 2003, 44, 2533-2535.
233. Balansa, W.; Islam, R.; Gilbert, D.F.; Fontaine, F.; Xiao, X.; Zhang, H.; Piggott, A.M.; Lynch, J.W.; Capon, R.J. Australian marine sponge alkaloids as a new class of glycine-gated chloride channel receptor modulator. Bioorg. Med. Chem. 2013, 21, 4420-4425.
234. Iwagawa, T.; Miyazaki, M.; Yokogawa, Y.; Okamura, H.; Nakatani, M.; Doe, M.; Morimoto, Y.; Takemura, K. Aplysinopsin dimers from a stony coral Tubastraea aurea. Heterocycles 2008, 75, 2023-2028.
235. Meyer, M.; Delberghe, F.; Liron, F.; Guillaume, M.; Valentin, A.; Guyot, M. An antiplasmodial new (bis)indole alkaloid from the hard coral Tubastraea sp. Nat. Prod. Res. 2009, 23, 178-182.
236. Tan, R.X.; Jensen, P.R.; Williams, P.G.; Fenical, W. Isolation and Structure Assignments of Rostratins A-D, Cytotoxic Disulfides Produced by the Marine-Derived Fungus Exserohilum rostratum. J. Nat. Prod. 2004, 67, 1374-1382.
237. Ovenden, S.P.B.; Sberna, G.; Tait, R.M.; Wildman, H.G.; Patel, R.; Li, B.; Steffy, K.; Nguyen, N.; Meurer-Grimes, B.M. A Diketopiperazine Dimer from a Marine-Derived Isolate of Aspergillus niger. J. Nat. Prod. 2004, 67, 2093-2095.
238. Oh, K.-B.; Mar, W.; Kim, S.; Kim, J.-Y.; Oh, M.-N.; Kim, J.-G.; Shin, D.; Sim, C.J.; Shin, J. Bis(indole) alkaloids as sortase A inhibitors from the sponge Spongosorites sp. Bioorg. Med. Chem. Lett. 2005, 15, 4927-4931.
239. Bao, B.; Sun, Q.; Yao, X.; Hong, J.; Lee, C.-O.; Sim, C.J.; Im, K.S.; Jung, J.H. Cytotoxic Bisindole Alkaloids from a Marine Sponge Spongosorites sp. J. Nat. Prod. 2005, 68, 711-715.
240. Bao, B.; Sun, Q.; Yao, X.; Hong, J.; Lee, C.-O.; Cho, H.Y.; Jung, J.H. Bisindole Alkaloids of the Topsentin and Hamacanthin Classes from a Marine Sponge Spongosorites sp. J. Nat. Prod. 2007, 70, 2-8.
241. Oh, K.-B.; Mar, W.; Kim, S.; Kim, J.-Y.; Lee, T.-H.; Kim, J.-G.; Shin, D.; Sim, C.J.; Shin, J. Antimicrobial activity and cytotoxicity of bis(indole) alkaloids from the sponge Spongosorites sp. Biol. Pharm. Bull. 2006, 29, 570-573.
242. Kim, G.; Cheong, O.; Bae, S.; Shin, J.; Lee, S. 6′-Debromohamacanthin A, a Bis (Indole) Alkaloid, Inhibits Angiogenesis by Targeting the VEGFR2-Mediated PI3K/AKT/mTOR Signaling Pathways. Mar. Drugs 2013, 11, 1087-1103.
243. Sun, W.-S.; Su, S.; Zhu, R.-X.; Tu, G.-Z.; Cheng, W.; Liang, H.; Guo, X.-Y.; Zhao, Y.-Y.; Zhang, Q.-Y. A pair of unprecedented spiro-trisindole enantiomers fused through a five-member ring from Laurencia similis. Tetrahedron Lett. 2013, 54, 3617-3620.
244. Dai, J.; Jiménez, J.I.; Kelly, M.; Barnes, S.; Lorenzo, P.; Williams, P. Dictazolines A and B, Bisspiroimidazolidinones from the Marine Sponge Smenospongia cerebriformis. J. Nat. Prod. 2008, 71, 1287-1290.
245. Dai, J.; Jiménez, J.I.; Kelly, M.; Williams, P.G. Dictazoles: Potential Vinyl Cyclobutane Biosynthetic Precursors to the Dictazolines. J. Org. Chem. 2010, 75, 2399-2402.
246. Tapiolas, D.M.; Bowden, B.F.; Abou-Mansour, E.; Willis, R.H.; Doyle, J.R.; Muirhead, A.N.; Liptrot, C.; Llewellyn, L.E.; Wolff, C.W.W.; Wright, A.D.; et al. Eusynstyelamides A, B, and C, nNOS Inhibitors, from the Ascidian Eusynstyela latericius. J. Nat. Prod. 2009, 72, 1115-1120.
247. Tadesse, M.; Tabudravu, J.N.; Jaspars, M.; Strøm, M.B.; Hansen, E.; Andersen, J.H.; Kristiansen, P.E.; Haug, T. The Antibacterial ent-Eusynstyelamide B and Eusynstyelamides D, E, and F from the Arctic Bryozoan Tegella cf. spitzbergensis. J. Nat. Prod. 2011, 74, 837-841.
248. Liberio, M.; Sadowski, M.; Nelson, C.; Davis, R. Identification of Eusynstyelamide B as a Potent Cell Cycle Inhibitor Following the Generation and Screening of an Ascidian-Derived Extract Library Using a Real Time Cell Analyzer. Mar. Drugs 2014, 12, 5222-5239.
249. Liberio, M.; Sadowski, M.; Rockstroh, A.; Vasireddy, R.; Quinn, R.J.; Davis, R.A.; Nelson, C. Scientific Programme-Proffered Papers. Eur. J. Cancer 2013, 49 (Suppl. 2), S177-S178.
250. Raju, R.; Piggott, A.M.; Conte, M.; Aalbersberg, W.G.L.; Feussner, K.; Capon, R.J. Naseseazines A and B: A New Dimeric Diketopiperazine Framework from a Marine-Derived Actinomycete, Streptomyces sp. Org. Lett. 2009, 11, 3862-3865.
251. Carr, G.; Tay, W.; Bottriell, H.; Andersen, S.K.; Mauk, A.G.; Andersen, R.J. Plectosphaeroic Acids A, B, and C, Indoleamine 2, 3-Dioxygenase Inhibitors Produced in Culture by a Marine Isolate of the Fungus Plectosphaerella cucumerina. Org. Lett. 2009, 11, 2996-2999.
252. Wei, X.; Henriksen, N.M.; Skalicky, J.J.; Harper, M.K.; Cheatham, T.E.; Ireland, C.M.; Van Wagoner, R.M. Araiosamines A-D: Tris-bromoindole Cyclic Guanidine Alkaloids from the Marine Sponge Clathria (Thalysias) araiosa. J. Org. Chem. 2011, 76, 5515-5523.
253. Cai, S.; Kong, X.; Wang, W.; Zhou, H.; Zhu, T.; Li, D.; Gu, Q. Aspergilazine A, a diketopiperazine dimer with a rare N-1 to C-6 linkage, from a marine-derived fungus Aspergillus taichungensis. Tetrahedron Lett. 2012, 53, 2615-2617; Corrigendum in 2014, 55, 5404.
254. Wang, F.-Z.; Huang, Z.; Shi, X.-F.; Chen, Y.-C.; Zhang, W.-M.; Tian, X.-P.; Li, J.; Zhang, S. Cytotoxic indole diketopiperazines from the deep sea-derived fungus Acrostalagmus luteoalbus SCSIO F457. Bioorg. Med. Chem. Lett. 2012, 22, 7265-7267.
255. Liu, D.-Q.; Mao, S.-C.; Zhang, H.-Y.; Yu, X.-Q.; Feng, M.-T.; Wang, B.; Feng, L.-H.; Guo, Y.-W. Racemosins A and B, two novel bisindole alkaloids from the green alga Caulerpa racemosa. Fitoterapia 2013, 91, 15-20.
256. Yang, H.; Liu, D.-Q.; Liang, T.-J.; Li, J.; Liu, A.-H.; Yang, P.; Lin, K.; Yu, X.-Q.; Guo, Y.-W.; Mao, S.-C.; et al. Racemosin C, a novel minor bisindole alkaloid with protein tyrosine phosphatase-1B inhibitory activity from the green alga Caulerpa racemosa. J. Asian. Nat. Prod. Res. 2014, 16, 1158-1165.
257. Liu, D.-Q.; Mao, S.-C.; Yu, X.-Q.; Feng, L.-H.; Lai, X.-P. Caulerchlorin, a Novel Chlorinated Bisindole Alkaloid with Antifungal Activity from the Chinese Green Alga Caulerpa racemosa. Heterocycles 2012, 85, 661-666.
258. Momose, R.; Tanaka, N.; Fromont, J.; Kobayashi, J.I. Hyrtimomines A-C, New Heteroaromatic Alkaloids from a Sponge Hyrtios sp. Org. Lett. 2013, 15, 2010-2013.
259. Tanaka, N.; Momose, R.; Takahashi, Y.; Kubota, T.; Takahashi-Nakaguchi, A.; Gonoi, T.; Fromont, J.; Kobayashi, J.I. Hyrtimomines D and E, bisindole alkaloids from a marine sponge Hyrtios sp. Tetrahedron Lett. 2013, 54, 4038-4040.
260. Tanaka, N.; Momose, R.; Takahashi-Nakaguchi, A.; Gonoi, T.; Fromont, J.; Kobayashi, J.I. Hyrtimomines, indole alkaloids from Okinawan marine sponges Hyrtios spp. Tetrahedron 2014, 70, 832-837.
261. McArthur, K.A.; Mitchell, S.S.; Tsueng, G.; Rheingold, A.; White, D.J.; Grodberg, J.; Lam, K.S.; Potts, B.C.M. Lynamicins A-E, Chlorinated Bisindole Pyrrole Antibiotics from a Novel Marine Actinomycete. J. Nat. Prod. 2008, 71, 1732-1737.
262. Zhang, W.; Liu, Z.; Li, S.; Yang, T.; Zhang, Q.; Ma, L.; Tian, X.; Zhang, H.; Huang, C.; Zhang, S.; et al. Spiroindimicins A-D: New Bisindole Alkaloids from a Deep-Sea-Derived Actinomycete. Org. Lett. 2012, 14, 3364-3367.
263. Zhang, W.; Ma, L.; Li, S.; Liu, Z.; Chen, Y.; Zhang, H.; Zhang, G.; Zhang, Q.; Tian, X.; Yuan, C.; et al. Indimicins A-E, Bisindole Alkaloids from the Deep-Sea-Derived Streptomyces sp. SCSIO 03032. J. Nat. Prod. 2014, 77, 1887-1892.
264. Saurav, K.; Zhang, W.; Saha, S.; Zhang, H.; Li, S.; Zhang, Q.; Wu, Z.; Zhang, G.; Zhu, Y.; Verma, G. In silico molecular docking, preclinical evaluation of spiroindimicins A-D, lynamicin A and D isolated from deep marine sea derived Streptomyces sp. SCSIO 03032. Interdiscip. Sci. Comput. Life Sci. 2014, 6, 187-196.
265. Meng, L.-H.; Li, X.-M.; Lv, C.-T.; Huang, C.-G.; Wang, B.-G. Brocazines A-F, Cytotoxic Bisthiodiketopiperazine Derivatives from Penicillium brocae MA-231, an Endophytic Fungus Derived from the Marine Mangrove Plant Avicennia marina. J. Nat. Prod. 2014, 77, 1921-1927.
266. Reyes, F.; Martín, R.; Rueda, A.; Fernández, R.; Montalvo, D.; Gómez, C.; Sánchez-Puelles, J.M. Discorhabdins I and L, Cytotoxic Alkaloids from the Sponge Latrunculia brevis. J. Nat. Prod. 2004, 67, 463-465.
267. Antunes, E.M.; Beukes, D.R.; Kelly, M.; Samaai, T.; Barrows, L.R.; Marshall, K.M.; Sincich, C.; Davies-Coleman, M.T. Cytotoxic Pyrroloiminoquinones from Four New Species of South African Latrunculid Sponges. J. Nat. Prod. 2004, 67, 1268-1276.
268. Lang, G.; Pinkert, A.; Blunt, J.W.; Munro, M.H.G. Discorhabdin W, the First Dimeric Discorhabdin. J. Nat. Prod. 2005, 68, 1796-1798.
269. El-Naggar, M.; Capon, R.J. Discorhabdins Revisited: Cytotoxic Alkaloids from Southern Australian Marine Sponges of the Genera Higginsia and Spongosorites. J. Nat. Prod. 2009, 72, 460-464.
270. Na, M.; Ding, Y.; Wang, B.; Tekwani, B.L.; Schinazi, R.F.; Franzblau, S.; Kelly, M.; Stone, R.; Li, X.-C.; Ferreira, D.; et al. Anti-infective Discorhabdins from a Deep-Water Alaskan Sponge of the Genus Latrunculia. J. Nat. Prod. 2010, 73, 383-387.
271. Jeon, J.-E.; Na, Z.; Jung, M.; Lee, H.-S.; Sim, C.J.; Nahm, K.; Oh, K.-B.; Shin, J. Discorhabdins from the Korean Marine Sponge Sceptrella sp. J. Nat. Prod. 2010, 73, 258-262.
272. Davis, R.A.; Buchanan, M.S.; Duffy, S.; Avery, V.M.; Charman, S.A.; Charman, W.N.; White, K.L.; Shackleford, D.M.; Edstein, M.D.; Andrews, K.T.; et al. Antimalarial Activity of Pyrroloiminoquinones from the Australian Marine Sponge Zyzzya sp. J. Med. Chem. 2012, 55, 5851-5858.
273. Keyzers, R.A.; Samaai, T.; Davies-Coleman, M.T. Novel pyrroloquinoline ribosides from the South African latrunculid sponge Strongylodesma aliwaliensis. Tetrahedron Lett. 2004, 45, 9415-9418.
274. Whibley, C.E.; Keyzers, R.A.; Soper, A.G.; Davies-Coleman, M.T.; Samaai, T.; Hendricks, D.T. Antiesophageal Cancer Activity from Southern African Marine Organisms. Ann. N. Y. Acad. Sci. 2005, 1056, 405-412.
275. Utkina, N.K.; Makarchenko, A.E.; Denisenko, V.A.; Dmitrenok, P.S. Zyzzyanone A, a novel pyrrolo[3, 2-f]indole alkaloid from the Australian marine sponge Zyzzya fuliginosa. Tetrahedron Lett. 2004, 45, 7491-7494.
276. Utkina, N.K.; Makarchenko, A.E.; Denisenko, V.A. Zyzzyanones B-D, Dipyrroloquinones from the Marine Sponge Zyzzya fuliginosa. J. Nat. Prod. 2005, 68, 1424-1427.
277. Makarchenko, A.E.; Utkina, N.K. UV-stability and UV-protective activity of alkaloids from the marine sponge Zyzzya fuliginosa. Chem Nat Compd 2006, 42, 78-81.
278. Utkina, N.K.; Denisenko, V.A. Ophiuroidine, the first indolo[2, 1-b]quinazoline alkaloid from the Caribbean brittle star Ophiocoma riisei. Tetrahedron Lett. 2007, 48, 4445-4447.
279. Han, X.-X.; Xu, X.-Y.; Cui, C.-B.; Gu, Q.-Q. Alkaloidal compounds produced by a marine-derived fungus, Aspergillus fumigatus H1-04, and their antitumor activities. Chin. J. Med. Chem. 2007, 17, 232-237.
280. Zhou, Y.; Debbab, A.; Mándi, A.; Wray, V.; Schulz, B.; Müller, W.E.G.; Kassack, M.; Lin, W.; Kurtán, T.; Proksch, P.; et al. Alkaloids from the Sponge-Associated Fungus Aspergillus sp. Eur. J. Org. Chem. 2013, 2013, 894-906.
281. Afiyatullov, S.S.; Zhuravleva, O.I.; Antonov, A.S.; Kalinovsky, A.I.; Pivkin, M.V.; Menchinskaya, E.S.; Aminin, D.L. New metabolites from the marine-derived fungus Aspergillus fumigatus. Nat. Prod. Commun. 2012, 7, 497-500.
282. Shao, C.-L.; Xu, R.-F.; Wei, M.-Y.; She, Z.-G.; Wang, C.-Y. Structure and Absolute Configuration of Fumiquinazoline L, an Alkaloid from a Gorgonian-Derived Scopulariopsis sp. Fungus. J. Nat. Prod. 2013, 76, 779-782.
283. Liao, L.; You, M.; Chung, B.K.; Oh, D.-C.; Oh, K.-B.; Shin, J. Alkaloidal Metabolites from a Marine-Derived Aspergillus sp. Fungus. J. Nat. Prod. 2015, 78, 349-354.
284. Fremlin, L.J.; Piggott, A.M.; Lacey, E.; Capon, R.J. Cottoquinazoline A and Cotteslosins A and B, Metabolites from an Australian Marine-Derived Strain of Aspergillus versicolor. J. Nat. Prod. 2009, 72, 666-670.
285. Zhuang, Y.; Teng, X.; Wang, Y.; Liu, P.; Li, G.; Zhu, W. New Quinazolinone Alkaloids within Rare Amino Acid Residue from Coral-Associated Fungus, Aspergillus versicolor LCJ-5-4. Org. Lett. 2011, 13, 1130-1133.
286. Liu, J.; Wei, X.; La Kim, E.; Lin, X.; Yang, X.-W.; Zhou, X.; Yang, B.; Jung, J.H.; Liu, Y. New glucosidated pyrazinoquinazoline indole alkaloids from fungus Aspergillus fumigatus derived of a jellyfish. Tetrahedron 2015, 71, 271-275.
287. Qi, S.-H.; Su, G.-C.; Wang, Y.-F.; Liu, Q.-Y.; Gao, C.-H. Alkaloids from the South China Sea Black Coral Antipathes dichotoma. Chem. Pharm. Bull. 2009, 57, 87-88.
288. Wu, Q.-X.; Crews, M.S.; Draskovic, M.; Sohn, J.; Johnson, T.A.; Tenney, K.; Valeriote, F.A.; Yao, X.-J.; Bjeldanes, L.F.; Crews, P. Azonazine, a Novel Dipeptide from a Hawaiian Marine Sediment-Derived Fungus, Aspergillus insulicola. Org. Lett. 2010, 12, 4458-4461.
289. Lee, S.U.; Asami, Y.; Lee, D.; Jang, J.-H.; Ahn, J.S.; Oh, H. Protuboxepins A and B and Protubonines A and B from the Marine-Derived Fungus Aspergillus sp. SF-5044. J. Nat. Prod. 2011, 74, 1284-1287.
290. An, C.-Y.; Li, X.-M.; Li, C.-S.; Wang, M.-H.; Xu, G.-M.; Wang, B.-G. Aniquinazolines A-D, Four New Quinazolinone Alkaloids from Marine-Derived Endophytic Fungus Aspergillus nidulans. Mar. Drugs 2013, 11, 2682.
291. Lyakhova, E.G.; Kolesnikova, S.A.; Kalinovsky, A.I.; Afiyatullov, S.S.; Dyshlovoy, S.A.; Krasokhin, V.B.; Minh, C.V.; Stonik, V.A. Bromine-containing alkaloids from the marine sponge Penares sp. Tetrahedron Lett. 2012, 53, 6119-6122.
292. Xu, N.; Cao, Y.; Wang, L.; Chen, G.; Pei, Y.-H. New alkaloids from a marine-derived fungus Neosartorya sp. HN-M-3. J. Asian. Nat. Prod. Res. 2013, 15, 731-736.
293. Sun, F.-Y.; Chen, G.; Bai, J.; Li, W.; Pei, Y.-H. Two new alkaloids from a marine-derived fungus Neosartorya sp. HN-M-3. J. Asian. Nat. Prod. Res. 2012, 14, 1109-1115.
294. Khokhar, S.; Feng, Y.; Campitelli, M.R.; Quinn, R.J.; Hooper, J.N.A.; Ekins, M.G.; Davis, R.A. Trikentramides A-D, Indole Alkaloids from the Australian Sponge Trikentrion flabelliforme. J. Nat. Prod. 2013, 76, 2100-2105.
295. Dong, J.-J.; Bao, J.; Zhang, X.-Y.; Xu, X.-Y.; Nong, X.-H.; Qi, S.-H. Alkaloids and citrinins from marine-derived fungus Nigrospora oryzae SCSGAF 0111. Tetrahedron Lett. 2014, 55, 2749-2753.
296. Yamanokuchi, R.; Imada, K.; Miyazaki, M.; Kato, H.; Watanabe, T.; Fujimuro, M.; Saeki, Y.; Yoshinaga, S.; Terasawa, H.; Iwasaki, N.; et al. Hyrtioreticulins A-E, indole alkaloids inhibiting the ubiquitin-activating enzyme, from the marine sponge Hyrtios reticulatus. Bioorg. Med. Chem. 2012, 20, 4437-4442.
297. Imada, K.; Sakai, E.; Kato, H.; Kawabata, T.; Yoshinaga, S.; Nehira, T.; Terasawa, H.; Tsukamoto, S. Reticulatins A and B and hyrtioreticulin F from the marine sponge Hyrtios reticulatus. Tetrahedron 2013, 69, 7051-7055.
298. Ji, N.-Y.; Liu, X.-H.; Miao, F.-P.; Qiao, M.-F. Aspeverin, a New Alkaloid from an Algicolous Strain of Aspergillus versicolor. Org. Lett. 2013, 15, 2327-2329.
299. Fu, P.; Kong, F.; Li, X.; Wang, Y.; Zhu, W. Cyanogramide with a New Spiro[indolinonepyrroloimidazole] Skeleton from Actinoalloteichus cyanogriseus. Org. Lett. 2014, 16, 3708-3711.
300. Liu, Y.; Li, X.-M.; Meng, L.-H.; Wang, B.-G. N-Formyllapatin A, a new N-formylspiroquinazoline derivative from the marine-derived fungus Penicillium adametzioides AS-53. Phytochem. Lett. 2014, 10, 145-148.
301. Lee, C.; Sohn, J.H.; Jang, J.-H.; Ahn, J.S.; Oh, H.; Baltrusaitis, J.; Hwang, I.H.; Gloer, J.B. Cycloexpansamines A and B: Spiroindolinone alkaloids from a marine isolate of Penicillium sp. (SF-5292). J. Antibiot. 2015, doi:10.1038/ja.2015.56.
302. Choi, E.J.; Park, J.S.; Kim, Y.J.; Jung, J.H.; Lee, J.K.; Kwon, H.C.; Yang, H.O. Apoptosis-inducing effect of diketopiperazine disulfides produced by Aspergillus sp. KMD 901 isolated from marine sediment on HCT116 colon cancer cell lines. J. Appl. Microbiol. 2011, 110, 304-313.
303. Li, X.; Kim, S.-K.; Nam, K.W.; Kang, J.S.; Choi, H.D.; Son, B.W. A New Antibacterial Dioxopiperazine Alkaloid Related to Gliotoxin from a Marine Isolate of the Fungus Pseudallescheria. J. Antibiot. 2006, 59, 248-250.
304. Sun, Y.; Takada, K.; Takemoto, Y.; Yoshida, M.; Nogi, Y.; Okada, S.; Matsunaga, S. Gliotoxin Analogues from a Marine-Derived Fungus, Penicillium sp., and Their Cytotoxic and Histone Methyltransferase Inhibitory Activities. J. Nat. Prod. 2012, 75, 111-114.
305. Kong, F.; Wang, Y.; Liu, P.; Dong, T.; Zhu, W. Thiodiketopiperazines from the Marine-Derived Fungus Phoma sp. OUCMDZ-1847. J. Nat. Prod. 2014, 77, 132-137.
306. Cao, R.; Peng, W.; Wang, Z.; Xu, A. β-Carboline Alkaloids: Biochemical and Pharmacological Functions. Curr. Med. Chem. 2007, 14, 479-500.
307. Charan, R.D.; McKee, T.C.; Gustafson, K.R.; Pannell, L.K.; Boyd, M.R. Thorectandramine, a novel β-carboline alkaloid from the marine sponge Thorectandra sp. Tetrahedron Lett. 2002, 43, 5201-5204.
308. Segraves, N.L.; Lopez, S.; Johnson, T.A.; Said, S.A.; Fu, X.; Schmitz, F.J.; Pietraszkiewicz, H.; Valeriote, F.A.; Crews, P. Structures and cytotoxicities of fascaplysin and related alkaloids from two marine phyla-Fascaplysinopsis sponges and Didemnum tunicates. Tetrahedron Lett. 2003, 44, 3471-3475.
309. Kuzmich, A.S.; Fedorov, S.N.; Shastina, V.V.; Shubina, L.K.; Radchenko, O.S.; Balaneva, N.N.; Zhidkov, M.E.; Park, J.-I.; Kwak, J.Y.; Stonik, V.A. The anticancer activity of 3- and 10-bromofascaplysins is mediated by caspase-8, -9, -3-dependent apoptosis. Bioorg. Med. Chem. 2010, 18, 3834-3840.
310. Charan, R.D.; McKee, T.C.; Boyd, M.R. Cytotoxic Alkaloids from the Marine Sponge Thorectandra sp. Nat. Prod. Res. 2004, 18, 225-229.
311. Segraves, N.L.; Robinson, S.J.; Garcia, D.; Said, S.A.; Fu, X.; Schmitz, F.J.; Pietraszkiewicz, H.; Valeriote, F.A.; Crews, P. Comparison of Fascaplysin and Related Alkaloids: A Study of Structures, Cytotoxicities, and Sources. J. Nat. Prod. 2004, 67, 783-792.
312. Ravinder, K.; Vijender Reddy, A.; Krishnaiah, P.; Ramesh, P.; Ramakrishna, S.; Laatsch, H.; Venkateswarlu, Y. Isolation and synthesis of a novel β-carboline guanidine derivative tiruchanduramine from the Indian ascidian Synoicum macroglossum. Tetrahedron Lett. 2005, 46, 5475-5478.
313. Peng, J.; Hu, J.-F.; Kazi, A.B.; Li, Z.; Avery, M.; Peraud, O.; Hill, R.T.; Franzblau, S.G.; Zhang, F.; Schinazi, R.F.; 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, 13382-13386.
314. Yousaf, M.; Hammond, N.L.; Peng, J.; Wahyuono, S.; McIntosh, K.A.; Charman, W.N.; Mayer, A.M.S.; Hamann, M.T. 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, 3512-3517.
315. Rao, K.V.; Kasanah, N.; Wahyuono, S.; Tekwani, B.L.; Schinazi, R.F.; Hamann, M.T. Three New Manzamine Alkaloids from a Common Indonesian Sponge and Their Activity against Infectious and Tropical Parasitic Diseases. J. Nat. Prod. 2004, 67, 1314-1318.
316. Rao, K.V.; Donia, M.S.; Peng, J.; Garcia-Palomero, E.; Alonso, D.; Martinez, A.; Medina, M.; Franzblau, S.G.; Tekwani, B.L.; Khan, S.I.; et al. Manzamine B and E and Ircinal A Related Alkaloids from an Indonesian Acanthostrongylophora Sponge and Their Activity against Infectious, Tropical Parasitic, and Alzheimer's Diseases. J. Nat. Prod. 2006, 69, 1034-1040.
317. Takahashi, Y.; Kubota, T.; Fromont, J.; Kobayashi, J.I. Zamamidines A and B, New Manzamine Alkaloids from the Sponge Amphimedon Species. Org. Lett. 2009, 11, 21-24.
318. Yamada, M.; Takahashi, Y.; Kubota, T.; Fromont, J.; Ishiyama, A.; Otoguro, K.; Yamada, H.; Omura, S.; Kobayashi, J.I. Zamamidine C, 3, 4-dihydro-6-hydroxy-10, 11-epoxymanzamine A, and 3, 4-dihydromanzamine J N-oxide, new manzamine alkaloids from sponge Amphimedon sp. Tetrahedron 2009, 65, 2313-2317; Corrigendum in 2009, 65, 6263.
319. Wahba, A.E.; Fromentin, Y.; Zou, Y.; Hamann, M.T. Acantholactone, a new manzamine related alkaloid with an unprecedented δ-lactone and ε-lactam ring system. Tetrahedron Lett. 2012, 53, 6329-6331.
320. El-Desoky, A.H.; Kato, H.; Eguchi, K.; Kawabata, T.; Fujiwara, Y.; Losung, F.; Mangindaan, R.E.P.; de Voogd, N.J.; Takeya, M.; Yokosawa, H.; et al. Acantholactam and Pre-neo-kauluamine, Manzamine-Related Alkaloids from the Indonesian Marine Sponge Acanthostrongylophora ingens. J. Nat. Prod. 2014, 77, 1536-1540.
321. Furusato, A.; Kato, H.; Nehira, T.; Eguchi, K.; Kawabata, T.; Fujiwara, Y.; Losung, F.; Mangindaan, R.E.P.; de Voogd, N.J.; Takeya, M.; et al. Acanthomanzamines A-E with New Manzamine Frameworks from the Marine Sponge Acanthostrongylophora ingens. Org. Lett. 2014, 16, 3888-3891.
322. Pedpradab, S.; Edrada, R.; Ebel, R.; Wray, V.; Proksch, P. New β-Carboline Alkaloids from the Andaman Sea Sponge Dragmacidon sp. J. Nat. Prod. 2004, 67, 2113-2116.
323. Iinuma, Y.; Kozawa, S.; Ishiyama, H.; Tsuda, M.; Fukushi, E.; Kawabata, J.; Fromont, J.; Kobayashi, J.I. Gesashidine A, a β-Carboline Alkaloid with an Imidazole Ring from a Thorectidae Sponge. J. Nat. Prod. 2005, 68, 1109-1110.
324. Ibrahim, S.R.M.; Ebel, R.; Ebel, R.; Proksch, P. Acanthomine A, a new pyrimidine-β-carboline alkaloid from the sponge Acanthostrongylophora ingens. Nat. Prod. Commun. 2008, 3, 175-178.
325. Till, M.; Prinsep, M.R. 5-Bromo-8-methoxy-1-methyl-β-carboline, an Alkaloid from the New Zealand Marine Bryozoan Pterocella vesiculosa. J. Nat. Prod. 2009, 72, 796-798.
326. Wang, W.; Nam, S.-J.; Lee, B.-C.; Kang, H. β-Carboline Alkaloids from a Korean Tunicate Eudistoma sp. J. Nat. Prod. 2008, 71, 163-166.
327. Takahashi, Y.; Ishiyama, H.; Kubota, T.; Kobayashi, J.I. Eudistomidin G, a new β-carboline alkaloid from the Okinawan marine tunicate Eudistoma glaucus and structure revision of eudistomidin B. Bioorg. Med. Chem. Lett. 2010, 20, 4100-4103.
328. Suzuki, T.; Kubota, T.; Kobayashi, J.I. Eudistomidins H-K, new β-carboline alkaloids from the Okinawan marine tunicate Eudistoma glaucus. Bioorg. Med. Chem. Lett. 2011, 21, 4220-4223.
329. Kearns, P.S.; Rideout, J.A. Nonsymmetrical β-Carboline Dimers from an Ascidian, Didemnum sp. J. Nat. Prod. 2008, 71, 1280-1282.
330. Lee, H.-S.; Yoon, K.-M.; Han, Y.-R.; Lee, K.J.; Chung, S.-C.; Kim, T.-I.; Lee, S.-H.; Shin, J.; Oh, K.-B. 5-Hydroxyindole-type alkaloids, as Candida albicans isocitrate lyase inhibitors, from the tropical sponge Hyrtios sp. Bioorg. Med. Chem. Lett. 2009, 19, 1051-1053.
331. Youssef, D.; Shaala, L.; Asfour, H. Bioactive Compounds from the Red Sea Marine Sponge Hyrtios Species. Mar. Drugs 2013, 11, 1061-1070.
332. Inman, W.D.; Bray, W.M.; Gassner, N.C.; Lokey, R.S.; Tenney, K.; Shen, Y.Y.; TenDyke, K.; Suh, T.; Crews, P. A β-Carboline Alkaloid from the Papua New Guinea Marine Sponge Hyrtios reticulatus. J. Nat. Prod. 2010, 73, 255-257.
333. Khokhar, S.; Feng, Y.; Campitelli, M.R.; Ekins, M.G.; Hooper, J.N.A.; Beattie, K.D.; Sadowski, M.C.; Nelson, C.C.; Davis, R.A. Isolation, structure determination and cytotoxicity studies of tryptophan alkaloids from an Australian marine sponge Hyrtios sp. Bioorg. Med. Chem. Lett. 2014, 24, 3329-3332.
334. Ren, S.; Ma, W.; Xu, T.; Lin, X.; Yin, H.; Yang, B.; Zhou, X.-F.; Yang, X.-W.; Long, L.; Lee, K.J.; et al. Two novel alkaloids from the South China Sea marine sponge Dysidea sp. J. Antibiot. 2010, 63, 699-701.
335. Qi, S.-H.; Miao, L.; Gao, C.-H.; Xu, Y.; Zhang, S.; Qian, P.-Y. New Steroids and a New Alkaloid from the Gorgonian Isis minorbrachyblasta: Structures, Cytotoxicity, and Antilarval Activity. Helvetica Chimica Acta 2010, 93, 511-516.
336. Davis, R.A.; Duffy, S.; Avery, V.M.; Camp, D.; Hooper, J.N.A.; Quinn, R.J. (+)-7-Bromotrypargine: An antimalarial β-carboline from the Australian marine sponge Ancorina sp. Tetrahedron Lett. 2010, 51, 583-585.
337. Chan, S.T.S.; Pearce, A.N.; Page, M.J.; Kaiser, M.; Copp, B.R. Antimalarial β-Carbolines from the New Zealand Ascidian Pseudodistoma opacum. J. Nat. Prod. 2011, 74, 1972-1979.
338. Savi, D.; Shaaban, K.; Vargas, N.; Ponomareva, L.; Possiede, Y.; Thorson, J.; Glienke, C.; Rohr, J. Microbispora sp. LGMB259 Endophytic Actinomycete Isolated from Vochysia divergens (Pantanal, Brazil) Producing β-Carbolines and Indoles with Biological Activity. Curr. Microbiol. 2015, 70, 345-354.