Cyclodepsipeptides: A rich source of biologically active compounds for drug research

Molecules

Volumn 19, Issue 8, 2014, Pages 12368-12420

  Sivanathan, Sivatharushan ^a   Scherkenbeck, Jürgen ^a  

^a UNIVERSITY OF WUPPERTAL   (Germany)

Author keywords

Biological activity; Cyclodepsipeptide; Natural product; Solid phase synthesis; Total synthesis

Indexed keywords

ANTHELMINTIC AGENT; ANTIINFECTIVE AGENT; DEPSIPEPTIDE; FUNGICIDE; IMMUNOLOGIC FACTOR;

ANIMAL; HUMAN; MICROBIAL SENSITIVITY TEST; SYNTHESIS;

ANIMALS; ANTHELMINTICS; ANTI-BACTERIAL AGENTS; DEPSIPEPTIDES; FUNGICIDES, INDUSTRIAL; HUMANS; IMMUNOLOGIC FACTORS; MICROBIAL SENSITIVITY TESTS;

EID: 84906696500     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules190812368     Document Type: Review

References (137)

1. Dory, Y.L.; Mellor, J.M. Improved methods of synthesis of valinomycins. Tetrahedron Lett. 1989, 30, 1695-1698.
2. Hinaje, M.; Ford, M.; Banting, L.; Arkle, S.; Khambay, B. An investigation of the ionophoric characteristics of destruxin A. Arch. Biochem. 2002, 405, 73-77.
3. Davies, J.S. The cyclization of peptides and depsipeptides. J. Pept. Sci. 2003, 9, 471-501.
4. Davidson, B.S. Ascidians: procedure of amino acid-derived metabolites. Chem. Rev. 1993, 93, 1771-1791.
5. Moore, R.E. Cyclic peptides and depsipeptides from cyanobacteria: A review. J. Ind. Microbiol. 1996, 16, 134-143.
6. Kitir, B.; Baldry, M.; Ingmer, H.; Olsen, C.A. Total synthesis and structural validation of cyclodepsipeptides solonamide A and B. Tetrahedron 2014, in press.
7. Li, W.; Schlecker, A.; Ma, D. Total synthesis of antimicrobial and antitumor cyclic depsipeptides. Chem. Commun. 2010, 46, 5403-5420.
8. Lüttenberg, S.; Sondermann, F.; Scherkenbeck, J. A practical method for the generation of Kaiser-oxime resin. Tetrahedron Lett. 2013, 54, 907-908.
9. Stolze, S.C.; Kaiser, M. Case studies of the synthesis of bioactive cyclodepsipeptide natural products. Molecules 2013, 18, 1337-1367.
10. Humano, K.; Kinoshita, M.; Furuya, K.; Miyamoto, M.; Takamatsu, Y.; Hemmi, A.; Tanzawa, K. Leualacin, a novel calcium blocker from Hapsidospora irregularis. J. Antibiot. 1991, 45, 899-905.
11. Kikuchi, M.; Nosaka, K.; Akaji, K.; Konno, H. Solid phase total synthesis of callipeltin E isolated from marine sponge Latrunculia sp. Tetrahedron Lett. 2011, 52, 3872-3875.
12. Zhou, X.; Huang, H.; Li, J.; Song, Y.; Jiang, R.; Liu, J.; Zhang, S.; Hua, Y.; Ju, J. New anti-infective cycloheptadepsipeptide congeners and absolute stereochemistry from the deep sea-derived Streptomyces drozdowiczii SCIO 10141. Tetrahedron 2014, in press.
13. Finking, R.; Marahiel, M.A. Biosynthesis of nonribosomal peptides. Annu. Rev. Microbiol. 2004, 58, 453-488.
14. Gao, X.; Haynes, S.W.; Ames, B.D.; Wang, P.; Vien, L.P.; Walsh, C.T.; Tang, Y. Cyclization of fungal nonribosomal peptides by a terminal condensation-like domain. Nat. Chem. Biol. 2012, 8, 823-830.
15. Kopp, F.; Mahlert, C.; Grünewald, J.; Marahiel, M.A. Peptide macrocyclization: the reductase of the nostocyclopeptide synthetase triggers the self-assembly of a macrocyclic imine. J. Am. Chem. Soc. 2006, 128, 16478-16479.
16. Xu, Y.; Orozo, R.; Wijeratne, E.M.K.; Gunatilaka, A.A.L.; Stock, S.P.; Molnar, I. Biosynthesis of the cyclooligomer depsipeptide beauvericin, a virulence factor of the entomopathogenic fungus Beauveria bassiana. Chem. Biol. 2008, 15, 898-907.
17. Yu, D.; Xu, F.; Zi, J.; Wang, S.; Gage, D.; Zeng, J.; Zhan, J. Engineered production of fungal anticancer cyclooligomer depsipeptides in Saccharomyces cerevisae. Metab. Eng. 2013, 18, 60-68.
18. Süssmuth, R.; Müller, J.; von Döhren, H.; Molnar, I. Fungal cyclooligomer depsipeptides: From classical biochemistry to combinatorial biosynthesis. Nat. Prod. Rep. 2011, 28, 99-124.
19. 2 evolution in apple leaves. Biosci. Biotechnol. Biochem. 2003, 67, 635-638.
20. Lee, S.; Aoyagi, H.; Shimohigashi, Y.; Izumiya, N. Synthesis of cyclotetradepsipeptides, AM-toxin I and its analogs. Tetrahedon Lett. 1976, 11, 843-846.
21. Shimohigashi, Y.; Lee, S.; Kato, T.; Izumiya N.; Ueno, T.; Fukami, H. Synthesis and necrotic activity of dihydro-AM-toxin I. Agric. Biol. Chem. 1977, 8, 1533-1534.
22. Ueda, K.; Waki, M.; Teruya, Y.; Izumiya, N. Facile synthesis of AM-toxin II. Bull. Chem. Soc. Jpn. 1989, 62, 1635-1638.
23. Hashimoto, K.; Sakai, M.; Okuno, T.; Shirahama, H. β- Phenylselenoalanine as a dehydroalanine precursor-efficient synthesis of alternariolide (AM-toxin I). Chem. Commun. 1996, 1139-1140.
24. Miyashita, M.; Nakamori, T.; Murai, T.; Miyagawa, H.; Akamatsu, M.; Ueno, T. Facile synthesis of AM-toxins and analogs as cyclic depsipeptides by the solid-phase method. Biosci. Biotechnol. Biochem. 1998, 9, 1799-1801.
25. Horikawa, E.; Kodaka, M.; Nakahara, Y.; Okuno, H.; Nakamura, K. Solid-phase synthesis of dehydropeptide, AM-toxin II, using a novel selenyl linker by side-chain tethered strategy. Tetrahedon Lett. 2001, 42, 8337-8339.
26. Konzono, T.; Kanmera, T.; Kato, T.; Ueno, T.; Izumiya, N. Synthesis of lactam analog of AM-toxin I. Agric. Biol. Chem. 1983, 47, 2631-2632.
27. Kunicki, J.B.; Peterson, M.N.; Alexander, L.D.; Ardi, V.C.; McConnell, J.R.; McAlpine S.R. Synthesis and evaluation of biotinylated sansalvamide A analogs and their modulation of Hsp90. Bioorg. Med. Chem. Lett. 2011, 21, 4716-4719.
28. Belofsky, G.N.; Jensen, P.R.; Fenical, W. Sansalvamide: A new cytotoxic cyclic depsipeptide produced by a marine fungus of the genus Fusarium. Tetrahedron Lett. 1999, 40, 2913-2916.
29. Cueto, M.; Jensen, P.R.; Fenical, W. N-methylsansalvamide, a cytotoxic cyclic depsipeptide from a marine fungus of the genus Fusarium. Phytochemistry 2000, 55, 223-226.
30. Song, H.; Lee, H.; Lee, C. A new cytotoxic cyclic pentadepsipeptide, neo-N-methylsansalvamide produced by Fusarium solani KCCM90040, isolated from potato. Food Chem. 2011, 126, 472-478.
31. Lee, Y.; Silverman, R.B. Rapid, high-yield, solid-phase synthesis of the antitumor antibiotic sansalvamide A using a side-chain-tethered phenylalanine building block. Org. Lett. 2000, 2, 3743-3746.
32. Gu, W.; Liu, S.; Silverman, R.B. Solid-phase, Pd-catalyzed silicon-aryl carbon bond formation. Synthesis of sansalvamide A peptide. Org. Lett. 2002, 4, 4171-4174.
33. Carroll, C.L.; Johnston, J.V.C.; Kekec, A.; Brown, J.D.; Parry, E.P.; Cajica, J.; Medina, I.; Cook, K.M.; Corral, R.; Pan, P.; et al. Synthesis and cytotoxicity of novel sansalvamide A derivatives. Org. Lett. 2005, 7, 3481-3484.
34. Liu, S.; Gu, W.; Lo, D.; Ding, X.Z.; Ujiki, M.; Adrian, T.E.; Stoff, G.A.; Silverman, R.B. N-Methylsansalvamide A peptide analogs. Potent antitumor agents. J. Med. Chem. 2005, 48, 3630-3638.
35. Davis, M.R.; Styers, T.J.; Rodriguez, R.A.; Pan, P.; Vasko, R.C.; McAlpine, S.R. Synthesis and cytotoxicity of a new class of potent decapeptide macrocycles. Org. Lett. 2008, 10, 177-180.
36. Alexander, L.D.; Sellers, R.P.; Davis, M.R.; Ardi, V.C.; Johnson, V.A.; Vasko, R.C.; MaAlpine, S.R. Evaluation of di-sansalvamide A derivatives: Synthesis, structure-activity relationship, and mechanism of action. J. Med. Chem. 2009, 52, 7927-7930.
37. Davis, M.R.; Singh, E.K.; Wahyudi, H.; Alexander, L.D.; Kunicki, J.B.; Nazarova, L.A.; Fairweather, K.A.; Giltrap, A.M.; Jolliffe, K.A.; Mc Alpine, S.R. Synthesis of sansalvamide A peptidomimetics: Triazole, oxazole, thiazole and pseudoproline containing compounds. Tetrahedron 2012, 68, 1029-1051.
38. Ramsey, D.M.; McConnel, J.R.; Alexander, L.D.; Tanaka, K.W.; Vera, C.M.; McAlpine, S.R. An Hsp90 modulator that exhibits a unique mechanistic profile. Bioorg. Med. Chem. Lett. 2012, 22, 3287-3290.
39. Liu, S.; Yang, Y.; Zhao, C.; Huang, J.; Han, C.; Han, J. Effect of the 4'-substituted phenylalanine moiety of sansalvamide A peptide on antitumor activity. Med. Chem. Commun. 2014, 5, 463-467.
40. Kim, M.; Sohn, J.; Ahn, J.; Oh, H. Alternaramide, a cyclic depsipeptide from the marine-derived fungus Alternaria sp. SF-5016. J. Nat. Prod. 2009, 72, 2065-2068.
41. Horton, A.E.; May, O.S.; Elsegood, M.R.J.; Kimber, M.C. Total synthesis of the marine-derived cyclic depsipeptide alternaramide. Synlett 2011, 22, 797-800.
42. Oh, D.; Jensen, P.R.; Fenical, W. Zygosporamide, a cytotoxic cyclic depsipeptide from the marine-derived fungus Zygosporium masonii. Tetrahedron Lett. 2006, 47, 8625-8628.
43. Wang, Y.; Zhang, F.; Zhang, Y.; Liu, J.O.; Ma, D. Synthesis and antitumor activity of cyclodepsipeptide zygosporamide and its analogues. Bioorg. Med. Chem. Lett. 2008, 18, 4385-4387.
44. Sy-Cordero, A.A.; Pearce, C.J.; Oberlies, N.H. Revisting the enniatins: A review of their isolation, biosynthesis, structure determination, and biological activities. J. Antibiot. 2012, 65, 541-549.
45. Krause, M.; Lindemann, A.; Glinski, M.; Hornbogen, T.; Bonse, G.; Jeschke, P.; Thielking, G.; Gau, W.; Kleinkauf, H.; Zocher, R. Directed biosynthesis of new enniatins. J. Antibiot. 2001, 54, 797-804.
46. Pieper, R.; Kleinkauf, H.; Zocher, R. Enniatin synthetases from different fusaria exhibiting distinct amino acid specificities. J. Antibiot. 1992, 45, 1273-1277.
47. Zhan, J.; Burns, A.M.; Liu, M.X.; Faeth, S.H.; Gunatilaka, A.A.L. Search for cell motility and angiogenesis inhibitors with potential anticancer activity: Beauvericin and other constitutions of two endophytic strains of Fusarium oxysporum. J. Nat. Prod. 2007, 70, 227-232.
48. Wu, X.; Xu R.; Ouyang, Z.; Qian, C.; Shen, Y.; Wu, X.; Gu, Y.; Xu, Q.; Sun, Y. Beauvericin ameliorates experimental colitis by inhibiting activated T cells via downregulation of the PI3K/Akt signaling pathway. PLoS One 2013, 8, 1-11.
49. Shemyakin, M.M.; Ovchinnikov, Y.A.; Kiryushkin, A.A.; Ivanov, V.T. The structure and total synthesis of enniatin B. Tetrahedron Lett. 1963, 14, 885-890.
50. Hu, D.X.; Bielitza, M.; Koos, P.; Ley, V.S. A total synthesis of the ammonium ionophore, (-)-enniatin B. Tetrahedron Lett. 2012, 53, 4077-4079.
51. Jeschke, P.; Benet-Buchholz, J.; Harder, A.; Etzel, W.; Schindler, M.; Gau, W.; Weiss, H. Synthesis and anthelmintic activity of substituted (R)-phenyllactic acid containing cyclohexadepsipeptides. Bioorg. Med. Chem. Lett. 2006, 16, 4410-4415.
52. Jeschke, P.; Harder, A.; Etzel, W.; Schindler, M.; Thielking, G. Synthesis and anthelmintic activity of cyclohexadepsipeptides with cyclohexylmethyl side chains. Bioorg. Med. Chem. Lett. 2007, 17, 3690-3695.
53. Glinski, M.; Urbanke, C.; Hornbogen, T.; Zocher, R. Enniatin synthetase is a monomer with extended structure: evidence for an intermolecular mechanism. Arch. Microbiol. 2002, 178, 267-273.
54. Madry, N.; Zocher, R.; Grodzki, K.; Kleinkauf, H. Selective synthesis of depsipeptides by the immobilized multienzyme enniatin synthetase. Appl. Microbiol. Biotechnol. 1984, 20, 83-86.
55. Feifel, S.C.; Schmiederer, T.; Hornbogen, T.; Berg, H.; Süssmuth, R.D.; Zocher R. In vitro synthesis of new enniatins: Probing the α-hydroxy carboxylic acid binding pocket of the multienzyme enniatin synthetase. ChemBioChem 2007, 8, 1767-1770.
56. Peeters, H.; Zocher, R.; Kleinkauf, H. Synthesis of beauvericin by a multifunctional enzyme. J. Antibiot. 1988, 41, 352-359.
57. Peeters, H.; Zocher, R.; Madry, N.; Oelrichs, P.B.; Kleinkauf, H.; Kraepelin, G. Cell-free synthesis of the depsipeptide beauvericin. J. Antibiot. 1983, 36, 1762-1766.
58. Xu, Y.; Zhan, J.; Wijeratne, E.M.K.; Burns, A.M.; Gunatilaka, A.A.L.; Molnar, I. Cytotoxic and antihaptotactic beauvericin analogues from precursor-directed biosynthesis with the insect pathogen Beauveria bassiana ATCC 7159. J. Nat. Prod. 2007, 70, 1467-1471.
59. Nilanonta, C.; Isaka, M.; Kittakoop, P.; Trakulnaleamsai, S.; Tanticharoen, M.; Thebtaranonth, Y. Precursor-directed biosynthesis of beauvericin analogs by the insect pathogenic fungus Paecilomyces tenuipes BCC 1614. Tetrahedron 2002, 58, 3355-3360.
60. Matthes, D.; Richter, L.; Müller, J.; Denisiuk, A.; Feifel, S.C.; Xu, Y.; Espinosa-Artiles, P.; Süssmuth, R.D.; Molnar, I. In vitro chemoenzymatic and in vivo biocatalytic synthesis of new beauvericin analogues. Chem. Commun. 2012, 48, 5674-5676.
61. Isaka, M.; Yangchum, A.; Sappan, M.; Suvannakad, R.; Srikitikulchai, P. Cyclohexadepsipeptides from Acremonium sp. BCC 28424. Tetrahedron 2011, 67, 7929-7935.
62. Bunyapaiboonsri, T.; Vongvilai, P.; Auncharoen, P.; Isaka, M. Cyclohexadepsipeptides from the filamentous fungus Acremonium sp. BCC 2629. Helv. Chim. Acta 2012, 95, 963-972.
63. Vongvanich, N.; Kittakoop, P.; Isaka, M.; Trakulnaleamsai, S.; Vimuttipong, S.; Tanticharoen, M.; Thebtaranonth, Y.; Hirsutellide A. a new antimycobacterial cyclohexadepsipeptide from the entomopathogenic fungus Hirsutella kobayasii. J. Nat. Prod. 2002, 65, 1346-1348.
64. Xu, Y.; Chen, L.; Duan, X.; Meng, Y.; Jiang, L.; Li, M.; Zhao, G.; Li, Y. Total synthesis of hirsutellide A. Tetrahedron Lett. 2005, 46, 4377-4379.
65. Xu, Y.; Duan, X.; Li, M.; Jian, L.; Zhao, G.; Meng, Y.; Chen, L. Synthesis of the key precursor of hirsutellide A. Molecules 2005, 10, 259-264.
66. Xu, Y.; Chen, L.; Ma, Y.; Li, J.; Cao, X. Silver-ion mediated macrocyclization to form cyclohexadepsipeptide. Synlett 2007, 12, 1901-1904.
67. Pohanka, A.; Menkis, A.; Levenfors, J.; Broberg, A. Low-abundance kutznerides from Kutznerica sp. 744. J. Nat. Prod. 2006, 69, 1776-1781.
68. Broberg, A.; Menkis, A.; Vasiliauskas, R. Kutznerides 1-4, depsipeptides from the actinomycete Kutzeria sp. 744 inhabiting mycorrhizal roots of Picea abies seedlings. J. Nat. Prod. 2006, 69, 97-102.
69. Fujimori, D.G.; Hrvatin, S.; Neumann, C.S.; Strieker, M.; Marahiel, M.A.; Walsh, C.T. Cloning and characterization of the biosynthetic gene cluster for kutnerides. PNAS 2007, 104, 16498-16503.
70. Bevan, K.; Davies, J.S.; Hall, M.J.; Hassal, C.H.; Morton, R.B.; Phillips, D.A.S.; Ogihira, Y.; Thomas, W.A. The monamycins, a new family of cyclodepsipeptide antibiotics. Experientia 1970, 26, 122-123.
71. Hall, M.J. Mode of action of monamycin. Evidence for the formation of a complex between the monamycin cyclodepsipeptide antibiotics and some cations in solution. Biochem. Biophys. Res. Commun. 1970, 38, 590-598.
72. Hale, K.J.; Jogiya, N.; Manaviazar, S. Monamycin synthetic studies. Pt 1. An enantiospecific total synthesis of (3S,5S)-5-hydroxypiperazic acid from D-Mannitol. Tetrahedron Lett. 1998, 39, 7163-7166.
73. Hall, M.J.; Handford, B.O.; Hassyl, C.H.; Phillips, D.A.S.; Rees, A.V. Bromomonamycins, unnatural analogues of the monamycin cyclodepsipeptide antibiotics: Production, isolation, and biological activity. Antimircob. Agents Chemother. 1973, 3, 380-383.
74. Lam, K.S.; Heslter, G.A.; Mattel, J.M.; Mamber, S.W.; Forenza, S. Himastatin, a new antitumor antibiotic from Streptomyces hygroscopius. I. Taxonomy of producing organism, fermentation and biological activity. J. Antibiot. 1990, 8, 956-960.
75. Left, J.E.; Schröder, D.R.; Krishan, B.S.; Matron, J.A. Himastatin, a new antitumor antibiotic from Streptomyces hygroscopicus. II. Isolation and characterization. J. Antibiot. 1990, 8, 961-966.
76. Left, J.E.; Schroeder, D.R.; Golik, J.; Matson, J.A.; Doyle, T.W.; Lam, K.S.; Hill, S.E.; Lee, M.S.; Whitney, J.L.; Krishnan, B.S. Himastatin, a new antitumor antibiotic from Streptomyces hygroscopicus. III. Structural elucidation. J. Antibiot. 1996, 49, 299-311.
77. Ruiz-Sanchis, R.; Savina, S.A.; Albericio, F.; Alvarez, M. Structure, bioactivity and synthesis of natural products with hexahydropyrrolo[2,3-b] indole. Chem. Eur. J. 2011, 17, 1388-1408.
78. Kamenecka, T.M.; Danishefsky, S.J. Discovery through total synthesis: A retrospective on the himastatin problem. Chem. Eur. J. 2001, 7, 41-63.
79. Kamenecka, T.M.; Danishefsky, S.J. Studies in the total synthesis of himastatin: A revision of the stereochemical assignment. Angew. Chem. Int. Ed. 1998, 37, 2993-2995.
80. Kamenecka, T.M.; Danishefsky, S.J. Total synthesis of himastatin: Confirmation of the revised stereostructure. Angew. Chem. Int. Ed. 1998, 37, 2995-2998.
81. Ma, J.; Wang, Z.; Huang, H.; Luo, M.; Zuo, D.; Wang, B.; Sun, A.; Cheng, Yi.; Zhang, C.; Ju, J. Biosynthesis of himastatin: assembly line and characterization of three cytrochrome P450 enzymes involved in the post-tailoring oxidative steps. Angew. Chem. Ind. Ed. 2011, 50, 7797-7802.
82. Isaka, M.; Palasarn, S.; Supothina, S.; Komwijit, S.; Luangsaard, J. Bioactive compounds from the scale insect pathogenic fungus Conoideocrella tenius BCC 18627. J. Nat. Prod. 2011, 74, 782-789.
83. Isaka, M.; Palasarn, S.; Lapanun, S.; Striklung, K. Peacilodepsipeptide A, an antimalarial and antitumor cyclohexadepsipeptide from the insect pathogenic fungus Peacilomyces cinnamomeus BCC 9616. J. Nat. Prod. 2007, 70, 675-678.
84. Yang, M.J.; Wu, J.; Yang, Z.D.; Zhang, Y.M. First total synthesis of peacilodepsipeptide A. Chin. Chem. Lett. 2009, 20, 527-530.
85. Isaka, M.; Berkaew, P.; Intereya, K.; Komwijit, S.; Sathitkunanon T. Antiplasmodial and antiviral cyclohexadepsipeptides from the endophytic fungus Pullularia sp. BCC 8613. Tetrahedron 2007, 63, 6855-6860.
86. Ebrahim, W.; Kjer, J.; El Amrani, M.; Wray, V.; Lin, W.; Ebel, R.; Lai, D.; Proksch, P. Pullularins E and F, two new peptides from the endophytic fungus Bionecteria ochroleuca isolated from the mangrove plant Sonneratia caseolaris. Mar. Drugs 2012, 10, 1081-1091.
87. Isaka, M.; Palasarn, S.; Sriklung, K.; Kocharin, K. Cyclohexadepsipeptides from the insect pathogenic fungus Hirsutella nivea BB 2594. J. Nat. Prod. 2005, 68, 1680-1682.
88. Isaka, M.; Rugseree, N.; Maithip, P.; Kongsaeree, P.; Prabpai, S.; Thebtaranonth, Y. Hirsutellones A-E, antimycobacterial alkaloids from the insect pathogenic fungus Hirsutella nivea BCC 2594. Tetrahedron 2005, 61, 5577-5583.
89. Chen, Y.; Bilban, M.; Foster, C.A.; Boger, D.L. Solution-phase parallel synthesis of a pharmacophore library of HUN-7293 analogues: A general chemical mutagenesis approach to defining structure-function properties of naturally occurring cyclic (depsi)peptides. J. Am. Chem. Soc. 2002, 124, 5431-5440.
90. Boger, D.L.; Keim, H.; Oberhauser, B.; Schreiner, E.P.; Foster, C.A. Total synthesis of HUN-7293. J. Am. Chem. Soc. 1999, 121, 6197-6205.
91. Boger, D.L.; Chen, Y.; Foster, C.A. Synthesis and evaluation of aza HUN-7293. Bioorg. Med. Chem. Lett. 2000, 10, 1741-1744.
92. Schreiner, E.P.; Kern, M.; Steck, A. A convenient protocol for selective cleavage of 2-hydroxy acid amides. Application to semisynthesis of the cyclic heptapeptide aza HUN-7293. J. Org. Chem. 2002, 67, 8299-8304.
93. Kanaoka, M.; Isogai, A.; Murakoshi, S.; Ichinoe, M.; Suzuki, A.; Tamura, S. Bassianolide, a new insecticidal cyclodepsipeptide from Beauveria bassiana and Verticillium lecanii. Agric. Biol. Chem. 1978, 42, 629-635.
94. Nakajyo, S.; Shimizu, K.; Kometani, A.; Suzuki, A.; Ozaki, H.; Urakawa, N. On the inhibitory mechanism of bassianolide, a cyclodepsipeptide, in acetylcholine-induced contraction in guinea-pig taenia coli. Jpn. J. Pharmacol. 1983, 33, 573-582.
95. Jirakkakul, J.; Punya, J.; Pongpattanakitshote, S.; Paungmoung, P.; Vorapreeda, N.; Tachaleat, A.; Klomnara, C.; Tanticharoen, M.; Cheevadhanarak, S. Identification of the nonribosomal peptide synthetase gene responsible for bassianolide synthesis in wood-decaying fungus Xylaria sp. BCC1067. Microbiology 2008, 154, 995-1006.
96. Kanaoka, M.; Isogai, A.; Suzuki, A. Synthesis of bassianolide. Tetrahedron Lett. 1977, 46, 4049-4050.
97. Shiomi, K.; Matsui, R.; Kakei, A.; Yamaguchi, Y.; Masuma, R.; Hatano, H.; Arai, N.; Isozaki, M.; Tanaka, H.; Kobayashi, S.; et al. Verticilide, a new ryanodine-binding inhibitor, produced by Verticilium sp. FKI-1033. J. Antibiot. 2010, 63, 77-82.
98. Ohshiro, T.; Matsudo, D.; Kazuhiro, T.; Uchida, R.; Nonaka, K.; Masuma, R.; Tomada, H. New verticilides, inhibitors of acyl-CoA: Cholesterol acyltransferase, produced by Verticillium sp. FKI-2679. J. Antibiot. 2012, 65, 255-262.
99. Monma, S.; Sunazuka, T.; Nagai, K.; Arai, T.; Shiomi, K.; Matsui, R.; Omura, S. Verticilide: Elucidation of absolute configuration and total synthesis. Org. Lett. 2006, 8, 5601-5604.
100. Sasaki, T.; Takagi, M.; Yaguchi, T.; Miyadoh, S.; Okada, T.; Koyama, M. A new anthelmintic cyclodepsipeptide, PF1022A. J. Antibiot. 1992, 45, 692-697.
101. Sakanaka, O.; Okada, Y.; Ohyama, M.; Matsumoto, M.; Takahashi, M.; Murai, Y.; Iinuma, K.; Harder, A.; Mencke, N. Novel Cyclic Depsipeptide PF1022A Derivatives. Patent WO97/11064, 1997.
102. Dutton, F.E.; Nelson, S.J. Synthesis of PF1022A, an anthelmintic cyclodepsipeptide. J. Antibiot. 1994, 47, 1322-1327.
103. Ohyama, M.; Iinuma, K.; Isogai, A.; Suzuki, A. Total synthesis of the anthelmintic cyclodepsipeptide, PF1022A. Biosci. Biotechnol. Biochem. 1994, 58, 1193-1194.
104. Scherkenbeck, J.; Plant, A.; Harder, A.; Mencke, N. A highly efficient synthesis of the anthelmintic cyclooctadepsipeptide PF1022A. Tetrahedron 1995, 51, 8459-8470.
105. Kobayashi, M.; Nanba, T.; Toyama, T.; Saito, A. Synthesis and anthelmintic activity of the cyclodepsipeptide PF1022A. Annu. Rep. Sankyo Res. Lab. 1994, 46, 67-75.
106. Lee, B.H. Solid-phase synthesis of cyclooctadepsipeptide PF1022A analogs using a cyclization-cleavage method with oxime-resin. Tetrahedron Lett. 1997, 38, 757-760.
107. Nishino, N.; Xu, M.; Mihara, H.; Fujimoto, T. Sequence dependent cyclization-cleavage of dipeptides from the oxime resin and its prevention. Bull. Chem. Soc. Jpn. 1991, 65, 991-994.
108. Kumagai, H.; Efficient preparation of cyclic peptide mixtures by solid phase synthesis and cyclization cleavage with oxime resin. Tetrahedron Lett. 1995, 36, 4837-4840.
109. Dutton, F.E.; Lee, B.H. Epsilon-lactam analogs of the anthelmintic cyclodepsipeptide PF1022A. Tetrahedron Lett. 1998, 39, 5313-5316.
110. Lee, B.H.; Dutton, F.E.; Thompson, D.P.; Thomas, E.M. Generation of a small library of cyclodepsipeptides PF1022A analogues using a cyclization-cleavage method with oxime resin. Bioorg. Med. Chem. Lett. 2002, 12, 353-356.
111. Lüttenberg, S.; Sondermann, F.; Scherkenbeck, J. Anthelmintic PF1022A: Stepwise solid-phase synthesis of a cyclodepsipeptide containing N-methyl amino acids. Tetrahedron 2012, 68, 2068-2073.
112. Scherkenbeck, J.; Lüttenberg, S.; Ludwig, M.; Brüchner, K.; Kotthaus, A. Segment solid-phase total synthesis of the anthelmintic cyclooctadepsipeptides PF1022A and emodepside. Eur. J. Org. Chem. 2012, 1546-1553.
113. Scherkenbeck, J.; Jeschke, P.; Harder, A. PF1022A and related cyclodepsipeptides - A novel class of anthelmintics. Curr. Top. Med. Chem. 2002, 2, 759-777.
114. Scherkenbeck, J.; Dyker, H.; Gondol, D.; Harder, A.; Plant, A.; Reichel, F. Synthesis, conformational studies and anthelmintic activity of a constrained PF1022A analogue. Pest. Sci. 1999, 55, 457-461.
115. Dyker, H.; Harder, A.; Scherkenbeck, J. Chimeric cyclodepsipeptides as mimetics for the anthelmintic PF1022A. Bioorg. Med. Chem. Lett. 2004, 14, 6129-6132.
116. Dutton, F.E.; Lee, B.H.; Johnson, S.S.; Coscarelli, E.M.; Lee, P.H. Restricted conformation analogues of an anthelmintic cyclodepsipeptide. J. Med. Chem. 2003, 46, 2057-2073.
117. Dyker, H.; Scherkenbeck, J.; Gondol, D.; Goehrt, A.; Harder, A. Azadepsipeptides: Synthesis and evaluation of a novel class of peptidomimetics. J. Org. Chem. 2001, 66, 3760-3766.
118. Ohyama, M.; Okada, Y.; Takahashi, M.; Sakanaka, O.; Matsumoto, M.; Atsumi, K. Structure-activity relationship of anthelmintic cyclooctadepsipeptides. Biosci. Biotechnol. Biochem. 2011, 75, 1354-1363.
119. Ohyama, M. Chemistry of anthelmintic cyclodepsipeptides. Sci. Report of Meiji Seika Kaisha 2006, 45, 8-34.
120. Dyker, H.; Harder, A.; Mencke, N.; Scherkenbeck, J.; Georg von, S. Desoxycyclodepsipeptides and Their Use for Combatting Endoparasites. Patent WO19980554469A1, 1998.
121. Jeschke, P.; Harder, A.; Etzel, W.; Gau, W.; Thielking, G.; Bonse, G.; Iinuma, K. Synthesis and anthelmintic activity of thioamide analogues of cyclic octadepsipeptides such as PF1022A. Pest. Manag. Sci. 2001, 57, 1000-1006.
122. Jeschke, P.; Harder, A.; Samson-Himmelstjerna, G.V.; Etzel, W.; Gau, W.; Thielking, G.; Bonse, G. Synthesis of anthelmintically active N-methylated amidoxime analogues of the cyclic octadepsipeptide PF1022A. Pest. Manag. Sci. 2002, 58, 1205-1215.
123. Weckwerth, W.; Miyamoto, K.; Iinuma, K.; Krause, M.; Glinski, M.; Storm, T.; Bonse, G.; Kleinkauf, H.; Zocher, R. Biosynthesis of PF1022A and related cyclooctadepsipeptides. J. Biol. Chem. 2000, 275, 17909-17915.
124. Müller, J.; Feifel, S.C.; Schmiederer, T.; Zocher, R.; Süssmuth, R.D. In vitro synthesis of new cyclodepsipeptides of the PF1022A-type: Probing the α-D-hydroxy acid tolerance of PF1022 synthetase. ChemBioChem 2009, 10, 323-328.
125. Harder, A.; Schmitt-Wrede, H.; Krücken, J.; Marinovski, P.; Wunderlich, F.; Willson, J.; Amliwala, K.; Holden-Dye, L.; Walker, R. Cyclooctadepsipeptides - An anthelmintically active class of compounds exhibiting a novel mode of action. Int. J. Antimicrob. Ag. 2003, 22, 318-331.
126. Guest, M.; Bull, K.; Walker, R.J.; Amliwala, K.; O'Connor, V.; Harder, A.; Holden-Dye, L.; Hopper, A.N. The calcium-activated potassium channel, SLO-1, is required for the action of the novel cyclo-octadepsipeptide anthelmintic, emodepside, in Caenorhabditis elegans. Int. J. Parasitol. 2007, 37, 1577-1588.
127. Ueda, K.; Xiao, J.; Doke, N.; Nakatsuka, S. Isolation and structure of BZR-cotoxin IV produced by Bipolaris zeicola race 3, the cause of leaf spot disease in corn. Tetrahedron Lett. 1995, 36, 741-744.
128. Ueda, K.; Xiao, J.; Doke, N.; Nakatsuka, S. Structure of BZR-cotoxin I produced by Bipolaris zeicola race 3, the cause of leaf spot disease in corn. Tetrahedron Lett. 1994, 35, 7033-7036.
129. Ueda, K.; Xiao, J.; Doke, N.; Nakatsuka, S. Structure of BZR-cotoxin II produced by Bipolaris zeicola race 3, the cause of leaf spot disease in corn. Tetrahedron Lett. 1994, 33, 5377-5380.
130. Ueda, K.; Xiao, J.; Doke, N.; Nakatsuka, S. Structure of BZR-cotoxin III produced by Bipolaris zeicola race 3, the cause of leaf spot desease in corn. Nat. Prod. Lett. 1994, 6, 43-48.
131. Ikai, K.; Shiomi, K.; Takesako, K.; Mizutani, S.; Yamamoto, J.; Ogawa, Y.; Ueno, M.; Kato, I. Structures of aureobasidins B to R. J. Antibiot. 1991, 44, 1187-1198.
132. Yoshikawa, Y.; Ikai, K.; Umeda, Y.; Ogawa, A.; Takesako, K.; Kato, I. Isolation, structures, and antifungal activities of new aureobasidins. J. Antibiot. 1993, 46, 1347-1354.
133. Kurome, T.; Inami, K.; Inoue, T.; Ikai, K.; Takesako, K.; Kato, I.; Shiba, T. Total synthesis of an antifungal cyclic depsipeptide aureobasidin A. Tetrahedron 1996, 52, 4327-4346.
134. Jao, E.; Cooper, A.B.; Rane, D.F.; Saksena, A.K.; Desai, J.; Wang, J.; Girijavallabhan, V.M.; Ganguly, A.K. Total synthesis of the antifungal cyclic depsipeptides sch 57697 and aureobasidin A. Tetrahedron Lett. 1996, 37, 5661-5664.
135. Maharani, R.; Brownlee, R.T.C.; Hughes, A.B.; Abbott, B.M. A total synthesis of a highly N-methylated cyclodepsipeptide [2S,3S]-aureobasidin L using solid-phase methods. Tetrahedron 2014, 70, 2351-2358.
136. Suzuki, Y.; Ojika, M.; Sakagami, Y.; Kajda, K.; Fudou, R.; Kameyama, T. New cyclic depsipeptide antibiotics, clavariopsin A and B, produced by an aquatic hyphomycetes, Clavariopsis aquatica. 2. Structure analysis. J. Antibiot. 2001, 54, 22-28.
137. Kaika, K.; Fudou, R.; Kameyama, T.; Tubaki, K.; Suzuki, Y.; Ojika, M.; Sakagami, Y. New cyclic depsipeptide antibiotics, clavariopsins A and B, produced by an aquatic hyphomycetes, Clavariopsis aquatica. 1. Taxonomy, fermentation, isolation, and biological properties. J. Antibiot. 2001, 54, 17-21.