Naturally occurring anthracyclines

Topics in Current Chemistry

Volumn 282, Issue , 2008, Pages 3-74

  Laatsch, Hartmut ^a   Fotso, Serge ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Anthracyclines; Microbial metabolites; Natural products; Streptomycetes

Indexed keywords

EID: 84873693386     PISSN: 03401022     EISSN: None     Source Type: Book Series    
DOI: 10.1007/128-2008-5     Document Type: Review

References (283)

1. Brockmann H (1963) Anthracyclinone und Anthracycline. Fortschr Chem Org Naturst 21:121-182
2. FurlanRLA, Watt SJ, Garrido LM, AmaranteMGP, Nur-e-AlamM, Rohr J, BranaA, Mendez C, Salas JA, Sheil MM, Beck JL, Padilla G (2004) J Antibiot 57:647
3. Behal V (2000) Adv App Microbiol 47:113
4. Sasaki T, Tsukada Y, Deutsch HF, Hirai H (1984) Cancer Chemother Pharmacol 13:75
5. Yang JY, Luo HY, Lin QY, Liu ZM, Yan LN, Lin P, Zhang J, Lei S (2002) World J Gastroenterol 8:44
6. Gewirtz DA (1999) Biochem Pharmacol 57:727
7. Di Marco A, Gaetani M, Orezzi P, Scarpinato BM, Silvestrini R, Soldati M, Dasdia T, Valentini L (1964) Nature 201:706
8. Taatjes DJ, Gaudiano G, Resing K, Koch TH (1996) J Med Chem 39:4135
9. Smith TH, Fujiwara AN, Lee WW, Wu HY, Henry DW (1977) J Org Chem 42:3653
10. Hautala A, Torkkell S, Räty K, Kunnari T, Kantola J, Mäntsälä P, Hakala J, Ylihonko K (2003) J Antibiot 56:143
11. Brockmann H Jr, Legrand M (1963) Tetrahedron 19:395
12. Brockmann H, Brockmann H Jr, Niemeyer J (1968) Tetrahedron Lett 45:4719
13. Brockmann H, Boldt P (1960) Naturwissenschaften 47:134
14. Yoshimoto A, Matsuzawa Y, Oki T, Takeuchi T, Umezawa H (1981) J Antibiot 34:951
15. StraussD(1983) Type-specific separation of anthraquinone derivatives.DD200 671 A1 (Chem Abstr ChemAbstr 100:6205
16. Thomson RH (1971) Naturally occurring quinones, vol 2, 2nd edn. Academic, New York
17. Thomson RH (1987) Naturally occurring quinones, vol 3, 3nd edn. Academic, New York
18. Schripsema J, Dagnino D (1996) Phytochemistry 42:177
19. Ballabio M, Vigevani A (1990) Chim Oggi 8:33
20. Vigevani A, Ballabio M, Gandini E, Penco S (1985) Magn Resonance Chem 23:344
21. Brockmann H Jr, Budzikiewicz H, Djerassi C, Brockmann H, Niemeyer J (1965) Chem Ber 98:1260
22. Reed RI, Reid WK (1963) Tetrahedron 19:1817
23. Hirayama K, Akashi S, Toshihiko A, Issei H, Yuzuru E, Hajumu M, Hiroshiro S, Asao M (1987) Biomed Environm Mass Spectrom 4:305
24. Brazhnikova MG, Zbarskii VB, Ponomarenko VL, Potapova NP (1974) J Antibiot 27:254
25. Kende AS, Tsay YG, Mills JE (1976) J Am Chem Soc 98:1967
26. Pettit GR, Einck JJ, Herald CL, Ode RH, von Dreele RB, Brown P, Brazhnikova MG, Gauze GF (1975) J Am Chem Soc 97:7387
27. Fujiwara A, Tazoe M, Hoshino T, Sekine Y, Masuda S, Nomura S (1981) J Antibiot 34:912
28. Hoshino T, Setoguchi Y, Fujiwara A (1984) J Antibiot 37:1469
29. Maskey RP (2001) Neuartige Wirkstoffe aus marinen Streptomyceten: Sagunamycine, Parimycin, Himalomycin, Gottingamycin, Dhanyabadomycin, Akashine und stark cytotoxische Trioxacarcine mit hoher Anti-Malaria Aktivität. PhD thesis, University of Göttingen
30. Fotso-Fondja Yao CB (2008) Aqabamycins, rare nitro maleimides and other novel metabolites from microorganisms; generation and application of an HPLC-UV-ESI MS/MS database. PhD thesis, University of Göttingen
31. Webb JS, Broschard RW, Cosulich DB, Mowat JH, Lancaster JE (1962) J Am Chem Soc 84:3183
32. El-Naggar MY (2007) J Microbiol 45:262 (Korea
33. Celmer WD, Murai K, Rao KV, Tanner FW, MarshWS (1957-1958) The quinocycline complex, I isolation and characterisation. In: Antibiotics annual. Medical Encyclopedia, New York, pp 484-492
34. Yasuhiro I, Hiroko H, Toshikazu O, Furumai T (2002) J Antibiot 55:134
35. Furumai T, Igarashi Y, Higuchi H, Saito N, Oki T (2002) J Antibiot 55:128
36. Igarashi Y, Futamata K, Fujita T, Sekine A, Senda H, Naoki H, Furumai T (2003) J Antibiot 56:107
37. Igarashi Y, Iwashita T, Fujita T, Naoki H, Yamakawa T, Yoshida R, Furumai T (2003) J Antibiot 56:705
38. Zitouni A, Boudjella H, Mathieu F, Sabaou N, Lebrihi A (2004) J Antibiot 57:367
39. Zitouni A, Mathieu F, Coppel Y, Pont F, Sabaou N, Lebrihi A (2004) J Antibiot 57:373
40. Xiao C, Si S, Zhang Y, Otani T, Yoshida K (2001) Zhongguo Kangshengsu Zazhi 26:85
41. Pullen C, Schmitz P, Meurer K, von Bamberg D, Lohmann S, de Castro Franca S, Groth I, Schlegel B, Mollmann U, Gollmick F, Gräfe U, Leistner E (2002) Planta Med 216:162
42. Torikoshi K, Hirano A, Sugiura Y, Nakajima S, Ojiri K, Suda H (1999) BE-45985 derivatives, their manufacture, Streptomyces species producing them, and antitumor agents. Jpn Kokai Tokkyo Koho. JP Patent 11 021 263 (Chem Abstr 130:191872
43. Strelitz F, Flon H, Weiss U, Asheshov N (1956) J Bact 72:9094
44. Johdo O, Tone H, Okamoto R, Yoshimoto A, Naganawa H, Sawa T, Takeuchi T (1991) J Antibiot 44:1155
45. Broadhurst MJ, Hassall CH, Thomas GJ (1982) J Chem Soc Perkin Trans 1, p 2249
46. Monneret C, Florent JC, Bennani F, Sedlacek HH, Kraemer HP (1988) Actual Chim Therapeut 15:253
47. Brockmann H, Lenk W (1959) Chem Ber 92:1904
48. Oki T, Kitamura I, Matsuzawa Y, Shibamoto N, Ogasawara T, Yoshimoto A, Inui T, Naganawa H, Takeuchi T, Umezawa H (1979) J Antibiot 32:801
49. Bieber LW, Da Silva FilhoAA, DeMello JF, De LimaOG, DoNascimentoMS, VeithHJ, Von der Saal W (1987) J Antibiot 40:1335
50. Nakagawa M, Furihata K, Furihata K, Adachi K, Seto H, Otake N (1986) J Antibiot 39:1178
51. Shaaban M (2004) Bioactive secondary metabolites from marine and terrestrial bacteria: isoquinolinequinones, bacterial compounds with a novel pharmacophor. PhD thesis, University of Göttingen
52. Fomicheva EV, Fedorova GB, Potapova NP, Katrukha GS (1992) J Antibiot 45:1185
53. Phipps RK, Blunt JW, Cole ALJ, Munro MHG (2004) ARKIVOC, p 94
54. Tanaka Y, Gräfe U, Yazawa K, Mikami Y, Ritzau M (1997) J Antibiot 50:822
55. Brodasky TF, Mizsak S, Hoffstetter JR (1985) J Antibiot 38:849
56. Oki T, Yoshimoto A, Matsuzawa Y, Takeuchi T, Umezawa H (1981) J Antibiot 34:916
57. MatsuzawaY, YoshimotoA, ShibamotoN, TobeH, Oki T, NaganawaH, TakeuchiT, Umezawa H (1981) J Antibiot 34:959
58. Oki T, Matsuzawa Y, Kiyoshima K, Yoshimoto A, Naganawa H, Takeuchi T, Umezawa H (1981) J Antibiot 34:783
59. Itoh T, Kinoshita M, Wei H, Kobayashi M (2003) Chem Pharm Bull 51:1402
60. Arcamone F, Cassinelli G, Orezzi P, Franceschi G, Mondelli R (1964) J Am Chem Soc 86:5335
61. Arcamone F, Cassinelli G, Fantini G, Grein A, Orezzi P, Pol C, Spalla C (1969) Biotechnol Bioeng 11:1101
62. Bonadonna G, Monfardini S (1969) Lancet 1(7599):837
63. Takahashi Y, Naganawa H, Takeuchi T, Umezawa H, Komiyama T, Oki T, Inui T (1977) J Antibiot 30:622
64. Komiyama T, Matsuzawa Y, Oki T, Inui T, Takahashi Y, Naganawa H, Takeuchi T, Umezawa H (1977) J Antibiot 30:619
65. Oki T, Yoshimoto A, Kouno K, Inui T, Takeuchi T, Umezawa H (1981) Anthracycline glycosides. EP Patent 26 849 (Chem Abstr 95:40852
66. Nakagawa M, Kawai H, Hayakawa Y, Seto H, Otake N (1985) J Antibiot 38:1622
67. Komatsu Y, Takahashi O, Hayashi H (1998) J Antibiot 51:85
68. Yoshimoto A, Jodo O, Watanabe Y, Okamoto R, Takeuchi T (1990) Preparation of antibiotic D788-7 from carborubicin as antitumor agent. EP Patent 355 843 (Chem Abstr 113:59778
69. Umezawa H, Odagawa A, Kataoka S, Nakajima S (1988) Preparation of anthracycline compound. EP Patent 251 327 (Chem Abstr 110:24243
70. Tao P, Wang S, Zhang G, Cai S, Li H, Jin W (1990) Zhongguo Kangshengsu Zazhi 15:170
71. Jin W, Chen J, Zhang Y, Li H, Tao P (1990) Zhongguo Kangshengsu Zazhi 15:399
72. Speitling M (1998) Vergleich der metabolischen Kapazitätmariner und terristrischer Mikroorganismen-Isolierung und Strukturaufklärung von Branimycin, Bromalterochromid A/B und weiteren Stoffwechselprodukten. PhD thesis, University of Göttingen
73. Maeda A, Yazawa K, Mikami Y, Ishibashi M, Kobayashi J (1992) J Antibiot 45:1848
74. Mikami Y, Yazawa K, Ohashi S, Maeda A, Akao M, Ishibashi M, Kobayashi J, Yamazaki C (1992) J Antibiot 45:995
75. SpeitlingM, NattewanP, YazawaK, MikamiY, Grün-Wollny I, RitzauM, LaatschH, Gräfe U (1998) J Antibiot 51:693
76. Oki T, Yoshimoto A, Matsuzawa Y, Takeuchi T, Umezawa H (1980) J Antibiot 33: 1331
77. Matsuzawa Y, Yoshimoto A, Oki T, Naganawa H, Takeuchi T, Umezawa H (1980) J Antibiot 33:1341
78. Seeber C, Fleck W (1974) Z Allg Mikrobiol 14:503
79. Brockmann H, Greve H (1975) Tetrahedron Lett 16:831
80. Yoshimoto A, Jodo O, Watanabe Y, Ishikura T, Osanawa H, Sawa T, Takeuchi T, Umezawa H (1988) Novel anthracyline antibiotics Y267-1, Y262-3, and Y262-3 manufacture with Streptomyces violacens. Jpn Kokai Tokkyo Koho JP Patent 63 066 194 (Chem Abstr 110:113191
81. Johdo O, Watanabe Y, Ishikura T, Yoshimoto A (1991) J Antibiot 41:1130
82. Kawai H, Hayakawa Y, Nakagawa M, Furihata K, Seto H, Otake N (1987) J Antibiot 40:1273
83. Huetter K, Baader E, Frobel K, Zeeck A, Bauer K, GauW, Kurz J, Schroeder T, Wuensche C, Karl W, Wendisch D (1986) J Antibiot 39:1193
84. Kind R, Huetter K, Zeeck A, Schmidt-Baese K, Egert E (1989) J Antibiot 42:7
85. Nishimura Y, Ishii K, Kondo S (1990) J Antibiot 43:54
86. Ishii K, Kondo S, Nishimura Y, Hamada M, Takeuchi T, Umezawa H (1983) J Antibiot 36:451
87. Ubukata M, Osada H, Kudo T, Isono K (1993) J Antibiot 46:936
88. Ubukata M, Uzawa J, Osada H, Isono K (1993) J Antibiot 46:942
89. Blumauerova M, Kralovcova E, Mateju J, Jizba J, Vanek Z (1979) Folia Microbiol 24:117 (Prague, Czech Republic
90. YoshimotoA, JohdoO, TakatsukiY, IshikuraT, SawaT, TakeuchiT, UmezawaH (1984) J Antibiot 37:935
91. Matsuzawa Y, Oki T, Takeuchi T, Umezawa H (1981) J Antibiot 34:1596
92. Laatsch H (2008) AntiBase, a data base for rapid structural determination of microbial natural products, and annual updates. Wiley-VCH, Weinheim. See also http://www.gwdg.de/∼ucoc/laatsch/, last visited 24 March 2008
93. Fujiwara A, Hoshino T (1983) Optically active anthracycline glycosides, 4-deoxyaclacinomycins A and B and pharmaceutical preparations. EP Patent 83 019 (Chem Abstr 99:120690
94. Oki T, Shibamoto N, Matsuzawa Y, Ogasawara T, Yoshimoto A, Kitamura I, Inui T, Naganawa H, Takeuchi T, Umezawa H (1977) J Antibiot 30:683
95. Umezawa H, Takeuchi T, Hamada M, Naganawa H, Sawa T, Uchida T, Imoto M (1986) Anthracycline derivatives and their use as medicaments. EP Patent 167 935 (Chem Abstr 104:184852
96. Mitscher LA, McCrae W, Andres WW, Lowery JA, Bohonos N (1964) J Pharm Sci 53:1139
97. Tamotsu K, Yasuhiro I, Shunichi O (2002) Isoquinocycline antibiotics manufacture with Micromonospora. Jpn Kokai Tokkyo Koho JP Patent 2 002 212 187 (Chem Abstr 137:139486
98. Tulinsky A (1964) J Am Chem Soc 86:5368
99. Cosulich DB, Mowat JH, Broschard RW, Patrick JB, Meyer WE (1963) Tetrahedron Lett 63:453
100. Igarashi Y, Higuchi H, Oki T, Furumai T (2002) J Antibiot 55:134
101. Igarashi Y, Higuchi H, Oki T, Furumai T (2003) J Antibiot 56:C1
102. Shaaban KA (2008) Metabolites from marine and terrestrial bacteria. PhD thesis, University of Göttingen
103. Tanaka H, Yoshioka T, Shimauchi Y, Matsuzawa Y, Oki T, Inui T (1980) J Antibiot 33:1323
104. Fujii S, Kubo K, Johdo O, Yoshimoto A, Ishikura T, Naganawa H, Sawa T, Takeuchi T, Umezawa H (1986) J Antibiot 39:473
105. Otake N, Munetsuka Y, Munetsuka J, Toda Y (1986) Antitumor agent 11-deoxyrubeomycin A manufacture and use. Jpn Kokai Tokkyo Koho JP Patent 61 152 692 (Chem Abstr 106:17032
106. Wang Y, Niemi J, Mäntsälä P (2002) FEMS Microbiol Lett 208:117
107. Uchida T, Imoto M, Masuda T, Yoshimoto H, Imamura K, Sawa T, Naganawa H, Takeuchi T, Umezawa H (1985) J Antibiot 38:795
108. Kunnari TJ, Ylihonko KPJ, Klika KD, Mäntsälä PI, Hakala JML (2000) J Org Chem 65:2851
109. Ylihonko K, Torkkell S, Palmu K, Hakala J (2000) Gene cluster involved in nogalamycin biosynthesis and its use in production of hybrid antibiotics. WO Patent 2 000 024 775 (Chem Abstr 132:333446
110. Rho Y, Kang HS, Sin HS (1993) Yakhak Hoechi 37:555
111. Johdo O, Nishida H, Okamoto R, Yoshimoto A, Takeuchi T (1995) J Antibiot 48:1153
112. Ylihonko K, Hakala J, Kunnari T (1999) Hybrid anthracyclines for cancer therapy from genetically engineered Streptomyces galilaeus.WO Patent 9 958 544 (Chem Abstr 131:332095
113. Yoshimoto A, Johdo O (1996) Anthracycline antibiotics manufacture with Streptomyces. Jpn Kokai Tokkyo Koho JP Patent 08 113 587 (Chem Abstr 125:112917
114. Niemi J, Ylihonko K, Hakala J, Paerssinen R, Kopio A, Mäntsälä P (1994) Microbiology 140:1351
115. Morioka M, Sasaki T, Suzuki K, Nagai K, Yamaguchi H, Nohara C, Tokunaga T, Hiramoto M, Takebayashi Y (1990) Antitumor anthracyclines from Nocardia. EP Patent 387 830 (Chem Abstr 114:227481
116. Yoshimoto A, Johdo O, Fujii S, Kubo K, Nishida H, Okamoto R, Takeuchi T (1992) J Antibiot 45:1255
117. Eckardt K, Schumann G, Tresselt D, Ihn W (1988) J Antibiot 41:788
118. Tresselt D, Sedmera P, Eckardt K (1990) Pharmazie 45:775
119. Yoshimoto A, Toshikazu O, Oki O, Takeuchi T, Umzawa H (1980) J Antibiot 33:1158
120. Hoshino T, Tazoe M, Nomura S, Fujiwara A (1982) J Antibiot 35:1271
121. Arora SK (1985) J Antibiot 38:1788
122. Tresselt D, Eckardt K, Tax J (1975) Tetrahedron 31:613
123. Torkkell S, Kunnari T, Palmu K, Hakala J, Mäntsälä P, Ylihonko K (2000) Antimicrob Agents Chemother 44:396
124. Chen Y, Du R, Hao Y, Li M (1996) Zhongguo Kangshengsu Zazhi 21:168-179
125. Oki T, Matsuzawa Y, Yoshimoto A, Numata K, Kitamura I, Hori S, Takamatsu A, Umezawa H, Ishizuka M, Naganawa H, Suda H, Hamada M, Takeuchi T (1975) J Antibiot 28:830
126. Oki T, Matsuzawa Y, Yoshimoto A, Numata K, Kitamura I, Hori S, Takamatsu A, Umezawa H, Ishizuka M, Naganawa H, Suda H, Hamada M, Takeuchi T (1979) J Antibiot 32:791
127. Cassinelli G, Giovanni R, Ruggieri D, Arcamone F, Grein A, Merli S, Spalla C, Casazza AM, di Marco A, Pratesi G (1982) J Antibiot 35:164
128. Yoshimoto A, Ogasawara T, Kitamura I, Oki T, Inui T, Takeuchi T, Umezawa H (1979) J Antibiot 32:472
129. Ihn W, Wetzstein H, Graefe U, Eckardt K, Dornberger K, Fleck W, Tresselt D (1988) Manufacture of aclacinomycin Y with a novel Streptomyces strain. DD Patent 259 207 (Chem Abstr 112:53723
130. Hoshino T, Sekine Y, Fujiwara Y (1983) J Antibiot 36:1458
131. Fujiwara A, Hoshino T, Tazoe M (1982) Tetracyclic compounds and pharmaceutical preparations containing them. Fr Demande. FR Patent 2 492 386 (Chem Abstr 98:3537
132. Katsuyoshi S, Hirofumi F, Shunro M, Toshikazu O (1981) J Antibiot 34:770
133. Johdo O, Yoshioka T, Naganawa H, Takeuchi T, Yoshimoto A (1996) J Antibiot 49:669
134. Kim HS, Kim YH, Yoo OJ, Lee JJ (1996) Biosc Biotechnol Biochem 60:906
135. Yang S-W, Chan T-M, Terracciano J, Patel R, Loebenberg D, Chen G, PatelM, Gullo V, Pramanik B, Chu MA (2004) J Antibiot 57:601
136. Jizba JV, Sedmera P, Vokoun J, Blumauerova M, Vanek Z (1981) Coll Czech Chem Comm 46:2129
137. Uno H, Naruta Y, Maruyama K (1984) Tetrahedron 40:4725
138. Asahi Chemical Industry Co Ltd Japan (1985) Aklavinone derivatives. Jpn Kokai Tokkyo Koho JP Patent 60 058 944 (Chem Abstr 103:71082
139. Maskey RP, Grün-Wollny I, Laatsch H (2003) J Antibiot 56:795
140. Kende AS, Johnson S (1985) J Org Chem 50:727
141. Fujiwara M, Fujiwara A, Hoshino T, Tazoe M, Sekine Y (1978) Antibiotic SM-173B. DE Patent 2 804 495 (Chem Abstr 89:195401
142. Grein A, Merli S, Celestino S (1980) J Antibiot 33:1462
143. Cassinelli G, Di Matteo F, Forenza S, Ripamonti MC, Arcamone GRF, Di Marco A, Casazza AM, Soranzo CL Pratesi G (1980) J Antibiot 33:1468
144. Arcamone F, Cassinelli J, DiMatteo F, Forenza S, RipamontiMC, Rivola G, Vigevani A, Clardy J, McGabe T (1980) J Am Chem Soc 102:1462
145. Kelly RT, Ananthasubramanian L, Borah K, Gillard JW, Goerner RN Jr, King PF, Lyding JM, Tsang W-G, Vaya J (1984) Tetrahedron 40:4569
146. Kraus GA, Taschner MJ (1977) Tetrahedron Lett 52:4575
147. Braun M (1984) Tetrahedron 40:4585
148. Zhang Y, Jin W (1991) Isolation and structure determination of minor components of mutactimycins, a group of new anthracycline antibiotics. Zhongguo Kangshengsu Zazhi 16:157 [Chem Abstr 116:55211]
149. Yoshimoto A, Jodo O, Watanabe Y, Ishikura T, Osanawa H, Sawa T, Takeuchi T, Umezawa H (1988) Novel anthracycline antibiotic D788-16 manufacture with Streptomyces. Jpn Kokai Tokkyo Koho JP Patent 63 066 193 (Chem Abstr 110:22306
150. Nash CH, Shearer MC, Snader KM, Valenta JR, Cooper D (1981) Anthracycline antibiotics by Streptosporangium fragilis Shearer sp. nov. ATCC 31519. US Patent 4 293 546 (Chem Abstr 96:50693
151. Tsuji T, Takesawa M, Kida T, Morioka H, Eto Y, Shibai H, Horino K (1986) Manufacture of the anthracyclines TMF518C and TMF518D. Jpn Kokai Tokkyo Koho JP Patent 61 005 090 (Chem Abstr 111:113762
152. Brockmann H, Niemeyer J (1968) Chem Ber 101:1341
153. Terajima A, Kimura Y, Suzuki M, Abe R, Matsumoto M (1986) 4-Demethoxyadriamycin. Jpn Kokai Tokkyo Koho JP Patent 61 078 797 (Chem Abstr 105:227232
154. Arcamone F, Bernardi L, Patelli B, Giardino P, di Marco A, Casazza AM, Soranzo C, Pratesi G (1978) Experientia 34:1255
155. Bakina EV, Yartseva IV, Povarov LS, Aleksandrova LG, Tulemisova KA, Mamonova LP, Preobrazhenskaya MN (1989) Bioorg Khim 15:1423
156. Bakina EV, Yartseva IV, Povarov LS, Aleksandrova LG, Tulemisova KA, Mamonova LP, Preobrazhenskaya MN (1981) Antibiotics DC-44-A and DC-44-B. Jpn Kokai Tokkyo Koho JP Patent 56 051 435 (Chem Abstr 95:148696
157. Brockmann H, Lenk W (1960) Naturwissenschaften 47:135
158. Balk W (1995) Neue Naturstoffe aus dem Screening mariner Actinomyceten-Isolierung und Strukturaufklärung der Lagumycine und des Oceamycins. PhD thesis, University of Göttingen
159. Nettleton DE Jr, Bradner WT, Bush JA, Coon AB, Moseley JE, Myllymaki RW, O'Herron FA, Schreiber RH, Vulcano AL (1977) J Antibiot 30:525
160. Akihiro Y, Toshikazu O, Taiji I (1978) J Antibiot 31:92
161. Bradner WT, Misiek M (1977) J Antibiot 30:519
162. Nettleton DE Jr, Balitz DM, Doyle TW, Bradner WT, Johnson DL, O'Herron FA, Schreiber RH, Coon AB, Moseley JE, Myllymaki RW (1980) J Nat Prod 43:242
163. Tresselt D, Ihn W, Schlegel B, Fleck W (1987) Z Chemie 27:444
164. Huth F (1999) Einsatz der Neutronenaktivierungsanalyse und der Elektrospray-Massenspektrometrie im Screening nach Organohalogenverbindungen- Strukturaufklärung cyclischer Peptide durchMS-Methoden. PhD thesis, University of Göttingen
165. Nettleton DE Jr, Doyle TW, Grossman JH, Bradner WT, Moseley JE, Bray SW (1984) J Nat Prod 47:698
166. Doyle TW, Nettleton DE, Grulich RE, Balitz DM, Johnson DL, Vilcano AL (1979) J Am Chem Soc 101:7041
167. Nakagawa M, Okazaki T, Furihata K, Seto H, Otake N (1987) Agric Biol Chem 51:3431
168. Frolova VI, Kuzovkov AD, Rozynov BV, Taig MM, Ivanitskaya LP, Terent'eva TG (1982) Antibiotiki 27:326 (Moscow)
169. Ettlinger L, Gräumann E, Hütter R, Keller-SchierleinW, Kradolfer F, Neipp L, Prelog V, Reusser P, Zähner H (1959) Chem Ber 92:1867
170. Nair MG, Mishra SK, Putnam AR, Pandey RC (1992) J Antibiot 45:1738
171. Iwao KI, Norio S, Toshikazu O, Taiji I, Hiroshi N, Masaaki I, Toru M, Tomio T, Umezawa H (1977) J Antibiot 30:616
172. Nakata M, SaitoM, InouyeY,Nakamura S,HayakawaY, SetoH(1992) JAntibiot 45:1599
173. Kendee AS, Tsay YG (1977) J Chem Soc Chem Commun, p 140
174. Suzukake TK, Moriya Y, Yamazaki K, Hori M, Hosokawa N, Sawa T, Iinuma H, Naganawa H, Imada C, Hamada M (1990) J Antibiot 43:1489
175. Kunnari T, Tuikkanen J, Hautala A, Hakala J, Ylihonko K, Mäntsälä K (1997) J Antibiot 50:496
176. Bauman JG, Hawley RC, Rapoport H (1985) J Org Chem 50:1569
177. Rawlings BJ (1999) Nat Prod Rep 16:425
178. Rongsheng D, Shuquan Z, Yongle C, Ning C, Qijian S, Xiaoqing C (1983) Kangshengsu 8:44
179. Yoshimoto A, Tobe H, Ishikura, T, Takeuchi T, Umezawa H (1983) Anthracycline antibiotics. EP Patent 72 974 (Chem Abstr 98:214137
180. Wiley PF, Elrod DW, Slavicek JM, Marshall VP (1980) J Antibiot 33:819
181. Elrod DW, Marshall VP, Wiley PF (1980) Dihydrosteffimycin compounds. US Patent 4 209 611 (Chem Abstr 93:184275
182. Wiley PF, Marshall VP (1975) J Antibiot 28:838
183. Marshall VP, Elrod DW, Koert JM, Reisender EA, Wiley PF (1978) Steffimycinol. US Patent 4 077 844 (Chem Abstr 89:4583
184. Kelly RC, Schletter I, Koert J, MacKellar FA, Wiley PF (1977) J Org Chem 42:3591
185. Brodasky TF, Reusser F (1974) J Antibiot 27:809
186. Wiley PF, Koert JM, Elrod DW, Reisender EA, Marshall VP (1977) J Antibiot 30:649
187. Wiley PF, Elrod DW, Marshall VP (1978) J Org Chem 43:3457
188. Laboratoires Hoechst SA, Fr (1986) Steffimycinone analogs. Jpn Kokai Tokkyo Koho JP Patent 61 047 439 (Chem Abstr 105:152829
189. Gesson JP, Jacquesy JC, Renoux B (1983) Tetrahedron Lett 24:2761
190. Kelly RC (1976) Steffimycinone, 7-deoxysteffimycinone and derivatives. US Patent 3 976 667 (Chem Abstr 86:5220
191. Itoh T, Kinoshita M, Aoki S, Kobayashi M (2003) J Nat Prod 66:1373
192. Yoshimoto A, Matsuzawa Y, Matsushita Y, Toshikazu O, Tomio T, Umezawa H (1981) J Antibiot 34:1492
193. Prikrylova V, Podojil M, Sedmera P, Vokoun J, Vanek Z, Brazhnikova MG, Kudinova MK (1980) Collect Czech Chem Commun 45:1991
194. Yoshimoto A, Fujii S, Johdo O, Kubo K, Nishida H, Okamoto R (1993) J Antibiot 46:56
195. Barskii VB, Potapova NP, Brazhnikova MG, Rozynov BV, Sibel'dina LA, Sepetov NF (1980) Antibiotiki 25:488 (Moscow
196. Povarov LS, Gol'dberg LE, Bazhanov VS, Shepelevtseva NG Vertogradova TP, Averbukh LA (1981) Antibiotiki 26:620 (Moscow
197. Ogawa Y, Sugi H, Fujikawa N, Mori H (1981) J Antibiot 34:938
198. Ogawa Y, Mori H, Yamada N, Kon K (1984) J Antibiot 37:44
199. Mori H, Tamai K, Ogawa Y, Sugi H, Fujikawa N (1981) Anthracycline antibiotic and a pharmaceutical composition containing it. EP Patent 25 713 (Chem Abstr 95:113370
200. Hirofumi N, Mitsunobu H, Yoshinori Y, Katsuhiko A, Katsuichi S (1988) J Antibiot 41:404
201. Koyama T, Nakayama M, Tamura K, Shimada S, Kumazawa E, Miyata N (1987) Manufacture of novel anthracycline antibiotics with Actinomadura. Jpn Kokai Tokkyo Koho JP Patent 62 289 195 (Chem Abstr 108:203292
202. Kimura K-I, Nakayama S, Miyata N, Kawanishi G (1989) J Antibiot 42:127
203. Kimura K, Nakayama M, Koyama T, Shimada S, Miyata N (1989) Stable barminomycin I-DNA conjugates, novel anthracycline compounds. Jpn Kokai Tokkyo Koho JP Patent 01 040 497 (Chem Abstr 111:152155
204. Kimura KI, Nakayama S, Miyata N, Takeshita Y, Kawanishi G (1988) J Antibiot 41: 411
205. Fehlhaber HW, Kraemer HP, Franco CM, Mathew MT, Desikan KR, Ganguli BN (1986) Anthracycline antibiotics. DE Patent 3 446 052 (Chem Abstr 105:170623
206. Yoshimoto A, Fujii S, Kubo K, Ishikura T, Sawa T, Takeuchi T, Umezawa H (1986) Anthracycline antibiotics. EP Patent 171 677 (Chem Abstr 105:96048
207. Yoshimoto A, Fujii S, Osamu J, Katsuro K, Tomoyuki I, Hiroshi N, Tsutomu S, Takeuchi T, Umezawa H (1986) J Antibiot 39:902
208. Otake N, Odakawa A, Nakajima S (1986) Manufacture of antitumor agent R20X10 by Actinomadura roseoviolacea. Jpn Kokai Tokkyo Koho JP Patent 61 152 693 (Chem Abstr 106:17031
209. Otake N, Odakawa A, Nakajima S (1986) Manufacture of anthracycline compound R20X2 and its use. Jpn Kokai Tokkyo Koho JP Patent 61 076 498 (Chem Abstr 106:3844
210. Krohn K, Priyono W (1984) Tetrahedron 40:4609
211. Arai, Y, Takeda Y, Sato T, Watanabe N, Kamimura M (1987) Antitumor antibiotics BA32 and their manufacture with Streptomyces. Jpn Kokai Tokkyo Koho JP Patent 62 207 293 (Chem Abstr 108:220355
212. Yoshimoto A, Matsuzawa Y, Ishikura T, Sawa T, Takeuchi T, Umezawa T (1984) J Antibiot 37:920
213. Yoshimoto A, Johdo O, Watanabe Y, Nishida H, Okamoto R, Takeuchi T (1992) J Antibiot 45:1005
214. Fleck W, Strauss D, Koch W, Prauser H (1974) Z Allg Mikrobiol 14:551
215. Fleck W, Strauss D, Koch W, Prauser H (1975) Antibiotiki 20:966 (Moscow
216. Shimosaka A, Hayakawa Y, Nakagawa M, Furihata K, Seto H, Otake N (1987) J Antibiot 40:116
217. Aretz W, Berscheid HG, Huber G, Fehlhaber HW, Kraemer HP, Sedlacek HH, Ganguli BN, Sood RS, Gandhi J, Reddy GC (1985) Microbiological production of anthracycline derivatives, and their cytostatic use. DE Patent 3 323 025 (Chem Abstr 102:147547
218. Aretz W, Berscheid HG, Huber G, Fehlhaber HW, Kraemer HP, Sedlacek HH, Ganguli BN, Sood RS, Gandhi J, Reddy GC (1990) Microbiological production of anthracycline derivatives, and their cytostatic use. EP Patent 0 131 181
219. Berscheid HG, Boettger D, Kraemer HP (1987) Preparation of anthracycline tetrasaccharides as neoplasm inhibitors. EP Patent 207 463 (Chem Abstr 107:176411
220. Uchida T, ImotoM,Masuda T, Imamura K,Hatori Y, Sawa T,Naganawa H,Hamada M, Takeuchi T, Umezawa H (1983) J Antibiot 36:1080
221. Aretz W, Berscheid HG, Fehlhaber HW, Boettger D, Kraemer HP (1986) 1-Hydroxycytorhodins, their microbiological preparation and their use as cytostatic agents. EP Patent 167 954 (Chem Abstr 104:147150
222. Li M, Chenn YL (1986) J Antibiot 39:430
223. Morioka H, Etoh Y, Horino I, Takezawa M, Ando T, Hirayama K, Kano H, Shibai H (1985) Agric Biol Chem 49:1951
224. Ando T, Hirayama K, Murai A, Tsuji T, Morioka H, Takesawa M, Shibai H, Horino K, Eto Y (1985) Antitumor agent cosmomycin c manufacture from Streptomyces. Jpn Kokai Tokkyo Koho JP Patent 60 248 614 (Chem Abstr 104:166917
225. Aretz W, Berscheid HG, Fehlhaber, HW, Huber G, Kraemer HP (1985) Microbiological production of anthracycline derivatives. DE Patent 3 415 544 (Chem Abstr 104:107912
226. Hedtmann U, Fehlhaber HW, Sukatsch DA, Weber M, Hoffmann D, Kraemer HP (1992) J Antibiot 45:1373
227. Ando T, Hirayama K, Takahashi R, Horino I, Etoh Y, Morioka H, Shibai H, Murai A (1985) Agr Biol Chem 49:259
228. Morioka H, Etoh Y, Horino I, Takezawa M, Ando T, Hirayama K, Kano H, Shibai H (1985) Agr Biol Chem 49:1951
229. Speitling M, Gruen-Wollny I, Fiebig HH, Laatsch H (2001) Rhodomycinonederivatives. WO Patent 2 001 096 352 (Chem Abstr 136:36486
230. Biedermann E, Braeuniger H (1972) Pharmazie 27:782
231. Saito S, Katsuda Y, Johdo O, Yoshimoto A (1995) Biosci Biotechnol Biochem 59:135
232. Brockmann H, Waehneldt T, Niemeyer J (1969) Tetrahedron Lett 10:415
233. Brockmann H, Scheffer B, Stein C (1973) Tetrahedron Lett 14:3699
234. Matsuzawa Y, Yoshimoto A, Oki T, Inui T, Takeuchi T, Umezawa H (1979) J Antibiot 32:420
235. Brockmann H, Wähneldt H (1963) Naturwissenschaften 50:43
236. Brockmann H, Niemeyer J, Rode W (1965) Chem Ber 98:3145
237. Johdo O, Yoshioka T, Takeuchi T, Yoshimoto A (1997) J Antibiot 50:522
238. Schlegel B, Ihn W, Fleck WF (1980) Z Allg Mikrobiol 20:531
239. Podojil M, Blumauerova M, Prikrylova V, Vanek Z, Gauze GF, Maksimova TS (1980) Folia Microbiologica 25:464 (Prague
240. Brockmann H, Scheer M (1971) β-Rhodomycin V from Streptomyces purpurascens. DE Patent 2 012 808 (Chem Abstr 76:44690
241. Otaka N, Odakawa A, Nakajima S, Yoneshima N (1986) Antitumor agent R20X4 manufacture with Actinomadura roseoviolacea. Jpn Kokai Tokkyo Koho JP Patent 61 137 893 (Chem Abstr 106:194766
242. Connors NC, Bartel PL, Strohl WR (1990) J Gen Microbiol 136:1887
243. Brockmann H, Franck B (1955) Chem Ber 88:1792
244. Brockmann H, Brockmann H Jr (1961) Chem Ber 94:2681
245. Olano C, Lomovskaya N, Fonstein L, Roll JT, Hutchinson CR (1999) Chem Biol 6:845
246. Johdo O, Watanabe Y, Ishikura T, Yoshimoto A (1991) J Antibiot 44:1121
247. Kim HS, Hong YS, Kim YH, Yoo OL, Lee JJ (1996) J Antibiot 49:355
248. Reddy GCS, Sahai R, Fehlhaber HW, Ganguli BN (1985) J Antibiot 38:1423
249. Ishizumi K, Ohashi N, Tanno N (1987) J Org Chem 52:4477
250. Swenton JS, Raynolds PW (1978) J Am Chem Soc 100:6188
251. Brazhnikova MG, Konstantinova NV, Mezentsev AS, Pomazkova VA (1968) Antibiotiki 13:781 (Moscow
252. Arcamone F, Franceschi G, Penco S, Selva A (1969) Tetrahedron Lett 10:1007
253. Toshikazu O, Yukio T, Hiroyasu T, Akihiro Y, Tomio T, Umezawa H (1981) J Antibiot 34:1229
254. Arcamone F, Franceschi G, Orezzi P, Penco S, Mondelli R (1968) Tetrahedron Lett 9:3349
255. Paulick RC, Casey ML, Whitlock HW (1976) J Am Chem Soc 98:3370
256. Bachur NR (1971) J Pharm Exp Therap 177:573
257. Arcamone F, Cassinelli G, Penco S, Tognoli L (2970) Antibiotic from Streptomyces fermentations. DE Patent 1 923 885 (Chem Abstr 72:131086
258. Smith RG (1982) Anal Chem 54:2006
259. Kanamaru T, Nozaki Y, Muroi M (1990) Isolation of antitumor substances TAN-1120 from the culture broth of Streptomyces triangulatus angiostaticus. EP Patent 376 177 (Chem Abstr 114:41033
260. Cassinelli G, Arlandini E, Ballabio M, Bordoni T, Geroni C, Giuliani F, Grein A, Merli S, Rivola G (1990) J Antibiot 43:19
261. Tsuchiya KS, Ishii T, Ikeno S, Kunimoto S, Kawauchi T, Otani T, Hori M (1997) J Antibiot 50:853
262. Kawauchi T, Sasaki T, Yoshida KI, Matsumoto H, Chen RX, Huang MY, Otani T (1997) J Antibiot 50:297
263. Kawauchi T, Sasaki T, Matsumoto H, Otani T, Chen RX, Huang MY, Yoshida KI (1996) IT-62-B substance and medicinal composition containing the same. WO Patent 9 602 659 (Chem Abstr 124:315172
264. Pokras LS, Snezhnova LP, Brazhnikova MG, Grigor'eva VM (1978) Antibiotiki 23:788 (Moscow
265. Julou L, Ducrot R, Fournel J, Ganter P, Maral R, Populaire P, Koenig F, Myon J, Pascal S, Pasquet J (1967) Arzneimittel-Forsch 17:948
266. Zbarskii VB, Lazhko EI, Potapova NP, Fomicheva EV, Saburova TP (1991) Bioorg Khim 17:1698
267. Arcamone F, Cassinelli G, Franceschi G, Orezzi P, Mondelli R (1968) Tetrahedron Lett 30:3353
268. Johdo O, Nishimura M, Tone H, Okamoto R (1993) Preparation of anthracycline compounds as antitumor agents. Jpn Kokai Tokkyo Koho JP Patent 05 039 242 (Chem Abstr 119:93691
269. Miyamoto Y, Ohta S, Johdo O, Nagamatsu Y, Yoshimoto A (2000) J Antibiot 53:828
270. Yoshimoto A, Kubo K, Fujii S, Ishikura T, Sawa T, Takeuchi T, Umezawa H (1985) Manufacture of novel anthracyline antibiotics with Streptomyces D788 mutant. Jpn Kokai Tokkyo Koho JP Patent 60 185 797 (Chem Abstr 105:5172
271. Yan X, Wang S, Wu J (1993) Chin Chem Lett 4:787
272. Yoshimoto A, Matsuzawa Y, Oki T, Naganawa H, Takeuchi T, Umezawa H (1980) J Antibiot 33:1150
273. Engel DW, Zechmeister K, Hoppe W (1972) Tetrahedron Lett 14:1323
274. Mansour FA, El-Sayed SA, El-Moughith AA, El-Sherbiny SA (1997) Egypt J Microbiol 32:69
275. El-Shirbiny SA, Abdel HF (1998) Egypt J Microbiol 33:469
276. Kiyo K, Sho S, Marunaka T, Miyake Y, Minami Y (1987) Antibiotic compounds 301 manufacture with Streptomyces virginiae. Jpn Kokai Tokkyo Koho JP Patent 62 030 793 (Chem Abstr 107:5739
277. Bhuyan BK, Kelly RB, Smith RM (1965) Nogalamycin and its production. US Patent 3 183 157 (Chem Abstr 63:20125
278. Bhuyan BK, Dietz A (1965) Antimicrob Agents Chemother 836
279. Wiley PF, MacKellar FA, Caron EL, Kelly RB (1968) Tetrahedron Lett 9:663
280. Wiley PF, Kelly RB, Caron EL, Wiley VH, Johnson JH, MacKellar FA, Mizsak SA (1977) J Am Chem Soc 99:542
281. Kirin Brewery Co., Ltd, Japan (1985) The anthracycline compound AG-2 and its antitumor activity. Jpn Kokai Tokkyo Koho JP Patent 60 025 999 (Chem Abstr 104:33023
282. Kawai H, Hayakawa Y, Nakagawa M, Furihata K, Shimazu A, Seto H, Otake N (1987) J Antibiot 40:1266
283. Aoki M, Shirai H, Nakayama N, Itezone Y, Mori M, Satoh T, Ohshima S, Watanabe J, Yokose K (1991) J Antibiot 44:635