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Agelasine

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G. C. Mangalindan, M. T. Talaue, L. J. Cruz, S. G. Franzblau, L. B. Adams, A. D. Richardson, C. M. Ireland and G. P. Conception, Planta Med., 2000, 66, 364
47:. At the present time a total of eleven 9-methyladeninium salts, agelasine A–I, epiagelasine C and agelin B, are known. All compounds carry a di 236: 184:
E. Piers and J. Y. Roberge, Tetrahedron Lett., 1992, 33, 6923; (b) H. Iio, K. Asao and T. Tokoroyama, J. Chem. Soc., Chem. Commun., 1985, 774
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Chemists have reproduced (−)-agelasine A, (−)-agelasine B, (−)-agelasine E, (−)-agelasine F, and (+)-agelasine D by
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H. Wu, H. Nakamura, J. Kobayashi, M. Kobayashi, Y. Ohizumi and Y. Hirata, Bull. Chem. Soc. Jpn., 1986, 59, 2495
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E. Piers, M. L. Livain, Y. Han, G. L. Plourde, L. Guy and W.-L. Yeh, J. Chem. Soc., Perkin Trans. 1, 1995, 963
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A. K. Bakkestuen, L.-L. Gundersen, D. Petersen, B. Utenova and A. Vik, Org. Biomol. Chem., 2005, 3, 1025
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K. Ishida, M. Ishibashi, H. Shigemori, T. Sasaki and J. Kobayashi, Chem. Pharm. Bull., 1992, 40, 766
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X. Fu, F. J. Schmitz, R. S. Tanner and M. Kelly-Borges, J. Nat. Prod., 1998, 61, 548
43:. Their contribution to the sponge is assumed to be some sort of protection against 59: 121:
H. Wu, H. Nakamura, J. Kobayashi and Y. Ohizumi, Tetrahedron Lett., 1984, 25, 3719
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H. Nakamura, H. Wu, Y. Ohizumi and Y. Hirata, Tetrahedron Lett., 1984, 25, 2989
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7-position. The agelasines are closely related in structure with the
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B. T. Utenova and L.-L. Gundersen, Tetrahedron Lett., 2004, 45, 4233
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K. Asao, H. Iio and T. Tokoroyama, Tetrahedron Lett., 1989, 30, 6401
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T. Hattori, K. Adachi and Y. Shizuri, J. Nat. Prod., 1997, 60, 411
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R. J. Capon and D. J. Faulkner, J. Am. Chem. Soc., 1984, 106, 1819
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Agelasines are associated with bioactivities such as
80:effects, as well as contractive responses of 8: 105: 7: 14: 20:Chemical structure of agelasine A 84:and inhibition of Na/K-ATPase ( 1: 237:Quaternary ammonium compounds 96:is reported for agelasine F. 263: 94:Mycobacterium tuberculosis 39:sp.). They are considered 27:are 7,9-dialkylpurinium 21: 41:secondary metabolites 31:isolated from marine 19: 242:Diterpene alkaloids 22: 92:activity against 67:organic synthesis 254: 221: 218: 212: 209: 203: 200: 194: 191: 185: 182: 176: 173: 167: 164: 158: 155: 149: 146: 140: 137: 131: 128: 122: 119: 113: 110: 88:). Furthermore, 262: 261: 257: 256: 255: 253: 252: 251: 227: 226: 225: 224: 219: 215: 210: 206: 201: 197: 192: 188: 183: 179: 174: 170: 165: 161: 156: 152: 147: 143: 138: 134: 129: 125: 120: 116: 111: 107: 102: 12: 11: 5: 260: 258: 250: 249: 244: 239: 229: 228: 223: 222: 213: 204: 195: 186: 177: 168: 159: 150: 141: 132: 123: 114: 104: 103: 101: 98: 82:smooth muscles 45:microorganisms 13: 10: 9: 6: 4: 3: 2: 259: 248: 245: 243: 240: 238: 235: 234: 232: 217: 214: 208: 205: 199: 196: 190: 187: 181: 178: 172: 169: 163: 160: 154: 151: 145: 142: 136: 133: 127: 124: 118: 115: 109: 106: 99: 97: 95: 91: 87: 83: 79: 75: 74:antimicrobial 70: 68: 63: 61: 57: 53: 50: 46: 42: 38: 34: 30: 26: 18: 216: 207: 198: 189: 180: 171: 162: 153: 144: 135: 126: 117: 108: 71: 64: 60:agelasimines 36: 24: 23: 231:Categories 100:References 52:side chain 25:Agelasines 86:NaKATPase 78:cytotoxic 49:terpenoid 90:in vitro 247:Purines 56:adenine 54:in the 33:sponges 37:Agelas 29:salts 76:and 69:. 233:: 62:. 35:(

Index


salts
sponges
secondary metabolites
microorganisms
terpenoid
side chain
adenine
agelasimines
organic synthesis
antimicrobial
cytotoxic
smooth muscles
NaKATPase
in vitro
Mycobacterium tuberculosis
Categories
Quaternary ammonium compounds
Diterpene alkaloids
Purines

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