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Atheronals

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under acidic conditions in natural solvents, yet atheronal A is either not framed at all or is a minor part in the aqueous buffer. Practically the measures of both of the atheronals are equivalent were shaped by the response of cholesterol with human myeloperoxidase (MPO) within sight of its substrates hydrogen peroxide (H
291:) and Cl. There is five times more atheronal B that was created compare to atheronal A when cholesterol was incubated with hypochlorous corrosive (HOCl) and hydrogen peroxide. In any cases, in both the responses, immunoglobulin G (IgG) did not improve the arrangement of secosterols, recommending that singlet oxygen (O 315:
troposphere. Furthermore, such cholesterol oxidation items have been found in the brains of autopsy specimens from Alzheimer’s disease patients. The ozonolyzed cholesterol quickens amyloidogenesis in these patients. They may play a crucial job in the pathogenesis of atherosclerosis and neurodegenerative infections.
259:(ROS, for example, singlet oxygen, superoxide anion, hydroxyl radicals, and ozone). Atheronals, the major product of ozonolysis, when cholesterol is ozonized in the arrangement at high ozone fixations (>0.1%), are the substance that need be give extra care to since it have huge effect on the human body. 282:
that occur so smoothly in the biological system to produce atheronal B. Atheronal A and B were produced in an ozone-autonomous way using the Hock-cleavage of 5α-hydroperoxy cholesterol, which can emerge from the singlet oxygen ene reaction with cholesterol. However, atheronal B is shaped effectively
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When the ozonolysis of cholesterol reaction occurs, the atheronals as a product will quicken the normal conversion of monocytes to macrophages, are rapidly taken up by macrophages, hasten the inflammatory response on and increase the stickiness of the interior arterial walls, and contribute to the
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setting could lead to the recruitment, entrapment, dysfunction, and ultimate destruction of macrophages, with the major leukocyte player in inflammatory artery disease. Furthermore, atheronals have additionally been detected in lung tissue, potentially from exposure of lung surfactant to the
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Takeuchi, Cindy; Galvé, Roger; Nieva, Jorgé; Witter, Daniel; Wentworth, Anita; Troseth, Ryan; Lerner, Richard; Wentworth, Paul (17 May 2006). "Proatherogenic Effects of the Cholesterol Ozonolysis Products, Atheronal-A and Atheronal-B".
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Tomono, Susumu; Miyoshi, Noriyuki; Sato, K; Ohba, Y; Ohshima, H (29 May 2009). "Formation of cholesterol ozonolysis products through an ozone-free mechanism mediated by the myeloperoxidase-H2O2-chloride system".
240:. Atheronal A (secosterol A) is the major product of ozonolysis which is 3β-hydroxy-5-oxo-5,6-secocholestan-6-al. Atheronal B (secosterol B) is formed by the intramolecular 140: 367:
Tomono, Susumu; Miyoshi, Noriyuki; Hidemi, Shiokawa; Tomoe, Iwabuchi; Yasuaki, Aratani; Tatsuya, Higashi; Hiroshi, Oshima (January 2011).
217: 264: 369:"Formation of cholesterol ozonolysis products in vitro and in vivo through a myeloperoxidase-dependent pathway" 295:) and perhaps another oxidant, however not an ozone-like oxidant, intervened the development of secosterols. 255:, a alkene that are located in aspiratory surfactant, anticipated in the attack by ozone among the different 256: 53: 308:, the hardening of the arteries. Atheronals possess biological effects that if translated to an 477: 400: 349: 500: 469: 439: 431: 390: 380: 341: 168: 305: 505: 444: 419: 395: 368: 279: 241: 211: 494: 126: 118: 244:
of atheronal A, which is 3β-hydroxy-5β-hydroxy-B-norcholestane-6β-carboxaldehyde.
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Except where otherwise noted, data are given for materials in their
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In the mechanism, atheronal A are produces from a process called
420:"Environmental Disease: Ozone: Good, Bad, or Indifferent?" 59:
B: 3β-Hydroxy-5β-hydroxy-B-norcholestane-6β-carboxaldehyde
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B: C(CCCC(C)C)1CCC21(CCC3C2(4(3(CC(C4)O)C)O)C=O)C
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Biochemical and Biophysical Research Communications
148:A: C(CCCC(C)C)1CC21(CC(2CC=O)3(CC(CC3=O)O)C)C 125: 117: 8: 236:formed in the reaction of cholesterol with 304:formation of arterial plaques. This cause 268:Mechanism of the ozonolysis of cholesterol 57:A: 3β-Hydroxy-5-oxo-5,6-secocholestan-6-al 15: 443: 394: 384: 323: 145: 7: 299:Effects of atheronals in human body 278:. Next, the atheronal A go through 107: 418:Weinhold, Bob (1 September 2006). 14: 424:Environmental Health Perspectives 180: 35: 22: 214:(at 25 °C , 100 kPa). 186: 174: 1: 522: 474:10.1016/j.bbrc.2009.03.155 232:are biologically relevant 373:Journal of Lipid Research 248:Ozonolysis of cholesterol 208: 161: 136: 64: 52: 47: 34: 21: 257:reactive oxygen species 269: 436:10.1289/ehp.114-a522b 267: 386:10.1194/jlr.M006775 204: g·mol 18: 270: 218:Infobox references 16: 346:10.1021/bi0604330 340:(23): 7162–7170. 226:Chemical compound 224: 223: 93:Interactive image 85:Interactive image 513: 486: 485: 456: 450: 449: 447: 415: 409: 408: 398: 388: 364: 358: 357: 328: 203: 188: 182: 176: 169:Chemical formula 129: 121: 109: 95: 87: 39: 26: 19: 521: 520: 516: 515: 514: 512: 511: 510: 491: 490: 489: 458: 457: 453: 417: 416: 412: 366: 365: 361: 330: 329: 325: 321: 306:atherosclerosis 301: 294: 290: 286: 250: 227: 220: 215: 201: 191: 185: 179: 171: 157: 154: 149: 144: 143: 132: 110: 98: 76: 60: 58: 43: 40: 30: 27: 12: 11: 5: 519: 517: 509: 508: 503: 493: 492: 488: 487: 451: 410: 359: 322: 320: 317: 300: 297: 292: 288: 284: 280:aldol reaction 272: 271: 249: 246: 242:aldol reaction 225: 222: 221: 216: 212:standard state 209: 206: 205: 199: 193: 192: 189: 183: 177: 172: 167: 164: 163: 159: 158: 156: 155: 152: 150: 147: 139: 138: 137: 134: 133: 131: 130: 122: 113: 111: 103: 100: 99: 97: 96: 88: 79: 77: 70: 67: 66: 62: 61: 56: 50: 49: 45: 44: 41: 32: 31: 28: 13: 10: 9: 6: 4: 3: 2: 518: 507: 504: 502: 499: 498: 496: 483: 479: 475: 471: 467: 463: 455: 452: 446: 441: 437: 433: 429: 425: 421: 414: 411: 406: 402: 397: 392: 387: 382: 378: 374: 370: 363: 360: 355: 351: 347: 343: 339: 335: 327: 324: 318: 316: 313: 312: 307: 298: 296: 281: 277: 266: 262: 261: 260: 258: 254: 247: 245: 243: 239: 235: 231: 219: 213: 207: 200: 198: 195: 194: 173: 170: 166: 165: 160: 151: 146: 142: 135: 128: 123: 120: 115: 114: 112: 106: 102: 101: 94: 89: 86: 81: 80: 78: 74: 69: 68: 63: 55: 51: 46: 38: 33: 25: 20: 468:(2): 222–7. 465: 461: 454: 427: 423: 413: 379:(1): 87–97. 376: 372: 362: 337: 334:Biochemistry 333: 326: 309: 302: 273: 251: 229: 228: 65:Identifiers 430:(9): A522. 253:Cholesterol 162:Properties 54:IUPAC names 42:Atheronal B 29:Atheronal A 17:Atheronals 495:Categories 319:References 276:ozonolysis 234:oxysterols 230:Atheronals 197:Molar mass 71:3D model ( 482:19345674 405:20921334 354:16752907 127:24779591 124:B: 116:A: 90:B: 82:A: 501:Sterols 445:1570068 396:2999934 311:in vivo 202:418.662 119:6398884 105:PubChem 480:  442:  403:  393:  352:  141:SMILES 48:Names 506:Ozone 238:ozone 73:JSmol 478:PMID 401:PMID 350:PMID 470:doi 466:383 440:PMC 432:doi 428:114 391:PMC 381:doi 342:doi 108:CID 497:: 476:. 464:. 438:. 426:. 422:. 399:. 389:. 377:52 375:. 371:. 348:. 338:45 336:. 184:46 178:27 484:. 472:: 448:. 434:: 407:. 383:: 356:. 344:: 293:2 289:2 287:O 285:2 190:3 187:O 181:H 175:C 75:)

Index



IUPAC names
JSmol
Interactive image
Interactive image
PubChem
6398884
24779591
SMILES
Chemical formula
Molar mass
standard state
Infobox references
oxysterols
ozone
aldol reaction
Cholesterol
reactive oxygen species

ozonolysis
aldol reaction
atherosclerosis
in vivo
doi
10.1021/bi0604330
PMID
16752907
"Formation of cholesterol ozonolysis products in vitro and in vivo through a myeloperoxidase-dependent pathway"
doi

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