On the structure and synthesis of neuroprotectin D1, a novel anti-inflammatory compound of the docosahexaenoic acid family

On the structure and synthesis of neuroprotectin D1, a novel anti-inflammatory compound of the docosahexaenoic acid family
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DOI:
10.1194/jlr.c500015-jlr200
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发表时间:
2005-11-01
影响因子:
6.5
通讯作者:
Butovich, IA
Butovich, IA
中科院分区:
生物学2区
文献类型:
--
作者:
Butovich, IA

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马铃薯块茎脂肪氧合酶可将17(S)-氢(佩罗)氧化二十二碳烯酸转化为10,17(S)-二氢(佩罗)二十二碳六烯酸-4Z,7 Z,11 E,13 Z,15 E,19 Z-烯酸[10,17(S)-diHDHA],后者显然是通过双重脂肪氧合机制形成的。在反应产物中未发现痕量的10,17(S)-二氢(佩罗)氧基六碳-4 Z,7 Z,11 E,13 E,15 Z,19 Z-烯酸。(sic)很有可能早期描述的“神经保护素D1”[或“10,17(S)二十二碳三烯”],一种衍生自二十二碳六烯酸的新型有效抗炎化合物,实际上是通过双重脂氧合机制而不是先前认为的环氧化/异构化机制形成的10,17(S)-二羟基二十二碳六-4Z,7Z,11 E,13 Z,15 E,19 Z-烯酸。内务部的布托维奇神经保护素D1的结构和合成,二十二碳六烯酸家族的新型抗炎化合物。
Potato tuber lipoxygenase was shown to convert 17(S)-hydro(pero)xydocasahaenoic acid in 10,17 (S)-dihydro (pero)sydocasahexa-4Z,7Z,11E,13Z,15E,19Z-enoic acid [10,17 (S)-diHDHA] which was formed apparently through a double lipoxygenation mechanism. No traces of 10,17 (S)-dihdro(pero)xydocasahexa-4Z,7Z,11E,13E,15Z,19Z-enoic acid were found among the reaction products. (sic) It is very likely that a described earlier "neuroprotectin D1" [or "10,17(S)docosatriene"], a novel and potent amti-inflammatory compound derived from docosahexaeonic acid, was, in fact, 10,17 (S)-dihydroxydocasahexa-4Z,7Z,11E,13Z,15E,19Z-enoic acid fromed through a double lipoxygenation mechanism instead of a previously thought epoxidation/ isomerization mechanism.-Butovich, I.A. On the structure and synthesis of neuroprotectin D1, a novel anti-inflammatory compound of the docosahexaenoic acid family.