Pyripyropenes, Novel Inhibitors of Acyl‐CoA: Cholesterol Acyltransferase Produced by Aspergillus fumigatus. Part 2. Structure Elucidation of Pyripyropenes A, B, C and D.
Pyripyropenes, Novel Inhibitors of Acyl‐CoA: Cholesterol Acyltransferase Produced by Aspergillus fumigatus. Part 2. Structure Elucidation of Pyripyropenes A, B, C and D.
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Pyripyropenes，酰基辅酶 A 的新型抑制剂：烟曲霉产生的胆固醇酰基转移酶，第 2 部分。 Pyripyropenes A、B、C 和 D 的结构阐明。
DOI：
10.1002/chin.199432220
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发表时间：
1994
期刊：
影响因子：
--
通讯作者：
S. Ōmura
中科院分区：
文献类型：
--
作者：
Yong;H. Tomoda;H. Nishida;T. Sunazuka;R. Obata;S. Ōmura
新型酰基辅酶A：胆固醇酰基转移酶（ACAT）抑制剂pyripyropenes A， B， c和D的结构主要通过波谱研究包括各种核磁共振测量来确定。吡苯醚具有由吡啶、a-吡酮和倍半萜组成的共同结构。由烟曲霉FO-1289产生的pyripypypenes的三倍半萜部分的三个o -乙酰基残基中的一个被pyripypenes B、c和d中的0-丙烯基残基取代，是非常有效的酰基辅酶a：胆固醇酰基转移酶（ACAT） X的抑制剂。本文对其产生菌的分类、发酵、分离及生物学特性进行了综述。本文将报道A、B、c和D的结构解析。A、B、c和D的理化性质。pyripypypenes的理化性质如表1所示。采用高分辨电子冲击质谱（HREI-MS）和快速原子轰击质谱（FAB-MS）测定了A、B、C、D的分子式分别为C31H37NO10和c32h39no10。pyripypypenes在MeOH中的uvmax分别为231 nm （e 24,300）和320nm （e 13,400）。红外光谱表明，吡咯烯类化合物存在- oh （3550cm”1）和co - o -（1740和172cm”1）残基。吡咯烯A的结构
The structures of pyripyropenes A, B, Cand D, novel acyl-CoA: cholesterol acyltransferase (ACAT) inhibitors, were determined mainly byspectroscopic studies including various NMR measurements. Pyripyropeneshave a commonstructure whichconsists of pyridine, a-pyrone and sesquiterpene moieties. Oneof the three O-acetyl residues in the sesquiterpene moiety of pyripyropene Ais replaced with an0-propionyl residue in pyripyropenes B, Cand D.Pyripyropenes produced by Aspergillusfumigatus FO-1289 were very potent inhibitors of acyl-CoA: cholesterol acyltransferase (ACAT) X). The taxonomy of the producing organism, fermentation, isolation and biological properties of pyripyropenes have been described in the preceding paper2). Wewill report herein the structure elucidation of pyripyropenes A, B, Cand D. Physico-chemical Properties of Pyripyropenes A, B, Cand D Pyripyropenes A, B, Cand Dwere isolated as white powders. The physico-chemical properties of pyripyropenes are summarized in Table 1. The molecular formulas were determined to be C31H37NO10 for pyripyropene A and C32H39NO10for pyripyropenes B, C and D by high resolution electron impact mass (HREI-MS) and fast atom bombardment mass spectra (FAB-MS). Pyripyropenes showed the same UVmaximaat 231 (e 24,300) and 320nm (e 13,400) in MeOH. The IR spectra ofpyripyropenes suggested the presence of-OH (3550cm" 1) and-CO-O-(1740 and 1702cm" 1) residues. Structure of Pyripyropene A