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Revisiting the absolute chirality and polymorphism of (-)-Istanbulin A.
Acta Crystallographica Section C ( IF 0.8 ) Pub Date : 2020-08-28 , DOI: 10.1107/s2053229620011493
Luz Arancibia 1 , Mariana Naspi 1 , Graciela Pucci 2 , Maricel Rodriguez 3 , Florencia Di Salvo 3
Affiliation  

The terpenoid (−)‐Istanbulin A is a natural product isolated from Senecio filaginoides DC, one of the 270 species of Senecio (Asteraceae) which occurs in Argentina. The structure and absolute configuration of this compound [9a‐hydroxy‐3,4a,5‐trimethyl‐4a,6,7,8a,9,9a‐hexahydro‐4H,5H‐naphtho[2,3‐b]‐furan‐2,8‐dione or (4S,5R,8R,10S)‐1‐oxo‐8β‐hydroxy‐10βH‐eremophil‐7(11)‐en‐12,8β‐olide, C15H20O4] were determined by single‐crystal X‐ray diffraction studies. It proved to be a sesquiterpene lactone showing an eremophilanolide skeleton whose chirality is described as 4S,5R,8R,10S. Structural results were also in agreement with the one‐ and two‐dimensional (1D and 2D) NMR and HR–ESI–MS data, and other complementary spectroscopic information. In addition, (−)‐Istanbulin A is a polymorph of the previously reported form of (−)‐Istanbulin A, form I; thus, the title compound is denoted form II or polymorph II. Structural data and a literature search allowed the chirality of Istanbulin A to be revisited. The antimicrobial and antifungal activities of (−)‐Istanbulin A, form II, were evaluated in order to establish a reference for future comparisons and applications related to specific crystal forms of Istanbulins.

中文翻译:

再谈(-)-伊斯坦布尔bulin A的绝对手性和多态性。

萜类化合物(-)-伊斯坦布林A是从千里光(Senecio filaginoides DC)分离的天然产物,千里光(Senecio filaginoides DC )是发生在阿根廷的千里光(菊科)270种之一。该化合物的结构和绝对构型[9a-hydroxy-3,4a,5-trimethyl-4-a,6,7,8a,9,9a-hexahydro-4 H,5 H-萘[2,3- b ]-呋喃-2,8-二酮或(4小号,5 - [R,8 - [R,10小号)-1-氧代8β羟基10β ħ -eremophil-7(11) -烯12,8β内酯,C 1520 O 4]由单晶X射线衍射研究确定。证明是倍半萜烯内酯,显示具有手性的四氢呋喃内酯骨架,描述为4 S,5 R,8 R,10 S。结构结果也与一维和二维(1D和2D)NMR和HR-ESI-MS数据以及其他互补光谱信息相符。另外,(-)-伊斯坦布尔蛋白A是先前报道的(-)-伊斯坦布尔蛋白A形式I的多晶型物;因此,标题化合物表示为II型或多晶型物II。通过结构数据和文献检索,可以重新研究Istanbulin A的手性。评估了(-)-Istanbulin A(II型)的抗微生物和抗真菌活性,以便为以后与伊斯坦布尔蛋白特定晶型相关的比较和应用提供参考。
更新日期:2020-08-28
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