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一种从智利植物三叉叶亚苏草(Azorella trifurcata (Gaertn) Pers.)中提取的罕见多环二萜类化合物。

An unusual mulinane diterpenoid from the Chilean plant Azorella trifurcata (Gaertn) Pers.

作者信息

Areche Carlos, Sepulveda Beatriz, San Martin Aurelio, Garcia-Beltrán Olimpo, Simirgiotis Mario, Cañete Alvaro

机构信息

Departamento de Química, Facultad de Ciencias, Universidad de Chile, Casilla 653, Santiago, Chile.

出版信息

Org Biomol Chem. 2014 Sep 7;12(33):6406-13. doi: 10.1039/c4ob00966e.

Abstract

Four new mulinane-type diterpenoids besides the known compounds mulin-11,13-dien-20-oic acid, 13α-hydroxyazorellane, 13β-hydroxyazorellane, mulinolic acid, azorellanol, and mulin-11,13-dien-18-acetoxy-16,20-dioic acid were isolated from the Chilean plant Azorella trifurcata. One of the new metabolites isolated, 7α-acetoxy-9-epi-13β-hydroxymulinane, possesses a new trans-syn-trans arrangement in a tricyclic ring system not previously encountered in nature. Among the mulinane diterpenoids isolated, mulin-11,13-dien-20-oic acid showed the gastroprotective effect on HCl-EtOH-induced gastric lesions in mice (ED50 = 55 mg kg(-1)). Regarding the mode of gastroprotective action for this active compound, its effect was reduced by pre-treatment of the mice with indomethacin and N-ethylmaleimide, suggesting that prostaglandins and sulfhydryl compounds are positively involved in the gastroprotective activity using this model.

摘要

除了已知化合物穆林-11,13-二烯-20-酸、13α-羟基氮杂瑞香烷、13β-羟基氮杂瑞香烷、穆林醇酸、氮杂瑞香醇和穆林-11,13-二烯-18-乙酰氧基-16,20-二酸外,还从智利植物三叉叶氮杂瑞香中分离出4种新的穆林烷型二萜类化合物。分离得到的一种新代谢产物7α-乙酰氧基-9-表-13β-羟基穆林烷,在一个天然中未曾见过的三环系统中具有一种新的反-顺-反排列。在分离得到的穆林烷二萜类化合物中,穆林-11,13-二烯-20-酸对盐酸-乙醇诱导的小鼠胃损伤具有胃保护作用(半数有效剂量=55毫克/千克)。关于这种活性化合物的胃保护作用方式,用吲哚美辛和N-乙基马来酰亚胺对小鼠进行预处理可降低其作用效果,这表明前列腺素和巯基化合物在使用该模型的胃保护活性中起积极作用。

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