胡椒属植物中异戊烯基苯甲酸衍生物的抗寄生虫活性
Antiparasitic activity of prenylated benzoic acid derivatives from Piper species.
作者信息
Flores Ninoska, Jiménez Ignacio A, Giménez Alberto, Ruiz Grace, Gutiérrez David, Bourdy Genevieve, Bazzocchi Isabel L
机构信息
Instituto Universitario de Bio-Orgánica Antonio González, Universidad de La Laguna, Avda. Astrofísico, Francisco Sánchez 2, La Laguna, 38206 Tenerife, Canary Islands, Spain.
出版信息
Phytochemistry. 2009 Mar;70(5):621-7. doi: 10.1016/j.phytochem.2009.03.010. Epub 2009 Apr 8.
Fractionation of dichloromethane extracts from the leaves of Piper heterophyllum and P. aduncum afforded three prenylated hydroxybenzoic acids, 3-[(2E,6E,10E)-11-carboxy-3,7,15-trimethyl-2,6,10,14-hexadecatetraenyl)-4,5-dihydroxybenzoic acid, 3-[(2E,6E,10E)-11-carboxy-13-hydroxy-3,7,15-trimethyl-2,6,10,14-hexadecatetraenyl]-4,5-dihydroxybenzoic acid and 3-[(2E,6E,10E)-11-carboxy-14-hydroxy-3,7,15-trimethyl-2,6,10,15-hexadecatetraenyl]-4,5-dihydroxybenzoic acid, along with the known compounds, 4,5-dihydroxy-3-(E,E,E-11-formyl-3,7,15-trimethyl-hexadeca-2,6,10,14-tetraenyl)benzoic acid (arieianal), 3,4-dihydroxy-5-(E,E,E-3,7,11,15-tetramethyl-hexadeca-2,6,10,14-tetraenyl)benzoic acid, 4-hydroxy-3-(E,E,E-3,7,11,15-tetramethyl-hexadeca-2,6,10,14-tetraenyl)benzoic acid, 3-(3,7-dimethyl-2,6-octadienyl)-4-methoxy-benzoic acid, 4-hydroxy-3-(3,7-dimethyl-2,6-octadienyl)benzoic acid and 4-hydroxy-3-(3-methyl-1-oxo-2-butenyl)-5-(3-methyl-2-butenyl)benzoic acid. Their structures were elucidated on the basis of spectroscopic data, including homo- and heteronuclear correlation NMR experiments (COSY, HSQC and HMBC) and comparison with data reported in the literature. Riguera ester reactions and optical rotation measurements established the compounds as racemates. The antiparasitic activity of the compounds were tested against three strains of Leishmania spp., Trypanosoma cruzi and Plasmodium falciparum. The results showed that 3-(3,7-dimethyl-2,6-octadienyl)-4-methoxy-benzoic acid exhibited potent and selective activity against L. braziliensis (IC(50) 6.5 microg/ml), higher that pentamidine used as control. Moreover, 3-[(2E,6E,10E)-11-carboxy-3,7,15-trimethyl- 2,6,10,14-hexadecatetraenyl)-4,5-dihydroxybenzoic acid and 4-hydroxy-3-(3-methyl-1-oxo-2-butenyl)-5-(3-methyl-2-butenyl)benzoic acid showed moderate antiplasmodial (IC(50) 3.2 microg/ml) and trypanocidal (16.5 microg/ml) activities, respectively.
对胡椒属异叶胡椒和蒌叶胡椒叶片的二氯甲烷提取物进行分馏，得到了三种异戊烯基化羟基苯甲酸，即3 - [(2E,6E,10E)-11 - 羧基 - 3,7,15 - 三甲基 - 2,6,10,14 - 十六碳四烯基]-4,5 - 二羟基苯甲酸、3 - [(2E,6E,10E)-11 - 羧基 - 13 - 羟基 - 3,7,15 - 三甲基 - 2,6,10,14 - 十六碳四烯基]-4,5 - 二羟基苯甲酸和3 - [(2E,6E,10E)-11 - 羧基 - 14 - 羟基 - 3,7,15 - 三甲基 - 2,6,10,15 - 十六碳四烯基]-4,5 - 二羟基苯甲酸，以及已知化合物4,5 - 二羟基 - 3 - (E,E,E - 11 - 甲酰基 - 3,7,15 - 三甲基 - 十六碳 - 2,6,10,14 - 四烯基)苯甲酸（阿里安醛）、3,4 - 二羟基 - 5 - (E,E,E - 3,7,11,15 - 四甲基 - 十六碳 - 2,6,10,14 - 四烯基)苯甲酸、4 - 羟基 - 3 - (E,E,E - 3,7,11,15 - 四甲基 - 十六碳 - 2,6,10,14 - 四烯基)苯甲酸,3 - (3,7 - 二甲基 - 2,6 - 辛二烯基)-4 - 甲氧基 - 苯甲酸、4 - 羟基 - 3 - (3,7 - 二甲基 - 2,6 - 辛二烯基)苯甲酸和4 - 羟基 - 3 - (3 - 甲基 - 1 - 氧代 - 2 - 丁烯基)-5 - (3 - 甲基 - 2 - 丁烯基)苯甲酸。基于光谱数据，包括同核和异核相关核磁共振实验（COSY、HSQC和HMBC）以及与文献报道数据的比较，阐明了它们的结构。里格拉酯反应和旋光测量确定这些化合物为外消旋体。测试了这些化合物对三种利什曼原虫属、克氏锥虫和恶性疟原虫菌株的抗寄生虫活性。结果表明，3 - (3,7 - 二甲基 - 2,6 - 辛二烯基)-4 - 甲氧基 - 苯甲酸对巴西利什曼原虫表现出强效且选择性的活性（IC(50) 6.5微克/毫升），高于用作对照的喷他脒。此外，3 - [(2E,6E,10E)-11 - 羧基 - 3,7,15 - 三甲基 - 2,6,10,14 - 十六碳四烯基)-4,5 - 二羟基苯甲酸和4 - 羟基 - 3 - (3 - 甲基 - 1 - 氧代 - 2 - 丁烯基)-5 - (3 - 甲基 - 2 - 丁烯基)苯甲酸分别显示出中等的抗疟活性（IC(50) 3.2微克/毫升）和杀锥虫活性（16.5微克/毫升）。
Zotero 插件