A series of novel ricinoleic acid based lipoamino acid derivatives were synthesized from (Z)-methyl-12-aminooctadec-9-enoate and different l-amino acids (glycine, alanine, phenyl alanine, valine, leucine, isoleucine, proline and tryptophan). The structures of all the prepared compounds were characterized by ¹H NMR, ¹³C NMR and mass spectral studies. The title compounds were evaluated for their antimicrobial and anti-biofilm activities. Among all the derivatives, compound 7a (Z)-methyl-12-(2-aminoacetamido)octadec-9-enoate exhibited promising antibacterial activity (MIC, 3.9–7.8μg/mL) and compounds 7b (Z)-methyl 12-(2-aminopropanamido)octadec-9-enoate and 7g (Z)-methyl-12-(pyrrolidine-2-carboxamido)octadec-9-enoate exhibited moderate activity (MIC, 7.8–31.2μg/mL) selectively against four different Gram-positive bacterial strains such as Staphylococcus aureus MTCC 96, Bacillus subtilis MTCC 121, S. aureus MLS-16 MTCC 2940, Micrococcus luteus MTCC 2470. These compounds also exhibited excellent antifungal activity against studied fungal strains. Further, the compounds 7a, 7b and 7g were also screened for anti-biofilm activity. Among these lipoamino acid derivatives, compound 7a exhibited good anti-biofilm activity (IC₅₀, 1.9–4.1μg/mL) against four Gram-positive bacterial strains.

中文翻译：

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蓖麻油酸脂氨基酸衍生物的合成及生物学评价

从（Z）-甲基-12-氨基十八烷基-9-烯酸酯和不同的I-氨基酸（甘氨酸，丙氨酸，苯基丙氨酸，缬氨酸，亮氨酸，异亮氨酸，脯氨酸和色氨酸）合成了一系列基于蓖麻油酸的脂氨基酸衍生物。 。所有制备的化合物的结构均通过¹ H NMR表征，¹³13 C NMR和质谱研究。评价标题化合物的抗微生物和抗生物膜活性。在所有衍生物中，化合物7a（Z）-甲基-12-（2-氨基乙酰胺基）octadec-9-烯酸酯显示出有希望的抗菌活性（MIC，3.9–7.8μg / mL）和化合物7b（Z）-甲基12-（ 2-氨基丙酰胺基）octadec-9-烯酸酯和7g（Z）-甲基-12-（吡咯烷-2-甲酰胺基）octadec-9-烯酸酯对四种不同的革兰氏选择性药物具有中等活性（MIC，7.8-31.2μg/ mL）。阳性细菌菌株，如金黄色葡萄球菌MTCC 96，枯草芽孢杆菌MTCC 121，金黄色葡萄球菌MLS-16 MTCC 2940，黄球菌微球菌MTCC2470。这些化合物还对所研究的真菌菌株表现出出色的抗真菌活性。此外，还对化合物7a，7b和7g的抗生物膜活性进行了筛选。₅₀，1.9-4.1μg/ mL）的对四名革兰氏阳性细菌菌株。