Antioxidant, Antimicrobial and Cytotoxic Activities of Amides and Aristolactams from Piper wallichii (Miq.) Hand.-Mazz. Stems

Pub Date : 2023-03-04 DOI:10.1080/22311866.2023.2211043

Nonthalert Lertnitikul, R. Suttisri, Supotchana Sitthigool, C. Pattamadilok, Kanyanat Piewpong, Ariya Khanboon, Jatupol Liangsakul, Cherdsak Boonyong

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引用次数: 1

Abstract

Abstract Four amides, namely, piperine (1), pellitorine (2), piperiline (5) and N-trans-p-coumaroyltyramine (7), and three aristolactams, i.e., piperolactams D (3), B (4) and A (6), were isolated from the methanol extract of Piper wallichii stems. Piperiline, piperolactams B and D were obtained from this plant for the first time. Compounds 1, 3, 5, 6 and 7 were evaluated for their antioxidant, antimicrobial and cytotoxic activities. Piperine (1) displayed the highest antioxidant activity in scavenging DPPH radicals with an IC50 value of 94.51 ± 11.91 μM. Piperolactams D (3) and A (6) showed antibacterial activity against Gram-positive bacteria (B. subtilis and S. aureus) with MICs of between 500-1000 μM. All test compounds were cytotoxic to breast cancer (MCF-7) cells, while the aristolactams were more toxic to colon cancer (Caco-2) cells than the amides. Compounds 1, 3, 6 and 7 were moderately cytotoxic to the doxorubicin-resistant MCF-7 subline (MCF-7/DOX). All compounds were non-toxic to normal human fibroblast (NIH/3T3) cells. GRAPHICAL ABSTRACT

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Piper wallichii（Miq.）Hand酰胺和内酰胺的抗氧化、抗菌和细胞毒性活性-马兹。茎

摘要从胡椒茎甲醇提取物中分离得到胡椒碱(1)、胡椒碱(2)、胡椒碱(5)和n -反式-对- coumaroyylyramine(7) 4种酰胺，以及马兜铃内酰胺D(3)、B(4)和A(6) 3种酰胺。胡椒内酰胺B和D为首次从该植物中分离得到。对化合物1、3、5、6和7的抗氧化、抗菌和细胞毒活性进行了评价。胡椒碱(1)对DPPH自由基的清除活性最高，IC50值为94.51±11.91 μM。辣椒内酰胺D(3)和A(6)对革兰氏阳性菌(枯草芽孢杆菌和金黄色葡萄球菌)的抑菌活性在500 ~ 1000 μM之间。所有测试化合物对乳腺癌(MCF-7)细胞都有细胞毒性，而马兜铃内酰胺对结肠癌(Caco-2)细胞的毒性比酰胺更大。化合物1、3、6和7对耐阿霉素MCF-7亚群(MCF-7/DOX)具有中等细胞毒性。所有化合物对正常人成纤维细胞(NIH/3T3)均无毒。图形抽象

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