Piper sarmentosum Roxb. (Piperaceae) is a traditional medicinal plant in South-East Asian countries. The chemical investigation of leaves from this species resulted in the isolation of three previously not described compounds, namely 4″-(3-hydroxy-3-methylglutaroyl)-2″-β-D-glucopyranosyl vitexin (1), kadukoside (2), and 6-O-trans-p-coumaroyl-D-glucono-1,4-lactone (3), together with 31 known compounds. Of these known compounds, 21 compounds were isolated for the first time from P. sarmentosum. The structures were established by 1D and 2D NMR techniques and HR-ESI-MS analyses. The compounds were evaluated for their anthelmintic (Caenorhabditis elegans), antifungal (Botrytis cinerea, Septoria tritici and Phytophthora infestans), antibacterial (Aliivibrio fischeri) and cytotoxic (PC-3 and HT-29 human cancer cells lines) activities. Methyl-3-(4-methoxyphenyl)propionate (8), isoasarone (12), and trans-asarone (15) demonstrated anthelmintic activity with IC50 values between 0.9 and 2.04 mM. Kadukoside (2) was most active against S. tritici with IC50 at 5.0 µM and also induced 94% inhibition of P. infestans growth at 125 µM. Trans-asarone (15), piperolactam A (23), and dehydroformouregine (24) displayed a dose-dependent effect against B. cinerea from 1.5 to 125 µM up to more than 80% inhibition. Paprazine (19), cepharadione A (21) and piperolactam A (23) inhibited bacterial growth by more than 85% at 100 µM. Only mild cytotoxic effects were observed.

中文翻译：

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从 Piper sarmentosum Roxb 中分离的次级代谢物的表征和生物活性潜力。

荸荠 Roxb. （胡椒科）是东南亚国家的传统药用植物。对该物种叶子的化学研究导致分离出三种以前未描述的化合物，即 4″-(3-hydroxy-3-methylglutaroyl)-2″-β-D-glucopyranosyl vitexin (1)，kadukoside (2)和 6-O-trans-p-coumaroyl-D-glucono-1,4-lactone (3)，以及 31 种已知化合物。在这些已知化合物中，有21种化合物为首次从垂叶松中分离得到。这些结构是通过 1D 和 2D NMR 技术以及 HR-ESI-MS 分析确定的。评估了这些化合物的驱虫药（秀丽隐杆线虫）、抗真菌药（灰葡萄孢菌、小麦壳孢菌和致病疫霉）、抗菌药（Aliivibrio fischeri）和细胞毒药（PC-3 和 HT-29 人类癌细胞系）活性。Methyl-3-(4-methoxyphenyl)propionate (8)、isoasarone (12) 和 trans-asarone (15) 表现出驱虫活性，IC50 值在 0.9 和 2.04 mM 之间。Kadukoside (2) 对小麦链霉菌最有效，IC50 为 5.0 µM，并且在 125 µM 时还诱导了 94% 的致病疫霉生长抑制。反式细辛醚 (15)、哌内酰胺 A (23) 和脱氢甲酰脲 (24) 在 1.5 至 125 µM 范围内对灰霉病菌表现出剂量依赖性作用，抑制率高达 80% 以上。Paprazine (19)、头孢拉酮 A (21) 和哌内酰胺 A (23) 在 100 µM 时抑制细菌生长超过 85%。仅观察到轻微的细胞毒性作用。0 µM 并且在 125 µM 时还诱导了 94% 的致病疫霉生长抑制。反式细辛醚 (15)、哌内酰胺 A (23) 和脱氢甲酰脲 (24) 在 1.5 至 125 µM 范围内对灰霉病菌表现出剂量依赖性作用，抑制率高达 80% 以上。Paprazine (19)、头孢拉酮 A (21) 和哌内酰胺 A (23) 在 100 µM 时抑制细菌生长超过 85%。仅观察到轻微的细胞毒性作用。0 µM 并且在 125 µM 时还诱导了 94% 的致病疫霉生长抑制。反式细辛醚 (15)、哌内酰胺 A (23) 和脱氢甲酰脲 (24) 在 1.5 至 125 µM 范围内对灰霉病菌表现出剂量依赖性作用，抑制率高达 80% 以上。Paprazine (19)、头孢拉酮 A (21) 和哌内酰胺 A (23) 在 100 µM 时抑制细菌生长超过 85%。仅观察到轻微的细胞毒性作用。