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Targeted isolation of terpenoid indole alkaloids from Melodinus cochinchinensis (Lour.) Merr. using molecular networking and their biological activities
Industrial Crops and Products ( IF 5.6 ) Pub Date : 2020-09-16 , DOI: 10.1016/j.indcrop.2020.112922
Fangru Li , Yudan Wang , Shuyue He , Afsar Khan , Qingwang Xue , Qimin Cui , Lu Liu , Yaping Liu , Guiguang Cheng

Melodinus cochinchinensis (Lour.) Merr. has been used in Traditional Chinese Medicine for the management of various ailments, yet its chemical constituents are rarely studied. This study was aimed to isolate terpenoid indole alkaloids (TIAs) from the aerial parts of M. cochinchinensis by the guidance of ultrahigh-performance liquid chromatography coupled with a tandem mass spectrometry (UHPLC-MS/MS), and to elucidate their cytotoxic, immunosuppressive and anti-inflammatory activities. Eight new TIAs (1 and 5-11) along with 21 previously described analogues were isolated with the basis of molecular networking developed by our previously reported TIAs from the species of Melodinus. The structures of new TIAs were elucidated by the analysis of extensive spectroscopic data. Among the tested isolates, 11-methoxytabersonine (25) exhibited considerable cytotoxic activity against human acute lymphoblastic leukemia (MOLT-4), breast adenocarcinoma (MCF-7), pro-myeloid leukemia (HL-60), lung adenocarcinoma (A-549), and hepatocelluar carcinoma (SMMC-7721) cell lines, which was more effective than the positive control, cisplatin. The 19β-hydroxyvenalstonidine (21) displayed moderate immunosuppressive effect against Con A-induced splenocyte proliferation at 40 μM, while 16,17-dehydro-19S-vindolinine (1) showed potent inhibitory activity on nitric oxide (NO), interleukin-6 (IL-6), and tumor necrosis factor-α (TNF-α) expressions in LPS-induced RAW 264.7 macrophages.



中文翻译:

有针对性地从Melodinus cochinchinensis(Lour。)Merr。分离萜类吲哚生物碱。利用分子网络及其生物活性

Melodinus cochinchinensis(Lour。)Merr。中药已被用于各种疾病的治疗,但其化学成分很少研究。此研究的目的是分离萜类吲哚生物碱从地上部分(例TIA)M.门冬通过加上有串联质谱(UHPLC-MS / MS)超高性能液相色谱法的指导下,并阐明它们的细胞毒性,免疫抑制和消炎活性。八个新的TIA(15 - 11)与21个前面描述的类似物随着分子网络由我们先前报道的TIA从品种开发的基础上进行分离山橙属。通过分析大量光谱数据阐明了新TIA的结构。在测试的分离株中,11-甲氧tab草碱(25)对人急性淋巴细胞白血病(MOLT-4),乳腺腺癌(MCF-7),促髓性白血病(HL-60),肺腺癌(A-549)表现出相当大的细胞毒活性。 )和肝细胞癌(SMMC-7721)细胞系,它比阳性对照顺铂更有效。19 β -hydroxyvenalstonidine(21)显示对刀豆球蛋白A诱导的脾细胞增殖适度的免疫抑制作用在40μM,而16,17-脱氢-19小号-vindolinine(1)对LPS诱导的RAW 264.7巨噬细胞中的一氧化氮(NO),白介素6(IL-6)和肿瘤坏死因子-α(TNF- α)表达具有有效的抑制作用。

更新日期:2020-09-16
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