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从叉枝鸦葱地上部分分离得到的两种新型具有生物活性的硫酸愈创木烷倍半萜盐生物碱。

Two novel bioactive sulfated guaiane sesquiterpenoid salt alkaloids from the aerial parts of Scorzonera divaricata.

作者信息

Wu Quan-Xiang, He Xiao-Feng, Jiang Chun-Xiao, Zhang Wei, Shi Zhuan-Ning, Li Hong-Fang, Zhu Ying

机构信息

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, PR China.

Department of Physiology, College of Basic Medicine, Lanzhou University, Lanzhou 730000, PR China; Key Laboratory of Pre-clinical Study for New Drugs of Gansu Province, Lanzhou 730000, PR China.

出版信息

Fitoterapia. 2018 Jan;124:113-119. doi: 10.1016/j.fitote.2017.10.011. Epub 2017 Oct 21.

DOI:10.1016/j.fitote.2017.10.011
PMID:29066296
Abstract

UNLABELLED

Extracts of the aerial parts of Scorzonera divaricata afforded sulfoscorzonin D (1) and sulfoscorzonin E (2), two novel pyrrolidine inner salt alkaloids with a sulfated guaiane sesquiterpene lactone nucleus, along with 22 known compounds. Especially, sulfoscorzonin D containing a unusual monoterpene moiety is very rare. The structures of new compounds were established using spectroscopic analysis including one- and two-dimensional NMR and HRESIMS. The cytotoxicities of compounds 1-4 and 10 against three tumor cell lines (K562, Hela, and HepG2) were evaluated using the MTT assay. Compounds 2 and 10 exhibited moderate cytotoxic activity. The biological properties of 1-3, 5-8, 10-14, and 16-24, were screened against nine different gram-positive and gram-negative bacteria. Compounds 1, 5-8, 10, and 18, showed potent antibacterial activities.

CHEMICAL COMPOUNDS STUDIED IN THIS ARTICLE

Glucozaluzanin C (PubChem CID: 442320); 1β,4α-dihydroxy-5α,6β,7α,11βH-eudermn-12; 6-olide (CID: 11119093); oleanolic acid (CID: 10494); lup-20(29)-ene-3β,28-diol (CID: 72326); (22E)-5α,8α-epidioxyergosta-6,22-dien-3β-ol (CID: 5469431); ergosta-3β,5α, 6β-trialcohol (CID: 44558918); stigma-5-en-3-O-β-glucoside (CID: 5742590); vomifoliol (CID: 12444927); trans-caffeic acid (CID: 689043); trans-p-hydroxy coumaric acid (CID: 637542); 4-hydroxy-3-methoxyphenyl ferulate (CID: 11500646); 7,3',4'-trihydroxyflavonol (CID: 5281614); tricin (ID: 5281702); luteolin (CID: 5280445); diosmetin (CID: 5281612); 5,7-dihydroxy-8-methoxyflavone (CID: 5281703); 5,7-dihydroxy-6-methoxyflavone (CID: 5320315); methyl-3,4-dihydroxy benzoate (CID: 287064); m-hydroxy benzoic acid (CID: 7420); 7-hydroxy-coumarin (CID: 5281426); and scopoletin (CID: 5280460).

摘要

未标注

叉枝鸦葱地上部分的提取物得到了硫代鸦葱宁D(1)和硫代鸦葱宁E(2),这两种新型吡咯烷内盐生物碱具有硫酸化愈创木烷倍半萜内酯核,还得到了22种已知化合物。特别地,含有不寻常单萜部分的硫代鸦葱宁D非常罕见。通过包括一维和二维核磁共振以及高分辨电喷雾电离质谱在内的光谱分析确定了新化合物的结构。使用MTT法评估了化合物1 - 4和10对三种肿瘤细胞系(K562、Hela和HepG2)的细胞毒性。化合物2和10表现出中等细胞毒性活性。针对九种不同的革兰氏阳性和革兰氏阴性细菌筛选了化合物1 - 3、5 - 8、10 - 14以及16 - 24的生物学特性。化合物1、5 - 8、10和18表现出强效抗菌活性。

本文研究的化学化合物

葡糖芦扎宁C(PubChem CID:442320);1β,4α - 二羟基 - 5α,6β,7α,11βH - 桉叶 - 12;6 - 内酯(CID:11119093);齐墩果酸(CID:10494);羽扇 - 20(29) - 烯 - 3β,28 - 二醇(CID:72326);(22E) - 5α,8α - 环氧麦角甾 - 6,22 - 二烯 - 3β - 醇(CID:5469431);麦角甾 - 3β,5α,6β - 三醇(CID:44558918);柱头 - 5 - 烯 - 3 - O - β - 葡萄糖苷(CID:5742590);紫黄质(CID:12444927);反式咖啡酸(CID:689043);反式对羟基香豆酸(CID:637542);4 - 羟基 - 3 - 甲氧基苯基阿魏酸(CID:11500646);7,·',4' - 三羟基黄酮醇(CID:5281614);小麦黄素(ID:5281702);木犀草素(CID:5280445);香叶木素(CID:5281612);5,7 - 二羟基 - 8 - 甲氧基黄酮(CID:5281703);5,7 - 二羟基 - 6 - 甲氧基黄酮(CID:5320315);3,4 - 二羟基苯甲酸甲酯(CID:287064);间羟基苯甲酸(CID:7420);7 - 羟基香豆素(CID:5281426);以及东莨菪素(CID:5280460)。

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