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Triterpenoids and steroids isolated from Anatolian Capparis ovata and their activity on the expression of inflammatory cytokines
Pharmaceutical Biology ( IF 3.8 ) Pub Date : 2020-01-01 , DOI: 10.1080/13880209.2020.1814356
Isil Gazioglu 1 , Sevcan Semen 2 , Ozden Ozgun Acar 3 , Ufuk Kolak 4 , Alaattin Sen 3, 5 , Gulacti Topcu 6
Affiliation  

Abstract Context Capparis L. (Capparaceae) is grown worldwide. Caper has been used in traditional medicine to treat various diseases including rheumatism, kidney, liver, stomach, as well as headache and toothache. Objective To isolate and elucidate of the secondary metabolites of the C. ovata extracts which are responsible for their anti-inflammatory activities. Materials and methods Buds, fruits, flowers, leaves and stems of C. ovata Desf. was dried, cut to pieces, then ground separately. From their dichloromethane/hexane (1:1) extracts, eight compounds were isolated and their structures were elucidated by NMR, mass spectroscopic techniques. The effects of compounds on the expression of inflammatory cytokines in SH-SY5Y cell lines were examined by qRT-PCR ranging from 4 to 96 µM. Cell viability was expressed as a percentage of the control, untreated cells. Results This is a first report on isolation of triterpenoids and steroids from C. ovata with anti-inflammatory activity. One new triterpenoid ester olean-12-en-3β,28-diol, 3β-pentacosanoate (1) and two new natural steroids 5α,6α-epoxycholestan-3β-ol (5) and 5β,6β-epoxycholestan-3β-ol (6) were elucidated besides known compounds; oleanolic acid (2), ursolic acid (3), β-sitosterol (4), stigmast-5,22-dien-3β-myristate (7) and bismethyl-octylphthalate (8). mRNA expression levels as EC10 of all the tested seven genes were decreased, particularly CXCL9 (19.36-fold), CXCL10 (8.14-fold), and TNF (18.69) by the treatment of 26 µM of compound 1 on SH-SY5Y cells. Discussion and conclusions Triterpenoids and steroids isolated from C. ovata were found to be moderate-strong anti-inflammatory compounds. Particularly, compounds 1 and 3 were found to be promising therapeutic agents in the treatment of inflammatory and autoimmune diseases.

中文翻译:

从 Anatolian Capparis ovata 中分离的三萜类化合物和类固醇及其对炎性细胞因子表达的活性

摘要背景 Capparis L. (Capparaceae) 在世界范围内种植。刺山柑已在传统医学中用于治疗各种疾病,包括风湿病、肾病、肝病、胃病以及头痛和牙痛。目的分离并阐明卵形核果提取物具有抗炎活性的次级代谢产物。材料和方法 C. ovata Desf 的芽、果实、花、叶和茎。晒干,切成块,然后单独研磨。从它们的二氯甲烷/己烷 (1:1) 提取物中分离出八种化合物,并通过 NMR、质谱技术阐明了它们的结构。通过 qRT-PCR 检测化合物对 SH-SY5Y 细胞系中炎性细胞因子表达的影响,范围从 4 到 96 µM。细胞活力表示为对照的百分比,未经处理的细胞。结果这是关于从C. ovata 中分离具有抗炎活性的三萜类化合物和类固醇的第一次报告。一种新的三萜酯 olean-12-en-3β,28-diol, 3β-pentacosanoate (1) 和两种新的天然类固醇 5α,6α-epoxycholestan-3β-ol (5) 和 5β,6β-epoxycholestan-3β-ol ( 6) 除已知化合物外,还阐明了;齐墩果酸 (2)、熊果酸 (3)、β-谷甾醇 (4)、stigmast-5,22-dien-3β-myristate (7) 和 bismethyl-octylphthalate (8)。通过在 SH-SY5Y 细胞上处理 26 µM 化合物 1,所有测试的 7 个基因的 mRNA 表达水平作为 EC10 降低,特别是 CXCL9(19.36 倍)、CXCL10(8.14 倍)和 TNF(18.69)。讨论和结论 从 C. ovata 中分离出的三萜类化合物和类固醇被发现是中等强度的抗炎化合物。特别,
更新日期:2020-01-01
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