CN114177167B - 一种倍半萜内酯化合物的新用途 - Google Patents
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- -1 sesquiterpene lactone compound Chemical class 0.000 title claims abstract description 10
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- QAQCPAHQVOKALN-RMEBNNNOSA-N guaiane Chemical compound C1[C@H](C(C)C)CC[C@H](C)[C@@H]2CC[C@H](C)[C@@H]21 QAQCPAHQVOKALN-RMEBNNNOSA-N 0.000 description 2
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- NTNWOCRCBQPEKQ-UHFFFAOYSA-N NG-mono-methyl-L-arginine Natural products CN=C(N)NCCCC(N)C(O)=O NTNWOCRCBQPEKQ-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 102000011779 Nitric Oxide Synthase Type II Human genes 0.000 description 1
- 108010076864 Nitric Oxide Synthase Type II Proteins 0.000 description 1
- 102100029438 Nitric oxide synthase, inducible Human genes 0.000 description 1
- 101710089543 Nitric oxide synthase, inducible Proteins 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
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- CWVRJTMFETXNAD-JUHZACGLSA-N chlorogenic acid Chemical class O[C@@H]1[C@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-JUHZACGLSA-N 0.000 description 1
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- 229930001431 germacrane Natural products 0.000 description 1
- IBMAYSYTZAVZPY-QDMKHBRRSA-N germacrane Chemical compound CC(C)[C@H]1CC[C@@H](C)CCC[C@@H](C)CC1 IBMAYSYTZAVZPY-QDMKHBRRSA-N 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
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- 210000002865 immune cell Anatomy 0.000 description 1
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- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
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- 210000002540 macrophage Anatomy 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000027939 micturition Effects 0.000 description 1
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- 201000008383 nephritis Diseases 0.000 description 1
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
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- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- C07—ORGANIC CHEMISTRY
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Abstract
本发明公开了一种倍半萜内酯化合物的新用途。本发明开发了化合物cichoralexin在抗炎活性上的医药用途,同时拓展了抗炎药物的天然来源。
Description
技术领域
本发明涉及一种倍半萜内酯化合物的医药新用途。
背景技术
菊苣(Cichorium intybus L),又名蓝菊、苦苣,是菊科(Compositae)菊苣属(Cichorium)一年生或多年生草本植物,为传统的药食同源植物。菊苣味苦、性寒,具有清热解毒、健胃消食、利尿消肿之功效,民间用于治疗湿热黄疸、胃痛食少、肾炎水肿等病症。现代研究证实,菊苣具有降血糖、抗炎、抗肿瘤、抗氧化和抗高尿酸血症等多方面的药理活性。
至今为止从菊苣中报道的化合物约有100余种,涉及倍半萜内酯、黄酮、绿原酸衍生物、香豆素、三萜和甾体、多糖等多种结构类型,其中倍半萜内酯类化合物是菊苣的主要成分,也是其区别于其他蔬菜的独特苦味物质。目前从菊苣中报道的倍半萜内酯约60余种,主要包括愈创木烷型(Guaiane)、吉马烷型 (Germacrane)和桉烷型(Eudesmane)3种母核类型。
目前对于菊苣中倍半萜内酯化合物的研究大多集中在粗提物或者对单体化合物的纯化上,对其中具有抗炎活性成分的研究尚不全面。
发明内容
本发明对菊苣中具有抗炎活性的成分进一步进行了研究,拓展了倍半萜内酯的医药用途,也拓宽了抗炎活性药物的植物来源。
为了达到上述目的,本发明提供的技术方案如下:
一种倍半萜内酯化合物在制备具有抗炎活性药物方面的应用,该倍半萜内酯化合物的结构如下:
本发明提供了来源于菊苣内的一种倍半萜内酯化合物在抗炎方面的新用途,开发了化合物的医药新应用,同时拓展了抗炎药物的天然来源。
具体实施方式
下面结合具体实施例对本发明进行详细说明。
实施例1
化合物提取纯化
干燥的菊苣根于80%的乙醇溶液浸泡提取4次,每次7天,(也可回流提取,样品加10-15倍80%的乙醇,微沸回流提取3次,每次2小时)合并提取液,50℃下减压浓缩至无醇。粗提物以适量水混悬,依次以石油醚、乙酸乙酯和正丁醇萃取。石油醚萃取部位在40-50℃下减压浓缩至干燥,备用。
石油醚萃取部位以硅胶柱色谱进行柱层析划段,以二氯甲烷:甲醇(1:0→0: 1,v/v)溶剂系统洗脱,划为14个段Fr.P1-Fr.P14,其中Fr.P8再次经过硅胶柱层析,以二氯甲烷:甲醇(20:1→3:7,v/v)溶剂系统洗脱,之后再经过 RP-18反相色谱柱层析,以水:甲醇(6:4→0:1,v/v)为洗脱剂,经点板合并分别得到P8-1~P8-4。然后样品经制备液相纯化,合适浓度(等度)的乙腈/水洗脱制备,从P8-1中获得本发明化合物,经结构鉴定其为已知化合物cichoralexin,结构式如下:
实施例2
抗炎活性研究
一氧化氮(nitric oxide,NO)具有广泛而重要的生物学调控功能,在炎症、肿瘤及心血管系统等均有重要作用。当免疫细胞遭受微生物内毒素、炎症介质等刺激时,会生成大量的诱导型一氧化氮合成酶(induced NO synthase,iNOS),产生NO进行免疫应答,因此抑制NO生成是化合物抗炎活性的直接指标。将小鼠单核巨噬细胞RAW264.7用LPS脂多糖诱导一氧化氮合成酶的生成,同时加入待测化合物处理,吸取培养基通过Griess法在570nm波长测吸光值来检测亚硝酸盐(NO2-)。
将RAW264.7细胞接种至96孔板,用1μg/ml LPS进行诱导刺激,同时加入实施例1中获得的化合物cichoralexin(终浓度50μM)处理,设置不含药物组和L-NMMA阳性药物组做对照。细胞过夜培养后取培养基检测NO生成,在570 nm处测定吸光值。在剩余培养基中加入MTS进行细胞存活率检测,排除化合物对细胞的毒性影响。
NO生成抑制率(%)=(非药物处理组OD570nm-样品组OD570nm)/ 非药物处理组OD570nm×100%
IC50(半数抑制浓度)按Reed&Muench法计算。
结果显示,化合物cichoralexin,其半数抑制浓度(IC50)为17.68μM,具有显著的NO生成抑制活性,如下表所示。
表1化合物cichoralexin的NO生成抑制活性a。
aValues represent means±SD(n=3).bconcentration in μM required toinhibit 50% of NO production.cPositive control。
Claims (1)
1.一种倍半萜内酯化合物作为唯一活性成分在制备具有抗炎活性药物中的应用,该倍半萜内酯化合物的结构如下:
。
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Chemical Composition and Nutritive Benefits of Chicory (Cichorium intybus) as an Ideal Complementary and/or Alternative Livestock Feed Supplement;Ifeoma Chinyelu Nwafor等;《the Scientific World Journal》;第2017卷;1-11 * |
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