摘要
目的研究药用昆虫凹纹胡蜂Vespa velutina auraria的化学成分及其抗炎活性。方法采用硅胶柱色谱、Sephadex LH-20凝胶和半制备高效液相等色谱技术进行分离纯化,通过核磁共振技术对化合物的结构进行表征和解析。以脂多糖(lipopolysaccharide,LPS)联合γ干扰素(interferon-γ,IFN-γ)诱导小鼠巨噬细胞RAW264.7作为炎症模型,探讨提取物及单体对炎症因子mRNA表达的影响。结果从凹纹胡蜂醋酸乙酯部位分离鉴定了16个化合物,分别为邻苯二酚(1)、对羟基苯甲醛(2)、对羟基苯丙酸甲酯(3)、4-羟基苯醋酸乙酯(4)、3,4-二羟基苯乙醇(5)、3,4-二羟基苯酰乙醇(6)、3,4-二羟基苯甲酸(7)、N-乙酰基-2-乙氧基-2-(3,4-二羟基苯基)乙胺(8)、2-(2-羟基丙酰氧基)丙酸甲酯(9)、对甲氧基苯甲醇(10)、3,4-二羟基苯甲酸甲酯(11)、α-乙基葡萄糖苷(12)、2-羟基-3-苯基丙酸甲酯(13)、N-乙酰基-2-(3,4-二羟基苯基)乙胺(14)、对甲基苯乙醇(15)和胸腺嘧啶(16)。凹纹胡蜂醇提物及提取物醋酸乙酯部位、正丁醇部位和水部位在300μg/mL时均能有效减少由LPS联合IFN-γ诱导RAW264.7细胞炎症因子一氧化氮合酶(inducible nitric oxide synthase,iNOS)基因相对表达量;化合物2、3、5、6、9~11对LPS联合IFN-γ诱导RAW264.7细胞肿瘤坏死因子-α(tumor necrosis factor-α,TNF-α)m RNA表达有抑制作用(P<0.01)。结论凹纹胡蜂醇提物及不同极性部位能降低炎症细胞中iNOS的表达,具有一定的抗炎作用。化合物1~16均为首次从凹纹胡蜂分离鉴定,其中2、3、5、6、9~11可能为潜在的活性单体。
Objective To study the chemical constituents and anti-inflammatory activities of medicinal insect Vespa velutina auraria.Methods The compounds were isolated and purified by silica gel,Sephadex LH-20 and semi-preparative liquid chromatography,while the structures of compounds were characterized and analyzed by nuclear magnetic resonance(NMR)technique.The mouse macrophage RAW264.7 inflammation model was induced by lipopolysaccharide(LPS)combined with interferon γ(IFN-γ),the effects of extracts and monomers on the mRNA expression of inflammatory factors were investigated.Results A total of 16 compounds were isolated from ethyl acetate fractions and identified as catechol hydroquinone(1),4-hydroxybenzaldehyde(2),methyl 3-(4-hydroxyphenyl)propionate(3),4-hydroxyphenethy acetate(4),3,4-dihydroxy-phenethyl alcohol(5),3,4-dihydroxyphenyl ethanol ketone(6),3,4-dihydroxy-benzoic acid(7),divesamides A(8),methyl-2-(2-hydroxy-propionyloxy)propionate(9),4-methoxybenzyl alcohol(10),3,4-dihydroxy-benzoic methyl ester(11),α-ethyl glucoside(12),papuline(13),N-acetyl-dopamine(14),2-(4-methylphenyl)ethanol(15),thymine(16).The alcohol extracts,ethyl acetate fractions,n-butanol fractions and water fractions of V.velutina auraria could effectively reduce the relative expression of iNOS gene of cellular inflammatory factor in RAW264.7 induced by LPS+IFN-γ when the administration concentration of ethyl acetate,n-butanol and water fractions was 300μg/mL.Compounds 2,3,5,6,9-11 inhibited the expression of TNF-α mRNA in RAW264.7 cells induced by LPS combined with IFN-γ(P<0.01).Conclusion The alcoholic extracts and different polar parts of V.velutina auraria can reduce the expression of iNOS in inflammatory cells and have some anti-inflammatory effects.Compounds 1-16 are isolated and identified from the ethyl acetate portion of V.velutina auraria for the first time,of which 2,3,5,6,9-11 may be potential active monomers.
作者
刘超贺
庞秀琴
李成功
许静蕾
钱晓莉
常雅萍
杨志斌
杨银河
王家鹏
肖怀
LIU Chao-he;PANG Xiu-qin;LI Cheng-gong;XU Jing-lei;QIAN Xiao-li;CHANG Ya-ping;YANG Zhi-bin;YANG Yin-he;WANG Jia-peng;XIAO Huai(Yunnan Key Laboratory of Entomological Biopharmaceutical R&D,College of Pharmacy,Dali University,Dali 671000,China;Xiangyun County Comprehensive Inspection and Testing Institute,Xiangyun,672100,China)
出处
《中草药》
CAS
CSCD
北大核心
2023年第22期7351-7357,共7页
Chinese Traditional and Herbal Drugs
基金
国家自然科学基金项目(82160822)
国家自然科学基金项目(82160798)
国家自然科学基金项目(82060765)
国家自然科学基金项目(82260163)
云南省“兴滇英才支持计划”团队专项(202305AS350001)
云南省重大科技专项计划(202002AA100007)
云南省自然科学基金(2017FA050)
云南省科技厅基础研究计划面上项目(202101AT070029)。
关键词
凹纹胡蜂
抗炎活性
对羟基苯甲醛
3
4-二羟基苯乙醇
2-(2-羟基丙酰氧基)丙酸甲酯
对甲氧基苯甲醇
Vespa velutina auraria Smith
anti-inflammatory activity
4-hydroxybenzaldehyde
3,4-dihydroxy-phenethyl alcohol
methyl-2-(2-hydroxy-propionyloxy)propionate
4-methoxybenzyl alcohol
