[关键词]
[摘要]
目的 对檀香科槲寄生属植物槲寄生Viscum coloratum干燥地上部分的化学成分进行系统研究。方法 采用连续加热回流提取法以及大孔树脂柱吸附法进行有效组分富集;综合运用硅胶、ODS、Sephadex LH-20及HPLC等色谱方法,对其化学成分进行分离纯化;通过UV、IR、1D-NMR、2D-NMR、MS等波谱学手段,对所分得的单体化合物进行结构鉴定。利用脂多糖诱导小鼠巨噬细胞(RAW264.7)建立的炎症模型,测定分离得到的单体化合物的抗炎作用。结果 从槲寄生95%乙醇提取物中分离并鉴定了37个化合物,分别鉴定为10-(7-((1R)-1,3-dimethylbicyclo[3.1.1]hept-3-en-1-yl) propylidene)propane-11,15-diol(1)、大瑶灵芝内酯A(2)、脱落酸(3)、桦木酸甲酯(4)、齐墩果酸(5)、白桦脂酸(6)、3,28-二羟基羽扇豆醇(7)、(−)-黑麦草内酯(8)、betulinic 3β-hydroxy-11α,12α- epoxyoleanan-28,13β-olide(9)、松柏苷(10)、松脂酚(11)、滨蒿内酯(12)、紫丁香苷(13)、threo-syringylglycerol-8-O-4'-(sinapyl alcohol) ether(14)、香茶菜苷II(15)、阿魏酸(16)、落叶松脂醇-4'-O-β-D-葡萄糖苷(17)、(−)-里奥树脂醇-3α-O-β-D-吡喃葡萄糖苷(18)、(+)-南烛木树脂酚(19)、咖啡酸(20)、(−)-5'-甲氧基松脂素(21)、(−)-松脂素-4,4'-二-O-β-D-吡喃葡萄糖苷(22)、苦玄参苷C(23)、(−)-丁香树脂酚(24)、柚皮素(25)、槲皮素(26)、7,3',4'-三甲基槲皮素(27)、高圣草素(28)、2-hydroxy-4-O-α-L-(3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl) phenylarabinofuranoside(29)、香草酸(30)、羟基酪醇(31)、邻苯二甲酸二丁酯(32)、salicyl alcohol-1-O-β-D (3'-benozyl) glucopyranoside(33)、methyl 2-O-β-D-glucopyranosylbenzoate(34)、succinic acid monobutyl ester(35)、1-ethyl nonanedioate(36)、1-azeloyl-rac-glycer(37)。结论 化合物1为新化合物,命名为α-反式柠檬烯二醇;化合物4、9、10、14、15、17、22、23、31、32、34~37为首次从檀香科中分离得到,化合物12、33为首次从槲寄生属植物中分离得到,化合物11、21、24为首次从槲寄生中分离得到。体外活性研究结果表明,化合物1、26、27、30抗炎活性最为显著。
[Key word]
[Abstract]
Objective To systematically study the chemical constituents of the dry aboveground parts of Viscum coloratum of the Santalaceae. Methods The effective components were enriched by continuous heating reflux extraction and macroporous resin column adsorption. The chemical components were separated and purified by silica gel, ODS, Sephadex LH-20 and HPLC. The structure of the isolated monomer compounds was identified by UV, IR, 1D-NMR, 2D-NMR, MS and other spectroscopic methods. The anti-inflammatory effects of the isolated monomeric compounds were determined using an inflammatory model established by LPS-induced mouse macrophages (RAW264.7). Results A total of 37 compounds were isolated and identified from 95% ethanol extract of V. coloratum. They were identified as 10-(7-((1R)-1,3-dimethylbicyclo[3.1.1]hept-3-en-1-yl)propylidene)propane-11,15-diol (1), dayaolingzhilactone A (2), abscisic acid (3), betulinic acid methyl ester (4), oleanolic acid (5), betulinic acid (6), 3,28-dihydroxyllupeol (7), (−)-loliolide (8), 3β-hydroxy-11α,12α-epoxyoleanan-28,13β-olide (9), coniferin (10), pinoresinol (11), scoparone (12), syringin (13), threo-syringylglycerol-8-O-4'-(sinapyl alcohol) ether (14), isodonosides Ⅱ (15), ferulic acid (16), lariciresinol-4'-O-β-D-glucoside (17), (−)-lyoniresinol-3α-O-β-D-glucopyranoside (18), (+)-lyoniresino (19), caffeic acid (20), (−)-medioresinol (21), (−)-pinoresinol-4,4'-di-O-β-D-glucopyranoside (22), picraquassioside C (23), (−)-syringaresinol (24), naringenin (25), quercetin (26), 7,3',4'-trimethylquercetin (27), homoeriodictyol (28), 2-hydroxy-4-O-α-L-(3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl) phenylarabino- furanoside (29), vanillic acid (30), hydroxytyrosol (31), dibutyl phthalate (32), salicyl alcohol-1-O-β-D (3'-benozyl) glucopyranoside (33), methyl 2-O-β-D-glucopyranosylbenzoate (34), succinic acid monobutyl ester (35), 1-ethyl nonanedioate (36), 1-azeloyl-rac-glycer (37). Conclusion Compound 1 is a new compound, named α-trans limonenediol. Compounds 4, 9, 10, 14, 15, 17, 22, 23, 31, 32, and 34—37 are isolated from Santalaceae family for the first time, compounds 12 and 33 were isolated from Viscum genus for the first time and compounds 11, 21 and 24 are isolated from this plant for the first time. The results of in vitro activity studies indicate that compounds 1, 26, 27 and 30 exhibit the most significant anti-inflammatory activity.
[中图分类号]
R284.1
[基金项目]
国家自然科学基金项目(U22A20370);黑龙江省自然科学基金基金项目(PL2024H232);黑龙江省“双一流”学科协同创新成果建设项目(LJGXCG2022-096)