[關(guān)鍵詞]
[摘要]
目的 研究檉柳科水柏枝屬小花水柏枝Myricaria wardii的抗補體活性成分。方法 采用正相硅膠色譜、凝膠柱色譜、ODS色譜和半制備高效液相色譜等方法進行分離純化,通過波譜數(shù)據(jù)(NMR和MS等)鑒定化合物結(jié)構(gòu),并采用溶血法測定化合物的抗補體活性。結(jié)果 從小花水柏枝的95%乙醇提取物中共分離鑒定41個化合物,分別為 (-)-3,6-bis(4-hydroxy-3-methoxyphenyl)-5-(4-hydroxyphenethyl)hexahydro-4H-furo[3,4-c]pyrrol-4-one(1)、3-羥基-4,5-二甲氧基苯甲酸甲酯(2)、3-羥基-4-甲氧基苯甲酸甲酯(3)、香草醛(4)、羅布麻寧(5)、丁香酸甲酯(6)、松柏醛(7)、3,4-二羥基-5-甲氧基苯甲酸甲酯(8)、異阿魏酸甲酯(9)、對羥基苯甲醛(10)、對羥基苯乙酮(11)、黑麥草內(nèi)酯(12)、(+)-去氫催吐蘿芙木醇(13)、沒食子酸(14)、原兒茶酸(15)、3-O-甲基沒食子酸(16)、沒食子酸乙酯(17)、吐葉醇(18)、3,5,6-trihydroxy-7-megastigmen-9-one(19)、咖啡酸(20)、蚱蜢酮(21)、花旗松素(22)、3-羥基-4,5-二甲氧基苯甲酸(23)、對香豆素(24)、丁香酸(25)、異落葉松脂素(26)、burselignan(27)、(1',1',2',2'-tetramethylpropyl)-1,2-benzenediol(28)、二氫山柰酚(29)、槲皮素(30)、N-反式-阿魏酰酪胺(31)、terrestiamide(32)、(R)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4hydroxyphenyl)-2-methoxyethyl]acrylamide(33)、(Z)-8,11,12-trihydroxy-9-octadecanoic acid(34)、9,12,13-trihydroxy-10,15-octadecadienoic acid(35)、水柏枝素A(36)、異阿魏酸(37)、原兒茶醛(38)、N-反式-阿魏酰-3-甲氧基酪胺(39)、山柰酚(40)、香草酸甲酯(41)?;钚詼y定結(jié)果表明,26個化合物(13個酚酸及其衍生物、4個黃酮、2個木脂素、3個苯丙素、3個酚酰胺和1個萜類)表現(xiàn)出明顯的抗補體活性,其半數(shù)抑制溶血濃度(half inhibit hemolysis concentration,CH50)為(0.20±0.03)~(4.72±0.01)mmol/L。結(jié)論 化合物1為新化合物,命名為水柏枝脂素A(myricarian A),倍半萜類成分(12、13、18、19、21)首次從水柏枝屬植物中分離得到,酚酸及其衍生物和黃酮類成分為小花水柏枝主要的抗補體活性成分。
[Key word]
[Abstract]
Objective To study the anti-complementary constituents of Myricaria wardii. Methods The compounds were isolated and purified by silica gel column chromatography, gel chromatography, ODS column chromatography, and semi-preparative HPLC. The structures were identified by spectral data (NMR and MS) and relevant references. Besides, the anti-complementary activities of these compounds were evaluated by hemolysis method. Results A total of 41 compounds were isolated and identified from M. wardii, including (−)-3,6-bis(4-hydroxy-3-methoxyphenyl)-5-(4-hydroxyphenethyl)hexahydro-4H-furo[3,4-c]pyrrol-4-one (1), methyl 3-hydroxy-4,5-dimethoxybenzoate (2), methyl 3-hydroxy-4-methoxybenzoate (3), vanillin (4), apocynin (5), methyl syringate (6), coniferaldehyde (7), methyl 3,4-dihydroxy-5-methoxybenzoate, (8), methyl isoferulate (9), p-hydroxybenzaldehyde (10), p-hydroxyacetophenone (11), loliolide (12), (+)-dehydrovomifoliol (13), gallic acid (14), protocatechuic acid (15), 3-O-methylgallic acid (16), ethyl gallate (17), vomifoliol (18), 3,5,6-trihydroxy-7-megastigmen-9-one (19), caffeic acid (20), grasshopper ketone (21), taxifolin (22), 3-hydroxy-4,5-dimethoxybenzoic acid (23), p-coumaric acid (24), syringic acid (25), isolariciresino (26), burselignan (27), (1',1',2',2'-tetramethylpropyl)-1,2-benzenediol (28), dihydrokaempferol (29), quercetin (30), N-trans-feruloyltyramine (31), terrestiamide (32), (R)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4hydroxyphenyl)-2-methoxyethyl] acrylamide (33), (Z)-8,11,12-trihydroxy-9-octadecanoic acid (34), 9,12,13-trihydroxy-10,15-octadecadienoic acid (35), myricaria A (36), isoferulic acid (37), protocatechualdehyde (38), N-trans-feruloyl-3-methyldopamine (39), kaempferol (40), methyl vanillate (41). A total of 26 compounds, including 13 phenolic acid derivates, four flavonoids, two lignans, three phenylpropanoids, three phenolic amides and one terpenoid, showed anti-complementary activities with the half inhibit hemolysis concentration (CH50) ranging from (0.20 ±0.03) to (4.72 ±0.01) mmol/L. Conclusion Compound 1 is a new compound isolated from M. wardii named myricarian A, and sesquiterpenoids (12, 13, 18, 19, 21) are isolated from Myricaria for the first time. Phenolic derivates and flavonoids are considered as the main anti-complementary components of M. wardii.
[中圖分類號]
R284.1
[基金項目]
國家自然科學(xué)基金面上項目(82173940);西藏自治區(qū)中央引導(dǎo)地方項目(XZ202001YD0003C);西藏自治區(qū)重大科技專項(XZ201801-GA-13)