水曲柳树枝的化学成分

Lin Sheng, Zhang Yan-ling, Liu Ming-tao, Zi Jia-chen, Gan Mao-luo, Song Wei-xia, Fan Xiao-na, Wang Xiao-na, Yang Yong-chun, Shi Jian-gong

Zhongguo Zhong Yao Za Zhi. 2015 Jul;40(13):2602-11.

Using a combination of various chromatographic techniques including column chromatography over silica gel, Sephadex LH-20, macroporous adsorbent resin, and reversed-phase HPLC, 115 compounds including diterpenes, sesquiterpenes, treterpenes, coumarins, lignans, fatty acid derivatives, and simple aromatic derivatives were isolated from an ethanol extract of branch of Fraxinus sieboldiana (Oleaceaue), and their structures of the compounds were elucidated by spectroscopic methods including 1 D, 2D NMR and MS techniques. Among them, 41 compounds were new. In previous reports, we have been described the isolation, structure elucidation, and bioactivities of the 41 new compounds and 22 known orii including 8 coumarins, 4 phenolic and 12 phenylethanoidal glycosides. As a consequence, we herein reported the isolation and structure elucidation of the remaining 50 known compounds including 8- hydroxy-12-oxoabieta-9(11),13-dien-20-oic 8, 20-lactone(1), 6beta-hydroxyfcrruginol(2),(+)-pisiferic acid(3), (+)-pisiferal(4),(+)-7-dehydroabiet6none(5), 1-oxomiltirone(6), subdigitatone(7), linarionoside B(8), (9S)-linarionoside B(9), (3R,9R)-3-hydroxy-7,8-dihydro-beta-ionol 9-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside(10), ursolic acid(11), betulinic acid(12), euscaphic acid(13), (+)-syringaresinol(14), (+)-fraxiresinol(15), (+)-1-hydroxysyringaresinol(16), pinoresinol(17), medioresinol(18), 8-acetoxypinoresinol(19), epipinoresinol(20), (-)-olivil(21), (+)-cyclo-olivil(22), 3,3'-dimethoxy-4,4',9-trihydroxy-7,9'-epoxylignan-7'-one(23),(+)-1-hydroxypinoresinol 4'-O-beta-D-glucopyranoside (24), (+)-1-hydroxypinoresinol 4"-O-beta-D-glucopyranoside(25),(+)-syringaresinol O-beta-D-glucopyranoside (26), liriodendrin (27), ehletianol D(28), icariside E5(29) (-)-(7R, 8R)-threo-1-C-syringylglycerol(30),(-)-(7R, 8S)-erythro-guaiacylglycerol (31),(-)-(7R, 8R)-threo-guaiacylglycerol(32), 3-(4-beta-D-glucopyranosyloxy-3-methoxy)-phenyl-2E-propenol(33),2,3-dihydroxy-l-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone(34), 2,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (35), 3-hydroxy-l-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone(36), omega-hydroxypropioguaiacone(37), sinapyladehyde(38), trans-p-hydroxycinnamaldehyde(39), syringic acid(40), vanilic acid(41), vanillin(42), 4-hydroxy-benzaldehyde (43), (24R)-24-ethyl-5alpha-cholestane-3beta,5,6beta-triol(44), beta-sitosterol(45), daucosterol(46), 2,6-dimethoxy-I,4-benzoquinone(47), 2,6-dimethoxy-pyran-4-one(48), 1-(beta-D-ribofuranosyl)uracil(49), and mannitol(50). Compouds 1-7,12,18,28-37,44 and 48 were obtained from the genus Fraxinus for the first time.

采用多种色谱技术相结合的方法，包括硅胶柱色谱、葡聚糖凝胶LH - 20柱色谱、大孔吸附树脂柱色谱和反相高效液相色谱，从白蜡树（木犀科）枝条的乙醇提取物中分离出115种化合物，包括二萜类、倍半萜类、三萜类、香豆素类、木脂素类、脂肪酸衍生物和简单芳香族衍生物，并通过一维、二维核磁共振和质谱等光谱方法对这些化合物的结构进行了阐明。其中，41种化合物为新化合物。在之前的报道中，我们已经描述了41种新化合物和22种已知化合物（包括8种香豆素类、4种酚类和12种苯乙醇苷类）的分离、结构鉴定及生物活性。因此，我们在此报道其余50种已知化合物的分离和结构鉴定，这些化合物包括8 - 羟基 - 12 - 氧代枞酸 - 9(11),13 - 二烯 - 20 - 酸8,20 - 内酯(1)、6β - 羟基铁锈醇(2)、( + ) - 松脂酸(3)、( + ) - 松脂醛(4)、( + ) - 7 - 脱氢枞酮(5)、1 - 氧代异欧前胡素(6)、亚指状内酯(7)、紫丁香苷B(8)、(9S) - 紫丁香苷B(9)、(3R,9R) - 3 - 羟基 - 7,8 - 二氢 - β - 紫罗兰醇9 - O - β - D - 芹菜糖基 - (1→6) - β - D - 葡萄糖苷(10)、熊果酸(11)、桦木酸(12)、悬钩子酸(13)、( + ) - 丁香树脂醇(14)、( + ) - 白蜡树脂醇(15)、( + ) - 1 - 羟基丁香树脂醇(16)、松脂醇(17)、中树脂醇(18)、8 - 乙酰氧基松脂醇(19)、表松脂醇(20)、( - ) - 橄榄脂素(21)、( + ) - 环橄榄脂素(22)、3,3'-二甲氧基 - 4,4',9 - 三羟基 - 7,9'-环氧木脂素 - 7'-酮(23)、( + ) - 1 - 羟基松脂醇4'-O - β - D - 葡萄糖苷(24)、( + ) - 1 - 羟基松脂醇4'' - O - β - D - 葡萄糖苷(25)、( + ) - 丁香树脂醇O - β - D - 葡萄糖苷(26)、鹅掌楸苷(27)、埃氏醇D(28)、淫羊藿苷E5(29)、( - ) - (7R,8R) - 苏式 - 1 - C - 丁香基甘油(30)、( - ) - (7R,8S) - 赤式 - 愈创木基甘油(31)、( - ) - (7R,8R) - 苏式 - 愈创木基甘油(32)、3 - (4 - β - D - 葡萄糖氧基 - 3 - 甲氧基) - 苯基 - 2E - 丙烯醇(33)、2,3 - 二羟基 - 1 - (4 - 羟基 - 3,5 - 二甲氧基苯基) - 1 - 丙酮(34)、2,3 - 二羟基 - 1 - (4 - 羟基 - 3 - 甲氧基苯基) - 1 - 丙酮(35)、3 - 羟基 - 1 - (4 - 羟基 - 3,5 - 二甲氧基苯基) - 1 - 丙酮(36)、ω - 羟基 - 苯并愈创木酮(37)、芥子醛(38)、反式 - 对羟基肉桂醛(39)、丁香酸(40)、香草酸(41)、香草醛(42)