黄芫花中酚类成分
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摘要
采用硅胶、Sephadex LH-20、ODS和制备型HPLC等色谱分离技术对黄芫花中的酚类成分进行了分离纯化,并通过波谱学数据进行结构鉴定。从中共分离鉴定13个酚类化合物,其中有5个黄酮及苷类:luteolin 7-O-β-D-glucopyranoside(1),luteolin 4'-O-β-D-glucopyranoside(2),kaempferol 3-O-β-D-glucopyranoside(3),chrysoeriol 4'-O-β-D-glucopyranoside(4),金圣草黄素(5); 8个木脂素及苷类:(-)-secoisolariciresinol(6),acanthosessilin A(7),(-)-nortrachelogenin(8),(+)-异落叶松树脂醇(9),芝麻素(10),丁香脂素(11),(+)-epipinoresinol(12),[3,3',4,4'-tetrahydro-6,6'-dimethoxy-3,3'-bi-2H-benzopyran]-4,4'-diol(13)。化合物1,3,5～8,10,11,13为首次从本植物中分离得到,化合物1,5,7,10,13为首次从荛花属植物中分离得到。
The phenolic constituents of Wikstroemia chamaedaphne were investigated by various column chromatographic methods including silica gel,Sephadex LH-20,ODS and preparative HPLC,and their chemical structures were identified by physico-chemical properties and spectral analyses. Thirteen phenolic compounds were isolated and elucidated,including five flavonoids: luteolin 7-O-β-D-glucopyranoside(1),luteolin 4'-O-β-D-glucopyranoside(2),kaempferol 3-O-β-D-glucopyranoside(3),chrysoeriol 4'-O-β-D-glucopyranoside(4),chrysoeriol(5); and eight lignans:(-)-secoisolariciresinol(6),acanthosessilin A(7),(-)-nortrachelogenin(8),(+)-isolariciresinol(9),sesamin(10),syringaresinol(11),(+)-epipinoresinol(12),and [3,3',4,4'-tetrahydro-6,6'-dimethoxy-3,3'-bi-2 H-benzopyran]-4,4'-diol(13). Compounds 1, 3, 5-8, 10, 11 and 13 were obtained from the plants of W. chamaedaphne for the first time,and compounds 1,5,7,10 and 13 were obtained from the Wikstroemia genus for the first time.
The phenolic constituents of Wikstroemia chamaedaphne were investigated by various column chromatographic methods including silica gel,Sephadex LH-20,ODS and preparative HPLC,and their chemical structures were identified by physico-chemical properties and spectral analyses. Thirteen phenolic compounds were isolated and elucidated,including five flavonoids: luteolin 7-O-β-D-glucopyranoside(1),luteolin 4'-O-β-D-glucopyranoside(2),kaempferol 3-O-β-D-glucopyranoside(3),chrysoeriol 4'-O-β-D-glucopyranoside(4),chrysoeriol(5); and eight lignans:(-)-secoisolariciresinol(6),acanthosessilin A(7),(-)-nortrachelogenin(8),(+)-isolariciresinol(9),sesamin(10),syringaresinol(11),(+)-epipinoresinol(12),and [3,3',4,4'-tetrahydro-6,6'-dimethoxy-3,3'-bi-2 H-benzopyran]-4,4'-diol(13). Compounds 1, 3, 5-8, 10, 11 and 13 were obtained from the plants of W. chamaedaphne for the first time,and compounds 1,5,7,10 and 13 were obtained from the Wikstroemia genus for the first time.
引文
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[2]张志强,李石飞,张立伟,等.黄芫花化学成分及其抗乙肝病毒作用[J].中草药,2017,48(7):1292.
[3] He W D,Cik M,Appendino G,et al. Daphnane-type diterpene orthoesters and their biological activities[J]. Mini-Rev Med Chem,2002,2(2):185.
[4] Liao S G,Chen H D,Yue J M,et al. Plant orthoesters[J].Chem Rev,2009,109(3):1092.
[5]王成瑞,黄慧珠,韩玖,等.河朔荛花素的分离与鉴定[J].中国药学杂志,1981,16(6):51.
[6]康少文,于永芳,魏清波,等.黄芫花中期引产有效成分的研究[J].承德医学院学报,1984,1(1):5.
[7] Liu M M,Zhou L,He P L,et al. Discovery of flavonoid derivatives as anti-HCV agents via pharmacophore search combining molecular docking strategy[J]. Eur J Med Chem,2012,52(11):33.
[8] Toshmatov Z O,Eshbakova K A,Aisa H A. Glycoside flavonoids from Dracocephalum komarovii[J]. Chem Nat Compd,2018,54(2):358.
[9] Krzaczek T,Gawrońskagrzywacz M. Flavonoids and coumarins from Hieracium pilosella L.(Asteraceae)[J]. Acta Soc Bot Pol,2009,78(3):189.
[10] Beninger C W,Hosfield G L,Nair M G. Flavonol glycosides from the seed coat of a new manteca-type dry bean(Phaseolus vulgaris L.)[J]. J Agr Food Chem,1999,47(1):352.
[11] Lu Y,Sun Y,Foo L Y,et al. Phenolic glycosides of forage legume Onobrychis viciifolia[J]. Phytochemistry, 2000, 55(1):67.
[12]张兴,梅文莉,曾艳波,等.槟榔果实的酚类化学成分与抗菌活性的初步研究[J].热带亚热带植物学报,2009,17(1):74.
[13]朱莹莹,李敏,陈重,等.炎宁颗粒的化学成分研究[J].中成药,2013,35(5):988.
[14] Lee D Y,Seo K H,Jeong R H,et al. Anti-inflammatory lignans from the fruits of Acanthopanax sessiliflorus[J]. Molecules,2012,18(1):41.
[15] Jang S W,Suh W S,Kim C S,et al. A new phenolic glycoside from Spiraea prunifolia var. simpliciflora twigs[J]. Arch Pharm Res,2015,38(11):1943.
[16] Delgado J,Thomson K,Russell N,et al. Structural and spectroscopic characteristics of two new dibenzylbutane type lignans from Taxus baccata L.[J]. J Mol Struct,2003,655(3):459.
[17]刘亚华,李继新,辛来香,等.雷山产淡黄香茶菜化学成分的研究[J].中草药,2016,47(10):1657.
[18]王淑慧,张屏,伊丽娜,等.蒙药材藜芦的化学成分和抗氧化活性研究[J].中药材,2018,41(3):608.
[19]赵阳,梁丽珍,李厚金,等.威灵仙的化学成分研究[J].中山大学学报:自然科学版,2012,51(3):63.
[20] Chen Y,Yang G,Li Y. Chemical constituents of Tripterygium wilfordii[J]. Helv Chim Acta,2005,83(12):3344.
[21]韩曼珠,王芬,李丽,等.抗纤肝汤治疗慢性乙型肝炎肝纤维化54例[J].中国实验方剂学杂志,2015,21(16):183.
[22]孙良秀,吴晶,蒋荆萍,等.强肾愈肝汤联合恩替卡韦治疗慢性乙型肝炎40例[J].中国实验方剂学杂志,2013,19(22):287.