黄花三宝木中香豆素类成分研究
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摘要
目的对黄花三宝木Trigonostemon lutescens枝叶的95%乙醇提取物中的化学成分进行研究。方法利用硅胶柱色谱、MCI和Sephadex LH-20柱色谱及半制备型高效液相等色谱方法分离纯化,结合理化性质和MS、NMR等波谱学数据对化学结构进行解析。结果从黄花三宝木醋酸乙酯萃取物中发现并鉴定了11个化合物,分别为7个香豆素类:酸橙素烯醇(1)、水合橘皮内酯(2)、花椒毒素(3)、佛手柑内酯(4)、异茴芹内酯(5)、别异欧芹属素乙(6)、异去甲基呋喃羽叶芸香素(7);2个苯丙素糖苷:3,4-dihydroxyallylbenzene-4-O-β-D-glucopyranoside(8)、1-O-β-D-glucopyranosyl-4-allylbenzene(9);1个苯乙醇类:1-(2-ethylphenyl)-1,2-ethanediol(10);1个生物碱类:8-hydroxy-3-methoxy-5H-pyrido [2,1-c] pyrazin-5-one(11)。结论化合物1～11均为首次从三宝木属植物中分离得到。
Objective To study the chemical constituents in 95% ethanol aqueous extract of Trigonostemon lutescens. Methods The open silica gel, MCI, Sephadex LH-20 column chromatography, and the semi-preparative HPLC were used to isolate and purify the chemical constituents from the EtOAc fraction of T. lutescens. The structures of the isolates were elucidated by their physiochemical properties, NMR, and MS spectroscopic data, as well as comparison with literature data. Results Eleven compounds were isolated from the EtOAc fraction of the 95% aqueous EtOH extract of T. lutescens, and their structures were identified as seven coumarins, auraptenol(1), meranzin hydrate(2), xanthotoxin(3), bergapten(4), isoimpinellin(5), alloisoimperatorin(6), and isodemethylfuropinarine(7); Two phenylalanine glycosides, 3,4-dihydroxy allylbenzene-4-O-β-D-glucopyranoside(8) and 1-O-β-D-glucopyranosyl-4-allylbenzene(9); One phenylethanol, 1-(2-ethylphenyl)-1,2-ethanediol(10); One alkaloid, 8-hydroxy-3-methoxy-5 H-pyrido [2,1-c] pyrazin-5-one(11). Conclusion All these compounds are isolated from the genus Trigonostemon for the first time.
Objective To study the chemical constituents in 95% ethanol aqueous extract of Trigonostemon lutescens. Methods The open silica gel, MCI, Sephadex LH-20 column chromatography, and the semi-preparative HPLC were used to isolate and purify the chemical constituents from the EtOAc fraction of T. lutescens. The structures of the isolates were elucidated by their physiochemical properties, NMR, and MS spectroscopic data, as well as comparison with literature data. Results Eleven compounds were isolated from the EtOAc fraction of the 95% aqueous EtOH extract of T. lutescens, and their structures were identified as seven coumarins, auraptenol(1), meranzin hydrate(2), xanthotoxin(3), bergapten(4), isoimpinellin(5), alloisoimperatorin(6), and isodemethylfuropinarine(7); Two phenylalanine glycosides, 3,4-dihydroxy allylbenzene-4-O-β-D-glucopyranoside(8) and 1-O-β-D-glucopyranosyl-4-allylbenzene(9); One phenylethanol, 1-(2-ethylphenyl)-1,2-ethanediol(10); One alkaloid, 8-hydroxy-3-methoxy-5 H-pyrido [2,1-c] pyrazin-5-one(11). Conclusion All these compounds are isolated from the genus Trigonostemon for the first time.
引文
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[15]Ngwendson J N,Bedir E,Efange S M,et al.Constituents of Peucedanum zenkeri seeds and their antimicrobial effects[J].Pharmazie,2003,58(8):587-589.
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[19]Ly T N,Yamauchi R,Shimoyamada M,et al.Isolation and structural elucidation of some glycosides from the rhizomes of smaller galanga(Alpinia officinarum Hance)[J].J Agric Food Chem,2002,50(17):4919-4924.
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[22]Cheng F,Li A,Wang J Z.A new alkaloid from Solanum cathayanum[J].Chin Chem Lett,2008,19(1):68-70.
[2]Tempeam A,Thasana N,Dawornkricharut A,et al.In vitro cytotoxicity of some thai medicinal plants anddaphnane diterpenoid from Trigonostemon redioides[J].Mahidol U J Pharm Sci,2002,29(3/4):25-31.
[3]岑长春,刘景龙,张卫丽,等.三宝木属植物化学成分和药理活性研究进展[J].海南师范大学学报,2009,22(4):436-440.
[4]Yang B,Meng Z Q,Li Z L,et al.Three daphnane diterpenoids from Trigonostemon xyphophylloides[J].Phytochem Lett,2015,11(1):270-274.
[5]Li S F,Zhang Y,Li Y,et al.β-Carboline alkaloids from the leaves of Trigonostemon lii Y.T.Chang[J].Bioorg Med Chem Lett,2012,22(6):2296-2299.
[6]Zhu Q,Tang C P,Ke C Q,et al.Constituents of Trigonostemon chinensis[J].J Nat Prod,2010,73(1):40-44.
[7]余丽,梅文莉,左文健,等.剑叶三宝木枝条中的抗菌活性成分研究[J].时珍国医国药,2013,24(3):591-593.
[8]Jayasuriya H,Zink D L,Borris R P,et al.Rediocides B-E,potent insecticides from Trigonostemon reidioides[J].JNat Prod,2004,67(2):228-231.
[9]杨长水,韩苏乔,沈新宇,等.黄花三宝木枝叶的化学成分研究[J].中成药,2017,39(7):1427-1430.
[10]Ma S S,Mei W L,Guo Z K,et al.Two new types of bisindole alkaloid from Trigonostemon lutescens[J].Org Lett,2013,15(7):1492-1495.
[11]Tempeam A,Thasana N,Pavaro C,et al.A new cytotoxic daphnane diterpenoid,Rediocide G,from Trigonostemon reidioides[J].Chem Pharm Bull,2005,53(10):1321-1323.
[12]Barik B R,Dey A K,Das P C,et al.Coumarins of Murraya exotica-absolute configuration of auraptenol[J].Phytochemistry,1983,22(3):792-794.
[13]Zhou P,Takaishi Y,Duan H,et al.Coumarins and bicoumarin from Ferula sumbul:Anti-HIV activity and inhibition of cytokine release[J].Phytochemistry,2000,53(6):689-697.
[14]杨槐,周勤梅,彭成,等.益母草香豆素类化学成分与抗血小板聚集活性[J].中国中药杂志,2014,39(22):4356-4359.
[15]Ngwendson J N,Bedir E,Efange S M,et al.Constituents of Peucedanum zenkeri seeds and their antimicrobial effects[J].Pharmazie,2003,58(8):587-589.
[16]刘韶,章伟,何桂霞,等.单面针茎化学成分的研究[J].中国中药杂志,2009,34(5):571-573.
[17]张新勇,向仁德.蛇床子化学成分的研究[J].中草药,1997,28(10):588-590.
[18]Murray R D H,Jorge Z D,Boag D M.Claisen rearrangements-XIV.Synthesis of the coumarin,benahorin and revision of the structure of marmelide[J].Tetrahedron,1984,40(24):5225-5227.
[19]Ly T N,Yamauchi R,Shimoyamada M,et al.Isolation and structural elucidation of some glycosides from the rhizomes of smaller galanga(Alpinia officinarum Hance)[J].J Agric Food Chem,2002,50(17):4919-4924.
[20]Ryuichi H,Dervilla M X D.Glycoside from Pinus contorta needles[J].Phytochemistry,1977,16(10),1587-1590.
[21]Yayli N.Isolation and characterization of dibenzoated aromatic compounds[J].Turkish J Chem,1993,17:208-214.
[22]Cheng F,Li A,Wang J Z.A new alkaloid from Solanum cathayanum[J].Chin Chem Lett,2008,19(1):68-70.