豆叶九里香的化学成分研究
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摘要
利用开放的硅胶、ODS和Sephadex LH-20柱色谱及半制备型高效液相等色谱方法对豆叶九里香Murraya euchrestifolia中的化学成分进行分离纯化,结合理化性质和MS,NMR等波谱学数据对化学结构进行解析。结果从豆叶九里香95%乙醇提取物的二氯甲烷部位共分离并鉴定了18个化合物,分别为sakuranetin(1),eriodictyol-7,4'-dimethyl ether(2),isosakuranetin(3),5-hydroxy-7,4'-dimethoxyflavanone(4),eriodictyol-7-methyl ether(5),lichexanthon(6),5,6,7-trimethoxycoumarin(7),5-hydroxy-6,8-dimethoxycoumarin(8),8-hydroxy-6-methoxy-3-n-pentylisocoumarin(9),ethyl caffeate(10),4-hydroxy-3,5-dimethoxycinnamic acid ethyl ester(11),methyl 3-(5'-hydroxyprenyl)-coumarate(12),(E)-coniferol(13),β-hydroxypropiovanillone(14),3-hydroxy-7,8-didehydro-β-ionone(15),3β-hydroxy-5α,6α-epoxy-7-megastigmen-9-one(16),grasshopper ketone(17),4-hydroxy-3,5-dimethoxybenzaldehyde(18),其中化合物1~15和18为首次从九里香属植物中分离得到,16和17为首次从该植物中分离得到。
The open silica gel,ODS,and Sephadex LH-20 column chromatography,along with the semi-preparative HPLC was used to isolate and purify the chemical constituents from Murraya euchrestifolia. The structures of the isolates were elucidated by their physiochemical properties,NMR,and MS spectroscopic data,as well as comparison with literature data. Eighteen compounds were isolated from the CH2Cl2 fraction of the 95% aqueous Et OH extract of M. euchrestifolia,and their structures were identified as sakuranetin(1),eriodictyol-7,4'-dimethyl ether(2),isosakuranetin(3),5-hydroxy-7,4'-dimethoxyflavanone(4),eriodictyol-7-methyl ether(5),lichexanthon(6),5,6,7-trimethoxycoumarin(7),5-hydroxy-6,8-dimethoxycoumarin(8),8-hydroxy-6-methoxy-3-n-pentylisocoumarin(9),ethyl caffeate(10),4-hydroxy-3,5-dimethoxycinnamic acid ethyl ester(11),methyl 3-(5'-hydroxyprenyl)-coumarate(12),(E)-coniferol(13),β-hydroxypropiovanillone(14),3-hydroxy-7,8-didehydro-β-ionone(15),3β-hydroxy-5α,6α-epoxy-7-megastigmen-9-one(16),grasshopper ketone(17),and 4-hydroxy-3,5-dimethoxybenzaldehyde(18). Compounds1-15 and 18 were first obtained from the plants of Murraya genus,and compounds 16 and 17 were isolated from M. euchrestifolia for the first time.
The open silica gel,ODS,and Sephadex LH-20 column chromatography,along with the semi-preparative HPLC was used to isolate and purify the chemical constituents from Murraya euchrestifolia. The structures of the isolates were elucidated by their physiochemical properties,NMR,and MS spectroscopic data,as well as comparison with literature data. Eighteen compounds were isolated from the CH2Cl2 fraction of the 95% aqueous Et OH extract of M. euchrestifolia,and their structures were identified as sakuranetin(1),eriodictyol-7,4'-dimethyl ether(2),isosakuranetin(3),5-hydroxy-7,4'-dimethoxyflavanone(4),eriodictyol-7-methyl ether(5),lichexanthon(6),5,6,7-trimethoxycoumarin(7),5-hydroxy-6,8-dimethoxycoumarin(8),8-hydroxy-6-methoxy-3-n-pentylisocoumarin(9),ethyl caffeate(10),4-hydroxy-3,5-dimethoxycinnamic acid ethyl ester(11),methyl 3-(5'-hydroxyprenyl)-coumarate(12),(E)-coniferol(13),β-hydroxypropiovanillone(14),3-hydroxy-7,8-didehydro-β-ionone(15),3β-hydroxy-5α,6α-epoxy-7-megastigmen-9-one(16),grasshopper ketone(17),and 4-hydroxy-3,5-dimethoxybenzaldehyde(18). Compounds1-15 and 18 were first obtained from the plants of Murraya genus,and compounds 16 and 17 were isolated from M. euchrestifolia for the first time.
引文
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[18]Gangar M,Ittuveetil A,Goyal S,et al.Anti selective glycolate aldol reactions of(S)-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one:application towards the asymmetric synthesis of8-4'-oxyneolignans[J].RSC Adv,2016,6(104):102116.
[19]Lancefield C S,Ojo O S,Tran F,et al.Isolation of functionalized phenolic monomers through selective oxidation and CO bond cleavage of theβ-O-4 linkages in lignin[J].Angew Chem Int Edit,2015,54(1):258.
[20]Yamano Y,Watanabe Y,Watanabe N,et al.Stereocontrolled synthesis of glucosidic damascenone precursors[J].J Chem Soc Perkin Trans 1,2002,(24):2833.
[21]D'Abrosca B,Della Greca M,Fiorentino A,et al.Structure elucidation and phytotoxicity of C13 nor-isoprenoids from Cestrum parqui[J].Phytochemistry,2004,65(4):497.
[22]Della Greca M,Di Marino C,Zarrelli A,et al.Isolation and phytotoxicity of apocarotenoids from Chenopodium album[J].J Nat Prod,2004,67(9):1492.
[23]Shirali A,Sriram M,Hall J J,et al.Development of synthetic methodology suitable for the radiosynthesis of combretastatin A-1(CA1)and its corresponding prodrug CA1P[J].J Nat Prod,2009,72(3):414.
[2]纪晓多,濮全龙,杨桂芝.豆叶九里香挥发油化学成分的研究[J].药学学报,1983,17(5):626.
[3]Wu T S,Wang M L,Wu P L,et al.Carbazole alkaloids from the leaves of Murraya euchrestifolia[J].Phytochemistry,1996,41(5):1433.
[4]Wu T S,Wang M L,Wu P L,et al.Two carbazole alkaloids from leaves of Murraya euchrestifolia[J].Phytochemistry,1995,40(6):1817.
[5]Ito C,Okahana N,Wu T S,et al.New carbazole alkaloids from Murraya euchrestifolia[J].Chem Pharm Bull,1992,40(1):230.
[6]Jerz G,Waibel R,Achenbach H.Cyclohexanoid protoflavanones from the stem-bark and roots of Ongokea gore[J].Phytochemistry,2005,66(14):1698.
[7]Vasconcelos J M J,Silva A M S,Cavaleiro J A S.Chromones and flavanones from Artemisia campestris subsp.maritime[J].Phytochemistry,1998,49(5):1421.
[8]Hattori H,Okuda K,Murase T,et al.Isolation,identification,and biological evaluation of HIF-1-modulating compounds from Brazilian green propolis[J].Bioorg Med Chem,2011,19(18):5392.
[9]Gu J Q,Park E J,Vigo J S,et al.Activity-guided isolation of constituents of Renealmia nicolaioides with the potential to induce the phaseⅡenzyme quinone reductase[J].J Nat Prod,2002,65(11):1616.
[10]Vasconcelos J M J,Silva A M S,Cavaleiro J A S.Chromones and flavanones from Artemisia campestris subsp.maritime[J].Phytochemistry,1998,49(5):1421.
[11]Brandao L F G,Alcantara G B,Matos M de F C,et al.Cytotoxic evaluation of phenolic compounds from lichens against melanoma cells[J].Chem Pharm Bull,2013,61(2):176.
[12]Saeed M A,Sabir A W.Irritant and cytotoxic coumarins from Angelica glauca Edgew roots[J].J Asian Nat Prod Res,2008,10(1):49.
[13]Kim K S,Lee S,Shin J S,et al.Arteminin,a new coumarin from Artemisia apiacea[J].Fitoterapia,2002,73(3):266.
[14]Kijjoa A,Gonzalez M J T G,Pinto M M M,et al.Constituents of Knema laurina and Knema tenuinervia ssp.setosa[J].Planta Med,1991,57(6):575.
[15]Li J R,Bai,Y J,Wang B,et al.A monoterpene glycoside from Echinacea purpurea[J].J Chin Pharm Sci,2003,12(4):181.
[16]Sathish Kumar B,Singh A,Kumar A,et al.Synthesis of neolignans as microtubule stabilisers[J].Bioorg Med Chem,2014,22(4):1342.
[17]Jakupovic J,Tan R X,Bohlmann F,et al.Prenylated coumarates from Artemisia xanthochroa[J].Phytochemistry,1990,29(11):3683.
[18]Gangar M,Ittuveetil A,Goyal S,et al.Anti selective glycolate aldol reactions of(S)-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one:application towards the asymmetric synthesis of8-4'-oxyneolignans[J].RSC Adv,2016,6(104):102116.
[19]Lancefield C S,Ojo O S,Tran F,et al.Isolation of functionalized phenolic monomers through selective oxidation and CO bond cleavage of theβ-O-4 linkages in lignin[J].Angew Chem Int Edit,2015,54(1):258.
[20]Yamano Y,Watanabe Y,Watanabe N,et al.Stereocontrolled synthesis of glucosidic damascenone precursors[J].J Chem Soc Perkin Trans 1,2002,(24):2833.
[21]D'Abrosca B,Della Greca M,Fiorentino A,et al.Structure elucidation and phytotoxicity of C13 nor-isoprenoids from Cestrum parqui[J].Phytochemistry,2004,65(4):497.
[22]Della Greca M,Di Marino C,Zarrelli A,et al.Isolation and phytotoxicity of apocarotenoids from Chenopodium album[J].J Nat Prod,2004,67(9):1492.
[23]Shirali A,Sriram M,Hall J J,et al.Development of synthetic methodology suitable for the radiosynthesis of combretastatin A-1(CA1)and its corresponding prodrug CA1P[J].J Nat Prod,2009,72(3):414.