地榆水溶性化学成分研究(Ⅱ)
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摘要
目的研究地榆Sanguisorba officinalis水溶性化学成分。方法采用大孔树脂(D101、HP-20)、透析袋、Toyopearl HW-40、反相硅胶RP18等柱色谱方法进行分离纯化,并运用1H-NMR、~(13)C-NMR、ESI-MS等多种波谱方法对化合物进行结构鉴定。结果从地榆10%乙醇部位中分离并鉴定了25个化合物,分别为4-(4′-hydroxyphenyl)-2-butanone-4′-O-β-Dglucopyranoside(1)、phenethanol-β-vicianoside(2)、junipetrioloside A(3)、citroside A(4)、corchoionoside C(5)、adenosine(6)、tryptophan(7)、tachinoside(8)、d-mandelicacid-β-D-glucopyranoside(9)、(+)-(7S,8S)-guaiacylglycerol8-O-β-Dglucopyranoside(10)、biophenol(11)、3,5-dihydroxyphenethyl alcohol 3-O-β-glucopyranoside(12)、syringin(13)、(2E,5E)-3,7-dimethyl-2,5-octadiene-1,7-diol(14)、(±)-3-hydroxy-3,7-dimethyloct-6-enoic acid(15)、(2Z)-2,6-dimethyl-2,7-octadiene-1,6-diol(16)、phlorizin(17)、(+)-cyclo-olivil-6-O-β-D-glucopyranoside(18)、5′-methoxy-8′-hydroxyl-(+)-isolariciresinol-4′-O-β-Dglucopyranoside(19)、phenethyl-6-O-α-L-arabinofuranosyl-β-D-glucoside(20)、gaultherin(21)、benzyl-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (22)、(2E)-7-hydroxy-3,7-dimethyl-2-octenyl-6-O-α-L-arabinofuranosyl-β-D-glucopyranoside (23)、3,3′,4′-tri-O-methylellagic acid(24)、methyl-4-(β-D-glucopyranosyloxy)-3-hydroxy-5-methoxybenzoate(25)。结论化合物1～22为首次从该植物中分离得到。
Objective To study the chemical constituents in extract of Sanguisorba officinalis. Methods Compounds were isolated from 10% ethanol extracts by Macroporous resin(D101, HP-20), dialysis bag, reversed phase silica gel(RP-8, RP-18), Toyopearl HW-40 column chromatography and their structures were elucidated by NMR and MS data. Results Twenty-five compounds were isolated and their structures were elucidated as 4-(4′-hydroxyphenyl)-2-butanone-4′-O-β-D-glucopyranoside(1), phenethanol-β-vicianoside(2), junipetrioloside A(3), citroside A(4), corchoionoside C(5), adenosine(6), tryptophan(7), tachinoside(8), d-mandelic acid-β-D-glucopyranoside(9),(+)(7 S,8 S)-guaiacylglycerol 8-O-β-D-glucopyranoside(10), biophenol(11), 3,5-dihydroxyphenethyl alcohol 3-O-β-glucopyranoside(12), syringin(13),(2 E,5 E)-3,7-dimethyl-2,5-octadiene-1,7-diol(14),(±)-3-hydroxy-3,7-dimethyloct-6-enoic acid(15),(2 Z)-2,6-dimethyl-2,7-octadiene-1,6-diol(16), phlorizin(17),(+)-cyclo-olivil 6-O-β-D-glucopyranoside(18),5′-methoxy-8′-hydroxyl-(+)-isolariciresinol-4′-O-β-D-gluco-pyranoside(19), phenethyl 6-O-α-L-arabinofuranosyl-β-D-glucoside(20), gaultherin(21), benzyl-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside(22),(2 E)-7-hydroxy-3,7-dimethyl-2-octenyl6-O-α-L-arabinofuranosyl-β-D-glucopyranoside(23), 3,3′,4′-tri-O-methylellagic acid(24), and methyl-4-(β-D-glucopyranosyloxy)-3-hydroxy-5-methoxybenzoate(25). Conclusion Compounds 1—22 were isolated from this plant for the first time.
Objective To study the chemical constituents in extract of Sanguisorba officinalis. Methods Compounds were isolated from 10% ethanol extracts by Macroporous resin(D101, HP-20), dialysis bag, reversed phase silica gel(RP-8, RP-18), Toyopearl HW-40 column chromatography and their structures were elucidated by NMR and MS data. Results Twenty-five compounds were isolated and their structures were elucidated as 4-(4′-hydroxyphenyl)-2-butanone-4′-O-β-D-glucopyranoside(1), phenethanol-β-vicianoside(2), junipetrioloside A(3), citroside A(4), corchoionoside C(5), adenosine(6), tryptophan(7), tachinoside(8), d-mandelic acid-β-D-glucopyranoside(9),(+)(7 S,8 S)-guaiacylglycerol 8-O-β-D-glucopyranoside(10), biophenol(11), 3,5-dihydroxyphenethyl alcohol 3-O-β-glucopyranoside(12), syringin(13),(2 E,5 E)-3,7-dimethyl-2,5-octadiene-1,7-diol(14),(±)-3-hydroxy-3,7-dimethyloct-6-enoic acid(15),(2 Z)-2,6-dimethyl-2,7-octadiene-1,6-diol(16), phlorizin(17),(+)-cyclo-olivil 6-O-β-D-glucopyranoside(18),5′-methoxy-8′-hydroxyl-(+)-isolariciresinol-4′-O-β-D-gluco-pyranoside(19), phenethyl 6-O-α-L-arabinofuranosyl-β-D-glucoside(20), gaultherin(21), benzyl-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside(22),(2 E)-7-hydroxy-3,7-dimethyl-2-octenyl6-O-α-L-arabinofuranosyl-β-D-glucopyranoside(23), 3,3′,4′-tri-O-methylellagic acid(24), and methyl-4-(β-D-glucopyranosyloxy)-3-hydroxy-5-methoxybenzoate(25). Conclusion Compounds 1—22 were isolated from this plant for the first time.
引文
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[23]杨丹,谢海辉.法兰地草莓的芳香类和黄酮类成分[J].热带亚热带植物学报,2017,25(6):617-624.
[24]Wang C,Zhang T T,Du G H,et al.Synthesis and anti-nociceptive and anti-inflammatory effects of gaultherin and its analogs[J].J Asian Nat Prods Res,2011,13(9):817-825.
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[26]Su X D,Ali I,Arooj M,et al.Chemical constituents from Sanguisorba officinalis L.and their inhibitory effects on LPS-stimulated pro-inflammatory cytokine production in bone marrow-derived dendritic cells[J].Arch Pharmacal Res,2018,41(5):497-505.
[27]Ye G,Peng H,Fan M,et al.Ellagic acid derivatives from the stem bark of Dipentodon sinicus[J].Chem Nat Compds,2007,43(2):125-127.
[2]王丽娜,韩雪花,李小华,等.地榆正丁醇部位化学成分研究[J].中药材,2018,41(9):1856-1859.
[3]Wang L N,Qin L L,He J L,et al.Aryl-tetralin-type lignan isolated from Sanguisorba officinalis[J].J Asian Nat Prods Res,2018,doi:10.1080/10286020.2018.1487957.
[4]Gao L,Xu X,Yang J.Chemical constituents of the roots of Rheum officinale[J].Chem Nat Compds,2013,49(4):603-605.
[5]Wang L B,Wang J W,Wang C,et al.Chemical constituents in the lipid-lowering fraction of flos Helichrysum arenarium(III)[J].Chin J Med Chem,2012,22(3):220-226.
[6]Comte G,Vercauteren J,Chulia A J,et al.Phenylpropanoids from leaves of Juniperus phoenicea[J].Phytochemistry,1997,45(8):1679-1682.
[7]Hou Y,Chen K,Deng X,et al.Anti-complementary constituents of Anchusa italica[J].Nat Prod Res,2017,31(21):2572-2574.
[8]Yoshikawa M,Shimada H,Saka M,et al.Medicinal foodstuffs.V.Moroheiya.(1):Absolute stereostructures of corchoionosides A,B,and C,histamine release inhibitors from the leaves of Vietnamese Corchorus olitorius L.(Tiliaceae)[J].Chem Pharm Bull,1997,45(3):464-469.
[9]Xue P,Liang H,Wang B,et al.Chemical constituents from Potentilla multifida L.[J].J Chin Pharm Sci,2005,14(2):86-88.
[10]Lee M,Phillips R S.Fluorine substituent effects for tryptophan in 13C nuclear magnetic resonance[J].Mag Res Chem,1992,30(11):1035-1040.
[11]Su D M,Tang W Z,Yu S S,et al.Water-soluble constituents from roots of Capparis tenera[J].J Chin Mater Med,2008,33(9):1021-1023.
[12]Kitajima J,Tanaka Y.Constituents of Prunus zippeliana leaves and branches[J].Chem Pharm Bull,1993,41(11):2007-2009.
[13]Gan M,Zhu C,Zhang Y,et al.Constituents from a water-soluble portion of ethanolic extract of Iodes cirrhosa[J].Chin J Chin Mater Med,2010,35(4):456-467.
[14]Abdel-Kader M S,Al-Taweel A M,El-Deeb K S.Bioactivity guided phytochemical study of Clematis hirsuta growing in Saudi Arabia[J].Nat Prod Sci,2008,14(1):56-61.
[15]Saracoglu I,Varel M,Harput U S,et al.Acylated flavonoids and phenol glycosides from Veronica thymoides subsp.pseudocinerea[J].Phytochemistry,2004,65(16):2379-2385.
[16]Wang Q,Zhou D,Wang M,et al.Chemical constituents of Suaeda salsa and their cytotoxic activity[J].Chem Nat Compd,2014,50(3):531-533.
[17]Knapp H,Straubinger M,Fornari S,et al.(S)-3,7-dimethyl-5-octene-1,7-diol and related oxygenated monoterpenoids from petals of Rosa damascena Mill[J].J Agric Food Chem,1998,46(5):1966-1970.
[18]Zhao J C,Li X M,Gloer J B,et al.First total syntheses and antimicrobial evaluation of penicimonoterpene,a marine-derived monoterpenoid,and its various derivatives[J].Marine Drugs,2014,12(6):3352-3370.
[19]Li W,Yang S Y,Yan X T,et al.NF-κB inhibitory activities of glycosides and alkaloids from Zanthoxylum schinifolium stems[J].Chem Pharm Bull,2014,62(2):196-202.
[20]Xiao H,Zu L,Li S,et al.Chemical constituents from dried fruits of Rubus chingii[J].Chin J Med Chem,2011,21(3):220-226.
[21]Sugiyama M,Nagayama E,Kikuchi M.Lignan and phenylpropanoid glycosides from Osmanthus asiaticus[J].Phytochemistry,1993,33(5):1215-1219.
[22]Yang Y,Liu Z,Feng Z,et al.Lignans from the root of Rhodiola crenulata[J].J Agric Food Chem,2012,60(4):964-972.
[23]杨丹,谢海辉.法兰地草莓的芳香类和黄酮类成分[J].热带亚热带植物学报,2017,25(6):617-624.
[24]Wang C,Zhang T T,Du G H,et al.Synthesis and anti-nociceptive and anti-inflammatory effects of gaultherin and its analogs[J].J Asian Nat Prods Res,2011,13(9):817-825.
[25]Fang X Y,Wang R R,Sun S W,et al.Chemical constituents from the leaves of Cistus parviflorus[J].JChin Pharm Sci,2018,27(1):40-50.
[26]Su X D,Ali I,Arooj M,et al.Chemical constituents from Sanguisorba officinalis L.and their inhibitory effects on LPS-stimulated pro-inflammatory cytokine production in bone marrow-derived dendritic cells[J].Arch Pharmacal Res,2018,41(5):497-505.
[27]Ye G,Peng H,Fan M,et al.Ellagic acid derivatives from the stem bark of Dipentodon sinicus[J].Chem Nat Compds,2007,43(2):125-127.