仪花根、叶以及野八角果实化学成分的研究
详细信息    本馆镜像全文|  推荐本文 |  |   获取CNKI官网全文
摘要
仪花(Lysidicie rhodostegia)为豆科(Leguminosae)仪花属植物,产于我国广东、广西和云南等地。越南也有分布。本种根、茎、叶有小毒,能散瘀消肿,止血止痛。可治疗跌打损伤,骨折,风湿关节炎,外伤出血等症。前期本课题组从仪花根中分离得到多种结构类型的化合物,如间苯三酚类、二苯乙烯类、黄酮类、木脂素类等。其中,间苯三酚类化合物结构较为新颖,包括新骨架化合物。并且,大部分间苯三酚类化合物显示了一定的扩张血管或抗氧化的活性。
     利用LC-DAD、LC/ESI-MS、LC/ESI-MS~n和TLC等手段重点针对间苯三酚类化合物进行分离,从仪花根正丁醇部位以及再次采集的仪花根EtOAc部位中共分离得到9化合物,通过波谱和化学方法确定其结构为:仪花素I(W1)、仪花素J(W2)、仪花素K(W3)、(2S,3S,4S)-4-(3-异戊酰基-4-O-β-D-吡喃葡萄糖-2,6-二羟基苯基)-3,5,7,4′-四羟基黄烷(W4)、(2S,3S,4S)-4-(3-异戊酰基-4-O-β-D-吡喃葡萄糖-2,6-二羟基苯基)-3,5,7,3′,4′-五羟基黄烷(W5)、4-(3-异戊酰基-4-O-β-D-吡喃葡萄糖-2,6-二羟基苯基)-2,3-环氧-5,7,3′,4′-四羟基黄烷(W6)、间苯三酚1-异戊酰基-2-O-(6-O-没食子酰基)-β-D-吡喃葡萄糖苷(W7)、间苯三酚1-(2-甲基丁酰基)-2-O-β-D-吡喃葡萄糖苷(W8)和(E)-5,4′-二羟基二苯乙烯3-O-(6-O-没食子酰基)-β-D-吡喃葡萄糖苷(W9)。其中3个化合物(W1、W2和W3)为新骨架间苯三酚类衍生物,3个为天然产物中罕见的间苯三酚与黄烷3-醇的加合物(W4、W5和W6),1个为新的间苯三酚糖苷类化合物(W7),2个为首次从该属植物中分离得到的化合物(W8和W9)。同时,对3个新骨架化合物的生源途径进行了初步的推测和探讨。药理活性测试结果显示,化合物W1、W2和W3在高浓度(10~(-4) M)时表现一定的抗氧化活性,化合物W4~W7在10~(-4)、10~(-5)和10~(-6)M浓度时均表现较强的抗氧化活性,其活性强于阳性对照维生素E。此外,利用计算CD谱法(TD-DFT)和Mo_2(OAc)_4衍生化CD谱法,确定了前期从仪花根中分离得到的新骨架化合物仪花素D、仪花素E和仪花素F的绝对构型,解决了其他方法不能解决的该类新骨架化合物手性碳绝对构型的问题。
     利用LC-DAD,LC-ESI-MS~n等技术对仪花叶的化学成分进行在线结构分析,根据已有的几类化合物的质谱裂解规律,推测了21个成分的结构,它们分别是:虎杖苷(A1)、白藜芦醇3-O-β-D-吡喃木糖苷(A2)、槲皮素7-O-β-D-吡喃葡萄糖苷(A3)、槲皮素7-O-α-L-吡喃鼠李糖苷(A4)、3,5,7,4′-四羟基黄酮3-O-α-L-吡喃鼠李糖苷(A5)、间苯三酚1-异戊酰基-2-O-α-L-吡喃鼠李糖-(1→6)-β-D-吡喃葡萄糖苷(B1)、仪花苷A(B2)、3,5,7,4′-四羟基黄酮3-O-β-D-吡喃葡萄糖苷(B4)、3,5,7,4′-四羟基-8-异戊烯基-4′-O-没食子酰基-黄烷-3-O-没食子酸酯(C1)、3,5,7,3′,4′-五羟基-黄烷-3-O-没食子酸酯(C2)、3,5,7,3′,4′,5′-六羟基黄酮3-O-α-L-吡喃鼠李糖苷(C3)、木樨草素7-O-α-L-吡喃鼠李糖苷(C5)、槲皮素7-O-(2-O-没食子酰基)-α-L-吡喃鼠李糖苷(C6)、槲皮素3-O-β-D-吡喃葡萄糖-(1→2)-β-D-吡喃葡萄糖苷(D1)、3,5,7,4′-四羟基黄酮3-O-β-D-吡喃葡萄糖-(1→2)-β-D-吡喃葡萄糖苷(D2)、3,5,7,3′,4′,5′-六羟基黄酮7-O-α-L-吡喃鼠李糖苷(D3)、槲皮素3-O-α-L-吡喃鼠李糖基-7-O-β-D-吡喃葡萄糖苷(E1)、槲皮素3-O-α-L-吡喃鼠李糖基-7-O-α-L-吡喃鼠李糖苷(E4)、3,5,7,4′-四羟基-3′-甲氧基-黄酮3-O-β-D-吡喃葡萄糖基-7-O-α-L-吡喃鼠李糖苷(E5)、槲皮素3-O-α-L-吡喃鼠李糖苷(E7)和3,5,7,4′-四羟基-黄酮3-O-α-L-吡喃鼠李糖基-7-O-α-L-吡喃鼠李糖苷(E8)。
     野八角(Iliicium simonsii Maxim)为木兰科八角属(Illicium L.)植物,产于我国贵州、四川和云南以及印度、缅甸。叶、果实入药,味辛,性热。具有镇呕、行气止痛、生肌接骨、灭虱杀虫之功效,可治胃寒作呕、膀胱疝气、胸前胀痛、疥疮等症。利用LC/UV并结合TLC显色重点针对野八角果实中植物醌(异戊烯基取代的C6-C3)类化合物进行分离,得到19个化合物,其中植物醌类化合物12个,包括3个新化合物(W10~W12)。利用波谱手段鉴定了这些化合物的结构,它们分别为:4-epi-illicinone E-12-shikimate(W10)、3-hydroxyillifunone B(W11)、7-hydroxy-2,3-dehydro-11-epi-illifunone C(W12)、illoliganone H(W13)、illoliganone G(W14)、2-烯丙基-2-(3-甲基-2-丁烯基)-4,5-亚甲二氧基-3,5-二烯-1-酮(W15)、illoliganone E(W16)、illoliganone A(W17)、illicinone E(W18)、illifunone C(W19)、illifunone D(W20)、2,3-dehydroillifunone C(W21)、dihydrodehydrodiconifenyl alcohol(W22)、trans-3-羟甲基-5-(3-羟基丙基)-7-甲氧基-2-(3,4,5-三甲氧基苯基)-2,3-二氢苯并[b]呋喃(W23)、styraxlignolide C(W24)、7R,7R′,8S,8S-(+)-neo-olivil-4-O-β-D-glucopyranosde(W25)、(1R,2S,5R,6S)-6-(3,4-dihydroxyphenyl)-2-(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3,3,0]octane(W26)、(1R,2S,5R,6S)-6-(4-hydroxy-3-methoxyphenyl)-2-(3,4-dihydroxyphenyl)-3,7-dioxabicycio[3,3,0]octane(W27)和3,5,7-三羟基色原酮-3-O-β-D-吡喃木糖苷(W28)。
Lysidice rhodostegia belongs to the genus Lysidice in the family Fabaceae.Lysidice rhodostegia is widely distributed in Guangdong,Guangxi,Yunnan of China,and its roots have been used for the the treatment of ache,fractures and hemorrhage by local folks in China.Phloroglucinols,stilbenes,Flavonoids,lignans and triterpenoids have been isolated from the this plant.Among these constituents,phloroglucinols are a type of compounds with novel structures and antivasoconstriction and antioxidant activities.
     Nine compounds were obtained from the erthanol extract of the roots of Lysidice rhodostegia.On the basis of chemical and spectra analysises,these compouns were elucidated as lysicidin A(W1),lysicidin B(W2),lysicidin C(W3),(2S,3S,4S)-4-(3-isovisovaleryl -4-O-β-D-glucopyranosyl-2,6-dihydroxypheny1)-3,5,7,4'-tetrahydroxyflavan (W4),(2S,3S,4S)-4-(3-isovaleryl-4-O-β-D-glucopyranosyl-2,6-dihydroxyphenyl)-3,5,7, 3',4'-pentahydroxyflavan(WS),4-(3-isovaleryl-4-O-β-D-glucopyranosyl-2,6-dihydroxyphenyl) -2,3-epoxy-5,7,3',4'-tetrahydroxyflavan(W6),phloroglucinol 1-isovaleryl-2-O-(6-O-galloyl)-β-D-glucopyranoside(W7),phloroglucinol 1-(2-methylbutyryl)-2-O-β-D-glucopyranoside (W8),(E)-5,4'-dihydroxystilbene 3-O-(6-O-galloyl)-β-D-glucopyranoside (W9).Among them,W1~W3 are novel compounds,W4~W6 are compounds with rare structures from natural products,W7 is a new compound and W8,W9 were isolated from the plants of this genus for the first time.Meanwhile,the plausible pathways for the biosynthesis of novel compounds W1~W3 were postulated.Antioxidant activities of the isolated compounds were investigated.Compounds W4~W7 exhibited obvious antioxidant effect at low,middle and high concentrations,which was stronger than those of the positive control agent vitamin E.In addition,the absolute configurations of novel compounds lysidicin D,lysidicin E and lysidicin F,which were isolated previously from the roots of Lysidice rhodostegia,were determined by a solid-state CD/TDDFT approach and dimolybdenum method.
     The compoents in fractions from the leaves of Lysidice rhodostegia were investigated by HPLC-DAD/ESI-MS~n.As a result,the possible structures of 21 constituents were deduced.
     Iliicium simonsii belongs to the genus Illicium in the family Magnoliaceae.This plant was distributed in Guizhou,Sichuan,Yunnan of China and India,Burma.Its leaves and fruits have been used as Chinese folk medicine for the treatment of vomiting,chest pain,Hernia and scabies.19 compounds were isolated from 95%alcohol extract of the fruits of the plant.Among them,W10~W12 are new compounds.On the basis of spectroscopic methods,their structures were determined as 4-epi-illicinone E-12-shikimate(W10),3-hydroxyillifunone B(W11),7-hydroxy-2,3-dehydro-11-epi-illifunone C(W12),illoliganone H(W13),illoliganone G(W14),2-allyl-2-(3-methylbutenyl) -4,5-methylenedioxycyclohexa-3,5-dien-1-one(W15),illoliganone E(W16),illoliganone A(W17),illicinone E(W18),illifunone C(W19),illifunone D(W20), 2,3-dehydroillifunone C(W21),dihydrodehydrodiconifenyl alcohol(W22),trans-3-(hydrpxymethyl) -5-(3-hydroxypropyl)-7-methoxy-2-(3,4,5-trimethoxyphenyl)-2,3-dihydrob enzo[b]furan(W23),styraxlignolide C(W24),7R,7R',8S,8S-(+)-neo-olivil-4-O-β-D-glucopyranoside (W25),(1R,2S,5R,6S)-6-(3,4-dihydroxyphenyl)-2-(3,4-methylenedioxyphenyi) -3,7-dioxabicyclo[3,3,0]octane(W26),(1R,2S,5R,6S)-6-(4-hydroxy-3-methoxyphenyl) -2-(3,4-dihydroxxyphenyl)-3,7-dioxabicyclo[3,3,0]octane(W27),3,5,7-trihydroxylcchromone 3-O-β-D-xylpyranoside(W28).
引文
1.陈德昭,中国植物志.科学出版社:北京,1988;Vol.39,p203-206.
    2.郜嵩.单刀根活性成分的研究及菲骈吲哚里西啶类生物碱手性全合成的初步研究.博士研究生学位论文,中国医学科学院中国协和医科大学北京,2004.
    3.Gao,S.;Yu,S.S.;Yu,D.Q.,Two New Phloroglucinol Glycosides from Lysidice rhodostegia.Chin.Chem.Lett.,2004,15(3):313-315.
    4.Gao,S.;Feng,N.;Yu,S.S.;Yu,D.Q.;Wang,X.,Vasodilator constituents from the roots of Lysidice rhodostega.Planta Med.,2004,70(12):1128-34.
    5.Gao,S.;Liu,J.;Fu,G.M.;Hu,Y.C.;Yu,S.S.;Fan,L.H.;Yu,D.Q.;Qu,J.,Resveratrol/phloroglucinol glycosides from the roots of Lysidice rhodostegia.Planta Med.,2007,73(2):163-6.
    6.吴先富.单刀根活性成分的研究.硕士研究生论文,沈阳药科大学,沈阳,2006.
    7.杨华良.短萼仪花叶的化学成分研究.硕士研究生论文,沈阳药科大学,沈阳,2008.
    8.郜嵩;浮光苗;范丽华;庾石山;于德泉,单刀根化学成分的研究.中国天然药物,2005,3(3):144-147.
    9.胡友财.基于药理筛选和化学筛选的短萼仪花茎皮活性成分的研究.博士研究生学位论文,中国医学科学院北京协和医学院,北京,2008.
    10.Hu,Y.;Ma,S.;Li,J.;Yu,S.;Qu,J.;Liu,J.;Du,D.,Targeted Isolation and Structure Elucidation of Stilbene Glycosides from the Bark of Lysidice brevicalyx Wei Guided by Biological and Chemical Screening.J.Nat.Prod.,2008,71(11):1800-1805.
    11.Gao,S.;Fu,G.M.;Fan,L.H.;Yu,S.S.;Yu,D.Q.,Flavonoids from Lysidice rhodostegia Hance.Journal of Integrative Plant Biology,2005,47(6):759-763.
    12.杨华良;庾石山;裴月湖,短萼仪花叶化学成分研究.中国中药杂志,2008,33(22):2633-5.
    13.Hu,Y.C.;Wu,X.F.;Gao,S.;Yu,S.S.;Liu,Y.;Qu,J.;Liu,J.;Liu,Y.B.,Novel phloroglucinol derivatives from the roots of Lysidice rhodostegia.Org.Lett.,2006,8(11):2269-72.
    14.屈晶;方唯硕;庾石山;于德泉,新型结构活性天然产物的识别与获取新方法.中国天然药物,2008,6(1):6-12.
    15.靳朝东,色谱联用技术在检测植物药有效成分中的应用.国外医药·植物分册,2002,17(4):149-151.
    16.Qu,J.;Hu,Y.C.;Li,J.B.;Wang,Y.H.;Zhang,J.L.;Abliz,Z.;Yu,S.S.;Liu,Y.B.,Structural characterization of constituents with molecular diversity in fractions from Lysidice brevicalyx by liquid chromatography/diode-array detection/electrospray ionization tandem mass spectrometry and liquid chromatography/nuclear magnetic resonance.Rapid Commun,Mass Spectrom.,2008,22(6):755-65.
    17.张惠勤;徐庆;张勇;伍红艳;韦梦星,仪花抗心律失常作用的研究.中国医药科技,2005,12(4):229-230.
    1.Hu,Y.C.;Wu,X.F.;Gao,S.;Yu,S.S.;Liu,Y.;Qu,J.;Liu,J.;Liu,Y.B.Novel phloroglucinol derivatives from the roots of Lysidice rhodostegia.Org.Lett.,2006,8(11):2269-2272.
    2.Gao,S.;Yu,S.S.;Yu,D.Q.Two New Phloroglucinol Glycosides from Lysidice rhodostegia.Chin.Chem.Lett.,2004,15(3):313-315.
    3.Gao,S.;Feng,N.;Yu,S.S.;Yu,D.Q.;Wang,X.Vasodilator constituents from the roots of Lysidice rhodostega.Planta Med,2004,70(12):1128-1134.
    4.Gao,S.;Liu,J.;Fu,G.M.;Hu,Y.C.;Yu,S.S.;Fan,L.H.;Yu,D.Q.;Qu,J.Resveratrol/phloroglucinol glycosides from the roots of Lysidice rhodostegia.Planta Med.,2007,73(2):163-166.
    5.Zhang,P.C.;Xu,S.X.Flavonoid ketohexosefuranosides from the leaves of Crataegus pinnatifida Bge.var.major N.E.Br.Phytochemistry,2001,57(8):1249-1253.
    6.吴先富.单刀根活性成分的研究.硕士研究生论文,沈阳药科大学,沈阳,2006.
    7.Johnson,W.W.;Harris,T.M.;Guengerich,F.P.Kinetics and Mechanism of Hydrolysis of Aflatoxin B1 exo-8,9-Epoxide and Rearrangement of the Dihydrodiol.J.Am.Chem.Soc.,1996,118(35):8213-8220.
    8.Burrer,F.;Chulia,A.J.;Debelmas,A.M.Contribution to the study of the genus gentiana:2"-O-glucosides of isoorientine and isovitexine in Gentiana lutea L..Planta Med,1979,36(2):178-179.
    9.Kinjo,J.;Araki,K.;Fukui,K.;Higuchi,H.;Ikeda,T.;Nohara,T.;Ida,Y.;Takemoto,N.;Miyakoshi,M.;Shoji,J.Six new triterpenoidal glycosides including two new sapogenols from Albizziae Cortex.V.Chem.Pharm.Bull.,1992,40(12):3269-3273.
    10.Botha,J.J.;Young,D.A.;Ferreira,D.;Roux,D.G.Synthesis of Condensed Tannins.Part 1.Stereoselective and Stereospecific Syntheses of Optically Pure 4-Arylflavan-3-ols,and Assessment of their Absolute Stereochemistry at C-4 by means of Circular Dichroism.J.Chem.Soc.,Perkin Trans.1,1981:1213-1219.
    11.Kolodziej,H.The first naturally occurring 4-aryl flavan-3-ol.Tetrahedron Lett.,1983,24(17):1825-1828.
    12.Pieter W.Van Zyl,J.P.S.E.V.B.D.F.Spectroscopic properties of free phenolic 4-arylflavan-3--ols as models for natural condensed tannins.Magn.Reson.Chem.,1993,31(12):1057-1063.
    13.Westhuizen,J.H.v.d.;Ferreira,D.;Roux,D.G.Synthesis of Condensed Tannins.Part 2.Synthesis by Photolytic Rearrangement,Stereochemistry.and Circular Dichroism of the First 2,3-cis-3,4-cis-4-Arylf lavan-3-01s.J Chem Soc Perkin Trans Ⅰ,1981:1220-1226.
    14.Preeza,I.C.D.;Rowan,C.;Roux,D.G.Hindered Rotation About the sp-sp~3 Hybridized C-C Bond Between Flavanoid Units in Condensed Tannins.Chem.Commun.,1971:315-316.
    15.Ramos,F.A.;Takaishi,Y.;Shirotori,M.;Kawaguchi,Y.;Tsuchiya,K.;Shibata,H.;Higuti,T.;Tadokoro,T.;Takeuchi,M.Antibacterial and antioxidant activities of quercetin oxidation products from yellow onion(Allium cepa) skin.J Agric Food Chem,2006,54(10):3551-3557.
    16.Ling,S.K.;Tanaka,T.;Kouno,I.New cyanogenic and alkyl glycoside constituents from Phyllagathis rotundifolia.J.Nat.Prod.,2002,65(2):131-135.
    17.Kosasi,S.;Van Der Sluis,W.G.;Labadie,R.Muitifidol and multifidol glucoside from the latex of Jatropha multifida.Phytochemistry,1989,28(9):2439-2441.
    18.Okasaka,M.;Takaishi,Y.;Kogure,K.;Fukuzawa,K.;Shibata,H.;Higuti,T.;Honda,G.;Ito,M.;Kodzhimatov,O.K.;Ashurmetov,O.New stilbene derivatives from Calligonum leucocladum.J.Nat.Prod.,2004,67(6):1044-1046.
    19.Zuurbier,K.W.M.;Fung,S.-Y.;Scheffer,J.J.C.;Verpoorte,R.In-vitro prenylation of aromatic intermediates in the biosynthesis of bitter acids in humulus lupulus.Phytochemistry,1998,49(8):2315-2322.
    20.Schmidt,T.J.;Vossing,S.;Klaes,M.;Grimme,S.An aryldihydronaphthalene lignan with a novel type of ring system and further new lignans from linum perenne L.Planta Med.,2007,73(15):1574-1580.
    21.Krick,A.;Kehraus,S.;Gerhauser,C.;Klimo,K.;Nieger,M.;Maier,A.;Fiebig,H.H.;Atodiresei,I.;Raabe,G.;Fleischhauer,J.;Konig,G.M.Potential cancer chemopreventive in vitro activities of monomeric xanthone derivatives from the marine algicolous fungus Monodictys putredinis.J.Nat.Prod.,2007,70(3):353-360.
    22.Karsten Krohn,I.K.B.E.U.F.B.S.S.D.G.P.S.A.T.K.Bioactive Natural Products from the Endophytic Fungus Ascochyta sp.from Meliotus dentatus - Configurational Assignment by Solid-State CD and TDDFT Calculations.Eur.J.Org.Chem.,2007,(7):1123-1129.
    23.Goel,A.;Singh,F.V.;Kumar,V.;Reichert,M.;Guider,T.A.;Bringmann,G.Synthesis,optical resolution,and configurational assignment of novel axially chiral quateraryls.J.Org.Chem.,2007,72(20):7765-7768.
    24.Holscher,D.;Reichert,M.;Gorls,H.;Ohlenschlager,O.;Bringmann,G.;Schneider,B.Monolaterol,the first configurationally assigned phenylphenalenone derivative with a stereogenic center at C-9,from Monochoria elata.J.Nat.Prod.,2006,69(11):1614-1617.
    25.Bringmann,G.;Lang,G.;Maksimenka,K.;Hamm,A.;Gulder,T.A.;Dieter,A.;Bull,A.T.;Stach,J.E.;Kocher,N.;Muller,W.E.;Fiedler,H.P.Gephyromycin,the first bridged angucyclinone,from Streptomyces griseus strain NTK 14.Phytochemistry,2005,66(11):1366-1373.
    26.Sandstrom,J.Determination of absolute configurations and conformations of organic compounds by theoretical calculations of CD spectra.Chirality,2000,12(4):162-171.
    27.Zhang,W.;Krohn,K.;Ding,J.;Miao,Z.H.;Zhou,X.H.;Chen,S.H.;Pescitelli,G.;Salvadori,P.;Kurtan,T.;Guo,Y.W.Structural and stereochemical studies of alpha-methylene-gamma-lactone-bearing cembrane diterpenoids from a south china sea soft coral Lobophytum crassum.J.Nat.Prod.,2008,71(6):961-966.
    28.Gorecki,M;Jablonska,E.;Kruszewska,A.;Suszczynska,A.;Urbanczyk-Lipkowska,Z.;Gerards,M.;Morzycki,J.W.;Szczepek,W.J.;Frelek,J.Practical method for the absolute configuration assignment of tert/tert 1,2-diols using their complexes with Mo2(OAc)4.J.Org.Chem.,2007,72(8):2906-2916.
    29.Gorecki,M.;Kaminska,A.;Ruskowska,P.;Suszczynska,A.;Frelek,J.Dimolybdenum method for determination of the absolute configuration of vic-diols:Foundations and developments.Poi.J.Chem.,2006,80(4):523-534.
    30.Frelek,J.;Klimek,A.;Ruskowska,P.Dinuclear Transition Metal Complexes as Auxiliary Chromophores in Chiroptical Studies on Bioactive Compounds.Curr.Org.Chem.,2003,7(11):1081-1104.
    1.陈德昭,中国植物志.科学出版社:北京,1988;Vol.39,p203-206.
    2.屈晶.格木中具有细胞毒活性的化学成分研究 格木中微量咖萨因型酰胺和短萼仪花中化学成分的在线分析方法研究.博士研究生论文,中国医学科学院中 国协和医科大学,北京,2007.
    3.阿布拉江·克依木.黄酮苷类天然产物的质谱分析方法研究.博士研究生论文,中国医学科学院 中国协和医科大学,北京,2006.
    4.郜嵩.单刀根活性成分的研究及菲骈吲哚里西啶类生物碱手性全合成的初步研究.博士研究生学位论文,中国医学科学院中国协和医科大学 北京,2004.
    1.林祁.八角属药用植物资源.中草药,2002,33(7):654-657.
    2.黄建梅;杨春澍.八角科植物化学成分和药理研究概况.中国药学杂志,1998,33(6):321-327.
    3.唐文照.少药八角果实及茎皮中化学成分和药理活性研究.博士研究生学位论文,中国医学科学院北京协和医学院,北京,2007.
    4.马双刚.亮叶围涎树根中具有细胞毒活性的三萜苷成分研究 少药八角根的化学成分及其生物活性研究.博士研究生学位论文,中国医学科学院北京协和医学院,北京,2008.
    5.Kouno,I.;Shimamoto,S.;Jiang,Z.-H.;Tanaka,T.Prenylated C6-C3 compounds from root bark of Illicium anisatum.Phytochemistry,1997,46(8):1389-1392.
    6.Talapatra,B.;Das,A.K.;Talapatra,S.K.Defuscin,a new phenolic ester from Dendrobium fuscescens:Conformation of shikimic acid.Phytochemistry,1989,28(1):290-292.
    7.Snyder,C.D.;Rapoport,H.Stereochemistry of quinate-shikimate conversions.Synthesis of (-)-4-epi-shikimic acid.J.Am.Chem.Sac.,1973,95(23):7821-7828.
    8.Fukuyama,Y.;Shida,N.;Sakurai,T.;Kodama,M.Prenylated C6-C3 compounds from Illicium tashiroi.Phytochemistry,1992,31(11):3975-3979.
    9.Yakushijin,K.;Tohshima,T.;Kitagawa,E.;Suzuki,R.;Sekikawa,J.;Morishita,T.;Murata,H.;Lu,S.T.;Furukawa,H.Studies on the Constituents of the Plants of Illicium Species.Ⅲ..Chem.Pharm.Bull.,1984,32(1):11-22.
    10.Fukuyama,Y.;Shida,N.;Hata,Y.;Kodama,M.Prenylated C6-C3 compounds from Illicium tashiroi.Phytochemistry,1994,36(6):1497-1503.
    11.Sato,S.;Obara,H.;Kumazawa,T.;Onodera,J.;Furuhata,K.Synthesis of(+),(-)-Model Compounds and Absolute Configuration of Carthamin;A Red Pigment in the Flower Petals of Safflower.Chem.Lett.,1996,10:833-834.
    12.Yakushijin,K.;Tohshima,T.;Suzuki,R.;Murata,H.;Lu,S.T.;Furukawa,H.Studies on the constituents of the plants of illicium species.Ⅱ.Structures of phenolic components.Chem.Pharm.Bull.,1983,31(8):2879-2883.
    13.Fukuyama,Y.;Nakahara,M.;Minami,H.;Kodama,m.Two New Benzofuran-Tape Lignans from the Wood of Viburnum awabuki.Chem.Pharm.Bull.,1996,44(7):1418-1420.
    14.Garcia-Munoz,S.;alvarez-Corral,M.;Jimenez-Gonzalez,L.;Lopez-Sanchez,C.;Rosales,A.;Munoz-Dorado,M.;Rodriguez-Garcia,I.Synthesis of dihydrodehydrodiconiferyl alcohol and derivatives through intramolecular C-H insertion.Tetrahedron,2006,62(52):12182-12190.
    15.Min,B.S.;Na,M.K.;Oh,S.R.;Ahn,K.S.;Jeong,G.S.;Li,G;Lee,S.K.;Joung,H.;Lee,H.K.New Furofuran and Butyrolactone Lignans with Antioxidant Activity from the Stem Bark of Styrax japonica.J.Nat.Prod.,2004,67(12):1980-1984.
    16.Kikuchi,M.;Kikuchi,M.Studies on the Constituents of Swertia japonica MAKINO Ⅱ.On the Structures of New Glycosides.Chem.Pharm.Bull.,2005,53(1):48-51.
    17.Nakai,M.;Harada,M.;Nakahara,K.;Akimoto,K.;Shibata,H.;Miki,W.;Kiso,Y.Novel Antioxidative Metabolites in Rat Liver with Ingested Sesamin.J.Agr.Food Chem.,2003,51(6):1666-1670.
    18.Coo,Z.Z.;Yi,Y.J.;Coo,Y.A new Chrome glycoside from smilax glabra roxb.Chin.Chem.Lett.,1995,6(7):587.
    19.冯子明;王映红;张培成.马银花的化学成分研究.药学学报,2005,40(2):150-152.

© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号

地址:北京市海淀区学院路29号 邮编:100083

电话:办公室:(+86 10)66554848;文献借阅、咨询服务、科技查新:66554700