阿卡如化学成分研究
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摘要
目的:研究阿卡如的化学成分。方法:采用现代分离方法和色谱技术,对阿卡如乙酸乙酯部位进行分离纯化,采用波谱技术和理化常数对照等方法进行结构鉴定。结果:从阿卡如乙酸乙酯部分分离并鉴定了6个含量相对较高的化合物,分别为3,4-Di-(3-methoxy-4-hydroxyphenyl)tetrahydrofuran(1),开环异落叶松树脂酚(2),3,3'-dimethoxy-8,9-epoxylign-4,4',9'-triol(3),2S,3S,4S-2-羟基-3,4-二-(3,甲氧基-4-羟基苄基)四氢呋喃(4),2-(3,4-次甲二氧基苄基)-3-(3-甲氧基-4-羟基苄基)-1,4-丁二醇(5),2R,3S,4S-2-羟基-3,4-二-(3,4-次甲二氧基苄基)四氢呋喃(6)。结论:首次从该种植物中分离得到化合物1、2、3、5,首次从该植物主干和根中分离得到化合物4和6。
Objective: To study chemical ingredients of akaru. Methods: By adopting modern separation method and chromatographic technique, the part of acetic ether was separated and purified from akaru, and the structure was identified by spectrum technique and physicochemical constant control method. Results: The part of acetic ether was isolated from akaru, and six compounds in higher contents relatively were identified, they were 3,4-Di-(3-methoxy-4-hydroxyphenyl)tetrahydrofuran(1), Secoisolariciresinol(2), 3, 3'-dimethoxy-8, 9-epoxylign-4, 4',9'-triol(3), 2 S, 3 S, 4 S-2-Hydroxy-3, 4-di-(3-methoxy-4-hydroxyphenyl) tetrahydrofuran, 2-(3, 4-Methylenedioxybenzyl)-3-(3-methoxy-4-hydroxyphenyl)-1, 4-butanediol(5), 2 R, 3 S, 4 S-2-Hydroxy-3, 4-di-(3, 4-Methylenedioxybenzyl)tetrahydrofuran(6) respectively. Conclusion: Compounds 1, 2, 3 and 5 are separated from akaru initially, compounds 4 and 6 from the plant stem and roots for the first time.
Objective: To study chemical ingredients of akaru. Methods: By adopting modern separation method and chromatographic technique, the part of acetic ether was separated and purified from akaru, and the structure was identified by spectrum technique and physicochemical constant control method. Results: The part of acetic ether was isolated from akaru, and six compounds in higher contents relatively were identified, they were 3,4-Di-(3-methoxy-4-hydroxyphenyl)tetrahydrofuran(1), Secoisolariciresinol(2), 3, 3'-dimethoxy-8, 9-epoxylign-4, 4',9'-triol(3), 2 S, 3 S, 4 S-2-Hydroxy-3, 4-di-(3-methoxy-4-hydroxyphenyl) tetrahydrofuran, 2-(3, 4-Methylenedioxybenzyl)-3-(3-methoxy-4-hydroxyphenyl)-1, 4-butanediol(5), 2 R, 3 S, 4 S-2-Hydroxy-3, 4-di-(3, 4-Methylenedioxybenzyl)tetrahydrofuran(6) respectively. Conclusion: Compounds 1, 2, 3 and 5 are separated from akaru initially, compounds 4 and 6 from the plant stem and roots for the first time.
引文
[1]张树军,张军锋,王金兰.紫丁香树皮的化学成分研究[J].中草药,2006,37(11):1624-1626.
[2]中国科学院西北高原生物研究所.藏药志[M].西宁:青海人民出版社,1991:452-454.
[3]帝玛尔·丹增彭措.晶珠本草[M].上海:上海科学技术出版社,1986:110.
[4]张军锋,焦华,王金兰,等.紫丁香树皮的化学成分研究(Ⅱ)[J].天然产物研究与开发,2007,19(4):617-619.
[5]尉小慧,张淑霞,翟卫峰,等.RP-HPLC同时测定不同采集地紫丁香树枝中丁香苷和橄榄苦苷的含量[J].中国药学杂志,2009,44(3):176-178.
[6]Ao WL,Bao XH,Wu XL,et al.Lignans from syringa pinnatifolia hemsl Var.alashanensis[J].Journal of Asian Natural Products Research,2012,14(4):396-400.
[7]XIE LH,Akao T,Hamasaki K,et al.Biotransformation of pinoresinol diglucoside to mammalian lignans by human intestinal microflora,and isolation of enterococcus faecalis strain PDG-1 responsible for the transformation of(+)-Pinoresinol to(+)-Lariciresinol[J].Chem Pharm Bull,2003,51(5):508-515.
[8]Shi YM,Zhong WM,Chen H,et al.New lignans from the leaves and stems of schisandra chinensis and their anti-HIV-1 activities[J].Chin J Chem,2014,32:734-740.
[9]Barrero AF,Haidour A,Munoz Dorado M.Lignans from the wood of abies pinsapo[J].Journal of Natural Products,1994,57(6):713-719.
[10]Chen YC,Liao CH,Chen IS.Lignans,an amide and antiplatelet activities from piper philippinum[J].Phytochemistry,2007,68(6):2101-2111.
[11]De Pascoli IC,Nascimento IR.Configurational analysis of cubebins and bicubebin from aristolochia lagesiana and aristolochia pubescens[J].Phytochemistry,2006,67(7):735-742.
[12]赵小静.蒙药山沉香化学成分及生物活性初步研究[D].武汉:华中科技大学,2011.
[13]颜彦.蒙药山沉香挥发油成分分析及抗心肌缺血作用研究[D].武汉:华中科技大学,2011.
[14]Banskota AH,Nguyen NT,Tezuka Y,et al.Secoisolariciresinol and isotaxiresinol inhibit tumor necrosis factor-alpha-dependent hepatic apoptosis in mice[J].Life Sci,2004,74(22):2781-2792.
[15]Chen J,Saggar JK,Corey P,et al.Flaxseed and pure secoisolariciresinol diglucoside,but not flaxseed hull,reduce human breast tumor growth(MCF-7)in athymic mice[J].J Nutr,2009,139(11):2061-2066.
[16]Prasad K.Secoisolariciresinol diglucoside from flaxseed delays the development of type 2 diabetes in Zucker rat[J].J Lab Clin Med,2001,138(1):32-39.
[17]Prasad K,Mantha SV,Muir AD,et al.Protective effect of secoisolariciresinol diglucoside against streptozotocin-induced diabetes and its mechanism[J].Mol Cell Biochem,2000,206(1/2):141-149.
[18]Prasad K.Hydroxyl radical-scavenging property of secoisolariciresinol diglucoside(SDG)isolated from flax-seed[J].Mol Cell Biochem,1997,168(1/2):117-123.
[19]Kitts DD,Yuan YV,Wijewickreme AN,et al.Antioxidant activity of the flaxseed lignansecoisolariciresinol diglycoside and its mammalian lignan metabolites enterodiol and enterolactone[J].Mol Cell Biochem,1999,202(1/2):91-100.
[20]Penumathsa SV,Koneru S,Thirunavukkarasu M,et al.Secoisolariciresinol diglucoside:relevance to angiogenesis and cardioprotection against ischemiareperfusion injury[J].J Pharmacol Exp Ther,2007,320(2):951-959.
[21]Penumathsa SV,Koneru S,Zhan L,et al.Secoisolariciresinol diglucoside induces neovascularizationmediated cardioprotection against ischemia-reperfusion injury in hypercholesterolemic myocardium[J].J Mol Cell Cardio,2008,44(1):170-179.
[2]中国科学院西北高原生物研究所.藏药志[M].西宁:青海人民出版社,1991:452-454.
[3]帝玛尔·丹增彭措.晶珠本草[M].上海:上海科学技术出版社,1986:110.
[4]张军锋,焦华,王金兰,等.紫丁香树皮的化学成分研究(Ⅱ)[J].天然产物研究与开发,2007,19(4):617-619.
[5]尉小慧,张淑霞,翟卫峰,等.RP-HPLC同时测定不同采集地紫丁香树枝中丁香苷和橄榄苦苷的含量[J].中国药学杂志,2009,44(3):176-178.
[6]Ao WL,Bao XH,Wu XL,et al.Lignans from syringa pinnatifolia hemsl Var.alashanensis[J].Journal of Asian Natural Products Research,2012,14(4):396-400.
[7]XIE LH,Akao T,Hamasaki K,et al.Biotransformation of pinoresinol diglucoside to mammalian lignans by human intestinal microflora,and isolation of enterococcus faecalis strain PDG-1 responsible for the transformation of(+)-Pinoresinol to(+)-Lariciresinol[J].Chem Pharm Bull,2003,51(5):508-515.
[8]Shi YM,Zhong WM,Chen H,et al.New lignans from the leaves and stems of schisandra chinensis and their anti-HIV-1 activities[J].Chin J Chem,2014,32:734-740.
[9]Barrero AF,Haidour A,Munoz Dorado M.Lignans from the wood of abies pinsapo[J].Journal of Natural Products,1994,57(6):713-719.
[10]Chen YC,Liao CH,Chen IS.Lignans,an amide and antiplatelet activities from piper philippinum[J].Phytochemistry,2007,68(6):2101-2111.
[11]De Pascoli IC,Nascimento IR.Configurational analysis of cubebins and bicubebin from aristolochia lagesiana and aristolochia pubescens[J].Phytochemistry,2006,67(7):735-742.
[12]赵小静.蒙药山沉香化学成分及生物活性初步研究[D].武汉:华中科技大学,2011.
[13]颜彦.蒙药山沉香挥发油成分分析及抗心肌缺血作用研究[D].武汉:华中科技大学,2011.
[14]Banskota AH,Nguyen NT,Tezuka Y,et al.Secoisolariciresinol and isotaxiresinol inhibit tumor necrosis factor-alpha-dependent hepatic apoptosis in mice[J].Life Sci,2004,74(22):2781-2792.
[15]Chen J,Saggar JK,Corey P,et al.Flaxseed and pure secoisolariciresinol diglucoside,but not flaxseed hull,reduce human breast tumor growth(MCF-7)in athymic mice[J].J Nutr,2009,139(11):2061-2066.
[16]Prasad K.Secoisolariciresinol diglucoside from flaxseed delays the development of type 2 diabetes in Zucker rat[J].J Lab Clin Med,2001,138(1):32-39.
[17]Prasad K,Mantha SV,Muir AD,et al.Protective effect of secoisolariciresinol diglucoside against streptozotocin-induced diabetes and its mechanism[J].Mol Cell Biochem,2000,206(1/2):141-149.
[18]Prasad K.Hydroxyl radical-scavenging property of secoisolariciresinol diglucoside(SDG)isolated from flax-seed[J].Mol Cell Biochem,1997,168(1/2):117-123.
[19]Kitts DD,Yuan YV,Wijewickreme AN,et al.Antioxidant activity of the flaxseed lignansecoisolariciresinol diglycoside and its mammalian lignan metabolites enterodiol and enterolactone[J].Mol Cell Biochem,1999,202(1/2):91-100.
[20]Penumathsa SV,Koneru S,Thirunavukkarasu M,et al.Secoisolariciresinol diglucoside:relevance to angiogenesis and cardioprotection against ischemiareperfusion injury[J].J Pharmacol Exp Ther,2007,320(2):951-959.
[21]Penumathsa SV,Koneru S,Zhan L,et al.Secoisolariciresinol diglucoside induces neovascularizationmediated cardioprotection against ischemia-reperfusion injury in hypercholesterolemic myocardium[J].J Mol Cell Cardio,2008,44(1):170-179.