冷水七、中华猕猴桃根的物质基础研究
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摘要
本论文由三章组成。第一章为民族药冷水七抗类风湿关节炎药效物质基础研究,证实了冷水七的抗类风湿关节炎活性并筛选了活性部位,进行了化学成分研究并对单体化合物进行活性筛选。第二章为中华猕猴桃根保肝药效物质基础的初步研究,筛选了保肝降酶的活性部位并进行了化学成分研究。第三章为综述,对冷水七中含有的主要活性成分刺囊酸皂苷类化合物的化学结构和活性进行了文献综述,对猕猴桃属的化学成分也进行了综述。
第一章
冷水七(Impatiens pritzellii Hook. f. var. hupehensis Hook. f.)为凤仙花科凤仙花属植物,其根茎为湖北省土家族常用药材,用于治疗类风湿性关节炎(RA)。为了证实冷水七的抗RA作用以进一步扩大使用,为了筛选冷水七抗RA部位和活性成分以进一步开发新药,本研究对产于湖北恩施自治州的冷水七进行了系统的药理和化学成分研究。
本研究建立了RA的一种常见的整体动物病理模型:小牛II型胶原诱导的小鼠关节炎模型(CIA)。冷水七甲醇总膏和正丁醇部位对CIA小鼠的关节炎发展有明显的抑制作用,并都可有效降低小鼠血清中抗C II抗体水平,据此证实了冷水七具有明显抗RA作用,并确定活性部位为正丁醇部位,与我们前期研究的抗炎镇痛的活性部位一致。冷水七及其活性部位可以抑制CIA小鼠免疫器官重量,可以明显下调CIA小鼠体内促炎因子TNF-α、IFN-γ和IL-18水平,对抗炎因子IL-10有上调作用。因此推测冷水七抗RA可能的作用机理之一是其广泛地影响各种细胞因子水平,从而调节整个细胞因子网络的平衡。
本研究对冷水七进行了系统的化学成分研究,在冷水七各部位分离得到30个单体化合物,并鉴定为:刺囊酸(Comp. 1),刺囊酸-3-O-β-D-吡喃葡萄糖醛酸(Comp. 2),刺囊酸-3-O-β-D-吡喃葡萄糖醛酸甲酯苷(Comp. 3),刺囊酸-3-O-β-D-吡喃葡萄糖醛酸乙酯苷(Comp. 4)*,刺囊酸-3-O-β-D-吡喃葡萄糖醛酸丁酯苷(Comp. 5)*,刺囊酸葡萄糖醛酸丁酯-28-O-木糖-鼠李糖-木糖酯苷(Comp. 6)*,正丁基-β-D-吡喃果糖苷(Comp. 7), 5-羟甲基糠醛(Comp. 8),邻苯二甲酸二(2-乙基己基)酯(Comp. 9),大豆鞘苷I (Comp. 10),大豆鞘苷II (Comp. 11),败酱草碱(Comp. 12),三十一烷烃(Comp. 13),二十四烷酸甲酯(Comp. 14),棕榈酸(Comp. 15),硬脂酸(Comp. 16),硬脂酸甲酯(Comp. 17),α-菠甾醇(Comp. 18),菠甾酮(Comp. 19),乙酰菠甾醇(Comp. 20),菠甾醇-3-O-β-D-吡喃葡萄糖苷(Comp. 21),菠甾醇3β-棕榈酸酯(Comp. 22),菠甾醇-3-O-β-D-吡喃葡萄糖苷-6'-O-棕榈酸酯(Comp. 23),棕榈酸单甘油酯(Comp. 24),二十四烷酸单甘油酯(Comp. 25),α氨基葡萄糖(Comp. 26),β氨基葡萄糖(Comp. 27),β呋喃果糖(Comp. 28),α-吡喃果糖(1-2’)β-吡喃果糖(Comp. 29)和α-吡喃果糖1,2:2,3’β-吡喃果糖(Comp. 30)。其中Comp. 4~6为新化合物。在活性部位正丁醇部位分离得到的化合物有Comp. 1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 12, 18, 21, 24, 25共15个化合物。本研究以筛选抗RA活性成分为目的考察了从冷水七特别是其活性部位中分离得到的若干单体化合物的相关活性,涉及抗炎镇痛、免疫抑制等方面,特别是研究了受试化合物抑制IL-18的活性,最后用CIA小鼠关节炎模型检验筛选出的活性化合物。实验结果显示Comp. 3, 5, 6对二甲苯诱导的小鼠耳肿胀有明显抗炎作用,Comp. 5的高低剂量和Comp. 6的高剂量对醋酸诱发小鼠扭体有明显抑制作用,Comp. 1, 3, 5, 7, 12, 23对T淋巴细胞增殖有抑制作用,Comp. 1, 3, 4, 5, 7, 20, 23对B淋巴细胞增殖有抑制作用,Comp. 2和6对小鼠血清溶血值HC50有抑制作用,Comp. 1, 2, 6, 12, 26对LPS诱导人PBMCs产生的IL-18有明显的抑制活性。在最后小鼠CIA关节炎模型筛选中,考察了Comp. 5和6对CIA小鼠关节炎指数的影响,未发现明显抑制作用。通过本研究得出结论,冷水七的抗RA作用具有多靶点性,其作用机理也具有多重性。
第二章
中华猕猴桃(Actinidia chinensis Planch.)为猕猴桃科猕猴桃属植物,其根民间用于治疗肝炎及其他病症。我们对中华猕猴桃根进行了保肝药效物质基础的初步研究。
建立了CCl4引起的小鼠急性肝损伤模型,对中华猕猴桃根乙醇总膏及其不同极性部位进行了保肝降酶活性的筛选。实验结果表明多糖部位和乙酸乙酯部位具有一定的保肝降酶活性。为了有利于中华猕猴桃根多糖(ACPS)的进一步研究,我们对中华猕猴桃根乙醇总膏和水部位进行了多糖的含量测定。
本研究对中华猕猴桃根进行了系统的化学成分研究,在各部位分离得到31个单体化合物,并鉴定30个化合物:2α,3β-dihydroxyurs-12-en-28,30-olide* (化合物1), 2α,3β,24-trihydroxyurs-12-en-28,30-olide* (化合物2),齐墩果酸(化合物3),表科罗索酸(化合物4), 2α,3α,24-trihydroxyurs-12-en-28-oic acid (化合物5), 23-hydroxyursolic acid (化合物6),积雪草酸(化合物7), 2α,3α,19,24- tetrahydroxyurs-12-en-28-oic acid (化合物8), 3β-hydroxyurs-12,18-dien-28-oic acid (化合物9), 2α,23 dihydroxylmicromeric acid (化合物10),香草酸(化合物11),邻苯二甲酸二(2-乙基己基)酯(化合物12), tachioside (化合物13), isotachioside (化合物14), 5-hydroxy-6-methoxy-7-O-β-D-glucosyl coumarin (化合物15), 1-O-(β-D-glucosyl)-2-[2-methoxy-4-(ω-hydroxypropyl)-phenoxy]-propan-3-ol (化合物16),表-儿茶素(化合物17), (+)-儿茶素(化合物18),鸟嘧啶(化合物19),腺嘌呤(化合物20),中-肌醇(化合物21),双果糖(化合物22),神经酰胺(化合物23),正丁基果糖苷(化合物24),β-谷甾醇(化合物25),β-胡萝卜苷(化合物26),棕榈酸(化合物27),硬脂酸(化合物28),十六或十八烷烃(化合物29),三十二或三十四烯烃(化合物30)。其中10个为三萜化合物(化合物1~10)都在具有一定保肝降酶活性的乙酸乙酯部位分离得到,包括2个新化合物:化合物1和化合物2。我们认为这些三萜类化合物可能就是乙酸乙酯部位保肝降酶活性的物质基础。
第三章
本文对冷水七中含有的主要活性成分刺囊酸皂苷类化合物的化学结构和活性进行了文献综述,参考了1934年至今(2006年)的157篇文献。为该类化合物的进一步开发利用提供依据。我们对猕猴桃属植物的化学成分研究也进行了综述,参考了60篇文献。
My work was composed by three parts. The first part was about the material foundation study of anti-rheumatoid arthritis (RA) effect of the rhizomes of Impatiens pritzellii Hook. f. var. hupehensis Hook. f. The second part was about the material foundation study of hepatoprotective activity of Radix Actinidia chinensis Planch root. The third part was review articles. One was the survey of chemistry and activities of echinocystic acid and its saponins, and the other was the progress of the chemical study of Genus Actinidia plants.
Part One
The rhizomes of Impatiens pritzellii Hook. f. var. hupehensis Hook. f. (Balsaminaceae) was a popular folk medicine in Tujia-tribe district of Hubei Province as an anti-RA medicine and has being used in several hospitals in Enshi district. In order to confirm the anti-RA effect and screen the active fractions and active compounds of I. pritzellii, we systematically studied the chemical constituents and the medicinal effect of this plant from Enshi district of Hubei Province.
Our study established one of the most widely used patho-model for rheumatoid arthritis: type II collagen-induced arthritis in mice (CIA). Administration of the MeOH extract and the n-BuOH fraction of I. pritzellii suppressed the development of CIA in mice significantly, and down-regulated the levels of anti-type II collagen antibodies. This result proved the anti-RA effect of I. pritzellii, and showed that the n-BuOH fraction is the active fraction of anti-RA effect of I. pritzellii, according with the results of active fraction of anti-inflammatory and analgesic effects we studied before. I. pritzellii and its active fraction also decreased the spleen and thymus indexes, down-regulated the levels of IgG, INF-γ, IL-18, and up-regulated the concentration of IL-10 in the serum of mice with CIA. Influencing many cytokines and then modulating the whole cytokine network is suggested to be one of the anti-RA mechanisms of I. pritzellii.
Our chemical constituents study of I. pritzellii afforded 30 compounds: echinocystic acid (Comp. 1), 3-O-β-D-GluA echinocystic acid (Comp. 2), 3-O-β-D-GluA-Me echinocystic acid (Comp. 3), Impatiprin A* (Comp. 4), Impatiprin B* (Comp. 5), Impatiprin C* (Comp. 6), n-butyl-β-D-fructopyranoside (Comp. 7), 5-hydroxymethyl furfural (Comp. 8), di (2-ethylhexyl) phthalate (Comp. 9), soya-cerebrosides I (Comp. 10), soya-cerebrosides II (Comp. 11), patriscabratine (Comp. 12), hentriacontane (Comp. 13), methyl lignocerate (Comp. 14), palmitic acid (Comp. 15), stearic acid (Comp. 16), methyl stearate (Comp. 17),α-spinasterol (Comp. 18), spinasteryl-3-one (Comp. 19), 3β-acetyl-α-spinasterol (Comp. 20), 3-O-β-D-Glu-α-spinasterol (Comp. 21), 3-O-palmitoyl-α-spinasterol (Comp. 22), 3-O-[6'-O-palmitoyl-Glu]-α-spinasterol (Comp. 23), n-hexadecane acid monoglyceride (Comp. 24), tetracosanoic acid monoglyceride (Comp. 25), 2-amino-2-deoxy-α-D-glucose (Comp. 26), 2-amino-2-deoxy-β-D-glucose (Comp. 27),β-D-fructofuranose (Comp. 28),α-D-fructopyranose (1-2’)β-D-fructopyranose (Comp. 29) andα-D-fructopyranose 1,2:2,3’β-D-fructopyranose (Comp. 30). Comp. 1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 12, 18, 21, 24, 25 were isolated from the active fraction: n-BuOH fraction and Comp. 4~6 are new.
In the purpose of screening the active components of anti-RA, several correlative activities of the constituents from I. pritzellii (especially the n-BuOH fraction) were evaluated, including anti-inflammatory, analgesic, immune suppressive effects, and the IL-18 inhibitory activity. Finally, CIA mice were established and used for evaluating the anti-RA activity of several active components. The results of the screening experiments showed the obvious anti-inflammatory effects of Comp. 3, 5, 6 to dimethylbenzene-induced ear edema in mice. Both of the high and low doses groups of Comp. 5 and the high dose group of Comp. 6 exhibited the analgesic effects to acetic acid-induced writhings in mice. Comp. 1, 3, 5, 7, 12, 23 could inhibited the T lymphocyte proliferation, and Comp. 1, 3, 4, 5, 7, 20, 23 exhibited depressive effect to the B lymphocyte proliferation. Administration of Comp. 2 and 6 decreased the serum hemolysin level significantly and showed obviously depressive effect to humoral immunity. Comp. 1, 2, 6, 12, 26 showed obvious activities to inhibit the production of IL-18 in PBMCs induced by LPS. At last, Comp. 5 and 6 were evaluated by CIA mice, but both of them could not suppress the development of CIA in mice significantly. From these results, it is suggested that the anti-RA effect of I. pritzellii follows the multitarget theory and the mechanism is multiplicity.
Part Two
The root of Actinidia chinensis Planch. was a traditional Chinese medicaine and used to cure hepatitis and other illness in folk. We began the material foundation study of hepatoprotective activity of Radix Actinidia chinensis.
We evaluated the effects of the alcohol extract of Radix A. chinensis root and its fractions on carbon tetrachloride (CCl4) induced acute liver damage in mice. Polysaccharides fraction and EtOAc fraction were revealed moderate or limited hepatoprotective activity. The assaying of the polysaccharides was carried out on behalf of the further study of actinidia chinensis polysaccharide (ACPS).
Our chemical constituents study of the root of Radix A. chinensis afforded 31 compounds, and 30 of them were identified: 2α,3β-dihydroxyurs-12-en-28,30-olide* (Comp. 1), 2α,3β,24-trihydroxyurs-12-en-28,30-olide* (Comp. 2), oleanolic acid (Comp. 3), 3-epi-corosolic acid (Comp. 4), 2α,3α,24-trihydroxyurs-12-en-28-oic acid (Comp. 5), 23-hydroxyursolic acid (Comp. 6), asiatic acid (Comp. 7), 2α,3α,19,24- tetrahydroxyurs-12-en-28-oic acid (Comp. 8), 3β-hydroxyurs-12,18-dien-28-oic acid (Comp. 9), 2α,23 dihydroxylmicromeric acid (Comp. 10), vanillic acid (Comp. 11), di (2-ethylhexyl) phthalate (Comp. 12), tachioside (Comp. 13), isotachioside (Comp. 14), 5-hydroxy-6-methoxy-7-O-β-D-glucosyl coumarin (Comp. 15), 1-O-(β-D-glucosyl)- 2-[2-methoxy-4-(ω-hydroxypropyl)-phenoxy]-propan-3-ol (Comp. 16), (?)-epi- catechin (Comp. 17), (+)-catechin (Comp. 18), uracil (Comp. 19), adenine (Comp. 20), myo-inositol (Comp. 21), disaccharide (Comp. 22), ceramide (Comp. 23), n-butyl-β-D-fructopyranoside (Comp. 24),β-sitosterol (Comp. 25),β-daucosterol (Comp. 26), palmitic acid (Comp. 27), stearic acid (Comp. 28), hexadecane or octadecane (Comp. 29), alkenes (Comp. 30). Ten triterpenoids (Comp. 1~10) of them were isolated from the hepatoprotective EtOAc fraction, including two new compounds: Comp. 1 and Comp. 2. These triterpenoids were thought to be the material foundation of hepatoprotective activity of EtOAc fraction of Radix Actinidia chinensis.
Part Three
Echinocystic acid (EA) and its saponins are main active constituents in I. pritzellii. One of our review in this thesis covers the chemistry and the activities of EA and its saponins from the first discovery of EA (1934) to now (2006) (157 literatures), and could be helpful to further develop and utilize of EA and its saponins. The other review article was the progress of the chemical study of Genus Actinidia plants (60 literatures).
第一章
冷水七(Impatiens pritzellii Hook. f. var. hupehensis Hook. f.)为凤仙花科凤仙花属植物,其根茎为湖北省土家族常用药材,用于治疗类风湿性关节炎(RA)。为了证实冷水七的抗RA作用以进一步扩大使用,为了筛选冷水七抗RA部位和活性成分以进一步开发新药,本研究对产于湖北恩施自治州的冷水七进行了系统的药理和化学成分研究。
本研究建立了RA的一种常见的整体动物病理模型:小牛II型胶原诱导的小鼠关节炎模型(CIA)。冷水七甲醇总膏和正丁醇部位对CIA小鼠的关节炎发展有明显的抑制作用,并都可有效降低小鼠血清中抗C II抗体水平,据此证实了冷水七具有明显抗RA作用,并确定活性部位为正丁醇部位,与我们前期研究的抗炎镇痛的活性部位一致。冷水七及其活性部位可以抑制CIA小鼠免疫器官重量,可以明显下调CIA小鼠体内促炎因子TNF-α、IFN-γ和IL-18水平,对抗炎因子IL-10有上调作用。因此推测冷水七抗RA可能的作用机理之一是其广泛地影响各种细胞因子水平,从而调节整个细胞因子网络的平衡。
本研究对冷水七进行了系统的化学成分研究,在冷水七各部位分离得到30个单体化合物,并鉴定为:刺囊酸(Comp. 1),刺囊酸-3-O-β-D-吡喃葡萄糖醛酸(Comp. 2),刺囊酸-3-O-β-D-吡喃葡萄糖醛酸甲酯苷(Comp. 3),刺囊酸-3-O-β-D-吡喃葡萄糖醛酸乙酯苷(Comp. 4)*,刺囊酸-3-O-β-D-吡喃葡萄糖醛酸丁酯苷(Comp. 5)*,刺囊酸葡萄糖醛酸丁酯-28-O-木糖-鼠李糖-木糖酯苷(Comp. 6)*,正丁基-β-D-吡喃果糖苷(Comp. 7), 5-羟甲基糠醛(Comp. 8),邻苯二甲酸二(2-乙基己基)酯(Comp. 9),大豆鞘苷I (Comp. 10),大豆鞘苷II (Comp. 11),败酱草碱(Comp. 12),三十一烷烃(Comp. 13),二十四烷酸甲酯(Comp. 14),棕榈酸(Comp. 15),硬脂酸(Comp. 16),硬脂酸甲酯(Comp. 17),α-菠甾醇(Comp. 18),菠甾酮(Comp. 19),乙酰菠甾醇(Comp. 20),菠甾醇-3-O-β-D-吡喃葡萄糖苷(Comp. 21),菠甾醇3β-棕榈酸酯(Comp. 22),菠甾醇-3-O-β-D-吡喃葡萄糖苷-6'-O-棕榈酸酯(Comp. 23),棕榈酸单甘油酯(Comp. 24),二十四烷酸单甘油酯(Comp. 25),α氨基葡萄糖(Comp. 26),β氨基葡萄糖(Comp. 27),β呋喃果糖(Comp. 28),α-吡喃果糖(1-2’)β-吡喃果糖(Comp. 29)和α-吡喃果糖1,2:2,3’β-吡喃果糖(Comp. 30)。其中Comp. 4~6为新化合物。在活性部位正丁醇部位分离得到的化合物有Comp. 1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 12, 18, 21, 24, 25共15个化合物。本研究以筛选抗RA活性成分为目的考察了从冷水七特别是其活性部位中分离得到的若干单体化合物的相关活性,涉及抗炎镇痛、免疫抑制等方面,特别是研究了受试化合物抑制IL-18的活性,最后用CIA小鼠关节炎模型检验筛选出的活性化合物。实验结果显示Comp. 3, 5, 6对二甲苯诱导的小鼠耳肿胀有明显抗炎作用,Comp. 5的高低剂量和Comp. 6的高剂量对醋酸诱发小鼠扭体有明显抑制作用,Comp. 1, 3, 5, 7, 12, 23对T淋巴细胞增殖有抑制作用,Comp. 1, 3, 4, 5, 7, 20, 23对B淋巴细胞增殖有抑制作用,Comp. 2和6对小鼠血清溶血值HC50有抑制作用,Comp. 1, 2, 6, 12, 26对LPS诱导人PBMCs产生的IL-18有明显的抑制活性。在最后小鼠CIA关节炎模型筛选中,考察了Comp. 5和6对CIA小鼠关节炎指数的影响,未发现明显抑制作用。通过本研究得出结论,冷水七的抗RA作用具有多靶点性,其作用机理也具有多重性。
第二章
中华猕猴桃(Actinidia chinensis Planch.)为猕猴桃科猕猴桃属植物,其根民间用于治疗肝炎及其他病症。我们对中华猕猴桃根进行了保肝药效物质基础的初步研究。
建立了CCl4引起的小鼠急性肝损伤模型,对中华猕猴桃根乙醇总膏及其不同极性部位进行了保肝降酶活性的筛选。实验结果表明多糖部位和乙酸乙酯部位具有一定的保肝降酶活性。为了有利于中华猕猴桃根多糖(ACPS)的进一步研究,我们对中华猕猴桃根乙醇总膏和水部位进行了多糖的含量测定。
本研究对中华猕猴桃根进行了系统的化学成分研究,在各部位分离得到31个单体化合物,并鉴定30个化合物:2α,3β-dihydroxyurs-12-en-28,30-olide* (化合物1), 2α,3β,24-trihydroxyurs-12-en-28,30-olide* (化合物2),齐墩果酸(化合物3),表科罗索酸(化合物4), 2α,3α,24-trihydroxyurs-12-en-28-oic acid (化合物5), 23-hydroxyursolic acid (化合物6),积雪草酸(化合物7), 2α,3α,19,24- tetrahydroxyurs-12-en-28-oic acid (化合物8), 3β-hydroxyurs-12,18-dien-28-oic acid (化合物9), 2α,23 dihydroxylmicromeric acid (化合物10),香草酸(化合物11),邻苯二甲酸二(2-乙基己基)酯(化合物12), tachioside (化合物13), isotachioside (化合物14), 5-hydroxy-6-methoxy-7-O-β-D-glucosyl coumarin (化合物15), 1-O-(β-D-glucosyl)-2-[2-methoxy-4-(ω-hydroxypropyl)-phenoxy]-propan-3-ol (化合物16),表-儿茶素(化合物17), (+)-儿茶素(化合物18),鸟嘧啶(化合物19),腺嘌呤(化合物20),中-肌醇(化合物21),双果糖(化合物22),神经酰胺(化合物23),正丁基果糖苷(化合物24),β-谷甾醇(化合物25),β-胡萝卜苷(化合物26),棕榈酸(化合物27),硬脂酸(化合物28),十六或十八烷烃(化合物29),三十二或三十四烯烃(化合物30)。其中10个为三萜化合物(化合物1~10)都在具有一定保肝降酶活性的乙酸乙酯部位分离得到,包括2个新化合物:化合物1和化合物2。我们认为这些三萜类化合物可能就是乙酸乙酯部位保肝降酶活性的物质基础。
第三章
本文对冷水七中含有的主要活性成分刺囊酸皂苷类化合物的化学结构和活性进行了文献综述,参考了1934年至今(2006年)的157篇文献。为该类化合物的进一步开发利用提供依据。我们对猕猴桃属植物的化学成分研究也进行了综述,参考了60篇文献。
My work was composed by three parts. The first part was about the material foundation study of anti-rheumatoid arthritis (RA) effect of the rhizomes of Impatiens pritzellii Hook. f. var. hupehensis Hook. f. The second part was about the material foundation study of hepatoprotective activity of Radix Actinidia chinensis Planch root. The third part was review articles. One was the survey of chemistry and activities of echinocystic acid and its saponins, and the other was the progress of the chemical study of Genus Actinidia plants.
Part One
The rhizomes of Impatiens pritzellii Hook. f. var. hupehensis Hook. f. (Balsaminaceae) was a popular folk medicine in Tujia-tribe district of Hubei Province as an anti-RA medicine and has being used in several hospitals in Enshi district. In order to confirm the anti-RA effect and screen the active fractions and active compounds of I. pritzellii, we systematically studied the chemical constituents and the medicinal effect of this plant from Enshi district of Hubei Province.
Our study established one of the most widely used patho-model for rheumatoid arthritis: type II collagen-induced arthritis in mice (CIA). Administration of the MeOH extract and the n-BuOH fraction of I. pritzellii suppressed the development of CIA in mice significantly, and down-regulated the levels of anti-type II collagen antibodies. This result proved the anti-RA effect of I. pritzellii, and showed that the n-BuOH fraction is the active fraction of anti-RA effect of I. pritzellii, according with the results of active fraction of anti-inflammatory and analgesic effects we studied before. I. pritzellii and its active fraction also decreased the spleen and thymus indexes, down-regulated the levels of IgG, INF-γ, IL-18, and up-regulated the concentration of IL-10 in the serum of mice with CIA. Influencing many cytokines and then modulating the whole cytokine network is suggested to be one of the anti-RA mechanisms of I. pritzellii.
Our chemical constituents study of I. pritzellii afforded 30 compounds: echinocystic acid (Comp. 1), 3-O-β-D-GluA echinocystic acid (Comp. 2), 3-O-β-D-GluA-Me echinocystic acid (Comp. 3), Impatiprin A* (Comp. 4), Impatiprin B* (Comp. 5), Impatiprin C* (Comp. 6), n-butyl-β-D-fructopyranoside (Comp. 7), 5-hydroxymethyl furfural (Comp. 8), di (2-ethylhexyl) phthalate (Comp. 9), soya-cerebrosides I (Comp. 10), soya-cerebrosides II (Comp. 11), patriscabratine (Comp. 12), hentriacontane (Comp. 13), methyl lignocerate (Comp. 14), palmitic acid (Comp. 15), stearic acid (Comp. 16), methyl stearate (Comp. 17),α-spinasterol (Comp. 18), spinasteryl-3-one (Comp. 19), 3β-acetyl-α-spinasterol (Comp. 20), 3-O-β-D-Glu-α-spinasterol (Comp. 21), 3-O-palmitoyl-α-spinasterol (Comp. 22), 3-O-[6'-O-palmitoyl-Glu]-α-spinasterol (Comp. 23), n-hexadecane acid monoglyceride (Comp. 24), tetracosanoic acid monoglyceride (Comp. 25), 2-amino-2-deoxy-α-D-glucose (Comp. 26), 2-amino-2-deoxy-β-D-glucose (Comp. 27),β-D-fructofuranose (Comp. 28),α-D-fructopyranose (1-2’)β-D-fructopyranose (Comp. 29) andα-D-fructopyranose 1,2:2,3’β-D-fructopyranose (Comp. 30). Comp. 1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 12, 18, 21, 24, 25 were isolated from the active fraction: n-BuOH fraction and Comp. 4~6 are new.
In the purpose of screening the active components of anti-RA, several correlative activities of the constituents from I. pritzellii (especially the n-BuOH fraction) were evaluated, including anti-inflammatory, analgesic, immune suppressive effects, and the IL-18 inhibitory activity. Finally, CIA mice were established and used for evaluating the anti-RA activity of several active components. The results of the screening experiments showed the obvious anti-inflammatory effects of Comp. 3, 5, 6 to dimethylbenzene-induced ear edema in mice. Both of the high and low doses groups of Comp. 5 and the high dose group of Comp. 6 exhibited the analgesic effects to acetic acid-induced writhings in mice. Comp. 1, 3, 5, 7, 12, 23 could inhibited the T lymphocyte proliferation, and Comp. 1, 3, 4, 5, 7, 20, 23 exhibited depressive effect to the B lymphocyte proliferation. Administration of Comp. 2 and 6 decreased the serum hemolysin level significantly and showed obviously depressive effect to humoral immunity. Comp. 1, 2, 6, 12, 26 showed obvious activities to inhibit the production of IL-18 in PBMCs induced by LPS. At last, Comp. 5 and 6 were evaluated by CIA mice, but both of them could not suppress the development of CIA in mice significantly. From these results, it is suggested that the anti-RA effect of I. pritzellii follows the multitarget theory and the mechanism is multiplicity.
Part Two
The root of Actinidia chinensis Planch. was a traditional Chinese medicaine and used to cure hepatitis and other illness in folk. We began the material foundation study of hepatoprotective activity of Radix Actinidia chinensis.
We evaluated the effects of the alcohol extract of Radix A. chinensis root and its fractions on carbon tetrachloride (CCl4) induced acute liver damage in mice. Polysaccharides fraction and EtOAc fraction were revealed moderate or limited hepatoprotective activity. The assaying of the polysaccharides was carried out on behalf of the further study of actinidia chinensis polysaccharide (ACPS).
Our chemical constituents study of the root of Radix A. chinensis afforded 31 compounds, and 30 of them were identified: 2α,3β-dihydroxyurs-12-en-28,30-olide* (Comp. 1), 2α,3β,24-trihydroxyurs-12-en-28,30-olide* (Comp. 2), oleanolic acid (Comp. 3), 3-epi-corosolic acid (Comp. 4), 2α,3α,24-trihydroxyurs-12-en-28-oic acid (Comp. 5), 23-hydroxyursolic acid (Comp. 6), asiatic acid (Comp. 7), 2α,3α,19,24- tetrahydroxyurs-12-en-28-oic acid (Comp. 8), 3β-hydroxyurs-12,18-dien-28-oic acid (Comp. 9), 2α,23 dihydroxylmicromeric acid (Comp. 10), vanillic acid (Comp. 11), di (2-ethylhexyl) phthalate (Comp. 12), tachioside (Comp. 13), isotachioside (Comp. 14), 5-hydroxy-6-methoxy-7-O-β-D-glucosyl coumarin (Comp. 15), 1-O-(β-D-glucosyl)- 2-[2-methoxy-4-(ω-hydroxypropyl)-phenoxy]-propan-3-ol (Comp. 16), (?)-epi- catechin (Comp. 17), (+)-catechin (Comp. 18), uracil (Comp. 19), adenine (Comp. 20), myo-inositol (Comp. 21), disaccharide (Comp. 22), ceramide (Comp. 23), n-butyl-β-D-fructopyranoside (Comp. 24),β-sitosterol (Comp. 25),β-daucosterol (Comp. 26), palmitic acid (Comp. 27), stearic acid (Comp. 28), hexadecane or octadecane (Comp. 29), alkenes (Comp. 30). Ten triterpenoids (Comp. 1~10) of them were isolated from the hepatoprotective EtOAc fraction, including two new compounds: Comp. 1 and Comp. 2. These triterpenoids were thought to be the material foundation of hepatoprotective activity of EtOAc fraction of Radix Actinidia chinensis.
Part Three
Echinocystic acid (EA) and its saponins are main active constituents in I. pritzellii. One of our review in this thesis covers the chemistry and the activities of EA and its saponins from the first discovery of EA (1934) to now (2006) (157 literatures), and could be helpful to further develop and utilize of EA and its saponins. The other review article was the progress of the chemical study of Genus Actinidia plants (60 literatures).
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