本文關(guān)鍵詞：兩種藥用植物成分及結(jié)構(gòu)多樣性吲哚生物堿的制備研究　出處：《云南大學(xué)》2016年博士論文　論文類型：學(xué)位論文

  更多相關(guān)文章： 卵葉巴豆 糖膠樹(shù) 燈臺(tái)葉 吲哚生物堿 細(xì)胞毒活性 抗菌活性 抗HIV活性 促進(jìn)胞內(nèi)鈣流活性

【摘要】：本論文由五章組成。第一章對(duì)大戟科(Euphorbiaceae)巴豆屬卵葉巴豆(Croton caudatus)的枝葉進(jìn)行了化學(xué)成分研究,并對(duì)其得到的部分單體化合物進(jìn)行了抗腫瘤、抗菌及抗HIV活性研究,從而發(fā)現(xiàn)了4個(gè)活性化合物。第二章對(duì)夾竹桃科(Apocynaceae)雞骨常山屬糖膠樹(shù)(A. scholaris)的蟲(chóng)癭葉子進(jìn)行了生物堿成分研究,并對(duì)其得到的新骨架化合物進(jìn)行了促進(jìn)神經(jīng)干細(xì)胞增殖的生物活性研究。第三章對(duì)糖膠樹(shù)的根進(jìn)行了化學(xué)成分研究,從中分離鑒定了14個(gè)已知化合物。第四章對(duì)糖膠樹(shù)的枝條進(jìn)行了化學(xué)成分研究,從中分離鑒定了11個(gè)已知化合物。第五章對(duì)多樣性吲哚生物堿的制備進(jìn)行了研究,并對(duì)其得到的單體化合物進(jìn)行了促進(jìn)胞內(nèi)鈣流活性和促進(jìn)PC12細(xì)胞分化的活性研究,發(fā)現(xiàn)了4個(gè)活性化合物。運(yùn)用多種色譜技術(shù)(例如：正相硅膠柱色譜、反相硅膠柱色譜、薄層色譜、sephadax LH-20凝膠柱色譜、中壓制備色譜、液相超高壓制備色譜)和波譜學(xué)方法(1D NMR、2D NMR、MS、UV、IR、CD、X-ray單晶衍射和量子化學(xué)計(jì)算)從上述3種研究對(duì)象中共分離鑒定化合物82個(gè),其中24個(gè)為新化合物�；衔镱愋蜕婕岸啤⑺妮�、大柱香波龍烷苷、黃酮、木脂素、吲哚生物堿等。1、大戟科植物卵葉巴豆的化學(xué)成分和生物活性研究卵葉巴豆(Croton caudatus),大戟科巴豆屬植物,攀援灌木,其葉卵圓形,故名卵葉巴豆。該植物產(chǎn)于云南西南部,生于海拔500-600米疏林中。分布于印度、斯里蘭卡、中南半島及馬來(lái)西亞。該屬植物以二萜成分為主,而這些二萜成分不僅提供了大戟科植物的化學(xué)分類依據(jù),而且也是主要的活性物質(zhì)。我們對(duì)采自云南西雙版納的卵葉巴豆枝葉進(jìn)行了化學(xué)成分研究。從中分離得到了11個(gè)化合物,其中有4個(gè)二萜、1個(gè)大柱香波龍烷苷、3個(gè)黃酮、2個(gè)木脂素和1個(gè)四萜。新化合物4個(gè),包括3個(gè)新的tigliane骨架類型二萜和1個(gè)新的大柱香波龍烷苷。對(duì)3個(gè)新的tigliane骨架類型二萜進(jìn)行了人體腫瘤細(xì)胞毒活性實(shí)驗(yàn),發(fā)現(xiàn)了化合物1-3均有一定的體外腫瘤抑制活性。對(duì)化合物4進(jìn)行了抗菌和抗HIV活性測(cè)試,發(fā)現(xiàn)其具有一定的抗菌及抗HIV活性。2、夾竹桃科植物糖膠樹(shù)蟲(chóng)癭葉子的化學(xué)成分和生物活性研究糖膠樹(shù)(Alstonia scholaris),夾竹桃科雞骨常山屬植物,木材的材質(zhì)松軟細(xì)致,全株乳汁豐富,可提取口香糖原料,故名“糖膠樹(shù)”。糖膠樹(shù)葉子俗稱“燈臺(tái)葉”,傣藥中用于治療百日咳、慢性支氣管炎等�，F(xiàn)在市場(chǎng)上也有云南大唐漢方制藥有限公司生產(chǎn)的燈臺(tái)葉片及昆明振華制藥廠有限公司生產(chǎn)的燈臺(tái)葉顆粒等非處方藥用產(chǎn)品。由本課題組研發(fā)的五類新藥燈臺(tái)葉總生物堿膠囊具有止咳、平喘、抗炎及鎮(zhèn)痛療效,目前已完成一期臨床的相關(guān)實(shí)驗(yàn)。作為藥材研究的一部分,我們對(duì)蟲(chóng)癭的燈臺(tái)葉進(jìn)行了化學(xué)成分研究,從中共分離鑒定21個(gè)單體化合物,包括1個(gè)新骨架降C-5吲哚生物堿、19個(gè)單萜吲哚生物堿和1個(gè)木脂素。3、夾竹桃科植物糖膠樹(shù)根的化學(xué)成分研究我們經(jīng)過(guò)對(duì)糖膠樹(shù)根提取物的研究發(fā)現(xiàn),其液相指紋圖譜與葉子的指紋圖譜不盡相同,而且糖膠樹(shù)中已發(fā)現(xiàn)的化合物結(jié)構(gòu)骨架種類較多、活性突出,帶著發(fā)現(xiàn)新結(jié)構(gòu)與活性物質(zhì)的興趣與目標(biāo),我們對(duì)糖膠樹(shù)根進(jìn)行了化學(xué)成分研究,共分離鑒定14個(gè)單體化合物。4、夾竹桃科植物糖膠樹(shù)枝條的化學(xué)成分研究糖膠樹(shù)樹(shù)皮記載有治頭痛、傷風(fēng)、痧氣、肺炎、百日咳、慢性支氣管炎等療效；外用可治外傷止血、接骨、消腫、瘡節(jié)及配制殺蟲(chóng)劑等。前期,我們對(duì)糖膠樹(shù)蟲(chóng)癭葉子、糖膠樹(shù)根進(jìn)行了化學(xué)成分研究,發(fā)現(xiàn)了較多骨架類型的生物堿。本章我們研究了糖膠樹(shù)枝條的化學(xué)成分,期望能夠豐富糖膠樹(shù)中發(fā)現(xiàn)的生物堿的化合物庫(kù)。經(jīng)過(guò)系統(tǒng)的化學(xué)成分研究,共分離鑒定了11個(gè)單體化合物。5、結(jié)構(gòu)多樣性吲哚生物堿的制備及生物活性研究自然界中的單萜吲哚生物堿骨架千變?nèi)f化,數(shù)量較多,但是它們基本都從異胡豆苷衍變而來(lái)。而異胡豆苷這個(gè)重排單萜吲哚生物堿則由色胺和裂化馬錢(qián)子苷以1：1的摩爾比在異胡豆苷合成酶的作用下發(fā)生Mannich反應(yīng)得來(lái)。然而,我們課題組在對(duì)盆架樹(shù)化學(xué)成分的研究過(guò)程中發(fā)現(xiàn)了色胺和裂環(huán)馬錢(qián)子苷以1：2摩爾比縮合的產(chǎn)物alstrostines A和B,這促使我們思考吲哚生物堿的生源合成途徑的多樣性。本章以色胺和獐牙菜苦苷為反應(yīng)底物,制備結(jié)構(gòu)多樣的吲哚生物堿,并探究吲哚生物堿的合成途徑,共分離鑒定24個(gè)化合物,包括23個(gè)吲哚生物堿,其中19個(gè)為新化合物。對(duì)部分吲哚生物堿進(jìn)行了促進(jìn)PC12細(xì)胞分化和促進(jìn)胞內(nèi)鈣流活性研究,并從中發(fā)現(xiàn)了4個(gè)具有促進(jìn)胞內(nèi)鈣流活性的化合物。
[Abstract]:This thesis consists of five chapters. The first chapter of the Euphorbiaceae Croton leaf egg (Euphorbiaceae) (Croton caudatus) Croton leaves the studies on the chemical constituents, and some of its compounds obtained antitumor, antibacterial and anti HIV activity to study, found 4 compounds in the second chapter. Apocynaceae (Apocynaceae) chicken bone Changshan alstoniascholaris (A. scholaris) leaves galls were studied and the new alkaloids, the skeleton compounds obtained to promote the study of biological activity of the proliferation of neural stem cells. The third chapter of alstoniascholaris root of the studies on the chemical constituents, from the isolation of 14 the fourth chapter of known compounds. Branches of the chemical constituents of alstoniascholaris research, from the isolation of 11 known compounds. The fifth chapter on the diversity of indole alkaloid preparation were studied, and the obtained The monomer compounds were promoting intracellular calcium current activities and promoting the activity of PC12 cell differentiation, 4 compounds were found. Using various chromatographic techniques (such as silica gel column chromatography, reversed-phase silica gel column chromatography, thin layer chromatography, sephadax LH-20 gel column chromatography, preparative liquid pressing, ultra high pressure system preparation of chromatographic and spectroscopic methods (1D, NMR), 2D, NMR, MS, UV, IR, CD, X-ray diffraction and quantum chemical calculation) from the above 3 kinds of research object the isolation and identification of 82 compounds, including 24 new compounds. Compounds involving two terpenes, four terpenes, Dazhu dragon Wangan shampoo, flavonoids, lignans, indole alkaloid.1, Euphorbiaceae Croton leaf egg studies on chemical constituents and Bioactivities of eggs (Croton caudatus), Croton leaf Euphorbiaceae, climbing shrubs, leaves oval, leaves the eggs. The plant named Croton produced in the southwest of Yunnan, Born in 500-600 meters above sea level in thin forests. Distributed in India, Sri Lanka, Indochina and Malaysia. The genus with two terpenoids, and these two terpenoids not only provides the basis for classification of chemical plants of the family Euphorbiaceae, and is the main active substance. We collected from Yunnan Xishuangbanna egg leaf leaves of Croton Study on the chemical constituents. 11 compounds were isolated from the 4, two terpenes, 1 large dragon Wangan 3 column shampoo, 2 flavonoids, lignans and 1 four terpene. 4 new compounds, including 3 new tigliane framework type two terpene and 1 new high column Wangan. Human dragon shampoo cytotoxicity experiment was carried out on 3 NEW tigliane skeleton type two terpene compounds 1-3 were found in vitro antitumor activity of 4 compounds. The antibacterial and anti HIV activity test, found that it has a certain antibacterial And the anti HIV activity of.2, studies on chemical constituents and Bioactivities of alstoniascholaris Apocynaceae plant alstoniascholaris gall leaves (Alstonia scholaris), Apocynaceae plants of the genus in Changshan chicken bone, wood material soft delicate, whole plant milk rich, chewing gum can extract raw materials, named "gum tree". Commonly known as "dengtaiye alstoniascholaris leaves" Dai medicine for the treatment of whooping cough, chronic bronchitis and so on. There are now on the market and leaves Yunnan Datang Hanfang Pharmaceutical Co Ltd Kunming Zhenhua pharmaceutical factory production and limited production of dengtaiye particles and other non prescription pharmaceutical products. By five and the total alkaloid drug developed leaf capsule has a cough. Antiasthmatic effect, anti-inflammatory and analgesic, currently a clinical experiment has been completed. As a part of the traditional Chinese medicine research, we cecidium dengtaiye studied chemical composition, from the Communist Party of China Isolation and identification of 21 compounds, including 1 new skeleton drop C-5 indole alkaloid, 19 monoterpene indole alkaloids and 1 lignans.3, chemical composition of Apocynaceae plant gum root research we have studied on the root extract of fucoidan, the liquid phase fingerprint fingerprint atlas and leaves are not the same moreover, skeleton compounds more species have been found in the activity of alstoniascholaris outstanding, with a new found interest and target structure and active substances, we carried out to study the chemical constituents of polysaccharide were isolated from roots, 14 monomer compound.4, Apocynaceae plant gum tree branches on the chemical constituents of alstoniascholaris bark records have headache, colds, fever, pneumonia, whooping cough, chronic bronchitis; cure traumatic bleeding, bone, swelling, sores and preparation of pesticides. The festival, I have to gum tree leaf galls Son, roots of the studies on the chemical constituents of polysaccharide, alkaloid found more skeleton types. In this chapter we study the chemical constituents of alstoniascholaris branches, expected to find abundant alkaloids in compound library alstoniascholaris. Through the systemic study on the chemical constituents were isolated, identified 11 compounds.5, structural diversity of indole alkaloid preparation and biological activity of natural monoterpene indole alkaloid skeleton quantity, but the myriads of changes, they are basically from the strictosidine gene. With Hu Dougan the rearrangement of monoterpenoid indole alkaloid by tryptamine and cracking of loganin in a 1:1 molar ratio in strictosidine synthase function under the Mannich reaction. However, our group in the course of the study on the chemical constituents of Winchia CALOPHYLLA have been found in the tryptamine and split ring loganin at a molar ratio of 1:2 condensation products Alstrostines A and B, which prompted us to think about the diversity of the biosynthetic pathway of indole alkaloids. In this chapter, tryptamine and swertiamarin as substrate, preparation of indole alkaloids, structural diversity, and to explore the synthesis pathway of indole alkaloids, were isolated and identified 24 compounds, including 23 indole alkaloids, of which 19 a new compound. Some indole alkaloids were promotes the differentiation of PC12 cells and promote the activity of intracellular calcium influx, and found 4 compounds could promote the activity of intracellular calcium flow from it.

【學(xué)位授予單位】：云南大學(xué)
【學(xué)位級(jí)別】：博士
【學(xué)位授予年份】：2016
【分類號(hào)】：Q946

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