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1、Natural Products Chemistry唐万侠(Tang Wanxia)2012-2013(2)Bilingual Teaching Methods Explain the knowledge in English and Chinese. Pay attention to the culture exchange in the world. Improve the ability to utilize specialty English. Examination for Natural Products ChemistrySelective Course1. Come to th
2、e class on time: 102. Behaviour in class: 103. Class note: 10 4. Examination at the end of the class: 70Note: Someone cant be allowed to come to the examination if he is absent from the class more than 6 times.Class ContentsChapter 1 IntroductionChapter 2 Saccharide and GlycosidesChapter 3 Phenylpro
3、panoidsChapter 4 QuinonesChapter 5 FlavonoidsChapter 6 Terpenoids and Volatile oilsChapter 7 Triterpenoids and SaponinsChapter 8 Steroides and GlycosidesChapter 9 AlkaloidsChapter 10 Marine Natural Products糖和苷苯丙素类化合物醌类化合物黄酮类化合物萜类和挥发油三萜及其苷类甾体及其苷类生物碱海洋天然药物 1、Outline3、Extract and isolation methods4、Str
4、uctural elucidation methods2、BiosynthesisChapter 1 Introduction1、OutlineDefinition: Natural products chemistry is a subject to research the chemical constituents of natural medicinal plants on the base of modern scientific theory and methods. Contents:Structural characteristics, physicochemical prop
5、erties, extract and isolation methods, and structural elucidation of the chemical constituents of all kinds of natural medicinal plants. Research resource: Natural plants (major), animals, minerals, and microorganism.1、OutlineNatural medicinal plants herb medicine麻黄 (Ephedra spp.)1、Outline1、Outline槐
6、花米 Sophora japonica1、Outline 1、OutlineDevelopments in foreign countries In 1769, tartar (potassium hydrogen tartrate) was transferred to calcium salt and decomposed in sulphuric acid to produce tartaric acid. (K. W. Schelle, Swedish) In 1804, morphine was isolated from opium (Dorosine, French) In 18
7、06, morphine was isolated from opium (Serturner, German) In 1810-1860, the period of alkaloid development1、OutlineSpectroscopic analysis: NMR, MS, IR, and UV.Research methods: extract and isolation guided by bioactive scanning, structural modification, and total synthesis. 1、OutlineDevelopment of no
8、wadays 1、Outline3、Extract and isolation methods4、Structural elucidation methods2、BiosynthesisChapter 1 Introduction2、BiosynthesisCO2H2O葡萄糖代谢磷酸烯醇式丙酮酸丙酮酸乙酰辅酶A丙二酸甲酰辅酶A甲羟戊酸萜类甾类胡萝卜素类4-磷酸脂肪酸类前列腺素类脂肪族及芳香族聚酮类醌类-氨基乙酰丙酸胆碱、卟啉类鞣酸类莽草酸苯丙素类芳香族氨基酸脂肪族氨基酸嘌呤、嘧啶核苷酸类肽类含氮化合物生物碱类黄酮类hResults of biosynthesis Any kind of pla
9、nt will produce some specific constituents to express their physiological and biochemical characteristics. The constituents of some same family plants were different with the long history development, but the skeleton of which are consistent, only the side chain was isomerized. The constituents indi
10、cated the developing direction of some family plants in the biosynthetic recycle system. Similar relative plants possess similar constituents.2、BiosynthesisThe similar structure components maybe originate from the same precursor in biosynthesis, which provide a direction to study plant chemical cate
11、gory and find new natural medicinal plant resource. For example: C5 is the basic skeleton in terpenoids, which exhibit the same biosynthetic route in terpenoids-isoprene rule. 2、BiosynthesisH2CCHCH2H3CBasic structure unit C2 unit (acetic acid): fatty acid, phenol, benzoquinone. C5 unit (isoprene): t
12、erpenoids and steroids. C6-C3 unit: coumarin and lignan, which belong to phenylpropanoids. Amino acid unit: Alkaloids. Composite unit: Constructed by the above units. 2、BiosynthesisBiosynthetic pathways In natural products chemistry field, many researchers noticed the relationship between the struct
13、ures of natural compounds. Accordingly, they hand in the hypothesis of biosynthesis, some of which were certified by isotopic label experiments. We called these as biosynthetic pathways: Acetate-malonate pathway (AA-MA, 醋酸-丙二酸途径) Mevalonic acid pathway (MVA, 甲戊二羟酸途径) Cinnamic acid and shikimic acid
14、pathways (桂皮酸及莽草酸途径) Amino acid pathway (氨基酸途径) Composite pathway (复合途径)2、BiosynthesisAcetate-malonate pathway (AA-MA, 醋酸-丙二酸途径)乙酰辅酶A丙二酸单酰辅酶A复原NADPHNADP缩合+CH2COOHCOACPNADPHNADPCH3(CH2)nCOOH脂肪酸酚类和蒽醌类缩合 1、Outline3、Extract and isolation methods4、Structural elucidation methods2、BiosynthesisChapter 1 Int
15、roductionSummary1、The definition and research contents of this subject. 2、Modern techniques used in natural products research.3、Four different biosynthesis pathways.Problems1、What are the definition and research contents of Natural Products Chemistry?1. 杨世林, 天然药物化学M, 2021, 科学出版社. 2. Paul M Dewick, Medicinal Natural Products M, 1998, Wiley. 3. Journal of Natural Products J. 4. Bioorganic & Medicinal Chemistry Letters J. 5. Tetrahedron Letters J.6. Tetra
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