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Introduction to Natural Products Chemistry [Hardback]

Edited by (Shanghai Institute of Materia Medica, Pudong, China), Edited by (Shanghai Institute of Materia Medica, Pudong, China), Edited by (Shanghai Institute of Materia Medica, Pudong, China)
  • Formāts: Hardback, 380 pages, height x width: 254x178 mm, weight: 1800 g, 27 Tables, black and white; 49 Illustrations, black and white
  • Izdošanas datums: 20-Jul-2011
  • Izdevniecība: CRC Press Inc
  • ISBN-10: 1439860769
  • ISBN-13: 9781439860762
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  • Formāts: Hardback, 380 pages, height x width: 254x178 mm, weight: 1800 g, 27 Tables, black and white; 49 Illustrations, black and white
  • Izdošanas datums: 20-Jul-2011
  • Izdevniecība: CRC Press Inc
  • ISBN-10: 1439860769
  • ISBN-13: 9781439860762
Citas grāmatas par šo tēmu:
The Chinese original was published in 2006 by the Science Press of China as part of a series introducing modern chemistry to scientists and graduate students. It compiles the most important results of natural products chemistry in China. The topics are extracting and isolating natural products, the chemistry of fungal products, alkalopoids, sesquiterpenoids, diterpenes, saponins, amino acids and peptides, flavonoids, athraquinones, coumarins, other natural bioactive compounds, marine natural products, the structural modification of active principles from traditional Chinese medicine, and the chemical synthesis of natural products. Annotation ©2011 Book News, Inc., Portland, OR (booknews.com)

Natural products chemistry—the chemistry of metabolite products of plants, animals and microorganisms—is involved in the investigation of biological phenomena ranging from drug mechanisms to gametophytes and receptors and drug metabolism in the human body to protein and enzyme chemistry.

Introduction to Natural Products Chemistry has collected the most important research results of natural product chemistry in China. It overviews the basic principles of isolation, structure, and characteristics of natural products and illustrates current research techniques of structure elucidation with real-life examples of wet chemistry and spectroscopic analyses (UV, IR, MS, and NMR, especially 2d-NMR, HMBC, and HMQC), bioactivity, biosynthesis, and chemical synthesis.

Specifically, this book covers:

  • Extraction and isolation of natural products
  • Chemistry of fungal products
  • Alkaloids, sesquiterpenoids, diterpenes, and saponins
  • Amino acids and peptides
  • Flavonoids, anthraquinones, coumarins, and lignans
  • Marine natural products
  • Structural modification of active principles from traditional Chinese medicine
  • Chemical synthesis of natural products

Although natural products chemistry has produced enormous results and made great contributions to human health, industry, and agriculture, only a fraction of natural resources have been rigorously studied. Chinese natural products are a gold mine for further exploration with modern technology and methods. This book represents the continuing collaboration between the fields of natural products chemistry, medicine, biology, and agriculture which will continue to discover and implement novel chemical products from natural sources.

Preface xv
Contributors xvii
Chapter 1 Introduction
1(4)
Chapter 2 Extraction and Isolation of Natural Products
5(22)
Section 1 Extraction of Natural Products
5(1)
1.1 Traditional solvent extraction methods
5(1)
1.2 Water steam distillation
6(1)
1.3 Supercritical fluid extraction
6(1)
1.4 Solid phase extraction
6(1)
Section 2 Separation of Natural Products
6(1)
2.1 Classical separation methods
6(3)
2.1.1 Solvent partition
7(1)
2.1.2 Fractional distillation
7(1)
2.1.3 Precipitation
7(1)
2.1.4 Membrane separation
8(1)
2.1.5 Sublimation
8(1)
2.1.6 Crystallization
8(1)
2.1.7 Removal of impurities
8(1)
2.2 Chromatographic separation methods
9(18)
2.2.1 Basic principles
9(1)
2.2.2 Classification of chromatography
9(1)
2.2.3 Liquid-solid chromatographic separation
10(10)
2.2.4 Countercurrent chromatography
20(3)
Section 3 Concluding Remarks
23(1)
Bibliography
23(1)
References
24(3)
Chapter 3 Chemistry of Fungal Products
27(28)
Section 1 Introduction
27(3)
Section 2 Bioactive Fungal Metabolites
30(1)
2.1 Terpenes
31(1)
2.2 Steroids
32(1)
2.3 Polyketides
33(1)
2.4 Phenols, quinones, and other aromatic compounds
33(1)
2.5 Polyacetylenes
34(1)
2.6 Alkaloids
35(1)
2.7 Macrolides
35(1)
2.8 Peptides, diketopiperazines, depsipeptides
36(2)
2.9 Helagen containing compounds
38(1)
2.10 Miscellaneous secondary metabolites
38(4)
Section 3 Mycotoxins from Fungi
39(1)
Section 4 Isolation and Structure Studies of Fungal Products
40(2)
4.1 Polysaccharide preparations of Chinese traditional medicine Poria cocos (Fu-Ling) and Polyporus umbellatus (Zhu-Ling)
42(1)
4.1.1 Polysaccharide extract of Poria cocos
42(1)
4.1.2 Polysaccharide extract of Polyporus umbellatus
42(1)
4.2 Bioactive triterpenes from polypore Ganoderma lucidum Ling-Zhi
43(1)
4.2.1 Isolation of lucidenic acid N and methyl lucidenate F
43(1)
4.2.2 Structure elucidation of lucidenic acid N
43(1)
4.3 Undecylresorcinol dimer from Coleophoma sp
44(2)
4.3.1 Isolation of undecylresorcinol dimer
44(1)
4.3.2 Structure elucidation of undecylresorcinol dimer
45(1)
4.4 Balanol from the fungi Verticillioum balanoides and Acremonium sp
46(2)
4.4.1 Isolation of balanol from Verticillium balanoides and Acremonium sp
46(1)
4.4.2 Structure elucidation of balanol
46(2)
4.5 Pericosine A from Periconia byssoides OUPS-N133
48(7)
4.5.1 Isolation of pericosine A
48(1)
4.5.2 Structure elucidation of pericosine A
48(1)
Section 5 Perspectives
49(1)
References
50(5)
Chapter 4 Alkaloids
55(26)
Section 1 General
55(1)
Section 2 Characterization, Identification and Isolation
56(2)
Section 3 Classification
58(1)
3.1 Isoquinolines
58(3)
3.1.1 Simple isoquinoline alkaloids
58(1)
3.1.2 Benzylisoquinoline alkaloids
59(1)
3.1.3 Bisbenzylisoquinoline alkaloids
59(1)
3.1.4 Aporphine alkaloids
59(1)
3.1.5 Protoberberine alkaloids
59(1)
3.1.6 Protopine alkaloids
60(1)
3.1.7 Emetine alkaloids
60(1)
3.1.8 α-Naphthaphenanthridine alkaloids
61(1)
3.1.9 Morphine alkaloids
61(1)
3.2 Quinolines
61(1)
3.3 Pyrrolidines
62(2)
3.3.1 Simple pyrrolidine alkaloids
62(1)
3.3.2 Pyrrolizidine alkaloids
63(1)
3.3.3 Indolizidine alkaloids
63(1)
3.3.4 Tropane alkaloids
64(1)
3.3.5 Stemona alkaloids
64(1)
3.4 Indoles
64(1)
Section 4 Structural Investigations of Some Alkaloids
65(1)
4.1 Stemona alkaloids
65(6)
4.1.1 Stemotinine
66(1)
4.1.2 Isostemotinine
67(1)
4.1.3 Parvistemonine
68(3)
4.2 Camptothecin and its analogues
71(3)
4.3 Sinomenine and sinoacutine
74(1)
4.4 Pyridone alkaloids---huperzine
75(6)
4.4.1 Huperzines A and B
75(1)
4.4.2 Total synthesis of huperzine A
76(1)
4.4.3 Physiological activity of huperzine
76(1)
Bibliography
77(1)
References
78(3)
Chapter 5 Sesquiterpenoids
81(20)
Section 1 Chemical Properties, Isolation and Purification
81(5)
Section 2 Spectroscopic Analysis of Sesquiterpenes
86(1)
2.1 UV, IR and MS spectra
86(1)
2.2 1H-NMR spectra of sesquiterpenes
87(1)
2.2.1 Detection of acyl side chain
87(1)
2.2.2 Detection of skeleton type
87(1)
2.2.3 Analyzing patterns of oxygen atoms
87(1)
2.2.4 Analysis of all vicinally connected protons
87(1)
2.2.5 Stereochemical elucidation
87(1)
2.3 13C-NMR of sesquiterpenes
88(2)
Section 3 Artemisinin---Chemistry, Pharmacology, and Clinical Uses
90(1)
3.1 Chemical properties of artemisinin
90(1)
3.2 Spectra analysis of artemisinin
91(2)
3.2.1 1H-NMR and 13C-NMR spectra of artemisinin
91(1)
3.2.2 HMQC and HMBC spectra
92(1)
3.3 Pharmacology and clinical uses of artemisinin and its derivatives
93(1)
3.4 Chemical modification and structural-activity relationship of artemisinin
93(8)
Section 4 Recent Progress of Specific Sesquiterpenes
96(3)
References
99(2)
Chapter 6 Diterpenes
101(24)
Section 1 Main Diterpene Skeletons
101(1)
Section 2 Biogenesis
102(1)
Section 3 Labdanes
103(3)
Section 4 Clerodanes
106(2)
Section 5 Pimaranes
108(1)
Section 6 Abietanes
108(2)
Section 7 Cassanes and Totaranes
110(1)
7.1 Cassanes
110(1)
7.2 Totaranes
111(1)
Section 8 Rosanes
111(1)
Section 9 Kauranes
112(1)
9.1 C-20-non-oxygenated-ent-kauranes
112(1)
9.2 C-20 oxygenated-ent-kauranes
113(1)
9.3 Seco-kauranes
113(2)
Section 10 Taxanes
115(1)
10.1 Taxol
115(1)
10.2 Taxotere
116(9)
Section 11 Tiglianes, Ingenanes and Daphnanes
118(1)
Section 12 Jatrophanes and Lathyranes
119(1)
Section 13 Myrsinols and Euphorsctines
120(1)
Section 14 Ginkgolides and Pseudolaric Acid
121(1)
References
121(4)
Chapter 7 Saponins
125(22)
Section 1 Introduction
125(1)
Section 2 Extraction and Isolation of Saponins
125(1)
2.1 Chromatography using macroporous resin
125(1)
2.2 Chromatography using silica gel
126(1)
2.3 Reversed-phase chromatography
126(1)
2.4 Liquid-liquid partition chromatography
126(1)
Section 3 Structure Determination of Saponins
126(1)
3.1 Cleavage of glycosidic bond
126(2)
3.1.1 Acidic hydrolysis
127(1)
3.1.2 Two-phase acid hydrolysis (mild acid hydrolysis)
127(1)
3.1.3 Smith degradation
127(1)
3.1.4 Enzymatic hydrolysis
127(1)
3.1.5 Alkaline hydrolysis
128(1)
3.2 Structure determination of saponins by chromatography
128(1)
3.2.1 Silica gel thin-layer chromatography
128(1)
3.2.2 Gas chromatography
128(1)
3.3 Structure determination of saponins by spectroscopy
128(2)
3.3.1 Mass spectrum
128(1)
3.3.2 Nuclear magnetic resonance spectrum
129(1)
Section 4 Biological Activity of Saponins
130(1)
4.1 Anti-tumor and cytotoxic effects
130(1)
4.2 Immunomodulatory activity
131(1)
4.3 Antimicrobial effects
131(1)
4.3.1 Antiviral activity
131(1)
4.3.2 Antifungal activity
131(1)
4.4 Cardiovascular activity
131(1)
4.5 Anti-inflammatory, anti-exudative, and anti-edema effects
132(1)
4.6 Other effects
132(1)
Section 5 Triterpenoid Saponin
132(1)
5.1 Triterpenoid
132(1)
5.2 Main structural skeletons of triterpenoid saponins
132(6)
5.2.1 Tetracyclic triterpenoids
132(4)
5.2.2 Pentacyclic triterpenoids
136(2)
5.3 Spectroscopic analysis of triterpenoids
138(1)
5.3.1 Ultraviolet spectrum
138(1)
5.3.2 Infrared spectrum
138(1)
5.3.3 Mass spectrum
138(1)
5.3.4 Nuclear magnetic resonance spectrum
138(1)
Section 6 Steroidal Saponins
139(1)
6.1 Steroidal aglycones
139(1)
6.2 Spectroscopic analysis of steroidal aglycones
140(1)
6.2.1 Ultraviolet spectrum
140(1)
6.2.2 Infrared spectrum
140(1)
6.2.3 Mass spectrum
140(1)
6.2.4 Nuclear magnetic resonance spectrum
141(1)
6.3 Spirostanol saponins
141(1)
6.4 Furostanol saponins
142(1)
6.5 Furospirostanol saponins
143(4)
Bibliography
143(1)
References
143(4)
Chapter 8 Amino Acids and Peptides
147(22)
Section 1 Amino Acids
147(1)
1.1 Structure and classification of amino acids
147(2)
1.2 Physical properties of amino acids
149(1)
1.3 Chemical properties of amino acids
150(2)
1.3.1 Acylation
150(1)
1.3.2 Reaction with CO2
150(1)
1.3.3 Formation of Schiff base
151(1)
1.3.4 Alkylation
151(1)
1.3.5 Reactions involving both amino and carboxyl groups
152(1)
1.3.6 Interaction with metal ions
152(1)
1.4 Purification and Characterization of Amino Acids
152(5)
1.4.1 Color reaction
152(1)
1.4.2 Techniques in isolation and analysis
153(2)
1.4.3 Infrared spectroscopy
155(1)
1.4.4 Mass spectroscopy
155(1)
1.4.5 Identification of succinamopine
156(1)
Section 2 Peptides
157(1)
2.1 Structures and properties of peptides and proteins
157(2)
2.2 Natural bioactive peptides
159(10)
2.2.1 Purification and identification of peptides
160(2)
2.2.2 Synthesis of peptides
162(3)
References
165(4)
Chapter 9 Flavonoids
169(20)
Section 1 Overview
169(1)
1.1 General structures and categories of flavonoids
169(1)
1.2 Physical and chemical properties of flavonoids
170(1)
1.3 The presence of flavonoids in plants
170(2)
1.3.1 Flavones and flavanones
171(1)
1.3.2 Flavonols and flavanonols
171(1)
1.3.3 Chalcones and dihydrochalcones
171(1)
1.3.4 Isoflavones and isoflavanones
171(1)
1.3.5 Anthocyanidins
172(1)
1.3.6 Flavanols
172(1)
1.3.7 Aurones
172(1)
1.3.8 Biflavonoids
172(1)
1.3.9 Other flavonoids
172(1)
Section 2 Extraction and Isolation of Flavonoids
172(1)
2.1 Extraction
172(1)
2.1.1 Hot water extraction
173(1)
2.1.2 Methanol or ethanol extraction
173(1)
2.1.3 Succession solvent extraction
173(1)
2.1.4 Alkaline water or alkaline diluted alcohol extraction
173(1)
2.2 Isolation
173(1)
2.3 New extraction and isolation methods
173(2)
2.3.1 Ultrasonic extraction
173(1)
2.3.2 Ultrafiltration
174(1)
2.3.3 Macroporous adsorption resin chromatography
174(1)
2.3.4 Aqueous two-phase extraction
174(1)
2.3.5 Supercritical fluid extraction
174(1)
2.3.6 Enzymic extraction
174(1)
2.3.7 High-performance liquid chromatography
174(1)
2.3.8 Micellar thin layer chromatography and microemulsion thin layer chromatography
175(1)
2.3.9 Molecular imprinting technology
175(1)
2.3.10 Other isolation techniques
175(1)
Section 3 Identification and Structure Study of Flavonoids
175(1)
3.1 Identification
175(1)
3.1.1 Physical and chemical identification
175(1)
3.1.2 Thin-layer chromatography and spectral identification
176(1)
3.2 Structure study
176(7)
3.2.1 Spectral features of flavonoids
176(2)
3.2.2 Flavonoid aglycone structure study
178(3)
3.2.3 Structure study for flavonoid glycosides
181(2)
Section 4 Pharmacological Study of Flavonoids
183(1)
4.1 Cardiovascular system activity
183(1)
4.2 Anti-microbial and anti-virus activity
183(1)
4.3 Anti-tumor activity
183(1)
4.4 Anti-oxyradical activity
183(1)
4.5 Anti-inflammatory and analgesia activity
184(1)
4.6 Hepatoprotective activity
184(1)
Section 5 Flavonoid Assay Determination and Formulation
184(1)
5.1 Flavonoid assay determination
184(2)
5.1.1 Ultraviolet spectrophotometry (UV)
184(1)
5.1.2 Thin-layer chromatography scanning (TLC scan)
184(1)
5.1.3 HPLC
185(1)
5.1.4 Capillary electrophoresis (CE)
186(1)
5.2 Flavonoid formulations
186(3)
Section 6 Conclusion
187(1)
References
187(2)
Chapter 10 Anthraquinones
189(16)
Section 1 Introduction
189(1)
1.1 Structure
189(4)
1.1.1 Monosubtituted anthraquinones
189(1)
1.1.2 Disubstituted anthraquinones
190(1)
1.1.3 Trisubtituted anthraquinones
190(1)
1.1.4 Tetrasubstituted anthraquinones
191(1)
1.1.5 Pentasubstituted anthraquinones
192(1)
1.1.6 Hexasubstituted and heptasubstituted anthraquinones
192(1)
1.1.7 Anthracyclinones
192(1)
1.2 Biological activity
193(1)
Section 2 Physical and Chemical Properties
194(1)
2.1 Physical properties
194(1)
2.2 Coloration
194(1)
2.3 Acidity
194(1)
Section 3 Extraction and Isolation
195(1)
3.1 Extraction
195(1)
3.1.1 Extraction with organic solvent
195(1)
3.1.2 Treatment with lead salt
195(1)
3.1.3 Acido-basic treatment
195(1)
3.2 Isolation
195(2)
Section 4 Spectral Characteristics
197(1)
4.1 UV
197(1)
4.2 IR
197(1)
4.3 MS
198(1)
4.4 NMR
198(1)
Section 5 Examples
199(1)
5.1 Anthraquinones from Rhynchotechum vestitum
199(3)
5.2 Anthraquinones from Rheum hotaoense
202(1)
5.3 Anthraquinones in Morinda elliptica
202(3)
References
203(2)
Chapter 11 Coumarins
205(20)
Section 1 Introduction
205(1)
Section 2 Structural Types
206(1)
2.1 Simple coumarins
206(1)
2.2 Furanocoumarins
207(1)
2.2.1 6,7-Furanocoumarins
208(1)
2.2.2 7,8-Furanocoumarins
208(1)
2.3 Pyranocoumarins
208(1)
2.3.1 6,7-Pyranocoumarins
208(1)
2.3.2 7,8-Pyranocoumarins
208(1)
2.4 Other coumarins
209(3)
2.4.1 3- or 4-Phenylcoumarins and 3,4-Benzocoumarins
210(1)
2.4.2 4-Hydroxycoumarin derivatives
210(1)
2.4.3 Calanolides
211(1)
Section 3 Physical and Chemical Properties
212(1)
3.1 Fluorescence
212(1)
3.2 Reactions with alkali
212(1)
3.3 Reactions with acid
213(1)
3.3.1 Alkene hydration
213(1)
Section 4 Isolation
213(1)
4.1 Extraction
213(1)
4.2 Lactone separation
214(1)
4.3 Fractional crystallization
214(1)
4.4 Vacuum sublimation and steam distillation
214(1)
4.5 Chromatographic methods
214(1)
4.5.1 Column chromatography
215(1)
4.5.2 Other chromatographic techniques
215(1)
4.5.3 High-performance liquid chromatography
215(1)
Section 5 Spectroscopic Identification
215(1)
5.1 Ultraviolet spectroscopy
215(2)
5.1.1 Alkylcoumarins
216(1)
5.1.2 Oxygenated coumarins
216(1)
5.1.3 Spectral shifts
216(1)
5.1.4 Furanocoumarins
216(1)
5.2 Infrared spectroscopy
217(1)
5.2.1 C---H stretching frequencies
217(1)
5.2.2 C=O stretching frequencies
217(1)
5.2.3 C=C skeletal vibrations
217(1)
5.2.4 Other absorptions
217(1)
5.3 Nuclear magnetic resonance spectroscopy
218(2)
5.3.1 1 H-NMR
218(1)
5.3.2 13C-NMR
219(1)
5.3.3 2D-NMR
220(1)
5.4 Mass spectrometry
220(1)
5.4.1 Simple coumarins
220(1)
5.4.2 Furanocoumarins and pyranocoumarins
221(1)
Section 6 Research example
221(1)
6.1 Plant material
221(1)
6.2 Extraction and isolation
222(1)
6.3 Structural Determination
222(3)
References
223(2)
Chapter 12 Lignans
225(22)
Section 1 Introduction
225(1)
1.1 Nomenclature
225(2)
1.2 Biosynthesis of lignans
227(1)
1.3 Isolation and identification
228(3)
1.3.1 UV spectrum
229(1)
1.3.2 IR spectrum
230(1)
1.3.3 Nuclear magnetic resonance (NMR) spectroscopy
230(1)
Section 2 Structural Types and Characteristics of Lignans
231(1)
2.1 Dibenzylbutanes
231(1)
2.2 Dibenzylbutyrolactones
231(2)
2.3 Arylnaphthalenes
233(1)
2.4 Tetrahydrofurans
234(3)
2.5 2,6-Diaryl-3,7-dioxabicyclo[ 3,3,0]octanes
235(2)
2.6 Dibenzocyclooctenes
237(1)
2.7 Benzofurans
238(1)
2.8 Bicyclic (3,2,1)-octanes
239(1)
2.9 Benzodioxanes
239(1)
2.10 Biphenyl derivatives
239(1)
2.11 Oligomeric lignans
240(1)
2.12 Miscellaneous
240(2)
Section 3 Bioactivities of Lignans
242(1)
3.1 Anti-tumor
242(1)
3.2 Anti-virus
243(1)
3.3 Cardioprotective effects
243(1)
3.4 Hepatoprotective effects
243(1)
3.5 Miscellaneous
243(4)
References
244(3)
Chapter 13 Other Natural Bioactive Compounds
247(22)
Section 1 Sulfur Compounds
247(1)
1.1 Allicin and Diallyltrisulfide
247(2)
1.2 Bioactive components in scallions and onions
249(1)
1.3 Rorifone
249(2)
1.4 Other natural sulfur products
251(1)
Section 2 Cyanide Compounds
251(1)
2.1 Amygdalin
252(1)
2.2 Sarmentosin and isosarmentosin
253(5)
Section 3 Coixenolide
254(1)
Section 4 Resveratrol
255(1)
Section 5 Muscone
256(2)
Section 6 Cardiac Glycosides
258(1)
6.1 Introduction
258(2)
6.2 Characteristics and detection of cardiac glycosides
260(1)
6.2.1 Lieberman-Burchard reaction
260(1)
6.2.2 Kedde reaction
260(1)
6.2.3 Keller-Kiliani reaction
260(1)
6.3 Extraction and separation of cardiac glycosides
260(1)
6.4 The structures of cardiac glycosides
261(1)
6.4.1 Sugar moiety of cardiac glycosides
261(1)
6.4.2 Aglycones of cardiac glycosides
261(1)
6.5 Spectroscopy of cardiac glycosides
262(1)
6.6 Cardiac glycosides of Digitalislanata
263(6)
6.6.1 Extraction of cedilanid
264(1)
6.6.2 Extraction of digoxin
265(1)
Bibliography
266(1)
References
266(3)
Chapter 14 Marine Natural Products
269(24)
Section 1 Introduction
269(2)
Section 2 Marine plants
271(1)
2.1 Mangrove plants
271(1)
2.2 Seaweeds (Algae)
272(5)
2.2.1 Rhodophyta (red algae)
273(1)
2.2.2 Phaeophyta (brown algae)
274(2)
2.2.3 Chlorophyta (green algae)
276(1)
Section 3 Marine Invertebrates
277(1)
3.1 Coelenterata (Coelenterates)
277(5)
3.1.1 Gorgonacea (gorgonians)
278(2)
3.1.2 Alcyonacea (soft corals)
280(1)
3.1.3 Hexacorallia (hexacorals)
281(1)
3.2 Porifera (Spongia)
282(3)
3.3 Mollucsca (Molluscs)
285(8)
Section 4 Marine Microorganisms and Phytoplankton
286(1)
Section 5 Miscellaneous
286(1)
Section 6 Examples
287(1)
Section 7 Epilogue (Outlook)
288(1)
References
289(4)
Chapter 15 Structural Modification of Active Principles from TCM
293(26)
Section 1 Introduction
293(1)
Section 2 Anti-malarial Drug Artemether
293(3)
Section 3 Anti-hepatitis Drug Bifendate
296(1)
Section 4 Anti-AD Drug Huperzine A
297(2)
Section 5 Anti-arrhythmia Drug Changrolin
299(2)
Section 6 Anti-neoplastic Drugs
301(1)
6.1 Podophyllotoxin, etoposide and teniposide
301(2)
6.2 Camptothecin
303(2)
6.3 Vinca Alkaloids
305(2)
6.4 Taxol
307(2)
6.5 Cantharidin
309(1)
6.6 Indirubin
310(9)
Section 7 Computer-aided Drug Design and Structural Modification
311(2)
References
313(6)
Chapter 16 Chemical Synthesis of Natural Products
319(28)
Section 1 Alkaloids
320(1)
1.1 Morphine
320(1)
1.2 Strychnine
321(1)
1.3 Camptothecin
322(2)
1.4 Reserpine
324(1)
1.5 Maytansine
325(3)
Section 2 Terpene
328(1)
2.1 Monoterpene---menthol
328(1)
2.2 Sesquiterpene---artemisinin
329(1)
2.3 Diterpene---tanshinones, triptolide
330(3)
Section 3 Flavonoids
333(1)
3.1 Synthesis of chalcones and dihydroflavonoids
333(1)
3.2 Synthesis of flavonoids and flavonols
334(2)
3.2.1 Baker-Venkatereman's method
334(1)
3.2.2 Algar-Flynn-Oyamada's method
334(1)
3.2.3 Synthesis of isoflavone
335(1)
Section 4 Synthesis of Anthraquinones
336(1)
4.1 Friedel-Crafts acylation
336(1)
4.2 Michael addition
337(1)
4.3 Diels-Alder method
337(1)
4.4 Ortho-metallization of N, N-diethylbenzamide
337(1)
Section 5 Lignans
338(1)
5.1 Podophyllotoxin
338(1)
5.1.1 Cascade 1,4-1,2 addition approach
338(1)
5.1.2 Diels-Alder reaction approach
339(1)
5.2 Schizandrin
339(4)
Section 6 Synthesis of Macrolide Antibiotics
342(1)
6.1 Oleandomycin
343(1)
6.2 Fluvirucin B1
344(1)
6.3 Macrolatin A
345(2)
Bibliography 347(1)
References 347(4)
Index 351
Ren-Sheng Xu, Professor of Shanghai Institute of Materia Medica, Chinese Academy of Sciences. Yang Ye, Professor of Shanghai Institute of Materia Medica, Chinese Academy of Sciences. Wei-Min Zhao, Professor of Shanghai Institute of Materia Medica, Chinese Academy of Sciences.