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Chemistry of Natural Products: A Laboratory Handbook

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DAFTAR ISI

1. Introduction 1

2. A Survey of the methods of extraction, isolation and fractionation of naturally occurring organic compounds 5
2.1 selection of the material 5
2.2 extraction 7
2.3 fractionation using solvents 10
2.3.1 specific extraction and fractionation procedures 11
2.3.2 supercritical fluid extraction 16
2.3.3 chromatographic methods 17

3. characterisation of naturally occurring compounds 31
3.1 chemical methods 31
3.1.1 preliminary studies-colour reactions 31
3.1.2 detection and derivatisation of fuctional groups 36
3.2 spectral methods 40

4. Procedures for isolation of select compounds 43
4.1 bixin from bixa orellana seeds (annatto) 44
4.2 anthocyanins 49
4.2.1 isolation of cyanin from red roses 49
4.2.2 a blue pigment from a blue flower 50
4.3 flavonoids 54
4.3.1 isolation of nepitrin from nepeta hindustana 55
4.3.2 isolation of pedaliin 59
4.3.3 isolation of hesperidin 61
4.3.4 isolation of a biflavone-cupressuflavone 63
4.3.5 isolation of catechins from green tea 65
4.4 isoflavanones 67
4.4.1 isolation of homoferreirin from ougenia dalbergioides 68
4.4.2 isolation of ougenin 69
4.5 xanthones 70
4.5.1 isolation of mangiferin 71
4.6 betanins 72
4.6.1 isolation of crude betanins from bougainvillea flowers 73
4.7 quinones 73
4.7.1 isolation of lawsone from lawsonia alba 75
4.7.2 isolation of morindonin 76
4.8 essential oils 88
4.8.1 isolation of limonene 88
4.8.2 isolation of geraniol 83
4.8.3 isolation of citronellal 84
4.8.4 isolation of a-pinene 85
4.8.5 isolation of citral 87
4.8.6 isolation of carvone 87
4.9 higher terpenoids 89
4.9.1 isolation of all the triterpenoids in birchwood bark 91
4.9.2 isolation of lupeol-column chromatography of crude betulin 94
4.9.3 isolation of sitosterol 95
4.10 non-terpenoid components of essential oils 95
4.10.1 isolation of eugenol 96
4.11 alkaloids 97
4.11.1 isolation of nicotine 100
4.11.2 isolation of piperine 101
4.11.3 isolation of a purine derivative 101
4.11.4 isolation of xanthosine 102
4.12 oxygen heterocyclics other than flavonoids 103
4.12.1 isolation of psoralen 103
4.12.2 isolation of wedelolactone desmethylwedelolactone 105

5. Chemical transformations of some natural products 109
5.1 hydroxycitronellal from citronellal 109
5.2 citral from geraniol 112
5.3 synthetic lime mix from citral 113
5.4 citral to pseudo-ionone 115
5.5 pseudo-ionone to a-ionone 115
5.6 b-ionone from pseudo-ionone 116
5.7 a-terpineol from a-pinene 117
5.8 a-pinene to camphor quinone 118
5.9 calophyllolide to 2,2,-dimethyl-5-hydroxy-7,8-(4'-phenyl-a-pyreno) chroman 121
5.10 conversion of methyl esters of tiglic acid and angelic acid into their epoxy derivatives 122
5.11 nitration and other reactions of osthol 124

6. Synthesis of select compounds 136
6.1 flavanone 137
6.2 7-hydroxyflavone 139
6.3 desmethylwedelolactone 140
6.4 lawsone 142
6.5 terthienylmethanol 145
6.6 nordalbergin 150
6.7 2-hydroxy-4-methoxybenzaldehyde 152
6.8 umbelliferone, herniarin and 7-methoxy-8-allylcoumsrin 154
6.9 a-methoxy-2,4 dihydroxyacetophenone and a-methoxy-2,4,6-trihydroxyacetophenone 157

7. Metabolism of natural products 161
7.1 experimental methods used in studies on drug metabolism 162
7.2 biochemical transformation of natural products 166
7.2.1 isolation of bakuchiol 169

8. Suggested projects 173
8.1 analysis of the citral content in different samples of lemon grass (cymbopogon citratur) 173
8.2 analysis of carvone content in different samples of caraway 176
8.3 study of antifungal activities of plant extracts and some isolated compounds 177
8.4 chromatographic study of anthocyanin pigments in tulip 180
8.5 chromatographic study of some marine algae 182
8.6 a chemotaxonomic study of some species of parmelia lichens 185
8.7 gas chromatography-mass spectroscopic study (GC-MS) of some sweet smelling woods 185
8.8 essential oils from citrus species 187
8.9 examination of ayurvedic patent preparations containing bhringraj for wedelolactone-desmethylwedelolactone 188

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Series Title

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Call Number

615.3-1 Kri C

Publisher

India : CRC Press., 2012

Collation

ed.2-cet.1. xviii, 204 hal. : ilus. ; 23 cm Index.

Language

Indonesia

ISBN/ISSN

978-1-4665-0524-7

Classification

615.3-1 Kri C

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NULL

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