INDEX 365 Dihydrokaempferol, and isoflavone Electrocyclic addition, in nonadride biosynthesis, 73, 74 biosynthesis, 188 3,10 - Dihydroperylene - 4,9 - quinone, Electronic spectra of annulenes, and biosynthesis of, 119 conjugation in cyclo-octatetra­ 3,4-Dihydroxybenzoic acid, inac­ ene,297,298 tivity of, in vitamin K2 biosyn­ Franck-Condon effect in, 307 thesis, 164 influence of bond-alternation, 2,4 -Dihydroxy - 5,6 -dimethylbenzoic 305-9 acid, in aurantiogliocladin bio­ Eleodes longicollis, benzoquinone bio­ synthesis, II 0 synthesis in, 112 in flavipin biosynthesis, 91 Emodin, 180 incorporation into, 84 lloc,15 - Dihydroxy - 9 -ketoprost - 5- Enamines, in synthesis of bicyclic enoic acid, biosynthesis of, 179 compounds, 203-5,238 1,8-Dihydroxynaphthalene, in phenol Enol-lactones, in synthesis of bicyclic coupling reactions, 119 compounds,209-10 1,3-Dihydroxy-2-propanone phos- Ergochrome AB, biosynthesis of, 97 phate, in shikimic acid biosyn­ Ergosterol, biosynthesis of, 170 thesis, 132 Ergot, ergo chrome biosynthesis in, 97, 3,6 -Dihydroxy -2,5 -toluquinone, bio­ 198a synthesis of, III D-Erythrose 4-phosphate, in shikimic Dimethylacetothetin, methylations acid biosynthesis, 132 by,85 Escherichia coli, mutants of, in studies 3,3-Dimethylallyl diphenyl phos­ of amino acid biosynthesis, 128 ff phate, alkylation of phenols, by vitamin K2 biosynthesis in, 164 161 Ethionine, suppression of tropolone Dimethylallyl pyrophosphate, in ter­ biosynthesis by, 105 pene and steroid biosynthesis, 2-Ethylbenzoquinone, biosynthesis of, 158,159 112 in humulone biosynthesis, 159 Ethyl diazoacetate, ring expansion 2,2-Dimethylchroman, formation of, with,106 161 Eucalyptus species, polyketide bio­ Dimethyl xanthophanic enol, base synthesis in, 108 catalysed cyclisation of, 126 Euglena gracilis, terpenoid benzo­ Diterpenes, biosynthesis of, 159 quinone biosynthesis in, 164 Dryopteris marginalis, margaspidin Evernia vulpina, vulpinic acid bio­ biosynthesis in, 89 synthesis in, 147 Dryopteris species, methylenebisphlo­ roglucinol biosynthesis in, 87 Farnesyl diphenyl phosphate, alky­ Duclauxin, biosynthesis of, 91 lation by, 161 Farnesyl pyrophosphate, in cannabis constituent biosynthesis, 159 5,8, ll, 14, 17 -Eicosapentaenoic acid, in terpene biosynthesis, 159 in prostaglandin biosynthesis, Fatty acids, biosynthesis of, 78 ff, 126 178 Feist's acid, 249 ff 5, 8, 11, 14 - Eicosatetraenoic acid, see bond-lengths, 256 arachidonic acid, 176 derivatives, 255 8,1l,14-Eicosatrienoic acid, in pros­ dibromo-, 261 taglandin biosynthesis, 178 preparation, 253 366 INDEX Feist's acid-cont. Gliocladium roseum, aurantiogliocla­ reactions of, 257 ff din biosynthesis in, no related compounds, 266 D-Glucose, in aromatic amino acid spectra, 256 biosynthesis, 128 ff Fermi resonance, 218 in gallic acid biosynthesis, 144 Ferriprotoporphyrin IX, prosthetic in myo-inositol biosynthesis, 180 group in chloroperoxidase, 175 in L-viburnitol biosynthesis, 183 Ferulic acid, from sinapic acid, 145 Glucose 6-phosphate, in myo-inositol Flavanone-chalcone interconversion, biosynthesis, 180 67 trans - 2 - Glucosyloxy - 4 - methoxy­ Flavesone, biosynthesis of, 109 cinnamic acid, in herniarin bio­ Flavipin, biosynthesis of, 90, 91 synthesis, 138 Flavonoids, biosynthesis of, 148 ff Glucuronic acid, biosynthesis of, from Formononetin, biosynthesis of, 74 myo-inositol, 183 Fructose 1,6-diphosphate, in shikimic Glutamine, in formation of anthranilic acid biosynthesis, 132 acid from chorismic acid, 134 Fumigatin, biosynthesis of, III Gossypol, biosynthesis of, 119 Furanocoumarins, biosynthesis of, Grandiflorone, biosynthesis of, 109 140 Griseofulvin, biosynthesis of, 94-7 Furan ring, formation of in furano­ polyketide nature of, 77 coumarins, 140 synthesis of, 96, 97 Gymnosperm lignin, structure of, 142 Gallic acid, biosynthesis of, 144-5 Gaultheria procumbens, benzoic acid Heat of formation and aromaticity, of biosynthesis in, 142 [18]annulene, 309 General acid catalysis of benzidine of biphenylene, 321-3 rearrangements, 13 of cyclo-octatetraene, 296, 297 Gentisaldehyde, in patulin biosyn­ D-altro-Heptulose 1,7 -diphosphate, in thesis, 121 shikimic acid and aromatic amino Gentisic acid, biosynthesis of, 142 acid biosynthesis, 130 ff Geodin, formation from dihydrogeo­ Hibiscus syriacus, cyclopropene fatty din of, 96 acid biosynthesis in, 170 conversion into geodin hydrate, 96 Herniarin, biosynthesis of, 138 Geodin hydrate, conversion into geo­ Homo-y-linolenic acid, see 8,11,14- doxin of, 96, 139 eicosatrienoic acid, 178 formation from geodin of, 96 Hop constituents, biosynthesis of, 159 Geodoxin, formation from geodin Hordeum species, aromatic acid bio- hydrate of, 96, 139 synthesis in, 145 Geranium pyrenaicum, gallic acid Huckel's rule, 270-2 biosynthesis in, 144 Humulone, biosynthesis of, 159 Geranyl pyrophosphate, in terpene Hydrangea species, hydrangenol bio- biosynthesis, 159 synthesis in, 156 Geranylgeranylpyrophosphate, in ter- Hydrangenol, biosynthesis of, 156 pene biosynthesis, 159 Hydrazoarenes, basicity, 8 Gibberellafujikuroi,70 disproportionation by acids, 52 Gibberellins, 70 disproportionation by bases, 56 Glaucanic acid, biosynthesis of, 184-8 disproportionation by heat, 50 Glauconic acid, biosynthesis of, 184-8 disproportionation by u.v.light, 50 INDEX 367 Hydride transfer in bicyclononanes, Illicium dnisatum (I. religiosum), 226-7 shikimic acid in, 128 Hydroquinone glucoside, see Arbutin Impatiens balsamina, 2-hydroxy-l,4- 3-Hydroxyanthranilic acid, and 0- naphthaquinone biosynthesis in, pyrocatechuic acid biosynthesis, 166 145 Infra-red spectra of bicyclononanes, p-Hydroxybenzoic acid, biosynthesis 216, 218-21 of,142 CO doublets, 218-21 from caffeic acid, formation of, 145 D-Inositol, biosynthesis of, 180, 182 in arbutin biosynthesis, 146 L-Inositol, biosynthesis of, 182 in ubiquinone biosynthesis, 162-4 meso-Inositol, see myo-Inositol nutritional requirement of E. coli myo-Inositol, biosynthesis of, 180-2 mutants for, 128 in apiose biosynthesis, 183 m-Hydroxybenzyl alcohol, in patulin in biosynthesis of cell-wall poly­ biosynthesis, 121 saccharides, 183, 198b p-Hydroxycinnamic acid, in flavonoid myo-Inositol I-phosphate, intermedi­ biosynthesis, 148, 149 ate in myo-inositol biosynthesis, p-Hydroxy-trans-cinnamic acid, for­ 182 mation from tyrosine, 136 f3-Ionone, 208 p -Hydroxy -cis-cinnamic acid, in novo­ Iridoskyrin, biosynthesis of, 120 biocin biosynthesis, 139 Islandicin, biosynthesis of, 83 p-Hydroxycinnamyl alcohol, in lignin 180 incorporation into, 84 formation, 142 relationship to iridoskyrin of, p-Hydroxycinnamyl-CoA, in flavo­ 120 noid biosynthesis, 150 Isobutyryl-CoA, in tasmanone bio­ 11 CI. - Hydroxy - 9, 15 - diketoprost - 5 - synthesis, 108 enoic acid, biosynthesis of, 179 in grandifiorone biosynthesis, 109 5-Hydroxyisophthalic acid, degra­ Isoclovene, 214 dation of stipitatic acid to, 105 Isoflavones, biosynthesis of, 73-5 150, Hydroxylation, of aromatic sub­ 151, 198c strates, 143-6 L-Isoleucine, as precursor of branched (S) - 4' - Hydroxy - 4 - methoxydalber­ chain fatty acids, 107 gione, 154 Isopentenyl pyrophosphate, in ter­ CI. - Hydroxymethylserine, formation pene and steroid biosynthesis, of, 189 157, 158, 159 2 - Hydroxy - 1, 4 - naphthaquinone Isoprenylcoumarins, occurrence in (lawsone), biosynthesis of, 166 plants, 140 p-Hydroxyphenylpyruvic acid, for­ Isoprenylnaphthaquinones, occur- mation from prephenic acid of, rence of, 167 134 Isopropylfuranocoumarins, occur- inactivity of, in vitamin K2 bio­ rence in plants, 140 synthesis, 164 Isotope effects in benzidine rear­ 3-Hydroxyphthalic acid, biosyn­ rangements, kinetic, 16,46,48 thesis of, 83 product, 27 4-Hydroxypretetramid, in tetracy­ solvent, 16 cline biosynthesis, 113 Isovaleryl-CoA, in humulone biosyn­ 3-Hydroxy-2,5-toluquinone, biosyn­ thesis, 159 thesis of, III in leptospermone biosynthesis, 109 368 INDEX Jahn-Teller effect, definition, 276 Mammea americana, constituents of, examples, 277 155 in annulenes, 278-82 Margaspidin, biosynthesis of, 90 in cyclo-octatetraene derivatives, Membrane permeability, 72 302,303 Metal ions, in secondard metabolism, J avanicin, biosynthesis of, 98, 99, 115, 189 166 Methionine, as methyl donor, 84 in barnol biosynthesis, 86 Kaempferol, in isoflavone biosyn­ in duclauxin biosynthesis, 91 thesis, 73, 74 in flavipin biosynthesis, 91 ,8-Ketoadipicic acid, in caldariomycin in lactobacillic acid biosynthesis, biosynthesis, 174 170 16-Ketoprogesterone, enzymatic hal­ mechanism of methylation by, 171, ogenation of, 175 172 in methylenebisphloroglucinol bio­ Lactobacillus arabino8U8, lactobacillic synthesis, 87, 89 acid biosynthesis in, 170 in mycophenolic acid biosynthesis, Lavandula oificinalis, coumarin bio­ 86 synthesis in, 138 in tasmanone biosynthesis, 108 Lawsone, see 2-hydroxy-l,4-naphtha- in vitamin K2 biosynthesis, 165 quinone, 166 Methionine sulphoxide, 173 Leptospermone, biosynthesis of, 109 Methylaspidinol, in p-aspidin biosyn­ L-Leucanthemitol, 180 thesis, 87 Leucine, in humulone biosynthesis, formation of methylene-bisaspidi­ 159 nolfrom,88 Lignin, 140 ff Methylation, biological, mechanism Lucerne, coumestrol biosynthesis in, of, 170-3 152 a-Methylbutyryl-CoA, in branched Lycopodine, synthesis, 213 chain fatty acid biosynthesis, 107 Lysine, in l-amino-2-nitrocyclopen­ 3-Methyl-6-8-dihydroxyisocoumarin, tane carboxylic acid, biosyn­ synthesis of, 124 thesis, 173, 189 Methylenebisphloroglucinol, biosyn­ thesis of, 127 Machaerium scleroxylon, neoflavo­ Methylenecyclopropane - trans - 1, 2 - noids in, 154 dicarboxylic acid, see Feist's acid Macrolides,