Ecology and Metabolism of Plant Lipids

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Author Index Lichtenthaler, Hartmut Κ., 109 Lozano, Ruben, 187, 200 Lusby, William R., 200 Meudt, Werner J., 53 Moreau, Robert Α., 343 Mudd, J. B., 10 Nes, W. David, 2, 140, 304 Nes, William R., 252 Parish, Edward J., 140 Phinney, B. 0., 25 Poralla, Karl, 239 Roddick, James G., 286 Sanchez, J., 10 Soliday, Charles L., 152 Sparace, S. Α., 10 Spray, C. R., 25 Stumpf, P. Κ., 44 Svoboda, James Α., 176, 187, 200 Thomas, S., 10 Thompson, Malcolm J., 176, 187, 200 Weete, John D., 268 Weirich, Gunter F., 187 Woloshuk, Charles P., 152

Andrews, J., 10 Bach, Thomas J., 109 Bishop, D. G., 10 Bradford, Susan, 140 Chitwood, David J., 200 Cihlar, Ronald L., 355 Crawford, Mark S., 152 Croteau, Rodney, 76 Elakovich, S t e l l a D., 93 Ettinger, William F., 152 Feldlaufer, Mark F., 187 F u l l e r , Glenn, 2, 44 Geisler, V i c t o r i a J., 140 Hanners, Patrick Κ., 140 Heupel, Rick C , 140 Hoberg, Kathryn Α., 355 Johnson, Mark Α., 76 Kabara, Jon J., 220 Kannenberg, Elmar, 239 Kerwin, James L., 329 Kleppinger-Sparace, 10 Kolattukudy, P. E., 152 Le, Phu H., 140

Subject Index A

Abies grandis, interactions with the f i r engraver beetle, 79 Absidia coerulea, phosphorylation of compactin, 115 Absidia cylindrospora, phosphorylation of compactin, 115 Absidia glauca, phosphorylation of compactin, 115 Acetyl coenzyme A, formation, 45 Achlya, s t e r o l u t i l i z a t i o n , 318,321 Achlya ambisexualis, growth i n h i b i t i o n , 337 Achlya c a r o l i n i a n a growth i n h i b i t i o n , 337 Acyl c a r r i e r protein, fatty acid synthase sequence, 45-46 Acyl c a r r i e r protein derivatives, desaturation, 13,l4f Acyl l i p i d s , formation, 47-48 Aglycone skeletons saponins, 288f Solanum glycoalkaloids, 288f t

Allelopathic agents, structure, 98f Alternaria solani, removal of mono saccharide units of glycoalkaloids, 297,299 Ambrosia psilostachya, production of sesquiterpene lactones, 104 Antifungal a c t i v i t y , plant steroids, 286-301 Antifungal azoles, names, 270-271t Aphelenchus avenae, ecdysteroids, 214 Apis mellifera, effect of sterols on brood production, 183 Artemisia absinthium, sesquiterpene inhibitor production, 104 Ascaris, s t e r o l biosynthesis, 202-203 Ascaris suum, ecdysteroids, 214 Aspergillus nidulans, studies of s t e r o l i n h i b i t o r s , 276-277 Aspergillus niger, studies of fatty acids, 222,223 Aspergillus ochraceous, temperature adaptation, 332 Aspergillus terreus, production of mevinolin, 110

366 Fuller and Nes; Ecology and Metabolism of Plant Lipids ACS Symposium Series; American Chemical Society: Washington, DC, 1987.

367

INDEX

Aubergenone, structure, 95 f Auxin-brassinolide interaction, 64-67 Azole s t e r o l i n h i b i t o r s , 276,277t

B Bacillus acidocaldarius, hopanoid and l i p i d content, 244-247 Bacillus s u b t i l i s , reproduction of Turbatrix a c e t i , 201 Bark beetle attack, biochemistry of conifer resistance, 78-79 Bioassays, quantitative, brassinosteroids, 61-64 Bisabolene, structure, 98f Bombyx mori, metabolism of dietary sterols, 177 Botryodiploidia theobromae, use of cerulenin to distinguish, 356 Botrytis cinerea, t o x i c i t y of glycosides, 290,295-299 Brassica compestris, presence of 28-norbrassinone, 59 Brassica napus, b i o l o g i c a l l y active agent, 53 Brassinolide b i o l o g i c a l a c t i v i t y , 59 chemical and b i o l o g i c a l aspects, 53-73 effect on crop production, 70-73 effect on geotropism, 70,71f effect on growth of p u l v i n i , 70,72f effect on proton secretion, 67 structure, 55,56f Brassinolide-auxin interaction, 64-67 Brassinolide-ethylene interaction, 67-70,71f Brassinolide-gibberellic acid interaction, 67-69 Brassinosteroids bean f i r s t internode bioassay, 62-64 bean second internode bioassay, 61-62 natural occurrence i n plants, 55 quantitative bioassays, 61-64 rice-lamina i n c l i n a t i o n test, 62 structure, 55,58f Bremia lactucae, i n f e c t i o n of lettuce, 344 Brugia pahangi, s t e r o l biosynthesis, 202 Bursaphlenchus xylophilus, amine t o x i c i t y , 205 Butyrate, investigations concerning biochemical correlates of germination, 360-362

C Caenorhabditis, n u t r i t i o n a l requirement for sterols, 201-203 Caenorhabditis elegans effects of i n h i b i t o r s on s t e r o l metabolic pathways, 208-213 general discussion, 202-205,208 Calliphora v i c i n a , ecdysone conversions, 189 Campesterol, structure, 179f Candida albicans cerulenin-resistant mutants, 362-364 effect of cerulenin and butyrate on germination, 357-360 growth i n h i b i t i o n , 276,278 morphogenesis and pathogenesis, 356 photomicrographs, 358f ultrastructure, 359f Candida l i p o l y t i c a , f a t t y acid biosynthesis, 332 Candida u t i l i s , temperature adaptation, 332 Capsenone, structure, 95f Capsicum annuum, as a source of sesquiterpenoid phytoalexin, 100 Capsicum frutescens, use i n hostparasite studies, 101 Capsidiol, structure, 95f Caryophyllene, structure, 98f Castanea crenata, as a source of 6-deoxocastasterone, 59-60 Castasterone b i o l o g i c a l a c t i v i t y , 60 IUPAC equivalent name, 57 Cephalosporum caerulens growth regulation, 115 i n h i b i t i o n of fatty acid synthesis, 356 Ceramide aminoethylphosphonate, 347f Ceratocystis, growth i n h i b i t i o n , 81 Ceratocystis fimbriata, infection of sweet potatoes, 102 Ceratocystis ulmi infection of Wych elm, 103 use of cerulenin to distinguish, 356 Cercospora arachidicola, s t e r o l content, 274 Cerulenin, investigations concerning biochemical correlates of germination, 356,360-362 Chaetomium, growth of isolated compounds on acids, 334 Chaoborus astictopus, infection, 335 Chloroplast g l y c e r o l i p i d s , biosynthesis, 10-23 5,22,24-Cholestatrienol, structure, 179f Cholesterol, structure, 179f Chondrostereum purpureum, i n f e c t i o n of elm, 103 C i r c i n e l l a muscae, phosphorylation of compactin, 115

Fuller and Nes; Ecology and Metabolism of Plant Lipids ACS Symposium Series; American Chemical Society: Washington, DC, 1987.

368

ECOLOGY AND METABOLISM OF PLANT LIPIDS

Cladosporium fulvum, growth i n h i b i t i o n , 287 Coleoptera phytophagous insects that convert phytosterols to cholesterol, 180-182 phytophagous insects unable to convert phytosterols to cholesterol, 183 Colletotrichum, c a t a l y s i s of ester hydrolysis, 157 Colletotrichum c a p s i c i , spore suspensions, 163 Colletotrichum gloeosporiodes, cutinase secretion, 163,166 Colletotrichum graminicola, spore suspensions, 163 Colletotrichum orbiculare, growth i n h i b i t i o n , 290,295 Colletotrichum phomoides, resistance of tomato f r u i t s , 299 Compactin, structure, 112 Conifer resistance to bark beetles, biochemistry, 76-89 Conifer resistance to t h e i r fungal symbionts, biochemistry, 76-89 Coriolus versicolor, infection of elm, 103 Corticium r o l f s i i , f r u i t rot, 299 Corynebacterium sepedonicum, bacterial ring rot of potatoes, 298 Cotton—See Gossypium species Cucurbita maxima, 4-desmethylsterols, 253,254t Culex t a r s a l i s , infection, 335 Cutin, fungal interaction with plants, 152-173 Cutinase comparison of homologous peptides, 159,l62f i s o l a t i o n and characterization, 154-158 mechanism of c a t a l y s i s , 157,158f mRNA content, 170,171f nucleotide sequence, 159-161 role i n pathogenesis, 163-170 structure, 159 Cutinase a c t i v i t y e x t r a c e l l u l a r f l u i d of Fusarium solani p i s i , 170,171Γ released into the e x t r a c e l l u l a r f l u i d during spore germination, 166,168t Cyclooxygenase, regulation of fungal morphogenesis, 337-338 Cyperus serotinus, isolated inhibitory f r a c t i o n , 104 D Dacrydium cupressinum, i s o l a t i o n of podocarpic acid, 140

Datura stramonium, production of antifungal compounds, 102 Dehydroipomeamarone, structure, 96f Dendroctonus brevicomis, aggregation pheromone precursor, 79-80 Dendroctonus ponderosae, resistance of pine, 80 6-Deoxocastasterone b i o l o g i c a l a c t i v i t y , 59 IUPAC equivalent name, 57 Deoxodolichlosterone b i o l o g i c a l a c t i v i t y , 59 IUPAC equivalent name, 57 4-Desmethylsterols, Cucurbita maxima, 253,254t Diacylglycerol, biosynthesis, 18 Diacylglycerol moiety of chloroplast glycerolipids, 15-16 Dictyostelium discoideum, increases i n fatty acids during development, 335 Digalactosyldiacylgycerol, biosynthesis, 18 4a,5-Dihydrocompactin, structure, 112 4a,5-Dihydromevinolin, structure, 112 Diplodea pinea, i n h i b i t i o n of spore germination, 81 D i r o f i l a r i a immitis, s t e r o l biosynthesis, 202,214 Dolicholide b i o l o g i c a l a c t i v i t y , 60 IUPAC equivalent name, 57 Dolichos lablab, i s o l a t i o n of brassinosteroid, 59 Dolichosterone b i o l o g i c a l a c t i v i t y , 59-60 IUPAC equivalent name, 57 Dolico lablab, i s o l a t i o n of dolicholide, 60 Dysdercus fasciatus, s t e r o l metabolism, 183

Ε

Ecdysone IUPAC equivalent name, 57t structure, 178f Ecdysteroid(s) content i n meconium f l u i d , 191-194 embryonated eggs of Manduca sexta, 194-198 i s o l a t i o n from Manduca pupae, 192f i s o l a t i o n from Manduca sexta, 190f structure, 178f Eggplant—See Solanum melongena Electron micrographs, pea-stem c u t i c l e , I64f Elm—See Ulmus glabra 3-Epiecdysome, metabolic scheme, l89,190f Epilachna v a r i v e s t i s , s t e r o l content, 180


369

INDEX

Ergosterol biosynthesis, inhibitors, 268-282 Erynia delphacis, c o n i d i a l germination, 338 Erynia radicans, response to o l e i c acid, 336 Erynia v a r i a b i l i s , c o n i d i a l germination, 336,338 Escherichia c o l i acyl c a r r i e r protein, 45-46 effect on Caenorhabditis, 201 Esterase a c t i v i t y , released into the e x t r a c e l l u l a r f l u i d during spore germination, 166,168t Esters, antimicrobial i n s e c t i c i d a l agents, 220-236 Ethylene-brassinolide interaction, 67-70,71f Europhium clavigerum, resistance of conifers, 80,82

Fungitoxicity—Continued saponins, 287-291 Furanosesquiterpenoid stress metabolites from sweet potato, structure, 96f Fusarium caeruleum, disruption of spores, 290,298 Fusarium oxysporum, i n h i b i t i o n , 287,290,297-298 Fusarium solani p i s i bioassays on pea e p i c o t y l , 163-167 cutinase mRNA content, 170,171f degradation by fungal pathogens, 154 isolated enzyme, 159 nystatin-resistant mutants, 291 pectinase production, 172 penetration of pea-stem c u t i c l e , I63,l64f resin-flow induction, 81

G F Fannia c a n i c u l a r i s , germination on the cuticular surface, 336 Farnesol, structure, 96f,98f Farnesyl acetate, structure, 98f Fatty acids and fungal developments, 329-338 antimicrobial a c t i v i t y , 221-227 antimicrobial i n s e c t i c i d a l agents, 220-236 composition, temperature adaptation, 332-333 enzymic regulation, 331-332 e s t e r i f i c a t i o n , 224 fungi spore germination, 334-336 general discussion, 4-5 host-pathogen interactions, 336-337 membrane transport, 331 physical properties, 330-331 plants, a model system, 44-51 structure, discussion, 330 synthase sequence, 45-47 synthesis i n plants, 11-13,44-45 Foeniculum vulgare, monoterpene c y c l i z a t i o n , 87 Fomes annosus, growth i n h i b i t i o n , 81 Fucosterol, structure, 179f Fungal e l i c i t o r s and conifer resistance, 81-82 Fungal growth fatty acids, 333-334 i n h i b i t i o n by i n h i b i t o r s of ergosterol biosynthesis, 268-282 Fungal l i f e cycle, sequence of development controlled by sterols, 319f Fungitoxicity glycoalkaloids, 287-291

Galactolipids biosynthesis, 18-19 general discussion, 5,6t Geotrichum flavobrunneum a n t i b i o t i c i s o l a t i o n , 129 azasterol production, 269 Geotropism, effect of brassinolide, 70,71f Gibberella f u j i k u r o i early 3-hydroxylation pathway, 32,34f i s o l a t i o n of g i b b e r e l l i n s , 25 Gibberellic acid-brassinolide interaction, 67-69 Gibberellins biosynthesis, 29-41 p u r i f i c a t i o n steps, 26,28f Gloeosporium fructigenum, f r u i t rot, 299 Glutinosone, structure, 95f Glycerol-3-phosphate, acylation, 16-17 Glycoalkaloids as resistance factors, 297-300 fungitoxicity, 287-291 Gossypium species, as a source of sesquiterpenoid phytoalexins, 103 Gossypol, structure, 97f Growth i n h i b i t o r s , i n radish seedlings, 131,132f

H Haemonchus contortus, ecdysteroids, 214 Haliphthoros milfordensis, growth promotion by o l e i c acid, 334 Heliothis zea growth prevention of larvae, 260 metabolism of phytosterols, 177


370


Helminthosporium avenae, i n f e c t i o n of saponins, 297 Helminthosporium turcicum, growth i n h i b i t i o n , 290,295 Hemiptera, phytophagous insects unable to convert phytosterols to cholesterol, 180-181 28-Homobrassinolide b i o l o g i c a l a c t i v i t y , 60 IUPAC equivalent name, 57 28-Homodolicholide b i o l o g i c a l a c t i v i t y , 60 IUPAC equivalent name, 57 28-Homodoli chosterone b i o l o g i c a l a c t i v i t y , 60 IUPAC equivalent name, 57 Hopanoids B a c i l l u s acidocaldarius content, 244-245,247f function i n model membrane systems, 246-249 occurrence, 242-244,245f s t e r o l equivalents i n bacteria, 239-249 structures, 242,243f Zymomonas mobilis content, 246,247f 7-Hydroxycostal, structure, 96f 7-Hydroxycostoi, structure, 96f 11-Hydroxy-9,10-dehydronerolidol, structure, 95f 20-Hydroxyecdysone, structure, 178f 9-Hydroxynerolidol, structure, 95f Hymenoptera, phytophagous insects unable to convert phytosterols to cholesterol, 183-184

I Ipomeabisfuran, structure, 96f Ipomeamarone, structure, 96f Ipomoea batatus, as a source of sesquiterpenoid phytoalexins, 102 Ips typographis, production of aggregation pheromone, 80 ent-Isokaurene, 37,40f Isopentenoid compounds, 7

J Jimsonweed—See Datura stramonium

Κ ent-Kaurene, 37,40f

L Lactuca sativa, changes during infection, 344

Lagenidium giganteum, sporulation, 334-335,337-338 Lanosterol, i n h i b i t i o n of demethylation, 269-276 Laurie acid, structure, 4t Lemna minor as a plant model system, 48-50 d i s t r i b u t i o n of f a t t y acids, 49t labeled acetate incorporation, 49-51 Lepidoptera, phytophagous insects that convert phytosterols, 177,179f Leucosporidium, enhancement of l i n o l e i c acid, 332 L i n o l e i c acid, structure, 4t Lipids biosynthesis i n chloroplasts, 10-23 classes, 4-7 derived from f a t t y acids, 5 description, 3 interactions, 8,9f not derived from fatty acids, 7 overview, 2-9 polar, 5 L i p o l y t i c enzymes change i n l e v e l s , 350 during i n f e c t i o n , 350 L i p o p h i l i c antimicrobial agents, 221-227 Lipoxygenase, regulation of fungal morphogenesis, 337-338 Lippia n o d i f l o r i a , as a source of sesquiterpenoid phytoalexins, 104 Locusta migratoria, ecdysteroids, 189 Lycopersicon esculentum, as a source of sesquiterpenoid phytoalexins, 102 Lycopersicon pimpinellifolium, resistance to bacterial w i l t , 298

M Makisterone A, structure, 178f Malonyl coenzyme A, formation, 45 Manduca sexta free and conjugated ecdysteroids, 187-198 metabolism of s t e r o l s , 177 t o x i c i t y of 29-fluorostigmasterol, 202 Meconium f l u i d , ecdysteroid content, 191-194 Megachile rotundata, use of dietary phytosterols, 183 Meloidogyne incognita, i n h i b i t i o n of sterol metabolism, 205 Meterodera zeae, s t e r o l content, 204 24-Methylene-cholesterol, structure, Methylococcus capsulatus synthesis of hopanoids, 249 synthesis of s t e r o l s , 240,249


179f

371

INDEX

Mevalonic acid chemical structure, 7 early pathway to gibberellins-12-aldehyde, 29,30f Mevinolin effect on growth and chemical composition of c e l l suspension cultures of Silybum marianum, 126,127t effect on isoprenoid accumulation i n radish seedlings, 118-124 effect on isoprenoid synthesis i n primary leaves of wheat, 124,125t effect on p l a s t i d i c p r e n y l l i p i d s and prenylquinones, 122,123t plant-growth regulation, 109-134 secondary physiological responses, 126-129 structure, 112f Mevinolin-type metabolites, comparison of i n h i b i t i o n constants, 110,113-114t Microsporum gypseum, macroconidial germination, 335 Monacolin, structure, 112f Monascus ruber, mevinolin production, 110 Monilinia f r u c t i c o l a , inoculation of peppers, 101-102 Monilinia fructigena f r u i t rot, 299 sterol i n h i b i t o r studies, 276,278 Monogalactosyldiacylglyceride, substrate, 47 Monogalactosyldiacylglycerol biosynthesis, 18 positional d i s t r i b u t i o n i n l e a f g l y c e r o l i p i d s , 15-16,17t Monoterpene i n conifers alterations, 76 biosynthesis, 82-84 components, 77f quantitative analysis, 8 3 Monoterpene c y c l i z a t i o n , mechanism, 84-88 Mucor hiemalis, compactin hydroxylation, 110 Mucor mucedo, temperature adaptation, 332 Mycoplasma, dependence on s t e r o l s , 240 Mycosphaerella, i n f e c t i o n of papaya f r u i t s , 166 Myristic acid, structure, 4t Hyrothecium cerrucaria, studies of f a t t y acids, 223

Ν

Nannocystis exedens, s t e r o l content, 240

Nematodes function of s t e r o l s , 213-215 i n h i b i t i o n of s t e r o l metabolism, 205-208 lack of de novo s t e r o l biosynthesis, 202-203 p a r a s i t i c , s t e r o l composition, 203 Nematospiroides dubius, growth i n h i b i t i o n , 208 Neurospora crassa mutants, reversion to normal c y c l i c nucleotide l e v e l s , 335 slime mutant, s e n s i t i v i t y to propiconazole, 281 Nicotiana species, as a source of sesquiterpenoid phytoalexins, 101 Nippostronglylus b r a s i l i e n s i s , s t e r o l requirements, 202,208 Nocardia autotrophica, hydroxylation of compounds, 115 Nonhydroxylation pathway, for Pisiem sativum, 31-33f 2 8 -Nor bras s i no 1 i de b i o l o g i c a l a c t i v i t y , 60 IUPAC equivalent name, 57 28-Norbrassinone b i o l o g i c a l a c t i v i t y , 59 IUPAC equivalent name, 57

0 Octahydrophenanthrene lactones, structure, 141f Oleic acid, structure, 4t Oncopeltus fasciatus, s t e r o l conversions, 180 Oomycetes s t e r o l biosynthesis, 304-326 sterol composition, 308-309t s t e r o l occurrence, 304-318 s t e r o l requirements, 304-326 Oryza sativa, as a source of dolichosterone, 60,62 Ostertagia ostertagi, t o x i c i t y of alkylamines and amides, 205 9-0xonerolidol, structure, 95f 6-0xydendrolasin, structure, 96f

Ρ

Palmitic acid, structure, 4t Panagrellus redivivus, 203-205 ecdysteroids, 214 s t e r o l biosynthesis, 203 Pectinaceous barrier, enzymatic penetration, 172,173f Pénicillium, compactin production, Pénicillium italicum, growth i n h i b i t i o n , 279 Pepper—See Capsicum annuum


110

372


Phaseolus vulgaris castasterone content, 60,62 changes during i n f e c t i o n , 344 presence of 6-deoxocastasterone, 59-61 Phocanema decipiens, ecdysis, 214 Phosphatidylcholine, p o s i t i o n a l distribution i n leaf g l y c e r o l i p i d s , I6,17t Phosphatidylglycerol in chloroplasts, biosynthesis, 19,21t positional d i s t r i b u t i o n i n l e a f glycerolipids, I6,17t Phospholipase a c t i v i t y during i n f e c t i o n of potato leaves, 351f effect of pH, 352f from phytopathogens, 345-349 in healthy potato leaves, 349-350 on phosphatidylcholine, 347f Phytoalexins, discussion, 99-100 Phytopathogens, phospholipase a c t i v i t y , 346 Phytophagous insects, s t e r o i d metabolism, 176-185 Phytophthora cactorum growth curve, 322f metabolism of s t e r o l s , 260 micrographs, 324-325f sporulation, 295 s t e r o l occurrence, 306-309,315-321 t o x i c i t y of glycosides, 290 Phytophthora cinnamomi, growth i n h i b i t i o n , 278,280 Phytophthora infestans changes i n host ultrastructure during i n f e c t i o n , 344-345 changes i n levels of e x t r a c e l l u l a r enzyme a c t i v i t i e s during germination, 349t changes i n l i p i d composition during infection, 344-345 disintegration of zoospores, 291 host-pathogen interactions, 336-337 membrane-degrading enzymes during infection of potato leaves, 343-353 polar l i p i d composition, 345t potato resistance, 100,299 Phytophthora p a r a s i t i c a , sphingolipid content, 345 Phytosterol synthesis, e f f e c t of i n h i b i t o r s , 129-133 P i e r i s brassicae, ecdysteroids, 189 Pinus pinaster, formation of a c y c l i c hydrocarbons, 84 Pinus radiata monoterpenes, 81 seedlings, 84 Pinus virginiana, r e s i n flow from wounds, 81

Pisum sativum nonhydroxylation pathway, 31-33 pathogen, 154 Pityrosporum orbiculare, u t i l i z a t i o n of acids, 334 Pityrosporum ovale, u t i l i z a t i o n of acids, 334 Plant growth regulation by mevinolin, 109-134 by s t e r o l biosynthesis i n h i b i t o r s , 109-134 Plant l i p i d s — S e e Lipids Plant steroids antifungal a c t i v i t y , 286-301 See also Steroids Plodia interpunctella, s t e r o l metabolism, 177 Podisus maculiventris, ecdysteroid synthesis, 184 Podocarpic acid chemical synthesis scheme, 142-144,I45f structure, I 4 l f synthesis and f u n g i s t a t i c a c t i v i t y , 140-147 Podocarpic acid derivatives chemical synthesis scheme, 142-144,I45f structure, I 4 l f Podocarpus cupressins, i s o l a t i o n of podocarpic acid, 140 Podocarpus dacrydioides, i s o l a t i o n of podocarpic acid, 140 Potato—See Solanum tuberosum Potato leaves, polar l i p i d composition, 345t Pseudomonas lachrymans, i n f e c t i o n of tobacco, 101 Pseudomonas solanacearum, resistance in plant roots, 298 Pythium prolatum, sphingolipid content, 345 Pythium ultimum, release of amino acids, 291

R Raphanus sativus, c u l t i v a t i o n of seedlings, 116 Resin composition and conifer resistance, 79-81 Rhabditis maupasi, n u t r i t i o n a l requirement for s t e r o l s , 201 Rhizoctonia s o l a n i , i n f e c t i o n of tubers, 295,298 Rhizopus nigricans, inoculation of cotton tissues, 103 Rhizopus s t o l o n i f e r growth i n h i b i t i o n , 278 use of cerulenin to distinguish, 356


INDEX

373

Rhodospirillaceae, content, 244

hopanoid

S Saccharomyces cerevisiae anaerobic growth, 269 entry of protons into c e l l s , 281 growth i n h i b i t i o n , 279-280 growth response to sterols, 262t phosphate and thiamine uptake, 331-334 primary s t e r o l , 255-256 sparing a c t i v i t y of cholesterol for ergosterol, 264t s t e r o l content, 274,276 structure-function relationship of sterols, 252-265 Saccharomyces l i p o l y t i c a , f a t t y acid membrane transport, 331 Saccharomyces uvarum, f a t t y acid membrane transport, 331 Salvia o f f i c i n a l i s , use i n synthesis of monoterpene o l e f i n s , 86-87 Saponins as resistance factors, 297-300 fungitoxicity, 287-291 steroids, 292-293f Saprolegnia ferax mechanism of C-24 a l k y l a t i o n , 319f radiolabeling feeds, 316-317t Saprolegnia p a r a s i t i c a , growth i n h i b i t i o n , 337 Schizophyllum commune, transformations of compactin, 115 Scolytus v e n t r a l i s , interactions with grand f i r , 79 Septoria l i n i c o l a , growth i n h i b i t i o n , 290,295 Septoria l y c o p e r s i c i , tomatine inactivation, 297 Sesquiterpenes a l l e l o p a t h i c agents, 93-104 as phytoalexins, 93 structures, 93-98f Sesquiterpenoid stress metabolites from cotton, structure, 97f from eggplant, structure, 95f from elm, structure, 97f from potato, structure, 94f from sweet pepper, structure, 95f from sweet potato, structure, 96f from tobacco, structure, 95f Silybum marianum, c e l l suspension cultures, 1l6,126,127t S i t o s t e r o l , structure, 179f Solanum melongena, as a source of sesquiterpenoid phytoalexins, 101 Solanum s t e r o i d a l glycoalkaloids, 289f Solanum tuberosum infection by Phytophthora infestans, 336

Solanum tuberosum—Continued phytoalexin research, 100 Sordaria fimicola, growth i n h i b i t i o n , 280 Spirostane skeleton, 288f Spodoptera frugiperda, s t e r o l metabolism, 177 Staphylococcus aureus, s t e r o l synthesis, 240 Stearic acid, structure, 4t Steinernema f e l t i a e , n u t r i t i o n a l requirement f o r s t e r o l s , 201 Steroids found i n plants, major groups, 287t v a r i a b i l i t y of metabolism among phytophagous insects, 176-185 Sterols biosynthesis, 240,241f,264-265 configuration at C-20, 258,259f evidence for a dual role, 263-264 function, 256-257,318 general discussion, 7 in membranes, function, 240-242 in nematodes metabolism and function, 200-215 n u t r i t i o n a l requirement, 201-202 i n Saccharomyces cerevisiae, structure-function relationships, 252-265 inhibitors names, 270-271t structures, 272-273f isolated from commercial sources, 310-311t metabolism i n Caenorhabditis elegans, 208-213 metabolism i n f r e e - l i v i n g nematodes, 203-207 occurrence, 239-240 structural v a r i a b i l i t y , 252-255 synthesis i n h i b i t o r s , 129,130f Stigmasterol, structure, 179f Streptomyces scabies, e f f e c t of tuber alkyloids, 298 Sulfoquinovosyldiacylglycerol biosynthesis, 20-22 positional d i s t r i b u t i o n i n l e a f glycerolipids, 15-16,17t Sweet potato—See Ipomoea batatus Synecephalastrum nigricans, hydroxylation of compactin, 110

Τ

Tanacetum vulgare, c y c l i z a t i o n s of geranyl pyrophosphate, 87 Taphrina deformans growth i n h i b i t i o n , 280,281 s t e r o l i n h i b i t o r studies, 276 Teasterone, IUPAC equivalent name, 57 Tenebrio molitor, s t e r o l l e v e l s , 180 Tetrahymena, s t e r o l metabolism, 249


374


Tetrahymena pyriformis, s t e r o l metabolism, 260 Thamnidium elegans, synthesis of unsaturated compounds, 332 Thea sinensis, presence of 28-norbrassinone, 59 Tobacco—See Nicotiana species Tobacco hornworm—See Manduca sexta Tomatine effect of pH on binding to cholesterol, 294f effect on release of peroxidase from liposomes, 296t Tomato—See Lycopersicon esculentum Torulopsis glabrata depositions of c h i t i n , 278 oxidative removal of methyl groups, 269 sterol accumulation, 274 s t e r o l i n h i b i t i o n , 277t Tribolium castaneum, s t e r o l metabolism, 180 Tribolium confusum, s t e r o l metabolism, 180 Trichoderma v i r i d e , studies of fatty acids, 223 Trichophyton i n t e r d i g i t a l e , studies of fatty acids, 222 Trichophyton mentagrophytes, studies of fatty acids, 223 Trichophyton purpureum, studies of fatty acids, 222 Trichosporium, resin production i n conifers, 81 Trichosporium symbioticum, interactions with grand f i r , 80 Trichostrongylus colubriformis, i s o l a t i o n of hormones, 214 Triticum aestivum, seedling c u l t i v a t i o n , 116 Trogoderma granarium, s t e r o l metabolism, 183-184 Turbatrix a c e t i , n u t r i t i o n a l studies, 201,203-205

Typhasterol b i o l o g i c a l a c t i v i t y , 60 IUPAC equivalent name, 57

U Ulmus glabra, i s o l a t i o n of sesqui terpenes, 103 Uridinediphosphate-galactose, 18 Uromyces phaseoli, infection of bean plants, 344 Ustilago maydis s t e r o l content, 280 sterol i n h i b i t o r studies, 276 V Venturia inequalis, spore suspensions, 163 V e r t i c i l l i u m albo-atrum, inoculation of cotton tissues, 103 Vertrum steroidal alkaloids, 294f Vibrio parahaemolyticus, f a t t y acid studies, 226 W Waxes, as l i p i d s i n organisms, 7 Y Yeast general discussion, 255-256 importance of methyl groups, 261-263 Ζ

Zea mays, dwarf mutants, 35-39 Zymomonas mobilis, hopanoid content, 246,247f

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Ecology and Metabolism of Plant Lipids

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