Index

A

Abedus herberti, 31

Acetic acid, 30

Acetylcholine, 174

Adenoregulin, 18

Agriculture

sex attractant research, 104

use of chemical signaling for pest control, 62

Aldehydes, in moth sex pheromones, 169

Algal pheromones

(a)biotic degradation, 98-99, 101

C11 biosynthesis, 95-98

C11 hydrocarbons in, 87-89, 91, 99-101

classification, 89

defensive role, 99

mass release of male gametes, 90-91

measurement, 89-92

Aliphatic acid, plant, 1

Alkaloids

in arthropod defenses, 32-34

coccinelline, 25, 26, 32-33

in insects, 25

in skin of amphibians, 18, 22-27

Alkaloids, plant, 1, 17

insect sequestration of, for defense, 119, 120-122

role in sexual selection among insects, 119, 122-130

Allelopathic compounds, 3

Allomones, 2-3

Allomyces, 133-134

Amines, amphibian skin, 18

Amphibians. See Poisons, in amphibians

Amplitude modulation, 154

Analipus japonicus, 92

Ant

communication system, 41

modulatory communication, 45-47, 49

multicomponent signaling, 43, 46-47, 48-49

nestmate recognition, 47-48

signal ritualization, 44-45

signal specificity, 44

social organization, 41

stridulatory vibration, 45-46

trail pheromones, 42-44

Apiomerus flaviventris, 129



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Chemical Ecology: The Chemistry of Biotic Interaction Index A Abedus herberti, 31 Acetic acid, 30 Acetylcholine, 174 Adenoregulin, 18 Agriculture sex attractant research, 104 use of chemical signaling for pest control, 62 Aldehydes, in moth sex pheromones, 169 Algal pheromones (a)biotic degradation, 98-99, 101 C11 biosynthesis, 95-98 C11 hydrocarbons in, 87-89, 91, 99-101 classification, 89 defensive role, 99 mass release of male gametes, 90-91 measurement, 89-92 Aliphatic acid, plant, 1 Alkaloids in arthropod defenses, 32-34 coccinelline, 25, 26, 32-33 in insects, 25 in skin of amphibians, 18, 22-27 Alkaloids, plant, 1, 17 insect sequestration of, for defense, 119, 120-122 role in sexual selection among insects, 119, 122-130 Allelopathic compounds, 3 Allomones, 2-3 Allomyces, 133-134 Amines, amphibian skin, 18 Amphibians. See Poisons, in amphibians Amplitude modulation, 154 Analipus japonicus, 92 Ant communication system, 41 modulatory communication, 45-47, 49 multicomponent signaling, 43, 46-47, 48-49 nestmate recognition, 47-48 signal ritualization, 44-45 signal specificity, 44 social organization, 41 stridulatory vibration, 45-46 trail pheromones, 42-44 Apiomerus flaviventris, 129

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Chemical Ecology: The Chemistry of Biotic Interaction Arthropods chemical defenses, 30-34 chemical eavesdropping strategies in predation, 52-54, 63 chemical predatory strategies, 62-63 chemical signaling in predation, 51-52 predatory mimicry by spiders, 59, 63 as source of frog/toad toxins, 24-26 spider venoms, 34-36 See also Lobster Atelopus toads, 18 Azabicyclononane, 33 Azamacrolides, 33, 38 Azaphenalene, 33 B Batrachotoxins actions of, 23 in amphibians, 22-23, 26, 191 in birds, 23 Beet armyworm, 55-57 Benzoyl cyanide, 30 Bioinformatics, 192 Birds, 122 chemical defenses in, 4 poisonous substance production, 17 Bolas spider, 59-61 Bombesin, amphibian skin, 18 Bombyx mori, 105 Brachycephalus toads, 18 Bradykinin, amphibian skin, 18 Bufadienolides, 18, 22, 31 Bufo toads, 18 6-(1E)-Butenyl, 92 Butylbenzene, 99 C Caerulein, amphibian skin, 18 Calcineurin, 137, 138, 139-140, 143, 187 Camouflage, in chemical signaling, 148 cAMP, 110 Campoletis sonorensis evolution, 78-80 expression patterns, 80 induced developmental arrest of host larva, 68-69 polydnavirus expression in host, 70-78 polydnavirus gene families, 79-80 polydnavirus protection for, as endoparasite, 67-68, 81 polydnavirus structure, 69-70, 82 protection from host recognition, 67-68, 81-82 Cannibalism, 128-129 Cantharidin, 129 Caprylic acid, 30 Carbon metabolism biosynthesis of C11 hydrocarbons in plants, 92-98 in plant defense, 8-9 Cassava, 58 Caudoxirene, 91 Cell death, 187 Ceratopogonid flies, 54 Chemical signaling agricultural application, 62 algal pheromones, 87-92 in ant social organization, 41 ant trail pheromones, 42-44 arthropod predation, 51-52, 62-63 camouflage, 147, 148 dispersal patterns, 148 evolutionary development of olfaction, 162-164 immunophilin / immunosuppression complexes, 136-140 lobster urine, 154-158 in marine environment, 148-150 modulatory communication in ants, 45-47, 49 molecular interaction, 142-143 multicomponent systems in ants, 43, 46-47, 48-49 multidisciplinary research, 142, 143 nestmate recognition in ants, 47-48 plant, to summon herbivore predator, 54-58, 63 predatory mimicry, 59-61

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Chemical Ecology: The Chemistry of Biotic Interaction ritualization in ants, 44-45 selection pressure in, 147 signal transduction as chemical ecology, 133-134 signal transduction in T-cells, 134 specificity of ant, 42-44 spectral contrast, 148 stridulation in ants, 45-46 temporal contrast, 148 temporospatial analysis in marine environment, 150-154, 158 types of, 161 variation in plant reaction to herbivore attack, 58 See also Sex pheromones Chilocorine, 32, 38 Chilocorus cacti, 32 Chiriquitoxin, 22 Chlorophyll, 2 CNS 2103, 34-35 Cockroach, 106, 107 Colostethus frogs, 18, 25 Combinatorial chemistry, 195-196, 197 Competition for resources, 3 human chemical defenses in, 12 Conotoxins, 73-74, 75, 80 Consumer selection pressure in chemical signaling, 147 defensive chemistry and, 3, 7 taxonomic distribution of defensive chemistry as evidence of, 3-4 vestigial accumulation in secondary compound metabolism, 7-8 Corn, 55-57, 58 Cost-benefit analysis, 9-11 Cotesia marginiventris, 55, 57 Cotton, 58 Coumarins, plant, 1 Creatonotus transiens, 129 Crotalaria spectabilis, 120, 126 Cutleria multifida, 89-90, 92, 97 Cyanogenic glycosides, plant, 1 Cycloheptadienes, 91, 99 Cyclohexene, 92 Cyclopentenes, 91 Cyclophilin, 136, 137, 138 Cyclopropanes, 91, 95 Cyclosporin, 134, 135, 137, 138, 142, 143, 187 Cysteine-rich polydnavirus expression products, 71-75, 80, 81, 82 Cytochrome b5, 109 D Danaidone, 130 Danaus gilippus, 130 Danaus plexippus, 192 Decahydroquinolines, 24, 25, 26 Defense chemistry of amphibians. See Poisons, in amphibians Defense chemistry of arthropods diversity, 30-34 sources of chemicals, 36-38 sources of steroids, 31-32 Defense chemistry of birds batrachotoxins in pitohui, 23 distribution, 4 Defense chemistry of humans characteristics, 12-13 natural sources, 13 range of, 11 synthetic sources, 11-12 Defense chemistry of insects medicinal application, 190-191 parental endowment of larva, 126-127, 129-130 sources of, 1 use of plant alkaloids, 119, 120-122 Defense chemistry of marine invertebrates distribution, 4-6 poisonous substances, 17 Defense chemistry of plants, 3 active repellent strategies, 54-55 chemical interaction vs. chemical build-up, 9 consumer selection pressure and, 7 cost-benefit analysis, 9-11 distribution, 6 human use of, 11 medicinal application, 189 poisons, 17

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Chemical Ecology: The Chemistry of Biotic Interaction signal release to summon predator during herbivore attack, 54-58, 63 theoretical models of, 6-7, 9, 13 theories of, 6-7, 9 Defensive chemistry, in general absence of, 4 allomone functions vs., 2-3 antiviral properties of toxic substances, 31 conspicuous life-style and, 4 cost-benefit analysis, 9-11 definition, 2-3 in parasitic organisms, 4 poisons and, 3 selection pressure and, 3, 7 similarities across taxa, 3, 13-14 taxonomic distribution, 3-6 theories of, 6-7, 9, 13 Degranulation, 133-134 Dendrobates frogs, 18, 23, 25 Dermorphins, amphibian skin, 18 d11-Desaturases, 108, 109-110 Desoxycorticosterone, 31 Development, individual endoparasite-induced arrest in host larva, 68-69 furanocoumarin distribution and, 2 plant volatile emissions in response to herbivore attack, 58 polydnavirus protection for endoparasitic wasps, 67 Dianthrones, 17 Dictyopteris acrostichoides, 92 Dictyopteris divaricata, 91 Dictyopteris membranaceae, 87, 91 Dictyopteris zonariodes, 91 Dictyota diemensis, 98 Dictyotene, 91, 98 Diol serenin, 133-134 Dodeca-3,6,9-trienoic acid, 93-95, 101 Dolomedes okefinokensis, 34, 38 E Ectocarpene, 89, 91, 98 biosynthesis of C11 hydrocarbons in plants, 93, 94 Ectocarpus siliculosus, 87, 91, 92, 99 Electroantennogram, 105-107 Endriandra introrsa, 97 Epibatidine, 24, 26 Epilachna varivestis, 33 Epilachnene, 33-34 Epipedobates frogs, 23, 25 Ergot, 189-190 Escherichia coli, 162 Ethanolamine, arthropod, 33-34 Euclytia flava, 53 Evolutionary processes cost-benefit analysis of defensive chemistry, 10 in host-parasite diversity, 77 insect development, 29 models of chemical defense and, 10 mutation, 193-195 olfaction in, 162-164 overdominant selection in polydnavirus expression, 74, 79-80 parasite protein structure, 79-80 segmented virus genomes in, 78-79 selection pressures in parasitization, 77-78 signal ritualization, 44-45 Exochamine, 32 F Finavarrene, 93, 94 Fireflies, 22, 31 predatory mimicry, 59 FK506/FKBPs, 134, 135, 136-137, 143, 187 peptidomimicry, 140-142 structure, 138-140 Frogs phylogenetic distribution of poisons, 18 See also Poisons, in amphibians Furanocoumarins, 2 G GABA, 174-175 Gene structure

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Chemical Ecology: The Chemistry of Biotic Interaction cysteine-rich polydnavirus expression products, 71-75, 82 FKBP12, 138 pharmaceutical research, 192-194 polydnavirus expression in parasitized wasp, 70-71 polydnavirus in Campoletis sonorensis, 69-70 polydnavirus in wasps, 69-70 random change events in secondary compound metabolism, 7-8 repeat-gene polydnavirus, 76-77 stearoyl-CoA desaturase, 109 venom-related polydnavirus expression products, 75-76 Gephyrotoxins, 26 Giffordene, 95 Giffordia mitchellae, 95-97 Glucose, plant, 8 Glucosinolates, plant, 1 Glutathione S-transferase, 79 Granulocytes, in endoparasite-induced immunosuppression, 68 Gustatory systems, 163 H Helicoverpa zea, 52-53, 110 Heliothis virescens, 68-82 Hemyda aurata, 53 (E)-2-Hexenal, 58 HF-7, 35 Histamine, amphibian skin, 18 Histrionicotoxins, 23-24, 25, 26 HIV, 184-185 HMG-CoA reductase, 190, 191 Hololena curta, 38 Homarus americanus. See Lobster Homo sapiens, 11-13 Homopumiliotoxins, 26 Hoopoe, 4 Hormosirene, 91-92 Hydrogen cyanide, 30 Hydroxydanaidal, in Utetheisa ornatrix sexual selection, 123-126, 129, 130 immunophilin / immunosuppressant complexes, 136-140 response to parasitization, 77 vertebrate, 79 I Immune system Immunosuppression hemocyte responses in parasitized host, 68 immunophilin / immunosuppressant complexes, 136-140 in parasitized host, endoparasite-induced, 68, 69, 71 T-cell signaling and, 134 Indole, 55-57 Indole alkylamines, in amphibians, 18 Indolizidines, 24 Influenza, 79 Inositol triphosphate, 112 Insects biochemical diversity, 30 diversity, 29 evolutionary development, 29 plant alarm signals for protection from, 54-58 poisonous substance production, 17 predatory mimicry by, 59-61 secondary metabolites in plants and, 2 sex attractant research, 103-105 sex pheromone detection, 111-114 sex pheromone production, 108-111 sex pheromone specificity, 107-108 as source of frog/toad toxins, 24-27 See also Defense chemistry of insects Interleukin-2, 135 Introns, in cysteine-rich polydnavirus expression products, 71, 72-73, 82 Iodosylbenzene/manganese tetraphenylporphyrin, 99-99 Ips paraconfusus, 52 Ips pini, 108 Ivermectin, 191

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Chemical Ecology: The Chemistry of Biotic Interaction K Kairomones in arthropod predation, 51, 52 definition, 161 L L-dopa, 189 Laminaria digitata, 91 Lampreys, 163 Leukotreine D4 Lima bean, 55 Linolenic acid, 93 Lipophilic alkaloids, in amphibians, 18, 22, 23 Lobster chemical signaling strategies, 150 chemical signals in dominance conflicts, 156 olfactory navigation, 151 as research subject, 150 sensory sampling behavior, 152, 158 sexual selection, 156 temporospatial analysis of chemical signaling, 150-154, 158 urine dispersal, 154-158 Lovastatin, 190 Lucibufagins, 22, 31 M Major histocompatibility complex, 134-135 Malaria, 79 Mamestra brassicae, 53 Mandelonitrile, 30 Manduca sexta, 191 antennal lobe structure/functioning for signal detection, 174-176 higher order processing of pheromonal information, 175-176 neural processing of sex-pheromonal information, 168-169 sex-pheremonal stimulus, 169-170, 172-174 sex pheromone detection, 170 sex pheromone neural pathways, 171-172 sex pheromone stimulus intermittency, 173-174 signal transduction in pheromone-specific cells, 170-171 Mantella frogs, 23-24 Marine environment, chemical signaling in, 148-150 Marine invertebrates chemical defenses, 4-6 olfactory systems, 163 poisons in, 17 Mast cell degranulation, 133 Mastigoproctus giganticus, 30 Mastophorinae spiders, 59-61 Measurement techniques brown algal pheromones, 89-90 chemical signal analysis in marine environments, 150-154 for cost-benefit analysis of defensive chemistry, 9-10 pheromone identification with electroantennogram, 105-107 7-Methylcyclooctriene, 97-98 Mevalonate, 190 Microplitis croceipes, 57 Mimicry peptidal, by FK506, 140-142, 143 predatory, 59-61 Minyobates frogs, 23 Moths, 55 parasitic wasps, 52-53, 54 predatory mimicry by spiders, 59-61 sex pheromone detection, 112, 113, 114-115, 176-177 sex pheromone production, 103, 107, 108, 109-110, 114-115 sodium sequestration, 130 See also Manduca sexta See also Utetheisa ornatrix Multifidene, 90, 91 N N-based compounds, 8-9

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Chemical Ecology: The Chemistry of Biotic Interaction NADH, 109 Neopyrochroa flabellata, 129 Nicotiana sylvestris, 191 Nitropolyzonamine, 32 Nuclear factor of activated T-cells, 135 O Octopamine, 113 Olfactory system cellular organization, 165-166 evolutionary development, 162-164 giant sphinx moth sex-pheromone system, 168-177 imaging process, 167-168, 177 neurobiological functioning, 164-165, 177 properties of odor stimuli, 166-167, 168, 177 Onychophora, 163 Opioids, 188 Ouabain, 192 Overflow metabolism, 7, 8 P Parasitization absence of defensive chemistry in parasites, 4 developmental arrest induced in host larva, 68-69 immunologic response of host, 68, 71 pheromone interception by predatory arthropods, 52-54 polydnaviruses in endoparasite protection. See Campoletis sonorensis, 81 protection strategies, 77 selection pressures in, 77-78 Peptidyl proline isomerization, 137 Periplaneta americana, 107 Perithalia caudata, 91 Pharmaceuticals antiviral properties of toxic steroids, 31 biodiversity and, 197-198 combinatorial synthesis in development of, 195-196 natural sources, 11, 135, 184 new drug development process, 183-184, 191-198 opportunities for advancement, 196-197 receptor subtype sensitivity, 186-187 selecting sources for screening for research, 188-191 selection of drug discovery targets, 184-188 specificity, 186 Phenolic amines, in frogs, 18 Pheromone biosynthesis activating neuropeptide, 110-111 Pheromones amplitude modulation, 154 ant multicomponent systems, 46-47, 48-49 ant trail, 42-44 chemical eavesdropping between arthropods, 52-54, 63 definition, 52, 161 mimetic behavior, 52 in predation between arthropods, 50-51 See also Sex pheromones Philanthus triangulum, 35 Phospholipase C, 112 Phyllobates frogs, 18, 22-23, 25, 191 Phylomedusa frogs, 18 Physaelaemin, amphibian skin, 18 Phytoecdysones, 189 Picrotoxin, 174-175 Pieris brassicae, 53 Piperidines in arthropods, 33 Pitohui bird, 4, 23 Plants allelopathic compounds in, 3 biosynthesis of C11 hydrocarbons, 92-98, 101 competition for resources in allocation of secondary chemistry, 7 insect sequestration of alkaloids from, 119, 120-122

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Chemical Ecology: The Chemistry of Biotic Interaction models of secondary metabolism, 8-9 overflow metabolism, 7, 8 predatory mimicry by, 59 screening for pharmaceutical application, 188-191 secondary metabolites in insects and, 2 sources of secondary compounds, 1 See also Defense chemistry of plants Plasmatocytes, in endoparasite-induced immunosuppression, 68 Poisons, in amphibians, 17-18, 191 in animals raised in captivity, 22 batrachotoxins, 22-23, 26 bicyclic alkaloids, 24 dendrobatid alkaloids, 23-24, 25 dietary sources, 24-27 phylogenetic distribution, 18 sources of, 18-22, 26 substances unique to frogs/toads, 24, 26 tetrodotoxins, 22 tricyclic alkaloids, 24, 25 Poisons, in general, 26 definition, 3 range of, 17 Polyamines in spider venoms, 35, 38 Polydnaviruses cysteine-rich gene family, 71-75, 80, 81, 82 in endoparasite-induced developmental arrest of host larva, 68-69 in endoparasite-induced immunosuppression, 68 in endoparasitic wasp, 67, 81 evolution, 78-80 expression products in host, 70-82 general features, 69-70 overdominant selection processes in antigen recognition site codon substitutions, 74, 79-80 repeat-gene family, 76-77, 80 segmented virus genomes and, 78-79 structure, 67 venom-related gene family, 75-76 Polyzonamine, 32 Polyzonium rosalbum, 32 Predation allomone function in, 2-3 amphibian defenses, 18 ant recruitment pheromones, 43-44 arthropod semiochemical strategies, 62-63 chemical signal interception between arthropods, 52-54 chemical signal mimicry, 59-61 chemical signaling between arthropods, 51-52 future research in chemical signaling, 61-62 plant alarm signals to summon herbivore predator, 54-58 spider venoms, 34-36 Utetheisa ornatrix defense by alkaloid sequestration, 120 Pregnanes, 32 Pseudoperga guerini, 36 Pseudophryne frogs, 24 Puffer fish, 22 Pumiliotoxins, 23, 25, 26 Pyrethroids, 17 Pyrrolidines in arthropods, 33 Pyrrolizidine alkaloids parental bestowment on eggs, 126-127, 129-130 sequestration by cannibalism in Utetheisa ornatrix, 128-129 sequestration by Utetheisa ornatrix for defense, 120 in Utetheisa ornatrix sexual selection, 123-126, 130 Utetheisa ornatrix sperm selection and, 127-128, 130 Pyrrolizidines in amphibians, 24, 25, 26-27 Q Quinolizidine, 24 R Rapamycin, 134, 135, 137, 140, 142, 143

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Chemical Ecology: The Chemistry of Biotic Interaction Ras farnesyl-protein transferase, 188 Renin, 184 S Salamanders, 18 Salmonella, 187 Samandarines, 22, 26 Saponins, 17 Sargassum asporofolium, 91 Sargassum latifolium, 91 Sauvagine, amphibian skin, 18 Schistosoma, 79 Scolytus multistriatus, 52 Scorpions, 30 Secondary compounds in cellular signal transduction, 134 consumer selection pressure and, 7 as defensive agents, 3 evolutionary processes in models of, 10 genetic mutation as source of, 7-8 metabolic characteristics, 2 models of plant metabolism, 8-9 ontogenetic distribution, 2 patterns of allocation, 2, 6-11 plant poisons, 17 in plants, 3 primary metabolism and research on, 11 sources of, 1 taxonomic distribution, 12 Senecio isatideus, 93, 95 Serine proteases, 194-195 Serotonin in amphibian skin, 18 moth sex pheromone reactivity and, 113 Sesquiterpenes, 91, 133 Sex pheromones basic function, in insects, 105, 114-115 behavioral thresholds, 113 biosynthetic enzymes, 108-110 brown algae, 87-92, 99-101 detection mechanism in moth, 170 detection by electroantennogram, 105-107 genetic determinants of response, 113-114 higher order processing in Manduca sexta, 175-176 hormonal system in production of, 110-111 interception by predatory arthropods, 52-53, 63 neural processing in moths, 168-177 peripheral detection, 111-112 plume structure, 112, 115 predatory mimicry, 59 production in insects, 108-111 research history, 103-105 signal transduction in Manduca sexta, 170-171 specificity, 107-108 stimulus characteristics, 172-173 stimulus intermittency, 173-174 Utetheisa ornatrix emission, 122-123 Utetheisa ornatrix sexual selection, 123-126, 130 visible, 103 Shigella flexneri, 187 Social regulation ant predation, 43-44 chemical signaling in ant societies, 41, 48 communication ritualization, 45 lobster chemical signals, 157, 158 nestmate recognition in ants, 47-48 Sodium sequestration, 130 Spider venoms, 34-36 Spodoptera exigua, 55 Stearoyl-CoA desaturase, 109 Steroids arthropod defense, 30-31 synthesis of steroidal pyrones, 31-32 Streptomyces avermitilis, 191 Streptomyces faecalis, 133 Streptomyces hygroscopicus, 135 Streptomyces tsukubaensis, 135

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Chemical Ecology: The Chemistry of Biotic Interaction Sulfated nucleoside glycosides, 35-36, 38 Supella longipalpa, 107 Supellapyrone, 106 T T-cells immunophilin / immunosuppression activity, 137, 143 induced immunosuppression, 134 signal transduction in, 133, 134-135 Telenomus calvus, 54 Telenomus remus, 53 Terpenes, 55-57 Tetrodotoxins mechanism, 22 in newts, 18 origin of, 22 Theophylline, 186 Tolypocladium inflatum, 135 Tomicobia tibialis, 52 Trichogramma evanescens, 53 Trichothecenes, 17 Trypanosomes, 79 Tyramine, amphibian skin, 18 U Ultraviolet light, 3 Undecane, 44 Utetheisa ornatrix cannabilism for sequestration of defensive alkaloids, 128-129 courtship behavior, 122 defensive chemistry, 119, 120-122 palatability, 120 parental endowment of eggs with alkaloidal protection, 126-127, 130 post-copulatory sperm selection, 127-128, 130 sequestration of foodplant alkaloids, 120 sex pheromone emission, in spider webs, 120 V Vespula vulgaris, 58 Viridiene, 91 Viridofungans, 188 Vitellogenin, 110 W Wasps endoparasitic, polydnaviruses in. See Campoletis sonorensis parasitoid behavior, 52-53, 54 plant signals to, during herbivore attack, 54-55, 57, 58 polydnavirus genetic complexity, 69 venom-related polydnavirus expression products, 75-76 Y Yersinia pestis, 187 Z Zaragozic acids, 188 Zetekitoxin, 22