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Subject Index Subject Index Boldface denotes illustration or figure N-acetyl-S-allylcysteine (also called in oil-macerated garlic supplements, 239 allyl mercapturic acid) platelet aggregation effect of, 270, 272 in urine following consumption of stability toward heat, 191 garlic, 81 stereochemistry of addition reactions at C=C bond, 190 carbophilic, 196, 197, 205, 223 at sulfoxide sulfur, 190, 191 thiophilic, 205 A. keratitis (Acanthamoeba keratitis), garlic ajoene (AllS(O)CH2CH=CHSSAll) and, 253 antibiotic activity, 246, 399–401 alembic, 62, 64 B. subtilis, 399 S-alk(en)ylcysteine sulfoxides, 141, 142 E. coli, 399 in alliums, amounts and kinds, 396–398 H. pylori, 249, 399 biosynthesis, 168–171 K. pneumoniae, 399 in Brassica oleracea, 170 M. phlei, 400 derivatization of, 144 M. smegmatis, 400 γ-glutamyl derivatives of, 165-171 P. aeruginosa, 399 in Leucocoryne, 172 S. aureus, 400 in mushrooms, 172 anticancer activity in Petiveria alliacea, 172 basal cell carcinoma treatment, 258, in Scorodocarpus borneensis (wood 259, 260 garlic), 172 leukemia treatment, 262 in Tulbaghia violacea (society garlic), 172 mechanism of, 262 allelopathy, 26, 299, 300 antifungal activity, 248, 319, 400, 401 allicin (AllS(O)SAll) antithrombotic activity, 190, 270, 272 ajoene from, 172 antiviral activity, 253, 254 allergy to, 288 cholesterol lowering and, 269 analysis of, discovery of, 190 by DART, 158, 159 formation from allicin, 70, 172, 191, 192 by LC-MS, from garlic and ramp, monomethyl and dimethyl analogs, 193 145–147 name, derivation of, 190 by SFC, from garlic, 165 434 Subject Index 435 antibiotic activity of, 69, 72, 244, 318, thioacrolein from, 155 319, 399–401 3-vinyl-4H-1,2-dithiin and 2-vinyl- E. coli, 244, 245, 318, 399 4H-1,3-dithiin from, 155 E. faecalis, 399 formation H. pylori, 249, 399 in A. ursinum, 136 K. pneumoniae, 399 in elephant garlic, 70 Leptotrichia buccalis, 399 enzymatic from alliin, 69, 70, 71 M. phlei, 400 rate of, 132, 135, 136 M. smegmatis, 400 self-condensation of 2-propene- Pseudomonas aeruginosa, 399 sulfenic acid, 106 Pophyromonas gingivalis, 399 targeted, using antibody-attached P. intermedia, 399 alliinase, 138 P. nigrescens, 399 by oxidation of diallyl disulfide Proteus mirablis, 400 with P450 enzymes, 79 S. aureus, 400 by oxidation of diallyl disulfide S. pyogenes, 400 with peracids, 66, 100 for antibiotic-resistant gastroenteritis, gastrointestinal mucosa, harmful 246 effects on, 259 for Gram-negative and -positive germination inhibitor, for downy bacteria, 72, 245 mildews, 319 anticancer activity hydrogen-bonding acceptor, 70 in gastric adenocarcinoma, 259 in situ generation in antitumor mechanism of, 263 therapy, 138, 261 antifungal activity of, 247, 318, 319, 400 isolation of, 66–70, 100 polybutylcyanoacrylate lifetime in vivo following injection in nanoparticles of, 247 mice, 261 synergistic activity with lead poisoning antidote, 279 amphotericin B, 247 mass spectral detection anti-inflammatory activity, 276 direct, 70, 72, 158, 159 antiparasitic activity of SFC with chemical ionization MS, 165 A. keratitis (due to Acanthamoeba microtubule-disruption by, 261 castellanii), 253 molluscicide, 318 amoebic dysentery (due to Entamoeba optical inactivity of, 135 histolytica), 252, 401 permeability, skin and membranes, Giardia lamblia, 401 73, 81, 138, 232 leishmanial strains, 401 as phytoanticipin, 300, 318 antitumor activity, 261 platelet aggregation inhibition by, 273 antiviral activity, 254 pseudo-, see 2-propenyl 2-propenethio- aroma and taste, 172 sulfonate common cold, treatment of, 254 reaction in crushed fresh garlic, 169 with cysteine, 72, 74, 272, 273 cyanide poisoning, antidote for, 278, 279 with thiamin, 73 cysteine protease inhibitor, in malaria with thiols, 72, 74, 137, 138 prevention, 253 rearrangement to thiosulfoxylate, 156 decomposition skin irritant, 291 during GC analysis, 154 stability, in water, 69, 70, 172 at room temperature, 154, 172 sulfur-sulfur bond, weakness of, 117, 173 436 Subject Index supercritical fluid extraction (SFE) of, allithiamin, 73 70, 145 allitridin, see diallyl trisulfide toxicity Allium acutangulum, 425 to rabbits, intraveneously Allium acutiflorum, 416 administered, 384 Allium altyncolicum to stored-product insect pests, 313 flavor precursor content, 396 tubulin polymerization inhibition, 261 Allium ampeloprasum, 414 alliin (S-allylcysteine sulfoxide) see also elephant garlic see also S-alk(en)ylcysteine sulfoxides, flavor precursor content, 396 143 Ulpicum of Romans, 6 activation by alliinase as aldimine, 133 Allium angulosum allicin precursor, 70, 71, 113 flavor precursor content, 396 chirality at sulfur Allium arenarium, 415 absolute configuration, 104 Allium ascalonicum, 416 significance of, 104 see also shallot content in fresh garlic, 102, 145 Allium asperum, 408 content in fresh onion, 150 Allium atropurpureum, 430 diastereomers of, 103 Allium bisculum, 15, 16 discovery of, 101, 102 Allium caeruleum, 15, 16, 17 enzymatic breakdown, rate of, 132 Allium canadense, 15 in A. sativum, 136 toxicity to animals, 289 in A. ursinum, 136 Allium carinatum, 407 in garlic supplements, 239 as weed, 12 glycoside of, 170 flavor precursor content, 396 localization in cells, 132 Allium carneum, 429 stereochemistry at sulfur, 102, 103, 104 Allium cepa, 419 synthesis of, 102 see also onion thermal stability of, 98, 99 Allium chamaemoly, 426 thiazoles from, on heating with glucose, Allium chevsuricum 99 flavor precursor content, 396 alliinase, 132–138 Allium chinense (rakkyo) activation by pyridoxal-5′-phosphate, 133 as food crop, 3, 24, 26 allergy to, 288 methiin content, 141 characterization by X-ray crystal- thiosulfinates from, cut, 141 lography, 132, 133 Allium controversum, 413 cleavage rates of alliin analogs Allium cristophii, 15, 17 by A. sativum alliinase, 136, 137 Allium descendens, 418 by A. ursinum alliinase, 136, 137 Allium fistulosum (Japanese bunching conjugated to antibody, 138 onion), 420 deactivation of, 144 as food crop, 3, 26 on immobilized support, 137 non-bulbing, 11 in garlic supplements, 239 selenium compounds in, 217, 219 localization in plants, 133 flavor precursor content, 141, 396 purification of, 104 thiosulfinates from, cut, 141 stereoselectivity with cysteine sulfoxides, Allium flavescens, 424 104 Allium flavum, 410 temperature, optimum, for activity, 137 Allium fuscum, 410 Subject Index 437 Allium giganteum, 5, 15, 17 Allium porrum, 414 pigments from, 212, 213 see also leek Allium globosum, 422 Allium praescissum, 411 flavor precursor content, 396 Allium pulchellum, 408 Allium gramineum, 15, 16 Allium ramosum, 15, 17 Allium hymenorrhizum Allium rosenbachianum, 5, 15, 17 flavor precursor content, 396 pigments from, 212, 213 Allium intermedium, 411 thiosulfinates from, cut, 141 Allium jesdianum Allium rosenorum flavor precursor content, 396 pigments from, 212, 213 Allium junceum, 11,12 Allium roseum, 429 Allium juncifolium, 12 flavor precursor content, 397 Allium karelinii Allium rotundum, 417 flavor precursor content, 396 Allium sativum, 413 Allium kermesinum, 423 see also garlic flavor precursor content, 396 Allium saxatile, 422 Allium kurrat flavor precursor content, 397 as food crop, 3 Allium schoenoprasum, 421 Allium longicuspis, 6 see also chives Allium longifolium, 15, 16 flavor precursor content, 141, 397 Allium longispathum, 412 Allium schubertii, 15 Allium macleanii Allium scorodoprasum (sand leek), 12, 415 pigments from, 212, 213 flavor precursor content, 151 Allium margaritaceum, 416 Allium sellovianum, 12 Allium moly, 15, 16, 17, 426 Allium senescens flavor precursor content, 397 flavor precursor content, 397 Allium montanum, 425 Allium sibiricum, 421 Allium moschatum, 423 Allium siculum (Nectaroscordum Allium multibulbosum, 431 siculum), 113, 114, 132 Allium neapolitanum, 15, 16, 432 flavor precursor content, 152, 397 flavor precursor content, 397 Allium spathaceum, 12 Allium nigrum, 430 Allium sphaerocephalum, 417 Allium nutans, 15, 31 flavor precursor content, 397 Allium obliquum Allium stipitatum, 214 flavor precursor content, 151, 397 flavor precursor content, 397 Allium ochroleucum, 423 2-pyridyl disulfides from, 213, 214 Allium oleraceum, 412 Allium strictum, 418 flavor precursor content, 397 Allium suaveolens, 424 Allium pallens, 409 Allium subhirsutum, 427 Allium paniculatum, 409 flavor precursor content, 397 flavor precursor content, 397 Allium tricoccum, see ramp Allium paradoxum Allium triquetrum, 15, 428 flavor precursor content, 397 as weed, 12 Allium pedemontanum, 429 flavor precursor content, 397 Allium pendulinum, 428 Allium tuberosum, see Chinese chives Allium permixtum, 427 Allium tuncelianum, 7 438 Subject Index Allium ursinum (ramson; bear’s garlic), geographic distribution, 11 305, 432 geographic origin of, determination of, 78 allelopathic effects of, 304-307 herbs and spices, 91–93 edible plant, 3, 31, 32 insect pests of, 11 elevated sulfur emissions from, 306 insect repellent, 26, 323, 324 flavor precursor content, 152, 398 invasive weeds, 18–19 growth characteristics, 12, 304-307 in Koran, 1, 34 herbal remedies involving, 231 iron absorption reduction following methyl ajoenes from, 193 consumption of, 284 platelet aggregation inhibition by, 273 metabolism of, 79 Allium victorialis (caucas), 433 names, derivation of, 1, 3 flavor precursor content, 141, 151, 152, 397 non-sulfur-containing compounds in, 223 food crop, 3 odor of, when cut, 1–3, 13, 14, 18, 19, thiosulfinates from, cut, 141 26, 75 Allium vineale (crow garlic), 415 ornamentals, 14–16, 17, 18, 212–214 flavor precursor content, 398 phytochemistry of, 12–14 toxicity
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