Subject Index

A diseases of, on urinary excretion of , 454, 471, 512-514 Acetic acid biological conversion to of 17-, 454, 512-515 , 622 on mammary gland, 712, 714, 715, 21-Acetoxyallopregnane-3,20-dione, ac- 745, 757 tivity of, 598 potassium metabolism, 263 6(a)-Acetoxydesoxycorticosterone, activ- sodium metabolism, 263

ity of, 599 isolation of from, 470, 3(/3)-Acetoxy-A5-etiocholenic acid, con- 477 version to 11-desoxycorticosterone, androgens from, 470

570-572 -3(ß),ll(ß)-diol-17-one 21-Acetoxypregnane-3,20-dione, activity from, 470, 477 4 of, 598 A -androstene-3,17-dione from, 470, 21-Acetoxypregnenolone, activity of, 598 477 6(ß)-Acetoxyprogesterone, desoxycorticosterone from, 453 activity of, 440 17(0)-hydroxyprogesterone from,

partial synthesis, 438-441 470, 477 Acetylcholine, from, 453 action as neurohormone, 2 pure hormone from, 2 Achlya, hormonal control of sexual reac- lactation and, 761-767 tion in, 117, 118 masculinization due to hyperactivity Acids, of, 421 auxin action and organic, 65 relation between urinary reducing estric, see Estric acids, and under capacity and function of, 610, 611 name of individual compounds Adrenal glands, inactivation of insulin by, 309 as source of , 380, 381, 385 wound hormone activity of dicar- effect of diseases of, on urinary excre- boxylic, 79 tion of -3(A),20(OO-diol, Acrasiales, nature of aggregation stimu- 449 lus in, 118 on biological conversion of androgens Acrasin, 119 into estrogens, 398 Addison's disease, carbohydrate metabolism, 327 urinary excretion of androgens in, 508, total metabolism, 317 515 isolation of allopregnanolones from, of 17-ketosteroids in, 508, 515, 533 448 Adenine, leaf growth activity of, 99 progesterone from, 447 root-forming activity of, 37, 111 pure hormone from, 2 Adrenal cortex, relation to parathyroid glands, 278 6 as source of A -androstene-3(/3), 17(a)- Adrenalectomy, diol, 614 effect on mammary gland, 713 of pregnane-3(a), 20a-diol, 615 pituitary prolactin, 789 of A5-pregnene-3(/3),20o:-diol, 615 inhibitory effect on lactation, 762 effect of androgens on, 539 Adrenaline, SUBJECT INDEX 847

action as neurohormone, 2 17-hydroxy-ll-dehydrocorticoste- Adrenocortical extracts, rone, 563 activity of amorphous fractions of, isolation from adrenal cortex, 470, 477 592, 593 physical properties, 556 combined action of, and prolactin on Adrenotrophic hormone, of anterior pitui-

lactation following hypophysec- tary, 665-674 tomy, 768 bioassay of, 665, 666, 670 metabolism of, 602ff. composition of, 671, 687 occurrence of 17-hydroxy-ll-dehydro- effect of formaldehyde on, 673 in, 551, 552 iodine on, 673 preparation of, 550-552 ketene on, 672 Adrenocortical hormones, nitrous acid on, 672 see under Adrenocortical , and trypsin on, 673 under name of individual com- isolation from sheep pituitaries, 667,

pounds 670 Adrenocortical steroids, see also under swine pituitaries, 667

name of individual compounds physicochemieal properties, 670-672,

biological conversion to 17-ketosteroids, 686 526-534 solubility, 671 chemical structure and activity of, 562, stability, 671 563, 596-601 Aeschynomene indica, isolation of wound chemistry of, 522-601 hormone from, 79 cholesterol as precursor of, 621, 622 Ailanthus, isolation of hexenal from, 82 combined action of, and prolactin on Alanine, in insulin, 308 lactation following hypophysec- Alcohol, inactivation of insulin by acid, tomy, 756 310 configuration of, 561, 564-567, 570- Aldehydes, reaction with insulin, 311 574, 575 Alimentary tract, effect of enterogas- reduction products, 428 trone on resistance of, to ulcerative effect of ascorbic acid on the biological lesions, 229-231 conversion of cholesterol to, 622, Alkali, inactivation of insulin by, 309 623 Allatectomy, on lactation, 764-767 effect on egg development in insects,

mammary growth, 712ff., 723 140 from desoxycholic acid, 574-578 Lepidoptera larvae, 133 etiocholanic acids, 412 postembryonic development of in- lactogenic properties, 757, 758 sects, 132, 133 metabolism of, 602-623 tissue growth, 146 methods of isolation, 560 Allen-Doisy method, for assay,

oxidation of, 563 342, 344 structure of, 557-596 , urinary excretion of metabolites, 602- configuration of, 561 613, 620, 621 from corticosterone, 563 as index of adrenocortical func- structure of, 561 tion, 602, 606 Allopregnane derivatives, reactivity of Adrenosterone, functional groups, 430 activity of, 470 stereoisomerization of, 429 biological conversion of adrenal ster- Allopregnane-3 (a),20a-diol, oids to, 532 source of, 481, 619, 620 from desoxycholic acid, 589-592 Allopregnane-3 (β),20a-diol, 848 SUBJECT INDEX

source of, 619 biological conversions of, 527-529 Allopregnane-3(/3),20ß-diol, physical properties of, 553 source of, 459, 620 source of, 527, 553 , Allopregnane-3(/3), 11 (/3),21-triol-20-one, sources of, 449, 459, 460 biological conversions of, 530-532 Allopregnane-3 (β),21-diol-11,20-dione, physical properties of, 554 physical properties, 554 source of, 554 source of, 554 Allopregnane-3(I3),17A)3,,,21-triol-20-one, Allopregnane-3(a),17uo!,,-diol-20-one, metabolism, 607 metabolism of, 607 physical properties of, 554 Allopregnane-3 (β), 1Τ' β9 '-diol-20-one, source of, 554 biological conversions of, 532, 533 Allopregnan-3 (a)-ol-20-one, physical properties, 555 source of, 620 Allopregnane-3,20-dione, Allopregnan-3 (0)-ol-2O-one, configuration of reduction products, isolation from swine testis, 481 427 physical properties of, 556 conversion to progesterone, 417-419 source of, 620 source of, 620 Allopregnanolones, sources of, 448 Allopregnane-3(ß),ll(ß),17''/r7,20,21- Δ ^Allopregnene-S, 20-dione, pentol, activity of, 445 biological conversions of, 527, 528 partial synthesis of, 445 physical properties, 553 Δ 16-Allopregnene-3,20-dione, source of, 527, 553 activity of, 445 Allopregnane-3(/3),17ii/3,,,20/3,21-tetrol, from tigogenin, 411 biological conversions of, 530, 531 partial synthesis of, 445 physical properties, 554 A16-Allopregnen-3(ß)-ol-3-one, source, 554 source of, 450 Allopregnane-3(oO,ll,17<'0",21-tetrol-2O- Alloxan, diabetes mellitus due to admin- one, istration of, 321 biological conversions of, 527-529, Amino acids, 530, 531 in insulin, 308 source of, 527 leaf growth activity of, 99 Allopregnane-3 (β), 1Τ1 β ' ', 20,21-tetrol-11- root-forming activity of, 111 one, transport through plant tissue, 28 biological conversions of, 527-529 l-Aminonaphthalene-6-sulfonic acid, con- source of, 527 version to equilenin, 352 Allopregnane-3 (β), 11 (β), 17" β ' ' ,21-tetrol- Ammonium, 20-one, effect on root formation, 37 physical properties, 553 Amphibians, effect of pregneninolone on source of, 553 sexual development of, 540 Allopregnane-3 O), 16,20-triol, on, 540 source of, 450, 620 Andrena, structure of, 451 effects of parasitic castration on, 138 Allopregnane-3 (β), 17" β ' ',20 (a)-triol, Androgens, see also under name of biological conversions of, 532-533 individual compounds Allopregnane-3(0),17"/R',2O(/3)-triol, absorption from gastrointestinal tract, biological conversions of, 532-533 518 physical properties of, 555 through skin, 519 Allopregnane-SO^^'ß'^l-triol-ll^O- activators of, 493 dione, anabolism of, 519 SUBJECT INDEX 849

antagonism of estrogens to, 538 biological conversion of androstane- of, to estrogens, 539 3,17-dione to, 534-536 bioassay of, by the capon's comb A1-androstene-3,17-dione to, 534, method, 489-490 535 chicks comb method, 490, 492 Androstane-3(a),ll-diol-17-one, see 11- mammalian tests, 492, 493 Hydroxyandrosterone biochemistry of, 469-540 Androstane-3(j8), 11 (/3)-diol-17-one, biological conversion to estrogens, 397, isolation from adrenal cortex, 470 398, 525, 526 physical properties, 556 chemical determination, 494-496 3,17-, effect of bacteria on, 534-536 absorption from gastrointestinal tract, yeast on, 53Φ-536 518 effect on blood calcium in birds, 278 bacterial reduction of, 535, 536 mammary growth, 728-730 conversion to , 522-524 nipple growth, 738 enzymatic reduction of, 534, 535 in bile, 521 Androstan-3(a)-ol-17-one, see Andros- inactivation of, 534 terone international standard, 493 Androstan-3(/3)-ol-17-one, see Isoandros- isolation from adrenal cortex, 470, terone 477-481 Androstan-3 (/?)-ol-x-one, urine, 471-474 source of, 481, 620 metabolism of, 517-535 structure of, 482 mode of action, 535-538 modes of administration and biological Androstan-17(a)-ol-3-one, as metabolite of testosterone, 523 response, 518, 519 Androstanetriol, partial synthesis, 360ff. ie Polarographie determination, 493 from A -androsten-3(/3)-ol, 378 role of ovaries in mammary response , to, 729 conversion to α-, 398, 399 sources of, 2, 469-483 effect on mammary growth, 729 5 synergism with thyroxine, 538 Δ -Androstene-3 (β), 17 (a)-diol, vitamin E, 537 adrenocortical function and urinary synergistic effect of, and estrogens on excretion of, 602, 606 mammary growth, 729 as metabolite of dehydroisoandros- urinary excretion of, in Addison's terone, 524, 525, 614 disease, 508, 515 testosterone, 523 levels in men, 496-517 bacterial conversion of, 535, 537 in animals, 516 estrogenic activity of, 398 Δ3 ·5-Andr ost adien-17-on e, source of, 614 from dehydroisoandrosterone, 487, 488 A5-Androstene-3(0),17(jÖ)-diol, occurrence as artifact in urine, 487 as metabolite of dehydroisoandros- Androstane, terone in rabbits, 614 configuration of, 561 , structure of, 561 effect on mammary growth, 729 Androstane-3(a),17(a)-diol, estrogenic response to, 398 absorption from gastrointestinal tract, ΔJ-Androstene-3,17-dione, 518 enzymatic reduction of, 534, 535 biological conversion of, 521, 523 Δ4-Androstene-3,17-dione, Androstane-3(/3),17(a)-diol, absorption from gastrointestinal tract, as metabolite of testosterone, 524 518 850 SUBJECT INDEX

as metabolite of dehj'droisoandros- Δ2 or 3-Androsten-17-one, terone, 524, 526 biological conversion of testosterone testosterone, 523, 524, 526 to, 520ff biological conversion of, 521-523, 534 colorimetric determination of, 488 adrenocortical steroids to, 531, 532 from androsterone, 488 isolation from adrenal cortex, 470 occurrence as artifact in urine, 487 physical properties, 556 Androsterone, source, 532 absorption from gastrointestinal tract, Androstenetriol, configuration of, 377, 518 378 absorption spectrum, 494 from dehydroisoandrosterone, 378 antagonism of estradiol to, 538 sources of, 377 to, 538 A5-Androstene-3(i3),16,17-triol, 525 progesterone to, 538 activity of, 479 as metabolite of adrenocortical ster- adrenocortical function and urinary oids, 527-533, 535 excretion of, 602, 606 dehydroisoandrosterone, 524-526, as metabolite of dehydroisoandros- 535 terone, 479, 614 biological conversion to isoandros- conversion to 3(/?)-hydroxy-A6-etio- terone, 521 bilienic acid, 479, 480 chemical determination, 494 isolation of, 479 colorimetric determination, 496 structure, 479-481 conversion to Δ16-allopregnene-3,20- A4-Androstene-3,ll,17-trione, see Adren- dione, 445 osterone Δ2 or 3-androsten-17-one, 488 A16-Androsten-3(/3)-ol, effect on lactation, 775 conversion to androstanetriol, 378 mammary growth, 729 A4-Androsten-l l-ol-3,17-dione, pituitary prolactin levels, 789 as metabolite of 11-hydroxydehydro- from cholesterol, 476 isoandrosterone, 527 cinchol, 476 A4-Androsten-17-ol-3-one, dehydroisoandrosterone, 474 synthesis of 1-methylestradiol from, sitosterol, 476 361 stigmasterol, 476 A4-Androsten-17(a;)-ol-3-one, see Testos- intermediates in the conversion of terone testosterone to, 520-523 A5-Androsten-3(o:)-ol-17-one, isolation from urine, 471, 485, 516 as metabolite of testosterone, 523 mammogenic activity of, 789 from 11-hydroxyandrosterone, 617, 618 partial synthesis of, 475, 476 A5-Androsten-3(/3)-ol-17-one, see Dehy- structure of, 473, 485 droisoandrosterone Anethum graveolens, Δ9 or 11-Androsten-3(«)-ol-17-one, day lengths required for flowering, 84 from 11-hydroxyandrosterone, 488 Anhydrohydroxyprogesterone, see Preg- metabolism of, 488 nenin-17-ol-3-one occurrence as artifact in urine, 487 /3-m-Anisilethyl bromide, A5-, attempted synthesis of estrone from, metabolism of, 524-525 356 Δ16-Androstenols, Anorexia nervosa, from androstan-17(/3)-ol-3-one, 481, urinary excretion of 17-ketosteroids in, 482 514, 515 isolation from swine testis, 481 Anthelone, structure of, 481 effect on gastric motility, 246 SUBJECT INDEX 851

gastrojejunal ulcers, 246 Auxin protein complexes, 23, 64 occurrence in urine, 246 Auxins, see also Caulocaline, Florigen, Anthraceneacetic acid, Hormones, plant, growth, 3-Indole rate of absorption of, 28 acetic acid, Rhizocaline, etc. Antivitamin, action mechanism, 25, 44, 55-65 indoleacetic acid as, 23 antagonism between, and flower-form- Aphids, occurrence of auxin in, 24 ing plant hormone, 95ff. Apples, prevention of premature drop- antiflowering action of, 94-97 ping of, by auxin treatment, 46 as root-forming hormone, 35, 36 Arginine, in insulin, 308 assay by curvature tests, 8-15, 20, Ascorbic acid, growth activity for plants, 30, 37, 41ff., 95 107 other methods, 15 Ascorbic acid, effect of, on the biological catalytic action of, 65 conversion of cholesterol to adreno- chemical and physical requirements cortical steroids, 622 for activity, 19-21 Asparagine, and growth promotion, 19 leaf growth activity of, 99 structure and inhibitory effect, 41 root-forming activity of, 111 chemistry of, 15-26 Auxenolonic acid, concentration and activity, 44, 46, 51 identity with auxin b, 16 conditions of upward transport of, 30 Auxentriolic acid, content of legume root nodules, 52 identity with auxin a, 16 definition of, 8 Auxin a, dietary origin of, in urine, 21 activity of esters of, 20, 21 effect of gravity on formation of, 32 chemical nature of, 15 on transport of, 32 conversion to pseudoauxin a, 16 light on activity of, 32, 33 effect on root formation, 36 on synthesis of, 34 empirical formula, 15 on transport of, 28 identity with auxentriolic acid, 16 respiratory processes on transport of, interaction with indoleacetic acid, 37 30 isolation from cereal grains, 23 wounds on transport of, 35 role of, in phototropism, 33 effect on cell wall, 55-57 Auxin a lactone, cell division, 48, 49 conversion to "pseudoauxone," 16, 33 formation of fruits, 52-54 effect of carotene on photoinactivation plant respiration, 60 of, 33 root formation in cuttings, 82 structure of, 16 growth, 63 Auxin b, upstake of water, 63, 64 chemical nature of, 15 wound growth, 80 effect on buds, 39 electrical polarity of plants and trans- root formation, 36 port of, 28, 29 empirical formula, 15 extraction from roots, 48 isolation from cereal grains, 23 growth-inhibiting substances produced Auxin precursors, by, 42 inhibitory effect on growth of Avena inhibitory effect on abscission, 46 coleoptile, 24 on buds, 39-43 isolation from plant tissues, 22-24 on roots, 43-46 mode of action, 25 interaction of, 36, 37 nature of, 21-25 with biotin, 106 transport of, 22 nutrients, 37 852 SUBJECT INDEX

rhizocaline, 112 specificity of, 17 wound hormone, 48, 82 Azelaic acid, wound hormone activity of, isolation from enzyme preparations, 15 79 fungus cultures, 15 plant material, 22 Β urine, 15 of growth-inhibiting, 41 Bacillus, leaf growth activity of, 99, 100, 101 effect of allatectomy on testis of, 136 mechanism of bud inhibition by, 39-43 Bacillus mesentericus, cambium activation by, 50 inhibitory effect on estrone, 394 parthenocarpic activity, 53, 54 Bacillus putrefactus, polar transport of, 26-30 reduction of 3,17-androstanedione by, modes of application for partheno- 535, 536 carpy, 53 A4-androstene-3,17-dione by, 535, for root formation, 38 536 nature of, 23, 65 testosterone by, 535, 536 inhibitory action, 41 Bacteria, inhibiting effect on estrogens, weed-killing action, 47 394 pH and inhibitory effect on root elonga- Baeria chrysostoma, tion, 43 effect of temperature on flowering of, photoinactivation of, 32, 33 84 protoplasmic streaming and, 60, 61, 62 Bean pod test, for wound hormone relation to leptohormone, 76 activity, 76ff. special plant hormones, 57, 58 Bean pods, isolation of traumatic acid tryptophan, 22 from, 78 relative activity for parthenocarpy, 53 Benadryl, effect on gastric response to activities of, 15, 18 histamine, 242 role of, in tropisms, 30-35 Benzofuran-3-acetic acid, root formation and, 24, 38 relative auxin activity of, 18 seed germination and, 54, 55 Bile, allopregnane-3(/3),20(j3)-diol in, 449, source of, in bacterial infections of 459 plants, 24 androgens in, 521 in fungus cultures, 24 estrogens in, 384, 385, 394-396 sources, 7, 16, 17, 21-25, 96 pregnane-3(a),20(a)-diol in, 459 stimulating effect of, on cambium, 49- Bile acids, 51 conversion to adrenocortical steroids, structural requirements for activity, 574-592 19, 64 pregnane derivatives, 412-416 synthetic, 17-21 progesterone, 412-417 toxicity of, 30, 47 Bios II, transport through plants, 6, 7, 26-30, plant hormone activity of, 107 80ff. sources of, 107 Avena, effect of iodoacetate on growth Biotin, estrogenic activity and, 392 and respiration of, 59 interaction with auxin, 106 phototropism in, 6 plant hormone activity of, 102, 103, transportation of auxins through cole- 106 optile of, 28 root formation and, 37 Avena test, for auxin activity, 8-11, 20, sources of, 106 26, 28, 30, 37, 41, 43, 44, 53, 95 Bisdehydrodoisynolic acids, electrical modification of, 28 configuration of, 370 SUBJECT INDEX 853

estrogenic activity of, 364-366 prolonged estrogen treatment on, resolution of racemic, 365 291 synthesis of, 367-369 Brain, Bisdehydromarrianolic acids, as source of insect hormones, 123, 130 conversion to equilenin, 368, 370 chromatophorotrophic factor in, of isoequilenin, 368, 370 crustaceans, 163 estrogenic activity of, 364, 366 effect on metamorphosis in insects, 125, preparation of, 364 126, 127 Bisnordesoxycholic acid, endocrine activity of, 149 conversion to corticosterone, 586, 588, relationship with corpus cardiacum, 591 149 Blastokolin, Bull, androgens in urine of, 516 inhibitory effect on seedlings, 41, 44 Butenandt method, modified, isolation from sorbus fruits, 41 for estrogen assay, 341-343 Blood, levels in, 517 C bioassay of progesterone in, 346 effect of parathyroid hormone on cal- Cabbage, isolation of auxin from, 23 cium in, 261-265, 266, 269 Calciferol, effect on chlorides in, 272 effect on tetany, 286 protein concentration in, 272 mobilization of calcium in nephrecto- serum phosphorus levels, 267, 294 mized-parathyroidectomized rats on calcium in, 265 by, 269 estrogens in, 396-397 Calcium, inactivation of pancreozymin by, 219 effect of estrogen on, in blood of secretin by, 215 pigeons, 278 progestin in, 452-453 parathyroid hormone on, in blood, prolactin in, 795 261-266, 269 relation of, to color change in crus- effect on root formation, 37 taceans, 166 excretion in hyperparathyroidism, 272 Blood pressure, levels in mammals, 262 effect of parathyroid hormone on, 271 Calcium chloride, Blood serum, effect on neuromuscular transmission inactivation of cholecystokinin by, 222, after parathyroidectomy, 261 223 Calcium gluconate, secretin by, 215, 222, 223 effect on tetany, 268, 286 Blood sugar, Calcium, metabolism, effect of intestinal extracts on, 235 effect of parathyroid gland on, 256 lactation and, 757, 760 2-Bromo-4-chlorophenoxyacetic acid, parathyroid hormone on, after ne- growth activity of, and of its deriva- phrectomy, 269 tives, 44 Calliphora, Bombyx, effect of castration on corpus allatum effect of corpus allatum on accessory of, 136 sex glands of, 138 corpus allatum on accessory sex Bones, glands of, 136, 138 effect of parathyroid glands on, 268, on egg development in, 140 270, 271, 289, 290, 291 Calliphora erythrocephia, parathyroidectomy on resorption of, reproductive organs of, 135 after nephrectomy, 271, 285 Cambium, effect of auxins on, 49-51 854 SUBJECT INDEX

response to wounding, 80 conversion to dehydroisoandrosterone, Carbohydrates, 472, 473 auxin action and, 65 from dehydroisoandrosterone sulfate, Carbohydrates, metabolism, 487 effect of adrenals on, 327 isolation of, 473 anterior pituitary on, 326, 327 occurrence as artifact in urine, 487 17-ketosteroids on, 318 structure, 473 on lactation, 790, 791 Chlorophenoxyacetic acid, intermediary, 323-327 auxin activity of, and of derivatives role of insulin in, 324ff. thereof, 18, 21 Carcinogens, in biological material, 389 parthenocarpic activity of, 53 possible formation in vivo from estro- Chlorophyll, gens, 388 role of, in the formation of flower- Carotene, effect on photoinactivation of forming plant hormones, 91, 93, 94 auxin a and of its lactone, 33 Cholanthrene, Carotenoids, plant hormone activity of, carcinogenic activity of, 389 108, 109 from 3-desoxyequilenin, 388 Cartilage, epiphyseal, Cholestenone, configuration of reduction effect of growth hormone on, 676, 681 products of, 428 Castration, conversion to progesterone, 408-409 effect on corpus allatum, 136, 137 A5-Cholesten-4-one, from 2-bromocholes- secondary sex characters, 137, 138 tan-3-one, 418 urinary androgen levels, 471 structure of, 418, 419 "Castration, parasitic," Cholesterol, as precursor of adrenocorti- compared with X-ray castration, 163 cal hormones, 621ff. effect on crustaceans, 161-164 of bile acids, 621 insects, 138 biological conversion of acetic acid to, Cataract, 622 parathyroidectomy and formation of, to pregnane-3(a),20(a)-diol, 454, 261, 272, 285 455, 459 Caulocaline, conversion to androsterone, 475 role of, in bud inhibition, 115, 116 dehydroisoandrosterone, 474, 571, in stem growth, 57, 113-116 576 Cell division, hormonal control of, in 11-desoxycorticosterone, 551 plants, 76 estrogens, 398, 399 Cephalaria test, for auxins, 11 , 476 Cereal grains, nature of auxins in, 23 3 (ß)-hy droxy-A5-etiocholenic acid, Children, 576 urinary excretion of androgens in, 497- i-cholesterol, 419 500, 515 isoandrosterone, 476 of 17-ketosteroids in, 498-500, 515 , 576 Chimyl alcohol, identity with testriol, progesterone, 408-409 483 testosterone, 477 Chironomus, effects of parasitic castra- effect of ascorbic acid on the biological tion on, 138 conversion of, to adrenocortical Chlamydomonas eugametos, hormones, 622, 623 carotenoids in, 108 metabolites of, 622 5 3-Chloro-A -androsten-17-one, oxidation of, 438 activity of, 473 i-Cholesterol, from cholesterol, 419 SUBJECT INDEX 855

Cholic acid, as metabolite of cholesterol, on accessory sex glands, 136, 138 622 blood color of melanoplus, 146 conversion to progesterone, 415 color adaptation, 141, 142 Choline, development of Lepidoptera, 125 effect on estrogenic activity, 391 egg development, 139, 140 root formation and, 37 gonads, 134 Chromatophores, in crustaceans, metamorphosis, 124, 125, 127, 132 activity of, 164, 165 ovaries, 132, 134, 139 hormonal control of, 166-170 testis, 136 Chromogens, tissue growth, 146 interference of, in colorimetric estrogen mode of action of implants of, 152 assay, 335 nature of hormones in, 138ff. Chymotrypsin, relationship with reproductive organs, effect on isolation of auxin from plant 138 tissues, 22, 23 Corpus cardiacum, thyrotrophic hormone, 673 as source of insect hormones, 130, 149 Cinchol, conversion to androsterone, 476 chromatophorotrophic activity of, of cis-Cinnamic acid, cockroaches on crustacean chro- auxin activity of, 21 matophores, 178 rate of transport of, 28 effect on corpora allata, 149 trans-Cinnamic acid, insect metamorphosis, 128, 129 growth activity of, 43 physicochemical properties of chro- Cleome, effect of auxins on leaf growth of, matophorotrophic substance of, 101 154 Coconut milk, relationship between brain and, 149 plant growth activity of, 114 Corpus luteum, Colchicine, inhibitory effect on root as source of allopregnanolones, 448 elongation, 44 of pregnane-3(a),20a-diol, 615 Coleoptera, of progesterone, 347, 447, 453, 454 endocrine activity of corpus allatum effect on mammary growth, 750 in, 147 endocrine activity of, in insects, 148 influence of corpus allatum on develop- 151 ment of, 127 isolation of pure hormone from, 2 Coleus, root formation in, 112 ascorbate, 2 Colitis, therapeutic value of intestinal Corticosterone, activity of, 441, 594 extracts in ulcerative, 232 configuration of reduction products of, Complex, glandular, of insects, neuroen- 427, 428 docrine, conversion to allopregnane, 563 as source of GD hormone, 131 11-dehydroxyprogesterone, 440, 441 components of, 131 from bisnordesoxycholic acid, 586 mechanism of, 131 588, 589 Corn, indoleacetic acid in, 23 galactopoietic action of, 761 isolation of growth-inhibiting auxins isolation of, 551 from, 41 physical properties, 555 auxin precursors from, 24 source of, 560 thiamine distribution in, 104 Corticotrophin, Corpus allatum, effect on urinary excretion of cortin, as source of insect hormones, 124, 130, 610 134, 135, 146H., 149, 154 of 17-ketosteroids, 609 effect of castration on, 136 Cortilactin, 762 856 SUBJECT INDEX

effect on pigeon crop gland, 763 on sex characteristics, 160-164 Cortin, eyestalks as source of hormones, 166ff., activity of, 550, 609 188ff. effect of corticotrophin on urinary, 610 hormonal control of retinal pigment excretion of, 609, 610 movements in, 184-187 Corynebacterium mediolanum, oxidation hormones in, 159-195 4 4 of A -androstenols to A -andros- isolation of chromatophorotrophic ma- tenones by, 535, 537 terial, 166ff., 169 Cosmos, effect of adenine on leaf growth number of chromatophorotrophic hor- of, 99 mones in, 169, 173-175 Cosmos sulfureus, photoperiodic induc- retinal pigments in, 182-184 tion of flowering, 85 parasitic castration in, 161-164 Cotyledons, as source of leaf growth ovary as source of hormones in, 163 substances, 99 relation of hormones to seasonal sex Coumarane-2-acetic acid, effect on root characteristics of, 162, 163 formation, 36 response of, to removal of eyestalks, Coumarin, growth inhibitory effect of, 41 168 Cow, to removal of sinus gland, 173 effect of synthetic estrogens on mam- role of eyestalks in color change of, mary growth, 706, 707 166ff. estrogens in feces of, 396 sinus gland in, 164, 170-175 Creatine, effect of parathyroid hormone source of hormones in, 163, 164, 175ff. on excretion of, 269 X-ray castration compared with para- Creatinine, effect of parathyroid hormone sitic castration of, 163 on excretion of, 269 Cucurbits, transport of fluorescein Crocetin, source of, 108 through, 28, 29 Crocin, activity of, 108, 109 Curtis-Doisy method, for estrogen assay, Crocus, isolation of plant hormone from, 342, 344 109 Cuttings, effect of auxin on rooting of, Crop gland, of pigeon, 35-38 effect of cortilactin on, 763 Cyanide, inhibitory effect on plant prolactin on, 748, 750, 760 growth and respiration, 58 Crown gall, auxin in, 24 Cyclohexaneacetic acid, formation of, 52 auxin activity of, 19 Crustaceans, growth activity of, 17 activities of the chromatophorotrophic Cyclohexylideneacetic acid, auxin activ- hormones in, 173-175 ity of, 19 of retinal pigments in, 182-184 Cysteine, effect on gonadotrophic hor- chemical nature of pigments in, 164 mone of anterior pituitary, 641 chromatophorotrophic effect in, of reaction with lactogenic hormone, 658 corpora cardiaca extracts of in- Cystine, in insulin, 308 sects, 142, 147, 149 factor in brain of, 163 D effect of eyestalk hormone on pigmen- tary behavior of, 169 Decane-l,10-dicarboxylic acid, wound removal on growth of, 191 hormone activity of, 79 eyestalks on viability of, 192 A^Decene-ljlO-dicarboxylic acid, iden- hormones on color change in, 164- tity with traumatic acid, 78 170 A2-Decene-l,10-dicarboxylic acid, on molting, 188-192 as isomer of traumatic acid, 79 SUBJECT INDEX 857

wound hormone activity of, 79 partial synthesis of, 445 Dehydrocorticosterone, 9-Dehydroprogesterone, 439 physical properties of, 555 activity of, 445, 600 source of, 560 configuration of reduction products, yield of, 560 428 11-Dehydrocorticosterone, from 11-hydroxyprogesterone, 445 activity of, 594 16-Dehydroprogesterone, effect on lactation after adrenalectomy, activity of, 445 766, 767 configuration of reduction products, from desoxycholic acid, 551 428 etiodesoxycholic acid, 585, 586, 587 from dehydroisoandrosterone, 445 ll-Dehydro-17-hydroxy corticosterone, "Deseeded" test for auxins, 11 source of, 560 Desoxycholic acid, Dehydroisoandrosterone, conversion to adrenocortical steroids, absorption from gastrointestinal tract, 575-592 518 bisnordesoxycholic acid, 443, 444 as intermediate in the conversion of 11-dehydrocorticosterone, 551 cholesterol to estrogens, 398 3 (a), 12 (a)-dihy droxyetiocholanic metabolite of A4-androstene-3(jS), acid, 433, 434 17(a)-diol in guinea pigs, 524 nordesoxycholic acid, 413, 414 of A5-androstene-3(jS),17(a)-diol in pregnane-3, (a) 12(a)-diol-20-one, man, 524 413, 414, 415 bacterial oxidation of, 535 source of, 574 biological conversions of, 523 Desoxycorticosterone configuration, 474 activity of, 439, 444, 453, 539, 540, conversion of adrenal steroids to, 527, 594, 761 530 derivatives of, 599, 600 conversion to androsterone, 474 biological conversion to 17-ketoster- 3-chloro-A5-androsten-7-one, 472, oids, 533 473 to pregnane-3(a),20(a)-diol, 454,455, estrone, 361, 363 615, 616, 619 progesterone, 420-424 comparison with progesterone, 713 effect on mammary growth, 729 configuration of reduction products, from 3-chloro-A6-androsten-17-one, 427, 428 472, 473 effect on lactation after adrenalectomy, cholesterol, 408, 409, 474, 571, 576 764-766 A5-pregnen-3(/3)-ol-20-one, 432, 433 mammary growth, 712-714 stigmasterol, 410 after hypophysectomy, 728 isolation from urine, 471, 485, 516 pituitary prolactin levels, 788, 799 metabolism, 523, 525, 526, 535, 614 uterus, 347 synergism with estrogens, 539 from 3(j8)-acetoxy-A5-etiocholenic acid, 11-Dehydroisoandrosterone, 439 570, 571, 572 activity of, 445, 600 cholesterol, 551 from 12-hydroxyprogesterone, 445 progesterone, 436 Dehydroneoergosterol, stigmasterol, 551 partial synthesis of estrone from, 360 intermediates in the partial synthesis preparation of, 360 of, 570-572 X-Dehydronorestrone, synthesis of, 359 isolation of, 570 6-Dehydroprogesterone, metabolism, 608, 609, 615, 619 activity of, 439, 445, 599 physical properties, 556 858 SUBJECT INDEX

source of, 608 endocrine activity of corpus allatum in, synergism with estrogens, 713, 728 147 Desoxy-6-dehydrocorticosterone, of brain in, 147 activity of, 599 source of hormones in, 148 3-Desoxyequilenin, Diptera, muscoid, biological conversion to cholanthrene, ring gland as source of hormones in, 389 127, 128, 133, 147, 149 estrogenic activity of, 359 Dixippus, 124 formation in vitro, 387 effect of corpora allata on ovaries of, from equilenin, 377 135 in urine, 389 Dixippus morosus, isolation of, 359 color adaptation in, 141, 142 Detergents, effect on lactogenic hor- Doisynolic acids, mone, 660-661 estrogenic activity of, 364, 366 Dextrin, prevention of parathyroprival synthesis of, 364, 365, 369 tetany by, 264 Drosera, Diabetes mellitus, transport of amino acids through, 28 due to alloxan administration, 321 Drosophila, anterior pituitary extracts, 319 effect of corpus allatum on egg develop- etiology of, 320 ment in, 140 hypophysectomy and, 317 role of α-hydroxytryptophan in eye pancreas and, 303ff. pigment formation in, 144 therapeutic value of vitamins Β in, 323 Drosophila hydei, 129 urinary excretion of 17-ketosteroids in, effect of corpora cardiaca implants on 514 larvae of, 149 Diastase, effect on root formation, 35 Drosophila melanogaster, Diazomethane, inactivation of insulin eye color hormones of, 143, 144, 145 by, 311 source of hormones in, 150 Dibromocholestanone, Duocrine, 235 synthesis of 1-methylestrone from, Duodenin, 235 360, 362 Duodenum, 2,4-Dichlorophenoxyacetic acid, auxin enterogastrone formation in, 225 activity of, 18, 21, 43 possible occurrence of an insulin effect on flowering of pineapple, 96 synergist in, 235 toxicity of, 47 Dytiscus, use in weed-elimination, 47 effect of castration on corpora allata Dictychus monosporus, of, 137 hormonal control of sexual reaction in, corpora allata on ovaries of, 134, 117 135, 140 Dictyostelium discoideum, chemical nature of aggregation stimu- Ε lus in, 118 Diethylstilbestrol, Endosperm, effect on lactation, 775-777 auxin precursor in, 54 mammary growth, 706, 707 Enterocin, 233 growth activity for plants, 107, 108 Enterocrinin, biological assay of, 233 synergism with progesterone, 712 extraction from intestinal mucosa, 232, Diosgenin, conversion to A5,e-pregnadien- 233 3(/S)-ol-20-one, 411 Enterogastrone, 223-232 Diptera, biological assay of, 226, 227 SUBJECT INDEX 859

comparison with urogastrone, 245 conversion to bisdehydrodoisynolic effect on gastric motility, 227 acid, 364 secretion, 226 AB'7'9-estratrien-3-ol-17-one, 386 resistance of alimentary tract to estrone, 355 ulcerative lesions, 229-231 estrogenic activity of, 355 preparation of active concentrates of, of homologs of, 359 226 from bisdehydromarrianolic acid, 364 solubility, 227 equilin, 370, 371, 375 source of, 225 metabolism of, 385 stability, 227 oxidation of, 377 Enzymes, reduction of, 372, 375 auxin-inactivating, in pea plant, 17, resolution of dl-, 355 19, 53 source of, 334, 355 synthesis of, 352-355, 368 effect of proteolytic, on adrenotrophic 17-Equilenone configuration of a- and hormone, 673 /3-forms of, 359 on growth hormone, 684 estrogenic activity of dl-, 359 on isolation of auxin from plant synthesis of, 359 tissue, 22, 23 Equilin, conversion to equilenin, 370-371 on thyrotrophic hormone, 665 to estrone, 371 effect on gonadotrophic hormones, 641, 14-isoequilin A, 376 642 estrogenic activity, 367 growth activity of hydrolytic, 7, 56 metabolism, 385 inactivation of insulin by proteolytic, oxidation of, 377 309, 313 preparation of isomers of, 376 lactogenic hormone by, 660 reduction of, 372, 375 inhibitory effect of liver, on estrogens, sources of, 334, 382 389, 393-394 7,8-Equilinglycol, plant, on estrogens, 393-394 conversion to 7-keto estrone, 377 isolation of auxin from preparations from equilin, 377 of, 15 Estradiol, accuracy of bioassay of, 346 plant growth and, 59 antagonism to androsterone, 538 Ephestia kilhniella, to testosterone, 538 eye color hormones in, 142, 143, 145 colorimetric assay of, 337-339 11-Epicorticosterone, activity of, 600 conversion to doisynolic acid, 364, 365 14-Epiequilenin, effect on mammary growth, 704, 706, from isoequilin, 367, 376 707, 712 identity with d-isoequilenin, 355, 379 from dihydroequilenin, 375 Epinephrine, effect on salivary secretion, estrone, 372 244 oxidation of, 376-377 Episarsasapogenin, plant hormone activity of, 107 reduction of, 374 conversion to A16-pregnen-3(a)-ol-20- separation from estrone, 340 one, 410 sources of, 334, 337-339 3,9-Epoxypregnane-l 1,20-dione, partial synergistic effect of progesterone and, synthesis of, 581-584 on mammary growth, 728 Equilenin, a-Estradiol, configuration of, 361 absorption spectrum of, 340 estrogenic activity of, 342, 366, 367 configuration, 359, 370 from androstenediol, 398 of stereoisomers, 355 dihydroequilenin, 370 860 SUBJECT INDEX

inactivation by liver, 389, 390 estrone, 373 kidney, 389 marrianolic acid, 380 isolation of crystalline, 380 effect of configuration on activity of, isomers of, 375 377ff. metabolism of, 381-383, 394, 395, 396 on mammary growth, 703 oxidation of, 378 from estrone, 377 partial synthesis of, 361 inactivation by kidney, 389 sources of, 334, 382 liver, 389 ß-Estradiol, interconversions of, 370, 371 activity of, 342, 367, 373 isolation of crystalline, 381 as metabolite of estrone in rabbits, 614 metabolism, 381-384 conversion to isoestriol, 378, 380 occurrence in humans, 381, 382 A16-estrone, 378, 380 partial synthesis of, 377, 379 metabolism of, 381, 384 role of, in pregnancy, 385 sources of, 334 separation from estrone, 340 Estradiol benzoate, activity of β-,, 342 sources of, 334, 336-339, 382 factors affecting bioassay of, 342 glucuronide, 392 international unit of, 334 occurrence in urine, 381, 382 Estradiol dipropionate, uterus response Estrogenic lactones, as intermediates in to, 345 estrogen catabolism, 399 Estranediols, from estrone, 374, 375, 386 effect of, on pituitary, 400 sources of, 374, 385 from estrogens, 399 Estranol, from estrone, 374 Estrogen-protein complex, 396-397 A5-7'9-Estratriene-3,17(a)-diol, Estrogens, from equilenin, 375 absorption spectra, 340 A6,7'9-Estratrien-17(a)-ol, from a-dihy- activity of, 366, 367 droequilenin, 375 derivatives, 364, 366 equilenin, 375 antagonism to prolactin, 774 A5-7'9-Estratrien-3-ol-17-one, bioassay of, 345, 346 activity of, 379 chemical assay of, 334, 335 from equilenin, 386 reactivity of, 372-380 estrone, 379 chemistry of, 352-380 source of, 387 combined action of androgens and, on

Ai,3,5:io_Estratrien-3-ol-17-one see Es- mammary gland, 729 trone of desoxycorticosterone and, on Estric acids, see also under name of mammary gland, 728 individual compounds, activity of, of growth hormone and, on mam- 399 mary gland, 721 configuration of, 371 of pregneninolone and, on mammary formation in vivo, 399 gland, 712 synthesis of, 363-372 of progesterone and, on mammary Estrinase, in liver, 383, 393 gland, 728 inhibitory effect on estrogens, 389 of prolactin and, on mammary Estriol, gland, 721, 776 accuracy of bioassay of, 346 of testosterone and, on mammary activity of, 367 gland, 777 as metabolite of estrone, 400, 614 configuration of, 368, 371 colorimetric assay of, 336-339 effect of configuration on activity of, configuration, 377, 378 370ff. conversion to estric lactone, 379 nutrition on activity of, 391 SUBJECT INDEX 861

prolonged treatment with, on bones, conversion to doisynolic acid, 364, 365 291 estranediol, 386 vitamin Β on activity of, 391, 392 estriol, 377 effect on bioassay of progesterone, 346 estrogenic lactone, 379 blood calcium, 278 17-ethinylestradiol, 373 lactation, 733-778, 785, 798 isoequilenin, 379 mammary growth, 703-706, 715, isoestriol A, 379 716, 722, 724, 725, 774 marrianolic acid, 364 milk composition, 795 effect of folic acid on activity of, 392 nipple growth, 738, 739 irradiation on, 379 parathyroid, 278 on mammary growth, 703, 704, 707, pituitary prolactin levels, 785, 786, 731-733 788, 789 estrogenic activity of, 366, 367 enterohepatic circulation of, 394, 395 factors influencing bioassay of, 342 implantation into spleen, 390, 391 from dehydroisoandrosterone, 342 inactivation of, 389-395, 399 equilenin, 355 inhibitory effect on androgens, 538 equilin, 371 on progestin, 453 estriol, 373 6 interconversions of, 370, 371 A -isoequilin, 376 interrelationship between, and pitui- inactivation of, 389, 390, 394 tary mammogens in control of intermediates in the conversion of mammary growth, 726, 727 estriol to, 400 menstrual cycle and, 385 international unit, 334 metabolic conversions of androgens to isolation of, 3, 380 phenolic, 525-526 metabolism, 381-384, 394-396, 614 metabolism of, 380-400 oxidation of, 377 occurrence in mares, 381 physical properties, 556 partial synthesis from cholesterol, 360- plant hormone activity of, 107 363 Polarographie assay of, 340 from ergosterol, 360 potencies of, 342 physical assay of, 340 reduction of, 372, 374 phytochemical change of, 396 separation from estradiol, 340 possible conversion of, in vivo to car- sources, 334, 336, 337, 382, 621 cinogens, 388, 389 synergism with pregneninolone, 712 possible formation of, in vivo from progesterone, 709, 710 androgens, 397, 398 synthesis of, 355-356, 358, 360 precursors of, 397, 399 isomers of, 356-358, 360 sources of, 359, 394-399 A16-Estrone, standards, 334, 344 activity of, 378 synergism of dehydroisoandrosterone from /3-estradiol, 378, 380 with, 539 dZ-Estrone a, synthesis of, 356-358 synthesis of, 352-363 , unit of, 341 activity of, 392 Estrone, accuracy of bioassay, 345 occurrence in urine, 381, 382 activity of dl-, 356 17-Etheny lestradiol, antagonism to androsterone, 538 activity of, 374 testosterone, 538 from 17-ethinylestradiol, 374 chemical determination, 494 17-Ethinyl-A4-androsten-17-ol-3-one, see colorimetric assay, 336-339 Pr egnenin-17-ol-3-one configuration, 377 17-Ethinylestradiol, 862 SUBJECT INDEX

estrogenic activity of, 373 effect of extracts of, on heart-rate in from estrone, 373 crustaceans, 193 17-Ethinyltestosterone, see Pregnenin- on viability of crustaceans, 192 17-ol-3-one hormonal activity of, in crustaceans, Ethylene, effect on transport of auxin, 31 164 Ethylene chlorhydrin, effect on inhibited response of crustaceans to removal of, buds, 42 167, 169, 188ff, 191, 194 21-Ethylprogesterone, sinus gland as source of hormonal activity of, 446 activities of, 194 3(a),17(a)-Etiocholandediol, as metabo- lite of testosterone, 618 F bacterial conversion of testosterone to, 535, 536 Fat, inhibitory effect on gastric secretion, A4-androstenedione to, 535, 536 233ff. biological conversion of adrenocortical role of, in the formation of enterogas- steroids to, 527-529 trone, 225 from etiocholan-3(o:)-ol-17-one, 620 Fat body, of insects, metabolism, 524 endocrine activity of, 148, 151 source, 618 Feces, estrogens in, 396 3,17-Etiocholanedione, Ficin, liberation of auxin by, 23 as metabolite of testosterone, 523 Florigens, 83, 110, see also Flower-form- bacterial conversion of A4-androstene- ing " hormone" dione-3,17 to, 535, 536 Flower-forming "hormone," 83-97 Etiocholanic acids, conversion to adrenal antagonism to auxin, 95ff. cortical hormones, 412 attempted isolation of, 89 from 20-ketosteroids, 433, 434 formation of, 91, 93, 94 Etiocholan-3(ü?)-ol-ll,17-dione, as me- frost resistance and, 85 tabolite of adrenocortical steroids, leaves as receptors of, 86 528, 530, 618 relation of chlorophyll to, 91, 93, 94 Etiocholan-3(a)-ol-17-one, to photosynthesis, 91 as metabolite of adrenocortical ster- specificity of, 90, 91 oids, 527-533 transport of, 86, 88, 89, 90 dehydroisandrosterone, 535 Flowering, testosterone, 520-522 factors influencing, 84-97 bacterial conversion of testosterone to, photoperiodic induction of, 84 535, 536 Fluoreneacetic acid, effect on root forma- of A4-androstene-3,17-dione to, tion, 36 535, 536 Fluorescein, transport through cucurbits, from cholesterol, 476 28, 29 3(a),20(a)-, 432, 433 Fluoride, effect on growth and respira- 3(o0,17,20-pregnanetriol, 616 tion of plants, 58 metabolism, 524, 525, 527 Folic acid, effect on activity of estrone, occurrence in urine as artifact, 486, 487 392 Etiocholan-17 (ex)-ol-3-one, Follicle-stimulating hormone, of anterior metabolism, 523 pituitary, 643-647 Eyes, endocrine activity of, in insects, 148 activity of, 647 Eyestalks, assay of, 643-644 as source of chromatophorotrophic effect of cysteine on, 641 material, 166ff., 171 ketene on, 640 of hormones in crustaceans, 185 protein précipitants on, 641 SUBJECT INDEX 863

physicochemical properties, 647 hormones of, see Gastrointestinal hor- purification, 644-647 mones δ-Follicular hormone, identity with β- Gastroliths, effect of sinus gland on for- dihydroequilenin, 382 mation of, in crustaceans, 189, 191 Folliculin, Geotropism, effect on insects, 141 inhibitory effect of auxin on root Formaldehyde, effect on adrenocortico- elongation as explanation of, 45. 46 trophic hormone, 673 nature of, 6, 31 generation of, in periodic acid oxidation of roots, 34 of cortical metabolites, 613 Glands, pericardial, of insects, endocrine Fraxinus ornus, cambial stimulation in, activity of, 148, 151 by auxin, 80 prothoracic, of insects, endocrine activ- Frost resistance in plants, photoperiodic ity of, 127, 130, 151 stimulus and, 86 ventral, of insects, endocrine activity Fruits, effect of auxin on formation of, of, 148, 151 52-54 Globin-Insulin preparation, 314 formation of seedless, by auxin applica- Glucine, root-forming activity of, 112 tion, 53 Glucose-l-phosphate, Fungi, hormone-like substances in, 116ff. reversal of fluoride effect on plants by, isolation of auxins from, 15 58 nature of hormone-like substances in, Glucosuria, see also Diabetes mellitus 118 effect of animal food habits on occur- rence of, following pancreatec- phototropism of, 33 tomy, 304 /3-Glucuronidase, G role of, in metabolism, 457 Gastric acidity, Glutamic acid, effect of parathyroid hormone on, in effect on activity of traumatic acid, 79 dogs, 271 in insulin, 308 Gastric motility, effect of enterogastrone Glycosides, cardiac, on, 227 cortical activity of, 599, 601 Gastric secretion, effect of enterogastrone Glycotrophic hormone, of anterior pitui- on, 226, 228 tary, 761 fat on, 223ff. effect on lactation, 757 histamine on, 240 galactopoietic activity of, 761 urogastrone on, 245, 246 Goat, effect of estrogens on mammary humoral mechanism of, 237, 243 growth in the female, 706, 707 possible hormonal mechanism of, 243 Gonadotrophic hormones, of anterior Gastrin, 236-243 pituitary, see also Follicle-stimulat- relation to histamine, 242, 243 ing hormone Interstitial cell-stimu- preparation of histamine free, 241 lating hormone Gastrointestinal hormones (see also Cholecystokinin, Enterogastrone, chemical differences between the, 640- Pancreozymine, Secretin, Urogas- 643 trone), 201-246 chemistry of, 633-687 chemical nature of, 202, 211 effect of enzymes on, 641-643 concentration of, 203 on mammary growth following hypo- sources of, 203, 235ff. physectomy, 726 Gastrointestinal tract, Gonadotrophin, chorionic, effect on lacta- absorption of androgens from, 517 tion, 789, 790 864 SUBJECT INDEX

pro-estrogen formation following in- source of molting hormone in, 123 jection of, 397 Heteroauxin, Gonads, effect on metabolism, 317 identity with indoleacetic acid, 17 endocrine activity of, in insects, 148, Hexenal, isolation of, 82 151 Hexestrol, synergism with progesterone, Gravity, effect on auxin formation, 31 712 auxin transport, 32 Hibiscus, root-forming factor in leaves Growth, of, 112 effect of thyroparathyroidectomy on, Hippulin, source of, 382 289-290 Hirsutism, urinary excretion of androgens relation between respiration and, of in women with, 511, 512, 515 plants, 58-60 of 17-ketosteroids in women with, uptake of water and, of plants, 63, 511, 512, 515 64 Histamine, antagonism of urogastrone " Growth and Differentiation Hormone," to, 246 see Hormones in insects, GD hor- effect of benadryl on gastric response mone to, 242 Growth hormone, of anterior pituitary, on gastric secretion, 308 674-686 identity with vasodilatin, 240 activity of, 679ff. relation to gastrin, 242, 243 assay of, 674-676, 680, 681 Histidine, in insulin, 308 combined action of estrogens and, on Histone-insulin combination, 314 mammary gland, 721, 726 D-Homoequilenin, synthesis of, 359 composition of, 683, 684, 687 D-Homoestrone, estrogenic activity of, determination of purity, 677-679 359 effect of heat on, 684-685 partial synthesis of, 359 ketene on, 685 Honey, estrogenic activity in vertebrates, nitrous acid on, 685 140 proteolytic enzymes on, 684 Hormone, flower-forming, see Flower- urea on, 685 forming " hormone" on epiphyseal cartilage, 676, 681 Hormone, insulotropic, 235 isolation of, 677 Hormone A of fungi, effect of organic physiochemical properties, 683, 684 acids on production of, 118 solubility of, 679, 680 inactivation of, 118 Gut, hormones in, 4 isolation of, 118 Hormone Β of fungi, 118 H Hormone C of fungi, 118 Helianthus, Hormone D of fungi, 118 auxins in, 17 Hormone-like substances in fungi, 116— Helianthus annuus, 90 119 growth activity of pyridoxine for, 105 Hormone, parathyroid, see Parathyroid Helianthus tuberosus, 90 hormone auxin and growth of, 48, 49 Hormones, gastrointestinal, see Gastroin- "Hemiauxins," testinal hormones root formation and, 37 Hormones in crustaceans, 159-195 Hemiptera, endocrine activity of brain chromatophoro trophic, in, 147 activity of, 173-175 of corpus allatum in, 124, 147 chemical properties of, 182 insect hormone and molting of, 123, number of, 169, 173-175, 182 124 phylogenetic distribution of, 180 SUBJECT INDEX 865

properties of, 180 molt-inhibiting hormone, relation effect on blood sugar, 194 to chromatophorotrophins, color change, 164-170 190 heart rate, 193, 194 sinus gland as source of, 188, locomotor activities, 194 190-192 ovarian development, 194, 195 sources of, 4, 123ff., 127, 130, 131, sex characteristics, 160-165 146-154 viability, 192, 193 specificity of, 151 factors controlling secretion of, 181 tissue réponse to, 151 retinal pigment, eyestalk as source Hormones, nature of, 1, 4 of, 186, 187 plant, see also Auxins, Caulocaline, relation to chromatophorotro- Flower-forming hormones, Rhi- phic hormones, 187 zocaline, 5-119 sources of, 160,163,166ff., 171,172, carotenoids as, 108, 109 175ff., 182, 185, 186, 188, 190- effect on leaf growth, 98-101 192 plant growth, 5-74 Hormones in insects, action mechanism, definition of, 7, 8 122 nicotinic acid as, 106 corpus allatum, nature of, 138ff. pyridoxine as, 105, 106 effect on color change, 121 root-forming, source of, 35 postembryonal development, sources of, 4, 109 122-134 steroids as, 107 reproduction, 134-141 vitamins as, 102-107, 111 eye color, chemical nature of, 144 rejuvenating action of, 3 sources of, 143ff., 148 special, in plants, 57 eyestalk, effect on pigmentary wound, in plants, 76-83 behavior, 169 assay of, 76-78 GD hormone, action of, 131, 132, chemical nature of, 78-80 152 chemical structure and activity of, 79 effect on metamorphosis of muscoid diptera, 128, 129 interaction with auxins in cell divi- sion, 48 effect on molting, 130 secretion of, by wounded vegetal interaction with juvenile hor- cells, 76 mone, 133 Horse, physicochemical properties, 153 occurrence of equilenin in, 334 source of, 130, 136, 147 equilin in, 334 "gene," components of, 143-145 11-Hydroxyandrosterone, extraction of, 153 activity of, 478 mode of action, 142, 145, 153 as metabolite of adrenocortical ster- nature of, 142 oids, 527, 528, 529, 530, 617, 618 relation to kynurenine, 144, 145, conversion to Δ9θΓ n-androsten-3(o;)-ol- 154 17-one, 488, 617, 618 source of, 148, 151 isolation from urine, 478 juvenile hormone, interaction with sources, 527, 617, 618 GD hormone, 133 structure, 477, 478 mode of action, 129, 130, 132, 3 (/3)-Hydroxy-A6-bisnorcholenic acid, 133, 152 conversion to progesterone, 410, 412, source of, 130, 131, 133, 147 413 molting hormone, source of, 123 from stigmasterol, 410, 412 866 SUBJECT INDEX

3-Hydroxycholanthrene, formation in 17-Hy droxypregnanolone, vivo from equilenin, 388 as metabolite of adrenocortical ster- from estrone, 388 oids, 617 5 3(/3)-Hydroxy-A -cholenic acid, from cho- chemical properties, 617 lesterol, 408, 409 configuration, 617 17-Hydroxy corticosterone, source, 616, 617 activity of, 594, 761 11-Hydroxyprogesterone, effect on carbohydrate metabolism, 318 activity of, 441 metabolic conversion to 17-ketoster- conversion to 11-ketoprogesterone, 441 oids, 529, 530 from corticosterone, 440, 441 source of, 527, 554 12(«)-Hydroxyprogesterone, 17-Hydroxy-l 1-dehydrocorticosterone, activity of, 441 activity of, 594, 761 from desoxycholic acid, 441 conversion to adrenosterone, 563 17' ' β1 '-Hydroxyprogesterone, effect on carbohydrate metabolism, 318 activity of, 444 lactation after adrenalectomy, 766 androgen nature of, 533 from desoxycholic acid, 589-592 isolation from adrenal cortex, 470 ll-Hydroxydehydroisoandrosterone, metabolic conversion to 17-ketoster- metabolism of, 527 oids, 533 17-Hydroxy-11-desoxycorticosterone, ac- physical properties, 555 tivity of, 594 structure, 478 from dehydroisoandrosterone, 572-574 21-Hydroxyprogesterone, see Desoxy- intermediates in the partial synthesis corticosterone of, 572-574 a-Hydroxytryptophan, 748 metabolism of, 529, 530, 607 role of, in eye pigment formation in physical properties of, 554 Drosophila, 144 source of, 527, 554 7-Hydroxyestrone, Hymenoptera, endocrine activity of activity of, 377 brain in, 147 from 7-ketoestrone, 377 source of hormones in, 148 16-Hydroxyestrone, as intermediate in Hyodesoxycholic acid, the biological conversion of estrone conversion to progesterone, 415 to estriol, 400 intermediates in the conversion of, to 17-Hydroxyestrone, conversion to Δ6- progesterone, 415 isoequilin, 376 Hyoscyamus niger, 87, 91 3(/3)-Hydroxyetioallobilianic acid, effect of defoliation on flowering of, 96 conversion to 3-ketoetioallobilianic nutrients on flowering of, 94 acid, 481 Hyperglycemia, from isoandrosterone, 481 causes of, 315 3(/3)-Hydroxy-A5-etiobilienic acid, from effect on islets of Langerhans, 319 A5-androstene-3 (β), 16,17-triol, 478, Hyperparathyroidism, 480 effect on bones, 268 3(ß)-Hydroxy-A5-etiocholenic acid, from calcium excretion, 272 cholesterol, 576 phosphorus excretion, 272 A5-pregnen-3(/3)-ol-20-one, 434 in man, 268 11-Hydroxyisoandrosterone, pathogenesis of primary, 286 as metabolite of adrenocortical ster- renal damage and secondary, 287-289 oids, 527 symptoms of, 286-287 3-Hydroxy-20-methylcholanthrene, car- Hypertension, urinary excretion of 17- cinogenic activity of, 388 ketosteroids and, 512, 514 SUBJECT INDEX 867

Hyperthyroidism, effect on mammary interaction with auxin a, 37 gland, 732 naphthaleneacetic acid, 37 Hypoglycemia, causes of, 315 phenylacetic acid, 37 Hypoparathyroidism, isolation from plant material, 22 effect on mineral metabolism, 263 from Rhizopns suinus, 16 symptoms of, 261, 285 occurrence in corn, 23 Hypophysectomy, rate of transport of, 28 combined action of estrogen and pro- wound hormone activity of, 78, 80 lactin on mammary gland follow- 3-Indolebutyric acid, ing, 721 auxin activity of, 17, 18 estrogen and growth hormone on of derivatives of, 20 mammary gland following, 726 effect on root formation, 36 effect of androgens on mammary gland interaction with naphthaleneacetic following, 730 acid, 37 estrogens on mammary gland fol- parthenocarpic activity of, 53, 54 lowing, 717-719, 726, 727 rate of transport of, 28 pituitary preparations on mammary 3-Indolecarboxylic acid, gland following, 719, 726 effect on root formation, 36 placenta on mammary gland follow- growth activity of, 43 ing, 735 3-Indolepropionic acid, lactation and, 755 effect on root formation, 36 growth activity of, 48 I relative auxin activity of, 18 a-(/3-Indole)-propionic acid, Impatiens, effect of carotene on root auxin activity of, 21 formation of, 108 Indolepyruvic acid, possible interme- root formation in seedlings of, 111 diates in the conversion of trypto- Inanition, role of, in stimulation of phan to, 25 mammary growth by estrogens, 718 Inhibitory hormone, see Hormones in Incretin, 235 insects, juvenile hormone 3-Indeneacetic acid, Insects, auxin activity of, 17 chemical nature of eye color hor- effect on root formation, 36 mones in, 144-146 Indican, auxin activity of, 19 endocrine control of color reactions, in, 3-Indoleacetaldehyde, 141 conversion to indoleacetic acid, 25 of postembryonic development of, 3-Indoleacetic acid, 122-134 antiflowering action of, 95 estrogenic action in invertebrates of antivitamin activity of, 23 material derived from, 140 auxin activity of, 16, 20, 21, 30, 48, 50, phases of postembryonic development 54 of, 122, 123, 133 derivatives of, 17, 20 source of eye color hormones in, 143 conversion of tryptophan into, 24, 25 Insulin, dietary protein as source of urinary, 22 absorption rates, 314 distribution of, in higher plants, 17 acetylation of, 310 effect on flowering of pineapple, 96 administration of, 313-314 root formation, 36, 54, 112 amino acids in, 307, 308 gall-like swellings arising from, 52 assay of, 312-313 inactivation of, 17, 19, 34 azoderivatives of, 311 inhibitory effect on buds, 39 chemical structure of, 308 868 SUBJECT INDEX

activity of, 311 Intestinal extracts, effect on blood sugar, chemistry of, 306-307 235 crystalline, 305, 306, 307 intestinal motility, 232-234 effect on conversion of glucose to fat, secretion, 232-234 322 splenic contraction, 234 on lactation, 790 therapeutic value in ulcerative colitis, on metabolism, 316, 323 232 on salivary secretion, 243 Iodine, effect on adrenocorticotrophic factors controlling secretion of, 320 hormone, 673 implantation of tablets of, 314 inactivation of insulin by, 310 inactivation of, 309-311, 313 reaction with lactogenic hormone, 657, isoelectric point of, 306 658 isolation of, 2, 305 Iodoacetate, mode of action, 326, 327 effect on growth and respiration of molecular weight, 307 Neurospora, 59 possible occurrence of an antagonist of plants, 58 to, in parotid gland, 306, 307 water uptake in plants, 64 reversal of effect on plants by organic response of depancreatized animals to, acids, 58 321 normal animals to, 322 Iodocasein, administration to dairy ani- role of, in carbohydrate metabolism, mals, 770 Isoandrosterone, 324ff. as metabolite of adrenocortical ster- similarity to parathyroid hormone, 276 oids, 527, 530-533 solubility of, 307 biological conversion of, 3,17-andro- source of, 304 stanedione to, 535, 536 sulfur in, 309 testosterone to, 520-522 zinc content of crystalline, 307 conversion to 3(j8)-hydroxyetioallo- Insulin-globin combination, 314 bilianic acid, 481 Insulin-histone combination, 314 from cholesterol, 476 Insulin-protamine complex, action of, 17-Isodesoxycorticosterone, 313, 314 activity of, 601 Insulin-zinc complex, action of, 313 Isoequilenin, estrogenic activity of, 355 Intermedin, relation to crustacean hor- synthesis of, 351-354 mones, 181, 182 rf-Isoequilenin, from estrone, 379 Interstitial cell-stimulating hormone, of identity with 14-epiequilenin, 355, 379 anterior pituitary, 634-643 Z-Isoequilenin, from lumiestrone, 379 assay of, 634-636 Isoequilin, conversion to 14-epiequilenin, comparison between activity of, from 367 swine and sheep pituitaries, resp., Af,-Isoequilin, 639-640 activity of, 376 composition of, 687 conversion to estrone, 376 effect of cysteine on, 641 from 7-hydroxyestrone, 376 ketene on, 640 14-Isoequilin A, conversion to 14-epi- protein précipitants on, 641 equilenin, 376 immunological specificity of, 639 from equilin, 376 isolation of, 636, 637, 638 Isoestradiol, physicochemical properties of, 638-639, activity of, 376 681 conversion to 8-isoestrone, 376 sources of, 636 from dehydroequilin, 367, 375 SUBJECT INDEX 869

Isoestriol, l-Keto-7-methoxy-1,2,3,4-tetrahydro- activity of, 378 phenanthrene, from ^-estradiol, 378, 380 conversion to equilenin, 352, 355

16-oximinoestrone, 377 Ketone (C21H28-30O4), Isoestriol A, from estrone, 379 physical properties of, 555 8-Isoestrone, 20-Ketopregnane compounds, activity of, 376 from bile acids, 412-416 from 8-isoestradiol, 376 6-Ketoprogesterone, 9-Isopregnane, see Urane activity of, 439 17-Isoprogesterone, partial synthesis, 438-441 activity of, 445, 601 11-Ketoprogesterone, conversion to progesterone, 421, 423, partial synthesis of, 441 445 3-Ketosteroids, absorption spectrum of, 494 Islets of Langerhans, see Pancreas colorimetric determination of, 496 Polarographie determination of, 493 Κ 17-Ketosteroids, Ketene, acetylation of insulin with, 310 absorption spectrum of, 494, 495 effect on adrenocorticotrophic hor- arising from periodic acid oxidation of mone, 673 cortical metabolites, 611-613, 616 gonadotrophic hormones, 640 as metabolites of adrenocortical ster- growth hormone, 685 oids, 526-534 lactogenic hormone, 658-659 of testosterone, 520, 521 11-Ketoandrosterone, chemical determination of, 494-496 biological conversion of adrenal ster- colorimetric determination of, 496 oids to, 528 from 20-ketosteroids, 430-433 11-Ketodehydroisoandrosterone, occurrence as artifacts in urine, 486- biological conversion of adrenocortical 488 steroids to, 527 Polarographie determination of, 493 1 l-Keto-3-desoxy equilenin, source of, 607-609 from equilenin, 377 urinary excretion of, as index of source of, 387 adrenocortical function, 607 11-Ketoequilenin, from equilenin, 377 of, in Addison's disease, 508, 515, 6-Keto-a-estradiol, 533 activity of, 377 levels in animals, 516, 517 from estradiol, 376-377 in men, 496-516, 602 6-Ketoestrone, from estrone, 377 20-Ketosteroids, 7-Ketoestrone, absorption spectrum of, 495 activity of, 377 bromination of, 435-438 as intermediate in the biological con- colorimetric determination of, 496 version of estrone to estriol, 400 conversion to etiocholanic acids, 433, conversion to 7-hydroxyestrone, 377 434 from 7,8-equilinglycol, 377 degradation to 17-ketosteroids, 430-433 inactivation of, 400 oxidation of, 434-436 16-Ketoestrone, Polarographie determination of, 493 as intermediate in the biological con- Kidney bean, see Phaseolus vulgaris version of estrone to estriol, 400 Kidneys, from estrone, 377, 379 effect of parathyroid hormone on, 294 11-Ketoisoandrosterone, as metabolite of renal insufficiency on parathyroid. of adrenocortical steroids, 527 279, 284, 287-289 870 SUBJECT INDEX

inhibition of estrogens by, 389 enzymes on, 660 role of, in progesterone metabolism, heat on, 660 458 urea on, 660 Kynurenine, effect on corpus luteum, 634 relation to "gene hormones,'' 144, 145, on mammary growth, 723, 748 154 identity with prolactin, 784 role of, in eye pigment formation of isolation of, 651, 652 Drosophila, 144, 145 physicochemical properties of, 652- source of, 145 654, 686 reaction with cysteine, 658 L iodine, 657, 658 ketene, 658, 659 Laccase, inhibitory effect on estrogens, methyl alcohol, 659, 660 393 thioglycolic acid, 658 Lactation, species variations in activity of, 654, combined action of cortical extract 655 and prolactin on, following Lactones, estric, hypophysectomy, 768 activity of, 379 estrogens and prolactin on, 776 preparation of, 378, 379 effect of adrenal cortex on, 757, 761- Lactose, prevention of parathyroprival 767 tetany by, 264 androsterone on, 775 Lanthionine, isolation from insulin, 309 anterior pituitary on, 746-761 Leaf growth substances, sources of, 99ff. estrogens on, 773-775, 778 Leaves, antiflowering action of, 96 hypophysectomy on, 755-758 as receptors of photoperiodic stimulus, ovariectomy on, 774 85 parturition on, 773, 780, 783, 784 as source of auxin, 42, 96 progesterone on, 775 effect of light on growth of, 98 prolactin on, 780ff. on root formation of cuttings, 37 testosterone on, 775 flower-forming action of, 95, 96 effect on parathyroid, 279, 284 hormonal control of, 745-799 formation of thiamine in, 104, 105 initiation of, 776-778, 780-790 growth inhibitory effect of, 42 mechanism of, 746, 755, 760, 791-793, root-forming factor in, 37, 112 798 substances promoting growth of, 99- 101 relation between blood sugar and, 757, thiamine content of, 103 760 role of duct system in milk output, 745 Lemna, isolation of auxin from, 23 lobule-alveolar system in milk out- Lepidoptera, put, 745, 746 * effect of corpus allatum on develop- stimulating effect of placenta on, 755, ment of, 125 756 endocrine activity of brain in, 147 pregnant uterus on, 755 corpus allatum in, 125, 147 thyroid and, 767-773 prothoracic glands in, 147 Lactogenic hormone, of anterior pitui- source of hormones in, 148 tary, see also Prolactin, Mammogens, Leptohormone, 648-664 cell division in plants and, 76 assay of, 648-650, 781, 782, 784, 785 possible identity with auxin, 76 composition of, 655-657, 687 Leucine, in insulin, 308 effect of detergents on, 660, 661 Leucophaea, SUBJECT INDEX 871

effect of allatectomy on metamorphosis from estrone, 379 of, 132 Lycopus, inhibitory effect of indoleacetic on testis of, 136 acid on flowering of, 95 castration on corpus allatum in, 136 corpus allatum on accessory sex M glands of, 136-138 on egg development in, 140 Magnesium, inhibitory effect on root hormonal control of postembryonic formation, 37 development of, 152 Maleic acid, wound hormone activity of. Leucophaea maderae 79 effect of corpus allatum on ovaries in, Males, urinary excretion of androgens in 134 normal, 500-502, 515 source of hormones in, 150 in eunuchoid, 504-506, 515 Light, see also Photoperiodism. of 17-ketosteroids in normal, 500- effect of carotene on inactivation of 502, 515 auxin by, 33 in eunuchoid, 504-506, 515 on auxin activity, 32, 33 Mammary gland, content of roots, 46 combined action of desoxycorticoster- growth of leaves, 98 one and estrogen on, 713 protoplasmic streaming, 61, 62 of estrogens and pregneninolone on, transport of auxin, 28, 32 712 Lilac, isolation of growth-inhibiting of estrogens and progesterone on, auxin from leaves of, 41 709-712 A9'n-Lithocholenic acid, from desoxy- effect of adrenalectomy on, 713 cholic acid, 579, 580 androgens on, 728-730, 738 Lithocholic acid, anterior pituitary on, 716-730 conversion to pregnan-3(a)-ol-20-one, desoxycorticosterone on, 712, 713 415, 416 estrogens on, 703, 704, 712, 722, 774 from cholic acid, 415 lactogenic hormone on, 723 desoxycholic acid, 415 pituitary on, 703, 747 Liver, progesterone on, 708 effect of secretin on, 214, 217 prolactin on, 798 estrinase in, 389, 393 endocrine control of growth of, 695- inactivation of estrogens by, 389-392, 739, 798 394, 395, 399 lactation and development of, 791 methyltestosterone by, 534 testosterone by, 534 morphology of, 695-701 prolactin in, 795 relationship between adrenal cortex role of, in estrogen metabolism, 386 and, 712 in progesterone metabolism, 458-459 species variations in response of, to Lucilia, hormones, 713-715 effect of castration on corpus allatum Mammogen I (duct growth factor), of, 136 assay of, 720 corpus allatum on accessory sex- nature of, 721 glands of, 136 solubility of, 721 Lumiestrone, source of, 716, 720, 725 activity of, 379 unit of, 720 configuration of, 379 Mammogen II (lobule-alveolar growth conversion to lumimarrianolic acid, factor), 369, 371 assay of, 722, 723 872 SUBJECT INDEX

effect of progesterone on secretion of, 6-Methoxy-1 - vinyl- 3,4-dihydronaphtha- 722 lene, synthesis of estrone isomers nature of, 723 from, 356 source of, 71G Methyl alcohol, unit of, 722 reaction with lactogenic hormone, 659- Mares, estrogens in urine of pregnant, 381 660 pregnane derivatives in urine of A5-Methylandrostcne-3(/3), 17(a)-diol, pregnant, 447, 450 bacterial oxidation of, 535, 537 Marrian-Parkes-Mather method, for es- 2-Methyl-4-chlorophenoxyacetic acid, trogen assay, 342, 343 growth activity of, and of derivs., 44 Marrianolic acid, 20-Methylcholantlirene, activity of, 364, 366, 399 carcinogenic activity of, 388 conversion to doisynolic acids, 37 1-Methylestradiol, preparation of, 363, 364 estrogenic activity of, 361 Masculinization, due to hyperactivity of partial synthesis of, 361, 362 adrenal cortex, 471 1-Methylestrone, partial synthesis of, Megaloptera, 360, 362 hormonal control of postembryonic 2-Methyl-4-fluorophenoxyacetic acid, development of, 127 growth activity of, 44 Melandrium dioeciwm Mcthyliodide, inactivation of insulin by, effect of sex hormones on sex of, 108 311 Melanoplus, Methylnaphthalene acetate, inhibitory effect of cardiaccctomy in, 149 effect on buds, 42 castration on corpus allatum of, 136 l-Mcthylpcntene-2,3-dione, synthesis of corpus allatum on, accessory sex estrone isomer from, 356 glands of, 136, 138 17-Methylprogesterone, on blood color of, 146 activity of, 446 metabolic hormone in corpus allatum 21-Methylprogestcrone, of, 139, 140 activity of, 446 Melanoplus differential is, 126 partial synthesis of, 440, 443 effect of corpora allata on ovaries of, 17-Methyltestosterone, 439 134 activity of, 447 Menstrual cycle, estrogens and, 385 and modes of administration, 534 Metabolism, effect on mammary growth, 729 effect of adrenals on, 317 uterus, 347 hormones on, 315 inactivation of, 534 parathyroid hormone on basal, 271 4-Methylthiazole-5-acetic acid, effect on on phosphorus, 270 root formation, 36 factors controlling, 316 Microorganisms, of estrogens, 380-400 conversion of tryptophan to indole- role of insulin in phosphate, 325ff. acetic acid by, 24 Metakentrin, see Interstitial cell-stimu- Milk, lating hormone, of anterior pituitary hormonal control of composition of, Methionine, effect on estrogenic activity, 793-795 392 Mimosa pudica 6-Methoxy-l-iodonaphthalene, as inter- isolation of wound hormone from, 79 mediate in equilenin synthesis, 352 Mineral appetite, m- M e t ho χ y pli e n y 1 a c e t i c a cid, effect of nephrectomy on, 293 synthesis of doisynolic acid from, 365- parathyroidectomy on, 272, 292-293 366 Mineral intake, SUBJECT INDEX 873

effect on activity of parathyroid, 279 Naphthalene-l-nitro-(aci)-methane, Mineral metabolism, auxin action of, 20 effect of adrenal cortex on, 263 Naphthoxyacetic acid, parathyroid glands on, 257, 263, 266 effect of, and its derivatives on root Molting, formation, 36 effect of hormones on, in crustaceans, parthenocarpic activity of a-, 53 188-192 Naphthylacetamide, effect on root forma- in insects, 123ff., 130 tion, 36 Monkey, androgens in urine of, 516, 517 Naphthylmethylsulfonic acid, 17-ketosteroids in urine of, 516, 517 effect on root formation, 36 Monodehydrodoisynolic acid, structure 1-Naphthylnitromethane, of, 367 auxin activity of, 19 synthesis of, 369 Neoergosterol, Mucor mucedo, hormonal control of preparation of, 360 sexual reactions in, 117 estrone isomer from, 360, 361, 362 Mucosa, gastric, 235-243 structure of, 360 attempted isolation of active prin- Neopregnenolone, conversion to neopro- ciple from, 240 gesterone, 422, 424 secretin in, 235 from dehydroisoandrosterone, 422, 424 intestinal, 203ff., structure of, 424 as source of gastrointestinal hor- Neoprogesterone, mones, 203, 206, 218, 220, 225 activity of, 445, 446 isolation of pancreozymin from, from neopregnenolone, 422, 424 218 structure of, 424 Muscle, effect of insulin on glycogen Nephrectomy, formation in, 322, 323 effect of parathyroidectomy on bone parathyroid hormone on contrac- resorption following, 271 tion of, in isolated frog leg, 277 on mineral appetite, 293 parathyroid hormone and, 269, 270 Ν Nephritis, effect of parathyroid hormone on, 271 Nails, Nervous system, effect of hypoparathyroidism on, 261 effect on lactation, 798 1-Naphthaleneacetamide, central,'as source of chromatophoro- auxin activity of, 20 trophic hormones in crustaceans, Naphthaleneacetic acid, 175-180 effect on flowering of pineapple, 96 endocrine activity of neurosecre- gall-like swellings arising from, and its tory cells, 123, 149 derivatives, 52 number of chromatophorotrophins growth activity of, 48 in, of crustaceans, 179, 180 inhibitory effect on buds, 40 Neurohormones, 2 interaction with indoleacetic acid, 37 Neurospora, effect of iodoacetate on with indolebutyric acid, 37 growth and respiration of, 59 rate of transport of, 28 Nicotinic acid, 1-Naphthaleneacetic acid, distribution in plants, 106 auxin activity of, 17, 18, 20 effect on root formation, 37 a-Naphthaleneacetic acid, plant hormone activity of, 106 effect on root formation, 36 transport through plants, 106 Naphthaleneacetonitrile, Nitrates, auxin activity of, 20 effect on root formation, 37 874 SUBJECT INDEX

Nitrous acid, effect on adrenocortico- sources of, 335-339 trophic hormone, 673 Ovariectomy, on growth hormone, 685 effect of mammogen II on mammary inactivation of insulin by, 311 growth following, 722 5-Nonanol-l,9-dicarboxylic acid, wound lactation and, 774 hormone activity of, 79 urinary excretion of androgens and, 5-Nonanone-l,9-dicarboxylic acid, wound 506-508, 511, 512, 515 hormone activity of, 79 17-ketosteroids and, 506-508, 511, A^Nonene-l^-dicarboxylic acid, 512, 515, 533 wound hormone activity of, 79 Ovaries, as source of allopregnanediols, A2-Nonene-l,9-dicarboxylic acid, 619 wound hormone activity of, 79 of androgens, 398, 470 Nordesoxycholic acid, from deoxycholic estrogens, 2, 380, 381, 385, 397 acid, 413 pregnanediol, 619 10-Nordesoxy corticosterone, progesterone, 347 activity of, 599 effect of corpus allatum on, of insects, a-Norequilenin, 134 estrogenic activity of, 359 removal of, on urinary excretion of synthesis of, 359 androgens, 506-508, 10-Norprogesterone, activity of, 439, 599 511, 512, 515 20- Nor progesteron e, 17-ketosteroids, 506-508, activity of, 446 511, 512, 515, 533 partial synthesis of, 446 on mammary response to androgens, Nyctoperiod, 89 729 isolation of estrogen from, 2 Ο role in mammary growth, 736 16-Oximinoestrone, Oat seedlings, isolation of pure hormone conversion to isoestriol A, 377 from, 2 preparation of, 377 A1'7-Octadiene-l,8-dicarboxylic acid, wound hormone activity of, 79 Ρ A^Octene-ljS-dicarboxylic acid, wound hormone activity of, 79 Palmitic acid, activating action on Orthoptera, androgens, 493 effect of fat body on egg maturation Pancreas, diabetes mellitus and, 303 in, 135 effect of alloxan on islets of, 321 endocrine activity of corpus allatum hyperglycemia on islets of, 319 in, 124, 125, 147 pancreozymin on, 220 of corpus cardiacum in, 147 secretin on, 203ff., 213 source of hormones in, 148 on lactation, 790 Ovarian hormones, (see also Estrogens endocrine function of, 318-327 and under name of individual com- enzyme production by, 218 pounds) factors influencing insulin content of, assay of, 333-347 318ff. effect of anterior pituitar}' on mammo- histology of islets of Langerhans, 304 genic activity of, 735 hormonal stimulation of secretion of, on lactation, 733-780 205 uterus, 708 internal secretion, 301-327 role of, in lactogenic response to pitui- islets of Langerhans as source of tary extracts, 750, 751 insulin, 304 SUBJECT INDEX 875

isolation of insulin from, 2, 305 mineral metabolism and, 257, 266, 279- use of secretin in the differential 282 diagnosis of diseases of the, 216, relation to adrenals, 278 217 Parathyroid hormone, zinc content of human, 307 absorption spectrum, 274 Pancreatectomy, assay of, 276, 277, 294 animal food habits and occurrence of bone cell theory of action of, 270 glycosuria following, 304 composition of, 275 effect on lactation, 790, 791 demineralization of bones due to Pancreozymin, 217-220 overdosage of, 268 assay of, 218, 219 diuretic action of, 271 clinical application of, 219 effect on basal metabolism, 271 demonstration of, in secretin concen- blood calcium, 265, 266 trate, 217 phosphorus levels, 267, 294 effect on composition of pancreatic pressure, 271 juice, 217 protein concentration, 272 on pancreas, 220 calcium metabolism after nephrec- enzymic inactivation of, 219 tomy, 269 hormonal nature of, 218 excretion of radioactive phosphorus, preparation of concentrates, 218 267, 294 solubility of, 219 gastric juice in dogs, 271 source of, 218 nephritis, 271 stability of, 219 urinary phosphorus excretion, 266 Pantothenic acid, extraction of, 272 fatal effect of overdosage of, in dogs, distribution in plants, 106 267-268 effect on estrogenic activity, 391 inactivation, 273-275 plant hormone activity of, 106 isolation of, 256, 294 sources of, 106 mode of action, 269 transport through plants, 106 physiological activity, 276 Parathyroid glands, protein nature of, 273, 274 accessory, 258, 259 purification of, 272-273, 294 anatomy of human, 257, 258 relation to pituitary, 277, 278 of animal, 258 thyroid, 278 bone cell theory of activity of, 270 sex differences in weight of, 278 chemical control of activity of, 279ff. similarity to insulin, 276 effect of estrogens on, 278 solubility of, 275 lactation on, 279, 284 species differences in response of skele- mineral intake on, 279-282 tal tissue to, 290 pregnancy on, 279, 282-284 stability of, 274 rickets on, 279 unit of, 276 testosterone on, 278 yield of, 276 on calcium metabolism, 256, 264 Parathyroidectomy, creatine excretion, 269 cataract formation following, 261, 272 mineral metabolism, 257 dietary requirements following, 259 phosphate excretion, 269, 270 effect of calcium chloride on neuro- embryology of, 257 muscular transmission after, 261 endocrine nature of, 256, 265 on blood calcium level, 284 histology of, 257 on fertility in rats, 284 hormone of, see Parathyroid hormone, mineral appetite, 292, 293 876 SUBJECT INDEX

nails, 261 Phosphates, metabolism, role of insulin skin, 261 in, 325ff. teeth, 291-292 Phosphorus, urinary phosphorus excretion, 263 effect of parathyroid hormone on effects of, 259-265 metabolism of, 263, 266, 267, 270, neuromuscular symptoms after, 260, 294 261 thyroparathyroidectomy on urinary survival rate, 259 excretion of radioactive, 267 tetany and, 262, 263, 264 Photoinactivation, see also Light Parthenocarpy, 771 carotene and, of auxin, 32, 33 auxins and, 53, 54 of indoleacetic acid, 34 Parturition, effect on lactation, 773 Photoperiodism, 84ff. Pea plants, auxin-inactivating enzyme Phototropism, 6, 26, 32-34 in, 17, 19, 53 detection in seedlings, 26 Peas, leaf growth substances from diffu- in fungi, 33 sâtes of, 99, 100 nature of, 6 Pepsin, Phycomyces, indoleacetic acid in, 33 effect on adrenotrophic hormone, 673 Phycomyces blakesleeanus, growth hormone, 684 effect of histamine on, 117 thyrotrophic hormone, 665 thiamine on, 103, 117 inactivation of insulin by, 313 hormonal control of sexual reactions lactogenic hormone by, 660 in, 117 Perilla nankinensis, 87, 88 Phytohormones, Perilla ocymoides, 88 definition, 8 Peristaltin, 233 Phytomonas tumefaciens, Phalaris, phototropism in, 6 auxin content of galls arising from, 52 Phaseolus, transport of auxin through Picrocrocin, hormone activity of, 109 seedlings of, 32 Pigments, chemical nature of, in crus- Phaseolus vulgaris, taceans, 164ff. hormones from, 76 Pineapple, effect of auxins on flowering substances promoting root formation of, 96 in, 111 Piperidine, reaction with insulin, 311 Phenoxyacetic acid, Pisum, auxin activity of, 21 auxins in, 17 effect of, and its derivatives on root indoleacetaldehyde in, 25 formation, 36 Pitocin, effect on lactation, 792 Phenylacetic acid, Pituitary, anterior, effect on root formation, 36 activities of extracts of, 758-760 interaction with indoleacetic acid, 37 administration of extracts of, to mobilization of rhizocaline by, 113 dairy animals, 752-755, 758 relative auxin activity of, 18 effect of extracts of, on lactation, 756 Phenylalanine, on mammary gland, 747 conversion to tyrosine in vitro, 388 milk fat, 794 in insulin, 308 ovaries, 633 Phenylbutyric acid, 25 testis, 633 growth activity of, 18 effect on carbohydrate metabolism, relative auxin activity of, 18 326, 757 Phenylisocyanate, reaction with insulin, lactation, 746-761, 781, 782 311 mammary gland, 703, 716-730 SUBJECT INDEX 877

mammogenic activity of ovarian estrogens, 380, 381, 385 hormones, 735 , 615, 619 metabolism, 316, 317 progestin, 453 galactopoietic activity of extracts of, progesterone, 347 788 prolactin, 795 hormones, chemistry of, 631-693 (see effect on lactation, 755, 756 also under name of individual mammary growth, 734-736 hormones) Plant, growth hormones, see Hormones, insulotrophic principle in, 320 plant growth interrelationship between estrogens tissues, extraction of auxins from, 22 and hormones of, in control of Plants, mammary growth, 726, 727 as source of estrogen-inactivating lactogenic properties of extracts of, 750 enzymes, 393, 394 luteotrophic activity of extracts of, auxin and wound growth in, 80 797, 798 produced in bacterial infections of, mammogenic activity of, 724 24, 52 protein nature of hormones of, 686 distribution of pantothenic acid in, 106 relation between ovarian hormones pyridoxine in, 105 and mammogens of, 718ff. thiamine in, 103 role of ovarian hormones in lactogenic effect of auxin on respiration of, 60 response to extracts of, 750, 751 defoliation on flowering of, 96 species variations in lactogenic re- enzymes on growth of, 59 sponse to, 751 iodoacetate on water uptake, 164 Pituitary gland, as possible source of sugars on water uptake, 64 estrogens, 385 electrical polarity and transport of effect of estrogenic lactones on, 400 auxin through, 28-30 estrogens on prolactin content of, factors involved in stem growth of, 783 114ff. irradiated estrone on, 379 hormonal control of cell division in, 76 eosinophilic cells of, as source of hormone excretion in injured, 76 prolactin, 795 inhibitory effect of auxin on flowering mammogen I in, of cattle, 725 of, 94-97 mammogenic activity of, 713, 727 isolation of auxins from, 22, 23 relation to parathyroid, 277, 278 "laziness" of, 31, 34 to thyroid, 661 long-day, 84, 85 role of, in mammary response to mechanism of auxin transport through, androgens, 730 26-30 in nipple growth, 738 physiology of wound growth in, 80 urinary excretion of androgens in reaction to wounding, 76-82 diseases of, 509, 575 relation between growth and respira- of 17-ketosteroids in diseases of, tion in, 58-60 509, 575 and salt uptake in, 64 Pituitary, posterior, effect on lactation, and water uptake in, 63-65 791-793, 798 role of thiamine in, 105 isolation of pure hormone from, 2 short-day, 84, 85 Pituitrin, effect on salivary secretion, transport of amino acids through, 28, 243, 244 29 Placenta, as endocrine organ, 736 pantothenic acid through, 106 as source of allopregnanediols, 619 pyridoxine through, 106 androgens, 471 thiamine through, 104 878 SUBJECT INDEX

tropisms in, 6, 26, 32-34 Pregnane-3(a),6(/3)-diol-20-one, from hyo- Poa alpina, 822 desoxycholic acid, 415 growth activity of estrone for, 107 Pregnane-3(a),12(a)-diol-20-one, from Pollen, bud inhibition by, 39 desoxycholic acid, 413-415 isolation of auxin from, 52 Pregnane-3(a),17-diol-20-one, see 17-Hy- Populus balsamifera, droxypregnanolone effect of wounding on, 81 Pregnane-3(<*),17-diol-20-one, adrenocor- Potassium, metabolism, tical function and urinary excretion effect of adrenal cortex on, 263 of, 602, 606 Potato, dormancy of, 41 3,20-Pregnanedione, configuration of re- A5,11-Pregnadien-3(ß)-ol-20-one from de- duction products, 427 hydroisoandrosterone, 420, 421, 423 sources of, 448, 620 from diosgenin, 411 3(a), 11,20-Pregnanetriol A, see Urane- Pregnancy, colorimetric assay of estrone triol in the diagnosis of, 336, 338 Pregnanetriol B, see, 3(a), 16,20-Allopreg- effect on lactation, 780, 783, 784, 787, nanetriol 3(/?),16,20-Pregnanetriol, 789, 790 conversion to 3(û;),20(a)-pregnanediol, parathyroid, 279, 282 411, 412 production of estrogens, 396 from sarsasapogenin, 411 urinary excretion of adrenocortical 3 (α), 17,20-Pregnanetriol, metabolites, 619 configuration of, 616 of androgens, 514 conversion to etiocholan-3(a)-ol-17- of estrogens, 380ff. one, 432, 433, 616 of 17-ketosteroids, 514 from 3(a),20(o:)-pregnanediol, 431, 432 role of estriol in, 385 source of, 616 Pregnane derivatives, urinary excretion of, and adrenocorti- configuration of reduction products, cal function, 602, 606 427-429 3(a)-Pregnanol, source of, 620 from bile acids, 418 Pregnanols, sources of, 449 progesterone, 425ff. Pregnan-6(j3)-ol-3,20-dione, sapogenins, 418 conversion to progesterone, 415 reactivity of functional groups in, 430 from hyodesoxycholic acid, 415 sources of, 418 Pregnan-3 (a)-ol-20-one, stereoisomerization of, 429 configuration of reduction products, 3 (a) ,20 (a)-Pregnanediol, 427, 429 as metabolite of cholesterol, 622 from lithocholic acid, 415, 416 desoxycorticosterone, 615, 616, 619 glucuronide of, 456, 457 progesterone, 603, 615, 619 source of, 620 conversion to progesterone, 416 , source of, 335 from 3(/3),16,20-pregnanetriol, 411, 412 A5-Pregnene-3(/3),20a-diol, metabolic precursors of, 454, 455 source of, 615 sources of, 335, 449, 453, 454, 457, 481, A5-Pregnene-3(/3),20a;-diol, urinary excre- 615 tion of, as indication of adrenocorti- synergism with progesterone, 347 cal function, 602, 606 urinary excretion of, as indication of A4-Pregnene-17(0),2O(«)-diol, metabolic adrenocortical function, 602, 606 conversion to 17-ketosteroids, 533 3(a),20(a)-, 455 A4-Pregnene-ll(/3),21-diol-3,20-dione, see partial synthesis of, 456 Corticosterone structure of, 452, 456 A4-Pregnene-17' ' β1 ' ,2 l-diol-3,20-dione, SUBJECT INDEX 879

physical properties, 554 sources of, 448 source, 554 A4-Pregnen-20(a)-ol-3-one, from A5-preg- 4 A -Pregnene-20,2 l-diol-3,11-dione, nen-3(/3),20(a)-diol, 438 physical properties, 554 A5-Pregnen-3(/3)-ol-20-one, source, 554 as metabolic precursor of progesterone, 5 A -Pregnene-3G3),17"/3"-diol-20-one, 459 configuration, 602-603 configuration of reduction products, isolation of, 602 429 source of, 603 conversion to 6(ß)-acetoxyprogester- urinary excretion of, in cancer of one, 438-441 adrenals, 602, 606 allopregnanediols, 426 4 A -Pregnene-20,21-diol-3-one, allopreganolones, 426 activity of, 601 dehydroisoandrosterone, 432, 433 4 A -Pregnene-17 (ß), 21-diol-3,11,20-trione, 3 (/3)-hydroxy-A5-etiocholenic acid, see 17-Hydroxy-ll-dehydrocorti- 434 costerone 6-ketoprogesterone, 438, 441 4 A -Pregnene-3,20-dione, see Progesterone progesterone, 412, 413, 416, 441, 445 5 A -Pregnene-3,20-dione, from cholesterol, 408, 409 activity of, 445 dehydroisoandrosterone, 420-424 conversion to progesterone, 445 5 3 (/3)-hydroxy-A -bisnorcholenic acid, partial synthesis of, 445 412, 415, 416 reduction of, 445 isolation from swine testis, 481 A5-Pregnene-4,20-dione, metabolic conversion to 3(a),20(a)- structure of, 417, 418, 419 pregnanediol, 454, 455 A16-Pregnene-3,20-dione, source of, 455 partial synthesis of, 410, 411, 445 Pregnenolone derivatives, A4-Pregnen-17"0"-ol-3,2O-dione, see 17- configuration of, 438-441 ' ' β ' '-Hy droxyprogesterone A4-Pregnene-21-ol-3,11,20-trione, see De- A4-Pregnen-21-ol-3,20-dione, see Desoxy- hydrocorticosterone corticosterone Pregnenin-17-ol-3-one, A4-Pregnene-ll(0),17"0",2O,21-tetrol- activity of, 439, 446, 539, 540 3-one, combined effect of, and estrone on metabolic conversion to 17-ketoster- mammary growth, 712 oids, 529, 530 partial synthesis of, 446 physical properties of, 553 Proestrogens, source of, 527, 553 formation of, following administration A4-Pregnene-11 (β) ,17"'β ",2 l-triol-3,20- of chorionic gonadotrophin, 397 dione, see 17-Hydroxycorticosterone 4 u ,, nature of, 399 A -Pregnene-17 /3 ,20,21-triol-3,ll-dione, metabolic conversion to 17-ketoster- Progesterone, oids, 529, 530 absorption spectrum, 340 physical properties, 553 accuracy of bioassay, 346 source, 527, 553 activity of, 440, 539, 540 A4-Pregnen-17u/3"-ol-3,20-dione, see 17- antagonism to androsterone, 538 il i ß '-Hydroxyprogesterone estrogens, 783-787 Pregnenolone, testosterone, 538 comparison of acetoxy-, with proges- bioassay of, 346 terone, 713 blood levels of, 4 conversion to progesterone, 455 combined action of estrogens and, on from cholesterol, 57 mammary growth, 709-712, 728 880 SUBJECT INDEX

comparison with acetoxypregnenolone, combined action of adrenocortical hor- 713 mones and, on lactation following desoxycorticosterone, 713 hypophysectomy, 756, 768 conversion to desoxycorticosterone, of estrogen and, on lactation, 776 436 effect on mammary gland, 749, 760, 798 pregnanediols, 425 pigeon crop gland, 748, 750, 760 pregnanolones, 425 growth activity of, 750 determination of, 335, 340 lactogenic activity of, 750-752 effect of ultraviolet light on, 438 luteotrophic activity of, 749 on lactation, 775, 798 Proline, in insulin, 308 mammary growth, 708, 713, 714, leaf growth activity of, 99 723, 728, 739 Protamine, combination with insulin, secretion of mammogen II, 722, 313, 314 723 Protein-auxin complexes, 23, 64 excretion of, 347 Protein précipitants, from allopregnane compounds, 417-419 effect on gonadotrophic hormones of bile acids, 412-417 anterior pituitary, 641 cholesterol, 408-410 Protein-steroid conjugates, 3 dehydroisoandrosterone, 420-424 Proteins, pregnane compounds, 415, 417-419 administration of iodinated, to dairy sapogenins, 410-412 animals, 770 stigmasterol, 409, 410 dietary, as source of auxins in urine, 22 international unit of, 334, 346 effect of iodinated, on milk fat, 794 metabolic conversion to 3(a),20(a)- purified wheat, as source of auxin, 22 pregnanediol, 454, 455, 457-459 Proteus X kingsbury, metabolism of, 447-460, 608, 609, 615, inhibitory effect on estrone, 394 619 Protoplasm, physical properties of, 556 effect of auxin on streaming of, 60, 61, partial synthesis of homologs of, 446- 65 447 relation between growth of plants and of isomers, 445, 446 streaming of, 60 role of kidneys in metabolism of, 458 Pseudoauxin a, liver in metabolism of, 458, 459 activity of, 19 sources of, 346, 447-455, 608, 619 conversion of auxin a into, 16 stereoisomerization of, 429 Pseudosarsasapogenin, synergism with pregnanediol, 347 from sarsasapogenin, 411 Progesterone derivatives, Ptychopoda seriata, eye color pigments in, activity of, 439 144 metabolism of, 447-460 Puberty, partial synthesis of, 438-447 urinary excretion of 17-ketosteroids in sources of, 447-454 precocious, 511 Progesterone, homologs of, Pupation, activity, 601 endocrine control of, 125-128 partial synthesis of, 446, 447 Purines, Progestin, effect of estrogens on, 453 effect on root formation, 111 Prolactin, see also Lactogenic hormone leaf growth activity of, 99 of anterior pituitary Pylorus, preparation of gastrin concen- antagonism to estrogens, 774 trate from, 241 assay of, 795-797 Pyridoxine clinical application of, 752 bioassay in plants, 105 SUBJECT INDEX 881

distribution in plants, 105 plant hormone activity of, 106 effect on estrogenic activity, 391 sources of, 106 plant hormone activity of, 105, 106 Rice, effect of polishings of, on rooting, 35 source of, 106 Rickets, transport through plants, 106 effect on parathyroid glands, 279 Pyrimidine, plant hormone activity of Ring gland, moiety of, 103 as source of developmental hormones in muscoid diptera, 127, 128, R 130, 133 Rabbit, occurrence of /3-estradiol in, 334 of GD hormone, 136 Radishes, isolation of auxin precursor effect of implants of, on testis of from, 24 Drosophila, 136 Ram, androgens in urine of, 516 on ovaries, 134, 151 Raphanus, transport of auxin through nature of hormones in, 139 seedlings of, 32 Roots, Rats, androgens in urine of, 516 effect of auxin on, 34, 35, 43-46, 82 effect of growth hormone on plateaued, carotene on formation of, 108 674 light on auxin content of, 46 ovariectomized, as test animals in nutrients on formation of, 37 bioassay of estrogens, 341, 342, pyridine on, 105, 106 344 thiamine on growth of, 104, 105, 111 "Redwood," 50 tryptophan on formation of, 24 Reproduction, vitamins Β on formation of, 37 effect of hormones on, of insects, 134- factors involved in formation of, 112 141 geotropism of, 34, 45, 46 Reproductive organs, growth activity of nicotinic acid for, effect of corpora allata on accessory, 106 136, 138 inhibitory effect of calcium on forma- on corpora allata, 136, 137, 140 tion of, 37 Respiration, magnesium on formation of, 37 relation between, and growth of plants, mechanism of nodule formation in, 52 58-60 methods of auxin application to, 38 Rhizocaline, 37, 111-113 nitrogenous substances required for activation of, 113 formation of, 111 as root-forming hormone, 57, 111 promotion of stem growth by, 114 distribution of, 113 thiamine content of, 103 interaction with auxin, 112 tissues producing, 38 Rhizopus suinus, Royal jelly, gonadotrophic substance in, isolation of auxin from cultures of, 15, 135 16, 35, 43 Rhodnius, effect of corpus allatum on S accessory sex glands of, 136 Safranal, on egg development in, 140 hormone activity of, 109 hormonal control of postembryonal source of, 108 development of, 152 Salivary glands, 243, 244 Rhodnius prolixus effect of corpora effect of hormones on secretion of, 243 allata on ovaries of, 134 perfusates of, on flow of saliva, 244 source of hormones in, 150 on carbohydrate metabolism, 243 Riboflavin, effect on estrogenic activity, isolation of blood sugar-lowering sub- 391 stance from, 244 882 SUBJECT INDEX

Salt, metabolism of, 215, 216 role of, in maintaining lactation follow- physiological effects of, 213-216 ing adrenalectomy, 763 polypeptide character of, 211 uptake of, and growth of plants, 64 sources, 206, 218, 235 Sapogenins, stability, 211 conversion to pregnane compounds, Secretin picrolonate, 410-412 empirical formula, 211, 217 to progesterone, 411, 416-417 melting point, 210 Sapromyces reinschii, molecular weight, 210 hormonal control of sexual reaction in, x-ray diffraction pattern of, 212 117 structure of, 217 Sarcophaga, Secretinase, 222 effect of castration on corpus allatum in blood, 215, 216 in, 136 sources, 217 of corpus allatum on accessory sex Seeds, effect of auxins on germination of, glands of, 136, 138 54, 55 Sarsasapogenin, Serine, in insulin, 308 conversion to 3(ß),16,20-pregnanetriol, Sex hormones, see also under Steroids 411 and under name of individual com- to A16--3,20, 410, 411 pounds to pseudosarsasapogenin, 411 effect on sex of Melandrivm dioecimti, Scabiosa atropurpurea, 108 effect of color of light on flowering of, growth activity for plants, 107 32 in insects, 140, 141 Sebacic acid, wound hormone activity of, sources, 335-337, 377, 385 79 Sitosterol, Secretin, see also Gastrointestinal hor- conversion of to dehydroisoandros- mones, 203-217 terone, 474 action on liver, 214 androsterone, 476 administration of, 216 progesterone, 410 antagonism to urogastrone, 246 Skin, absorption of androgens through, biological assay of, 203ff. 519 chemical properties of, 211 hypoparathyroidism and, 261 clinical applications of, 216 Skotoperiod, 89 composition of pure, 211 Sinus gland, conversion of prosecretin to, 206 as source of hormones in crustaceans, demonstration of, 203-206 185, 186, 190-192, 194 of pancreozymin in concentrate of, chromatophorotrophic activity of, 171- 217 173 effect on composition of pancreatic effect on formation of gastroliths, 189, juice, 214, 217 190 intestinal peristalsis, 233 molting, 188ff., 191 pancreas, 203ff. ovarian development, 195 salivary secretion, 243 number of chromatophorotrophic hor- effective doses, 213, 214 mones in, 182 hormonal nature of, 243 response of crustaceans to removal of, hypoglycemic, 235 173 inactivation of, 211, 215, 216 site of, 170 isolation of pure, 206, 208, 209 structure of, 171 methods of extraction, 206-208 Sodium glycocholate, SUBJECT INDEX 883

effect on transport of auxins, 29 Structure, chemical, Sodium, metabolism, auxin activity and, 19, 43 effect of adrenal cortex on, 263 carcinogenic activity and, 388 Sorbus, isolation of blastokolin from estrogenic activity and, 359 fruits of, 41 insulin activity and, 311 Spinacia oleracea, inhibitory effect of auxins and, 41 effect of color of light on flowering of, of vitamins for plant hormone activitv, 92 103 Spinach, isolation of auxin from, 23 wound hormone activity and, 79 Spleen, effect of intestinal extracts on Stylopization, 138, 140 contraction of, 234 Suberic acid, wound hormone activity of, implantation of estrogens into the, 79 390, 391 Succinic acid, wound hormone activity Stallion, androgens in urine of, 516 of, 79 Starch, effect of auxin on hydrolysis of, Suckling, 64 effect on pituitary prolactin levels, 790 Starvation, urinary excretion of andro- stimulating effect on lactation, 791- gens in, 514-515 793 17-ketosteroids in, 514-515 Sugar, effect on rooting, 35, 37 Statoliths, 32 water uptake in plants, 64 Stavely's steroid, 443 Sugar cane, activity of, 446 isolation of growth inhibitory auxin partial synthesis of, 446 from, 41 Steatorrhea, tetany due to, 265 Sulfur, in insulin, 309 Steroids, see also under Adrenocortical steroids, Hormones, Sex hormones Τ and names of individual compounds aromatization of, in the organism, 387 Teeth, effect of parathyroid on, 285, 291, chemical structure and absorption 292 spectrum of, 340 Testalolonc, activity of, 447 chemical properties, 482 chemistry of adrenocortical, 522-601 isolation from swine testis, 482 conjugation of metabolic, 456, 457 structure, 482 isolation from urine, 471 Testis, metabolism of adrenocortical, 602-623 activity of, 477 occurrence in plants, 108 as source of allopregnanediols, 619 phytochemical transformations of, 456 of allopregnanolones, 448 plant hormone activity of, 107, 108 of androgens, 481-483 Polarographie assay of, 340 of estrogens, 380, 381, 385 Stigmasterol, conversion to androsterone, of pregnanediol, 415, 619 476 of pregnenolones, 448 to 11-desoxycorticosterone, 551 of testosterone, 476, 477 to progesterone, 409, 410 effect of corpora allata on, 136 oxidation of, 410 formation of androgens in interstitial Stilbene, conversion to 4,4'-dihydroxy- tissue of, 469, 470 stilbene in vitro, 388 isolation of pure hormone from, 2 Stilbestrol, estrogenic activity of, 366 Testosterone, Stimulus, flower-forming, nature of, 96 absorption from gastrointestinal tract, photoperiodic, hormonal nature of, 88- 518 90 activity of, 446 884 SUBJECT INDEX

antagonism of estradiol to, 538 Thiazole, plant hormone activity of estrone to, 538 moiety of, 103 progesterone to, 538 Thioglycolic acid, inactivation of insulin bacterial conversion of, 535, 536 by, 309 biological conversion of estrogens to, reaction with lactogenic hormone, 658 398 Threonine, in insulin, 308 chemical determination, 494 Thylakentrin, see Follicle-stimulating configuration of, 361 hormone, of anterior pituitary reduction products, 428 Thyroid, effect on lactation, 775, 776, 777 effect on lactation, 767-773 mammary growth, 728, 729, 730 milk composition, 794, 795 parathyroid, 278 salivary secretion, 244 pituitary, 539 interrelationship between pituitary pituitary prolactin levels, 789 and, 661 from cholesterol, 477, 478 isolation of pure hormone from, 2 inactivation of, 534 relation to parathyroid glands, 278 isolation of, 1, 2 role of, in mammary growth, 731-734 metabolism of, 520-524, 526, 620 urinary excretion of androgens and metabolites of, 522-524, 534 diseases of, 509, 510, 515 modes of administration and activity of 17-ketosteroids and diseases of, of, 534 509, 510, 515 Testosterone propionate, absorption by Thyroidectomy, various routes, 518, 519 effect of estrogens on mammary growth effect on rachitic rats, 538 following, 731-733 , 492 effect on lactation, 767-770 bioassay of, 493 pituitary prolactin levels, 789 Thyroparathyroidectomy, Testriol, effect on pituitary prolactin levels, 789 chemical properties, 482 skeletal growth, 289, 290 identity with chimyl alcohol, 483 urinary excretion of radioactive isolation from swine testis, 482, 483 phosphorus, 267 structure of, 482 neuromuscular symptoms following, Tetany, 265 due to steatorrhea, 265 Thyroxine, administration to dairy ani- pathogenesis of infantile, 286 mals, 770, 772 prevention of parathyroprival, by dex- effect on milk fat, 794 trin, 264 synergism with androgens, 538 by lactose, 264 Tigogenin, conversion to A16-allopreg- symptoms of, 285 nene-3,20-dione, 411 treatment of, 268, 286 Tissue, "ferments", 1 Thayer-Doisy procedure, for estrogen response of, of insects to hormonal assay, 344 stimuli, 129, 132 Theelin, see Estrone Tomatoes, growth activity of pyridoxine Thiamine, distribution in plants, 103ff. for, 105 effect on estrogenic activity, 391 isolation of growth-inhibiting auxin root formation, 37 from, 41, 44 formation in leaves, 104, 105 thiamine distribution in, 104 leaf growth activity of, 99 Tradescantia, effect of auxin on root plant hormone activity of, 102-105 formation in, 36 transport through plants, 104 Traumatic acid, 77ff. SUBJECT INDEX 885

co-factors of, 78 Urane, effect of glutamic acid on activity of, 79 source, 618 formation of, 82 structural formula, 618 identity with A^decene-^lO-dicarbox- Urane derivatives, ylic acid, 78 configuration of, 450 interaction with auxin, 82 Uranediol, source, 618 isolation from bean pods, 78 structural formula of, 618 isomer of, 79 Uranetriol, source, 618 Traumatin, see Traumatic acid structural formula of, 618 A^Tridecene-ljlS-dicarboxylic acid, 3(ß),ll-Uranediol, sources of, 447 wound hormone activity of, 79 3(a),ll,20-Uranetriol, A2-Tridecene-l,13-dicarboxylic acid, sources of, 447, 450 wound hormone activity of, 79 structure of, 451 Triodobenzoic acid, Uranolone, source of, 618 antagonism to auxin, 95 structural formula of, 618 Triphenylethylene, antagonism of andro- Uran-ll-ol-3-one, sources of, 447, 450 gens to, 539 structure of, 451 Tropaeolum, Urea, effect on growth hormone, 685 leaf abnormalities in, 101 on lactogenic hormone, 660 Trypsin, Urine, effect on hormones of anterior pitui- adrenocortical metabolites in, 602-621 tary, 660, 665, 673, 684 androgens in, 471-474, 484, 496-516 inactivation of insulin by, 313 dietary origin of auxin in human, 21, 22 Tryptamine, effect of men's, on castrated mice, auxin activity of, 20 472 conversion to auxin, 25 enterogastrone in, 244ff. indoleacetic acid, 24, 25 estrogens in, 374, 381, 386, 387 relation to auxin, 22 excretion of progesterone into, 347 role in eye pigment formation of extraction of auxin from, 35 Drosophila, 144, 145 isolation of allopregnanederivatives Tumors, from, 445, 448 adrenal, and urinary excretion of androgen sulfate esters from, 485 adrenocortical metabolites, androstene derivatives from, 472 614-618, 620 3-desoxyequilenin from, of pregnant of estrogens, 621 mares, 389 effect on urinary excretion of 17- equilenin from, of pregnant mares, ketosteroids, 510-514, 515 355, 359 Tyrosinase, inhibitory effect on estrone, pregnane derivatives from, 448, 449, 393 457 Tyrosine, in insulin, 308 17-ketosteroids in, 486-488, 496-517, wound hormone activity of, 393 602 Polarographie assay of 17-ketosteroids U in human, 340 progestin in, 452 Ulcers, gastrojejunal, effect of entero- prolactin in, 795 gastrone on, 230 sex hormones in, 335-337, 377 6-Undecanol-l,ll-dicarboxylic acid, urogastrone in, 245 wound hormone activity of, 79 Urogastrone, 244-246 A6-Undecene-l,ll-dicarboxylic acid, antagonism to histamine, 246 wound hormone activity of, 79 secretin, 246 886 SUBJECT INDEX

comparison with enterogastrone, 245 structural requirements for plant hor- effect on gastric secretion, 245, 246 mone activity, 103 salivary secretion, 246 isolation from urine, 245 W Uterus, effect of desoxycorticosterone on, 347 Water, effect of intake of, on lactation of methyltestosterone on, 347 following adrenalectomy, 763 of ovarian hormones on, 708 relation between growth of plants and of progesterone on, 346, 347 uptake of, 63-65 lactogenic effect of pregnant, 755 Wheat, response of immature, to estrogen, 345 purified proteins of, as source of auxin, role in estrogen metabolism, 385 22 WTomen, urinary excretion of androgens V in normal, 502-504, 515 in eunuchoid, 506-508, 515 Vasodilatin, 17-ketosteroids in normal, 502- identity with histamine, 240 504, 515 isolation from tissue extracts, 240 eunuchoid, 506-508 Vicia, auxins in, 17 Wound callus, formation of, in plants, 76 Vicia faba, hormones from, 76 Wound hormone, see Hormones, wound, Villikinin, 234 in plants Viosterol, effect on parathyroprival tetany, 286 X Vitamin Λ, effect on inactivation of estrogens by liver, 392 Xanthium pennsylvanicum, 93 Vitamin A deficiency, day-lengths required for flowering, 84 effect on bioassay of estrogens, 344 Vitamin Bi, see Thiamine Y Vitamin Be, see Pyridoxine Yeast, plant hormone activity of, 102, Vitamin Β deficiency, effect on bioassay 114 of estrogens, 344 reduction of androstanedione by, 534, effect on inactivation of estrogens by 536 liver, 391, 395 Vitamin D, of androstenedione by, 534-536 effect on bone repair, 291 intestinal absorption of, and blood Ζ calcium level, 265 Vitamin E, synergism with androgens, Zinc, occurrence in human pancreas, 307 537 in crystalline insulin, 307 Vitamin K, interaction with secretin, 215 Zinc-insulin complex, Vitamins, as plant hormones, 102-107 action of, 313 leaf growth activity of, 99 Zygomycetes, hormonal control of sexual reactions in, 117