Start of Citation[PU]Marcel Dekker[/PU][DP]1999[/DP]End of Citation Page i The Biology-Chemistry Interface A Tribute to Koji Nakanishi edited by Raymond Cooper Pharmanex, Inc San Francisco, California John K Snyder Boston University Boston, Massachusetts Start of Citation[PU]Marcel Dekker[/PU][DP]1999[/DP]End of Citation Page ii ISBN: 0-8247-7116-8 This book is printed on acid-free paper Headquarters Marcel Dekker, Inc 270 Madison Avenue, New York, NY 10016 tel: 212-696-9000; fax: 212-685-4540 Eastern Hemisphere Distribution Marcel Dekker AG Hutgasse 4, Postfach 812, CH-4001 Basel, Switzerland tel: 41-61-261-8482; fax: 41-61-261-8896 World Wide Web http://www.dekker.com The publisher offers discounts on this book when ordered in bulk quantities For more information, write to Special Sales/Professional Marketing at the headquarters address above Copyright © 1999 by Marcel Dekker, Inc All Rights Reserved Neither this book nor any part may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying, microfilming, and recording, or by any information storage and retrieval system, without permission in writing from the publisher Current printing (last digit): 10 PRINTED IN THE UNITED STATES OF AMERICA Start of Citation[PU]Marcel Dekker[/PU][DP]1999[/DP]End of Citation Page iii Preface Natural products science, a fascinating cornerstone of modem research, has long bridged the traditional frontier between chemistry and biology Humankind has always been intrigued by the power and potential of plants and nature Many old texts reveal how the ancient cultures drew on the beneficial properties of plants They learned the wisdom of extracting the ingredients and using such potions as foods, medicines, and mood enhancers long before anyone understood how these worked Slowly we have found the tools to explore the chemistry of these ingredients, and thus the systematic study of natural products began Morphine was isolated in 1805 and strychnine in 1819, although their structures remained mysteries for more than 100 years, and pure camphor has been an article of commerce for centuries Today the biosynthetic machinery of plants and other organisms is purposefully manipulated to produce new "natural products" of biological significance in medicine and agriculture In the nineteenth century, early progress in natural products research centered on the study of pigments from flowers as colored dyes Originally, extraction of drug compounds, particularly alkaloids, from plants was achieved by using simple isolation methods: a water steep or a solvent (generally alcohol) extraction The impetus was set to explore this research area further and, not surprisingly, more and more intellectual pursuit of natural sciences and our environment encouraged universities and scientific centers throughout the world to study natural products, which then formed the nucleus of chemistry programs As source material to begin any research investigation, plants were abundant and easily obtained The first natural products to be studied in detail were generally the major constituents of plants, since these often precipitated from solution and could be purified through recrystallization How well we recall Start of Citation[PU]Marcel Dekker[/PU][DP]1999[/DP]End of Citation Page iv today that the purity of chemicals up to the latter half of the twentieth century was determined solely by melting point? As increasing numbers of chemical constituents with more complexity were found, structural analysis relied on chemical transformations and degradation studies Total synthesis was confirmatory The discovery of one or two compounds based on these research studies was usually acceptable to earn a doctorate The second half of the twentieth century has witnessed incredible advances in natural products research These have been achieved through the discovery of new chromatographic separation methods and remarkable advances in spectroscopy As new technologies for isolation and structure identification have evolved, the isolation and detection of ever-diminishing amounts of natural products, coupled with the determination of structures on a microscale, have become almost routine In addition to identifying important targets for total synthesis, and thereby spurring innumerable advances in fundamental organic chemistry, studies of natural products have led to significant research efforts in the related fields of bioorganic chemistry and biosynthesis, as chemists, biologists, and biochemists have striven to understand how these molecules are produced in nature and to establish the molecular basis of the biological activity of these compounds The structural determination of natural products has impacted our basic understanding of nature One very important aspect of structure determination is the use of spectroscopy, particularly nuclear magnetic resonance, mass spectrometry, circular dichroism, and x-ray diffraction methods Circular dichroism is particularly important in establishing absolute stereochemistry, as chirality is correlated directly to biological activity of the biomolecule Thus, as we approach the end of this century, we see the challenging questions in biology requiring answers at the molecular level being met by increasingly sophisticated techniques and comprehension of the chemistry of nature Professor Koji Nakanishi has been a pioneer and a towering figure in natural products research He has been a major contributor at the crossroads of bioorganic chemistry over the past 40 years His extraordinary and broad vision of natural products chemistry and its close relationship to bioorganic studies is now universally accepted and was the inspiration for this book He has constantly looked at challenges in bioorganic chemistry and pushed ever closer the boundaries at the interface between chemistry and biology He has achieved this through his lifelong studies in natural products, his investigations into the chemistry of vision, his pursuit of new and ever more powerful analytical and spectroscopic microtechniques for solving complex structural problems, and his study of infrared and circular dichroism and their applications to bioorganic science Koji's curiosity and insights in applying the right solution to challenging problems are among his legacies, to which we as students of his are deeply grateful Koji Nakanishi was born in 1925 in Hong Kong to parents of Japanese Start of Citation[PU]Marcel Dekker[/PU][DP]1999[/DP]End of Citation Page v descent As a result of his father's business postings abroad, Koji's early childhood was spent in various European capitals as well as in Alexandria, Egypt, thereby giving birth to and nurturing his unique world vision He returned to Japan for his formal university training and received his B.Sc degree at Nagoya University in 1947 He first came to the United States in 1950–52 to study with the legendary Professor Louis Fieser at Harvard University, and he returned to Japan as an assistant professor to embark on his remarkable career in natural products and bioorganic chemistry He completed his Ph.D in 1954 under the mentorship of Professors Egami and Hirata, then took positions at Nagoya University (1955–58), Tokyo Kyoika University (1958–63), and Tohoku University (1963–69) In 1969 he was invited to join the faculty at Columbia University, New York, where he currently holds the chair of "Centennial Professor of Chemistry." Indeed, it was at Columbia University that former and current students, postdoctoral fellows, and esteemed colleagues of Professor Nakanishi gathered to celebrate his 70th birthday and to honor him for his years of mentorship and friendship, as well as for his considerable contributions to bioorganic science Two days of stimulating presentations on various topics in bioorganic chemistry gave birth to the idea behind this book: to produce a volume with contributed chapters from his former students in his honor This text reflects Koji's own research interests in its scope and attempts to bridge the gap between biology and chemistry: a gap that is rapidly diminishing as investigators use the tools and vision that Koji has provided Koji humbly reminds us that he is "only a technician"; we respectfully differ He is a visionary, and in essence the investigatory seeds planted by Koji are now in full bloom in research gardens headed by those he taught We choose to highlight current research activities from former members of his research groups from Asia, the United States, Europe, and Australia, thereby illustrating Koji's global scientific influence As with Koji's own research, one goal of this text is to further dissolve the boundary that has kept chemistry and biology apart; the contributions in this volume are by investigators for whom this boundary has long since disappeared It is hoped that readers will come to understand the highly interactive nature of research in biological chemistry and chemical biology, and find the transition between chemistry and biology far less intimidating Thus, this book reflects the ideals of Professor Nakanishi and his impact Although the chapter titles may at first glance seem to suggest a relatively large breadth of subjects, in fact they all fit snugly within the focus of the chemical basis of biological activity Subjects range from hydrolytic enzymes to combinatorial chemistry, yet all the chapters strive to elucidate biological responses at the molecular level The contributing authors provide detailed accounts of their current research rather than presenting formal reviews of disparate subjects The Start of Citation[PU]Marcel Dekker[/PU][DP]1999[/DP]End of Citation Page vi rationale for this approach is to emphasize the interactive nature of the research in bioorganic chemistry The unifying theme throughout is the original skills that developed in natural products research and chemistry of vision The microanalytical techiques, the spectroscopic challenges, have now evolved into the application of chemical minds to biological problems Thus, the selection of authors reflects a blend of investigations in academic and industrial research Koji's pioneering contributions and world vision of science have inspired several generations of chemists from around the globe, and demonstrations of his mastery of the magical arts have left numerous audiences of the brightest minds completely and delightfully mystified We can identify the defining moment of our education and scientific growth as the time we spent with Koji, and we offer our profoundest gratitude to him for his tireless leadership and support RAYMOND COOPER JOHN K SNYDER Start of Citation[PU]Marcel Dekker[/PU][DP]1999[/DP]End of Citation Page vii Contents Preface iii Contributors ix Tribute Letters xiii Insect Antifeeding Limonoids from the Chinaberry Tree Melia azedarach Linn and Related Compounds Munehiro Nakatani Polygodial and Warburganal, Antifungal Sesquiterpene Dialdehydes and Their Synergists Isao Kubo 23 Marine Bromoperoxidases—Chemoenzymatic Applications Chris A Moore and Roy K Okuda 43 LC-Hyphenated Techniques in the Search for New Bioactive Plant Constituents Kurt Hostettmann, Maryse Hostettmann, Sylvain Rodriguez, and Jean-Luc Wolfender 65 Determination of the Absolute Configuration of Biologically Active Compounds by the Modified Mosher's Method Takenori Kusumi and Ikuko I Ohtani 103 Circular Dichroism Spectroscopy and the Absolute Stereochemistry of Biologically Active Compounds Nobuyuki Harada 139 Start of Citation[PU]Marcel Dekker[/PU][DP]1999[/DP]End of Citation Page viii Recent Applications of Circular Dichroism to Carbohydrate Conformational Analysis and Direct Determination of Drug Levels Jesús Trujillo Vázquez 191 Furan-Terminated Cationic π-Cyclizations in the Synthesis of Natural Products Steven P Tanis 221 Chemistry and Biology of Semisynthetic Avermectins Timothy A Blizzard 257 10 Chemical and Biological Approaches to Molecular Diversity: Applications to Drug Discovery Harold V Meyers 271 11 Imidazoline Receptors and Their Endogenous Ligands Colin J Barrow And Ian F Musgrave 289 12 Oxidoredox Suppression of Fungal Infections by Novel Pharmacophores Valeria Balogh-Nair 311 13 A Mechanistic Analysis of C—–O Bond Cleavage Events with a Comparison to 3,6-Dideoxysugar Formation David A Johnson and Hung-Wen Liu 351 14 The Molecular Mechanism of Amyloidosis in Alzheimer's Disease Michael G Zagorski 397 15 Bacteriorhodopsin Structure/Function Studies: Use of the Demethyl Retinal Analogues for Probing of the Arg82Ala Mutant Rosalie K Crouch, Donald R Menick, Yan Feng, Rajni Govindjee, And Thomas G Ebrey 431 16 Autonomous Genomes David G Lynn 445 17 Stereochemical Considerations of Immunoglobulin Heavy Chain Enhancer Activation Barbara S Nikolajczyk And Ranjan Sen 461 Index 473 Start of Citation[PU]Marcel Dekker[/PU][DP]1999[/DP]End of Citation Page ix Contributors Valeria Balogh-Nair Department of Chemistry, The City College of the City University, New York, New York Colin J Barrow School of Chemistry, The University of Melbourne, Parkville, Victoria, Australia Timothy A Blizzard Medicinal Chemistry, Merck Research Laboratories, Rahway, New Jersey Rosalie K Crouch Department of Ophthalmology, Medical University of South Carolina, Charleston, South Carolina Thomas G Ebrey School of Cellular and Molecular Biology, University of Illinois at UrbanaChampaign, Urbana, Illinois Yan Feng Department of Ophthalmology, Medical University of South Carolina, Charleston, South Carolina Rajni Govindjee Center for Biophysics and Computational Biology and Department of Cell and Structural Biology, University of Illinois at Urbana-Champaign, Urbana, Illinois Start of Citation[PU]Marcel Dekker[/PU][DP]1999[/DP]End of Citation synthesis of, 230-231 Pamamycins, absolute stereochemistry from modified Mosher's method, 110 Parallel synthesis (see Combinatorial synthesis, Multiple simultaneous synthesis) Paratose, 378 Pargyline, 77 Parkinson's disease, 76 Pateamine A, absolute stereochemistry from modified Mosher's method, 110, 115 Penicillium chrysagenum sesquiterpene dialdehyde effect on, 24 Pentanoic acid, (S)-2-methyl-, chiral anisotropic reagents applied to, 132, 133 Pent-4-enoic acid, (S)-2-methyl, chiral anisotropic reagents applied to, 132, 133 Peptostreptococcus asaccharolyticus, L-serine dehydratase from, 363, 364 Peroxidases, apoplastic, 448 Peroxide shunt, 321 Perhydrohistrionicotoxin, 249, 250 Petrosynol, 111 Pfitzner Moffat oxidation, 170 Phage libraries (see Combinatorial libraries) L-Phenylalanine methyl ester, modified Mosher's method applied to, 127 L-Phenylalaninol, modified Mosher's method applied to, 127 Phenylglycinamide, N,N-dimethyl-(PGDA), 104 as a chiral anisotropic reagent 128-133 preparation of, 130 Phenylglycine, methyl ester (PGME), 104 as a chiral anisotropic reagent 128-133 preparation of, 130 Phenylpropanoids, 32 anethole, 32, 35 eugenol, 32 methyleugenol, 32 safrole, 32 Phloroacetophenone, 181 Phomactin B, absolute stereochemistry from modified Mosher's method, 112 2-Phospho-D-glycerate (2-PGA), 357, 358 Start of Citation[PU]Marcel Dekker[/PU][DP]1999[/DP]End of Citation Page 487 Phosphoglycolate, 358 Phosphonoacetohydroxamate (PhAH), 358 Photodiode arrary detection, coupled with liquid chromatography, 67-70 π-Electron self-consistent field/configuration interaction/dipole velocity molecular orbital method (SCF-CI-DV MO), 139-142 applied to (8aR)-1, 8a-dihydroazulene, 145-146 applied to halenaquinol dimethyl ether, 155-156 applied to naphthalene-diene systems, 159-162 applied to (–)-4', 4'', 7, 7"-tetra-O-methyl-cupressuflavone, 175-180 Pimpinella anisum (Umbelliferae), 32 Pipemidic acid, 208 Plasmid genes, 447 Pneumocystis carinii oxidoredox suppression of, 311-312, 340-341, 344 synthesis of antifungal drugs active against, 331, 332-336 Polygonum hydropiper (Polygonaceae), 25 Polymerase chain reaction (PCR), 436 in split synthesis, encoding strategies, 277 Prazosin, 208 Prehalenaquinol, 171-172 Prehalenaquinone, 152, 171-173 dimethyl ether, 170 Prion proteins, 404 (S)-1, 2-Propanediol, dehydration of by diol dehydrases, 373, 374 Pteroenone, absolute stereochemistry from modified Mosher's method, 114 Ptychantin A, absolute stereochemistry from modified Mosher's method, 112 Putidaredoxin, 380 PU.1 (protein), 466-471 Pyridoxal 5'-phosphate (PLP), 363, 364, 365, 380, 384-386 Pyridoxamine-5'-phosphate (PMP), 352, 379, 380, 381, 383, 384-386 Pyridoxamine-5'-phosphate-∆3,4-glucoseen complex, 379, 380, 382, 383, 384, 385 Pyruvate, 364 Pyruvate-formate lyase, 377, 378 Q o-Quinodimethane, 162, 163, 166 R Ranitidine, 208 Raspailol A, absolute stereochemistry from modified Mosher's method, 114 Resonance Raman, studies of dihydroxy-acid dehydratase, 362 Retinal, 431 13-cis, 431, 433 9-demethyl, 432, 434 pigment formation with bacteriorhodopsin, 439-442 synthesis of, 438 13-demethyl, 432, 434 pigment formation with bacteriorhodopsin, 439-442 synthesis of, 438 9, 13-didemethyl, 432 pigment formation with bacteriorhodopsin, 439-442 synthesis of, 438 Rhodanthoside A, 80, 84-86 from Gentiana rhodantha, LC/MS of, 85 Rhodanthoside B, 80, 84-86 from Gentiana rhodantha, LC/MS of, 85 Rhodobacter capsulatus, fumarate hydratase from, 361 Ribonucleotide reductase, 351, 373, 375-378, 387 Rietone, absolute stereochemistry from modified Mosher's method, 113 Start of Citation[PU]Marcel Dekker[/PU][DP]1999[/DP]End of Citation Page 488 Rilmenidine, 290, 297 Ritterazine C, absolute stereochemistry from modified Mosher's method, 113 Rotational strength (Rba), 141 Rutales, order, S Saccaromyces cerevisiae sesquiterpene dialdehyde effect on, 24, 25 Sanadaol, absolute stereochemistry from modified Mosher's method, 108, 109 Saraine A, absolute stereochemistry from modified Mosher's method, 116 Saraine B, absolute stereochemistry from modified Mosher's method, 116 Saraine C, absolute stereochemistry from modified Mosher's method, 116 Scout Scan, 95 Secoiridoids, 77, 79, 80 L-Selectride reductions, 233, 234 Sendanal, Senile dementia, 76 L-Serine conversion to pyruvate, 363-364, 365 metabolism of, 363 methyl ester, modified Mosher's method applied to, 127 L-Serine dehydratase, 363, 364, 365, 384 Serotonin, 76 Serum, human determination of drugs in, 208-215 Sesquiterpene dialdehydes, 23-39 activity on plasma membrane, 35-37 antifeedant assay, 24 antifungal activity of, 27-36 oxidoredox suppression, 311-345 principles, isolation and identification of, 25 Canellaceae family, 24 congeners of, 25 bemadienolide, 25 cinnamosnolide, 25 colorata-4, 25 confertifolin, 25 8-dienolide, 25 epipolygodial, 25 9α-hydroxycinnamolide mukaadial, 25 muzigadial (canellal), 24 ugandensidial (cinnamodial), 25 structures, 25, 26 synergy, 29, 32 addition of excess Ca2+, 29, 31, 37 maesanin, antifungal activity of, 29 syntheses, 25 Warburgia genus, 24 antimicrobial activity of, 27 epipolygodial (C-9 epimer), 28 W stulmannii, 24, 26 W ugandensis, 24, 25 muzigadial (canellal), 24, 28 polygodial, 24, 25, 28, 36 warburganal, 24, 28, 33 Sharpless asymmetric epoxidation, 231, 232 Shikimate pathway, 355, 371 Sipholenol A, absolute stereochemistry from modified Mosher's method, 119-120 SOAK Assembly operation, 417 Solid phase synthesis, biphenyl scaffold, 281-283 Sorghum, 447 Southern army worm (see Spodoptera eridania (Boisduval)) Spacermectins, 263, 264, 267 Spin traps CP-H, 326 nitrones as, 324 TEMPONE-H, 326 Spinach, carbonic anhydrase from, 357 dihydroxy-acid dehydratase from, 362, 384 Spirosendan, Split pool synthesis (see Combinatorial chemistry, split synthesis) Start of Citation[PU]Marcel Dekker[/PU][DP]1999[/DP]End of Citation Page 489 Spodoptera S eridania (Boisduval), (Southern army worm), 7, S exempta, 24 Squalene, 116 Squamostatin D, absolute stereochemistry from modified Mosher's method, 112 Squamostatin E, absolute stereochemistry from modified Mosher's method, 112 Stille coupling, in solid phase synthesis, 282, 283 Streptomyces avermitilis, 257 Striga, 450 S asiatica, 447, 448 S haustoria, 448 Suberitenone B, absolute stereochemistry from modified Mosher's method, 114 Sulfonyloxaziridines, synthesis of, 332 Superstolide A, absolute stereochemistry from modified Mosher's method, 112, 123, 124 Swerchirin (see Xanthone, 1, 8-dihydroxy3, 5-dimethoxy-) Sweroside, 79, 80, 84, 85, 93, 94, 95, 96, 97 7-β-[4'-O-(β-D-glucopyranosyl)-transcaffeoyloxy]- (corniculoside), 87 from Halenia corniculata, LC/ES-MS of, 89 from Halenia corniculata, LC/MS of, 88 from Halenia corniculata, LC/UV of, 89 from Chironia krebsii, LC/UV of, 81 from Gentiana rhodantha, LC/MS of, 85 from Swertia calycina, LC/NMR of, 93 from Swertia calycina, LC/UV of, 94 from Swertia calycina, WET-COSY of, 96 Swertia calycina antifungal activity of, 93, 96- 97 flavonoids of, 80, 87-93 LC/ES-MS analysis of, 90 LC/NMR analysis of, 93, 85-97 LC/TSP-MS analysis of, 90 LC/UV/MS analysis of, 87-93 Swertiajaponin, 80, 91, 93 from Swertia calycina, LC/MS of, 90 Swertiamarin, 79, 80 from Chironia krebsii, LC/UV of, 81 Swertisin, 80, 91, 93 from Swertia calycina, LC/MS of, 90 Swinholide A, absolute stereochemistry from modified Mosher's method, 110 T Tanabalin, modified Mosher's method applied to, 122-123 Tanacetum balsamita, 122 Tautomycin, application of modified Mosher's method during the synthesis of, 121-122 Tetrahydroxestoquinonol, 152 Tetranortriterpenoids, TFE3 (protein), 466, 467, 469-471 Theophylline, 208 Thioredoxin, 376 Thioredoxin reductase, 383 L-Threonine conversion to β-ketobutyrate, 364, 365 methyl ester, modified Mosher's method applied to, 127 L-Threonine dehydratase, 363-364, 365, 384 Thymidine diphosphate-D-glucose 4, 5dehydratase, 364-367 Ti plasmid, 451-453 Titanium (III) citrate, (R)-2-hydroxylglutaryl-CoA dehydratase activation by, 367 Tobramycin, 208 Triazolam, 208 Trichilia roka (Meliaceae), Trichilin, 2, 4, 9-11, 14-17 Trinoranastreptene, 143, 146 Start of Citation[PU]Marcel Dekker[/PU][DP]1999[/DP]End of Citation Page 490 Trinorsesquiterpene, 142 Triterpenoids, L-Tryptophan methyl ester, modified Mosher's method applied to, 127 Tyvelose, 378 U Ultra-violet spectroscopy post column addition of shifts reagents, 69-70 Uric acid, 216 Urine, human, determination of drugs in, 207-215 V L-Valine biosynthesis of, 362 methyl ester, modified Mosher's method applied to, 127 Vinylacetate-CoA, 369, 370 Virulence regulon, 452 Vitamin C, 208, 209 VBN-1, 340, 341 VBN-2 (macrobicyclic oxaziridine), 333-335, 337, 340, 341, 344, 345 VBN-3, 326-327, 335, 336, 340, 341, 344, 345 VBN-4, 335, 336, 340, 341 VBN-5-9, 337, 340, 341 VBN-10, 331, 337, 339, 340, 341 VBN-11-14, 340, 341 Vogelside, 80, 87 from Halenia corniculata, LC/MS of, 88 epi-Vogelside, 80, 87 from Halenia corniculata, LC/MS of, 88 W Wailupemycin A, absolute stereochemistry from modified Mosher's method, 116 Warburganal, 23, 221 attempted synthesis of, 221-222 synthesis of, 223-224 Warburgia W stuhlmannii, 24 W ugandensis, 24, 221 WET (water suppression enhanced through T1 effect), 73, 95, 96, 97 Wieland–Miescher ketone, 147, 163, 164, 165, 169 X Xanthone as MAO inhibitors, 76-77 1, 8-dihydroxy-3, 5-dimethoxy- (swerchirin), 77 1, 5-dihydroxy-3-methoxy-, 79, 80, 84 from Chironia krebsii, LC/UV of, 81 inhibition of MAO-A, 84 1, 7-dihydroxy-3-methoxy- (gentisin), 77-78 7, 8-dihydroxy-3-methoxy-1-O-primeverosyl-, 79, 80 from Chironia krebsii, LC/UV of, 81 1, 6-dihydroxy -3, 5, 7, 8-tetramethoxy-, 79, 80 from Chironia krebsii, LC/UV of, 81 3, 5-dimethoxy-1-O-primeverosyl-, 79, 80 from Chironia krebsii, LC/UV of, 81 1-O-glucosyl-5-hydroxy-3-methoxy-, 79, 80 from Chironia krebsii, LC/UV of, 81 1-hydroxy-3-methoxy-5-O-primeverosyl-, 79, 80, 83, 84 from Chironia krebsii, LC/UV of, 81, 82 from Chironia krebsii, LS/TSP-MS of, 82 5-hydroxy-3-methoxy-1-O-primeverosyl-, 79, 80, 83, 84 from Chironia krebsii, LC/UV of, 81 from Chironia krebsii, LC/TSP-MS of, 82 1-hydroxy-3, 5, 6, 7, -pentamethoxy-, 79, 80, 83, 93, 94, 95 Start of Citation[PU]Marcel Dekker[/PU][DP]1999[/DP]End of Citation Page 491 [Xanthone] from Chironia krebsii, LC/UV of, 81 from Chironia krebsii, LC/TSP-MS of, 81 from Swertia calycina, LC/NMR of, 93 from Swertia calycina, LC/UV of, 94 1-hydroxy-3, 7, 8-trimethoxy-, (decussatin), 79, 80, 83 from Chironia krebsii, LC/UV of, 82 from Chironia krebsii, LC/TSP-MS of, 82 3-methoxy-1, 5, 8-trihydroxy-, (bellidifolin), 77 3-methoxy-1, 7, 8-trihydroxy-, 79, 80, 83 from Chironia krebsii, LC/TSP-MS of, 82 from Chironia krebsii, LC/UV of, 81, 82 2, 3, 4, 5, 7-pentamethoxy-1-O-primeverosyl-, 79, 87 from Halenia corniculata, LC/MS of, 88 3, 5, 6, 7, 8-pentamethoxy-1-O-primeverosyl-, 79, 80, 83 from Chironia krebsii, LC/TSP-MS of, 81 from Chironia krebsii, LC/UV of, 81 1-O-primeverosyl-2, 3, 4, 5-tetramethoxy-, 80, 87 from Halenia corniculata, LC/MS of, 88 1-O-primeverosyl-2, 3, 4, 7-tetramethoxy-, 80, 87 from Halenia corniculata, LC/MS of, 88 1-O-primeverosyl-2, 3, 5-trimethoxy-, 80, 87 from Halenia corniculata, LC/MS of, 88 1-O-primeverosyl-2, 3, 7-trimethoxy-, 80, 87 from Halenia corniculata, LC/MS of, 88 1, 3, 5, 8-tetrahydroxy-, (desmethylbellidifolin), 77 1, 3, 7, 8-tetrahydroxy-, 79, 80 from Chironia krebsii, LC/UV of, 81 1, 3, 7-trihydroxy-, 79, 80 from Chironia krebsii, LC/UV of, 81 Xenognosin, 447, 448 Xenognosis, 447 receptor, 453 signals, 448 Xestoquinol, 153 dimethyl ether, 170 synthesis of, 170-171 Xestoquinone, 152 synthesis of, 169-171 Xestospongia exigua, 151 Xestospongia sapra, 152, 172 X-ray crystallography Bijovet method, 140, 151 Y Yeast enolase from, 358 fumarate hydratase from, 361 Yersinia pseudotuberculosis, biosynthesis of ascarylose by, 378 thymidine diphosphate-D-glucose 4, -dehydratase from, 365 Start of Citation[PU]Marcel Dekker[/PU][DP]1999[/DP]End of Citation ... in the middle of the huge estate he had bequeathed to the township of Brookline, Lars Andersen Park The stables were in the form of the Chateau de Chambord, or nearly so, and were the seat of the. .. Marcel Dekker AG Hutgasse 4, Postfach 812, CH-4001 Basel, Switzerland tel: 4 1-6 1-2 6 1-8 482; fax: 4 1-6 1-2 6 1-8 896 World Wide Web http://www.dekker.com The publisher offers discounts on this book... Citation Page ii ISBN: 0-8 24 7-7 11 6-8 This book is printed on acid-free paper Headquarters Marcel Dekker, Inc 270 Madison Avenue, New York, NY 10016 tel: 21 2-6 9 6-9 000; fax: 21 2-6 8 5-4 540 Eastern Hemisphere