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NATURALPRODUCTS
NEXUS
New Research Brings Essential Oils Back to the Future Extracted from the flowers, seeds, leaves, stems, bark, and roots, essential oils can be considered the soul of the plant. According to ancient Egyptian hieroglyphics and Chinese manuscripts, priests and alchemists used them not only in religious ritual but also to heal the sick. Some sealed flasks discovered in King Tutankhamun’s tomb contained an unguent that, after 3300 years, still had a perceptible odor. Subsequent analysis revealed the presence of frankincense and spikenard, making this, perhaps, the only surviving bottle of the world's first perfume. Ayurvedic literature as early as 2000 B.C. records Indian doctors administering oils to their patients. The ancient Greeks employed them cosmetically and medicinally and the Romans bathed with them several times a day, using them to scent the hair, the body, and even the bed. Today, society looks to science to document health choices and the oils do not disappoint. Recent studies have shown the usefulness of the terpenes found in essential oils for chemoprevention, treating atherosclerosis and thrombosis, and skin penetration enhancers for transdermal drug delivery as well as for antibacterial, antimicrobial, antidiabetic, and antiviral agents. Promising research has revealed that some essential oils kill methicillin-resistant Staphylococcus aureus, E. coli, and other bacteria and fungi within two minutes of contact. The key to this effectiveness lies in their makeup — a complex mixture of chemical compounds that the MRSA and other super bugs find difficult to resist.
Alternative Px
Best Practices and Quality Control Come to Age The growing body of evidence suggesting efficacy for more than just scenting a room underscores the need for production standards, quality control parameters for raw materials and finished products, and well-defined Good Manufacturing Practices. In Essential Oil Bearing Grasses: The genus Cymbopogon (CRC Press 2009) Anand Akhila brings together a team of experts to define best practices from harvest to postharvest and extraction. They discuss analytical methods for identifying terpenes and developments in biotechnological approaches to production. Edited by K. Husnu Can Baser and Gerhard Buchbauer, The Handbook of Essential Oils (CRC Press 2009) discusses production, analysis, storage, transport, toxicology, biological activity, and regulatory issues. It covers biological activity testing, results of antimicrobial and antioxidant tests, and penetration-enhancing activities useful in drug delivery. New information available on essential oils may lead to an increased understanding of their multidimensional uses and better, more ecologically friendly production methods. Their pleasing scent has caused civilizations from ancient to modern to try to capture their essence and stopper it in a pretty bottle. Drug companies will no doubt keep abreast of essential oil and aromatic plant medicine research, hoping to harness this same essence in a different bottle.
(continued from pg. 1)
suggests Dr. Li. “Proper procedures to eliminate adulteration, Because the FDA regulates herbal medicines in the U.S. as contamination, and toxic side effects are also urgently needed dietary supplements rather than drugs, therapeutic claims do to regulate the use of Chinese herbs.” not currently appear on package labels, thereby increasing the likelihood of adverse drug effects and interactions. The Li’s second edition includes valuable data on herbal toxicity Complimentary Alternative Medicine industry is on the brink and contamination, in addition to a constructive comparison of some major changes, including the highly anticipated labelof active ingredients and claimed therapeutic values. With 130 ing guidelines that must be implemented by all supplement new herbs, it is an indispensable resource for those working to manufacturers by June 2010, as directed by the FDA. improve herbal supplement quality and safety standards.
SPECIAL DISCOUNTS FOR THE NATURAL PRODUCTS COMMUNITY! Visit www.crcpress.com and get 15% off the price of any CRC publication when you order online and enter promo code ECH14.
Save even more! Visit the CRC booth at any major conference and get discounts of up to 25%.
Extracting Current Trends from Natural Sources
Celebrating A Banner Year for Natural Product Resources Whether you are a physician looking to expand your treatment protocols, a supplement provider looking to meet new FDA regulations, an organic chemist probing the mysteries of the rain forest, or a molecular biologist tinkering with the structure of a novel pharmaceutical, you can only be as progressive and credible as the information you access.
Natural Pharmacopoeias Help Advance Novel Drug Development When developing new drugs and drug delivery technology, science often looks to nature. Today, medicines from natural sources account for 60 percent of anticancer and anti-infective drugs in use. These complex molecules have evolved over millennia to provide robust, disease-fighting mechanisms. With so many successes garnered from nature, it surprises no one that modern medicine continues to validate many of the traditional uses ascribed to plants and other natural products. When working with plant products, identification and quality control are always crucial issues. Microscopic evaluation of plant material can provide a much-needed quick, accurate, and inexpensive tool for raw material authentication and assessment of purity. A combination handbook and atlas written by Roy Upton, American Herbal Pharmacopoeia: Botanical PharmacognosyMicroscopic Characterization of Botanical Medicines (CRC Press 2009) includes detailed images, drawings, and photomicrographs of sectioned whole and powdered material of important species, many of which had lacked quality descriptions. Upton’s knowledge of ayurvedic, Chinese, and western practices makes him a true renaissance man of this field. He provides full instructions for setting up a microscopy laboratory and performing botanical microscopy for the identification of plant material. The complete repertoire of “Look deep into nature, and then you skills, tools, and techniques of will understand everything better.” pharmacognosy, from physi—Albert Einstein cal to chemical analysis, is critical in the development of new drugs from natural products. Those conducting research need to accurately characterize the products being studied not only to foster experimental reproducibility but also to maintain quality control, regulatory, and pharmacopoeial standards.
Summer 2009
Look it up: Science Supports Alternative Px Whether they are searching for savings or new hope, more than a third of adults now make use of over-the-counter alternative therapies. “This situation increases the need for healthcare professionals, especially pharmacists, to judge the quality of available products and to interpret the products’ role in preventing and treating disease for the lay consumer,” according to Dr. Dennis V.C. Awang, author of Tyler’s Herbs of Choice: The Therapeutic Use of Phytomedicinals, Third Edition (CRC Press 2009). Tyler’s combines the scientific aspects of phytomedicine and pharmacognosy with the modern clinical trials that support the rationale for medicinal use of herbs. Dr. Thomas Li, retired scientist from Agriculture and Agri-Food Canada, is the author of Chinese and Related North American Herbs: Phytopharmacology & Therapeutic Values, Second Edition (CRC Press 2009), which covers more than 1800 species of Chinese herbs and more than 700 related North American species. Amid headlines touting tainted imports, Li reemphasizes the need for stricter regulation and more precise testing. “A basic scientific understanding of the Chinese herbal preparations is the first step toward building consumer confidence in herbal medications,” story continued on pg. 8 (Alternative Px)
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NATURALPRODUCTS Nordic Natural Products Conference Haukadalur, Iceland June 2-5, 2009
CALENDAR Natural Products Networking News
Functional Molecules from Natural Sources A Natural Products Conference Oxford, UK July 6-9, 2009
Society for Industrial Microbiology's (SIM) Annual Meeting and Exhibition Toronto, Ontario, Canada July 26 - 30, 2009
XXII Conference on Advances in Organic Synthesis Karpacz, Poland July 8-12, 2009
Gordon Research Conference on Natural Products Tilton, NH July 26-31, 2009
Special Libraries Association Annual Conference Washington, DC June 14-17, 2009
16th European Symposium on Organic Chemistry (ESOC) Prague, Czech Republic July 12-16, 2009
42nd IUPAC Congress Glasgow, UK August 2-7, 2009
Joint Meeting on Medicinal Chemistry 2009 Budapest, Hungary June 24-27, 2009
Joint Annual Meetings of American Society of Plant Biologists & Phycological Society of America Honolulu, Hawaii July 18-22, 2009
Fapronatura 2009, Second International Symposia about Pharmacology of Natural Products Varadero, Cuba June 3-7, 2009
The 50th Anniversary Meeting of the American Society of Pharmacognosy (ASP) Honolulu, Hawaii June 27 - July 1, 2009
6th European Conference on Marine Natural Products Porto, Portugal July 19-23, 2009
49th Annual Meeting of the Phytochemical Society of North America Biologically Active Phytochemicals Towson University, Maryland August 8-12, 2009 57th International Congress & Annual Meeting of the Society for Medicinal Plant Research Geneva, Switzerland August 16-20, 2009
238th ACS National Meeting & Exposition Fall 2009 Washington, DC, USA August 16-20, 2009 World Congress of Pharmacy and Pharmaceutical Sciences 69th International Congress of FIP Istanbul, Turkey September 3-9, 2009 BPC 2009 British Pharmaceutical Conference Manchester, UK September 6-9, 2009 Asian Federation for Pharmaceutical Science (AFPS) 2009 Fukuoka City, Japan October 15-18, 2009 4th International Conference on Polyphenols and Health Yorkshire, England December 7-11, 2009
A Pro- & Pre-biotic Approach to Bacteria Probiotics and prebiotics alone and together promote gastrointestinal health and proper immune function. Consumption of the proper ratio of probiotics (live microbial food ingredients) and prebiotics (food ingredients that stimulate the growth of good bacteria) can alter the intestinal microflora with significant health benefit. Recent research demonstrates great potential in the treatment of specific diseases, especially inflammatory bowel disease (IBD). In addition to the elimination of pathogenic bacteria, the mechanisms credited to these agents include increased SCFA production, reduction of inflammatory cytokine secretion, strengthening of the intestinal epithelial wall, and improvement of Th1/Th2 balance. Similarly, their use is being studied for the prevention of colorectal cancers. Evidence supports the notion that supplemental use can change colon pH, alter gut xenobiotic metabolism, and modulate the immune system.
2
The Good, The Bad, and The Viable The use of pro- and prebiotics as well as synbiotics (their therapeutic combination) also holds promise for improved infant formulas, cholesterol regulation, and treatments for lactose intolerance and diabetes. They can also be used to replace the good bacteria that is inadvertently destroyed by non-discriminating antibiotics. The commercial challenge is to create quality products that lend themselves to processing, packaging, and distribution. The Handbook of Prebiotics and Probiotics Ingredients: Health Benefits and Food Applications (CRC Press 2009) explores these variables and highlights current biological research and food applications. Chapters contributed by experts from around the world take a global perspective, providing a thorough reference for product developers and regulatory agencies as well as for nutritionists and forwardthinking health professionals.
NATURALPRODUCTS
PIONEERS Noteworthy Names in Natural Products
The Ah-ha Moments of Carotenoid Research Excerpted from an interview with John Landrum, Florida International University, Miami, USA, editor of the forthcoming Carotenoids: Physical, Chemical, and Biological Functions and Properties.
The Many Faces of Carotenoids While many people know of !-carotene … they are rarely aware that it is but a single representative from among over 700 identified carotenoids, all of which are essential to at least one organism. Possibly as many as 50 of these are present in the human diet but perhaps no more than a dozen are actually absorbed into bloodstream. Of these, the non-provitamin A carotenoids lutein, zeaxanthin, and lycopene are the most abundant and we are now learning that they may each play very critical roles in the protection against prostate cancer (lycopene), reduction of the risk for atherosclerosis (lycopene, lutein) and reduction of the risk for age-related macular degeneration (lutein and zeaxanthin). Unquestionably, the most exciting discovery within the carotenoid field in recent years, the cloning of the enzyme responsible for the conversion of !-carotene to vitamin A, has come about in the use of modern cell biology and PCR techniques. The related discovery that lycopene is also cleaved specifically by the carotenoid cleavage enzyme has the potential to open windows upon the nature of how carotenoids influence cell proliferation and apoptosis.
… we recognized that we were investigating something very unique. Understanding the factors and mechanisms that control absorption of carotenoids by cells is crucial to our developing ability to provide nutritionists and others with the tools essential to effectively modify diets and improve the health in populations around the world.
A Number of Quiet Discoveries My own research has been largely a study of the identity, absorption, and localization of the carotenoids lutein and zeaxanthin, which are the principal components of the macular pigment. This work, as so often is the case in science, has never been characterized by the realization that accompanies being struck by lightning. Rather our understanding and recognition that these non-pro-vitamin A carotenoids have a critical importance to maintaining ocular health arose from a number of quiet discoveries.
Our initial HPLC investigation and characterization of the minor and obscure yellow spot in found in the macula resulted in the discovery that it was composed of two, and only two, of the common xanthophylls found in human blood. The fact that the most common carotenoids in the human diet and blood, !-carotene and lycopene, were absent only really impressed us as we became aware of how unique the retina was in this respect; in virtually every other tissue of the human body the carotenoids are present in amounts and proportions not vastly different from that in serum. When a further investigation involving the measurement of the ratio of the carotenoids revealed that the proportions of lutein and zeaxanthin varied across the retina in a systematic fashion, the puzzling nature of the accumulation of these two carotenoids within the retina became more compelling. This study demonstrated to us that the processes of carotenoid accumulation in the retina was under careful biochemical regulation and must involve proteins capable of specifically recognizing, binding, and transporting these otherwise almost indistinguishable carotenoids. … we recognized that we were investigating something very unique. Later, we discovered that metabolism of carotenoids was occurring within the retina and that this produced a relatively uncommon isomer of zeaxanthin that is not present in the diet of most people. …we were able to provide definitive evidence that dietary manipulation of the quantity of the carotenoids in the retina could be achieved by consuming supplements of these carotenoids. Our ah-hah moments in this scientific research are sometimes hard to define but the retrospective view that, step by step we have been able to open up new vistas as we have studied the different aspects of the macular carotenoids is unmistakable.
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NATURALPRODUCTS
PARTNERS in PUBLISHING
Synthesizing today’s research for tomorrow’s discoveries
Dictionary of Alkaloids
(continued from pg. 3)
is inspected and the great majority are updated. The extensive introduction is completely rewritten and expanded. For this purpose, we have been lucky to secure the participation of Professor Laszlo Szabo. A renowned expert on the indole alkaloids and their biosynthesis, Professor Szabo has completely revamped the presentation and classification of this largest and most complex class of alkaloids. Reflecting changes in the literature, some notable shifts in emphasis are evident in the new edition. Thanks to the work of the Battersby group and others, as of 1989, the structures and biosynthesis of the main types of terrestrial alkaloid — those made especially by higher plants — has been worked out. The main areas of new information have concerned novel and improved synthetic methods (notably from the Nicolaou group, among others), and the isolation of new alkaloids of unprecedented structure from a variety of organisms, some of them resulting from the participation of newly recognized enzyme types, such as the Diels-Alder enzymes. We also know much more about the interrelatedness of ecosystems and the way in which alkaloids and other metabolites may be passed to and metabolized by predators; for example, the toxic pyrrolizidine alkaloids from plants can become part of a butterfly’s defense mechanism.
The Best of Both Worlds: No Choice Required An important feature of the dictionary and of the database in general has always been its classification scheme for Type of Compound. These codes are designed to complement substructure searching. Each heading merges all of the alkaloids thought by specialists to be biogenetically related, even those that don’t share the same carbon skeleton. The newly discovered types of alkaloid have pushed the classification scheme hard, necessitating the insertion of numerous new categories in an attempt to limit as much as possible the number of alkaloids remaining under miscellaneous codes. Not many resources offer both remarkable information and the luxury of choice. Some will prefer the sophisticated and user-friendly search possibilities offered by the electronic version, and others will prefer to thumb through the pages of the highly browsable print version. Either way, one will find access to data unparalleled in both scope and depth. The newest edition will be available in the fall of this year.
6
CHEMnetBASE 2009 10 Years of Service to the Chemistry Community
NATURALPRODUCTS
RootS Extracting Current Trends from Natural Sources
New Dictionary of Alkaloids Raises the Bar John Buckingham
Heralded in reviews as a powerful and welcome site for all chemists when it premiered in 1999, CHEMnetBASE pioneered a way to keep pace with the-never-ending data explosion of modern science. It now incorporates a core of chemical dictionaries from Chapman & Hall/CRC, including:
This fall brings publication of a new edition of the Dictionary of Alkaloids, put together by a team of subject specialists known for their work on the Chapman & Hall/CRC Dictionary of Natural Products. This new edition represents the cumulated effort of more than 25 years of compilation and editing and includes the input of a number of well-respected alkaloid chemists.
Following the successful publication of DOC5, a number of specialized dictionaries were planned building on the technology of the DOC. One of the first of these publications was the Dictionary of Alkaloids (by this author and Ian W. Southon) in 1988. The number of alkaloids then known was approximately 10,000.
• Combined Chemical Dictionary
A Brief History of Data
• Dictionary of Natural Products
Before going further, it is worth casting a brief eye over the remarkable history of the entire Chapman & Hall database project, which has led to the production of a number of specialized dictionaries, including the Dictionary of Alkaloids. The C&H database (or more strictly, databank) was established in the late 1970s as a means of updating and bringing out a new edition of the Dictionary of Organic Compounds. Known as the DOC, dating back to the 1930s, it had been around in print form through four successive editions. The DOC provided a popular alternative to Beilstein. In addition to being less expensive than Beilstein, it provided easier access as well as more current data on frequently accessed organic compounds.
The 1990s led to two further developments of note. First, the compilation on a comprehensive basis of further classes of natural products led to the eventual emergence of the Dictionary of Natural Products (1993), now recognized as the leading information source on all classes of metabolites. Secondly, the dictionaries migrated from print to substructure-searchable electronic venues. Initially offered on CDROM, the dictionaries are now available in DVD and web versions; DOC6 in 1995 was the last print edition.
• Handbook of Chemistry & Physics Today, CHEMnetBASE provides structure-searchable access to the properties and characteristics of more than 500,000 compounds, as well as almost all known natural products and polymers. To find out more, visit www.chemnetbase.com. Free trials are available for qualifying institutions.
Taylor & Francis Journals
The Chosen Forum for New Discoveries for 250 Years Available in print and online, Taylor & Francis journals provide visibility and access to cutting-edge research as well as the opportunity for scientists to have their work peerreviewed and published.
Pharmaceutical Biology covers discovery, description, analysis characterization, and production/isolation of biologically active chemicals, as well as other substances, drugs, pharmaceutical products, or preparations utilized in systems of traditional medicine. Edited by John M. Pezzuto, professor and dean at the College of Pharmacy in Hilo, Hawaii, the journal accepts manuscripts that meet the criteria of scientific rigor and possess the potential to advance the field. For more information visit www.informaworld.com
A Leap of Faith – A Technically Sound Landing The DOC played a major role in the reporting of new natural products. But by the 1970s, it was becoming impossible for this traditional print product to keep pace with the rapid development of new compounds, new syntheses, and other important updates. As a result, the C&H database was conceived. It presented a highly re-edited version of the printed DOC with massive updating drawn from the recent literature. At the time, the only competing product in the field was Chemical Abstracts. Incorporating direct phototypesetting, the DOC database represented a great technological leap forward. With the help of the Mack Printing Corporation of Easton, Pennsylvania, the pioneering highquality fifth edition of the DOC became the reference of choice.
The 90s: Going Electronic
Currently, the two flagship Chapman & Hall/CRC products are DNP and the Combined Chemical Dictionary, which incorporates organic compounds as well as inorganics, drugs, and other datasets. Each of the electronic dictionaries is updated on six month cycles. More recently, we have begun to produce a fresh series of printed publications drawn from the database. The new Dictionary of Alkaloids is part of that effort. Satisfying diverse needs, each new edition will include a substructure-searchable DVD along with the printed book.
20,000 Alkaloids and Counting A wide definition of alkaloid has been used in the dictionary, so that, for example, non-basic alkaloidal amides are comprehensively covered. The growth of natural product information is evidenced by the fact that the number of alkaloids documented in the new edition is now more than doubled to over 20,000. Despite the increase in entries, a more compact format makes it possible to squeeze all of the data into a single volume. While restrictions limit the amount of indexing in the print volume, extensive indexing is present in the electronic version. For this new edition, every existing entry story continued on pg. 6 (Dictionary of Alkaloids)
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NATURALPRODUCTS Recently Published and Upcoming Titles Carotenoids
Call for Authors
Dictionary of Alkaloids
Second Edition with CD-ROM John Buckingham
Consultant Editor, Dictionary of Natural Products, London
Edited by
Consultants, UK
Florida International University, Miami, Florida, USA
Catalog no. 52306, November 2009 c. 528 pp., ISBN: 978-1-4200-5230-5 $189.95 / £121.00
The cross-fertilization of classical pharmacognosy with modern chemical and biological approaches continues to keep the pharmacognosy field relevant for those working in both drug development and herbal medicines. To meet the demand for relevant resources, CRC Press is initiating a book series in Clinical Pharmacognosy. Potential target areas include pharmacognosy as it relates to women’s health, infectious diseases, oxidative stress, neurodegenerative diseases, aging, and/or mental health disorders and addiction.
Edited by
Physical, Chemical, and Biological Functions and Properties John T. Landrum
NATURALPRODUCTS
Extracting Current Trends from Natural Sources
Keith Baggaley and Andy Roberts Laszlo F. Szabo
Semmelweis University, Budapest, Hungary
Catalog no. 77694, October 2009, c. 2200 pp. ISBN: 978-1-4200-7769-8, $695.00 / £442.00
Send all queries to the Series or Acquiring editor. Series Editor Professor Navindra Seeram Bioactive Botanical Research Laboratory Department of Biomedical and Pharmaceutical Sciences 41 Lower College Road, College of Pharmacy, University of Rhode Island, Kingston, RI 02881 nseeram@mail.uri.edu Acquiring Editor Hilary Rowe CRC Press/Taylor and Francis 6000 Broken Sound Parkway NW Suite 300 Boca Raton, FL 33487 Hilary.rowe@taylorandfrancis.com 858 436 5501
Chinese & Related North American Herbs
Figs Edited by
Ephraim Philip Lansky
Rimonest Ltd., Haifa, Israel
Helena Maaria Paavilainen Series: Medicinal and Aromatic Plants - Industrial Profiles
Catalog no. 89668, November 2009 c. 450 pp., ISBN: 978-1-4200-8966-0 $129.95 / £82.00
Handbook of Nutraceuticals Ingredients, Formulations, and Applications Edited by
Yashwant Pathak
Sullivan University, Louisville, Kentucky, USA
Catalog no. 82213, November 2009 c. 416 pp., ISBN: 978-1-4200-8221-0 $149.95 / £89.00
American Herbal Pharmacopoeia Botanical Pharmacognosy-Microscopic Characterization of Botanical Medicines
Phytopharmacology & Therapeutic Values, Second Edition Thomas S. C. Li
Penticton, British Columbia, Canada
Catalog no. 94157, September 2009 c. 560 pp., ISBN: 978-1-4200-9415-2 $189.95 / £121.00
Handbook of Essential Oils
Science, Technology, and Applications K. Husnu Can Baser
Anadolu University, Eskisehir, Turkey
Gerhard Buchbauer
Universitat Wien, Austria
Catalog no. 63154, September 2009 c. 656 pp., ISBN: 978-1-4200-6315-8 $189.95 / £121.00
Tyler's Herbs of Choice
Essential Oil Bearing Grasses
MediPlant Consulting, Inc., White Rock, British Columbia, Canada
The Therapeutic Use of Phytomedicinals, Third Edition
The genus Cymbopogon Edited by
Anand Akhila
American Herbal Pharmacopoeia, Scotts Valley, California, USA
Central Institute of Medicinal & Aromatic Plants, Lucknow, India Series: Medicinal and Aromatic Plants - Industrial Profiles, Vol. 46
Catalog no. 73265, October 2009, c. 512 pp. ISBN: 978-1-4200-7326-3, $169.95 / £108.00
Catalog no. 7857, August 2009, c. 296 pp. ISBN: 978-0-8493-7857-7, $139.95 / £89.00
Plant Gum Exudates of the World
Handbook of Prebiotics and Probiotics Ingredients
Edited by
Roy Upton
Sources, Distribution, Properties, and Applications
Dennis V.C. Awang
International Poisonous Plants Checklist An Evidence-Based Reference D. Jesse Wagstaff
United States Food and Drug Administration (Emeritus)
Catalog no. 28093, May 2009, 296 pp. ISBN: 978-0-7890-2809-9, $89.95 / £54.99
Catalog no. 62522, January 2009, 464 pp. ISBN: 978-1-4200-6252-6, $149.95 / £95.00
Duke's Handbook of Medicinal Plants of Latin America
Marine Products for Healthcare
Green Farmacy Garden, Fulton, Maryland, USA
Vazhiyil Venugopal
James A. Duke
Functional and Bioactive Nutraceutical Compounds from the Ocean
Catalog no. 43161, January 2009, 832 pp. ISBN: 978-1-4200-4316-7, $119.95 / £76.99
Indian Institute of Technology, Mumbai Series: Functional Foods and Nutraceuticals
Health Benefits and Food Applications
Handbook of Plant-Based Biofuels
Catalog no. 52632, January 2009, 528 pp. ISBN: 978-1-4200-5263-3, $169.95 / £108.00
Tea and Tea Products
Edited by
Edited by
Amos Nussinovitch
Susan Sungsoo Cho
Ashok Pandey
Catalog no. 52233, October 2009, c. 352 pp. ISBN: 978-1-4200-5223-7, $179.95 / £114.00
Terry Finocchiaro Catalog no. 62131, August 2009, c. 416 pp. ISBN: 978-1-4200-6213-7, $159.95 / £99.00
Catalog no. 21755, January 2009, 312 pp. ISBN: 978-1-56022-175-3, $119.95 / £76.99
Chi-Tang Ho
National Taiwan University, Taipei
Edited by
High-Throughput Analysis in the Pharmaceutical Industry
Renata Pasqualini and Wadih Arap
Edited by
The Hebrew University of Jerusalem, Rehovot, Israel
Science of Chinese Materia Medica Edited by
Difeng Zhang
Jiangxi University of Traditional Chinese Medicine, China
Catalog no. 90801, October 2009, c. 507 pp. ISBN: 978-1-4200-9080-2, $129.95 / £78.99
4
NutraSource Inc., Laurel, Maryland, USA
Protein Discovery Technologies
Chemistry and Health-Promoting Properties
National Institute for Interdisciplinary Science and Technology, Tribandrum, India
Edited by
University of Texas, M.D. Anderson Cancer Center, Houston, USA Drug Discovery Series, Vol. 12
Perry G. Wang
Catalog no. DK2081, July 2009, c. 208 pp. ISBN: 978-0-8247-5468-6, $149.95 / £95.00
Catalog no. 5953X, January 2009, 432 pp. ISBN: 978-1-4200-5953-3, $159.95 / £99.00
Order online at
Jen-Kun Lin
Fereidoon Shahidi
Memorial University of Newfoundland, Canada Series: Nutraceutical Science and Technology, Vol. 8
Catalog no. 8082, January 2009, 320 pp. ISBN: 978-0-8493-8082-2, $149.95 / £95.00
Teleflex, Wyomissing, Philadelphia, USA Series: Critical Reviews in Combinatorial Chemistry
www.crcpress.com
Rutgers University, New Brunswick, New Jersey, USA
•
Chemistry and Molecular Aspects of Drug Design and Action Edited by
E.A. Rekka and P.N. Kourounakis
Aristotelian University of Thessaloniki, Greece
Catalog no. 9006, 2008, 384 pp. ISBN: 978-0-8493-9006-7, $179.95 / £114.00
Phytochemicals Aging and Health Edited by
Mark S. Meskin and Wayne R. Bidlack
California State Polytechnic University, Pomona, USA
R. Keith Randolph
Access Business Group, Ada, Michigan, USA
Catalog no. 61372, 2008, 232 pp. ISBN: 978-1-4200-6137-6, $129.95 / £82.00
Thin Layer Chromatography in Phytochemistry Edited by
Monika Waksmundzka-Hajnos and Monika Waksmundzka-Hajnos Medical University of Lublin, Poland
Joseph Sherma
Lafayette College, Easton, Pennsylvania, USA
Teresa Kowalska
University of Silesia, Katowice, Poland Chromatographic Science Series
Catalog no. 46772, 2008, 896 pp. ISBN: 978-1-4200-4677-9, $199.95 / £127.00
Enter promo code ECH14 and
Save 15%.
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NATURALPRODUCTS
PARTNERS in PUBLISHING
Synthesizing today’s research for tomorrow’s discoveries
Dictionary of Alkaloids
(continued from pg. 3)
is inspected and the great majority are updated. The extensive introduction is completely rewritten and expanded. For this purpose, we have been lucky to secure the participation of Professor Laszlo Szabo. A renowned expert on the indole alkaloids and their biosynthesis, Professor Szabo has completely revamped the presentation and classification of this largest and most complex class of alkaloids. Reflecting changes in the literature, some notable shifts in emphasis are evident in the new edition. Thanks to the work of the Battersby group and others, as of 1989, the structures and biosynthesis of the main types of terrestrial alkaloid — those made especially by higher plants — has been worked out. The main areas of new information have concerned novel and improved synthetic methods (notably from the Nicolaou group, among others), and the isolation of new alkaloids of unprecedented structure from a variety of organisms, some of them resulting from the participation of newly recognized enzyme types, such as the Diels-Alder enzymes. We also know much more about the interrelatedness of ecosystems and the way in which alkaloids and other metabolites may be passed to and metabolized by predators; for example, the toxic pyrrolizidine alkaloids from plants can become part of a butterfly’s defense mechanism.
The Best of Both Worlds: No Choice Required An important feature of the dictionary and of the database in general has always been its classification scheme for Type of Compound. These codes are designed to complement substructure searching. Each heading merges all of the alkaloids thought by specialists to be biogenetically related, even those that don’t share the same carbon skeleton. The newly discovered types of alkaloid have pushed the classification scheme hard, necessitating the insertion of numerous new categories in an attempt to limit as much as possible the number of alkaloids remaining under miscellaneous codes. Not many resources offer both remarkable information and the luxury of choice. Some will prefer the sophisticated and user-friendly search possibilities offered by the electronic version, and others will prefer to thumb through the pages of the highly browsable print version. Either way, one will find access to data unparalleled in both scope and depth. The newest edition will be available in the fall of this year.
6
CHEMnetBASE 2009 10 Years of Service to the Chemistry Community
NATURALPRODUCTS
RootS Extracting Current Trends from Natural Sources
New Dictionary of Alkaloids Raises the Bar John Buckingham
Heralded in reviews as a powerful and welcome site for all chemists when it premiered in 1999, CHEMnetBASE pioneered a way to keep pace with the-never-ending data explosion of modern science. It now incorporates a core of chemical dictionaries from Chapman & Hall/CRC, including:
This fall brings publication of a new edition of the Dictionary of Alkaloids, put together by a team of subject specialists known for their work on the Chapman & Hall/CRC Dictionary of Natural Products. This new edition represents the cumulated effort of more than 25 years of compilation and editing and includes the input of a number of well-respected alkaloid chemists.
Following the successful publication of DOC5, a number of specialized dictionaries were planned building on the technology of the DOC. One of the first of these publications was the Dictionary of Alkaloids (by this author and Ian W. Southon) in 1988. The number of alkaloids then known was approximately 10,000.
• Combined Chemical Dictionary
A Brief History of Data
• Dictionary of Natural Products
Before going further, it is worth casting a brief eye over the remarkable history of the entire Chapman & Hall database project, which has led to the production of a number of specialized dictionaries, including the Dictionary of Alkaloids. The C&H database (or more strictly, databank) was established in the late 1970s as a means of updating and bringing out a new edition of the Dictionary of Organic Compounds. Known as the DOC, dating back to the 1930s, it had been around in print form through four successive editions. The DOC provided a popular alternative to Beilstein. In addition to being less expensive than Beilstein, it provided easier access as well as more current data on frequently accessed organic compounds.
The 1990s led to two further developments of note. First, the compilation on a comprehensive basis of further classes of natural products led to the eventual emergence of the Dictionary of Natural Products (1993), now recognized as the leading information source on all classes of metabolites. Secondly, the dictionaries migrated from print to substructure-searchable electronic venues. Initially offered on CDROM, the dictionaries are now available in DVD and web versions; DOC6 in 1995 was the last print edition.
• Handbook of Chemistry & Physics Today, CHEMnetBASE provides structure-searchable access to the properties and characteristics of more than 500,000 compounds, as well as almost all known natural products and polymers. To find out more, visit www.chemnetbase.com. Free trials are available for qualifying institutions.
Taylor & Francis Journals
The Chosen Forum for New Discoveries for 250 Years Available in print and online, Taylor & Francis journals provide visibility and access to cutting-edge research as well as the opportunity for scientists to have their work peerreviewed and published.
Pharmaceutical Biology covers discovery, description, analysis characterization, and production/isolation of biologically active chemicals, as well as other substances, drugs, pharmaceutical products, or preparations utilized in systems of traditional medicine. Edited by John M. Pezzuto, professor and dean at the College of Pharmacy in Hilo, Hawaii, the journal accepts manuscripts that meet the criteria of scientific rigor and possess the potential to advance the field. For more information visit www.informaworld.com
A Leap of Faith – A Technically Sound Landing The DOC played a major role in the reporting of new natural products. But by the 1970s, it was becoming impossible for this traditional print product to keep pace with the rapid development of new compounds, new syntheses, and other important updates. As a result, the C&H database was conceived. It presented a highly re-edited version of the printed DOC with massive updating drawn from the recent literature. At the time, the only competing product in the field was Chemical Abstracts. Incorporating direct phototypesetting, the DOC database represented a great technological leap forward. With the help of the Mack Printing Corporation of Easton, Pennsylvania, the pioneering highquality fifth edition of the DOC became the reference of choice.
The 90s: Going Electronic
Currently, the two flagship Chapman & Hall/CRC products are DNP and the Combined Chemical Dictionary, which incorporates organic compounds as well as inorganics, drugs, and other datasets. Each of the electronic dictionaries is updated on six month cycles. More recently, we have begun to produce a fresh series of printed publications drawn from the database. The new Dictionary of Alkaloids is part of that effort. Satisfying diverse needs, each new edition will include a substructure-searchable DVD along with the printed book.
20,000 Alkaloids and Counting A wide definition of alkaloid has been used in the dictionary, so that, for example, non-basic alkaloidal amides are comprehensively covered. The growth of natural product information is evidenced by the fact that the number of alkaloids documented in the new edition is now more than doubled to over 20,000. Despite the increase in entries, a more compact format makes it possible to squeeze all of the data into a single volume. While restrictions limit the amount of indexing in the print volume, extensive indexing is present in the electronic version. For this new edition, every existing entry story continued on pg. 6 (Dictionary of Alkaloids)
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NATURALPRODUCTS Nordic Natural Products Conference Haukadalur, Iceland June 2-5, 2009
CALENDAR Natural Products Networking News
Functional Molecules from Natural Sources A Natural Products Conference Oxford, UK July 6-9, 2009
Society for Industrial Microbiology's (SIM) Annual Meeting and Exhibition Toronto, Ontario, Canada July 26 - 30, 2009
XXII Conference on Advances in Organic Synthesis Karpacz, Poland July 8-12, 2009
Gordon Research Conference on Natural Products Tilton, NH July 26-31, 2009
Special Libraries Association Annual Conference Washington, DC June 14-17, 2009
16th European Symposium on Organic Chemistry (ESOC) Prague, Czech Republic July 12-16, 2009
42nd IUPAC Congress Glasgow, UK August 2-7, 2009
Joint Meeting on Medicinal Chemistry 2009 Budapest, Hungary June 24-27, 2009
Joint Annual Meetings of American Society of Plant Biologists & Phycological Society of America Honolulu, Hawaii July 18-22, 2009
Fapronatura 2009, Second International Symposia about Pharmacology of Natural Products Varadero, Cuba June 3-7, 2009
The 50th Anniversary Meeting of the American Society of Pharmacognosy (ASP) Honolulu, Hawaii June 27 - July 1, 2009
6th European Conference on Marine Natural Products Porto, Portugal July 19-23, 2009
49th Annual Meeting of the Phytochemical Society of North America Biologically Active Phytochemicals Towson University, Maryland August 8-12, 2009 57th International Congress & Annual Meeting of the Society for Medicinal Plant Research Geneva, Switzerland August 16-20, 2009
238th ACS National Meeting & Exposition Fall 2009 Washington, DC, USA August 16-20, 2009 World Congress of Pharmacy and Pharmaceutical Sciences 69th International Congress of FIP Istanbul, Turkey September 3-9, 2009 BPC 2009 British Pharmaceutical Conference Manchester, UK September 6-9, 2009 Asian Federation for Pharmaceutical Science (AFPS) 2009 Fukuoka City, Japan October 15-18, 2009 4th International Conference on Polyphenols and Health Yorkshire, England December 7-11, 2009
A Pro- & Pre-biotic Approach to Bacteria Probiotics and prebiotics alone and together promote gastrointestinal health and proper immune function. Consumption of the proper ratio of probiotics (live microbial food ingredients) and prebiotics (food ingredients that stimulate the growth of good bacteria) can alter the intestinal microflora with significant health benefit. Recent research demonstrates great potential in the treatment of specific diseases, especially inflammatory bowel disease (IBD). In addition to the elimination of pathogenic bacteria, the mechanisms credited to these agents include increased SCFA production, reduction of inflammatory cytokine secretion, strengthening of the intestinal epithelial wall, and improvement of Th1/Th2 balance. Similarly, their use is being studied for the prevention of colorectal cancers. Evidence supports the notion that supplemental use can change colon pH, alter gut xenobiotic metabolism, and modulate the immune system.
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The Good, The Bad, and The Viable The use of pro- and prebiotics as well as synbiotics (their therapeutic combination) also holds promise for improved infant formulas, cholesterol regulation, and treatments for lactose intolerance and diabetes. They can also be used to replace the good bacteria that is inadvertently destroyed by non-discriminating antibiotics. The commercial challenge is to create quality products that lend themselves to processing, packaging, and distribution. The Handbook of Prebiotics and Probiotics Ingredients: Health Benefits and Food Applications (CRC Press 2009) explores these variables and highlights current biological research and food applications. Chapters contributed by experts from around the world take a global perspective, providing a thorough reference for product developers and regulatory agencies as well as for nutritionists and forwardthinking health professionals.
NATURALPRODUCTS
PIONEERS Noteworthy Names in Natural Products
The Ah-ha Moments of Carotenoid Research Excerpted from an interview with John Landrum, Florida International University, Miami, USA, editor of the forthcoming Carotenoids: Physical, Chemical, and Biological Functions and Properties.
The Many Faces of Carotenoids While many people know of !-carotene … they are rarely aware that it is but a single representative from among over 700 identified carotenoids, all of which are essential to at least one organism. Possibly as many as 50 of these are present in the human diet but perhaps no more than a dozen are actually absorbed into bloodstream. Of these, the non-provitamin A carotenoids lutein, zeaxanthin, and lycopene are the most abundant and we are now learning that they may each play very critical roles in the protection against prostate cancer (lycopene), reduction of the risk for atherosclerosis (lycopene, lutein) and reduction of the risk for age-related macular degeneration (lutein and zeaxanthin). Unquestionably, the most exciting discovery within the carotenoid field in recent years, the cloning of the enzyme responsible for the conversion of !-carotene to vitamin A, has come about in the use of modern cell biology and PCR techniques. The related discovery that lycopene is also cleaved specifically by the carotenoid cleavage enzyme has the potential to open windows upon the nature of how carotenoids influence cell proliferation and apoptosis.
… we recognized that we were investigating something very unique. Understanding the factors and mechanisms that control absorption of carotenoids by cells is crucial to our developing ability to provide nutritionists and others with the tools essential to effectively modify diets and improve the health in populations around the world.
A Number of Quiet Discoveries My own research has been largely a study of the identity, absorption, and localization of the carotenoids lutein and zeaxanthin, which are the principal components of the macular pigment. This work, as so often is the case in science, has never been characterized by the realization that accompanies being struck by lightning. Rather our understanding and recognition that these non-pro-vitamin A carotenoids have a critical importance to maintaining ocular health arose from a number of quiet discoveries.
Our initial HPLC investigation and characterization of the minor and obscure yellow spot in found in the macula resulted in the discovery that it was composed of two, and only two, of the common xanthophylls found in human blood. The fact that the most common carotenoids in the human diet and blood, !-carotene and lycopene, were absent only really impressed us as we became aware of how unique the retina was in this respect; in virtually every other tissue of the human body the carotenoids are present in amounts and proportions not vastly different from that in serum. When a further investigation involving the measurement of the ratio of the carotenoids revealed that the proportions of lutein and zeaxanthin varied across the retina in a systematic fashion, the puzzling nature of the accumulation of these two carotenoids within the retina became more compelling. This study demonstrated to us that the processes of carotenoid accumulation in the retina was under careful biochemical regulation and must involve proteins capable of specifically recognizing, binding, and transporting these otherwise almost indistinguishable carotenoids. … we recognized that we were investigating something very unique. Later, we discovered that metabolism of carotenoids was occurring within the retina and that this produced a relatively uncommon isomer of zeaxanthin that is not present in the diet of most people. …we were able to provide definitive evidence that dietary manipulation of the quantity of the carotenoids in the retina could be achieved by consuming supplements of these carotenoids. Our ah-hah moments in this scientific research are sometimes hard to define but the retrospective view that, step by step we have been able to open up new vistas as we have studied the different aspects of the macular carotenoids is unmistakable.
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NATURALPRODUCTS
NEXUS
New Research Brings Essential Oils Back to the Future Extracted from the flowers, seeds, leaves, stems, bark, and roots, essential oils can be considered the soul of the plant. According to ancient Egyptian hieroglyphics and Chinese manuscripts, priests and alchemists used them not only in religious ritual but also to heal the sick. Some sealed flasks discovered in King Tutankhamun’s tomb contained an unguent that, after 3300 years, still had a perceptible odor. Subsequent analysis revealed the presence of frankincense and spikenard, making this, perhaps, the only surviving bottle of the world's first perfume. Ayurvedic literature as early as 2000 B.C. records Indian doctors administering oils to their patients. The ancient Greeks employed them cosmetically and medicinally and the Romans bathed with them several times a day, using them to scent the hair, the body, and even the bed. Today, society looks to science to document health choices and the oils do not disappoint. Recent studies have shown the usefulness of the terpenes found in essential oils for chemoprevention, treating atherosclerosis and thrombosis, and skin penetration enhancers for transdermal drug delivery as well as for antibacterial, antimicrobial, antidiabetic, and antiviral agents. Promising research has revealed that some essential oils kill methicillin-resistant Staphylococcus aureus, E. coli, and other bacteria and fungi within two minutes of contact. The key to this effectiveness lies in their makeup — a complex mixture of chemical compounds that the MRSA and other super bugs find difficult to resist.
Alternative Px
Best Practices and Quality Control Come to Age The growing body of evidence suggesting efficacy for more than just scenting a room underscores the need for production standards, quality control parameters for raw materials and finished products, and well-defined Good Manufacturing Practices. In Essential Oil Bearing Grasses: The genus Cymbopogon (CRC Press 2009) Anand Akhila brings together a team of experts to define best practices from harvest to postharvest and extraction. They discuss analytical methods for identifying terpenes and developments in biotechnological approaches to production. Edited by K. Husnu Can Baser and Gerhard Buchbauer, The Handbook of Essential Oils (CRC Press 2009) discusses production, analysis, storage, transport, toxicology, biological activity, and regulatory issues. It covers biological activity testing, results of antimicrobial and antioxidant tests, and penetration-enhancing activities useful in drug delivery. New information available on essential oils may lead to an increased understanding of their multidimensional uses and better, more ecologically friendly production methods. Their pleasing scent has caused civilizations from ancient to modern to try to capture their essence and stopper it in a pretty bottle. Drug companies will no doubt keep abreast of essential oil and aromatic plant medicine research, hoping to harness this same essence in a different bottle.
(continued from pg. 1)
suggests Dr. Li. “Proper procedures to eliminate adulteration, Because the FDA regulates herbal medicines in the U.S. as contamination, and toxic side effects are also urgently needed dietary supplements rather than drugs, therapeutic claims do to regulate the use of Chinese herbs.” not currently appear on package labels, thereby increasing the likelihood of adverse drug effects and interactions. The Li’s second edition includes valuable data on herbal toxicity Complimentary Alternative Medicine industry is on the brink and contamination, in addition to a constructive comparison of some major changes, including the highly anticipated labelof active ingredients and claimed therapeutic values. With 130 ing guidelines that must be implemented by all supplement new herbs, it is an indispensable resource for those working to manufacturers by June 2010, as directed by the FDA. improve herbal supplement quality and safety standards.
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Extracting Current Trends from Natural Sources
Celebrating A Banner Year for Natural Product Resources Whether you are a physician looking to expand your treatment protocols, a supplement provider looking to meet new FDA regulations, an organic chemist probing the mysteries of the rain forest, or a molecular biologist tinkering with the structure of a novel pharmaceutical, you can only be as progressive and credible as the information you access.
Natural Pharmacopoeias Help Advance Novel Drug Development When developing new drugs and drug delivery technology, science often looks to nature. Today, medicines from natural sources account for 60 percent of anticancer and anti-infective drugs in use. These complex molecules have evolved over millennia to provide robust, disease-fighting mechanisms. With so many successes garnered from nature, it surprises no one that modern medicine continues to validate many of the traditional uses ascribed to plants and other natural products. When working with plant products, identification and quality control are always crucial issues. Microscopic evaluation of plant material can provide a much-needed quick, accurate, and inexpensive tool for raw material authentication and assessment of purity. A combination handbook and atlas written by Roy Upton, American Herbal Pharmacopoeia: Botanical PharmacognosyMicroscopic Characterization of Botanical Medicines (CRC Press 2009) includes detailed images, drawings, and photomicrographs of sectioned whole and powdered material of important species, many of which had lacked quality descriptions. Upton’s knowledge of ayurvedic, Chinese, and western practices makes him a true renaissance man of this field. He provides full instructions for setting up a microscopy laboratory and performing botanical microscopy for the identification of plant material. The complete repertoire of “Look deep into nature, and then you skills, tools, and techniques of will understand everything better.” pharmacognosy, from physi—Albert Einstein cal to chemical analysis, is critical in the development of new drugs from natural products. Those conducting research need to accurately characterize the products being studied not only to foster experimental reproducibility but also to maintain quality control, regulatory, and pharmacopoeial standards.
Summer 2009
Look it up: Science Supports Alternative Px Whether they are searching for savings or new hope, more than a third of adults now make use of over-the-counter alternative therapies. “This situation increases the need for healthcare professionals, especially pharmacists, to judge the quality of available products and to interpret the products’ role in preventing and treating disease for the lay consumer,” according to Dr. Dennis V.C. Awang, author of Tyler’s Herbs of Choice: The Therapeutic Use of Phytomedicinals, Third Edition (CRC Press 2009). Tyler’s combines the scientific aspects of phytomedicine and pharmacognosy with the modern clinical trials that support the rationale for medicinal use of herbs. Dr. Thomas Li, retired scientist from Agriculture and Agri-Food Canada, is the author of Chinese and Related North American Herbs: Phytopharmacology & Therapeutic Values, Second Edition (CRC Press 2009), which covers more than 1800 species of Chinese herbs and more than 700 related North American species. Amid headlines touting tainted imports, Li reemphasizes the need for stricter regulation and more precise testing. “A basic scientific understanding of the Chinese herbal preparations is the first step toward building consumer confidence in herbal medications,” story continued on pg. 8 (Alternative Px)