Recent Advances in Phytochemistry – serie

The past decade has seen major advances in the cloning of genes encoding enzymes of plant secondary metabolism. This has been further enhanced by the recent project on the sequencing of the Arabidopsis genome. These developments provide the molecular genetic basis to address the question of the Evolution of Metabolic Pathways. This volume provides in-depth reviews of our current knowledge on the evolutionary origin of plant secondary metabolites and the enzymes involved in their biosynthesis. The chapters cover five major topics: 1. Role of secondary metabolites in evolution; 2. Evolutionary origins of polyketides and terpenes; 3. Roles of oxidative reactions in the evolution of secondary metabolism; 4. Evolutionary origin of substitution reactions: acylation, glycosylation and methylation; and 5. Biochemistry and molecular biology of brassinosteroids.

The papers assembled in this volume were originally presented at the joint meeting of the Phytochemical Society of North America and the Mid-Atlantic Plant Molecular Biology Society, in August 2000. The symposium from which these chapters were prepared was entitled "Regulation of Phytochemicals by Molecular Techniques" and was organised by James Saunders and Ben Matthews. This joint meeting was timely because of recent landmark advances in molecular biology and genomics as well as the renewed interest in phytochemistry as a rich source of nutraceuticals, drugs, and alternatives to synthetic agriculture pesticides. Progress in genome sequencing in plants such as Arabidopsis and rice has been remarkable, as have expressed sequence tag (EST) projects in other plants, including maize and soybean. Recently, private and public sector participants of the Human Genome Project announced that a rough draft of the human genome has been constructed. These advances directly influence phytochemical investigations by providing both insight and tools for exploring and manipulating genomes.The chapters cover a wide range of applications from molecular biology to phytochemistry, and from basic studies on promoters and gene expression to pathway regulation and engineering with transformed plants. A number of noteworthy aspects emerge from this volume: applications of molecular biology to phytochemical practical problems are succeeding; newly emerging molecular tools promise to open new doors to discovery; and remarkable progress has already occurred in phytochemical pathway engineering.

This monograph series is commissioned by the Phytochemical Society of North America (PSNA). The volumes in this series contain articles on developing topics of interest to scientists, students and individuals interested in recent developments in the biochemistry, chemistry and molecular biology of plants. Volume 36 centers on the role of phytochemistry in the rapid developments in biology brought about by the application of large-scale genomics approaches. Several functional genomic approaches discussed in this volume address plant gene function on a large scale. Plants are combinatorial chemists par excellence, and understanding the principles that relate enzyme structure to function will open up unlimited possibilities for the rational design of new enzymes to generate novel biologically active natural products. Knowledge of the molecular genetics of plant natural product pathways will also facilitate the engineering of these pathways for plant improvement and human benefit. Phytochemistry truly has a great future in the genomics and post-genomics eras.

The chapters presented in Secondary Metabolism in Model Systems are a microcosm of what the recent completion, or near completion, of various genome projects are enabling biochemists to understand not only about control and regulation of secondary metabolism, and how various pathways relate to each other, but also about its relation to primary metabolism. A major paradigm shift is occurring in the way researchers need to view "secondary" metabolism in the future.It is also clear that model systems, such as the ones discussed in the symposium, are providing new information and insight almost faster than researchers can process it!

The volumes in this series contain articles on developing topics of interest to scientists, students and individuals interested in recent developments in the biochemistry, chemistry and molecular biology of plants.

An excellent series volume covering the advances in understanding of gene functions, a high profile area of research due to recent genome projects This book provides essential information on new model systems available to biochemists The chapters in this volume are based on the papers presented in the symposium entitled "Secondary Metabolism in Model Systems"

The Phytochemical Society of North America held its forty-fourth annual meeting in Ottawa, Ontario, Canada from July 24-28, 2004. This year's meeting was hosted by the University of Ottawa and the Canadian Forest Service, Great Lakes Forestry Centre and was held jointly with the International Society of Chemical Ecology. All of the chapters in this volume are based on papers presented in the symposium entitled "Chemical Ecology and Phytochemistry of Forest Ecosystems". The Symposium Committee, Mamdouh Abou-Zaid, John T. Arnason, Vincenzo deLuca, Constance Nozzolillo, and Bernard Philogene, assembled an international group of phytochemists and chemical ecologists working primarily in northern forest ecosystems. It was a unique interdisciplinary forum of scientists working on the cutting edge in their respective fields. While most of these scientists defy the traditional labels we are accustomed to, they brought to the symposium expertise in phytochemistry, insect biochemistry, molecular biology, genomics and proteomics, botany, entomology, microbiology, mathematics, and ecological modeling. A collection of papers presented at the 44th Annual meeting of the Phytochemical Society of North America Representation from a unique interdisciplinary forum of scientists Includes discussions on new genomics research in forest health

Chemical warfare between plants and their herbivores and pathogens was first brought to our attention by the publication 25 years ago of the paper by Fraenkel in Science. There, he pointed out that most plants have similar nutritional characteristics so that the selection of plants by insect herbivores must depend on the relative toxicity of secondary compounds. This led, rather gradually, to a host of papers on plant-herbivore interactions. More or less at the same time, insect physiologists and ecologists were starting to realise the importance of chemical communi­ cation systems in determining sexual and other characteristics of insect behaviour. Nine years ago the Phytochemical Society of North America published their Symposium on 'Biochemical Interaction Between Plants and Insects' in which the plant apparency theory was expounded by both Paul Feeny and Rex Cates and David Rhoades. This stated that plants which are apparent usually contain secondary components which reduce digestibility (tannins and lignins) while ephemeral plants have more toxic, and perhaps less costly, compounds such as alkaloids. These papers stimulated much research on biochemical ecology. The recognition of the importance of the biochemical factors in such interactions is not just of scientific interest. It is vitally important in programs for the production of new varieties of cultivated plants, especially in tropical countries where about one-third or more of the crops are lost to predation or disease.

Throughout the tropics, vast areas of rainforest and other biologically diverse lands are being cleared for agricultural or related uses. Rainforests, the most dramatic example of tropical habitat destrucLion, are estimated to be disappearing at the rate of up to 20.4 million hectares per year world-wide (based on FAO estimates; see World Resources 1990-1991, Oxford University Press)­ more than 2% of the total area covered by tropical rainforests per year. Destruction of these complex habitats results in the irreversible loss of both plant and animal diversity, and dramatically illustraLes the need to investigate these threatened species for potentially useful constituents-especially the identification and characterization of novel biologically-active phytochemicals with pharmacologiical and/or pesticidal properties. This volume is based on papers presented by invited speakers at an international symposium entitled "Phytochemical POlential of Tropical Plants: held in conjunction with the second joint meeting of the Phytochemical nd Societies of Europe and North America, as well as the 32 annual meeting of the latter society. The meeting was held at the Deauville Hotel, Miami Beach, Florida, USA from August 8-12,1992. One hundred and twenty-five participants from more than 20 countries attended this meeting.

Phytochemicals from medicinal plants are receiving ever greater attention in the scientific literature, in medicine, and in the world economy in general. For example, the global value of plant-derived pharmaceuticals will reach $500 billion in the year 2000 in the OECD countries. In the developing countries, over-the-counter remedies and "ethical phytomedicines," which are standardized toxicologically and clinically defined crude drugs, are seen as a promising low­ cost alternatives in primary health care. The field also has benefited greatly in recent years from the interaction of the study of traditional ethnobotanical knowledge and the application of modem phytochemical analysis and biological activity studies to medicinal plants. The papers on this topic assembled in the present volume were presented at the annual meeting of the Phytochemical Society of North America, held in Mexico City, August 15-19, 1994. This meeting location was chosen at the time of entry of Mexico into the North American Free Trade Agreement as another way to celebrate the closer ties between Mexico, the United States, and Canada. The meeting site was the historic Calinda Geneve Hotel in Mexico City, a most appropriate site to host a group of phytochemists, since it was the address of Russel Marker. Marker lived at the hotel, and his famous papers on steroidal saponins from Dioscorea composita, which launched the birth control pill, bear the address of the hotel.

Diversity within and among living organisms is both a biological impera­ tive and a biological conundrum. Phenotypic and genotypic diversity is the critical currency ofecological interactions and the evolution of life. Thus, it is not unexpected to find vast phytochemical diversity among plants. However, among the most compelling questions which arise among those interested in ecological phytochemistry is the extent, nature, and reasons for the diversity of chemieals in plants. The idea that natural products (secondary metabolites) are accidents of metabolism and have no biological function is an old one which has resurfaced recently under a new term "redundancy. " Redundancy in the broader sense can be viewed as duplication of effort. The co-occurrence of several classes of phytochemieals in a given plant may be redundancy. Is there unnecessary duplication of chemical defense systems and ifso, why? What selective forces have produced this result? On the other hand, why does the same compound often have multiple functions? At a symposium of the Phytochemical Society of North America held in August 1995, in Sault Ste. Marie, Ontario, Canada, the topic "Phytochernical Redundancy in Ecological Interactions" was discussed. The chapters in this volume are based on that symposium. They both stimulate thought and provide some working hypotheses for future research. It is being increasingly recognized that functional diversity and multiplicity of function of natural products is the norm rather than the exception.

Since 1994, the Phytochemical Society of North America has devoted its annual symposia to topics with biological perspectives. Our last four volumes have dealt with medicinal plants (1994), plant/insect interactions (1995), food phytochemicals (1996), and plant/microbe interactions (1997), respectively. The Symposium held in Pullman, Washington, July 26-31, 1998 brought many aspects of these previous symposia once again to the forefront. This time, however, there was greater emphasis on the potential applications of phytochemistry to the diverse topics of human health and nutrition and plant defense. As we learned about innovative uses of molecular biology as it is being applied to these topics, we were reminded once again of the biochemical th foundation on which these advances rest. On the occasion of the 75 birthday of G.H. Neal Towers, which we were privileged to celebrate, a perspective of where we began and how far we have advanced was made patently real for those in attendance. The papers assembled in this volume were presented during the Sympo- sium. Roughly grouped under three broad topics, they include: I.Drug Discov- ery and Pathway Engineering toward New MedicinallNutriceutical Targets (papers by Cragg, Croteau, Thompson, Costa, McLaughlin, Dixon, and Matern), 2. Roles for Polyphenols-Biosynthesis and Applications (Gross, Hillis, Haslam, and Ferreira), 3. New Chemical Prospects and Plant Defense (Asakawa, Selmar, Houghton, and Mizutani).

This is the first volume to be published under a new series agreement for Recent Advances in Phytochemistry, co-published with the Phytochemical Society of North America.

This volume is based on papers presented by invited speakers at a symposium entitled "Plant Nitrogen Metabolism" held in conjunction with the 28th Annual Meeting of the Phytochemical Society of North America. The meeting took place on the campus of the University of Iowa at Iowa City during June 26-30, 1988, and attracted 110 participants from 11 countries. The goal of the symposium was to trace the pathway by which nitrogen passes from soil and atmosphere into both primary and secondary nitrogenous metabolites, focusing upon areas which were felt to be most rapidly expanding. From nodulines (nodule specific proteins) and GS/GOGAT mutants to sugar mimics (polyhydroxyalkaloids) and herbicide inhibitors of amino acid metabolism, research in nitrogen metabolism has expanded into areas barely envisioned only a few years ago. Both the nitrogen specialist and the general plant biochemist will be pleased by the range of topics covered here. Following an overview in Chapter 1 of plant nitrogen metabolism, the remaining chapters are loosely organized into three groups. Chapters 2-6 deal primarily with the biochemistry and molecular biology of nitrogen assimilation and transport, Chapters 7-9 with amino acid metabolism, and Chapters 10-12 with secondary metabolites.

The influence of compounds in the environment on the chemistry of plants is a topic which has economic and scientific implications of global importance. Selected presentations in this symposium covered several topics within this immense field, inclusive of air, soil, and aquatic sources of the compounds. As demonstrated in Chapter 4 by O'Keeffe et al. we have not restricted the discussion solely to negative aspects of anthropogenic compounds. Nor could we begin to cover comprehensively all major classes of environmental compounds in the air, soil or water that may have an effect on the phytochemistry of plants. Our intent was to focus on some of the timely and well publicized environmental constituents such as ozone, sulfur dioxide, acid rain, and others, to provide an authoritative publication specifically related to environ­ mental modifications of plant chemistry. The concept of this symposium originated with the Executive Committee of the Phytochemical Society of North America in 1983. It was brought to fruition during July 13-17, 1986 on the campus of the University of Maryland at the annual meeting of the PSNA through the efforts of the Symposium Committee composed of James A. Saunders and Lynn Kosak-Channing. Financial support for this meeting was provided by the Phytochemical Society of North America, as well as by generous contributions from E. I. du Pont de Nemours & Company and the U. S. Department of Agriculture. The Organizing Committee, consisting of J. A. Saunders (Chair), J. M. Gillespie, L. Kosak-Channing, E. H. Lee, J. P.

In this volume of Recent Advances in Phytochmistry you will find a record of the pioneering attempts of plant biochemists and molecular biologists to modify the patterns of secondary metabolism in plants, as presented at the 33rd annual meeting of the Phytochemical Society of North America, in Asilomar, California, on June 27 -July I, 1993. The studies described here represent a marriage of the newest of technologies with one of the oldest human activities, exploitation of plant chemistry. They also represent the beginning of a new era of phytochemical research, an era that will undoubtedly begin to provide answers to some of the long-standing questions that have absorbed plant biochemists for the past century. There is, for instance, a common deflating experience to which every worker in the area of plant secondary metabolism can probably relate. After hearing about the latest research findings regarding some aspect of remarkable compound "X", someone in the audience finally directs the inevitable question at the hapless speaker. "Tell me, is anything known as to the biological role of compound "X" in the plant?" The answer, in most cases, must be "essentially nothing"! This is a frustrating scenario for both the speaker and the audience, since the very fact that a complex biosynthetic pathway remains encoded in a plant genome points to an associated selective advantage. The problem is that establishing the nature and scale of that advantage is a very complex task.

This volume contains reviews presented at the 31 st annual meeting of the Phytochemical Society of North America, held at Colorado State University in Fort Collins, Colorado on June 22-26, 1991. This symposium, entitled Phenolic Metabolism in Plants, celebrated the origin of this society as the Plant Phenolics Group of North America; the first symposium, entitled Biochemistry of Plant Phenolic Substances, was also held at Fort Collins from August 31 to September 1, 1961. A brief history of the Society is presented in Chapter 12 by Stewart Brown, one of the original founders of the Society. We dedicate this volume to Hans Grisebach, 1926-1990, Professor of Biochemistry at the Biologisches Institut II, Freiburg, Germany, where he headed for many years a laboratory responsible for major advances in the area of phenolic metabolism; this will be self evident from the numerous bibliographical references cited in the literature for papers by his Freiburg group from about 1958 until now, and subsequently by former students and colla­ borators. His impact on the data reviewed in this volume will testify to this.

Since 1994, the Phytochemical Society of North America has devoted its annual symposia to topics with biological perspectives. Our last four volumes have dealt with medicinal plants (1994), plant/insect interactions (1995), food phytochemicals (1996), and plant/microbe interactions (1997), respectively. The Symposium held in Pullman, Washington, July 26-31, 1998 brought many aspects of these previous symposia once again to the forefront. This time, however, there was greater emphasis on the potential applications of phytochemistry to the diverse topics of human health and nutrition and plant defense. As we learned about innovative uses of molecular biology as it is being applied to these topics, we were reminded once again of the biochemical th foundation on which these advances rest. On the occasion of the 75 birthday of G.H. Neal Towers, which we were privileged to celebrate, a perspective of where we began and how far we have advanced was made patently real for those in attendance. The papers assembled in this volume were presented during the Sympo- sium. Roughly grouped under three broad topics, they include: I.Drug Discov- ery and Pathway Engineering toward New MedicinallNutriceutical Targets (papers by Cragg, Croteau, Thompson, Costa, McLaughlin, Dixon, and Matern), 2. Roles for Polyphenols-Biosynthesis and Applications (Gross, Hillis, Haslam, and Ferreira), 3. New Chemical Prospects and Plant Defense (Asakawa, Selmar, Houghton, and Mizutani).

The papers assembled in this volume were originally presented at the joint meeting of the Phytochemical Society of North America and Phytochemical Society of Europe held in Noordwijkerhout, The Netherlands, April 20-23, 1997. The meeting was organized by an international panel of scientists from both societies. The symposium from which the related contributions on phytochemi- cal signaling and plant-microbe interactions were taken was entitled "Commu- nication of Plants with the Environment." The chapters included in this volume cover traditional areas in plant chemical ecology, as well as address fundamental issues on the involvemerrt ofphytochemicals in intra- and interspecific signaling, applications of the knowledge gained from such studies, and evolutionary origins. T.he term microbes is used here in the broadest sense to encompass bacteria, fungi, and nematodes. An array of plant and fungal metabolites ranging from simple phenolics, salicylic acid, hydroxamic acids, flavonoids, polysaccharides, fatty acid derived octadecanoids, to trichothecenes and perylenequinones are discussed.A number of important themes emerge: i) the multifunctional roles of many phytochemi- cals, ii) the power of molecular techniques for studying biosynthetic pathways and gene function, iii) the central role of natural products in pathogenesis and disease resistance, and iv) the identification of promising areas for future research and development of applications. The opening chapter by Osbourn et al. discusses the emerging role and significance of saponins as antifungal agents, compounds already well-docu- mented as important mediators of plant-insect interactions. McCormick et al.

Phytochemists are aware that their focus of interest is receiving attention from a wider segment of society and from a greater diversity of disciplines within the scientific community than ever before. Nonetheless, they were bemused to learn three years ago that "until recently scientists didn't even know phytochemi­ cals existed" (Newsweek, April 24, 1994). Changing public perception of the positive contributions of phytochemicals to human well-being has foundations in scientific advances. With popular reports emphasizing the important implica­ tions of phytochemicals in the daily lives of people, there is a pressing need for those working in this area to explain their diverse scientific activities to the public. Chemicals from plant foods are linked through epidemiological and ex­ perimental studies with reduced incidence of chronic degenerative diseases. Phytomedicines, standardized according to particular constituents, are making increasing contributions to health care. Naturally occurring constituents of plants are recognized as fundamental to the appeal, quality, and marketability of food products. In light of such developments, perceptions by phytochemists of their own discipline and its applications are expanding. Until recently, food phyto­ chemistry largely implied food toxicants. Food plants were familiar, but seldom the source of novel economically important compounds. Increasingly sophisti­ cated methods of analysis, however, have opened new opportunities for under­ standing the nature and functions offood constituents, and for manipulating them to improve the quality, acceptability, and value of food products.

This is the first volume to be published under a new series agreement for Recent Advances in Phytochemistry, co-published with the Phytochemical Society of North America.

This is the second volume since the reintroduction of the Recent Advances in Phytochemistry (RAP) series, an annual journal supported by the Phytochemical Society of North America. Topics appropriate for RAP include the biosynthesis of natural products and regulation of metabolism, the ecology of specialized metabolites and the evolution of their pathways, and the effects of natural products or plants on human health. Research appropriate for RAP involves genomics, proteomics, metabolomics, natural product structural determination and new technology development, medicinal chemistry and metabolic engineering, or any of the myriad of fields that are now closely associated with what may be called “traditional phytochemistry” and plant biochemistry. The advent of post-genomics-based ways of thinking, of systems biology, of synthetic biology, of comparative genomics/ proteomics/ transcriptomics/ metabolomics and especially of the introduction and establishment of a mentality that leads to support of large collaborative projects, has opened up many new doors to scientists interested and versed in the (bio)chemistry of plants. The goal of RAP is to highlight these developments. Two main types of articles are printed in RAP: Perspectives and Communications. Perspectives in RAP are expected to synthesize results from the primary literature and perhaps from new/novel results and place these in perspective relative to the broader field. These articles may be similar to review articles, but also are intended to present important ideas and hypotheses, and may present proposals for interesting directions in the field. It is the hope of the Editorial Board that these articles will be of great value to a large audience. Communications are intended to represent new advances in the field that will be of interest to a large audience. Articles of both types are typically solicited from the Society membership based on the content of the annual meeting talks, but in keepingwith the title “Recent Advances in Phytochemistry” the editorial board reserves the right to solicit additional Perspectives and/or Communications from non-attendees as well (e.g., where an editorial board member has knowledge of an interesting recent advancement that would be of general interest to the society membership). All submissions to RAP go through a rigorous peer review process, overseen by the Editorial Board, which includes external review. RAP is indexed with Springer published journals. All RAP papers are available not only in the published volume form, but also electronically through Springer’s online literature services. This marks a significant change from past volumes of RAP and it is the hope of the Editorial Board that this will lead to broader dissemination of the contents of and greater interest in RAP. This 42nd volume of RAP includes a total of seven articles, many, but not all, based on talks presented at the 50th annual meeting of the PSNA. As was seen in RAP volume 41, These seven Perspectives give a very good picture of the breadth of plant (bio)chemistry research in North America, which is also indicative of the state of the field worldwide. Each of these articles describes the integration of several different approaches to ask and then answer interesting questions regarding the function of interesting plant metabolites, either in the plant itself or in interactions with the environment (natural setting or human health application). Many of these Perspectives have a strong ecological focus. McCormick et al. review the discovery of the biosynthetic pathway leading to production of trichothecene mycotoxins such as the T-2 toxin in plant pathogenic and other fungi. These compounds play very important roles in plant-pathogen interaction, and are very significant from a human health perspective. In a complementary paper, Duringer et al. describe recent technological advances in monitoring mycotoxins such as ergovaline and lysergic acidin forage crops, using state of the art and highly sensitive mass spectrometric means. Gross reviews the current understanding of how infochemicals mediate interactions between plants and insects, and highlights how such knowledge can be used to mitigate crop losses by pests. Two Perspectives discuss how recent technological advances are making an impact on our understanding of the role of plant hormones in plant growth and development. Gouthu et al. outline highly sensitive methods for measurement of plant hormones in tissues such as developing grape berry. In contrast, McDowell and Gang outline how new transcriptional profiling techniques are shedding light on old questions, such as how rhizome development is regulated by different plant growth regulators. The last two Perspectives outline the role of biotechnology in modern plant biochemistry research. Makhzoum et al. review the long history of use of hairy roots and provide perspective on future utility of this tissue type in continuing to uncover mechanisms of plant natural product biosynthesis, among other apolications. Dalton et al. outline, on the other hand, recent efforts to produce non-native polymers of human interest in plants and outline many of the challenges associated with such investigations. We hope that you will find these Perspectives to be interesting, informative, and timely. It is our goal that RAP will act not only as the voice of the PSNA, but that it will serve as an authoritative, up-to-date resource that helps to set the gold standard for thought and research in fields related to plant biochemistry.

Forest trees constitute one of the major resources of the world and their utilization, either for structural purposes or for the materials which they yield, dates back to antiquity. Over the centuries, the exploitation of this resource has become progressively more sophisticated, and, in many parts of the world has led to the development of highly complex forest-based industries. The research and development work which led to these industrial uses fostered the formation of numerous technical societies and associations, which, through their meetings and publi­ cations, have facilitated communication and the exchange of ideas. Over the years, there have been numerous symposia devoted to wood and the many facets of its properties and utilization. However, rarely has the emphasis in such symposia been placed upon the living tree and the changes which it undergoes in relation to its ultimate utilization. Hence the Phytochemical Society of North America arranged the symposium, "The Structure, Biosynthesis, and Degradation of Wood", held at the University of British Columbia in August, 1976. the contributions to which form the basis of the present volume.

For centuries it has been recognized that plants relate to human health and well-being in many ways beyond their fundamental role as primary sources of food and energy. Many of the unique plant constituents have pronounced effects on animal systems or in the human body; some of them are potentially harmful and represent a risk in the use of a parttcular plant or in the exposure to it, others are useful as medicinal agents in the treatment of diseases. Many of the latter are extracted from plant materials on a large scale for marketing as drugs and even more of them have served as structural prototypes which inspired chemists to synthesize analog drugs with even more desirable properties. Clearly, today's drug therapy had its origins in the explora­ tion and exploitation of pharmacologically active plant con­ stituents. It is therefore appropriate that a symposium of the Phytochemical Society of tlorth America \'1as devoted to this subject. The present volume consists of eleven rapers dealing with various aspects of the topic "Phytochemistry as Related to Disease and Medicine", which were presented at the Four­ teenth Annual Meeting of the Phytochemical Society of tlorth America held tn August 1974 at Hestern Carol ina University in Cullowhee, N.C. Plant hallucinogens are the subject of the first three chapters. The first, by Schultes, reviews the occurrence of hallucinogenic agents in plants, in tabular form. Emphasis is on plants from Central and South America.

Although many reviews and articles about germination have been published, our understanding of the process is far from complete. Some of the reactions involved in the transforma­ tions and translocation of reserve compounds and their final fate in the growing tissues was the subject of the annual symposium of the Phytochemical Society of North America which was held in August, 1982, on the campus of the University of Ottawa, Canada. A major emphasis was on low molecular weight compounds, amino acids and sugars, and the checks and balances operating as they are produced by hydrolysis in reserve tissues and transformed in the growing tissues. The critical role of membranes was given especial emphasis. The closing presentation was an anthropocentric review of the nutritional benefits accrued during germination, and provided a scientific basis for the inclusion of sprouted seedlings in the human diet. Dr. R. G. Fulcher introduced the symposium topic with an elegant histochemical study in which the site and nature of seed reserves were defined by means of the glowing colors of fluorescence microscopy. The symposium was organized by C. Nozzolillo with advice and assistance from fellow PSNA members S. A. Brown, J. T. Arnason, and A. Picman and a visiting scientist from Sweden, C. Liljenberg.

This volume is based on the proceedings of the Phytochemical Society of North America's 23rd Annual Meet­ ing on "Phytochemical Adaptations to Stress" which was held at the University of Arizona, Tucson, July 5-8, 1983. It contains a series of articles which focus on our current knowledge on the production of secondary (natural) metabolites by higher plants in response to biological and physiological stresses. The editors of this volume are deeply indebted to a number of people and organizations for their support and contributions which were critical to the success of this scientific meeting. Generous grant support was provided by the Agricultural Research Service of the United States Department of Agricul­ ture. Additional financial support came from the Phytochemical Society of North America. Indispensable services and personnel were donated by the Departments of Chemistry and Pharmaceutical Sciences, the College of Agriculture and the Office of Arid Lands Studies of the University of Arizona. Special recognition is due to Paul Mirocha of the Office of Arid Lands Studies for his drawing of the frontispiece and the superb photograph on the jacket. The Division of Conferences and Short Courses of the University of Arizona deserves credit for its pivotal role in maintaining a well-run and pleasant conference. Many other volunteers gave their time and energy to make the Symposium a success; we wish to mention two from the Department of Pharmaceutical Sciences, Brian Week and Catherine L. Buckner.

Phenolic compounds have attracted the attention of those interested in plant constituents for over 200 years. First as dyestuffs, meaicinals and tannins and, much later, because of their potential use in examining the systematic and evolutionary relationships of plants, and their impli- cation in defence against both herbivores and phytopatho- gens. It is not surprising, therefore, that the first formally organised Society of Phytochemists, the Plant Phenolics group which was established in England in 1958, should have devoted themselves to an intensive study of these compounds. They were quickly followed by a like group in North America. But, by the mid-1960's, it was obvious to the members of both societies that their net was spread wider than just phenolic compounds and in 1965 both adopted a more appropriate name, The Phytochemical Society (now Phytochemical Society of Europe (PSE), and The Phytochemical Society of North America (PSNA) respec- tively).In spite of this broadening of interest, both socie- ties have continued to devote a major portion of their deliberations to phenolic compounds and it is entirely appropriate, therefore, that their first joint Symposium, held in the late summer of 1977 at the Rijksuniversiteit te Gent, Belgium, should be concerned with "The Biochem- istry of Plant Phenolics. " First occasions are often difficult, but the chief organiser of this Symposium, Professsor Ch~is van Sumere, Head of the Laboratorium voor Plantenbiochemie of the Rijksuniversiteit te Gent with his charming wife and enthu- siastic staff overcame all obstacles.