Biological activities of sesquiterpene lactones

Thome, Robert F. (Rancho Santa Ana Botanic Garden, Claremont, CA 91711). Classification and geography of the flowering plants. Bot. Rev.58(3): 225–348. 1992.—This treatment of the flowering plants is the latest revision of my classification of the Class Angiospermae and replaces my 1983 and more recent 1992 synopses. An update is necessary because so much new information has been published in the last decade pertinent to the classification of the flowering plants. About 870 such recent books, monographs, and other botanical papers are cited in the Introduction, listed primarily by the botanical discipline that they represent. Also considerable changes in my classification have been necessitated by my narrowed family- and ordinal-gap concepts, acceptance of the ending “-anae” for superorders in place of the traditional but inappropriate “-iflorae,” and acceptance of more prior or more widely used names for the categories above the family. A new phyletic “shrub” replaces earlier versions, and attempts to indicate visually relative sizes and relationships among the superorders, orders, and suborders. One table includes a statistical summary of floweringplant taxa: ca. 233,900 species of 12,650 genera, 437 families, and 708 subfamilies and undivided families in 28 superorders, 71 orders, and 71 suborders of Angiospermae. Three other tables summarize the known indigenous distribution of the families and subfamilies of angiosperms about the world. The synopsis lists the flowering plant taxa from the class down to the subfamily (and in Asteraceae down to the tribe) with indication of the degree of confidence I place in the circumscription and placement of each category above the subfamily, the best available estimates of the number of genera and species for each category, and the known indigenous distribution of each subfamily and family. Table V lists alphabetically the geographical abbreviations used in the synopsis. The extensive bibliography of recent literature should be helpful to those persons interested in the classification of the flowering plants.

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Classification and geography of the flowering plants

The Asteraceae is characterized by structurally diverse sesquiterpene lactones and furanosesquiterpenes. In this review the tribal, subtribal and generic distribution of sesquiterpene lactones is examined and the compounds’ utility as taxonomic characters discussed. Sesquiterpene lactones fulfill the major requirements for good analytic and synthetic characters. Studies of infraspecific sesquiterpene lactone variation indicate that different elements within complex taxa are often defined by distinct chemistries, termed chemotypes. Chemotypes have been identified within many of the thoroughly investigated taxa:Ambrosia camphorata, A. chamissonis, A. confertiflora, theA. cumanensis-A. psilostachya-A. artemisiifolia complex,A. dumosa, Artemisia tridentata, Gaillardia pulchella andMelampodium leucanthum. Such an analytic usage is mostly restricted to the infraspecific level. Synthetic usage at the interspecific level and above profits from the application of a biogenetically based methodology for sorting out the complex molecules’ carbon-skeletal and substitutional features into unit characters. Cladistics or Hennigian phylogenetic systematics provides a useful framework for such an analysis. Preliminary surveys indicate that sesquiterpene lactones are especially good characters for differentiating subtribes within several major tribes: the Vernonieae, Heliantheae and Mutisieae. As yet, too few data are available for other tribes to discern such patterns. Species surveys inVernonia, Ambrosia, Iva, Parthenium,Tetragonotheca andArtemisia demonstrate that sesquiterpene lactones are useful in discerning infrageneric groups. The biogenetic cladistic analysis of the interspecific sesquiterpene lactone variation inIva shows the efficacy of this analytical methodology. At present, such biogenetically based approaches are impeded by limited biosynthetic evidence and the erratic distribution of sesquiterpene lactones within the family. Instances of apparent displacement of sesquiterpene lactones by other terpenoids (i.e. sesquiterpene furans, alcohols and acids, diterpenes, diterpene acids, etc.) at various taxonomic levels suggest that ultimately sesquiterpene lactones must be interpreted as taxonomic characters in the context of the family’s total terpene chemistry. All taxa from which sesquiterpene lactones have been reported are listed together with the compound names, major structural features and the literature cited. A less-complete listing is provided for taxa producing furanosesquiterpenes. Structures for all reported compounds are included. Two appendices listing alphabetically taxa and compounds and relevant text page numbers permit cross-indexing of plants and compounds.

Sesquiterpene lactones as taxonomic characters in the asteraceae

In the twelve years since the first review article dealing with chemical constituents of the Hepaticae appeared in this series as Volume 42 (19), several short reviews concerned with chemical constituents of bryophytes have been published (22, 96, 144, 265, 271, 647, 649, 650) In 1988, a Symposium on Chemistry and Chemical Taxonomy of Bryophytes was organised on the behalf of the Phytochemical Society of Europe; the proceedings of this meeting appeared as a book entitled Bryophytes: Their Chemistry and Chemical Taxonomy (651) The symposium concerned itself with phytochemical, biochemical, botanical, chemotaxonomical, pharmaceutical, biotechnological and environmental aspects of bryophytes as well as with the synthesis of the terpenoids and aromatic compounds bryophytes elaborate The physiological and biochemical aspects of bryophytes have also been described in a recent book Bryophytes Development: Physiology and Biochemistry (139)

Chemical Constituents of the Bryophytes

Publisher Summary The chapter focuses on the developmental aspects of immunity. The ontogenetic development of immune responses in the immature animal and the developmental cellular stages of the immune response in the adult animal are discussed in this chapter. The cellular mechanisms underlying the several immune responses have not received the full attention either to the evolutionary principles underlying the development of all biological systems or to the broad biological rules that govern the proliferative and differentiate activities of cells in any biologically functioning system. The chapter reviews the immunological status of fetal and neonatal mammals as well as several aspects of the ontogeny of the immune response when examined by the most sensitive technique presently available. Developmental stages of immune reactions and their mutual relationships such as relationship of phagocytosis to specific cellular reactions, relationship of delayed hypersensitivity to antibody formation, and dynamics of antibody formation are also presented in this chapter. The increase of immunological capacity with age and the appearance of natural antibodies result solely from specific antigenic stimulation; the chapter discusses the Unitarian concept of cell differentiation and proliferation underlying any form of immunological response. Several methods for studying developmental aspects of immunity and immunological development are also discussed in this chapter.

Developmental aspects of immunity.

Sesquiterpene lactones of the umbelliferae

Sesquiterpene lactones and lactone glycosides from Hymenoxys species

The small lymphocyte as a cell type is one of the lasting problems of pathology, hematology, and the morphological interpretation of antibody formation and transplantation immunity. The defense against foreign tissues appears to be one of the basic functions of the small lymphocyte (Snell et al., 1961). An increasing number of papers deals with the role and significance of individual lymphocytic types in homograf t response, in Simonsen’s phenomenon, and in the induction of runt disease (Medawar, 1958; Anderson et al., 1960; Cole and Garver, 1961; Szenberg and Warner, 1961). Even small lymphocytes seem to be involved; for example, in graft-versus-host reaction in the chicken (Terasaki, 1959). The method of diffusion chamber cultivation was found appropriate for observing the potentialities of lymphocytes (Shelton and Rice, 1959; Schooley and Berman, 1960; Holub, 1958, 1960). T h e possibility of separating practically pure suspensions of small thoracic duct lymphocytes enabled us to obtain direct evidence about the nature of these cells. The comparison of cultivations of small lymphocytes in autotransplantation and homotransplant at ion experiments in diffusion chambers provides the possibility of estimating the cellular changes caused also by tissue antigens.

Miroslav Holub

Papers

Sesquiterpene lactones of the umbelliferae

Sesquiterpene lactones and lactone glycosides from Hymenoxys species

Potentialities of the small lymphocyte as revealed by homotransplantation and autotransplantation experiments in diffusion chambers

On terpenes. CXCII. The constitution and absolute configuration of onopordopicrine - A sesquiterpenic lactone from Onopordon acanthium L.

On terpenes. CCXVI. Sesquiterpenic lactones from Eupatorium cannabinum L. Revision of the structure of eupatoriopicrin