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

The present paper reviews the occurrence of glycosidically bound aroma compounds in the plant kingdom and discusses different hypotheses concerning their role in plants. Emphasis is on biotechnological methods for flavor release and flavor enhancement through enzymatic hydrolysis of glycoconjugated aroma substances.

Glycoconjugated aroma compounds: occurrence, role and biotechnological transformation.

The in vitro activity of parthenolide against Leishmania amazonensis was investigated. Parthenolide is a sesquiterpene lactone purified from the hydroalcoholic extract of aerial parts of Tanacetum parthenium. This isolated compound was identified through spectral analyses by UV, infrared, (1)H and (13)C nuclear magnetic resonance imaging, DEPT (distortionless enhancement by polarization transfer), COSY (correlated spectroscopy), HMQC (heteronuclear multiple-quantum coherence), and electron spray ionization-mass spectrometry. Parthenolide showed significant activity against the promastigote form of L. amazonensis, with 50% inhibition of cell growth at a concentration of 0.37 microg/ml. For the intracellular amastigote form, parthenolide reduced by 50% the survival index of parasites in macrophages when it was used at 0.81 microg/ml. The purified compound showed no cytotoxic effects against J774G8 macrophages in culture and did not cause lysis in sheep blood when it was used at higher concentrations that inhibited promastigote forms. Sodium dodecyl sulfate-polyacrylamide gel electrophoresis with gelatin as the substrate showed that the enzymatic activity of the enzyme cysteine protease increased following treatment of the promastigotes with the isolated compound. This finding was correlated with marked morphological changes induced by parthenolide, such as the appearance of structures similar to large lysosomes and intense exocytic activity in the region of the flagellar pocket, as seen by electron microscopy. These results provide new perspectives on the development of novel drugs with leishmanicidal activities obtained from natural products.

Antileishmanial Activity of Parthenolide, a Sesquiterpene Lactone Isolated from Tanacetum parthenium

New sesquiterpene lactones from Inula species

It is the major object of this review to present the presently known naturally occurring terpenoids and aromatic compounds of the Hepaticae. Furthermore, the biological activity of the isolated compounds and chemosystematics of the Hepaticae are summarized.

Chemical Constituents of Hepaticae

Sesquiterpene lactones from Ambrosia confertiflora (Compositae)

The sesquiterpene lactone chemistry of the genus Parthenium (compositae)

Glaucolide-A and -B, new germacranolide-type sesquiterpene lactones from Vernonia (compositae)

The geminal coupling and paramagnetic shift of exomethylene protons in the α,β′-unsaturated γ-lactone group of sesquiterpene lactones containing C8-α-hydroxyl groups

H. Yoshioka

Papers

Sesquiterpene lactones from Ambrosia confertiflora (Compositae)

The sesquiterpene lactone chemistry of the genus Parthenium (compositae)

Glaucolide-A and -B, new germacranolide-type sesquiterpene lactones from Vernonia (compositae)

The geminal coupling and paramagnetic shift of exomethylene protons in the α,β′-unsaturated γ-lactone group of sesquiterpene lactones containing C8-α-hydroxyl groups

The isolation and structure determination of artemisiifolin, a new germacranolide from ambrosia artemisiifolia L. (compositae)