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

New sesquiterpene lactones from Inula species

Chromenes and benzofurans of the asteraceae, their chemistry and biological significance

Sesamin, sesamolin and the origin of sesame☆

Fragrant sesquiterpenes from agarwood

Die Untersuchung von sechs mexikanischen Arten der alten Gattung Eupatorium, die jetzt in die Gattungen Ageratina, Critonia und Fleischmannia eingeordnet werden, ergibt zwei neue Sesquiterpensauren (12 und 16), ein Cadinan-Derivat (40) und drei Sesquiterpenlactone (41, 57 und 58). Auserdem werden neben bereits bekannten Verbindungen elf neue Thymolderivate (3–10 und 46–48), vier p-Hydroxyacetophenon-Derivate (21, 26, 30 und 45), drei Benzoesaurebenzylester (35–37), ein Flavanon (54) und ein Lignan (60) isoliert. Die Konstitutionen werden durch spektroskopische Daten sowie durch einige chemische Reaktionen geklart. Die chemotaxonomischen Aspekte werden diskutiert.



Naturally Occurring Terpene Derivatives, 76. On Constituents of the Eupatorium Group



The investigation of six Mexican species of the old genus Eupatorium which are now placed in the genera Ageratina, Critonia and Fleischmannia, yields two new sesquiterpenic acids (12 and 16), a cadinane derivative (40) and three sesquiterpene lactones (41, 57 and 58). In addition besides already known compounds eleven new thymol derivatives (3–10 and 46–48), four p-hydroxy-acetophenone derivatives (21, 26, 30 and 45), three benzyl benzoates (35–37), a flavanone (54) and a lignan (60) are isolated. The structures are established by spectroscopic data as well as by some chemical reactions. The chemotaxonomical aspects are discussed.

Natürlich vorkommende Terpen‐Derivate, 76. Über Inhaltsstoffe der Eupatorium‐Gruppe

Aus zwei Zexmenia-Arten werden zwei neue Sesquiterpene (10 und 12), mehrere neue Sandaracopimar-8(14),15-dien-Derivate (15, 17–24, 26 und 27) und drei neue Sesquiterpenlactone (28–30) isoliert. Die Konstitutionen werden durch spektroskopische Methoden und einige chemische Reaktionen geklart. Die chemotaxonomische Situation der dritten Gruppe der Subtribus Verbesininae wird diskutiert.



Naturally Occurring Terpene Derivatives, 117 New Sandaracopimardiene Derivatives, Sesquiterpenes, and Sesquiterpene Lactones from Zexmenia Species



From two Zexmenia species two new sesquiterpenes (10 and 12), several new sandaracopimar-8(14),15-diene derivatives (15, 17–24, 26, and 27) and new sesquiterpene lactones (28–30) were isolated. The structures of these compounds have been elucidated by spectroscopic methods and some chemical reactions. The chemotaxonomical situation of the third group of the subtribe Verbesininae is discussed.

Natürlich vorkommende Terpen-Derivate, 117: Neue Sandaracopimardien-Derivate, Sesquiterpene und Sesquiterpenlactone aus Zexmenia-Arten

Neue guajen-derivate aus Parthenium hysterophorus und ein weiteres pseudoguajanolid aus Ambrosia cumanensis☆

Die Untersuchung einiger sudamerikanischer Verbesina-Arten ergibt neben bereits bekannten mehrere neue Sesquiterpene, deren Konstitutionen durch spektroskopische Methoden und durch einige chemische Reaktionen geklart werden (5, 13–15, 18, 20, 22, 23, 25, 27, 29, 32, 33 und 35).



Naturally Occurring Terpene Derivatives, 109: New Eudesmane Derivatives and other Sesquiterpenes from Verbesina Species



The investigation of some South American Verbesina species affords besides already known ones several new sesquiterpenes, their structures being elucidated by spectroscopic methods and some chemical reactions (5, 13–15, 18, 20, 22, 23, 25, 27, 29, 32, 33, and 35).

Michael Lonitz

Papers

Natürlich vorkommende Terpen‐Derivate, 76. Über Inhaltsstoffe der Eupatorium‐Gruppe

Natürlich vorkommende Terpen-Derivate, 117: Neue Sandaracopimardien-Derivate, Sesquiterpene und Sesquiterpenlactone aus Zexmenia-Arten

Neue guajen-derivate aus Parthenium hysterophorus und ein weiteres pseudoguajanolid aus Ambrosia cumanensis☆

Natürlich vorkommende Terpen-Derivate, 109: Neue Eudesman-Derivate und andere Sesquiterpene aus Verbesina-Arten

Neue sesquiterpene aus Verbesina occidentalis