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

Peroxy natural products

Advances in triterpenoid research, 1990–1994

Structural and Histochemical Investigation of the Glandular Trichomes of Salvia aurea L. Leaves, and Chemical Analysis of the Essential Oil

Chemical composition of the essential oils and extracts of Achillea species and their biological activities: A review.

Seven xanthanolides were identified in the extract of X. italicum leaves. Antibacterial and cytotoxic activities were found for the total extract and its major constituents xanthinin and xanthatin.

Xanthanolides of Xanthium italicum Moretti and their biological activity.

The essential oils obtained from wild growing Hyssopus officinalis L. ssp. aristatus (Godr.) Briq. at two stages of development are found to be very similar in composition with 1,8-cineole (48.2% and 39.6%), isopinocamphone (16.3% and 29.2%) and β-pinene (11.4% and 39.6%) as major constituents. However, the essential oil obtained commercially from cultivated H. officinalis contains larger amounts of isopinocamphone (40.2%), pinocamphone (10.3%), and β-pinene (14.2%), but no traces of 1,8-cineole.

Chemical Composition of the Essential Oils of Two Hyssopus officinalis Taxa

The composition of the essential oil of Cotinus coggygria Scop (Anacardiaceae) was analyzed by GC and GC/MS, and 19 components were identified, 14 of them found for the first time in this plant The main constituents were identified as α-pinene (44%), limonene (20%) and β-pinene (114%)

Chemical Composition of the Bulgarian Sumac Oil

New sesquiterpenoids from Achillea clypeolata

The essential oils of wild growing Salvia tomentosa Mill, and S. scabiosifolia (Lam.), and cultivated S. officinalis L. (sect. Salvia, Lamiacea) were studied by GC and GC/MS. The number of compounds identified in the Salvia oils were 30, 31 and 22 respectively, the major ones being β-pinene (29.1% in S. tomentosa), camphor (48.7% in S. scabiosifolia) and α- and β-thujone (29.4% and 17.4% in S. officinalis).

Elena T. Tsankova

Papers

Xanthanolides of Xanthium italicum Moretti and their biological activity.

Chemical Composition of the Essential Oils of Two Hyssopus officinalis Taxa

Chemical Composition of the Bulgarian Sumac Oil

New sesquiterpenoids from Achillea clypeolata

Constituents of Essential Oils from Three Salvia Species