Biological activities of sesquiterpene lactones

On the origins of triterpenoid skeletal diversity.

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 simple β-carboline alkaloids

Anti-bacterial activity of some Brazilian medicinal plants

http://repositorio.ufba.br/ri/bitstream/ri/8757/1/5555f.pdf

Diterpenoid furans from Pterodon species

Mass Spectrometry in Structural and Stereochemical Problems. XX.1 Carapanaubine, a New Alkaloid from Aspidosperma carapanauba and Some Observations on Mass Spectra of Oxindole Alkaloids2

Skin penetration by Schistosoma mansoni cercariae may be blocked by 1,4-and 1,2-naphthoquinones applied topically. Of 23 naphthoquinone derivatives synthesized, 15 afforded almost complete protection when applied in solution to the tails of mice 24 hours before exposure to cercariae. On the basis of present evidence the 5-carbon atom side chain present in naturally occurring lapachol seems to be important for activity, and this is in accord with the previous observation that effective protective agents are liposoluble. Topically applied cercarial penetration inhibitors are presently the only prophylactic agents available for use in the field.

B. Gilbert

Papers

Diterpenoid furans from Pterodon species

Mass Spectrometry in Structural and Stereochemical Problems. XX.1 Carapanaubine, a New Alkaloid from Aspidosperma carapanauba and Some Observations on Mass Spectra of Oxindole Alkaloids2

Schistosomiasis mansoni: blockage of cercarial skin penetration by chemical agents: I. naphthoquinones and derivatives

Schistosomicidal sesquiterpene lactone from Eremanthus elaeagnus

Terpenoids. LIII.1a Demonstration of Ring Conformational Changes in Triterpenes of the β-Amyrin Class Isolated from Stryphnodendron coriaceum