Sesquiterpene lactones in various populations of Parthenium hysterophorus

Samples of 31 populations of Parthenium hyserophorus from varius areas of its world distribution were examined for their sesquiterpene lactone composition. On the basis of the occurrence of sesquiterpene lactones the samples were divided into seven chemical types. The most common is a type represented by plants containing parthenin as a major sesquiterpene lactone, and coronopilin and tetraneurin-A. All samples from North and Central America, Venezuela, South Africa, India, Australia, and one sample from Jamaica belong to this type. This suggests that P. hysterophorus recently introduced to South Africa, India and Australia originates in North and (or) Central America. On the other hand, there is a great diversity among examined South American populations. Plants from these populations usually contain hymenin which is their major sesquiterpene lactone. Some populations may also contain coronopilin, hysterin, and dihydroisoparthenin. A high diversity in the sesquiterpene lactone chemistry and the morphological differences between individual South American populations of this species indicate the possible existence of several taxa.     

Sesquiterpene lactones from Centaurea species

The investigation of further Centaurea species gave, in addition to known compounds, one new sesquiterpene lactone, 11β, 15-dihydroxysaussurea lactone, of the elemanolide type.     

Terpenoids and bibenzyls of 25 liverwort Frullania species

Twenty-five Frullania species (liverworts) were chemically investigated. Fourteen species produce allergy-inducing sesquiterpene lactones. Eighteen species contain bibenzyls. The sesquiterpene lactones and bibenzyls are obtained as the major components and they are valuable chemosystematic markers of Frullania species. On the basis of their chemical constituents, Frullania species can be divided into five chemotypes: sesquiterpene lactone-bibenzyl type; sesquiterpene lactone type; bibenzyl type; monoterpene type and cyclocolorenone type.     

Comparison of the feeding deterrent activity of some sesquiterpene lactones and a lignan lactone towards selected insect storage pests

Four sesquiterpene lactones isolated from Eurpatorium cannabinum, Homogyne alpina and Petasites albus (all Compositae), together with two of their adducts, as well as one lignan lactone of dibenzylbutanolide type from Libocedrus yateensis (Cupressaceae), were tested for their feeding deterrent activity against the adults of Sitophilus granarius and Tribolium confusum, as well as against the larvae of Tribolium confusum and Trogoderma granarium. The strongest deterrent activity against all species was exhibited by the lignan lactone yatein and the sesquiterpene spirolactone bakkenolide A. Both may be included to the class of very good insect feeding deterrents. The comparison presented here showed that the conjugated α-exomethylene moiety of the lactone ring was not the decisive factor for the deterrent activity in the investigated test model.     

Sesquiterpene lactones from Chrysanthemum coronarium

The flower heads of Chrysanthemum coronarium afforded a new sesquiterpene lactone, dihydrocumambrin A, in addition to the known cumambrin A.     

Ambrosanolides and secoambrosanolides from Ambrosia tenuifolia

Populations of Ambrosia tenuifolia from four regions of North Central Argentina differed substantially in sesquiterpene lactone content. Lactones and lactone derivatives isolated were peruvin, ambrosic acid, cumanin, psilostachyin, psilostachyins B and C, dihydropsilostachyin C, altamisin and altamisic acid.     

Diterpenoids and a sesquiterpene lactone from viguiera ladibractate

Eight known diterpene acids, ent-12-oxokaur-9(11),16-dien-19-oic acid, ent-12β-hydroxykaur-9(11),16-dien-19-oic acid, ent-isokaur-15(16)-en-17,19-dioic acid, ent-15α,16-epoxy-17-hydroxykaura-19-oic acid, ent-kaura-17,19-dioic acid, ent-kaur-16-en-19-oic acid, grandifloric acid, angeloyloxygrandifloric acid, as well as a new sesquiterpene lactone, ladibranolide, were isolated from Viguiera ladibractate. The stereochemistry of the sesquiterpene lactone was established by NOE experiments.     

A further sesquiterpene lactone esterified with a sesquiterpenic acid

The roots of Hypochoeris oligocephala afforded in addition to known compounds a further sesquiterpene lactone esterified with a sesquiterpenic acid as well as the corresponding free acid.     

Montafrusin,a new germacrolide from Montanoa frutescens

The investigation of Montanoa frutescens afforded a new sesquiterpene lactone of the germacrolide type, montafrusin, besides the known diterpenes kaurenic acid and its 15α-isovalerate.     

Pseudoguianolides in Helenium autumnale from pennsylvania

The main sesquiterpene lactone found in collections of Helenium autumnale L. from Pennsylvania was not helenalin, but tenulin. Minor constituents of the flowers were mexicanin I, flexuosin A, a new lactone C₁₅H₂₀O₄ and the flavone hispidulin.     

Two sesquiterpene lactones of Calea ternifolia var. Calyculata

Chemical analysis of Calea ternifolia var. calyculata yielded the known sesquiterpene lactone calein A, as well as two new modified heliangolid     

Sesquiterpene lactones from Centaurea glomerata

The investigation of the aerial parts of Centaurea glomerata afforded four new sesquiterpene lactones of the germacradienolide type and the lignan lactone arctigenin. Their structures were elucidated by spectroscopic methods.     

Sesquiterpene lactone stereochemistry influences herbivore resistance and plant fitness in the field

Background and Aims

Stereochemical variation is widely known to influence the bioactivity of compounds in the context of pharmacology and pesticide science, but our understanding of its importance in mediating plant–herbivore interactions is limited, particularly in field settings. Similarly, sesquiterpene lactones are a broadly distributed class of putative defensive compounds, but little is known about their activities in the field.

Methods

Natural variation in sesquiterpene lactones of the common cocklebur, Xanthium strumarium (Asteraceae), was used in conjunction with a series of common garden experiments to examine relationships between stereochemical variation, herbivore damage and plant fitness.

Key Results

The stereochemistry of sesquiterpene lactone ring junctions helped to explain variation in plant herbivore resistance. Plants producing cis-fused sesquiterpene lactones experienced significantly higher damage than plants producing trans-fused sesquiterpene lactones. Experiments manipulating herbivore damage above and below ambient levels found that herbivore damage was negatively correlated with plant fitness. This pattern translated into significant fitness differences between chemotypes under ambient levels of herbivore attack, but not when attack was experimentally reduced via pesticide.

Conclusions

To our knowledge, this work represents only the second study to examine sesquiterpene lactones as defensive compounds in the field, the first to document herbivore-mediated natural selection on sesquiterpene lactone variation and the first to investigate the ecological significance of the stereochemistry of the lactone ring junction. The results indicate that subtle differences in stereochemistry may be a major determinant of the protective role of secondary metabolites and thus of plant fitness. As stereochemical variation is widespread in many groups of secondary metabolites, these findings suggest the possibility of dynamic evolutionary histories within the Asteraceae and other plant families showing extensive stereochemical variation.     

Desangeloylshairidin,a sesquiterpene lactone from Guillonea scabra

From the roots of Guillonea scabra a new sesquiterpene lactone has been isolated. Its structure has been established by spectroscopic means as desangeloylshairidin.     

Sesquiterpene lactones of diploid and tetraploid Ambrosia camphorata

Diploid and tetraploid specimens of Ambrosia camphorata have distinct sesquiterpene lactone patterns; however, no direct correlation between chemistry and morphological patterns is detectable.     

Sesquiterpene lactone patterns in diploid and polyploid Ambrosia dumosa

Diploid, tetraploid and hexaploid populations of Ambrosia dumosa yielded several different sesquiterpene lactone patterns. The distribution of chemical complements is useful in relating the different levels of this polyploid series.     

Mariolin,a germacranolide from Anacyclus radiatus

A new sesquiterpene lactone, the germacranolide mariolin, was isolated from the aerial part of Anacyclus radiatus along with several known compounds. The structure of mariolin was determined by spectroscopic methods.     

Angeloylcumambrin-B,an antimicrobial sesquiterpene lactone from Chrysanthemum ornatum var. Spontaneum

Angeloylcumambrin-B, a new antimicrobial guaianolide sesquiterpene lactone, was isolated from Chrysanthemum ornatum and the structure was determined by a combination of chemical and physical methods.     

Oxepane diterpenoids sesquiterpene lactones from ‘zoapatle’ (montanoa tomentosa), a mexican plant with oxytocic activity

Investigation of the ‘tea’ prepared from the leaves of ‘zoapatle’ (Montanoa tomentosa), resulted in the isolation of the known biologically active oxepane diterpenoids zoapatanol and montanol, the known sesquiterpene lactones zoapatanolide A, C and D as well as two new biologically active oxepane diterpenoids and a new sesquiterpene lactone. The structures of the new compounds were established by spectroscopic methods.     

Quantitative variation of the sesquiterpene lactones and chromenes of encelia farinosa

The components of the two major classes of natural products of the composite Encelia farinosa, sesquiterpene lactones and benzopyrans/benzofurans (chromenes), were resolved and quantified by high performance liquid chromatography. Geographic variation was examined over a range of mesic and xeric populations from California and Arizona (USA). The concentration of farinosin, a sesquiterpene lactone, varies significantly between individuals and seasonally within individuals. Ontogenetic comparisons revealed interpopulation variations within sesquiterpene lactones and chromenes. A geographic survey suggests the presence of two putative chemical races which vary in the amounts of sesquiterpene lactones and chromenes present. The adaptive significance of this quantitative variation is discussed.