Sesquiterpene lactones of Montanoa guatemalensis and Montanoa tomentosa subsp. Xanthiifolia

New 4,5-epoxygermacra-12,6β-olides from Montanoa guatemalensis and a Guatemalan disjunct collection of M. tomentosa subsp. xanthiifolia are reported. These compounds were unlike those from the 10 other Mexican collections of M. tomentosa previous investigated.     

Zoapatanolides C and D,two guaianolides from Montanoa tomentosa

Further investigation of Montanoa tomentosa afforded two new guaianolides as well as the known pumilin and the previously isolated heliangolide zoapatanolide A. The structures were established on the basis of spectroscopic studies and chemical evidence.     

Germacra-12,6β-olides from Montanoa revealii and M. mollissima

Montanoa revealii and M. mollissima yielded a series of germacra-12,6β-olides similar to those previously reported from M. hibiscifolia and M. pteropoda.     

Two further 6,12-cis-germacranolides from Montanoa tomentosa subsp. xanthiifolia

The aerial parts of Montanoa tomentosa subsp. xanthiifolia gave two further 6,12-cis-germacranolides while the roots contained large amounts of kaurane derivatives.     

Four eudesmanolides from Montanoa frutescens

Chemical analysis of Montanoa frutescens afforded the known sesquiterpene lactones montafrusins A and B, as well as four new eudesmanolides which we have named montafrusins C, D, E and F. The structures of the new compounds were established by spectroscopic methods.     

Sesquiterpene lactones from Viguiera deltoidea

Three sesquiterpene lactones, 2′,3′-dihydroniveusin-A, 2′,3′-dihydroniveusin-B and 3-acetylchamissonin, were isolated from the dichloromethane extract of leaves of Viguiera deltoidea. The structures were established on the basis of physical and spectroscopic data and that of 3-acetylchamissonin was also confirmed by X-ray analysis.     

Zoapatanolide A and B,two new heliangolides from Montanoa tomentosa

The re-investigation of Montanoa tomentosa afforded, in addition to known diterpenoids of the kaurene class, two new sesquiterpene lactones, zoapatanolide A and B, of the heliangolide type.     

Three bourbonenolides and other sesquiterpene lactones from two vernonia species

A re-investigation of V. arkansana afforded several new sesquiterpene lactones, three bourbonenolides, obviously closely related to those isolated from this plant previously, a glaucolide and a methoxy derivative most probably formed by fragmentation of the corresponding bourbonenolide. From V. profuga in addition to known lactones a new guaianolide was isolated. The biogenetic relationships of the Vernonia sesquiterpene lactones are discussed briefly.     

Minor sesquiterpene lactones of Helianthus pumilus

The isolation of four known and two new germacradienolides and one known heliangolide from Helianthus pumilus, in addition to the previously report     

Two sesquiterpene and three diterpene lactones from Acanthospermum australe

The aerial parts of Acanthospermum australe afforded two new sesquiterpene lactones, an acid and a cis,cis-germacranolide, as well as three diterpene lactones of a new type, most probably formed by intermolecular nucleophilic attack of the carboxyl group of an acid epoxide derived from geranylgeraniol. The structures were proposed on the basis of spectroscopic studies.     

Further sesquiterpene lactones from Helianthus maximiliani

By using HPLC, a new melampolide, a known heliangolide and three known germacrolides were isolated as minor constituents from a north central Texas population of Helianthus maximiliani. In an earlier report, we identified the germacrolide desacetyleupaserrin as the principal sesquiterpene lactone from this population.     

New germacrolide- and heliangolide-type sesquiterpene lactones from Melampodium linearilobum

Chemical analysis of Melampodium linearilobum yielded, besides coumarin, seven germacrolide-type sesquiterpene lactones, linearilobin A to G and two heliangolides, linearilobin H and I. All new sesquiterpene lactones are oxygenated at C-14 and C-15 and differ by the number and types of ester moieties at C-8, C-14 and C-15. M. linearilobum represents the first species within the genus known to produce germacrolides and heliangolides instead of the more common melampolides.     

Two sesquiterpene lactones from Centaurea canariensis

From the aerial part of Centaurea canariensis three sesquiterpene lactones were isolated: cynaropicrin, deacylcynaropicrin and aguerin A. The same species, grown from seed, yielded cynaropicrin, deacylcynaropicrin and aguerin B. The guaianolides aguerin A and B are reported for the first time. Aguerin B was subsequently found to be present in Centaureana linifolia, C. canariensis (var subspinnata) and C. sventenii.     

Sesquiterpene lactones from a texas population of Helianthus maximiliani

A population of Helianthus maximiliani from south-central Texas was shown to have a sesquiterpene lactone chemistry which was completely different from that reported for collections of this species from Kansas and north-central Texas. A series of five new guaianolides, two germacrolides (trans, trans-1(10),4(5)-germacradienolides), one of which is new, and a known labdane diterpene acid were isolated from a chloroform extract. Structures were determined by spectral and chemical methods. The structure of one guaianolide had been previously determined by X-ray crystallography.     

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     

Two guaianolides from calea solidaginea

The isolation and structure elucidation of two new guaianolides, solidaginolides A(1) and B(5), from Calea solidaginea are reported. The structures of the new compounds were established by spectroscopic methods.     

Evolution of sesquiterpene lactones in asteraceae

The two basic micromolecular phenomena which accompany the introduction of a novel lineage in angiosperms, vigorous increase in oxidation state of allelochemics and reduction of the number of major biosynthetic routes, are shown to characterize the evolutionary development of sesquiterpene lactones in tribes of Asteraceae.     

Sesquiterpene lactones of Eupatorium scabridum

Eupatorium scabridum, a hybrid biotype presumed to arise by hybridization of E. rotundifolium and E. semiserratum furnished anti-tumor sesquiterpene lactones characteristic of the putative parents.