Seven germacranolides and four eudesmanolides from Tithonia rotundifolia

The aerial parts of Tithionia rotundifolia afforded, in addition to two known sesquiterpene lactones, eleven new ones, seven germacranolides and four eudesmanolides. The structures were determined by ¹H NMR spectroscopy.     

Allenic germacranolides,bourbonene derived lactones and other constituents from Vernonia species

An investigation of seven Vernonia species, mainly from northern Brazil, afforded in addition to known compounds three new unusual sesquiterpene lactones with an allenic group. Intensive NMR studies fully established the structures. Furthermore, two lactones derived from bourbonene, two new glaucolides, a new furansesquiterpene, a nerolidol derivative and two other sesquiterpenes derived from eudesmane were isolated. The biogenetic relationships of the sesquiterpene lactones present in Veronia species as well as the chemotaxonomic aspects are discussed.     

Further eudesmanolides and xanthanolides from Telekia speciosa

The re-investigation of the aerial parts of Telekia speciosa afforded five new sesquiterpene lactones, two eudesmanolides and three xanthanolides, all closely related to those isolated before from this species or from related genera. The structures were elucidated by ¹H NMR spectroscopy.     

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.     

Cadinenes and other metabolites from Verbesina sphaerocephala A. Gray

The phytochemical study of the aerial parts of Verbesina sphaerocephala A. Gray afforded six sesquiterpene lactones of cadinene type, five of them described for the first time, along with known phenyl propanoids, terpenoids, and phenolic compounds. Structures on new compounds were elucidated by spectroscopic techniques including CD and X-ray analyses, and known compounds were identified by comparing their spectral data with those previously reported. Cadinene-like sesquiterpene lactones could be characteristic metabolites of V. sphaerocephala.     

Glaucolide-like sesquiterpene lactones from Cotula cinerea

The aerial parts of Cotula cinerea gave, in addition to widespread compounds, a characteristic diacetylenic spiroketal enolether and several sesquiterpene lactones, three of them being glaucolide-like lactones. The structures were elucidated by highfield ¹H NMR spectroscopy.     

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.     

Anticancer sesquiterpene lactones of Michelia compressa (magnoliaceae)

Investigation of the cytotoxic active components of Michelia compressa afforded two new cytotoxic sesquiterpene lactones, michelenolide and micheliolide. Parthenolide, costunolide, santamarine, reynosin and liriodenine were also isolated and exhibited cytotoxic activity. The known sesquiterpene lactones, lanuginolide and dihydroparthenolide, were isolated but were not active. Two other new inactive sesquiterpene lactones, compressanolide and dihydroreynosin, were also obtained. The structures of michelenolide and micheliolide were confirmed by partial synthesis from parthenolide and the structure of compressanolide by partial synthesis from dihydroparthenolide.     

Pungent sesquiterpene lactones of the european liverworts Chiloscyphus polyanthus and Diplophyllum albicans

The characteristic pungency of the European liverwort, Chiloscyphus polyanthus, is due to a mixture of four sesquiterpene lactones, two new structures ent-5β-hydroxydiplophyllin and ent-3-oxodiplophyllin, and the previously known diplophyllin and diplophyllolide. A new dihydrodiplophyllin, together with the pungent diplophyllolide and diplophyllin, has been isolated from Diplophyllum albicans. Ent-dihydrodiplophyllolides derived from the above pungent diplophyllolides produce intense numbness of the tongue. All pungent sesquiterpene lactones showed inhibitory activity towards the germination and root elongation of rice husks.     

Guaianolides from Centaurea kotschyi

The aerial parts of Centaurea kotschyi (var. kotschyi) afforded, besides three known sesquiterpene lactones, a new derivative of linichlorin B.     

Glaucolides from Vernonia fulta

Four sesquiterpene lactones were isolated from the aerial parts of Vernonia fulta. Spectral characterization showed that three were new and one was known (i.e. glaucolide-B). The biogenetic relationship among these sesquiterpene lactones is discussed briefly.     

Guaianolides from Ainsliaea fragrans

Five sesquiterpene lactones were isolated from Ainsliaea fragrans, two of them being new.     

Systematic implications of sesquiterpene lactones in the subtribe melampodiinae

Within the tribe Heliantheae of the Asteraceae, the genetic boundaries of the subtribe Melampodinae have recently been drastically revised by Stuessy. The number of genera within the subtribe has been reduced and new generic groupings have been established. The present study correlates the distribution of sesquiterpene lactones found in these genera with the newly revised subtribal boundaries. The genera Acanthospermum, Melampodium, Polymnia and Sigesbeckia produce predominantly melampolide-type sequiterpene lactones. Limited chemical data support Stuessy's removal of the genera Desmanthodium, Clibadium and Ichthyothere from the subtribe Melampodiinae. The occurrence of melampolide-type sesquiterpene lactones in members of the genera Tetragonotheca (Helianthinae) and Enhydra (Ecliptinae) indicate a possible position of these genera in the Melampodiinae.     

Hirsutinolides,glaucolides and sesquiterpene lactone from Vernonia species

The investigation of nine Vernonia species afforded in addition to known sesquiterpenes 28 new ones. The structures were elucidated by high field ¹H NMR spectroscopy and the configurations were determined by NOE difference spectroscopy and, in one case, by X-ray analysis. The results indicated that configurations of several previously reported sesquiterpene lactones have had to be revised. In addition to known types two new ones, the jalcaguaianolides and the vernojalcanolides, are described. Furthermore some unusual reaction products are presented which, in part, led to some natural occurring lactones.     

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.     

Sesquiterpene lactones and other constituents from Matricaria chamomilla L.

An ethanolic extract of the aerial parts of Matricaria Chamomilla L. collected at Oued Tonga near El-Kala is eastern Argelia yielded two new substances named matricolone and chamolol, together with four known compounds. The structure of the new compounds were determined by chemical transformations and NMR spectroscopy with ¹H-¹H (COSY and ROESY), ¹H-¹³C (one bond and long range correlations) two dimensional experiments. The results obtained indicate the presence of sesquiterpene lactones of the eudesmanolide, germacranolide and guaianolide types. These products can be considered to be of great interest from a chemotaxonomical point of view for this wild-growing plant, because these types of lactones have not been found together in other Matricaria species.     

Germacranolides from Eupatoriastrum nelsonii

The aerial parts of Eupatoriastrum nelsonii afforded, in addition to known sesquiterpene lactones, four new lactones all closely related to the germacranolides isolated previously from other genera of the tribe Eupatorieae. The structures were elucidated by spectroscopic methods. Chemotaxonomic aspects are discussed briefly.     

Sesquiterpene lactones from the leaves of Magnolia sirindhorniae

Five sesquiterpene lactones, costunolide (1), santamarine (2), reynosin (3), parthenolide (4), and lipiferolide (5), were isolated from the leaves of Magnolia sirindhorniae. Their structures were identified by analysis of spectroscopic data and comparison with those reported in the literature. Compound 5 was isolated from the Magnolia for the first time, and this is the first report of the isolation of the sesquiterpene lactones from M. sirindhorniae.     

Sesquiterpene lactones from Centaurea solstitialis

Eight sesquiterpene lactones were isolated from Centaurea solstitialis (yellow starthistle). They are solstitialin A, repin, subluteolide, acroptilin, janerin, cynaropicrin, and the new lactones solstitiolide and episolstitiolide.     

Melampolides and other germacranolides from Blainvillea dichotoma

The aerial parts of Blainvillea dichotoma afforded, in addition to known compounds, seven new sesquiterpene lactones, four related to elephantin, two melampolides and a further cis,cis-germacranolide. The chemotaxonomic situation is discussed briefly.