Neue germacren-derivate aus Senecio-arten

From the succulent Senecio species, S. cylindricus, eight new germacrene derivatives were isolated, while S. erosus afforded two new furanoeremophilones. Six further species only contain known compounds. The chemotaxonomic importance of these findings are briefly discussed.     

Sesquiterpene and diterpene derivatives from Solidago species

The investigation of four Solidago species afforded, in addition to known compounds, four new caryophyllene derivatives, two eudesmanes, two abietanes, a clerodane, two labdanes, three kauranes and an anol angelate. The structures were elucidated by spectroscopic methods and by some chemical transformations. While the diterpenes isolated are widespread in the genus Solidago, the sesquiterpenes have not been obtained before from any species. The overall picture of the large genus, however, is relatively uniform.     

Three cadinene derivatives and a prostaglandin-like acid from Chromolaena species

An investigation of the aerial parts of Chromolaena chasleae afforded a prostaglandin-like acid, whose structure followed from the ¹H NMR spectral data and from the reaction with periodate, which afforded a hemiacetal. From a new Chromolaena species, three novel cadinene derivatives were isolated, which were closely related to those isolated previously from this genus.     

Labdane derivatives from hemizonia species

The investigation of three Hemizonia species afforded in addition to known compounds seven new labdane derivatives, all derived from labd-13-en-15-ol. The absolute configuration of these diterpenes was determined by degradation of the triol by periodate cleavage, which afforded a known norditerpene ketone. From H. fitchii two new chromene esters and the cis-isomer of a known coumarate were isolated. H. congesta afforded in addition to labdane derivatives a hydroxycubebol.     

Neue phloroglucin-derivate aus Leontonyx-arten sowie weitere verbindungen aus vertretern der tribus inuleae

The investigation of several South African species of the tribe Inuleae afforded in addition to known compounds 16 new constituents. From Leontonyx a group of 9 new phloroglucinol derivatives, from Stoebe species two new p-hydroxyacetophenone, two thymol and two coumaric acid derivatives and from Relhania a new euparine-derivative were isolated. The structures are elucidated mainly by spectroscopic methods. The chemotaxonomic aspects are discussed briefly. The phloroglucinol derivatives, which in part are derived from geraniol, seem to be especially characteristic.     

Heliangolides,and nerolidol and p-hydroxyacetophenone derivatives from Calea species

A new Calea species afforded a heliangolide, closely related to niveusin C, while from Calea teucrifolia two new nerolidol derivatives and eight p-hydroxyacetophenone derivatives were isolated. The structures were elucidated by spectroscopic methods and a few chemical transformations. The spectral data of 8β-angeloylatripliciolide, the main constituent of C. teucrifolia, are also included. The chemotaxonomic situation is discussed briefly.     

Sesquiterpenes and acetylenes from Argyranthemum adauctum ssp. jacobaeifolium

The roots of Argyranthemum adauctum ssp. jacobaeifolium, a rare endemic from Gran Canaria, afforded two new derivatives of the aromatic acetylene frutescin and 8-isovaleryloxymyrcene, while the aerial parts gave a new bisabolol derivative. Furthermore several known compounds were isolated. The structures were elucidated by high field ¹H NMR spectroscopy and a few chemical reactions.     

The first acetylenic monoterpene and other constituents from Senecio clevelandii

The aerial parts of Senecio clevelandii afforded three new monoterpene lactones, one of them being the first acetylenic monoterpene to be isolated, a C-14 acetylenic angelate, a tetrahydroquinol ester and several known compounds, among them the tricyclic precursor of the polycyclopentanoide sesquiterpenes.     

Homogeranyl nerol derivatives and a melampolide from Smallanthus glabratus

The investigation of the aerial parts of Smallanthus glabratus from two locations afforded the same known compounds but some additional new compounds which were not present in both collections. From the first location typical melampolides, one of them not isolated previously, and two homoditerpenes were isolated. The material from the second location gave four closely related homoditerpenes and two geranyl nerol derivatives from which the homoditerpenes were derived. The structures were elucidated by high field ¹H NMR spectroscopy. Chemotaxonomic aspects are discussed briefly.     

Beyerene derivatives and other terpenoids from Stevia aristata

The aerial parts of Stevia aristata afforded in addition to known compounds two new germacranolides, a melampolide, a 4Z-melampolide and two beyerene derivatives. From the roots a new dihydrolongipinene derivative was isolated while the aerial parts of Stevia andina gave the E/Z-isomers of austroinulin and 6-desoxyaustroinulin. The absolute configuration of these typical diterpenes is discussed.     

Germacranolides from Gochnatia vernonioides

The aerial parts of Gochnatia vernonioides afforded, in addition to dehydrocostus lactone, zaluzanin C and desacetyllaurenobiolide angelate, 14 further sesquiterpene lactones, ten 8, 12-and three 6,12-germacranolides as well as one eudesmanolide and three bisabolene derivatives. The structures were elucidated by spectroscopic methods and by comparing the data with those of closely related compounds. 8α-Angeloyloxytaraxic acid underwent an unusual autocatalysed cyclisation while the usual Cope rearrangement was not observed.     

Eudesman-12,8β-olides and other terpenes from Artemisia species

The aerial parts of Artemisia iwayomogi afforded, in addition to already known terpenes, eleven new cudesmanolides whereas four new guaianolides were found in A. gmelinii. No sesquiterpene lactones were detected in the aerial parts of A. santolinifolia which afforded two new nerolidol derivatives besides several other already known compounds. From A. caerulescens var. cretacea six eudesmanolides were isolated, one of which has not been reported previously. The structures were elucidated by high field ¹H NMR spectroscopy and chemical transformations. The chemotaxonomic significance of sesquiterpene lactones within the section Abrotanum and the subgenus Seriphidium is briefly discussed.     

Poskeanolide,a seco-germacranolide and other sesquiterpene lactones from Vernonia species

The aerial parts of Vernonia cinerea, collected in Costa Rica, gave four new hirsutinolides while a sample from Malawi afforded glaucolide E and two related lactones. From V. poskeana a seco-germacranolide biogenetically closely related to a new glaucolide was isolated. The investigation of two Critoniopsis species gave in addition to known lactones a further glaucolide and a vernopatensolide. A related species, V. flexipappa, only gave glaucolide B. The structures were elucidated by highfield NMR spectroscopy.     

Cuauthemone sesquiterpenoids from Blumea alata

The investigation of five Blumea species afforded, in addition to known compounds, several cuauthemone derivatives, most of them being 7,11-epoxides, some thymol derivatives, an eremophilane epoxide and a himachalane diol. From Pterocaulon virgatum a further himachalane derivative was isolated. The structures were elucidated by spectroscopic methods and in part by partial synthesis.     

Oxygenated nerolidol derivatives from Artemisia alba

From the aerial parts of Artemisia alba of Calabrian origin, five oxygenated nerolidol derivatives were isolated, two of them bearing hydroperoxyl groups. Structures were elucidated by spectral data and chemical reactions. Acetylation of the major hydroperoxyl constituent afforded a tris-nor aldehydic derivative as a result of loss of acetone from an unstable intermediate perester. An internally consistent set of ¹³C NMR assignments for the natural products and some derivatives is presented.     

Neue sesquiterpene,triterpene, flavanone und andere aromatische verbindungen aus Flourensia heterolepis

The investigation of a further Flourensia species afforded in addition to already known compounds 12 new sesquiterpene acids isolated as their methyl esters, a new eudesmane diol, four lupane derivatives and two flavanones, two cinnamic acid derivatives, also isolated as methyl esters and a ketone. The structures are elucidated mainly by spectroscopic methods and by some chemical transformations. Several of the compounds isolated are more or less similar to those isolated from other Flourensia species; the considerable amounts of eudesmanes, however, are unusual. The overall picture of the genus is still relatively uniform. Close relationships to Helianthella are obvious, while to Helianthus, placed in the same subtribe, no clear relations are visible.     

Iridoid glucosides in Griselinia, Aralidium and Toricellia

From three of five investigated species of Griselinia a new iridoid glucoside, griselinoside, was isolated. It was found to be present also in foliage of Aralidium pinnatifidum and Toricellia angulata, accompanied in the former by aralidioside another novel iridoid glucoside. The structures and absolute configurations of the two iridoids were elucidated by NMR spectroscopy and chemical conversions. From G. littoralis and T. angulata the glucosides magnolioside and syringoside respectively were isolated. ¹³C NMR spectra are given for thirteen iridoid derivatives.     

Eudesmanolides and diterpenes from Wedelia trilobata and an ent-kaurenic acid derivative from Aspilia parvifolia

The reinvestigation of the aerial parts of Wedelia trilobata afforded, in addition to known compounds, six new eudesmanolides, two ent-kaurenic acid derivatives as well as a degraded one. A corresponding hydroxy compound was present in Gnaphalium undulatum. From Aspilia parvifolia new ent-kaurenic acid epoxides were isolated. The structures were elucidated by spectroscopic methods. The chemotaxonomic situation is discussed briefly.     

Furanoheliangolides from two Eremanthus species and from Chresta sphaerocephala

The investigation of Eremanthus crotonoides afforded in addition to known compounds three new furanoheliangolides, while from E. glomerulatus six new furanoheliangolides and eremantholides were isolated. From the aerial parts of Chresta sphaerocephala a new guaianolide was obtained, while the roots contained known furanoheliangolides. The chemotaxonomy of the subtribe Lychnophorinae is discussed briefly.     

Obliquin derivatives and other constituents from Australian Helichrysum species

The investigation of three Australian Helichrysum species afforded in addition to known compounds three new obliquin derivatives, eight cinnamic acid derivatives, a tremetone derivative, a styrene derivative, two lignans, two caryophyllene derivatives and an azulene. The structures were elucidated by highfield ¹H NMR.