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.     

Neue phloroglucin-derivate aus Helichrysum natalitium und Helichrysum bellum

Helichrysum natalitium afforded four new phloroglucinol derivatives, while from H. bellum two further compounds of this type have been isolated; H. platypterum yielded two known derivatives. The new structures were elucidated by spectroscopic methods and some chemical transformations. The chemotaxonomical situation is briefly discussed.     

Caffeic acid derivatives isolated from the aerial parts of Galinsoga parviflora and their effect on inhibiting oxidative burst in human neutrophils

Four new caffeoyl -glucaric and -altraric acid derivatives along with eleven known compounds were isolated from aerial parts of Galinsonga parviflora. Their structures were elucidated by high-resolution spectroscopic studies. The four new compounds were determined as being 2,3,4,5-tetracaffeoylglucaric acid (1), 2,4,5-tricaffeoylglucaric acid (2), 2,3,4- or 3,4,5-tricaffeoylaltraric acid (3) and 2,3(4,5)-dicaffeoylaltraric acid (4). A reliable criterion for the determination of the linkage position of caffeic acids moieties in glucaric acid derivatives has been proposed, on the basis of detailed analysis of the respective J-couplings, including substitution and solvent influence on the observed values. All hexaric acids derivatives appeared as inhibitors of reactive oxygen species production by stimulated neutrophils.     

Germacrene derivatives and other sesquiterpenes from Senecio species and Lordhowea insularis

From Senecio galpinii six new highly oxygenated germacrene derivatives were isolated, while S. coronatus afforded in addition to known cacalol derivatives two new ones. This species also contained a rare tricyclic sesquiterpene angelate, so far only isolated from one species. From the aerial parts of S. pleistocephalus an angelate derived from cadinene was isolated, while Lordhowea insularis (Benth.) B. Nord. afforded farnesyl angelate, which was reported previously. The structures were elucidicated mainly by high field ¹H NMR spectroscopy.     

Eudesmane derivatives from Verbesina species

The investigation of seven Verbesina species afforded, in addition to known compounds, several new eudesmane and germacrane derivatives, all bearing a cinnamate or derivatives as residue. Furthermore, a new bisabolene aldehyde and two acetophenone derivatives were isolated. The structures were elucidated mainly by spectroscopic methods and some chemical transformations. The chemotaxonomic situation is discussed briefly.     

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.     

Three diterpenes from Conyza podocephala

The investigation of Conyza podocephala afforded, in addition to known compounds, two clerodane derivatives and a dihydroxyfarnesyl methylfuran. Furthermore two new resorcinol derivatives were isolated. The structures were elucidated by spectroscopic methods and by chemical transformations. The chemotaxonomic situation within the genus is discussed briefly.     

Neue pyron-derivate aus Helichrysum-arten

The investigation of five further Helichrysum species afforded in addition to known compounds nine α-pyrone derivatives all also being phloroglucinol derivatives. Furthermore, a new toxol derivative has been isolated. The structures were elucidated by extensive NMR studies and by some chemical transformations. The chemotaxonomic situation is discussed briefly.     

A daucanolide further farnesene derivatives from Ageratum fastigiatum

A reinvestigation of Ageratum fastigiatum afforded, in addition to known compounds, several new farnesene derivatives including some tetrahydropyrane derivatives. Furthermore a sesquiterpene lactone derived from daucane and a minor derivative of the ent-labdanes isolated previously were isolated. The structures were elucidated by spectroscopic methods.     

Arbutin derivatives from the buds of Vaccinium dunalianum and their MS/MS spectrometric fragmentations

Four arbutin derivatives were isolated from the buds of Vaccinium dunalianum in which 4-hydroxyphenyl-6′-(3''-O-β-D-glucopyranosyl-4''-hydroxycinnamoyl)-O-β-D-glucopyranoside (1) was a new compound. The structure of the new compound was determined on the basis of NMR and HR-ESI-MS data. All the arbutin derivatives were subjected to the MS/MS analyses from which the MS/MS spectrometric fragmentations were summarized.     

New labdane derivatives from Madia sativa

The aerial parts of Madia sativa afforded, in addition to known compounds, two labdane derivatives whose structures were elucidated by spectroscopic methods. The absolute configuration was determined by chemical transformations. From the roots a new tremetone derivative was isolated. The constituents indicated close relationships of Madia to Hemizonia.     

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.     

Neue labdan-derivate aus Aristeguietia buddleaefolia

The aerial parts of Aristeguietia buddleaefolia afforded, in addition to known compounds, three new diterpenes, all being 12, 13-E-abienol derivatives. A further diterpene turned out to be jhanidiol-18-O-acetate, isolated earlier from an Ageratina species. Furthermore two derivatives of hydroxy dihydroconiferyl alcohol are present. The structures were elucidated by spectroscopic methods and by some chemical transformations.     

Further silphinene derivatives from Cineraria geifolia var. glabra

A reinvestigation of the sesquiterpenes from the aerial parts of Cineraria geifolia var. glabra afforded eight new silphinene derivatives. One of these compounds had been isolated previously but its structure had not been elucidated with certainty. The stereochemistry of a corresponding isovalerate from Callilepis salicifolia has to be revised.     

Neue labdan-derivate und andere inhaltsstoffe aus Relhania acerosa

The investigation of Relhania acerosa afforded, in addition to known compounds, three new labdane derivatives, two of which are esterified with succinic acid and one which has an anomalous carbon skeleton. Furthermore, several new aromatic compounds are isolated, which are most probably degradated thymol derivatives. The structures are elucidated by spectroscopic methods and by some chemical transformations. The stereochemistry of one of the new labdanes has been established by a partial synthesis. The chemotaxonomic situation is briefly discussed.     

Two new quinic acid derivatives from the fruits of Chaenomeles speciosa

Two new quinic acid derivatives (1, 2), together containing eighteen (3–20) known compounds, were isolated from the fruits of Chaenomeles speciosa. Spectroscopic methods and previous data retrieved from the literature were used to determine the chemical structures of the compounds. Among the compounds, quinic acid derivatives (3, 4, 6, 7), phenolic acid compounds (8, 10, 11) and catechin derivatives (18, 19, 20) were isolated for the first time from the family Chaenomeles. The chemotaxonomic significance of the compounds was also discussed.     

Chromones and flavans from Marshallia obovata

An investigation of Marshallia obovata afforded, in addition to known thymol derivatives, one new ester. Furthermore six new chromone derivatives, all prenylated, were present together with the known spathelia chromene. The main constituent was a flavan already isolated from M. grandiflora but five new flavans were also isolated. Besides other widespread compounds a tetraester of inositol was isolated in minute amounts. All the structures were elucidated by spectroscopic methods or chemical transformations. Surprisingly, even the main 4-methoxyflavan could be split by periodic acid.     

Novel tetrahydrofuran derivatives from Trigonostemon howii with their potential anti-HIV-1 activities

A novel tetrahydrofuran derivative, trigonohowine (1), together with five known tetrahydrofuran derivatives (2–6), were isolated from the stems and leaves of Trigonostemon howii. The structure of 1 was elucidated by extensive spectroscopic methods and the known compounds were identified by comparisons with the data reported in literature. Among them, trigonohowine (1) represents the first example of a new type of tetrahydrofuran derivative, possessing an unprecedented carbon skeleton containing 23 carbon atoms on the carbon skeleton and the known compouds (2–6) are rare tetrahydrofuran derivatives in the plant kingdom with various carbon skeletons. All isolated compounds were evaluated for their anti-HIV-1 activities. Compounds 1–6 showed significant anti-HIV-1 activities with EC₅₀ ranged from 0.08 to 1.03 µM. These findings suggest that the discoveries of these tetrahydrofuran derivatives with significant anti-HIV-1 activities isolated from T. howii could be of great importance to the development of new anti-HIV agents.     

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.     

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.