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.     

Clerodanes from solidago virgaurea

The isolation and structure determination of four known and eight new cis-clerodane lactones from the aerial parts of Solidago virgaurea are described.     

8-Hydroxypegolettiolide,a sesquiterpene lactone with a new carbon skeleton and further constituents from Pegolettia senegalensis

The investigation of Pegolettia senegalensis afforded several new sesquiterpene lactones, eight cis-6,12-germacra-trans,trans-1(10),4,11-trienolides, five cis-6,12-eudesmanolides, two elemanolides, 8,14-cyclogermacra-1(10),4,7(11)-trien-6,12-olide with a new carbon skeleton, three germacra-1(10),4,11(13)-trien-12-oic acids with ester residues at C-8, 18-hydroxygeranyl nerol, 1,3-dihydroxyoctadecane and a mixture of esters of 3,4-dihydroxy-dihydrocinnamyl alcohol. The structures were elucidated by high field ¹HNMR spectroscopy and some chemical transformations. The C-10 configuration of 6,12-cis-eudesmanolides from Calostephane divaricata and Inula crithmoides most likely has to be corrected. The chemotaxonomic situation of the genus Pegolettia and biogenetic considerations are discussed briefly.     

Neue sesquiterpenlactone aus Stokesia laevis

The investigation of Stokesia laevis afforded in addition to known compounds five new sesquiterpene lactones, four hirsutinolides and one guaianolide. The structures are very similar to those isolated from several Vernonia species. Since hirsutinolides have only been previously isolated from this latter genus, these results suggest that Stokesia may be closely related to Vernonia.     

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.     

Sesquiterpenlactone und polyine aus der gattung Arctotis

The South African genus Arctotis contains two polyynes sometimes together with diterpenes and sesquiterpene lactones, four of which are new. The structures have been elucidated by spectroscopic methods.     

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.     

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.     

Cytotoxic activity of acetogenins and styryl lactones isolated from Goniothalamus undulatus Ridl. root extracts against a lung cancer cell line (COR-L23)

An investigation of the chemical constituents in a dichloromethnae extract of Goniothalamus undulatus root led to the isolation of three known styryl lactones (5-acetoxyisogoniothalamin oxide, O-acetylaltholactone and altholactone), and four known annonaceous acetogenins (annonacin, cis-annonacin, goniothalamicin and cis-goniothalamicin). These compounds were subjected to a sulphorhodamine B (SRB) cytotoxicity assay against human large cell lung carcinoma (COR-L23), and normal human fetal fibroblast (MRC-5), cell lines. The isolated acetogenins showed higher cytotoxic activity against COR-L23 compared to the styryl lactones, with IC₅₀ values in the range of 0.5-1.7 μM and 7.4-15.4 μM, respectively. A similar pattern of cytotoxicity was also observed against the other cell line (MRC-5); acetogenins IC₅₀ values were in the range of 11.8-31.4 μM, and those for styryl lactones were in the range of 48.7-102.8 μM. This is the first report of a bioassay-guided isolation of chemical constituents from G. undulatus and on cytotoxic studies of the isolated compounds using these particular lung cancer cell lines.     

Sesquiterpene lactones from Eremanthus species

The investigation of three Eremanthus species afforded, in addition to known compounds, several new sesquiterpenelactones, a cumambrin B isobutyrate, four lactones related to the eremantholides, two to zexbrevin and one to goyazensolide. Furthermore, a new coniferyl alcohol derivative was isolated. The overall picture of the genus is very uniform. The occurrence of eremanthine and germacranolides with a furanone ring seems to be especially typical.     

Neue furanoeremophilane und weitere inhaltsstoffe aus südafrikanischen Senecio-arten

The investigation of further 27 South African and a few other Senecio species afforded in addition to known compounds 18 new furanoeremophilanes, most of them being cacalol derivatives, two new lactones, a new eudesmane derivative and four acyl pyrrole derivatives. The structures are elucidated by spectroscopic methods mainly. The chemical results on more than 140 species now available indicate much of chemotaxonomic interest. Together with the chemical data on related genera, the taxonomic situation of the subtribe Senecioninae is discussed in connection with the proposed new classification. The chemical data are in good agreement with this new arrangement.     

cis-Clerodane diterpenoids from the Chinese liverwort Scapania parva Steph.

Three undescribed cis-clerodane lactones, scapanialides A–C (1–3), and a new cis-clerodane furano-diterpenoid, scaparvin F (4), were isolated from the Chinese liverwort Scapania parva Steph. Scapanialide B (2) is the first cis-clerodane diterpenoid with a bicyclo[5.4.0]undecane skeleton from liverworts. Their structures including the absolute configurations were determined by extensive analysis of multidimensional NMR spectroscopy and TDDFT CD calculations, together with crystal X-ray diffraction measurements. The cytotoxicity of compounds 1–4 was preliminary tested against the Hela and MCF-7 cell lines.     

New sesquiterpene lactones from Inula species

An investigation of Inula helenium, I. royleana, I. salicina and I. bifrons afforded in addition to known sesquiterpene lactones 20 new lactones, the eudesmanolides 3, 6 and 8–12, the germacranolides 14–18 and 20–22, the guaianolides 23 and 25, the pseudoguaianolide 26, the xanthanolides 28 and 32 and the cyclopropane analogue 30. Structures and configurations of these new compounds were established by extensive PMR studies and by some chemical transformations. Some of the investigated species contain besides the widely distributed pentaynene 33 several known thymol derivatives together with a new one (40).     

Neue,abgewandelte pseudoguajanolide aus Psilostrophe villosa

Investigation of the North American species Psilostrophe villosa afforded, in addition to known compounds, five new sesquiterpene lactones, which all turn out to be modified pseudoguaianolides, most of them closely related to hymenolide. However, one of the lactones is a new type of nor-pseudoguaianolide. Furthermore a new monoacetylated borneol-β-D-glucoside is present. The chemotaxonomic situation is discussed briefly.     

Sesquiterpene lactones from dicoria canescens

Dicoria canescens from Baja California, Mexico afforded the known monoterpene glucoside, (?)-cis-chrysanthenol O-β-d-glucopyranoside, ivalbatin, a xanthanolide and two new sesquiterpene lactones, 4-dihydroivalbatin (dicorin) and 11β, 13-tetrahydrovalbatin (dihydrocorin).     

Conversion of 2-Fluoromuconate to cis-Dienelactone by Purified Enzymes of Rhodococcus opacus 1cp

The present study describes the ¹⁹F nuclear magnetic resonance analysis of the conversion of 3-halocatechols to lactones by purified chlorocatechol 1,2-dioxygenase (ClcA2), chloromuconate cycloisomerase (ClcB2), and chloromuconolactone dehalogenase (ClcF) from Rhodococcus opacus 1cp grown on 2-chlorophenol. The 3-halocatechol substrates were produced from the corresponding 2-halophenols by either phenol hydroxylase from Trichosporon cutaneum or 2-hydroxybiphenyl 3-mono-oxygenase from Pseudomonas azelaica. Several fluoromuconates resulting from intradiol ring cleavage by ClcA2 were identified. ClcB2 converted 2-fluoromuconate to 5-fluoromuconolactone and 2-chloro-4-fluoromuconate to 2-chloro-4-fluoromuconolactone. Especially the cycloisomerization of 2-fluoromuconate is a new observation. ClcF catalyzed the dehalogenation of 5-fluoromuconolactone to cis-dienelactone. The ClcB2 and ClcF-mediated reactions are in line with the recent finding of a second cluster of chlorocatechol catabolic genes in R. opacus 1cp which provides a new route for the microbial dehalogenation of 3-chlorocatechol.     

Neue sesquiterpenlactone und thymol-derivate aus Inula-arten

The investigation of three Inula species affords, besides known compounds, two new sesquiterpene lactones and two new thymol derivatives. The chemotaxonomic situation in this genus is still very complicated.     

Neuartige sesquiterpenlactone und neue acetylenverbingen aus Athanasia-arten

The investigation of two further South African Athanasia-species afforded, in addition to known compounds, sixteen new ones, ten guaianolides, an eudesmanolide, three sesquiterpenes, a new enediynene and a phenylpropane derivative. The structures were elucidated by extensive NMR-studies. Three of the lactones are very unusual in having an endoperoxide bridge; their structures, however, were elucidated only indirectly. These further chemical results on Athanasia again add support to the idea that these species might be better placed in the genus Pentzia.     

Seven guaianolides from Eupatorium chinense

Two allyl hydroperoxy guaianolide sesquiterpene lactones (peroxyeupahakonin-A and -B) and five new guaianolides (eupahakonin-A and -B, eupahakonenin-A and -B, and eupahakonesin) were isolated from E. chinense and characterized. The allyl hydroperoxy sesquiterpene lactones were characterized by spectral and chemical methods. They were prepared chemically by photosensitized oxygenation of eupahakonin-A.     

Neue acetylenverbindungen aus Leucanthemum-arten und revision der struktur eines germacranolids

The investigation of three Leucanthemum species afforded, in addition to known compounds, two new C₁₇-acetylenes, a new isovalerate, two phenolic acetylenes, a C₁₂-isobutylamide and a new farnesol derivative. Chrysanthemum ferulaceum contains deacetyllaurenobiolide (spiciformin) which is identical with a lactone from Inula britannica previously assumed to be a cis, cis-germacranolide.