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.     

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.     

Furanoheliangolides from Viguiera greggii

Three furanoheliangolide sesquiterpene lactones were isolated from Viguiera greggii, including a novel compound, 1,2-dehydrozexbrevin B, and the previously characterized zexbrevin and zexbrevin B. Structures were determined by spectral methods, chiefly ¹H and ¹³C NMR. Based on present knowledge, there appear to be no major differences between the terpenoid chemistry of Viguiera and that of Helianthus, a genus believed to be very closely related to Viguiera on morphological grounds.     

Five mikanolide derivatives from mikania cynanchifolia and their biogenetic relationships

The investigation of the aerial parts of Mikania cynanchifolia afforded, in addition to miscandenin, five new sesquiterpene lactones, miscandenin-1,2-epoxide, an isomiscandenin and three further dilactones related to mikanolide. The structures of these new compounds were elucidated by high field ¹H NMR spectroscopy. The biogenetic relationships of the sesquiterpene lactones are briefly discussed.     

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.     

Seven sesquiterpene lactones from Inula britannica var. chinensis

Four known sesquiterpene lactones, tomentosin, ivalin, 4-epi-isoinuviscolide and gaillardin, together with three new lactones, inuchinenolides A, B and C, were identified in the whole plant of Inula britannica var. chinensis.     

Germacranolides from Helianthus californicus

Five germacranolide sesquiterpene lactones and a trachylobane diterpene were isolated from the hexaploid species Helianthus californicus. Four of the sesquiterpene lactones are new, including a 1-oxo-3,10-diol without any carbon-carbon double bonds in the main ring whose structure was confirmed by X-ray crystallography. These results require revision of the structures of several previously published compounds. Two of the germacranolides have alkyl ether functions at a position β to a ketone and are believed to be artifacts of the isolation process. Based on terpenoid chemistry, there are no obvious progenitors of H. californicus among the diploid species of Helianthus examined to date.     

Benzoxazinones from Coix lachryma-jobi var. ma-yuen

The absolute configurations of 2-O-β-D-glucopyranosyl-7-methoxy-1,4(2H)-benzoxazin-3-one and three congeners isolated from Coix lachryma-jobi var. ma-yuen were determined by X-ray analysis and chemical correlation as the 2R type. ¹³C NMR spectra of all congeners and coixol were fully assigned.     

Sesquiterpene lactones from the aerial parts of Anthemis arvensis L.

Two known sesquiterpene lactones, antheindurolides A and B, together with five new related lactones with the same unusual skeleton were isolated from the aerial parts of Anthemis arvensis growing in Serbia. The originally proposed structure of antheindurolide B was revised. This (antheindurolide) type of lactones, detected so far only in the genus Anthemis (Anthemis indurata, Anthemis pseudocotula and Anthemis cotula) could be of chemotaxonomic significance.     

Photobacterium malacitanum sp. nov., and Photobacterium andalusiense sp. nov., two new bacteria isolated from diseased farmed fish in Southern Spain

Three strains, H01100409B^T, H01100413B, and H27100402H^T, were isolated from several internal organs of diseased redbanded seabream (Pagrus auriga) reared in Andalusia (Southern Spain). All strains were studied by phenotypic, including chemotaxonomy, and genomic characteristics. Phylogenetic analysis based on concatenated sequences of six housekeeping genes (gyrB, ftsZ, topA, mreB, gapA, and 16S rRNA) supported the inclusion of the strains within the clade Phosphoreum of the genus Photobacterium, and two of the strains (H27100402H^T and H01100409B^T) formed a tight group separated from the closest species P. aquimaris. Genomic analyses, including average nucleotide identity (ANIb and ANIm) and DNA–DNA hybridization (DDH), clearly separated strains H27100402H^T and H01100409B^T from the other species within the clade Phosphoreum with values below the thresholds for species delineation. The chemotaxonomic features (including FAME analysis and MALDI-TOF-MS) of H27100402H^T and H01100409B^T strains confirmed their differentiation from the related taxa. The results demonstrated that strain H01100413B was classified as P. aquimaris and the strains H27100402H^T and H01100409B^T represented a new species each in the genus Photobacterium, for which we propose the names Photobacterium malacitanum sp. nov., type strain H27100402H^T (=CECT 9190^T = LMG 29992^T), and Photobacterium andalusiense sp. nov., type strain H01100409B^T (=CECT 9192^T = LMG 29994^T).     

Structure of histamine releasing guaianolides from Thapsia species

The structures of six hexaoxygenated guaianolides esterified with four non isomeric carboxylic acids have been established by ¹H NMR and ¹³C NMR spectroscopy. The acyl residues have been located by chemical ionisation mass spectrometry. Some of the acyl residues are novel for sesquiterpene lactones. The acyl residues in two additional guaianolides esterified with isomeric acids have been located by partial hydrolysis.     

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.     

Three new melampolide sesquiterpenes,polymatin A,B and C,from Polymnia maculata Cav. var. maculata

Three new melampolide type sesquiterpene lactones were isolated from Polymnia maculata Cav. var. maculata. Their structures were determined by spectroscopic and chemical means. Based on the presently available chemical data, the chemotaxonomic position of Polymnia within the subtribe is discussed.     

Further sesquiterpene lactones from Calea and Viguiera species

The aerial parts of Calea clematidea gave three new germacranolides, those of Viguiera procumbens two orizabin derivatives and those of V. linearis dihydrobudlein A. In addition to these lactones, several known ones were isolated.     

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.     

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 chemical composition of the litter and soil in a community of Artemisia tridentata ssp. vaseyana

The leaves, litter, and soil from within a community of Artemisia tridentata ssp. vaseyana were analyzed for secondary metabolic products. Methacrolein, five monterpenes, three sesquiterpene lactones, six coumarins, and one flavonoid were identified in the leaves; the contents of the litter were nearly identical. Soils collected directly beneath the shrubs contained the three sesquiterpene lactones, two coumarins and an unknown flavonoid. The litter and water extracts of the litter inhibited the germination of sagebrush seeds. Soils charged with monoterpenes from sagebrush leaves also inhibited seed germination. In addition, the monoterpene contents from eight sagebrush taxa collected from Western Montana are reported.     

Two sesquiterpene lactones from Trichogonia gardneri

The structures and stereochemistries of two sesquiterpene lactones from Trichogonia gardneri were established as (6R,7S,8S,9S,IOR)-4E-9,10-dihydroxy-8-tigloxygermacr-4-en-6,12-olide) and (5R*,6R*,7S*,8S*,9R*)-14-acetoxy-3-chloro-9-hydroxy-2-oxo-8-tigloxyguia-1(10),3-dien-6,12-of olide by a combination of NMR spectrometry and X-ray diffraction. The results show that the structures of several sesquiterpene lactones which were isolated previously from related species require revision.     

Rhizobium pisi sv. trifolii K3.22 harboring nod genes of the Rhizobium leguminosarum sv. trifolii cluster

The taxonomic status of the Rhizobium sp. K3.22 clover nodule isolate was studied by multilocus sequence analysis (MLSA) of 16S rRNA and six housekeeping chromosomal genes, as well as by a subsequent phylogenic analysis. The results revealed full congruence with the Rhizobium pisi DSM 30132^T core genes, thus supporting the same taxonomic position for both strains. However, the K3.22 plasmid symbiosis nod genes demonstrated high sequence similarity to Rhizobium leguminosarum sv. trifolii, whereas the R. pisi DSM 30132^Tnod genes were most similar to R. leguminosarum sv. viciae. The strains differed in the host range nodulation specificity, since strain K3.22 effectively nodulated red and white clover but not vetch, in contrast to R. pisi DSM 30132^T, which effectively nodulated vetch but was not able to nodulate clover. Both strains had the ability to form nodules on pea and bean but they differed in bean cultivar specificity. The R. pisi K3.22 and DSM 30132^T strains might provide evidence for the transfer of R. leguminosarum sv. trifolii and sv. viciae symbiotic plasmids occurring in natural soil populations.     

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.