Sacculatane diterpenoids from axenic cultures of the liverwort Fossombronia wondraczekii

Five new sacculatane diterpenoids, 17,18-epoxy-7-sacculaten-12,11-olide, 7,17-sacculatadien-11,12-olide, 11beta,12-epoxy-7,17-sacculatadien-11alpha-ol, 1beta-acetoxy-11beta,12-epoxy-7,17-sacculatadien-11alpha-ol and 1beta,15xi-diacetoxy-11,12-epoxy-8(12),9(11),17-sacculatatriene along with sacculatal and sacculatanolide have been isolated from axenic cultures of the liverwort Fossombronia wondraczekii and their structures assigned on the basis of their spectroscopical properties.     

ent-Verticillane-type diterpenoids from the Japanese liverwort Jackiella javanica

Three ent-verticillane diterpenoids and two ent-sesquiterpenoids were isolated from the Japanese liverwort Jackiella javanica Schiffn. together with five known ent-verticillane and three ent-kaurane diterpenoids, and three sesquiterpenoids. Five ent-verticillane epoxides were synthetically prepared from ent-verticillols action to clarify the absolute configuration of natural ent-9,10-epoxyverticillol. Their structures were established by extensive NMR spectroscopic and X-ray crystallographic analyses.     

Three ent-eudesmenones from the liverwort Plagiochila bifaria

The essential oil of the liverwort Plagiochila bifaria was analysed by GC and GC-MS. Three eudesmane type sesquiterpenes, ent-eudesm-4-en-6-one, ent-eudesm-4(15)-en-6-one, ent-7-hydroxyeudesm-4-en-6-one were isolated and identified as new natural products. Structure elucidation and the determination of absolute configurations are described.     

ent-Isopimarane-type diterpenoids from the New Zealand liverwort Trichocolea mollissima

Two ent-isopimarane-type diterpenoids were isolated from the New Zealand liverwort Trichocolea mollissima (Hook. f. and Tayl.) Gott., together with a known 1alpha-hydroxy-ent-sandaracopimara-8(14),15-diene. Their absolute structures have been established by modified Mosher's method, X-ray crystallography and by analyses of their CD spectra.     

Lignan derivatives from the liverwort Bazzania trilobata

Eight lignan derivatives trilobatin D-K, as well as jamesopyrone were isolated from the liverwort Bazzania trilobata. Their structures have been elucidated based on extensive NMR spectral evidence.     

Bazzanins L-R,chlorinated macrocyclic bisbibenzyls from the liverwort Lepidozia incurvata

Seven new chlorinated bisbibenzyls (bazzanins L-R), of the isoplagiochin C type, as well as isoplagiochin C have been isolated from the liverwort Lepidozia incurvata. The structures have been elucidated based on extensive NMR spectral evidence and by mass spectrometry.     

Secondary metabolites from the liverwort Tylimanthus renifolius

Two new herbertane sesquiterpenoids, (-)-herbertene-1,12-diol and (-)-gamma-herbertenol, a new aromadendrane, 9-acetoxy-10-hydroxyaromadendrane, a new rosane diterpenoid, 5,15-rosadiene-3,11-dione and a new phytane, 2Z-phytene-1,15,20-triol, along with the known (-)-alpha-herbertenol have been isolated from the liverwort Tylimanthus renifolius. Several flavones and flavanones with an unsubstituted ring B were also identified. This is the first report of this class of flavonoids from the Hepaticae. All structures were elucidated by NMR spectroscopy.     

Bioactivity guided isolation of antifungal compounds from the liverwort Bazzania trilobata (L.) S.F. Gray

A dichloromethane and a methanol extract of the liverwort Bazzania trilobata showed antifungal activity against the phytopathogenic fungi Botrytis cinerea, Cladosporium cucumerinum, Phythophthora infestans, Pyricularia oryzae and Septoria tritici. Bioautography on thin-layer chromatograms was used to isolate six antifungal sesquiterpenes: 5- and 7-hydroxycalamenene, drimenol, drimenal, viridiflorol, gymnomitrol and three bisbibenzyls: 6 ',8'-dichloroisoplagiochin C, isoplagiochin D and 6'-chloroisoplagiochin D. Furthermore we report the isolation of gymnomitr-8(12)-en-4-one and the new coumarin 7,8-dihydroxycoumarin-7-O-beta-D-glucuronide. Their structures have been elucidated based on extensive NMR spectral evidence.     

Terpenoids from Microliabum polymnioides

The phytochemical study of M. polymnioides led to the isolation of two sesquiterpene lactones namely: 11alphaH-dihydrozaluzanin E and 1beta-hydroxy-4-oxo-11betaH-4-noreudesman-6,12-olide. Their structures were determined by spectroscopic methods. The relative stereochemistry was established by a combination of coupling constant analysis, NOESY correlations and molecular modeling. Three related known sesquiterpene lactones were also identified, and these data were used for chemotaxonomical purposes.     

Eremophilanolides and other constituents from the Argentine liverwort Frullania brasiliensis.

Two eremophilanolides, 5-epidilatanolides A and B, as well as a new natural bibenzyl were isolated from an Argentine collection of the liverwort Frullania brasiliensis, along with the known eudesmane-type sesquiterpene lactones nepalensolide A, nepalensolide B, (+)-frullanolide, and (+)-dihydrofrullanolide, the hopanoid zeorin, the four sterols stigmasta-4,22-dien-3,6-dione, stigmasta-4,22-dien-3-one, stigmasterol, and sitosterol, and a trace amount of atraric acid. The structure and stereochemistry of the eremophilanolides and the bibenzyl were established by a combination of extensive NMR spectroscopy experiments and X-ray crystallographic analysis. Absolute configurations of the new compounds were derived on the basis of CD spectra.     

Terpenoids from Guarea guidonia

The volatile oil and the methanol extract from the leaves of Guarea guidonia, Meliaceae, were individually submitted to chromatographic separation. A sesquiterpene (2S*)-eudesma-5,7-dien-2-ol, together with six known ones, were isolated from the volatile oil. The methanolic extract afforded two known and two new triterpenes (23S*)-cycloart-24-ene-3 beta,23-diol and (23R*)-cycloart-24-ene-3 beta,23-diol, besides three known sesquiterpenes, one known diterpene and two steroids. Their structures were established on the basis of spectrocopic data, mainly by 1H and 13C NMR spectroscopic analyses.     

Terpenoids and phenol derivatives from Malva silvestris

A sesquiterpene and a tetrahydroxylated acyclic diterpene as well as two known monoterpenes, 6 C(13)nor-terpenes and 11 aromatic compounds were isolated from the water extract of Malva silvestris. The structures of the compounds were determined by spectroscopic NMR and MS analysis. Effects of these compounds on germination and growth of dicotyledon Lactuca sativa L. (lettuce) were studied in the 10(-4)-10(-7)M concentration range.     

Sesquiterpene constituents from the liverwort Bazzania japonica

The hydrodistillation products of the liverwort Bazzania japonica were separated by preparative gas chromatography (GC) and investigated by spectroscopic methods. Seven unknown compounds were isolated and identified by GC-MS and NMR. Four of them, the norsesquiterpene hydrocarbons 4-epi-11-nor-aristola-1(10),11-diene (1), 4-epi-11-nor-aristola-1,9,11-triene (2), 4-epi-11-nor-aristola-9,11-diene (3), and one oxygenated sesquiterpene, (-)-aristol-1(10)-en-12-ol (5) are new natural compounds, and one, (+)-himachala-2,4-diene (7), has for the first time been isolated from liverworts. The absolute configurations of 5 and 7 were derived by chemical correlation reactions and/or enantioselective GC using cyclodextrin phases. 1, 2 and 3 have identical absolute configuration.     

Secondary metabolites from the liverwort Jamesoniella colorata

Six new labdane type diterpenoids, three seco-clerodane diterpenoids, jamesoniellide I, along with the two new jamesoniellides K and L, the sesquiterpene waitziacuminone and a new chlorinated bisbibenzyl, 6,6',10,10',12,12'-hexachloroisoperrottetin A, have been isolated from the liverwort Jamesoniella colorata. Their structures were elucidated by NMR spectroscopy. The absolute configuration of 3-oxo-labda-8(17),13(16),14-triene (1) was established by CD spectroscopy.     

Terpenoids from Dysoxylum densiflorum

Three degraded limonoids, dysodensiols A-C (1-3), and three sesquiterpenoids, dysodensiols D-F (4-6), along with 17 known compounds, were isolated from the twigs and leaves of Dysoxylum densiflorum. The structures of compounds 1-6 were established on the basis of extensive spectroscopic analysis.     

Evolution of Cryptosporidium in vitro culture

This overview discusses findings from culturing Cryptosporidium spp. in cell and axenic cultures as well as factors limiting the development of this parasite in cultivation systems during recent years. A systematic review is undertaken of findings regarding the life cycle of the parasite, taking into account physiological, biochemical and genetic aspects, in the hope that this attempt will facilitate future approaches to research and developments in the understanding of Cryptosporidium biology.     

Terpenoids and bibenzyls of 25 liverwort Frullania species

Twenty-five Frullania species (liverworts) were chemically investigated. Fourteen species produce allergy-inducing sesquiterpene lactones. Eighteen species contain bibenzyls. The sesquiterpene lactones and bibenzyls are obtained as the major components and they are valuable chemosystematic markers of Frullania species. On the basis of their chemical constituents, Frullania species can be divided into five chemotypes: sesquiterpene lactone-bibenzyl type; sesquiterpene lactone type; bibenzyl type; monoterpene type and cyclocolorenone type.     

Terpenoids from Juniperus polycarpus var. seravschanica

Two eudesmanes, two abietanes, two podocarpanes and other nine known compounds were isolated from the dried fruits of Juniperus polycarpus var. seravschanica. Their structures were established on the basis of analysis of spectroscopic evidence. Some of the isolated terpenoids showed antimalarial activity.     

Terpenoids from Tripterygium doianum (Celastraceae)

The extract of Tripterygium doianum (Celastraceae) afforded three triterpenoids [3beta-acetoxy-11-ursen-13alpha,30-olide, 25-chloro-24-hydroxytirucall-7-en-3-one and tirucall-7-en-3,24-dione], two sesquiterpenoids [5alpha-acetoxy-1beta,8alpha-bis-cinnamoyl-4alpha-hydroxydihydroagarofuran and 5alpha-acetoxy-1beta-benzoyl-8alpha-cinnamoyl-4alpha-hydroxydihydroagarofuran] and nine known triterpenoids. Their structures were established based on spectroscopic studies.