Sterols and Fatty Acids of the Harmful Dinoflagellate Cochlodinium polykrikoides

Sterol and fatty acid compositions were determined for Cochlodinium polykrikoides, a toxic, bloom‐forming dinoflagellate of global significance. The major sterols were dinosterol (40% of total sterols), dihydrodinosterol (32%), and the rare 4α‐methyl Δ⁸⁽¹⁴⁾ sterol, amphisterol (23%). A minor sterol, 4α‐methylergost‐24(28)‐enol was also detected (5.0%). The fatty acids had a high proportion of PUFAs (47%), consisting mainly of EPA (20%) and the relatively uncommon octadecapentaenoic acid (18 : 5, 22%). While unlikely to be responsible for toxicity to fish, these lipids may contribute to the deleterious effects of this alga to invertebrates.     

茅台上游河谷地区苔藓植物生态学研究

对贵州茅台镇茅台上游河谷地区的苔藓植物生态学进行了研究。结果表明,该地区有苔藓植物30科53属116种;生态类型有石生、土生、沙生、树附生、腐木生和水生等6种;PCA排序分析表明,在大气候相同的环境下,苔藓植物生态分布格局差异大,主要受微环境的影响。淡色同叶藓、拟阔叶小石藓、毛口藓、齿边缩叶藓、褶叶青藓和拟脆枝曲柄藓为该地区的优势苔藓植物,其生物量为32.80~225.00 g m-2,饱和吸水量为23519.90~269999.96 g m-2。这说明,苔藓植物在该地区的生态修复过程中,以其特有的生态功能在水土保持和涵养水源、物质循环、土壤性质改善和更新等方面起到十分重要的作用。     

"Dinoflagellate Sterols" in marine diatoms

Sterol compositions for three diatom species, recently shown to contain sterols with side chains typically found in dinoflagellates, were determined by HPLC and ¹H NMR spectroscopic analyses. The centric diatom Triceratium dubium (= Biddulphia sp., CCMP 147) contained the highest percentage of 23-methylated sterols (37.2% (24R)-23-methylergosta-5,22-dienol), whereas the pennate diatom Delphineis sp. (CCMP 1095) contained the cyclopropyl sterol gorgosterol, as well as the 27-norsterol occelasterol. The sterol composition of Ditylum brightwellii (CCMP 358) was the most complex, containing Δ⁰- and Δ⁷-sterols, in addition to the predominant Δ⁵-sterols. A pair of previously unknown sterols, stigmasta-5,24,28-trienol and stigmasta-24,28-dienol, were detected in D. brightwellii and their structures were determined by NMR spectroscopic analysis and by synthesis of the former sterol from saringosterol. Also detected in D. brightwellii was the previously unknown 23-methylcholesta-7,22-dienol.     

The fatty acid and sterol composition of two marine dinoflagellates

The fatty acid, sterol and chlorophyll pigment compositions of the marine dinoflagellates Gymnodinium wilczeki and Prorocentrum cordatum are reported. The fatty acids of both algae show a typical dinoflagellate distribution pattern with a predominance of C₁₈, C₂₀ and C₂₂ unsaturated components. The acid 18:5ω3 is present at high concentration in these two dinoflagellates. G. wilczeki contains a high proportion (93.4%) of 4-methyl-5α-stanols including 4,23,24-trimethyl-5α-cholest-22E-en-3β-ol (dinosterol), dinostanol and 4,23,24-trimethyl-5α-cholest-7-en-3β-ol reported for the first time in dinoflagellates. The role of this sterol in the biosynthesis of 5α-stanols in dinoflagellates is discussed. P. cordatum contains high concentrations of a number of δ ²⁴⁽²⁸⁾-sterols with dinosterol, 24-methylcholesta-5,24(28)-dien-3β-ol, 23,24-dimethylcholesta-5,22E-dien-3β-ol, 4,24-dimethyl-5α-cholest-24(28)-en-3β-ol and a sterol identified as either 4,23,24-trimethyl- or 4-methyl-24-ethyl-5α-cholest-24(28)-en-3β-ol present as the five major components. The role of marine dinoflagellates in the input of both 4-methyl- and 4-desmethyl-5α-stanols to marine sediments is discussed.     

Herbaria century record of increasing eutrophication in Spanish terrestrial ecosystems

Additional biological evidence is presented for the alteration of biogeochemical cycles by human activities. The leaf δ¹⁵N and the concentrations of nutrients in herbarium specimens of 24 species of vascular plants and 3 species of bryophytes collected in northern and eastern regions of Spain have substantially changed throughout the XX century. In the second half of the century, when anthropogenic nitrogen fixation and mobilization started to increase rapidly, leaf δ¹⁵N values started to decrease strongly, indicating that additional anthropogenic nitrogen is being retained in Spanish terrestrial ecosystems. The concentration of nutrients in vascular plants did not present any clear pattern, but there were increasing concentrations of N and other nutrients (P, K, and S) in the last decades in bryophytes, which are usually better biomonitors of airborne chemicals than vascular plants. Important consequences for ecosystem structure and functioning such as enhancement of the carbon sink or changes in community biodiversity and species distribution may be expected from this increase in eutrophication.     

Structural Characterization and Chemical Classification of Some Bryophytes Found in Latvia

Bryophytes are the second largest taxonomic group in the plant kingdom; yet, studies conducted to better understand their chemical composition are rare. The aim of this study was to characterize the chemical composition of bryophytes common in Northern Europe by using elemental, spectral, and non‐destructive analytical methods, such as Fourier transform IR spectrometry (FT‐IR), solid‐phase ¹³C‐NMR spectrometry, and pyrolysis‐gas chromatography/mass spectrometry (Py‐GC/MS), for the purpose of investigating their chemotaxonomic relationships on the basis of chemical‐composition data. The results of all these analyses showed that bryophytes consist mainly of carbohydrates. Judging by FT‐IR spectra, the OH groups in combination of C? O groups were the most abundant groups. The ¹³C‐NMR spectra provided information on the presence of such compounds as phenolics and lipids. It was found that the amount of phenolic compounds in bryophytes is relatively small. This finding definitely confirmed the absence of lignin in the studied bryophytes. Cluster analysis was used to better understand differences in the chemical composition of bryophyte samples and to evaluate possible usage of these methods in the chemotaxonomy of bryophytes.     

Old trees contribute bio-available nitrogen through canopy bryophytes

Symbiotic cyanobacteria??bryophyte associations on the forest floor are shown to contribute significantly to stand-level nitrogen budgets through the process of biological nitrogen fixation (BNF), but few studies have considered the role of canopy bryophytes. Given the high biomass of epiphytic bryophytes in many tree species of the North American temperate rain forest, we suggest that canopy bryophytes may contribute substantially to stand-level N dynamics. We confirm the presence of cyanobacteria and measure rates of BNF at three heights (0, 15 and 30 m) in Sitka spruce trees across three watershed estuaries of Clayoquot Sound, British Columbia, Canada. This study is the first to report BNF by cyanobacteria associated with epiphytic and forest floor bryophytes in the coastal temperate rain forest of North America. Cyanobacteria density was significantly greater in epiphytic bryophytes compared to mosses on the forest floor, and rates of BNF were highest at 30 m in the canopy. The majority of total stand-level BNF (0.76 kg N · ha^-1 · yr^-1) occurs in the canopy, rather than on the forest floor (0.26 kg N · ha^-1 · yr^-1). We suggest that BNF by cyanobacterial-bryophyte associations in the canopy of coastal temperate rain forests is a unique source of ecosystem N, which is dependent on large, old trees with high epiphytic bryophyte biomass.     

Main sterols from the ophiuroids Ophiocoma echinata, Ophiocoma wendtii, Ophioplocus januarii and Ophionotus victoriae

Sterol compositions of the cold water ophiuroids Ophioplocus januarii and Ophionotus victoriae and of the tropical ophiuroids Ophiocoma echinata and Ophiocoma wendtii are reported. The four sterol mixtures contain Δ⁵ mono- and di-unsaturated common 3β-hydroxy-sterols. Ophioplocus januarii and O. victoriae contain 24-methylcholesta-5,24(28)-dien-3β-ol and 24ζ-ethylcholesta-5,24(28)-dien-3β-ol in higher abundance than in O. echinata. These sterols were not found in O. wendtii. An interesting finding is the presence of Δ^5,24(28)-24-n-propylidenecholesterol in 7.6% in Ophionotus victoriae.     

Integrating bryophytes into a forest management plan: lessons from grid-mapping in the forest of Soignes (Belgium)

258 bryophyte species were recorded in the 4 380 ha of the forest of Soignes (Belgium). The specific richness is artificially increased by many bryophytes not characteristic of forests such as epilithic species and weeds. In addition, certain species characteristic of ancient woodlands, like Anomodon viticulosus, Brachythecium plumosum, Homalia trichomanoides, Homalothecium sericeum, Rhizomnium punctatum, Taxiphyllum wissgrillii and Thamnobryum alopecurum were found on the concrete of the drainage network. Thus, the richness of the forest of Soignes is partly due to the ability of the bryophytes to colonize habitats of substitution. This ability suggests that the use of bryophytes as indicators of ancient woodlands must be properly tested. Two species, Ephemerum stellatum and Orthotrichum consimile, belong to the European Red List of Bryophytes, while 20 other species are considered as rare or threatened in Belgium. In addition, the forest of Soignes represents a remarkable disjunct area of distribution in Belgium for a number of other species. The distribution of species richness is patchy, ranging from 37 species·km⁻² to 122 species·km^−2, with an average of 70.5 species·km⁻². The effects of current management practices on the bryoflora are documented, and suggestions for integrating bryophyte conservation with logging and recreation are made.     

Composition sterolique et morphogeneses reproductrices chez Gnomonia leptostyla

Sterol components of Gnomonia leptostyla mycelia have been investigated from in vitro cultures in which sexual and asexual morphogenesis are induced by temperature and light conditions. The nature and content of free sterols and sterol esters were determined by MIKE spectrometry. Relations between sterol composition (total sterols; Δ^5,7 and Δ⁵ sterols) and reproductive morphogenesis are discussed, particularly with respect to the degree of sexuality induced.     

Metabolism of (24R and 24S)-27-nor-24-methyl-3α,7α-dihydroxy-5β-cholestan-26-oic acids and 27-nor-3α,7α-dihydroxy-5β-cholestan-26-oic acid in guinea pigs

[7β-³H]-(24R and 24S)-27-nor-24-methyl-3α,7α-dihydroxy-5β-cholestan-26-oic acids and [7β-³H]-27-nor-3α,7α-dihydroxy-5β-cholestan-26-oic acid (C₂₇ and C₂₆ bile acids having the same nuclear configuration as cheno-deoxycholic acid and its precursor, 3α,7α-dihydroxy-5β-cholestan-26-oic-acid) were synthesized and administered intraperitoneally to bile fistula guinea pigs. The biliary bile acids formed were hydrolyzed and analyzed by thin layer chromatography, and the metabolites were identified by the inverse isotope dilution method. The results showed that both (24R and 24S)-27-nor-24-methyl-3α,7α-dihydroxy-5β-cholestan-26-oic acids were not metabolized by the liver and were excreted unchanged as their taurine and glycine conjugates whereas 27-nor-3α,7α-dihydroxy-5β-cholestan-26-oic acid was converted to chenodeoxycholic acid.     

Synthesis and evaluation of in vitro anticancer activity of some novel isopentenyladenosine derivatives

The present study describes the synthesis, the characterization and the evaluation of some derivatives of N⁶-isopentenyladenosine on T24 human bladder carcinoma cells. In particular we have modified the hydroxyl groups in the ribose moiety, the position of the isopentenyl chain in the purine ring and the base moiety. The structures of the compounds were confirmed by standard studies of NMR, MS and elemental analysis. We here show that only two derivatives, 1-(3-methyl-2-butenylamino)-9-(3′-deoxy-β-d-ribofuranosyl)-purine hydrobromide and 2-amino-6-(3-methyl-2- butenylamino)-9-(β-d-ribofuranosyl)-purine, inhibit the growth of T24 cells, although to a lower extent than N⁶-isopentenyladenosine. We conclude that the integrity of ribosidic and purine moiety and the N⁶ position of the chain are essential for maintaining the antiproliferative activity.     

Sterol composition of itraconazole-resistant and itraconazole-susceptible isolates of Aspergillus fumigatus

Sterol composition of four clinical isolates of Aspergillus fumigatus resistant to itraconazole was determined by gas chromatography--mass spectrometry and compared with that of four susceptible strains. For all strains, the major sterol was ergosterol. Sterol compositions were qualitatively and quantitatively similar for the resistant and susceptible strains. These results suggest that itraconazole resistance is not related, for the strains studied, to alterations in the ergosterol synthesis pathway.     

Sterols with unusual nuclear unsaturation from three cultured marine dinoflagellates

Several new 4α-methyl sterols with unusual unsaturation in the Δ⁸⁽¹⁴⁾-or Δ¹⁴-positions, 4α,24S-dimethyl-5α-cholest-8 (14)-en-3β-ol, 4α-methyl-24ξ-ethyl-5α-cholest-8(14)-en-3β-ol, 4α-methyl-24(Z)-ethylidene-5α-cholest-8(14)- en-3β-ol, 4α,23 (or 22),24ξ-trimethyl-5α-cholesta-8(14),22-dien-3β-ol, 4α,24S(or 23ξ)-dimethyl-5α-cholest-14-en-3β-ol and 14-dehydrodinosterol, have been isolated from extracts of the cultured marine dinoflagellates Amphidinium carterae, A. corpulentum and Glenodinium sp. 4α-Methyl-24ξ-ethyl-5α-cholestan-3β-ol was isolated from the steryl ester fraction of Glenodinium sp. The structures of these new sterols are based upon extensive 360 MHz ¹H NMR and MS analyses.     

Community Structure of In-Stream Bryophytes in English and Welsh Rivers

Information on the distribution of bryophytes in mainland British rivers was collected as part of the Joint Nature Conservancy Council (JNCC) survey of in-stream macrophyte distribution between 1978 and 1997. A sub-set of sites (1604) containing the 50 most common bryophytes was analysed. The commonest of these 50 species were Fontinalis antipyretica and Rhynchostegium riparioides. The majority of species encountered are not considered to be truly aquatic. Detrended Correspondence Analysis of community structure revealed a continuum of variation in assemblages across sites rather than distinct groupings of bryophytes. Canonical Correspondence Analysis was used to analyse a sub-set of sites (625) for which water chemistry were available to test the influence of environmental variables on the distribution of bryophytes. The analysis suggested the strongest environmental gradient was the transition from lowland systems on chalk geology to steeply sloping, high altitude systems with resistant geology. Mapping CCA axis 1 scores on to a map of England and Wales suggested a geographic trend in bryophyte species distribution with community structure undergoing a transition from the upland regions and the western seaboard to the south east of England. Stepwise regression analysis confirmed the importance of the upland lowland trend, showing that substrate size, altitude of source, distance to source and altitude were important predictors of species richness (p < 0.0001, adjusted R² = 0.30).     

Effect of ay-9944 on sterol biosynthesis in Chlorella sorokiniana

When Chlorella sorokiniana was grown in the presence of 4 ppm AY-9944 total sterol production was unaltered in comparison to control cultures. However, inhibition of sterol biosynthesis was shown by the accumulation of a number of sterols which were considered to be intermediates in sterol biosynthesis. The sterols which were found in treated cultures were identified as cyclolaudenol, 4α,14α-dimethyl-9β,19-cyclo-5α-ergost-25-en-3β-ol, 4α,14α-dimethyl -5α-ergosta-8,25-dien-3β-ol, 14α-methyl-9β,19-cyclo-5α-ergost-25-en-3β-ol, 24-methylpollinastanol, 14α-methyl-5α-ergost-8-en-3β-ol, 5α-ergost -8(14)-enol, 5α-ergost-8-enol, 5α-ergosta-8(14),22-dienol, 5α-ergosta-8,22-dienol, 5α-ergosta-8,14-dienol, and 5α-ergosta-7,22-dienol, in addition to the normally occurring sterols which are ergosterol, 5α-ergost-7-enol, and ergosta-5,7-dienol.The occurrence of these sterols in the treated culture indicates that AY-9944 is an effective inhibitor of the Δ⁸ → Δ⁷ isomerase and Δ¹⁴-reductase, and also inhibits introduction of the Δ²²-double bond. The occurrence of 14α-dimethyl-5α-ergosta-8,25-dien-3β-ol and 14α-methyl-9β,19-cyclo-5α-ergost -25-en-3β-ol is reported for the first time in living organisms. The presence of 25-methylene sterols suggests that they, and not 24-methylene derivatives, are intermediates in the biosynthesis of sterols in C. sorokiniana.     

The effect of chemical structure on the antagonism by cyclopropenes of ethylene responses in banana

The compounds, cyclopropene, 1-methylcyclopropene, 3-methylcyclopropene, 1,3-dimethylcyclopropene, 3,3-dimethylcyclopropene, 1,3,3-trimethylcyclopropene, 3-methyl-3-vinylcyclopropene, and 3-methyl-3-ethynylcyclopropene, and 1,2-dimethylcyclopropene were tested as antagonists to the ethylene receptor in bananas. All of the compounds inactivated the receptor and the bananas did not respond to ethylene even at 1000 nL L^–1. Large differences were found in the concentration required (0.7–20,000 nL L^–1 for 24h) to inactivate the receptor and in the duration of inactivation (3–12 days at 24C depending on the compound). After this time the bananas responded to ethylene and appeared to ripen normally.     

Synthesis of New 15-Ketosterol Analogues from Ergosterol

Ergosteryl acetate was converted through three stages into 3-acetoxy-24-methyl-5-cholesta-8(14),22-diene-15-one in 32% overall yield. The product was transformed to 3-hydroxy-24-methyl-5-cholesta-8(14),22-diene-15-one, 3-hydroxy-24-methyl-5-cholesta-8(14),22-diene-15-one, and 24-methyl-5-cholesta-8(14),22-diene-3,15-dione. The compounds were characterized by ¹H and ¹³C NMR spectra.     

Accumulation of Δ8,14-sterols in suspension cultures of bramble cells cultured with an azasterol antimycotic agent (A25822B)

Bramble suspension cultures normally contain Δ⁵-sterols (sitosterol, campesterol and isofucosterol). When the cells were grown in a medium supplemented with 15-aza-24-methylene-d-homocholesta-8,14-dien- 3β-ol, Δ⁵-sterols disappeared almost completely whereas Δ^8,14-sterols accumulated strongly. Five Δ^8,14-sterols, including two new compounds, (24R)-24-ethyl-5α-cholesta-8,14-dien-3β-ol and 4α-methyl-5α-stigmasta-8,14, Z-24(28)-trien-3β-ol, were identified. The 15-azasterol probably inhibited the reduction of the Δ¹⁴-bond. Cell lines growing permanently in an azasterol-supplemented medium were obtained.     

喀斯特石漠化区典型生境下石生苔藓的固土持水作用

为探究喀斯特石漠化区典型生境下石生苔藓植物的固土持水能力及影响因素,在其石生苔藓分布和形态特征基础上,深入探讨了不同生境下石生苔藓的固土持水效应。结果表明：（1）生境对石生苔藓植物的固土持水能力影响显著。草地中的宽叶真藓（Bryum funkii）固土量最高,为8.85×10³ kg/hm²,裸地中的美灰藓（Eurohypnum leptothallum）持水量最高,其最高持水量是自身干重的14倍。石生苔藓植物在裸地和草地中表现出较高的固土率,而在乔木林与草地下具有较好的持水率。（2）苔藓类型对固土持水能力存在显著性的影响。4种石生苔藓植物的固土率高低为宽叶真藓>尖叶对齿藓原变种（Didymodon constrictus var.constrictus）>卷叶湿地藓（Hyophila involuta）>美灰藓,且差异显著;4种苔藓植物的持水率强弱为美灰藓>宽叶真藓>卷叶湿地藓>尖叶对齿藓原变种。（3）石生苔藓植物的固土持水能力受自身功能性状和立地环境的综合影响,苔藓植物的固土率与干重存在显著的正相关关系,其持水量与干重和生物量间具有显著的正相关关系。综上,从固土持水和生态修复的角度出发,应加强裸地和草地两种生境的石漠化治理力度;可考虑将宽叶真藓和美灰藓作为喀斯特岩面生态恢复的先锋苔藓,其能有效解决喀斯特区石漠化大面积基岩裸露问题,提高喀斯特区水土保持效益。