Synthesis of 3′,4′-difluoro-3′-deoxyribonucleosides and its evaluation of the biological activities: Discovery of a novel type of anti-HCV agent 3′,4′-difluorocordycepin

Upon reacting 3′,4′-unsaturated cytosine (8 and 9) and adenine nucleosides (13 and 14) with XeF₂/BF₃·OEt₂, the respective novel 3′,4′-difluoro-3′-deoxyribofuranosyl nucleosides (10–12 and 15–18) could be obtained. Formation of anti-adducts (11, 16 and 18) revealed that the fluorination involved oxonium ions as incipient intermediates. TBDMS-protected 3′,4′-unsaturated adenosine provided the β-face adducts as sole stereoisomers whereas α-face-selectivity was observed with the TBDPS-protected adenosine 14. The evaluation of the novel 3′-deoxy-3′,4′-difluororibofuranosylcytosine-(19–21) and adenine nucleosides (22–25) against antitumor and antiviral activities revealed that 3′,4′-difluorocordycepin (24) was found to possess anti-HCV activity. The SI of 24 was comparable to that of the anti-HCV drug ribavirin. However, sofosbuvir, FDA-approved novel anti-HCV drug, showed better SI value. Our finding revealed that the introduction of the fluoro-substituent into the 4′-position of cordycepin derivatives decreased the cytotoxicity to the host cell with retention of the antiviral activity.     

Why did heterospory evolve?

The primitive land plant life cycle featured the production of spores of unimodal size, a condition called homospory. The evolution of bimodal size distributions with small male spores and large female spores, known as heterospory, was an innovation that occurred repeatedly in the history of land plants. The importance of desiccation‐resistant spores for colonization of the land is well known, but the adaptive value of heterospory has never been well established. It was an addition to a sexual life cycle that already involved male and female gametes. Its role as a precursor to the evolution of seeds has received much attention, but this is an evolutionary consequence of heterospory that cannot explain the transition from homospory to heterospory (and the lack of evolutionary reversal from heterospory to homospory). Enforced outcrossing of gametophytes has often been mentioned in connection to heterospory, but we review the shortcomings of this argument as an explanation of the selective advantage of heterospory. Few alternative arguments concerning the selective forces favouring heterospory have been proposed, a paucity of attention that is surprising given the importance of this innovation in land plant evolution. In this review we highlight two ideas that may lead us to a better understanding of why heterospory evolved. First, models of optimal resource allocation – an approach that has been used for decades in evolutionary ecology to help understand parental investment and other life‐history patterns – suggest that an evolutionary increase in spore size could reach a threshold at which small spores yielding small, sperm‐producing gametophytes would return greater fitness per unit of resource investment than would large spores and bisexual gametophytes. With the advent of such microspores, megaspores would evolve under frequency‐dependent selection. This argument can account for the appearance of heterospory in the Devonian, when increasingly tall and complex vegetative communities presented competitive conditions that made large spore size advantageous. Second, heterospory is analogous in many ways to anisogamy. Indeed, heterospory is a kind of re‐invention of anisogamy within the context of a sporophyte‐dominant land plant life cycle. The evolution of anisogamy has been the subject of important theoretical and empirical investigation. Recent work in this area suggests that mate‐encounter dynamics set up selective forces that can drive the evolution of anisogamy. We suggest that similar dispersal and mating dynamics could have underlain spore size differentiation. The two approaches offer predictions that are consistent with currently available data but could be tested far more thoroughly. We hope to re‐establish attention on this neglected aspect of plant evolutionary biology and suggest some paths for empirical investigation.     

Determination of the optimal parasitoid‐to‐host ratio for efficient mass‐rearing of the parasitoid,Sclerodermus pupariae (Hymenoptera: Bethylidae)

Sclerodermus pupariae Yang et Yao (Hymenoptera: Bethylidae) is used as a potential biocontrol agent for several buprestid and cerambycid larvae. This study aimed to enhance the efficiency of mass‐rearing of this parasitoid by investigating the fitness gain of this bethylid wasp, including the proportion of successful parasitism and development, brood size, sex ratio, proportion of winged female offspring, body size and longevity of female offspring, under eight different maternal parasitoid density treatments using Thyestilla gebleri Faldermann as host in the laboratory. The results indicated that the foundress densities did not affect the parasitism or emergence rate of this parasitoid. Brood size of the parasitoids increased significantly when the number of maternal wasps ranged from one to four. However, further increases in foundress number did not affect the parasitoid brood size. The sex ratios of S. pupariae were always female‐biased. The proportions of male in the progeny colonies were <10% throughout all experimental treatments. The percentage of winged female progeny was not significantly influenced by the density of adult maternal parasitoids. Body sizes of parasitoids significantly declined with increasing maternal parasitoid densities. Although the parasitoid body size reduced when maternal wasp number was higher, it could be compromised by the relatively higher number of female offspring produced. Further, more than 70% of the parasitoids remained alive when they were stored at 12°C for four months throughout the experiments. These findings suggest that exposure of four female wasps to a single host larva would result in the highest fitness of S. pupariae. Our findings might provide a new approach to enhance the efficiency of mass‐rearing of this bethylid wasp.     

Effect of light on abscisic acid content in photosensitive Scots pine (Pinus sylvestris L.) seed

Dormancy-breaking treatment of the photosensitive Scots pine (Pinus sylvestris L.) seed by white light incubation or a 15-min exposure to red light decreased the abscisic acid content prior to radicle protrusion. Incubation in the dark or exposure to red light followed by a 5-min far-red light irradiation did not cause as great a decrease in abscisic acid content nor was the dormancy relieved. The ability of the far-red light to keep the ABA level high and to prevent germination gradually disappeared as the length of the dark period between the red and far-red treatments was increased to 24 h. ABA was quantified on a gas chromatograph with an electron capture detector.     

中药联合微生态制剂防治呼吸、消化系统病毒病

本文阐述了中药防治病毒病的历史及其应用概况,中药联合微生态制剂防治呼吸、消化系统病毒病的理论依据、临床应用和发展前景。     

Hyperthermic treatment of chromomycosis with disposable chemical pocket warmers

A case of chromomycosis in which hyperthermia proved effective is reported. The patient was a 56-year-old male bean curd maker who, without any previous history of minor trauma, developed on the extensor side of the left upper arm an eczematous lesion that underwent gradual radial expansion. The lesion showed a well-defined, 7×10 cm infiltrated erythematous plaque with the central area healed and, at the upper and lower borders, adherent scales and crusts on the surface. Histological examination revealed granulomatous changes in the dermis, as well as sclerotic cells within giant cells and microabscesses. On culturing,Fonsecaea pedrosoi was isolated. The patient was treated with disposable chemical pocket warmers, which were secured over the lesion with a rather tight elastic bandage, so that they kept the affected area warm for 24 hours a day. After a month of such hyperthermic treatment, the erythema and infiltration had decreased considerably, and microscopic examination and culture of the crusts both yielded negative results. Examination of biopsy specimens of the lesion after the third month showed that it had cicatrized. The treatment was stopped after 4 months, and no relapse occurred. We also summarize the published results of local hyperthermic treatment of chromomycosis in Japan.     

Deposition and longevity of oviposition-deterring pheromone in the cabbage seed weevil

Abstract The cabbage seed weevil ( Ceutorhynchus assimilis Payk.) lays eggs singly into pods of oilseed rape ( Brassica napus L.) through punctures bored with the mouthparts, preferring pods not recently used for oviposition. A simple new choice test has been used to test individual components of egg-laying behaviour for their effect on oviposition site selection. It is confirmed that an oviposition-deterring pheromone (ODP) is deposited during abdomen brushing of the pod which follows egg-laying. Neither pin punctures, weevil feeding punctures, oviposition punctures nor eggs had any deterrent effect. Pods walked on by female weevils were not avoided by those laying eggs. Observations suggest that the ODP is sensed by contact chemoreceptors on the antennae. The deterrent effect lasted only 1–2 h. The implications of these findings on the adaptive significance of the pheromone and its possible use in pest control are discussed.     

Synthesis of Novel 4′-Trifluoromethyl-5′-Norcarbocyclic C-Nucleoside Phosphonic Acids as Potent Anti-Leukemic Agents

The syntheses of novel C-nucleoside phosphonic acids as potential antiviral agents are described. The sugar moiety that served as the nucleoside skeleton was produced starting from commercially available 1,3-dihydroxy cyclopentane. The key C-C bond formation from sugar to base precursor was performed using the Knoevenagel-type condensation. The synthesized compounds exhibited anti-HIV activity and cytotoxicity. Also, the synthesized compounds were screened in vitro for tumor growth inhibitory activity against mouse leukemia cell lines (L-1210, P-815).     

The endotegmen tuberculae: an account of little-known structures from the seed coat of the Hydrocharitoideae (Hydrocharitaceae) and Najas (Najadaceae)

SHAFFER-FEHRE, M., 1991. The endotegmen tuberculae: an account of little-known structures from the seed coat of the Hydrocharitoideae (Hydrocharitaceae) and of Najas (Najadaceae). The sub-cellular protuberances from the inner tegmen layer have been given various names in earlier literature. Here named 'endotegmen tuberculae', they vary in shape, size and density of distribution in the endotegmen of different taxa. These characteristics make them useful for taxonomic research at both genus and species level. Their shape is a major consideration in transferring Hydrocharis dubia to the genus Limnobium. A further structure, 'exotegmen tuberculae', has been observed for the first time. This paper gives a survey of these structures and illustrates their taxonomic importance and its implications.     

Flow cytometric,chromosomal and morphometric analyses challenge current taxonomic concepts in the Portulaca oleracea complex (Portulacaeae,Caryophyllales)

Portulaca oleracea is a noxious annual weed of worldwide distribution in temperate to tropical climates. Its taxonomy has been treated in contradictory ways in the past. Various microspecies have been described, lumped into a single species by other authors. We re‐examined the importance of seed size and ploidy variation, previously applied as the most important taxonomic characters, for systematic classification based on accessions from Europe, Asia, Africa and South America using flow cytometry, chromosome counting and morphometry. Sixteen microspecies and six transitional forms, covering the ploidy and seed character variation, proposed for the complex, were studied from 178 populations. Portulaca grandiflora was included as a reference species from outside the complex. DNA hyper‐pentaploidy or hexaploidy were inferred for the majority of accessions which exhibited the full range of seed size. It is recommended that the only species of lower ploidy (either diploid based on x = 12 or tetraploid based on x = 12) encountered, P. nicaraguensis, should be separated from the P. oleracea complex as it deviates in base chromosome number and monoploid genome size. The frequency distribution of seed size was continuous and unimodal within the wild taxa of the complex and in pairs of taxa defined by testa sculpture. Seed size of DNA hexaploids was slightly negatively correlated with sample/standard fluorescence intensities. Our results conflict with the current microspecies concept. Possible reasons underlying the discrepancy are discussed and strategies for future systematic research are suggested. © 2015 The Linnean Society of London, Botanical Journal of the Linnean Society, 2015, 179 , 144–156.