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.     

Diketopiperazines from two strains of South China Sea sponge-associated microorganisms

The paper reports the isolation and structural elucidation of seven diketopiperazines from the title microorganisms. Although all isolates are known, three of which were isolated from the actinomycetes for the first time. And this is also the first report to isolate four DKPs from the D. avara-associated microorganism.     

Ent-3,4-seco-labdane and ent-labdane diterpenoids from Croton stipuliformis (Euphorbiaceae)

From a methanolic extract of the leaves of Croton stipuliformis, three ent-3,4-seco-labdanes (1-3) and an ent-labdane (4) together with the known compounds 6-hydroxynidorellol (5), maravuic acid, and sitosterol were isolated and identified from their spectroscopic data. The absolute stereochemistry of compound 4 was determined by application of Mosher's method in the NMR tube.     

Circadian expression of clock and screening of clock-controlled genes in peripheral lymphocytes of rat

In this paper, the circadian pattern of Clock and genes mediated by the Clock was investigated in peripheral lymphocytes of rats. Circadian rhythms of Clock are found under the regimes of constant darkness (DD) and 12-h light-12-h dark (LD12:12h), with the peak phase at CT7 and ZT21, respectively. Ten differential cDNA fragments were identified to be mediated by the Clock, including three known genes (catalase, myelin proteolipid protein, and histone acetylase), four known expressed sequence tags (ESTs), and three novel ESTs. Experiment of the RNA interference revealed that these ESTs were down-regulated by the Clock gene and three of them were identified as clock-controlled genes. Understanding of clock-mediated genes may lead to a new direction in drug design for control of circadian rhythms.     

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.     

A newly-identified lineage of Schistosoma

Because of their role in causing schistosomiasis, flukes of the genus Schistosoma are the best known of all digeneans. The genus has traditionally been divided into four familiar species groups. Here we report on three poorly known species of Schistosoma, one of which, Schistosoma hippopotami, is known from the hippopotamus, one of which is provisionally identified as Schistosoma edwardiense, another hippo parasite, and a third that has not previously been described. All were collected from freshwater snails obtained from Lake Edward, western Uganda, the type locality for both known hippo schistosomes. The three different kinds of schistosome cercariae differ from one another in size, and all are readily differentiated by their long tail stems from the cercariae of human-infecting species. Furthermore, each was recovered from a different genus of snail host, Biomphalaria sudanica, Bulinus truncatus or Ceratophallus natalensis. Molecular analysis, based on 8350 bases of combined nuclear and mitochondrial DNA, groups these three long tail-stem cercariae into a well supported clade that does not associate with any of the recognised species groups. The placement of this clade, basal to all African species plus several Asian species, suggests that there has been an ancient association between Schistosoma and hippos. This new African Schistosoma clade advocates the need for further modification of the traditional species group-based classification. Two of the four species groups are paraphyletic. It also suggests that Schistosoma has been remarkably plastic with respect to adapting to snail hosts-three distantly related genera of planorbid snails have been exploited by worms within a single clade. Finally, it adds a new layer of complexity to deciphering the origins of Schistosoma, often considered to be African but recently challenged as being Asian. In the late Cenozoic the distribution of hippo species straddled both Africa and Asia and they may have provided a means for the introduction of blood flukes to Africa.     

3-Keto steroids from the marine organisms Dendrophyllia cornigera and Cymodocea nodosa

The new (20R)-22E-cholesta-4,22-diene-3,6-dione (1), along with three known 3-keto steroids were isolated from the deep-water Mediterranean scleractinian coral Dendrophyllia cornigera (2-4). Moreover, four known related 3-keto steroids were isolated from the sea grass Cymodocea nodosa (5-8). The structure elucidation of steroid 1 and the full NMR resonance assignments of all isolated metabolites were based on interpretation of their spectral data. All compounds are reported for the first time as metabolites of the investigated organisms. Compounds 2 and 3 showed significant cytotoxicity against lung cancer NSCLC-N6 cell line.     

Firefly luciferase genes from the subfamilies Psilocladinae and Ototretinae (Lampyridae, Coleoptera)

Firefly luciferase genes have been isolated from approximately 20 species of Lampyrinae, Luciolinae, and Photurinae. These are mostly nocturnal luminescent species that use light signals for sexual communication. In this study, we isolated three cDNAs for firefly luciferase from Psilocladinae (Cyphonocerus ruficollis) and Ototretinae (Drilaster axillaris and Stenocladius azumai), which are diurnal non-luminescent or weakly luminescent species that may use pheromones for communication. The amino acid sequences deduced from the three cDNAs showed 81-89% identities to each other and 60-81% identities with known firefly luciferases. The three purified recombinant proteins showed luminescence and fatty acyl-CoA synthetic activities, as observed in other firefly luciferases. The emission maxima by the three firefly luciferases (λmax, 545-546 nm) were shorter than those by known luciferases from the nocturnal fireflies (λmax, 550-568 nm). These results suggest that the primary structures and enzymatic properties of luciferases are conserved in Lampyridae, but the luminescence colors were red-shifted in nocturnal species compared to diurnal species.     

Acylated cyanidin 3-sambubioside-5-glucosides in three garden plants of the Cruciferae

Seven acylated cyanidin 3-sambubioside-5-glucosides were isolated from the flowers of three garden plants in the Cruciferae. Specifically, four pigments were isolated from Lobularia maritima (L.) Desv., together with a known pigment, as well as, three pigments from Lunaria annua L., and two known pigments from Cheiranthus cheiri L. These pigments were determined to be cyanidin 3-O-[2-O-((acyl-II)-(beta-d-xylopyranosyl))-6-O-(acyl-I)-beta-d-glucopyranoside]-5-O-[6-O-(acyl-III)-beta-d-glucopyranoside], in which the acyl-I group is represented by glucosyl-p-coumaric acid, p-coumaric acid and ferulic acid, acyl-II by caffeic acid and ferulic acid, and acyl-III by malonic acid, respectively. The distribution and biosynthesis of acylated cyanidin 3-sambubioside-5-glucosides are discussed according to the variations of acylation and glucosylation at their 3-sambubiose residues.     

Terrestrins A-G: p-terphenyl derivatives from the inedible mushroom Thelephora terrestris

Seven p-terphenyl derivatives named terrestrins A-G together with three known ganbajunin B, thelephantins F and H, were isolated from the methanol extract of fruiting bodies of the Japanese inedible mushroom Thelephora terrestris (Thelephoraceae). Their structures were elucidated by means of high-resolution MS, 2D NMR, IR and UV spectroscopy, and X-ray crystallographic analysis.     

Acetophenone C-glucosides and stilbene O-glucosides in Upuna borneensis

Three acetophenone C-glycosides; 2,4,6-trihydroxyacetophenone 3-C-beta-(2'-O-p-hydroxybenzoyl)-glucopyranoside, 2,4,6-trihydroxyacetophenone 3-C-beta-(2'-O-E-coumaroyl)-glucopyranoside, 2,4,6-trihydroxyacetophenone 3-C-beta-(2'-O-E-cinnamoyl)-glucopyranoside, and two resveratrol O-glycosides; piceid 2'-O-p-hydroxybenzoate and, piceid 2'-O-E-ferulate, together with three known compounds were isolated from the acetone soluble part of stem of Upuna borneensis (Dipterocarpaceae). The structures of isolates were determined by spectral analysis including extensive 2D-NMR spectral analyses.     

4'-deoxy iridoid glycosides from Centranthus longiflorus

The new iridoid glycosides, 4'-deoxykanokoside A and 4'-deoxykanokoside C, were isolated from the methanolic root extract of Centranthus longiflorus ssp. longiflorus. They were accompanied by the three known iridoid glycosides, kanokoside A, kanokoside C and valerosidatum, and two known phenylpropanoid glycosides, coniferin and isoconiferinoside. The structures were elucidated mainly by spectroscopic methods. The presence of 4-deoxy glucose as a part of plant glycosides is rather unusual. Cytotoxic effects of the isolated compounds were also investigated.     

Phenolic glucosides from Hasseltia floribunda

The leaves of Hasseltia floribunda were examined for their chemical constituents. Twelve phenolic glucosides, namely three hydroxycyclohexenyl acyl glucosides, four acylated salicortin derivatives, and five coumaroyl salicin derivatives, were isolated along with eight known phenolic glycosides, six known flavones, and two known sesquiterpenoid cyclohexenone derivatives. The structures of the isolated compounds were elucidated by NMR spectroscopic and HRMS spectrometric methods and by comparing analytical data with those of related structures.     

10-Phenyl-[11]-cytochalasans from Indonesian mushroom Microporellus subsessilis

10-Phenyl-[11]-cytochalasans (4-6), together with three known derivatives (1-3), were isolated from the MeOH extract of the Indonesian mushroom Microporellus subsessilis by a bioassay-guided fractionation. The compounds 6 and 1-3 induced immotility in Artemia salina.     

Three acylated flavone glycosides from Sideritis ozturkii Aytac & Aksoy

From the aerial parts of Sideritis ozturkii, three new flavonoids, chrysoeriol 7-O-[2'-O-caffeoyl-O-acetyl-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside], chrysoeriol 7-O[2'-O-caffeoyl-beta-D-glucopyranosyl-(1 -->2)-beta-D-glucopyranoside] and chrysoeriol 7-O[2'-O-p-coumaroyl-6'-beta-O-acetyl-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside] named as ozturkosides A, B and C, respectively, were isolated, along with three known phenylethanoid glycosides, verbascoside, leucoseptoside A, martynoside and five known diterpenoids, 7-epicandicandiol, linearol, sidol, sideroxol, epoxyisolinearol. The structures were elucidated mainly by spectroscopic methods.     

Dihydroisocoumarins and a tetralone from Cytospora eucalypticola

Two dihydroisocoumarins, 3,5-dimethyl-8-hydroxy-7-methoxy-3,4-dihydroisocoumarin and 3,5-dimethyl-8-methoxy-3,4-dihydroisocoumarin were isolated from a culture filtrate of Cytospora eucalypticola, together with three known dihydroisocoumarins and a tetralone derivative. Their structures were determined by spectroscopic methods. These isocoumarins are mildly antifungal, and antibacterial towards gram positive bacteria. A known compound, 5-hydroxymethylmellein, showed mild antifeedant activity towards Spodoptera littoralis.     

Cucurbitacins from Bacopa monnieri

Four cucurbitacins, bacobitacin A-D (1-4) as well as, a known cytotoxic, cucurbitacin E (5) together with three known phenylethanoid glycosides, monnieraside I, III and plantioside B were isolated form the aerial part of Bacopa monnieri. Their structures were elucidated on the basis of extensive spectroscopic investigations (1D, 2D NMR and ESI-QTOF-MS/MS). This is the first report on the characterization of cucurbitacins in B. monnieri.     

Constituents of Chrysothamnus viscidiflorus

A phytochemical investigation of the aerial parts of Chrysothamnus viscidiflorus var. viscidiflorus afforded three new [chrysothol (1), 2 and 4] and seven known compounds, including five sesquiterpenes, two cinnamic acid derivatives, two ketoalcohol derivatives and one coumarin glucoside. The structures of two previously reported compounds, 1b and 1c, were revised on the basis of chemical reaction. Structures of the compounds were determined by extensive NMR studies, including DEPT, COSY, NOE, HMQC, HMBC and X-ray analysis. The unpublished X-ray data of the known compounds 6 and 7 are reported. Compounds chrysothol (1), and 8-10 showed anti-cancer activity against human breast cancer cells.     

Trichomycete symbiotes of Crozetia seguyi, a primitive black fly

Crozetia is a genus of black flies endemic to the Crozet Islands in the Indian Ocean. No internal symbiotes were previously known from Crozetia species. We report two species of trichomycete symbiotes Stachylina litoralis and Smittium culicisoides from Crozetia seguyi. Larvae of C. seguyi were examined from three sites. The infection rates for St. litoralis was 10.0-33.3% (n=47) of the larvae and Sm. culicisoides was 46.1-85.7% (n=47). No other symbiotes were discovered.     

Iridoid glucosides from Kickxia abhaica D.A. Sutton from Scrophulariaceae

Two iridoid glucosides namely; 6-acetylantirrinoside (1), 6'-O-p-hydroxybenzoylantirrinoside (2) were isolated from the aerial parts of Kickxia abhaica. Beside that, three known iridoid glucosides, antirrinoside (3), antirride (4) and mussaenosidic acid (5), one flavone glycoside (6) and a hexitol, d-mannitol (7) were isolated. The structures of the iridoid glucosides 1-2 were established by 1D and 2D NMR spectral data, including COSY, HMQC and HMBC experiments, as well as HRMS.