New acylated sulfoglycolipids and digalactolipids and related known glycolipids from cyanobacteria with a potential to inhibit the reverse transcriptase of HIV-1

Five novel diacylated sulfoglycolipids (1-5) were isolated from the cyanobacterium Scytonema sp. (TAU strain SL-30-1-4) and four novel acylated diglycolipids (6-9) were isolated from the cyanobacterium Oscillatoria raoi (TAU strain IL-76-1-2). These two groups of glycolipids and related known glycolipids isolated from these two and three other strains of cyanobacteria, Phormidium tenue (TAU strain IL-144-1), O. trichoides (TAU strain IL-104-3-2), and O. limnetica (TAU strain NG-4-1-2), were found to inhibit HIV-1 RT enzymatic activity to different extents. The structure elucidation of the various compounds is based on the selective hydrolysis of the glycerol ester moieties, GCMS analysis of the methyl ester derivatives of the liberated fatty acids, homo- and heteronuclear-2D-NMR techniques, and MS. The use of negative-ion FABMS for analyzing the combination and distribution of the fatty acids in glycolipids is demonstrated.     

Triterpenes and saponins from Rudgea viburnioides

A novel triterpene, viburgenin (1), has been isolated from an extract of the ripe fruit rinds of Rudgea viburnioides, together with the known saponins, arjunglucoside I and trachelosperosides B-1 and E-1, and the triterpenes trachelosperogenin B (2) and arjungenin. Compound 2 was previously obtained as a product from enzymatic hydrolysis, and it is reported for the first time as a natural product. The structure of compound 1 was determined as 2alpha,3beta, 19alpha,23,24-pentahydroxyurs-12-ene by extensive use of 1D and 2D NMR spectroscopic methods. Compound 1 exhibited moderate antifungal activity against Cladosporium cladosporioides.     

Pseudoverdin, a compound related to the pyoverdin chromophore from a Pseudomonas aeruginosa strain incapable to produce pyoverdins

From a genetically manipulated strain of Pseudomonas aeruginosa ATCC 15692 (PAO1 strain) a compound named pseudoverdin, 3-formylamino-6,7-dihydroxycoumarin, was obtained which is related to the typical pyoverdin chromophore and thus allows to shed some light on the biogenesis of the latter.     

Triterpenes and triterpenoid saponins from Mussaenda pubescens

Two novel triterpenoid saponins, named mussaendosides U and V, together with one known saponin and four known triterpenes were isolated from the aerial parts of Mussaenda pubescens (Rubiaceae). The structures were determined on the basis of chemical analysis ad spectral methods. All these compounds were identified for the first time from the genus Mussaenda.     

Triterpenoid saponins and sapogenins from Vaccaria segetalis

When two species have predators in common, animals might be able to obtain important information about predation risk from the alarm calls produced by the other species. The behavioural responses of adult yellow-bellied marmots, Marmota flaviventris, and golden-mantled ground squirrels, Spermophilus lateralis, to conspecific and heterospecific alarm calls were studied to determine whether interspecific call recognition occurs in sympatric species that rarely interact. In a crossed design, marmot and squirrel alarm calls were broadcast to individuals of both species, using the song of a sympatric bird as a control. Individuals of both species responded similarly to conspecific and heterospecific anti-predator calls, and distinguished both types of alarms from the bird song. These results indicate that both marmots and squirrels recognized not only their own species' anti-predator vocalizations, but also the alarm calls of another species, and that these vocalizations were discriminated from an equally loud non-threatening sound. These findings suggest that researchers ought to think broadly when considering the sources of information available to animals in their natural environment. Copyright 1998 The Association for the Study of Animal Behaviour Copyright 1998 The Association for the Study of Animal Behaviour.     

Triterpene saponins from Abrus cantoniensis (Leguminosae). II. Characterization of six new saponins having a branched-chain sugar

A two-part study was conducted to determine the sources of variation in nasalance scores derived from the Nasometer. In Study #1, a function generator was used as a signal source to calibrate and input sine and square waves directly into the Nasometer. Ten stimuli ranging from 105 to 330 Hz in 25 Hz increments were evaluated. In Study #2, the same signal source and an amplified loudspeaker were used to calibrate and present square waves to the nasometer via five different sets of microphones. The sound pressure level of all stimuli was maintained at 88 dB. Each microphone set was calibrated using the 105 Hz signals. Results from Study #1 indicated consistent nasalance scores across all frequencies (i.e., all scores were within 2% of calibration). Results from Study #2 demonstrated deviations greater than 2% from calibration as a function of frequency for all five sets of microphones. The smallest deviation was 5%, whereas the largest deviation was 14%. We suggest that the variation in nasalance as a function of stimulus frequency may be due to a mismatch in the sensitivity of microphones (i.e., different frequency response characteristics). It is further suggested (a) that individual investigators determine the response characteristics of their microphones and (b) that relatively small variations in nasalance scores (i.e., 5-14%) either within or across speakers be interpreted with caution.     

Hydroxycinnamoyl ester glycosides and saponins from flowers of Verbascum phlomoides

A new iridoid ester glycoside acylated with p-coumaric acid was isolated from the flowers of Verbascum phlomoides, together with one known one, specioside. Caffeic acid esters, verbascoside and forsythoside B were found as minor constituents. A new saponin was also obtained and identified as desrhamnosylverbascosaponin.     

Inhibition of influenza virus hemagglutinin-mediated membrane fusion by a compound related to podocarpic acid

Entry of influenza virus into the host cell is dependent on the fusion of the viral envelope with the endosomal membrane and is mediated by a low-pH-induced change of the viral hemagglutinin (HA) to a conformation that is fusogenic. A compound related to podocarpic acid (180299) was identified that inhibits multicycle replication of influenza A/Kawasaki/86 (H1N1) virus in culture. Treatment of Madin-Darby canine kidney (MDCK) cells with 180299 at 1 h before infection resulted in the inhibition of viral protein synthesis. Addition of 20 microgram of 180299/ml at 1 h p.i. had no effect, indicating that 180299 affects an early step of the influenza viral replication cycle. Genetic analysis of reassortants between sensitive and resistant viruses demonstrated that hemagglutinin (HA) conferred the 180299-resistant (180299(r)) phenotype. Twelve independent isolates of influenza A/Kawasaki/86 were selected for resistance to 180299, and sequence analysis revealed that each of these viruses contained amino acid substitutions in the HA. These mutations are dispersed throughout the HA primary amino acid sequence and cluster in one of two regions: the interface between HA1 and HA2 and in a region near the fusion domain of HA2. When compared with the parent virus, the pH-of-inactivation of the resistant mutants was increased by 0.3 to 0.6 pH unit, suggesting that the mutant HAs undergo the conformational change at an elevated pH. Fusion of human erythrocytes to MDCK cells infected with parent influenza A/Kawasaki/86 was inhibited by 180299 (0.1-10 microgram/ml) in a concentration-dependent manner, whereas fusion of erythrocytes to MDCK cells infected with 180299(r) mutants was not affected. These results suggest that 180299 interacts with the neutral pH conformation of influenza A HA and prevents the low-pH-induced change of HA to its fusogenic conformation.     

Asterlingulatosides C and D, cytotoxic triterpenoid saponins from Aster lingulatus

Over the last few decades, European courses in which 'classical' tropical medicine (i.e. parasitology, entomology, and clinical aspects of tropical diseases) is taught have largely become anachronisms. Most countries in the tropics have their own medical schools and few have much need of expatriate doctors. There do, however, appear to be other ways in which Europeans may still help improve health in the tropics. One is to control the quality of the expatriate nurses who are still in demand in the tropics (often as cheaper, generally less demanding substitutes for doctors). This may be achieved by only training the best, insisting they spend some time after graduation gaining maturity before they leave for the tropics, ensuring they realise that their clinical skills will probably be inferior to their local counterparts in the tropics, and encouraging them to continue studying once abroad. The second way Europeans may help is to change the bias of their courses from teaching to training. There seems little doubt that the intellectual personalities of the brightest young men and women in the tropics often develop far better when they spend a period in a foreign environment, especially when they are allowed to function within a team, with trainees and trainers from other countries. Some 'international' courses may offer such benefits, especially if closely tailored to the needs of the trainees and their home countries.     

Relationship between chemical structures and biological activities of triterpenoid saponins from soybean

Saponins can be found in more than one hundred plant families and in some marine animals. However, chemical investigation of soybean (Glycine max L. Merrill) saponins has begun only as recently as the 1970s. Here we focus on the chemical structure, the content, and biological activity of soybean saponins in current studies. Especially, we focus on 2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP) conjugated saponins and define the chemical structure of this as a natural precursor of group B and E saponins.     

Influence of technetium-99m-labeling conditions on physico-chemical and related biological properties of an acylated poly-galactosidic macrophage targeting agent for inflammation imaging

The potential of 99m-Tc-J001 for the investigation of inflammatory lesions via the targeting of recruited macrophages (M phi) has already been documented in several experimental models and in human diseases. To achieve a functional imaging of inflammation via M phi targeting, minimal labeled colloid content and high in vivo stability of 99mTc-J001 are essential. The actual specificity of such scintigraphy is closely dependent upon the radiolabeling of only the J001 molecules available for M phi targeting. To develop an appropriate radiopharmaceutical kit, optimization of the labeling conditions was achieved from a series of pilot formulations that were evaluated for radiolabeling efficiency and both in vitro and in vivo 99mTc-J001 stability. Colloids were characterized using autocorrelation spectroscopy and multiangle laser-light scattering, radioactive colloid content of the formulations being deduced from biodistribution studies. This work has made possible the definition of a formulation exhibiting a radiolabeling yield > 97.0%, associated with in vivo stability and minimal colloid formation, thus greatly enhancing the specificity of such macrophage scintigraphy.     

Two novel oleanolic acid saponins having a sialyl Lewis X mimetic structure from Achyranthes fauriei root

Two novel triterpene glycosides, achyranthosides E and F, were isolated as methyl esters from the root of Achyranthes fauriei, an antiinflammatory medicinal plant. Their structures were characterized as oleanolic acid glucuronides having unique substituents composed of C6H9O5 and C9H15O7, respectively, at the C-3 position of glucuronic acid. These compounds are active components which can inhibit the excess recruiting of neutrophiles to injured tissues 1,000 times more potently than sialyl Lewis X.     

Antimicrobial activity of a compound isolated from an oil-macerated garlic extract

A compound showing antimicrobial activity was isolated from an oil-macerated garlic extract by silica gel column chromatography and preparative TLC. On basis of the results of NMR and MS analyses, it was identified as Z-4,5,9-trithiadeca-1,6-diene-9-oxide (Z-10-devinylajoene; Z-10-DA). Z-10-DA exhibited a broad spectrum of antimicrobial activity against such microorganisms as gram-positive and gram-negative bacteria and yeasts. The antimicrobial activity of Z-10-DA was comparable to that of Z-ajoene, but was superior to that of E-ajoene. Z-10-DA and Z-ajoene are different in respect of substitution of the allyl group by the methyl group flanking a sulfinyl group. This result suggests that substitution by the methyl group would also be effective for the inhibition of microbial growth.     

Transplantation of a kidney harvested laparoscopically from a related living donor

Transplantation of kidney grafts harvested in living donors has demonstrated better results than grafts harvested from brain dead donors. Recently, laparoscopic live donor nephrectomy has been introduced to reduce the live procurement morbidity. In 1997, we performed two laparoscopic live donor nephrectomy and we report the first case of this program in this paper.     

New antifungal and cytotoxic steroidal saponins from the bulbs of an elephant garlic mutant

Saponins in bulbs of a mutant of elephant garlic were investigated, and three new steroidal saponins named yayoisaponins A-C were obtained together with the known dioscin and aginoside. Their structures, including the relative stereochemistry, were elucidated by spectral data interpretation, while the absolute stereochemistry of the sugar moieties was assigned on the basis of a chiral gas chromatographic analysis of the acid hydrolysates. Yayoisaponins A-C and aginoside exhibited not only in vitro cytotoxicity against P388 cells at 2.1 micrograms/ml, but also antifungal activity against Mortierella ramanniana at 10 micrograms/disk.     

Two new steroidal saponins from Allium sativum and their inhibitory effects on blood coagulability]

Determining the presence of viable myocardium has prognostic and therapeutic implications in the treatment of ischemic heart disease. Dobutamine stress echocardiography (DSE) is one possible technique to help identify both hibernating and stunned but viable myocardium. Low-dose dobutamine infusion has an increased inotropic effect, while higher doses cause both inotropic and chronotropic effects. Thus, at lower doses cardiac augmentation occurs, and at higher doses regions of ischemia may be produced in the presence of significant coronary artery disease. This is manifested echocardiographically as changes in segmental wall motion. In theory, therefore, areas of viable myocardium should show improved wall motion at low doses, and areas of irreversible myocardial damage will remain akinetic. Five studies have investigated DSE for determining viability in the setting of acute myocardial infarction, thus looking for stunned but viable myocardium. DSE was shown to compare favorably with positron emission tomography and was highly sensitive and specific for predicting functional myocardial recovery. Five additional studies examined DSE for determining the presence of hibernating myocardium. The sensitivity and specificity of DSE were found to range from 71 to 92% and from 73 to 93%, respectively. The benefits of DSE include lower cost, convenience to both patient and physician, additional ancillary information, and determination of the possible need for urgent revascularization. Limitations of DSE include occasional technical difficulty in obtaining and interpreting studies and the need for larger volumes of viable myocardium to detect changes predictive of functional recovery. Larger trials are currently underway to confirm DSE as a reliable technique for determining myocardial viability.     

Steroidal saponins from the rhizomes of Hosta sieboldii and their cytostatic activity on HL-60 cells

A total of eighteen steroidal saponins were isolated from the rhizomes of Hosta sieboldii, one of which appeared to be the first isolation from a plant source and six to be new compounds. The structures of the new saponins were determined by spectral data and a few chemical transformations to be (25R)-2 alpha, 3 beta-dihydroxy-5 alpha-spirostan-12-one (manogenin) 3-O-?O-beta-D-glucopyranosyl-(1-->2)-O-beta-D-glucopyranosyl -(1-->4)-beta-D-galactopyranoside?, (25R)-2 alpha,3 beta-dihydroxy-5 alpha-spirost-9-en-12-one (9,11-dehydromanogenin) 3-O-?O-beta-D-glucopyranosyl-(1-->2)-O-beta-D- glucopyranosyl-(1-->4)-beta-D-galactopyranoside?, 9,11-dehydromanogenin 3-O-?O-beta-D-glucopyranosyl-(1-->2)-O-[O-alpha-L- rhamnopyranosyl-(1-->4)-beta-D-xylopyranosyl-(1-->3)]-O-beta-D- glucopyranosyl-(1-->4)-beta-D-galactopyranoside?, (25R)-2 alpha,3 beta-dihydroxy-26-beta-D-glucopyranosyloxy-22-methoxy-5 alpha-furostan-12-one 3-O-?O-beta-D-glucopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O- beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside?, (25R)-2 alpha, 3 beta-dihydroxy-26-beta-D-glucopyranosyloxy-22-methoxy-5 alpha-furost-9-en-12-one 3-O-?O-beta-D-glucopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O- beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside? and (25R)-5 alpha-spirostan-2 alpha,3 beta,12 beta-triol 3-O-?O-alpha-L- rhamnopyranosyl-(1-->2)-beta-D-galactopyranoside?, respectively. Cytostatic activity of the isolated saponins on leukaemia HL-60 cells was examined.