Growth and energy budget of F2'all-fish' growth hormone gene transgenic common carp

The growth and energy budget for F₂‘all‐fish’ growth hormone gene transgenic common carp Cyprinus carpio of two body sizes were investigated at 29·2° C for 21 days. Specific growth rate, feed intake, feed efficiency, digestibility coefficients of dry matter and protein, gross energy intake (I_E), and the proportion of I_E utilized for heat production (H_E) were significantly higher in the transgenics than in the controls. The proportion of I_E directed to waste products [faecal energy (F_E) and excretory energy loss (Z_E+U_E) where Z_E is through the gills and U_E through the kidney], and the proportion of metabolizable energy (M_E) for recovered energy (R_E) were significantly lower in the transgenics than in the controls. The average energy budget equation of transgenic fish was as follows: 100 I_E= 19·3 F_E+ 6·0 (Z_E+U_E) + 45·2 H_E+ 29·5 R_E or 100 M_E= 60·5 H_E+ 39·5 R_E. The average energy budget equation of the controls was: 100 I_E= 25·2 F_E+ 7·4 (Z_E+U_E) + 35·5 H_E+ 31·9 R_E or 100 M_E= 52·7 H_E+ 47·3 R_E. These findings indicate that the high growth rate of ‘all‐fish’ transgenic common carp relative to their non‐transgenic counterparts was due to their increased feed intake, reduced lose of waste productions and improved feed efficiency. The benefit of the increased energy intake by transgenic fish, however, was diminished by their increased metabolism.     

Determination of the driving force of the Na+ pump in toad bladder by means of vasopressin

Summary Vasopressin stimulates Na⁺ transport across toad bladder largely or entirely by decreasing the resistance to Na⁺ entry into the transporting epithelial cells. Therefore, the hormone should induce proportional changes in short circuit current (I _S ) and tissue conductance; the ratio of these changes should equal the driving force (E _Na) of the Na⁺ pump.Administration of vasopressin provided a rapid, reversible and reproducible technique for the measurement ofE _Na. Values calculated forE _Na ranged from 74 to 186 mV, in agreement with previously published estimates. The results were not dependent on the vasopressin concentration over a wide range of concentrations.Ouabain, an agent thought to inhibit specifically the Na⁺ pump, decreased bothI _S andE _Na. On the other hand, amiloride, a diuretic thought to block specifically Na⁺ entry, markedly reducedI _S , without reducingE _Na.It is concluded that vasopressin constitutes a probe for the rapid reproducible determination ofE _Na under a wide variety of physiological conditions.     

Diet and trophic niche of Antarctic silverfish Pleuragramma antarcticum in the Ross Sea,Antarctica

The diet of Antarctic silverfish Pleuragramma antarcticum was evaluated by examining stomach contents of specimens collected in the Ross Sea (71°–77° S; 165°–180° E) in January to March 2008. Pleuragramma antarcticum (50–236 mm standard length, L_S) and prey items were analysed for stable‐isotopic composition of carbon and nitrogen. According to index of relative importance (I_RI), which incorporates frequency of occurrence, mass and number of prey items, the most important prey items were copepods (81%I_RI over all specimens), predominantly Metridia gerlachei and Paraeuchaeta sp., with krill and fishes having low I_RI (2·2 and 5·6%I_RI overall). According to mass of prey (M) in stomachs, however, fishes (P. antarcticum and myctophids) and krill dominated overall diet (48 and 22%M, respectively), with copepods being a relatively minor constituent of overall diet by mass (9·9%M). Piscivory by P. antarcticum occurred mainly in the extreme south‐west of the region and near the continental slope. Krill identified to species level in P. antarcticum stomachs were predominantly Euphausia superba (14·1%M) with some Euphausia crystallophorias (4·8%M). Both DistLM modelling (PRIMER‐permanova+) on stomach contents (by I_RI) and stepwise generalized linear modelling on stable isotopes showed that L_S and location were significant predictors of P. antarcticum diet. Postlarval P. antarcticum (50–89 mm L_S) consumed exclusively copepods. Juvenile P. antarcticum (90–151 mm L_S) consumed predominantly krill and copepods by mass (46 and 30%M, respectively). Small adult P. antarcticum (152–178 mm L_S) consumed krill, fishes and copepods (37, 36 and 15%M, respectively). Large adult P. antarcticum (179–236 mm L_S) consumed predominantly fishes and krill (55 and 17%M, respectively), especially in the north (near the Ross Sea slope) and in the SW Ross Sea. Amphipods were occasionally important prey items for P. antarcticum (western Ross Sea, 39%M). General concordance between stomach contents and trophic level of P. antarcticum and prey based on δ¹⁵N was demonstrated. Pleuragramma antarcticum trophic level was estimated as 3·7 (postlarval fish) and 4·1 (fish aged 3+ years).     

Additive genetic variance within populations derived by single-seed descent and pod-bulk descent

Summary Breeders of self-pollinated legumes commonly use single-seed descent (SSD) or pod-bulk descent (PBD) to produce segregating populations of highly inbred individuals. We presented equations for the expected value of the additive genetic variance within populations derived by SSD (E(V _A)_SSD) and PBD (E(V _A)_PBD) in terms of the initial population size (N ₀), the number of seed harvested per pod (M), the probability of survival of an individual (), and the generation at which the population is evaluated (S _t). Differences between (E(V _A)_SSD) and (E(V _A)_PBD) are due to differences in the expected amount of random drift which occurs with the two methods after the S ₀ generation. With both methods, random drift occurs when progeny are sampled from heterozygous parents. An additional component of random drift occurs when sampled progeny fail to survive during SSD, or when sampling occurs amoung families during PBD. For values of N ₀, M, , and S _t that are typical of soybean (Glycine max (L.) Merr.) breeding programs, (E(V _A)_SSD) will be greater than (E(V _A)_PBD). The ratio of (E(V _A)_SSD) to (E(V _A)_PBD) will: (1) increase as M and increase; (2) approach a value of 1.00 as N ₀ increases; and (3) be a curvilinear function of S _t. Plant breeders should compare SSD and PBD based upon values of (E(V _A)_SSD) and (E(V _A)_PBD) and the expected cost of carrying out the two methods.Contribution No. 2910 of the South Carolina Agricultural Experiment Station, Clemson University     

Changes in grassland ecosystem function due to extreme rainfall events: implications for responses to climate change

Climate change is causing measurable changes in rainfall patterns, and will likely cause increases in extreme rainfall events, with uncertain implications for key processes in ecosystem function and carbon cycling. We examined how variation in rainfall total quantity (Q), the interval between rainfall events (I), and individual event size (S_E) affected soil water content (SWC) and three aspects of ecosystem function: leaf photosynthetic carbon gain (), aboveground net primary productivity (ANPP), and soil respiration (). We utilized rainout shelter‐covered mesocosms (2.6 m³) containing assemblages of tallgrass prairie grasses and forbs. These were hand watered with 16 I×Q treatment combinations, using event sizes from 4 to 53 mm. Increasing Q by 250% (400–1000 mm yr^?1) increased mean soil moisture and all three processes as expected, but only by 20–55% (P≤0.004), suggesting diminishing returns in ecosystem function as Q increased. Increasing I (from 3 to 15 days between rainfall inputs) caused both positive () and negative () changes in ecosystem processes (20–70%, P≤0.01), within and across levels of Q, indicating that I strongly influenced the effects of Q, and shifted the system towards increased net carbon uptake. Variation in S_E at shorter I produced greater response in soil moisture and ecosystem processes than did variation in S_E at longer I, suggesting greater stability in ecosystem function at longer I and a priming effect at shorter I. Significant differences in ANPP and between treatments differing in I and Q but sharing the same S_E showed that the prevailing pattern of rainfall influenced the responses to a given event size. Grassland ecosystem responses to extreme rainfall patterns expected with climate change are, therefore, likely to be variable, depending on how I, Q, and S_E combine, but will likely result in changes in ecosystem carbon cycling.     

A 4-oxo-2(E)-nonenal-derived glutathione adduct from 15-lipoxygenase-1-mediated oxidation of cytosolic and esterified arachidonic acid

15(S)-Hydroperoxy-[5Z,8Z,11Z,13E]-eicosatetraenoic acid (15(S)-HpETE) undergoes homolytic decomposition to bifunctional electrophiles such as 4-oxo-2(E)-nonenal. 4-Oxo-2(E)-nonenal reacts with glutathione to form a thiadiazabicyclo-4-oxo-2(E)-nonenal–glutathione adduct (TOG). Therefore, this endogenous glutathione adduct can serve as a specific biomarker of lipid hydroperoxide-mediated 4-oxo-2(E)-nonenal formation. A monocyte/macrophage cell line was generated to constitutively express human 15-lipoxygenase-1. In these cells, TOG was formed from 15(S)-HpETE-derived 4-oxo-2(E)-nonenal in a nonlinear dose-dependent manner upon arachidonic acid treatment. The lipoxygenase inhibitor cinnamyl-3,4-dihydroxy-α-cyanocinnamate abolished arachidonic acid-mediated TOG formation. The calcium ionophore A23187 was also used to induce the formation of 15(S)-HpETE from esterified arachidonic acid present in the membrane lipids. In the 15-lipoxygenase-1-expressing cells, the calcium ionophore A23187 significantly increased TOG levels compared with mock-transfected cells. This was due to the 15-lipoxygenase-mediated formation of 15(S)-HpETE in the forms of free fatty acid and esterified lipids, which was subsequently converted to 4-oxo-2(E)-nonenal. The increase in TOG formation was again abrogated by pretreatment with cinnamyl-3,4-dihydroxy-α-cyanocinnamate. Only 8.7% 15(S)-HETE (both the free fatty acid and its esterified form in the cell membrane) was formed after ionophore A23187 stimulation compared with that formed after the addition of arachidonic acid. In contrast, the TOG levels after treatment with ionophore A23187 or arachidonic acid were comparable. Thus, it is likely that esterified 15(S)-HpETE underwent homolytic decomposition to 4-oxo-2(E)-nonenal more efficiently than the free 15(S)-HpETE that was formed in the cytosol.     

Comparison of Soybean Tissue Extracted with Different Solvents

The enantioselective hydrolysis of (R,S)-3-acetoxymethyl-7,8-difluoro-2,3-dihydro-4H-[1,4]benzoxazine (I) with enzymes was investigated. Optically active I and its hydrolyzate, 7,8-difluoro-2,3-dihydro-3-hydroxymethyl-4H-[1,4]benzoxazine (II), are the intermediates for preparing optically active ofloxacins, whose racemate is known to be an excellent antibacterial agent. Lipoprotein lipase from Pseudomonas fluorescens (LPL Amano 3) was found to predominantly hydrolyze (S)-I, giving (R)-I in 54% e.e. and (R)-II in 44% e.e. On the other hand, lipase from Candida cylindracea was found to predominantly hydrolyze (R)-I, giving (S)-I in 24% e.e. and (S)-II in 20% e.e. Since, the optical purities of I and II thus obtained were not particularly high, these optically active I and II were converted into 3-acetoxymethyl-7,8-difluoro-2,3-dihydro-4-(3,5-dinitrobenzoyl)-4H-[1,4]benzoxazine (IV). After recrystallizing IV from ethyl acetate-hexane, (S)- and (R)-II were obtained with high enantiomeric excess by removing the crystallized racemic IV and subsequently hydrolyzing the resulting optically active IV with alkali. The reduction of II afforded 7,8-difluoro-2,3-dihydro-3-methyl-4H-[1,4]benzoxazine (III), for which the optical purity was estimated to be >96%e.e. by HPLC analysis. (R)- and (S)-ofloxacin were prepared from (R)- and (S)-III with retention of their configuration.     

Spatial and seasonal variations in stem CO2 efflux of Pinus canariensis at their upper distribution limit

We calculated stem CO₂ efflux (E _S) of Pinus canariensis at a timberline site in Tenerife, Canary Islands, from March 7, 2008 and February 9, 2009. E _S varied markedly throughout the year. Although E _S generally followed the seasonal trends in temperature, we observed seasonal adjustment of E _S in both E _S normalized to temperature (E _S10) and the temperature sensitivity (Q ₁₀) resulting in lower E _S10 values during the warm and dry season as compared during the cold and wet season; the latter corresponding with the period of stem growth. The Q ₁₀ by contrast, was higher during the warm and dry summer than during the cold and wet season, an observation suggesting that climate extremes such as summer drought in the Mediterranean may override the observation that Q ₁₀ declines with increasing temperature. As concurrent measurements estimating the potential impact of sap flow on E _S revealed no interaction in P. canariensis, the Q ₁₀ values were used along with E _S10 and stem temperature records to predict annual total E _S and for partitioning total E _S into its maintenance (E _m) and a growth (E _g) component.     

Ionic mechanisms for the antiarrhythmic action of cinnamophilin in rat heart

We investigated the electrophysiological effect and antiarrhythmic potential of cinnamophilin (Cinn), a thromboxane A₂ antagonist isolated fromCinnamomum philippinense, on rat cardiac tissues. Action potential and ionic currents in single rat ventricular cells were examined by current clamp or voltage clamp in a whole-cell configuration. In 9 episodes of ischemia-reperfusion arrhythmia, 10 µM Cinn converted 6 of them to normal sinus rhythm. Cinn suppressed the maximal rate of rise of the action potential upstroke (V_max) and prolonged the action potential duration at 50% repolarization (APD₅₀). Voltage clamp study showed that the suppression of V_max by Cinn was associated with an inhibition of sodium inward current (I_Na, IC₅₀=10.0 ± 0.4 µM). At 30 µM, V_1/2 for the steady-state inactivation curve of I_Na was shifted from –84.1 ± 0.2 to –93.0 ± 0.5 mV. Cinn also reduced calcium inward current (I_Ca) dose-dependently with an IC₅₀ value of 9.5 ± 0.3 µM. Cinn (10 µM) reduced the I_Ca with a negative shift of V_1/2 for the steady-state inactivation curve of I_Ca from –32.2 ± 0.3 to –50.7 ± 0.4 mV. The prolongation of APD₅₀ was associated with an inhibition of the integral of potassium outward current with IC₅₀ values between 4.8 and 7.1 µM. At 10 µM, Cinn reduced I_Na without a negative shift of its voltage-dependent steady-state inactivation curves. The inhibition of transient outward current (I_to) by Cinn (3–30 µM) was associated with an acceleration of its time constant of inactivation and negative shift of its potential-dependent steady-state inactivation curves. The equilibrium dissociation constant (K_d) of Cinn to inhibit open state I_to channels, as calculated from the time constant of developing block, was 18.3 µM. The time constant of recovery of I_to from inactivation state was unaffected by Cinn. The rate constant for the relief from the depolarization-dependent block of I_to was calculated to be 23.9 ms. As compared with its effect on I_to, Cinn exerted about half the potency to block I_Na and I_Ca. These results indicate that the inhibition of I_Na, I_Ca and I_to may contribute to the antiarrhythmic activity of Cinn against ischemia-reperfusion arrhythmia.     

Synthesis of (S)-13-Hydroxy (2E,4E,8E)- and (2E,4E,8Z)-Tetradecatrienoic Acids

The syntheses of (S)-13-hydroxy-(2E,4E,8E)-tetradecatrienoic acid (1) and (2E,4E,8Z)-tetradecatrienoic acid (2) were carried out by using the Wittig reaction as the key step. The asymmetric center at C-13 and the double bond between C-8 and C-9 for natural compound 1 were reconfirmed as being of (S) configuration and E, respectively.

The relationship between the structure of the unsaturated hydroxy fatty acids and their inhibitory effect on the growth of lettuce was investigated.     

Review of the genus Eusterinx Förster, 1869 (Hymenoptera: Ichneumonidae: Orthocentrinae) with descriptions of five new species from South Korea

South Korean species of the genus Eusterinx Förster are reviewed here. Nine species of the genus Eusterinx are found to occur in South Korea, and five species, Eusterinx (E.) elongata sp. nov. , E. (Holomeristus) hirtis sp. nov. , E. (Ischyracis) fulvipes sp. nov. , E. (I.) petiolata sp. nov. and E. (I.) rufithorax sp. nov. , are described. Four more species of Eusterinx from subgenera Divinatrix, Eusterinx and Holomeristus are recorded from South Korea for the first time. Hitherto, unknown male of the Eastern Palaearctic species E. (Divinatrix) kurilensis Humala is described. A key to all known species of the genus Eusterinx occurring in South Korea is provided.     

Chemical analysis of the female sex pheromone in Palpita nigropunctalis (Lepidoptera: Crambidae)

The lilac pyralid, Palpita nigropunctalis Bremer (Lepidoptera: Crambidae), is a common pest of Oleaceae plants. A crude extract of the female sex pheromone glands was examined by gas chromatography-electroantennogram detection (GC-EAD) and GC coupled to a mass spectrometer (GC/MS). The GC-EAD analysis revealed three EAG-active components (I–III) in a ratio of 1:0.2:0.01 (I: II: III). GC/MS analysis successfully recorded the mass spectra of I and II. For I, ions at m/z 238 (M⁺) and 220 ([M-18]⁺) indicated the structure of a monoenyl aldehyde with a 16-carbon chain. For II, M⁺ was not detected, but ions at m/z 222 ([M-60]⁺) and 61 ([AcOH+1]⁺) suggested that II was a monoenyl acetate with a 16-carbon chain. Further GC/MS analysis of the extract treated with dimethyl disulfide revealed that the double bonds in both I and II are located at the same position of 11th-carbon. In addition, the pheromone extract was examined by GC/Fourier transform-infrared spectrophotometer (GC/FT-IR). An IR spectrum of I showed characteristic absorption at 1716 and 966?cm^?1, indicating a formyl group and E configuration of the double bond, respectively. In the case of II, absorption at 1745 and 968?cm^?1 indicated an ester carbonyl and E configuration, respectively. Taken together and by comparison with authentic standards, I and II were confirmed as (E)-11-hexadecenal and (E)-11-hexadecenyl acetate, respectively; while III was speculated as (E)-11-hexadecen-1-ol. The synthetic I, II and III all coincided well with those of the natural components in chemical data, and elicited strong electroantennographic activity in male P. nigropunctalis.     

In situ evaluation of esterase stereoselectivity in two-dimensional electropherograms and tissue sections

Staining with both enantiomers of an α-naphthyl ester plus a diazonium salt and comparing the color intensities given by the two enantiomers is a convenient method to evaluate the esterase stereoselectivity for that ester in two-dimensional electropherograms and tissue sections. Application of this method for rat liver has shown that (1) several esterases, e.g., one of pI 6.4 and M_r 118 kDa, are moderately stereoselective against α-naphthyl (R)-N-acetylalaninate and (R)-N-methoxycarbonylalaninate but strictly stereoselective against α-naphthyl (S)-N-methoxycarbonylvalinate, implying that esterase stereoselectivity may be inverted by changing the ester structure; and (2) these esterases are mainly contained in the hepatocytes around central veins.     

Volatile Methyl Esters of Medium Chain Length from the Bacterium Chitinophaga Fx7914

The analysis of the volatiles released by the novel bacterial isolate Chitinophaga Fx7914 revealed the presence of ca. 200 compounds including different methyl esters. These esters comprise monomethyl‐ and dimethyl‐branched, saturated, and unsaturated fatty acid methyl esters that have not been described as bacterial volatiles before. More than 30 esters of medium C‐chain length were identified, which belong to five main classes, methyl (S)‐2‐methylalkanoates (class A), methyl (S)‐2,(ω?1)‐dimethylalkanoates (class B), methyl 2,(ω?2)‐dimethylalkanoates (class C), methyl (E)‐2‐methylalk‐2‐enoates (class D), and methyl (E)‐2,(ω?1)‐dimethylalk‐2‐enoates (class E). The structures of the compounds were verified by GC/MS analysis and synthesis of the target compounds as methyl (S)‐2‐methyloctanoate ( 28 ), methyl (S)‐2,7‐dimethyloctanoate ((S)‐ 43 ), methyl 2,6‐dimethyloctanoate ( 49 ), methyl (E)‐2‐methylnon‐2‐enoate ( 20a ), and methyl (E)‐2,7‐dimethyloct‐2‐enoate ( 41a ). Furthermore, the natural saturated 2‐methyl‐branched methyl esters showed (S)‐configuration as confirmed by GC/MS experiments using chiral phases. Additionally, the biosynthetic pathway leading to the methyl esters was investigated by feeding experiments with labeled precursors. The Me group at C(2) is introduced by propanoate incorporation, while the methyl ester is formed from the respective carboxylic acid by a methyltransferase using S‐adenosylmethionine (SAM).     

Influence of Carbicron (O-[(2-butenoic acid)-N,N-dimethylamide-3-YL] O,O-dimethylphosphate) on some biochemical and biophysical parameters of rat liver membranes

• 1.1. Treatment of rats with carbicron induced a reduction of the phospholipids in both microsomal and plasma membranes.
• 2.2. A decrease of the structural order parameter (S_DPH) and an increase of the pyrene excimer-to-monomer fluorescence ratio (I_E/I_M) was also observed, indicating membrane fluidization.
• 3.3. The specific activity of membrane-bound phospholipase A₂ and phospholipase C were decreased in both types of membranes, whereas acyl-CoA:lysophosphatidylcholine acyltransferase activity was augmented due to carbicron treatment.

     

Iodine toxicity in a plant-solution system with and without humic acid

Aqueous iodine (I_2(aq)) is a potent disinfectant that is being evaluated as a soil sanitizer for agricultural fields and a water purification treatment for the International Space Station. Rice (Oryza sativa L.) plants were grown in solution culture containing different I compounds at approximately 0, 18, or 30 μM total I [I_2(aq) + iodide (I⁻)] consisting of 0, 6, and 20 μM I as I_2(aq), respectively. In addition, humic acid (HA) was added to half the treatments. Most I_2(aq) was electrochemically reduced to the endpoint metabolite I⁻ within 24 h with HA promoting the response. Plants receiving the highest dose of I_2(aq), particularly those in treatments without HA, had the least growth and the greatest biomass I concentrations. Roots from both I_2(aq) treatments without HA were periodically sampled for bacteria. Viable and direct caints of bacterial cell density declined with increasing I_2(aq) concentrations within the first hour after treatment application. However, cell densities recovered within 96 hours and eventually surpassed the control treatment cell density. Additionally, the resulting high viable: direct count density ratio suggests that opportunistic species likely dominated the post I_2(aq) environment.     

A New Identification Method for Aliphatic Compounds Using Linear Equations of the GC Retention Index Value

The Retention Index (I) value and the different I values from two columns, carbowax 20M (20M) and OV101 (ΔI:I_20M ? I_OV101) of aliphatic compounds were calculated by several kinds of linear equations under programmed linear temperature conditions. The equations could be used to predict appropriate compounds as well as a database of I and ΔI values.     

Production of Cephalosporin Antibiotics by Strains Belonging to the Genera Arachnomyces,Anixiopsis and Spiroidium

The absolute configuration of a phytoalexin “Safynol” (3E, 11E)-3, 11-tridecadiene-5, 7, 9-triyne-l, 2-diol (I), separated from Phytophthora drechsleri-infected safflower (Carthamus tinctorius L.) was confirmed. (R) and (S)-safynol were synthesized from 2, 3-O-isopropyli- dene-(S)- and (R)-glyceraldehyde respectively, and the (R) configuration was assigned to the natural product. The inhibitory effects of (R)- and (S)-safynol on mycelial growth of five fungi were almost the same and their ED₅₀ values ranged from 6 to 70 ppm.     

Isolation of Ceramides from Tagetes patula L. Yellow Flowers and Nematicidal Activity of the Fractions and Pure Compounds against Cyst Nematode,Heterodera zeae

Investigation of yellow flower extract of Tagetes patula L. led to the identification of an aggregate of five phytoceramides. Among them, (2R)‐2‐hydroxy‐N‐[(2S,3S,4R,8E)‐1,3,4‐trihydroxyicos‐8‐en‐2‐yl]icosanamide, (2R)‐2‐hydroxy‐N‐[(2S,3S,4R,8E)‐1,3,4‐trihydroxyicos‐8‐en‐2‐yl]heneicosanamide, (2R)‐2‐hydroxy‐N‐[(2S,3S,4R,8E)‐1,3,4‐trihydroxyicos‐8‐en‐2‐yl]docosanamide, and (2R)‐2‐hydroxy‐N‐[(2S,3S,4R,8E)‐1,3,4‐trihydroxyicos‐8‐en‐2‐yl]tricosanamide were identified as new compounds and termed as tagetceramides, whereas (2R)‐2‐hydroxy‐N‐[(2S,3S,4R,8E)‐1,3,4‐trihydroxyicos‐8‐en‐2‐yl]tetracosanamide was a known ceramide. A steroid (β‐sitosterol glucoside) was also isolated from the subsequent fraction. The structures of these compounds were determined on the basis of spectroscopic analyses, as well as chemical method. Several other compounds were also identified by GC/MS analysis. The fractions and some commercial products, a ceramide HFA, β‐sitosterol, and stigmasterol were evaluated against an economically important cyst nematode, Heterodera zeae. Ceramide HFA showed 100 % mortality, whereas, β‐sitosterol and stigmasterol were 40–50 % active, at 1 % concentration after 24 h of exposure time, while β‐sitosterol glucoside revealed no activity against the nematode.     

Absolute configuration of phomactatriene diterpenoids obtained by Wagner‐Meerwein rearrangement of epimeric verticillols

The epimeric diterpenes (+)‐(1S,3E,7E,11S,12S)‐verticilla‐3,7‐dien‐12‐ol ( 1 ), isolated from Bursera suntui, and (+)‐(1S,3E,7E,11S,12R)‐verticilla‐3,7‐dien‐12‐ol ( 2 ), isolated from Bursera kerberi, gave the same Wagner‐Meerwein rearrangement product (?)‐(1E,4Z,8Z,11S,12R)‐phomacta‐1,(15)4,8‐triene ( 3 ). The Et₂O:BF₃‐induced transformations evidence that verticillenes and phomactanes, both containing the bicyclo[9.3.1]pentadecane skeleton, are biogenetically related through the verticillen‐12‐yl cation ( A ⁺ ), which also is a key intermediate in the biosynthetic pathways to generate antitumor taxanes. Molecular modeling using the Monte Carlo protocol, followed by density functional theory (DFT) geometry optimization employing the hybrid functionals B3LYP and B3PW91, both with the DGDZVP basis set, secured the configuration of 3 as followed from the good agreement between the calculated and experimental vibrational circular dichroism spectra. Similar DFT calculations allowed determining the absolute configuration of (+)‐(1R,4R,5R,8S,9S,11S,12R,15R)‐1,15:4,5:8,9‐triepoxyphomactane ( 9 ), which surprisingly derives from epoxidation of the second minimum energy conformer of 3 .