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1.
The phenolic constituents of the roots ofTaxus cuspidata (Japanese yew) were investigated. Four lignans, [(+)-taxiresinol (1), (+)-lariciresinol (2), (–)-secoisolariciresinol (3), and (+)-pinoresinol (4)] were isolated and identified. The assignment of proton and carbon atoms for the lignans were finally solved by one- and twodimensional-nuclear magnetic resonance spectra. The enantiomeric excess of these lignans were determined by chiral high-performance liquid Chromatographic analyses. (+)-Lariciresinol and (–)-secoisolariciresinol were optically pure; (+)-taxiresinol was also suggested to be optically pure, although (+)-pinoresinol was not (77% enantiomeric excess).  相似文献   

2.
Four lignans — pinoresinol, lariciresinol, secoisolariciresinol, matairesinol — were isolated from each ofDaphne odora andDaphne genkwa (Thymelaeaceae). Matairesinol isolated from both plants was optically pure (>99% e.e.) and dextrorotatory. Pinoresinol and lariciresinol isolated from the plants were not optically pure, and their enantiomeric compositions ranged from 88% to 95% e.e. in favor of (–)-enantiomers. As for secoisolariciresinol, the one fromD. odora was optically pure [(+)-enantiomer, >99% e.e.], and that fromD. genkwa was 97% e.e. in favor of the (+)-enantiomer. Lignan-synthesizing enzyme activity was detected from a Thymelaeaceae plant for the first time; cell-free extracts fromD. genkwa catalyzed the formation of (–)-lariciresinol (23% e.e.) from racemic (±)-pinoresinols. The stereochemistry of the enzymatic reaction is discussed in relation to the stereochemical features of the isolated lignans.Parts of this report were presented at the 42nd Lignin Symposium, Sapporo, October 1997; 48th Annual Meeting of the Japan Wood Research Society, Shizuoka, April 1998; and 49th Annual Meeting of the Japan Wood Research Society, Tokyo, April 1999  相似文献   

3.
Gas chromatography — mass spectrometry analysis of the -glucosidase-treated MeOH extracts ofAnthriscus sylvestris showed, based on comparison of the mass spectra and retention times with those of authentic samples, the presence of lignans, yatein, secoisolariciresinol, lariciresinol, matairesinol, hinokinin, and pluviatolide. The existence of small amounts of bursehernin was suggested by mass chromatography. In addition, nemerosin and deoxypodophyllotoxin were tentatively identified by comparing the mass spectra with those reported in the literature. Enzyme preparations fromA. sylvestris catalyzed the formation of secoisolariciresinol and lariciresinol from coniferyl alcohol. Furthermore, the enzyme preparation catalyzed the formation of lariciresinol from (±)-pinoresinols and the formation of secoisolariciresinol from (±)-lariciresinols. Thus, pinoresinol/lariciresinol reductase (PLR) activity was detected. Chiral high-performance liquid chromatography analysis showed selective formation of (+)-lariciresinol and (–)-secoisolariciresinol from (±)pinoresinols with theA. sylvestris PLR preparation, indicating that the stereochemical property ofA. sylvestris PLR-catalyzed reduction was similar to those ofForsythia PLR andArctium lappa ripening seed PLR.Part of this report was presented at the 43rd Lignin Symposium, Fuchu, October 1998  相似文献   

4.
Secoisolariciresinol dehydrogenase activity was detected for the first time from Daphne odora and Daphne genkwa (Thymelaeaceae), which are known to produce optically pure (+)-matairesinol. In sharp contrast, (–)-matairesinol was formed selectively over the (+)-antipode by the secoisolariciresinol dehydrogenase preparation from both D. odora callus and D. genkwa shoots.  相似文献   

5.
Steps leading to the biosynthesis of syringyl lignans and tetrahydronaphthalene and naphthalene lignans, especially the formation of the C2–C7′ linkage, have not been elucidated. Lyoniresinol is a typical syringyl lignan, as well as a tetrahydronaphthalene lignan found in Lyonia ovalifolia var. elliptica. To demonstrate the biosynthetic pathway for (+)-lyoniresinol, three putative biosynthetic intermediates of lyoniresinol, syringaresinol, 5,5′-dimethoxylariciresinol, and 5,5′-dimethoxysecoisolariciresinol, were isolated from wood. The identity of the putative intermediates was confirmed by spectroscopic analyses, as well as by comparison of spectral and chromatographic data with those of authentic samples previously synthesized. The stereochemistry (enantiomeric composition and absolute configuration) of the isolated lignans were determined as (±)-syringaresinol, (8S,8′S)-(−)-5,5′-dimethoxylariciresinol [46% enantiomeric excess (e.e.)], (8S,8′S)-(+)-5,5′-dimethoxysecoisolariciresinol (91% e.e.), and (8R,8′R)-(+)-lyoniresinol (42% e.e.). The absolute configurations of (+)-and (-)-5,5′-dimethoxylariciresinols, and (+)-and (-)-5,5′-dimethoxysecoisolariciresinols were determined by their synthesis (catalytic reduction) from (8R,8′R)-(+)-and (8S,8′S)-(-)-syringaresinols and by subsequent chiral high-performance liquid chromatography analysis. This report was presented at the 55th Annual Meeting of the Japan Wood Research Society, Kyoto, March 2005  相似文献   

6.
Heartwood ofChamaecyparis obtusa contains significant amounts of a dibenzylbutyrolactone lignan, hinokinin (8). This investigation demonstrated that the contents of 8 and a norlignan, hinokiresinol (12), were higher in the heartwood region than in the sapwood, indicating their nature of being heartwood extractives. Eleven lignans — xanthoxylol (1), 7-oxohinokinin (2), savinin (3), dihydrosesamin (4), isoactifolin (5), sesamin (6), piperitol (7), hinokinin (8), pluviatolide (9), haplomyrfolin (10), and rnatairesinol (11) — were isolated from young shoots ofChamaecyparis obtusa cv. Breviramea. Eight lignans (1, 2, 4, 5, 7, 9,10, and11) were isolated from this plant for the first time. Chiral high-performance liquid Chromatographie analysis showed that8, 9, 10, and11, were found to be levorotatory and optically pure (>99% e.e.). Based on the chemical structures of the isolated lignans, possible biosynthetic pathways of8 are discussed.Parts of this report were presented at the 44th annual meeting of the Japan Wood Research Society, Nara, April 1994; the 46th annual meeting of the Japan Wood Research Society, Kumamoto, April 1996; and the 44th Lignin Symposium, Gifu, October 1999  相似文献   

7.
To clarify the biosynthetic pathway for syringyl lignans, especially syringyl tetrahydronaphthalene lignans and formation of the C2–C7′ linkage, production of (+)-lyoniresinol (LYR) and its predicted intermediates [syringaresinol (SYR), 5,5′-dimethoxylariciresinol (DMLR), and 5,5′-dimethoxysecoisolariciresinol (DMSLR)] in Lyonia ovalifolia var. elliptica was investigated by means of feeding experiments with radiolabeled precursors. Following individual administration of l-[U-14C]phenylalanine (Phe), [8-14C]sinapyl alcohol (SA), and [8,8′-14C]SYR to excised young shoots of L. ovalifolia and their subsequent metabolism, free [14C]lignans and [14C]lignan glycosides were extracted with methanol from stems and leaves and were divided into ethyl acetate-soluble fractions (lignans) and aqueous fractions (lignan glycosides), respectively. Using a combination of xylanase, cellulase, and β-glucosidase, the glycosides were hydrolyzed to liberate [14C]lignans as aglycones. l-[U-14C]Phe was incorporated into (+)-[14C]SYR [stem 0.38%, 8% enantiomeric excess (e.e.)], (−)-[14C]SYR (leaves 2.75%, 72% e.e.), (+)-[14C]DMLR (stem 0.07%, 18% e.e. and leaves 0.009%, 58% e.e.), (−)-[14C]DMSLR (stem 0.03%, 46% e.e. and leaves 0.05%, 20% e.e.), (+)-[14C]LYR (leaves 0.013%, 22% e.e.) and glycosides of (+)-[14C]LYR (stem 0.036%, 50% e.e.) in 24h. Based on the percent incorporation and enantiomeric composition of the lignans, the biosynthetic pathway of (8R,8′R)-(+)-LYR was proposed as follows: a nonselective dehydrogenative dimerization of sinapyl alcohol yields (±)-SYR, which is reduced with low specificity to give (8R,8′R)-(+)-DMLR. This is cyclized to directly give (+)-LYR as well as reduced again to (8R,8′R)-(−)-DMSLR. Although further transformation of (−)-DMSLR also leads to the formation of (+)-LYR, cyclization could be a main pathway for (+)-LYR biosynthesis. This report was presented at the IAWPS 2005 International Symposium on Wood Science and Technology, Yokohama, November 2005  相似文献   

8.
A new dibenzylbutyrolactone lignan 7.6-dihydroxybursehernin, together with six known lignans (pinoresinol, lariciresinol, secoisolariciresinol,-peltatin,-peltatin, 5-methoxypodophyllotoxin) were isolated from the methanol extracts ofLinum flavum var.compactum. The enantiomeric analysis of pinoresinol and lariciresinol isolated from the species, which are upstream lignans in the lignan biosynthetic pathway, indicated that they are not optically pure, which is in accordance with our recent findings on lignans occurring in other plant species.Parts of this report were presented at the 42nd Lignin Symposium, Sapporo, October 1997; and the 43rd Lignin Symposium, Fuchu, October 1998  相似文献   

9.
Serangium parcesetosum Sicard (Col., Coccinellidae) is considered one of the important predators of whiteflies. However, knowledge about its preferences for different prey stages, species and parasitized prey is still lacking in the literature. The present work investigated the preferences of S. parcesetosum for different stages of B. tabaci, different prey species and B. tabaci parasitized by Encarsia formosa Gahan (Hym., Aphelinidae) by prey consumption at different temperatures in the laboratory. Results showed that L2 and L4 predatory instars of S. parcesetosum preferred puparia to nymphs and eggs of Bemisia tabaci (Genn.) (Hom., Aleyrodidae). The mean daily prey consumption was 5.1–9.0, 4.5–6.2 and 3.6–4.3 by L2 and 6.4–9.7, 5.5–8.5 and 2.5–7.5 by L4 for puparia, nymphs and eggs, respectively. Adult females, however, indicated a significantly greater preference for both puparia and nymphs, consuming a daily mean of 6.4–7.5 puparia and 5.1–6.7 nymphs, but only 3.0–4.7 eggs. At 18 and 30 °C, all S. parcesetosum stages tested significantly preferred B. tabaci and Trialeurodes vaporariorum Westwood (Hom., Aleyrodidae) over the other three prey species offered. At both temperatures, all predatory stages preferred B. tabaci to T. vaporariorum, the L2 instar at 18 °C, showing significantly more preference for B. tabaci than T. vaporariorum. In contrast, very few individuals were consumed from Aphis gossypii Glover (Hom., Aphididae), Frankliniella occidentalis (Pergande) (Thys., Thripidae) and Tetranychus urticae Koch (Acari, Tetranychidae). At 18 °C, a daily mean of 7.5–8.0, 6.6–9.0 and 6.7–8.1 B. tabaci as well as 5.3–6.4, 5.4–7.8 and 5.6–6.3 T. vaporariorum was consumed by L2, L4 and adult females, respectively, while at 30 °C, L2, L4 and adult females consumed a mean of 9.3, 8.8–9.7 and 8.3–9.7 B. tabaci/day as well as 8.3–9.0, 7.8–9.1 and 5.5–8.4 T. vaporariorum/day, respectively. S. parcesetosum L2 and L4 instars as well as adult females and males at both studied temperatures showed a significant tendency to avoid B. tabaci puparia after 5 days of parasitism by E. formosa and preferred to feed on unparasitized whiteflies. At 18 °C, the mean daily consumption was 8.7 and 0.2 (L2), 11.1 and 0.6 (L4), 12.1 and 1.0 () as well as 10.5 and 0.2 (), while at 30 °C the means were 15.9 and 0.5 (L2), 19.8 and 1.0 (L4), 18.9 and 1.2 () as well as 17.4 and 0.6 () from unparasitized and parasitized B. tabaci puparia, respectively.This paper is gratefully dedicated to Prof. Dr. W Schwenke on his 83rd birthday, 22 March 2004  相似文献   

10.
Four compounds, including one new lignan cavaol H (1), one new coumarinolignoid 5′-hydroxycleomiscosin B (4) and two known lignans (23) were isolated from the 95% ethanol extract of the twigs of Eurycorymbus cavaleriei. Their structures were established on the basis of various spectroscopic analyses including 1D-(1H, 13C, and DEPT) and 2D-NMR (COSY, HMQC, and HMBC). The absolute stereochemistry of the two known lignans was firstly reported in this article by 1H NMR studies on Mosher's ester derivatives. In the present study, quinone reductase induction activities of compounds 14 were assayed, compound 4 showed moderate quinone reductase induction with concentration to double the enzyme activity (CD) of 10.5 ± 0.8 μg/mL. Then we established LC-MS-MS analysis of glutathione (GSH) incubation with compound 4 to explain whether compound 4 induced quinone reductase through alkylating of the sulfhydryl groups of Keap1. Reconstructed selected ion chromatogram (SIC) of m/z 706 after compound 4 incubation with GSH was different from that with Tris–HCl buffer solution, which meant the quinone reductase induction activity of compound 4 attributed to alkylating the sulfhydryl groups of Keap1.  相似文献   

11.
Five new steroids, colebrin A–E (15) were isolated from the aerial parts of Clerodendrum colebrookianum. The structures of the new compounds were elucidated on the basis of spectral evidence.  相似文献   

12.
The temporary association of annual crops in juvenile tree plantations (Taungya system) can reduce or offset the initial costs of reforestation and hence provide incentives for tree planting on private farms. A replicated systematic spacing design, derived from a Nelder-fan design, was used to study the effects of tree-crop distance on growth and development of the timber species salmwood (Cordia alliodora) or eucalyptus (Eucalyptus deglupta), associated with maize (Zea mays) or cassava (Manihot esculenta), during the first year after transplanting the trees on two sites on alluvial soils in the humid lowlands of Costa Rica. Association with maize did not affect mean tree growth. However, mean eucalyptus and salmwood heights of 7–8 m and 3–4 m, respectively, after one year in pure plantation or associated with maize, were only 4.7 m and 1.4 m, respectively, when associated with cassava. Wider tree – crop spacings were more important for initial salmwood growth than for eucalyptus. It was concluded that the shoot growth characteristics (continuous or episodical growth) of the timber species is a very important consideration when selecting associated agricultural crop species and tree-crop distances.  相似文献   

13.
To clarify the biosynthesis of syringyl lignans and lignan formation by stereoselective coupling of monolignols, formation of (+)-syringaresinol and (+)-pinoresinol inLiriodendron tulipifera were investigated by means of feeding experiments. Following individual administration ofl-[U-14C]phenylalanine and [8-14C]sinapyl alcohol to excised shoots ofL. tulipifera and their subsequent metabolism for 3h, free [14C] lignans and [14C] lignan glucosides were extracted from both of the stems and leaves with methanol and divided into an ether fraction and an aqueous one, respectively. The glucosides were hydrolyzed by a combination of cellulase and-glucosidase to liberate [14C]lignans as aglycones.l-[U-14C]Phenylalanine was incorporated into free (+)-[14C]syringaresinol and its glucosides; the (+)-[14C]syringaresinols in the stems and leaves had 52% enantiomeric excess (% e.e.) and 42% e.e., respectively; and the (+)-[14C]syringaresinol aglycones from the glucosides in the stems and leaves had 20% e.e. and 22% e.e., respectively. Furthermore, [8-14C]sinapyl alcohol was incorporated into (+)-[14C]syringaresinol and its glucosides in the stems. These results suggest that the (+)-enantiomer of syringaresinol was enantioselectively formed from two molecules of sinapyl alcohol inL. tulipifera followed by transformation into the (+)-syringaresinol glucosides, accompanying the formation of racemic syringaresinol by nonselective coupling and the subsequent transformation of the racemate into their glucosides.l-[U-14C]Phenylalanine was incorporated also into free (+)-[14C]pinoresinol and its glucosides with 12%–42% e.e.Part of this paper was presented at the 47th Annual Meeting of the Japan Wood Research Society, Kochi, April 1997  相似文献   

14.
A new flavone glycoside, identified as kaempferol 3-O-[3′″-acetyl-α- -arabinopyranosyl-(1′″–6″)]-β- -glucopyranoside (1), has been isolated from the aerial part of Thalictrum atriplex.  相似文献   

15.
Zusammenfassung Enddarmextrakte des Kleinen Buchdruckers (Ips amitinus) ergaben, daß die Männchen während der Aggregationsphase hauptsächlich (+)-Ipsdienol und Amitinol produzieren.Cis-Verbenol,trans-Verbenol, Myrtenol, Verbenon und (–)-Ipsenol werden nur in geringen Mengen freigesetzt. Das von den Weibchen produzierte 2-Methyl-3-buten-2-ol, das beim Großen Buchdrucker als Landestimulus dient, scheint ablenkend zu wirken.Freilanduntersuchungen mit den Enantiomeren von Ipsdienol, gemischt mit Amitinol, zeigten, daß die Mischung von (+)-Ipsdienol mit Amitinol für beide Geschlechter attraktiv ist. Das Racemat/Amitinol-Gemisch zeigt eine geringe Lockwirksamkeit, während die Kombination von (–)-Ipsdienol/Amitinol gar nicht attraktiv ist.
Racemate and enantiomeres of Ipsdienol for attractingIps amitinus (Eichh.) (Col., Scolytidae)
Hindgut extracts ofIps amitinus revealed that males of this polygamous bark beetle produce mainly (+)-Ips-dienol and Amitinol in the attraction phase.Cis- andtrans-Verbenol, Myrtenol, Verbenon and (–)Ipsenol are produced only in minor amounts. 2-Methyl-3-buten-2-ol is produced by females and seems to be inhibitive.Field experiments with different enantiomeric mixtures of Ipsdienol and Amitinol showed that the mixture (+)-Ipsdienol and Amitinol is attractive for both males and females. The mixture of racemic Ipsdienol and Amitinol seems to be less attractive; (–)-Ipsdienol and Amitinol is not attractive at all.


Mit 1 Abbildung  相似文献   

16.
During 7 years (1979–1985) cacao harvests (beans and husks) have been recorded for the agroforestry systems ofTheobroma cacao underCordia alliodora andErythrina poeppigiana shade trees. The mean oven dry cacao yields were 626 and 712 kg.ha–1.a–1 cocoa beans underC. alliodora andE. poeppigiana respectively. Harvests have gradually increased over the years and the plantation has now reached maturity.Annual extraction of N, P, K, Ca and Mg in fruits, which is relatively small, was calculated on the basis of chemical analyses. The following average values were found (kg.ha–1.a–1): At the age of 8 years, theC. alliodora trees have reached 26.7 cm diameter (DBH) and 14.0 m in height. Mean annual growth (from age 5 to 7) is 14.6 m3.ha–1.a–1.Natural plant residue production has been measured for 4 years (Nov. 1981–Oct. 1985). UnderE. poeppigiana it has reached a value of 8.91 t.ha–1.a–1 and underC. alliodora 7.07 t.ha–1.a–1. The shade trees have contributed 57 and 47% respectively. Transference and decomposition rates are high and important in the nutrient cycles.The nutrient content of the litter was analysed and corresponding average yearly transfers were (kg.ha–1.a–1): For part I see Vol. 4, No. 3, 1986.Agroforestry Project, CATIE/GTZ (Tropical Agricultural Research and Training Center/Gesselschaft für Technische Zusammenarbeit), Turrialba, Costa Rica  相似文献   

17.
Studies on the combined effects of beech–spruce mixtures are very rare. Hence, forest nutrition (soil, foliage) and nutrient fluxes via throughfall and soil solution were measured in adjacent stands of pure spruce, mixed spruce–beech and pure beech on three nutrient rich sites (Flysch) and three nutrient poor sites (Molasse) over a 2-year period. At low deposition rates (highest throughfall fluxes: 17 kg N ha−1 year−1 and 5 kg S ha−1 year−1) there was hardly any linkage between nutrient inputs and outputs. Element outputs were rather driven by internal N (mineralization, nitrification) and S (net mineralization of organic S compounds, desorption of historically deposited S) sources. Nitrate and sulfate seepage losses of spruce–beech mixtures were higher than expected from the corresponding single-species stands due to an unfavorable combination of spruce-similar soil solution concentrations coupled with beech-similar water fluxes on Flysch, while most processes on Molasse showed linear responses. Our data show that nutrient leaching through the soil is not simply a “wash through” but is mediated by a complex set of reactions within the plant–soil system.  相似文献   

18.
Fine root dynamics of shaded cacao plantations in Costa Rica   总被引:1,自引:0,他引:1  
Root turnover may contribute a significant proportion of recycled nutrients in agroforestry systems and competition between trees and crops for nutrients and water may depend on temporal fine root regrowth patterns. Fine root biomass ( 2 mm) and fine root productivity were measured during one year in plantations of cacao (Theobroma cacao) shaded by Erythrina poeppigiana or Cordia alliodora planted on a deep alluvial soil in Turrialba, Costa Rica. Fine root biomass of approximately 1.0 Mg ha–1 varied little during the year with maximum values at the beginning of the rainy season of 1.85 Mg ha–1 in the cacao-C. alliodora system compared to 1.20 Mg ha–1 for cacao-E. poeppigiana. Fine root productivity of C. alliodora and E. poeppigiana (maximum of 205 and 120 kg ha–1 4 week–1, respectively) was greatest at the end of the rainy season, while for cacao it was greatest at the beginning of the rainy season (34–68 kg ha–1 4 week–1), which suggests that if nutrient competition occurs between the shade trees and the cacao, it could be minimized by early fertilization during the beginning of the rains immediately after pruning the shade trees. Annual fine root turnover was close to 1.0 in both systems. Assuming that fine root biomass in these mature plantations was constant on an annual basis, nutrient inputs from fine root turnover were estimated as 23–24 (N), 2 (P), 14–16 (K), 7–11 (Ca) and 3–10 (Mg) kg ha–1 year–1, representing 6–13% and 3–6% of total nutrient input in organic matter in the C. alliodora and E. poeppigiana systems, respectively.  相似文献   

19.
Predictive models were developed for Cordia alliodora branch and Theobroma cacao branch or leaf biomass,based on branch basal areas (r2 0.79) but the model of C. alliodora leaf biomass, although significant, was of very low accuracy (r2 = 0.09) due to annual leaf fall. At age 10 years, shade tree stem biomass accounted for 80% of the total above-ground biomass of either tree. However, between the ages of 6 and 10 years, the biomass increment of T. cacao branches (3–4t.ha–1.a–1) was similar to that of the shade tree stems. During the same period, the net primary productivity was 35 and 28 t.ha–1.a–1, for the Erythrina poepigiana and and C. alliodora systems, respectively.Cocoa production under either of the shade trees C. alliodora or E. poeppigiana was 1000 kg.ha–1.a–1 (oven-dry; ages 6–10 yr). During the same period, C. alliodora timber production was 9 m3.ha–1.a–1 whilst the leguminous shade tree E. poeppigiana does not produce timber. Litterfall over the same 5 years, including crop and/or shade tree pruning residues, averages 11 and 23 t.ha–1.a–1, respectively. The main difference was due to E. poeppigiana pruning residues (10t.ha–1.a–1).Soil organic material reserves (0–45 cm) increased over 10 years from 198 to 240 t.ha–1 in the E. poeppigiana plots and from 168–184 t.ha–1 in the C. alliodora plots. These values, together with the productivity indices presented, provide evidence that the systems are sustainable.For economic reasons, the use of C. alliodora is recommended under the experimental conditions. however, on less fertile soils without fertilization, the greater biomass and hence nutrient return to the soil surface under E. poeppigiana, might make this the preferable shade tree.  相似文献   

20.
Agroforestry options as a means of promoting reforestation were testedby establishing with 10 farmers simple comparisons between pure plantations andtimber trees with annual or perennial intercrops. Two year-old intercroppedtrees on-farm had 22–48% greater height and 24–38% greater diameterthan trees in pure plantations. The exception was Cordiaalliodora that did not respond significantly to intercropping withcassava (Manihot esculenta). Only intercrops with the mostvaluable crops on agricultural soils produced a return to labour above thedailywage rate. On non-agricultural soils, farmers only intercrop a small area oftheir plantations with subsistence crops to meet home consumption needs. In thecontext of Costa Rica intercropping appeared to have a limited potential tofinance the reforestation costs of farmers.  相似文献   

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