Stereochemistry and biosynthesis of 8-O-4′ neolignans in Eucommia ulmoides: diastereoselective formation of guaiacylglycerol-8-O-4′-(sinapyl alcohol) ether     

Nattaya Lourith  Takeshi Katayama  Toshisada Suzuki 《Journal of Wood Science》2005,51(4):370-378

Stereochemistry and biosynthesis of guaiacylglycerol-8-O-4′-(sinapyl alcohol) ether (GGSE), an 8-O-4′ neolignan, which consists of coniferyl and sinapyl alcohol moieties, in Eucommia ulmoides were investigated. Four 8-O-4′ neolignans, GGSE, syringylglycerol-8-O-4′-(coniferyl alcohol) ether (SGCE), guaiacylglycerol-8-O-4′-(coniferyl alcohol) ether (GGCE), and syringylglycerol-8-O-4′-(sinapyl alcohol) ether (SGSE), were synthesized. Their erythro and threo diastereomers were separated through acetonide derivatives, intermediates of the synthesis, and identified by means of nuclear magnetic resonance (NMR) spectroscopy. All of the erythro-acetonide derivatives have larger coupling constants (ca 9 Hz) for the C₇-H resonances than those of the threo ones (1.5–2 Hz). In the case of the four 8-O-4′ neolignans, the C₇-H coupling constants of the threo-isomers are not smaller than those of the erythro ones. GGSE isolated previously from this plant was identified as the erythro isomer by comparison of the ¹³C-NMR data with synthetic erythro-GGSE and threo-GGSE and the other 8-O-4′ neolignans mentioned as above. Administration of a mixture of [8-¹⁴C]coniferyl alcohol and [8-¹⁴C]sinapyl alcohol to excised shoots of E. ulmoides was carried out and the incorporation of ¹⁴C into erythro-[¹⁴C]GGSE was found to be higher than that in threo-[¹⁴C]GGSE. The occurrence of diastereoselective formation of erythro-GGSE by cross coupling of coniferyl and sinapyl alcohols is suggested.Part of this paper was presented at the 47th Lignin Symposium, Fukuoka, October 2002 and the 53rd Annual Meeting of the Japan Wood Research Society, Fukuoka, April 2003  相似文献   

Lignin Characterization of Triploid Clones of Populus tomentosa Carr.   总被引：2，自引：0，他引：2  

Jin Xiao-juan Pu Jun-wen Xie Yi-min Takeshi Furuno Liu Xin-yu 《中国林学(英文版)》2005,7(2):52-56

In order to understand the structural characteristics of lignin in triploid clones ofPopulus tomentosa and its changes in the processes of pulping and bleaching, milled wood lignin （MWL）, lignin carbohydrate complex （LCC） and the residual lignin from kraft pulp （KP） and sulfite pulp （SP） were isolated and analyzed by Fourier transform infrared （FTIR） spectrum and ^13C nuclear magnetic resonance （NMR）. The most diagnostic peaks were assigned and the differences were discussed. The spectral patterns reveal that triploid P tomentosa shows the specific features of hardwood from temperate areas, but in the spectrum of FTIR, the strength ratio orAl270 cm^-1 to A1226 cm^-1 is 0.88, higher than the average of hardwood from temperate areas, which will make the lignin delignification more difficult during pulping and bleaching. The LCC from triploid P tomentosa is mainly composed of xyloglucan and glucuronic acid, and other glucides have much lower ratio. In LCC FTIR, there are three peaks at 1 427, 1 329 and 1 046 cm^-1, indicating that both semi-cellulose and cellulose could exist in LCC, and that there might be relationships between cellulose and lignin. Compared with the residual lignin from KP and SP, the condensed structure in KP is more than that in SP.  相似文献   

Absolute configuration of arylglycerol-β-aryl ethers obtained by asymmetric reduction of the correspondingα-ketonic compound with intactFusarium solani cells     

Takeshi Katayama  Jyoji Tsutsui  Kazuo Tsueda  Takao Miki  Yasuhiro Yamada  Murao Sogo 《Journal of Wood Science》2000,46(6):458-465

When (±)--oxo-guaiacylglycerol--(vanillic acid) ether (1) is degraded byFusarium solani M-13-1, the-ketone is initially reduced to giveerythro andthreo guaiacylglycerol--(vanillic acid) ethers (2), arylglycerol--aryl ethers, both of which are enantiomerically pure. The absolute configuration in each2 was determined by Mosher's method; the products were converted to,-di-(R)--methoxy--trifluoromethylphenylacetates (MTPA esters) (3) oferythro (-)- andthreo (+)-veratrylglycerol--(methyl vanillate) ethers (3), whose¹H nuclear magnetic resonance (NMR) spectra were examined and compared with those of four di-(R)-MTPA ester (3) diastereomers from chemically synthesizederythro (±)-3 andthreo (±)-3. To assign the- and-MTPA-OCH₃ peaks, the¹H NMR scans of several compounds that have substructures of 3 and their 3,4,5-trimethoxyphenyl analogues were examined. When a racemic alcohol reacts with (R)-MTPA to give a pair of (R)-MTPA ester diastereomers, the value was defined as the absolute value of the difference in the¹H chemical shifts of the peak between the diastereomers. It was found that the values of-MTPA-OCH₃ were larger than those of-MTPA-OCH₃ owing to a shielding effect of the veratryl ring located on the-MTPA-OCH₃, and that the-MTPA-OCH₃ peaks in the 3,4,5-trimethoxyphenyl compounds shifted downfield relative to those in the veratryl compounds. On the basis of the¹h NMR data of (R)-MTPA esters, the absolute configuration of the four chemically prepared diastereomers (3) were determined. The catabolicerythro 3 [fromerythro (-)-3] andthreo 3 [fromthreo (+)-3] were identical to (R, S, R)-erythro 3 and (R, S, S)- threo 3, respectively. An hydrogen species in the fungal reduction would attack the-ketone fromre-face of both (R)-1 and (S)-1, givingerythro (S, R)-2 andthreo (S, S)-2, respectively.Part of this paper was presented at the 33rd Lignin Symposium, Tsukuba, November 1988  相似文献   

农田防护林主带间距离的确定——基于林带结构与风速降低的关系(英文)     

朱教君  姜凤岐  松崎健 《林业研究》2002,(2)

本文通过对9条分布均匀、相对较窄的不同疏透度(透光疏透度,下同)(0.13～0.33)的树木林带和不同疏透度(0.00～0.80)风障组合的野外风速观测,确定了树木林带和风障的最适疏透度分别为0.25和0.13。基于林带结构(疏透度)与风速降低的关系,确定了林带主带间距离的主要参数,即,林带结构系数(δ)和以主害风为代表的小气候参数(Lrp)。另外,通过对林带树木的野外调查,应用树木解析技术确定林带成林高(H0)。因此,树木林带的主带间距可以通过林带结构系数、希望降低风速的比例和树木生长模型来确定。本文以杨树林带为例,具体确定了杨树林带的主带间距。该研究结果不仅适于树木林带的设计,同时适于其它生物材料或人工风障的设计。图4表5参40。  相似文献   

Spacing interval between principal tree windbreaks--Based on the relationship between windbreak structure and wind reduction     

ZHU Jiao-Jun  JIANG Feng-qi  MATSUZAKI Takeshi 《林业研究》2002,13(2)

Relative windspeed reduction was measured behind nine relatively narrow, homogenous tree windbreaks with porosities between 0.13-0.33, and behind 28 combinations of model stubble barriers representing 25 different optical porosities (0.00-0.80). The optimum porosities observed were 0.25 and 0.13 for tree windbreaks and stubble barriers respectively. Based on the relationship between windbreak structure (optical porosity) and wind reduction, the chief indices for determining spacing interval, i.e., the windbreak structure index (δ) and the parameter of microclimate, represented by the problem wind (Lrp), were determined. Additionally, investigations on shelterbelt trees were carried out, and stem-analysis techniques were used, to develop a method for determining the mature height of tree windbreaks (H0). Optimal spacing intervals between windbreaks could be predicted from the indices of a given windbreak structure, percentage of reduction of windspeed desired and tree growth model. A hypothetical example for determining the spacing interval of principal poplar windbreaks is given at the end of this paper. The results can be applied not only to tree windbreak design but also to other plant materials and artificial barriers for wind protection.  相似文献   

The effects of within-species and between-species variation in wood density on the photodegradation depth profiles of sugi (Cryptomeria japonica) and hinoki (Chamaecyparis obtusa)     

Yutaka Kataoka  Makoto Kiguchi  Takeshi Fujiwara  Philip D. Evans 《Journal of Wood Science》2005,51(5):531-536

Low density wood is more rapidly eroded than denser wood when exposed to the weather, possibly because it is more susceptible to photodegradation. Fourier transform infrared microscopy was used to examine: (1) the depth of photodegradation in earlywood and latewood of sugi (Japanese cedar) and earlywood of hinoki (Japanese cypress) exposed for up to 1500 h to artificial sunlight emitted by a xenon lamp (375 W/m² within the 300 to 700 nm spectral range); and (2) the relationship between the density of wood tissues and depth of photodegradation. The depth of photodegradation varied between species (sugi and hinoki) as well as within a growth ring (sugi earlywood and latewood), and there was an inversely proportional relationship between depth of photodegradation and wood density. These findings may explain why low density earlywood is more rapidly eroded than latewood during weathering, and more generally, why there is an inverse relationship between the density of wood species and their rate of erosion during artificial and natural weathering. Part of this work was presented at the 54th Annual Meeting of the Japan Wood Research Society, Sapporo, August 2004  相似文献   

Nickel-catalyzed carbonization of wood for coproduction of functional carbon and fluid fuels I: production of crystallized mesoporous carbon     

Tsutomu Suzuki  Kyoko Suzuki  Yukio Takahashi  Mitsuhiro Okimoto  Tetsuo Yamada  Noriyasu Okazaki  Yuichi Shimizu  Masashi Fujiwara 《Journal of Wood Science》2007,53(1):54-60

Japanese larch wood loaded with nickel (1%–4%) alone or with nickel and calcium (0.25%–1.5%) was carbonized at 800°–900°C for 0–120min with a heating rate of 5°–20°C min⁻¹ in a helium flow of 5.8−46.4 ml STP cm⁻² min⁻¹ to examine the influence of these variables on the crystallization of carbon (the formation of T component) and the development of mesoporosity. From the obtained results, reaction conditions suitable for effective production of carbon with the dual functions of adequate electroconductivity and adsorption capacity in liquid phase were established, thereby explaining the factors that govern the process. It was also confirmed that mesopore having a diameter of about 4 nm was selectively produced at the cost of specific (BET) surface area in parallel with the formation of T component. This result provided good insight into how the simultaneous dual function could be realized.  相似文献   

Fire protection of a laminated veneer lumber joint by wood carbon phenolic spheres sheeting     

Subyakto  Toshimitsu?Hata  Isamu?Ide  Takeshi?Yamane  Shuichi?KawaiEmail author 《Journal of Wood Science》2004,50(2):157-161

Laminated veneer lumber joints made with metal plate connectors were protected with wood carbon phenolic spheres (CPS) sheeting and tested for creep under fire. The effects of the carbonizing temperature of charcoal, used as raw material for the CPS sheets, the thickness, and the location of the sheet on the joint regarding the fire-resistance performance of the joint were studied. The time to rupture of the joints covered with CPS sheets made from charcoal carbonized at 800°C (CPS800) was slightly prolonged compared with that of uncovered joints. On the other hand, the time to rupture of CPS sheets made from charcoal carbonized at 1600°C (CPS1600) was markedly extended. The changes in the charcoal properties due to increasing the carbonizing temperature might be the main reason the CPS1600 sheets had higher fire-resistance performance. The thickness and location of CPS1600 sheets have significant effects on the fire resistance of the joint. A highly fire-resistant laminated veneer lumber joint was obtained using a CPS1600 sheet. The CPS1600 sheet with a thickness of 3mm covering three sides of the joint prolonged the time to rupture 16-fold compared with that of unprotected joints.Part of this paper was presented at the 4th International Wood Science Symposium, Serpong, Indonesia, September 2002  相似文献   

Synthesis of 1-hydroxyethyl-2-alkyl-2-imidazoline and its derivative sulfonate amphoteric surfactant from tall oil fatty acid     

Shi-Fa Wang  Zhi Cheng  Takeshi Furuno 《Journal of Wood Science》2003,49(4):371-376

1-Hydroxyethyl-2-alkyl-2-imidazoline (HEAI) and its derivative sulfonate amphoteric surfactant were synthesized using tall oil fatty acid as the raw material. Suitable experimental conditions for synthesizing the intermediate and final products were probed. Their chemical structures were also investigated by means of infrared spectroscopy and hydrogen nuclear magnetic resonance spectroscopy. Based on the results of these analyses, it has been found that during the reaction process of HEAI with sodium 3-chloro-2-hydroxypropane sulfonate under alkaline condition the imidazoline ring was hydrolyzed to amides, and the obtained amphoteric surfactant was actually a complex mixture of amides. An etherification reaction in the hydroxyethyl group was also observed when the HEAI/sodium 3-chloro-2-hydroxypropane sulfonate molar ratio was more than 1:1.  相似文献   

Effect of bamboo vinegar on regulation of germination and radicle growth of seed plants   总被引：10，自引：0，他引：10  

Jun Mu  Tohru Uehara  Takeshi Furuno 《Journal of Wood Science》2003,49(3):262-270

 Two kinds of bamboo vinegar from madake bamboo (Phyllostachys bambusoides) and moso bamboo (Phyllostachys pubescens) were prepared to analyze their components by gas chromatography (GC). The original vinegar, distilled vinegar, ether-extracted vinegar, and three fractions including acidic, neutral, and phenolic fractions separated from ether-extracted vinegar were diluted with distilled water 10² to 10⁷ times. These diluted vinegar solutions were used to investigate the effect of bamboo vinegar on the germination and radicle growth of seed plants. High concentrations of all kinds of treated bamboo vinegars (e.g., 10² of original vinegar and 10³ of ether-extracted vinegar) showed strong inhibition against germination of the seeds. However, an appropriate dilution of bamboo vinegar showed an obvious promotional effect on germination and radicle growth for the four kinds of tested seeds (lettuce, watercress, honewort, chrysanthemum). Received: December, 12, 2001 / Accepted: July 29, 2002 RID="*" ID="*" Part of this paper was presented at the 51st Annual Meeting of the Japan Wood Research Society, Tokyo, April 2001  相似文献