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Lignin Characteristics of Peculiar Vascular Plants

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Lignin Characteristics of Peculiar Vascular Plants J Wood Sci (2007) 53:520–523 © The Japan Wood Research Society 2007 DOI 10.1007/s10086-007-0891-y NOTE Zhenfu Jin · Shunliu Shao · Kyoko S. Katsumata Kenji Iiyama Lignin characteristics of peculiar vascular plants Received: October 2, 2006 / Accepted: February 21, 2007 / Published online: May 31, 2007 Abstract Trochodendron aralioides Sieb. et Zucc. and in guaiacyl lignin and guaiacyl–syringyl lignin do not exactly Chloranthus glaber (Thunb.) Makino [Sarcandra globra refl ect taxonomical differences, as reported in previous arti- (Thunb.) Nakai] belong to primitive angiosperms, and are cles. It was found that guaiacyl–syringyl lignin is not neces- characterized by the absence of vessels. Ephedra sinica Stapf, sarily linked to the presence of vessels. which is classifi ed in the gymnosperms, contains vessel ele- ments and fi ber together with tracheids. Podocarpus macro- Key words Primitive vascular plants · Tracheids · Vessels · phyllus (Thunb. Ex Murray) D. Don var. macrophyllus is Lignin characteristics reported to give a weak positive Mäule test, although it is classifi ed as a gymnosperm. Podocarpus macrophyllus gave only vanillin on alkaline nitrobenzene oxidation, while E. si- nica, T. aralioides, and C. glaber gave both vanillin and syrin- Introduction galdehyde. The molar ratio of syringyl to guaiacyl nuclei (S/V ratio) of C. glaber was signifi cantly low (S/V = Lignin is a substance unique to vascular plants, and it is well 0.08) in comparison with the value for T. aralioides (S/V = recognized that the evolution of lignin deposition is closely 1.56). The erythro form is the predominant diasteromeric associated with vascular plant evolution.1,2 In general, the form of b-O-4 intermonomer linkages of T. aralioides and E. vascular systems of primitive vascular plants such as pteri- sinica [molar ratio of erythro to threo forms (E/T ratio): 1.93 dophytes and gymnosperms are composed of tracheids, and 1.67, respectively]; however, P. macrophyllus and C. gla- whereas that of angiosperm is composed of vessels. In par- ber lignins, of which S/V ratios were 0 and 0.08, gave approxi- allel with the differences of the vascular systems, the lignin mately equal amounts of erythro and threo forms (E/T ratio: of pteridophytes and gymnosperms gives vanillin as a major 1.01 and 1.14). Results from 1H NMR spectroscopy agree product by alkaline nitrobenzene oxidation, whereas vanil- well with S/V ratios of alkaline nitrobenzene oxidation and lin and syringaldehyde are obtained from angiosperm lig- E/T ratios of ozonation products. In conclusion, differences nin.3,4 However, some species of Selaginella and Gnetales, which belong to the pteridophytes and gymnosperms, respectively, contain vessel elements, and have been Z. Jin found to give not only vanillin but also high yields of syrin- School of Engineering, Zhejiang Forestry University, Zhejiang 3–7 galdehyde. Species of Magnoliaceae, Winteraceae, and 311300, China Trochodendraceae, all of which are classifi ed as primitive S. Shao angiosperms, are characterized by the absence of vessels Institute of Ecology, Zhejiang Forestry Academy, Zhejiang 310023, China and the yield of syringaldehyde was relatively low in com- parison with typical angiosperms.3 K.S. Katsumata Graduate School of Agricultural and Life Science, the University of Trochodendron aralioides and Chloranthus glaber Tokyo, Tokyo 113-8657, Japan (Thunb.) Makino [Sarcandra globra (Thunb.) Nakai] (local K. Iiyama1 (*) name: senryou) belong to the primitive angiosperms, and Asian Natural Environmental Science Center, the University of are characterized by the absence of vessels. Ephedra sinica, Tokyo, Tokyo 113-0033, Japan which is classifi ed in Ephedrales of gymnospermae, contains vessel elements and fi ber together with tracheids. Ephedra 3,8 Present address: sinica gave a positive color to the Mäule test. Podocarpus 1 Japan International Research Center for Agricultural Sciences, macrophyllus was reported to give a very weak positive re- 1-1 Ohwashi, Tsukuba 305-8686, Japan 3,8 Tel. +81-29-838-6301; Fax +81-29-838-6316 sult to the Mäule test, although it belongs to Podocar- e-mail: [email protected] paceae of gymnospermae. 521 In this study, T. aralioides, C. glaber, E. sinica, and The aromatic composition of lignin of the extract-free P. macrophyllus were subjected to alkaline nitrobenzene samples was examined by an alkaline nitrobenzene oxida- oxidation for aromatic composition of lignin and ozonation tion.12 The reaction products were trimethylsilylated with to investigate intermonomer linkages and their diastereo- N,O-bis(trimethylsilyl)acetamide (BSA). The products meric structure of lignin of these peculiar plant species. were analyzed by a Shimadzu GC-17A gas chromatograph Björkman lignins were isolated and structural characteris- using a capillary column (NB1; 25 m × 0.25 mm i.d.) equipped tics were analyzed by 1H nuclear magnetic resonance with a fl ame ionization detector (FID). Both injector and (NMR) spectroscopy. detector temperatures were 280°C. The column tempera- ture was kept at 150°C for 10 min, and was programmed to rise at 5°C min−1 to 250°C. Ethyl vanillin was used as an in- ternal standard. Materials and methods Ozonation analysis was carried out according to the scheme of Akiyama et al.13 for the extract-free samples. The Samples ozonation products were trimethylsilylated with hexameth- yldisilazane and trimethylchlorosilane for 30 min at 60°C in Trochodendron aralioides and Chloranthus glaber were col- dimethylsulfoxide, then analyzed by a Shimadzu GC-17A lected from the University Forest at Chichibu of the Uni- gas chromatograph using an NB1 capillary column (25 m × versity of Tokyo and a private garden at Ichikawa, Chiba 0.25 mm i.d.) equipped with FID. Both injector and detector Prefecture, respectively. Podocarpus macrophyllus was har- temperatures were 280°C. The column temperature was vested from the University Forest at Chiba. Ephedra sinica kept at 120°C for 5 min, and was programmed to increase was purchased (Hyakka-en Chinese Pharmacy, Osaka, at 4°C min−1 to 170°C and then by 10°C min−1 to 280°C. Japan). After being freeze-dried, samples were ground in a Erythritol was used as an internal standard. Wiley mill to pass a 420-mm sieve. The ground samples ex- cept E. sinica were extracted with ethanol–benzene (1 : 2, v/v) using a Soxhlet extractor; E. sinica was extracted with Spectroscopy analyses boiling 80% (v/v) ethanol for 1 h (three times), then with hot water overnight at 40°C with shaking. The extract-free The Björkman lignin was acetylated with acetic anhydride samples were further ground using a vibratory ball mill with a catalytic amount of pyridine overnight at room tem- perature with stirring. The acetylated sample was dissolved MM200 (Retsch, Germany) for 15 min at a vibration rate of 1 30 s−1 to use in chemical analyses. in chloroform-d and the H NMR spectrum was recorded using a Jeol JNM-A 500 NMR spectrometer (Jeol, Japan). Preparation of Björkman lignin Results and discussion The extract-free sample was dried in a vacuum oven over- night at 40°C, and then was fi nely ground with a vibratory Podocarpus macrophyllus and Ephedra sinica belong to the ball mill VS-2 (Irie Shokai, Tokyo, Japan) for 72 h with gymnosperms, and Trochodendron aralioides and Chloran- cooling by tap water fl ow. Dispersing solvent was not used 9 thus glaber are classifi ed in the angiosperms. Lignin con- during milling. Björkman lignin was extracted from the tents of P. macrophyllus and E. sinica were higher than fi nely ground sample with dioxane–water (9 : 1, v/v) and 10 those of T. aralioides and C. glaber (Table 1) and the result purifi ed according to the procedure of Björkman. The was in agreement with general accepted fact that gymno- yields of purifi ed Björkman lignins isolated from T. aralioi- sperms give higher lignin content than angiosperms.14,15 des, C. glaber, P. macrophyllus, and E. sinica were 34.6%, Acid-soluble lignin contents of T. aralioides and C. glaber 36.2%, 29.8%, and 19.5% (w/w), respectively. were 2.3% and 0.9%, respectively. The acid-soluble lignin formed during Klason lignin preparation is signifi cantly dif- 14 Chemical analyses ferent among wood species. Podocarpus macrophyllus gave only vanillin on alkaline Lignin content of the extract-free ground sample was deter- nitrobenzene oxidation, while E. sinica, T. aralioides, and mined according to the Klason procedure (Tappi Standard C. glaber gave both vanillin and syringaldehyde (Table 1). T222 om-88) with minor modifi cations. The sample was Podocarpus macrophyllus was found to give a very weak 3,8 treated with 72% (w/w) H2SO4 for 3 h at room temperature. positive Mäule test, while syringaldehyde could not be 3 The reaction mixture was diluted with water to 3% (w/w) detected. On the other hand, E. sinica gave a strong posi- 3,8 concentration of H2SO4, and then digested at 121°C for tive Mäule test, and the molar ratio of syringaldehyde 30 min. After cooling, the insoluble fraction (Klason lignin) to vanillin (S/V) was 1.04. The lignin content of E. sinica was separated by fi ltration using a glass fi lter (G4). Klason was 36.2%, while the total yield of aldehydes and acids lignin was measured gravimetrically after drying overnight from alkaline nitrobenzene oxidation was as low as −1 at 105°C. Acid-soluble lignin was calculated by measuring 79.4 mmol · (200 g lignin) . These results suggest that the UV absorption at 205 nm and using a known extinction Klason residue of E. sinica would be expected to contain coeffi cient of 110 l · g−1 · cm−1.11 substances other than lignin, such as proteins, lipids as com- 522 Table 1.
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