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Content and distribution of lignans in Taiwania cryptomerioides Hayata

  • Nai-Wen Tsao , Ying-Hsuan Sun , Shih-Chang Chien , Fang-Hua Chu , Shang-Tzen Chang , Yueh-Hsiung Kuo and Sheng-Yang Wang EMAIL logo
Published/Copyright: December 17, 2015
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Abstract

Taiwania (Taiwania cryptomerioides Hayata) is one of the economically important tree species indigenous to Taiwan. Hundreds of secondary metabolites have been identified from its wood, bark, root, and needles with lignans as the dominant ones. This substance group contributes a lot to the color, durability, and bioactivities of Taiwaniana. The present paper is dedicated to the quantification of radial and longitudinal lignan distribution. The extractives begin to accumulate largely in the transition zone (TZ), and reach a maximum after finishing the heartwood (hW) formation. Both dibenzyl-γ-butyrolactone type and arylnaphthalide type lignans were found in sapwood (sW) except for the compound taiwanin A. Clearly, the heartwood formation of Taiwania differs from the hitherto known hW formation types and it is suggested to be denominated as Taiwania-type hW formation, where the biosynthesis of extractives begins in the sW and where their accumulation is clearly elevated in the TZ. A generalized biosynthesis scheme of Taiwanin is presented showing the putative relationships among the most important dimeric lignans that lead to the formation of taiwanin type lignans.


Corresponding author: Sheng-Yang Wang, Department of Forestry, National Chung-Hsing University, Taichung 402, Taiwan, Phone: +886-4-22840345, ext-138, e-mail: ; Agricultural Biotechnology Center, National Chung-Hsing University, Taichung, Taiwan; and Agricultural Biotechnology Research Center, Academia Sinica, Taipei, Taiwan

Acknowledgments

This study was supported by the Ministry of Science and Technology, Taiwan, (NSC-103-2321-B-005-021) and the Ministry of Education, Taiwan, R.O.C. under the ATU plan.

References

Adlercreutz, H. (2007) Lignans and human health. Crit. Rev. Clin. Lab. Sci. 44:483–525.10.1080/10408360701612942Search in Google Scholar

Burtin, P., Jay-Allemand, C., Charpentier, J.P., Janin, G. (1998) Natural wood colouring process in Juglans sp. (J. nigra, J. regia and hybrid J. nigra 23 × J.regia) depends on native phenolic compounds accumulated in the transition zone between sapwood and heartwood. Trees 12:258–264.10.1007/PL00009716Search in Google Scholar

Chang, S.T., Wang, S.Y., Wu, Y.C. (1998) Retention of red color in Taiwania (Taiwania cryptomerioides Hayata) heartwood. Holzforschung 52:13–17.10.1515/hfsg.1998.52.1.13Search in Google Scholar

Chang, S.T., Wang, S.Y., Su, Y.C., Huang, S.L., Kuo, Y.H. (1999a) Chemical constituents and mechanisms of discoloration of Taiwania (Taiwania cryptomerioides Hayata) heartwood. I The structure reconfirmation and conversion mechanism of taiwanin A. Holzforschung 53:142–146.10.1515/HF.1999.023Search in Google Scholar

Chang, S.T., Wang, S.Y., Wu, C.L., Su, Y.C., Kuo, Y.-H. (1999b) Antifungal compounds in the ethyl acetate soluble fraction of the extractives of Taiwania (Taiwan cryptomerioides Hayata) heartwood. Holzforschung 53:487–490.10.1515/HF.1999.080Search in Google Scholar

Chang, S.T., Wang, S.Y., Wu, C.L., Chen, P.F., Kuo, Y.H. (2000a) Comparison of the antifungal activity of cadinane skeletal sesquiterpenoids from Taiwania (Taiwania cryptomerioides Hayata) heartwood. Holzforschung 54:241–245.10.1515/HF.2000.041Search in Google Scholar

Chang, S.T., Chen, P.F., Chang, S.C. (2000b) Antibacterial activity of essential oils and extractives from Taiwania (Taiwania cryptomerioides Hayata). Q. J. Chin. For. 33:123–129. (in Chinese with English abstract).Search in Google Scholar

Chang, S.T., Wang, D.S.Y., Wu, C.L., Shiah, S.G., Kuo, Y.H., Chang, C.J. (2000c) Cytotoxicity of extractives from Taiwania cryptomerioides heartwood. Phytochem. 55:227–232.10.1016/S0031-9422(00)00275-2Search in Google Scholar

Chang, S.T., Cheng, S.S., Wang S.Y. (2001a) Antitermitic activity of essential oils and components from Taiwania (Taiwania cryptomerioides). J. Chem. Ecol. 27:717–724.10.1023/A:1010397801826Search in Google Scholar

Chang, S.T., Chen, P.F., Wang S.Y., Wu H.H. (2001b) Antitermite activity of essential oils and their constituents from Taiwania cryptomerioides. J. Med. Entomol. 38:455–457.10.1603/0022-2585-38.3.455Search in Google Scholar PubMed

Chang, S.T., Wang, S.Y., Kuo, Y.H. (2003) Resources and bioactive substances from Taiwania (Taiwania cryptomerioides). J. Wood Sci. 49:1–4.10.1007/s100860300000Search in Google Scholar

Chien, S.C., Kuo, Y.H. (2009) Review of chemical constituents of Taiwania cryptomerioides. Chemistry 67:33–44. (In Chinese with English abstract).Search in Google Scholar

Christenhusz, M.J.M., Reveal, J.L., Farjon, A., Gardner, M.F., Mill, R.R., Chase, M.W. (2011) A new classification and linear sequence of extant gymnosperms. Phytotaxa 19:55–70.10.11646/phytotaxa.19.1.3Search in Google Scholar

Dellus, V., Mila, I., Scalbert, A., Menard, C., Michon, V., Herve du Penhoat, C.L.M. (1997) Douglas-fir polyphenols and heartwood formation. Phytochem. 45:1573–1578.10.1016/S0031-9422(97)00245-8Search in Google Scholar

Duenisch, O., Richter, H.G., Koch, G. (2010) Wood properties of juvenile and mature heartwood in Robinia pseudoacacia L. Wood Sci. Techn. 44:301–313.10.1007/s00226-009-0275-0Search in Google Scholar

Farjon, A. World Checklist and Bibliography of Conifers, 2nd edn. The Royal Botanic Gardens Press, England, 2001. p. 97.Search in Google Scholar

Hashida, K., Tabata, M., Kuroda, K., Otsuka, Y., Kubo, S., Makino, R., Kubojima, Y., Tonosaki, M., Ohara, S. (2014) Phenolic extractives in the trunk of Toxicodendron vernicifluum: chemical characteristics, contents and radial distribution. J. Wood Sci. 60:160–168.10.1007/s10086-013-1385-8Search in Google Scholar

Hayata, B. (1906) On Taiwania, a new genus of coniferae from the island of Formosa. Bot. J. Linn. Soc. 37:330–331.10.1111/j.1095-8339.1906.tb00842.xSearch in Google Scholar

Kampe, A., Magel, E. (2013) New insights into heartwood and heartwood formation. In: Cellular Aspects of Wood Formation. Eds. Jorg, F. Springer, Heidelberg, pp. 71–88.10.1007/978-3-642-36491-4_3Search in Google Scholar

Mayer, I., Koch, G., Puls, J. (2006) Topochemical investigations of wood extractives and their influence on colour changes in American black cherry (Prunus serotine Borkh.). Holzforschung 60:589–594.10.1515/HF.2006.100Search in Google Scholar

Saito, K., Mitsutani, T., Imai, T., Matsushita, Y., Fukushima, K. (2008) Discriminating the Indistingushable Sapwood from Heartwood in Discolored Ancient Wood by Direct Molecular Mapping of Specific Extractives Using Time-of-Flight Secondary Ion Mass Spectrometry. Anal. Chem. 80:1552–1557.10.1021/ac7021162Search in Google Scholar PubMed

Su, Y.C., Chang, S.T., Wang, S.Y., Wu, C.L., Huang, S.L., Kuo, Y.H. (1998) Structure elucidation of three lignans isolated from Taiwania (Taiwania cryptomerioides Hayata) heartwood: savinin, taiwanin C, and dimethylmatiresinol. Quarterly J. Chinese Forestry 31:287–295.Search in Google Scholar

Takaku, N., Choi, D.H., Mikame, K., Okunishi, T., Suzuki, S., Ohashi, H., Umezawa, T., Shimada, M. (2001) Lignans of Chamaecyparis obtuse. J. Wood Sci. 47:476–482.10.1007/BF00767901Search in Google Scholar

Thompson, A., Cooper J., Ingram Jr., L.L. (2006) Distribution of terpenes in heartwood and sapwood of loblolly pine. For. Prod. J. 56:46–48.Search in Google Scholar

Walther, H. (1999) Die Tertiaerflora von Kleinsaubernitz bei Bautzen. Palaeontographica B 249:63–174.10.1127/palb/249/1999/63Search in Google Scholar

Willför, S.M., Smeds, A.I., Holmbom, B.R. (2006) Chromatographic analysis of lignans. J. Chrom. A1112:64–77.10.1016/j.chroma.2005.11.054Search in Google Scholar PubMed

Wang, S.Y., Chang, S.T., Wu, C.L., Su, Y.C., Huang, S.L., Kuo, Y.H. (1998) Three chemical constituents contributing to the color of Taiwania (Taiwania cryptomerioides Hayata) heartwood: hinokinin, helioxanthin, and pluviatolide. Quarterly J. Chinese Forestry 31:187–193.Search in Google Scholar

Wang, S.Y., Wu, J.H., Shyur, L.F., Kuo, Y.H., Chang, S.T. (2002) Antioxidant activity of abietane-type diterpenes from heartwood of Taiwania cryptomerioides Hayata. Holzforschung 56:487–292.10.1515/HF.2002.075Search in Google Scholar

Received: 2015-7-7
Accepted: 2015-10-7
Published Online: 2015-12-17
Published in Print: 2016-6-1

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