Antitermitic activities of abietane-type diterpenes from Taxodium distichum cones

Journal of Chemical Ecology

Volumn 35, Issue 6, 2009, Pages 635-642

  Kusumoto, Norihisa ^a   Ashitani, Tatsuya ^a,b   Hayasaka, Yuichi ^b   Murayama, Tetsuya ^a,b   Ogiyama, Koichi ^b   Takahashi, Koetsu ^a,b  

^a IWATE UNIVERSITY   (Japan)

^b YAMAGATA UNIVERSITY   (Japan)

Author keywords

Abietane; Antitermite; Bioactivity; Cone; Diterpene; Oxidation; Reticulitermes speratus; Taxodiaceae; Taxodium distichum

Indexed keywords

ACIDITY; BIOACTIVITY; CONIFEROUS TREE; DATA ACQUISITION; HYDROCARBON; NUCLEAR MAGNETIC RESONANCE; OXIDATION; SPECTRAL ANALYSIS; TERMITE;

CONIFEROPHYTA; CUPRESSACEAE; ISOPTERA; RETICULITERMES SPERATUS; RHINOTERMITIDAE; TAXODIUM; TAXODIUM DISTICHUM;

ABIETANE DERIVATIVE; INSECTICIDE;

ANIMAL; ARTICLE; CHEMISTRY; GROWTH, DEVELOPMENT AND AGING; ISOPTERA; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TAXODIUM;

ANIMALS; DITERPENES, ABIETANE; INSECTICIDES; ISOPTERA; MAGNETIC RESONANCE SPECTROSCOPY; TAXODIUM;

EID: 70349237616     PISSN: 00980331     EISSN: 15731561     Source Type: Journal    
DOI: 10.1007/s10886-009-9646-0     Document Type: Article

References (39)

1. Ashitani, T., Ujike, M., Nagahama, S., Ueno, T., and Sakai, K. 2001. Characterization of Sugi (Cryptomeria japonica) bark extracts. Mokuzai Gakkaishi 47:276-281.
2. Bläske, V. U. and Hertel, H. 2001. Repellent and toxic effects of plant extracts on subterranean termite (Isoptera: Rhinotermitidae). J. Econ. Entomol. 94:1200-1208.
3. Bultman, J. D., Beal, R. H., and Ampong, F. F. K. 1979. Natural resistance of some tropical African woods to Coptotermes formosanus Shiraki. Forest Prod. J. 29:46-51.
4. Cornelius, M. L., Grace, J. K., and Yates, J. R. III 1997. Toxicity of monoterpenoids and other natural products to the formosan subterranean termite (Isoptera: Rhinotermitidae). J. Econ. Entomol. 90:320-325.
5. Enoki, A., Takahama, S., and Kitao, K. 1977. The Extractives of Metasequoia, Metasequoia glyptostroboides Hu et Cheng. The isolation of Metasequirin-A, Athrotaxin and Agatharesinol from the heartwood. Mokuzai Gakkaishi 23:579-586.
6. Fukumoto, H., Morimoto, M., Fukuda, Y., Kitayama, T., and Komai, K. 2007. Antifeedants in tropical asian species, resak, against a subterranean termite, Reticulitermes speratus (Kolbe). Bull. Fac. Agrc. Kinki Univ. 40:31-38.
7. Ganapaty, S., Thomas, P. S., Fotso, S., and Laatsch, H. 2004. Antitermitic quinones from Diospyros sylvatica. Phytochemistry 65:1265-1271.
8. Gao, J. and Han, G. 1997. Cytotoxic abietane diterpenoids from Caryopteris incana. Phytochemistry 44:759-761.
9. Gigante, B., Santos, C., Silva, A. M., Curto, M. J. M., Nascimento, M. S. J., Pinto, E., Pedro, M., Cerqueira, F., Pinto, M. M., Duarte, M. P., Laires, A., Rueff, J., Gonçalves, J., Pegado, M. I., and Valdeira, M. L. 2003. Catechols from abietic acid: synthesis and evaluation as bioactive compounds. Bioorg. Med. Chem. 11:1631-1638.
10. Hensch, M., Rüedi, P., and Eugster, C. H. 1975. Horminon, Taxochinon und weitere Royleanone aus 2 abessinischen Plectranthus-Spezies (Labiatae). Helv. Chim. Acta 58:1921-1934.
11. Hirasawa, Y., Izawa, E., Matsuno, Y., Kawahara, N., Goda, Y., and Morita, H. 2007. Taxodistines A and B, abietane-type diterpenes from Taxodium distichum. Bioorg. Med. Chem. Lett. 17:5868-5871.
12. Hueso-Rodriguez, J. A., Jimeno, M. L., Rodriguez, B., Savona, G., and Bruno, M. 1983. Abietane diterpenoids from the root of Salvia phlomoides. Phytochemistry 22:2005-2009.
13. Kang, H. Y., Sameshima, K., and Takamura, N. 1993. Termite resistance test of hardwoods of Kochi prefecture growth. Mokuzai Gakkaishi 39:345-351.
14. Kano, H., Shibutani, S., Hayashi, K., Iijima, Y., and Doi, S. 2004. Effect of high-temperature drying processes on termite resistance of Sugi (Cryptomeria japonica) heartwood. Mokuzai Gakkaishi 50:91-98.
15. Kofujita, H., Fujino, Y., Sasaki, T., Hasebe, M., Ota, M., and Suzuki, K. 2001. Antifungal activity of the bark of Cryptomeria japonica and its relevant components. Mokuzai Gakkaishi 47:479-486.
16. Kofujita, H., Ota, M., Takahashi, K., Kawai, Y., and Hayashi, Y. 2002. A diterpene quinone from the bark of Cryptomeria japonica. Phytochemistry 61:895-898.
17. Kofujita, H., Fujino, Y., Ota, M., and Takahashi, K. 2006. Antifungal diterpenes from the bark of Cryptomeria japonica D. Don. Holzforschung 60:20-23.
18. Kondo, Y., Ikenoue, T., and Takemoto, T. 1963. Structure of Xanthoperol. Chem. Pharm. Bull. 11:678-680.
19. Kupchan, S. M., Karim, A., and Marcks, C. 1969. Taxodione and Taxodone, two novel diterpenoid quinone methide tumor inhibitors from Taxodium distichum. J. Org. Chem. 34:3912-3919.
20. Kusumoto, N., Murayama, T., Kawai, Y., Ashitani, T., Ogiyama, K., and Takahashi, K. 2008. Taxodal, a novel irregular abietane-type diterpene from the cones of Taxodium distichum. Tetrahedron Lett. 49:4845-4847.
21. Li, A., She, X., Zhang, J., Wu, T., and Pan, X. 2003. Synthesis of C-7 oxidized abietane diterpenes from racemic ferruginyl methyl ether. Tetrahedron 59:5737-5741.
22. Lin, L.Z., Blaskó, G., and Cordell, G. A. 1989. Diterpenes of Salvia prionitis. Phytochemistry 28:177-181.
23. Matsui, T., Matsushita, Y., Sugamoto, K., and Yano, H. 2004. Isolation of terpenoids from Sugi (Cryptomeria japonica) wood and chemical conversion of ferruginol. Memoirs of the Fac. Eng. Miyazaki Univ. 33:63-73.
24. Marques, C. G., Rijo, P., Simões, M. F., Duarte, M. A., and Rodriguez, B. 2006. Abietanes from Plectranthus grandidentatus and P. Hereroensis against methicillin- and vancomycin-resistant bacteria. Phytomed. 13:267-271.
25. Nagahama, S., Iwaoka, T., and Ashitani, T. 2000. Terpenoids of the wood oil of Sugi (Cryptomeria japonica) VI. Mokuzai Gakkaishi 46:225-230.
26. Otto, A., White, J. D., and Simoneit, B. R. T. 2002. Natural product terpenoids in Eocene and Miocene conifer fossils. Science 297:1543-1545.
27. Otto, A., Simoneit, B. R. T., and Rember, W. C. 2003. Resin compounds from the seed cones of three fossil conifer species from the Miocene Clarkia flora, Emerald Creek, Idaho, USA, and from related extant species. Rev. Palaeobot. Palynol. 126:225-241.
28. Otto, A., Simoneit, B. R. T., and Rember, W. C. 2005. Conifer and angiosperm biomarkers in clay sediments and fossil plants from the Miocene Clarkia Formation, Idaho, USA. Org. Geochem. 36:907-922.
29. Sato, A., Senda, M., Kakutani, T., Watanabe, Y., and Kitao, K. 1966. Extractives from heartwood of Metasequoia glyptostroboides Hu et Cheng (part 1). Bull. Wood Res. Inst. Kyoto univ. 39:13-21.
30. Scheffrahn, R. H., Hsu, R. C., Su, N. Y., Huffman, J. B., Midland, S. L., and Sims, J. J. 1988. Allelochemical resistance of Bald Cypress, Taxodium distichum, heartwood to the subterranean termite, Coptotermes formosanus. J. Chem. Ecol. 14:765-776.
31. Si, Y., Yao, X. H., Zhang, C. K., and Tu, Z. B. 2005. C-32 Triterpenes from Taxodium ascendens. Biochem. Syst. Ecol. 33:211-214.
32. Son, K. H., Oh, H. M., Choi, S. K., Han, D. C., and Kwon, B. M. 2005. Anti-tumor abietane diterpenes from the cones of Sequoia sempervirens. Bioorg. Med. Chem. Lett. 15:2019-2021.
33. Tellez, M. R., Khan, I. A., Kobaisy, M., Schrader, K. K., Dayan, F. E., and Osbrink, W. 2002. Composition of the essential oil of Lepidium meyenii (Walp.). Phytochemistry 61:149-155.
34. Tezuka, Y., Kasimu, R., Li, J. X., Basnet, P., Tanaka, K., Namba, T., and Kadota, S. 1998. Constituents of roots of Salvia deserta Schang. (Xinjiang-Danshen). Chem. Pharm. Bull. 46:107-112.
35. Ulubelen, A., Öksüz, S., Kolak, U., Tan, N., Bozok-Johansson, C., Çelik, C., Kohlbau, H. J., and Voelter, W. 1999. Diterpenoids from the roots of Salvia bracteata. Phytochemistry 52:1455-1459.
36. Wenkert, E. and Buckwalter, B. L. 1972. Carbon-13 nuclear magnetic resonance spectroscopy of naturally occurring substances. X. Pimaradienes. J. Am. Chem. Soc. 94:4367-4369.
37. Yano, S. and Furuno, T. 1994. Resin acids from extracts of pine cones of Kuromatsu (Pinus thunbergii). Mokuzai Gakkaishi 40:72-77.
38. Yamamoto, H., Hirao, T., Wakayama, K., and Chida, T. 2003. Abietane diterpenes from cones of Taxodium distichum Rich. Bull. Fac. Edu. Ibaraki Univ. 52:31-39.
39. Yang, Z., Kitano, Y., Chiba, K., Shibata, N., Kurokawa, H., Doi, Y., Arakawa, Y., and Tada, M. 2001. Synthesis of variously oxidized abietane diterpenes and their antibacterial activities against MRSA and VRE. Bioorg. Med. Chem. 9:347-356.