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Abietane-type and labdane-type diterpenoids from the cones ofChamaecyparis obtusa
Journal of Wood Science volume 48, pages 326–330 (2002)
Abstract
A novel compound, 8(17),12E,14-labdatrien-19-al (trans-communal), was isolated from ethyl acetate extract of young cones of hinoki (Chamaecyparis obtusa Endl.). The chemical structure of the compound was determined mainly with various nuclear magnetic resonance spectral techniques. Its stereochemistry was determined by derivation to a known compound,trans-communol. In addition to this compound, four known compounds — ferruginol, chamaecydin, 12-hydroxy-6,7-seco-abieta-8,l 1,13-triene-6,7-dial, and frans-communic acid — were isolated. All isolated compounds were subjected to an antifeedant bioassay against the pest insectSpodoptera litura. Results of the bioassay showed that chamaecydin and 12-hydroxy-6,7-seco-abieta-8,11,13-triene-6,7-dial had antifeedant activity.
References
Fujise Y, Murata I, Ito S, Nozoe T (1964) Chemical constituents of essential oil ofChamaecyparis obtusa (SIEB. et ZUCC.). Chem Pharm Bull 12:991–994
Matsubara Y, Sawabe A, Iba H, Iizuka Y (1990) Structure of terpenoid glycosides in the leaf of hinoki (Chamaecyparis obtusa SIEB. et ZUCC). Agric Biol Chem 54:555–556
Ohashi H, Imamura H (1971) Resin exudates of the diseased Japanese cypress (Chamaecyparis obtusa Endl.) I. Mokuzai Gakkaishi 18:409–413
Kondo R, Imamura H (1986) Antifungal compounds in heartwood extractives of hinoki (Chamaecyparis obtusa Endl.) (in Japanese). Mokuzai Gakkaishi 32:213–217
Yamamoto H, Asano N, Sawano C, Sone T, Gasha T, Ono Y (1997) Diterpenes isolated from the resin of the resinous stem canker of Japanese cypress,Chamaecyparis obtusa. Mokuzai Gakkaishi 43:558–565
Hanari N, Ono Y, Ooi T, Yamamoto H (1998) Diterpenes extracted by a polar solvent from the bark of the resinous stem canker ofChamaecyparis obtuse (in Japanese). Mokuzai Gakkaishi 44:342–350
Ozaki N, Hasegawa S, Hirose Y (1983) Terpenoids from the seed ofChamaecyparis obtusa. Phytochemistry 22:1771–1773
Hirose Y, Hasegawa S, Ozaki N, Iitaka N (1983) Three new terpenoid quinone methods from the seed ofChamaecyparis obtuse. Tetrahedron Lett 24:1535–1538
Shieh B, Iizuka Y, Matsubara Y (1981) Monoterpenoid and sesquiterpenoid constituents of the essential oil of hinoki (Chamaecyparis obtusa SIEB, et ZUCC. Endl.). Agric Biol Chem 45:1497–1499
Asano N, Yamamoto H (1994) Isolation and analysis using gas chromatography-mass spectrometry of terpenes from leaf and cones ofChamaecyparis obtusa. Bull Fac Educ Ibaraki Univ Nat Sci 43:61–73
Matsumoto T, Usui S (1979) A simple total synthesis of (+)-ferruginol, (+)-sempervirol, and (+)-podocarpa-8(14)-en-13-one. Bull Chem Soc Jpn 52:212–215
Yanagawa T, Hirose Y (1971) Terpenoids. XXIX Diterpenes in the wood ofJuniperus rigida SIEB, et ZUCC. Mokuzai Gakkaishi 17:306–310
Teresa JP, Feliciano SS, Egido T, Barrero AF (1977) Components ofJuniperus thurifera L. berries. II. An Quim 73:151–152
Thomas BR (1966) The chemistry of the order Araucariales. Part 4. The bled resins ofAgathis australis. Acta Chem Scand 20:1074–1081
Bohlmann F, Jakupovic J, King RM, Robinson H (1980) Neue entatisirenund ent-kaurensaure-derivate ausHelianthus-arten. Phytochemistry 19:863–868
Romeo JT, Simmonds MSJ (1989) Nonprotein amino acid feeding deterrents from calliandra. In: Arnason JT, Philogene BJ, Morand P (eds) Insecticide of plant origin. American Chemical Society, Washington, DC, p 59
Lajide L, Escoubas P, Mizutani J (1993) Antifeedant activity of metabolites ofAristolochia albida against the tobacco cutworm,Spodoptera litura. J Agric Food Chem 41:669–673
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Fukushima, Ji., Yatagai, M. & Ohira, T. Abietane-type and labdane-type diterpenoids from the cones ofChamaecyparis obtusa . J Wood Sci 48, 326–330 (2002). https://doi.org/10.1007/BF00831355
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DOI: https://doi.org/10.1007/BF00831355