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On the Components of the Essential Oil from Tetrapanax

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On the Components of the Essential Oil from Tetrapanax Agric. Biol. Chem., 44 (8), 1953•`1955 , 1980 1953 Note sesquiterpenes,4) seems to be superior to T. papyriferum which contains mainly acyclic sesquiterpenes in the oil such as trans-nerolidol and trans-ƒÀ-farnesene. On the Components of the Essential That is, the phylogenetic position of F. japonica in the Oil from Tetrapanax Araliaceae group is shown to be an end species of differentiation from the viewpoint of chemical systematics. papyriferum K. Koch* This result coincides with the geographical distribution of the above two species. Shin-ichi FUJITA EXPERIMENTAL Department of Education, Mukogawa Women's University, Materials. Sample I. The leaves were collected from Ikebiraki, Nishinomiya 663, Japan several garden trees in the Takarazuka Family Land at Takarazuka-shi, Hyogo Prefecture, on January 8, 1974. Received February 18, 1980 Sample II. The leaves were collected from a tree in the campus of Mukogawa Gakuin at Nishinomiya-shi, Hyogo Prefecture, on November 5, 1974. Tetrapanax papyriferum K. Koch: Rice paper plant Isolation of the essential oils. Each lot of fresh material (Japanese name, "Kamiyatsude") of the Araliaceae grows cut in to small pieces was steam distilled. The distillates naturally in southern China and Formosa, and is widely were saturated with sodium chloride and then extracted planted as a garden tree in Japan.1) Formerly, this plant with ether, and the ether extract was dried over anhydrous known as Fatsia papyrifera Benth. et Hook.2) was included sodium sulfate. The ether was removed to give the essential in the same genus, Fatsia Linn., as Fatsia japonica Dence. oil. et Planch. (Japanese name, "Yatsude") which is an The size and weight of the used fresh materials, the endemic plant of Japan. obtained oils, the yields of the oil from the fresh leaves are From the viewpoint of chemical systematics, the shown in Table II. essential oil in leaves from this plant was examined in order to compare it with that of F. japonica which was Gas-liquid chromatographic analysis (GLC). Analytical reported previously.3) This paper presents the results of the GLC was performed on a Shimadzu GC-4BPT type gas investigation and a discussion on the relationship between chromatograph with a thermal conductivity detector, the above two species. using a 3 m •~ 3 mm„U, stainless steel column containing The yields of the essential oil obtained from fresh leaves 30% PEG-6000 on 80•`100 mesh Celite 545. Hydrogen as of T. papyriferum were 0.014% (Sample I) and 0.020% a carrier gas was maintained at 80 ml/min, and the column (Sample II). The oil consisted of more than 40 com temperature was 160•Ž. ponents, listed in Table I. The percentages of the constituents of the oil were The major sesquiterpenes were ƒÀ-caryophyllene calculated from the areas of the peaks on gas chro (10.5•`14.2% in the oil), trans-ƒÀ-farnesene (7.0•`8.0%), matograms. ƒÀ-selinene (7.1•`7.4%), ƒÂ-cadinene (4.1•`5.0%), and trans nerolidol (3.4•`5.9%); the noticeable monoterpenes were Identification of individual components. Each oil was a-pinene (4.9•`13,3%), ƒÀ-pinene (4.2•`10.1%), and a column chromatographed on activated alumina (300 terpineol (3.0•`4.5%). mesh) using hexane-ether as an eluent. The hydrocarbon On the other hand, the yield from fresh leaves of F. fractions were peaks 1, 3, 4, 5, 6, 7, 14, 16, 17, 18, 20, 21, japonica was 0.004•`0,022%, and the characteristic com 22, 23, 25, 26, 27, 28, 33, and 34. And the oxygenated fractions were peaks 2, 8, 9, 10, 12, 13, 15, 19, 24, 29, 30, pounds of the oil were epi-cubenol (14.3% in the oils, average of four samples), ƒÂ-cadinene (13.4%), ƒ¿-muurolene 31, 32, 35, 36, 37, 38, 39, and 40. (5.8%), ƒ¿-copaene (5.5%), ƒ¿-cubebene (5.2%), and cala The main components of each fraction were isolated in a menene (4.6°%).3) pure state by means of preparative GLC and were As to the degree of phylogenetic evolution, F. japonica identified by comparing their infrared spectra (IR) and which contains mainly epi-cubenol, ƒÂ-cadinene, ƒ¿-muu GLC retention times (Rt) with those of authentic samples. rolene, ƒ¿-copaene, ƒ¿-cubebene, and calamenene as the Some minor components were identified by Rts using only latter formed compounds on the biosynthetic pathways of PEG-6000 (30%) and Silicone DC-550 (30%) columns. Furthermore, the original oil (Sample I) was analyzed by * Miscellaneous Contributions to the Essential Oil of gas chromatography-mass spectrometry (GC-MS). the Plants from Various Territories. Part XLV. For Part XLIV, see S. Fujita and H. Wada, Yakugaku Zasshi, 100, 763 (1980). 1954 S. FUJITA TABLE I. COMPONENTSOF THEESSENTIAL OIL IN LEAVESOF T. papyriferum (%) a GC: PEG-6000 (30%) 3 m x 3 mm„U, 160•Ž, 80 ml/min H2. b S. H. C.: Sesquiterpene hydrocarbon. Essential Oil of Tetrapanax papyriferum 1955 TABLE II. PROPERTIES OF THE MATERIALS Acknowledgments. The author wishes to thank the AND THE ESSENTIAL OILS late Dr. Y. Fujita for his valnable suggestions in this work. REFERENCES 1) K. Shibata, "A Cyclopedia of Useful Plants and Plant Products," Hokuryukan Co., Ltd., Tokyo, 1949, p. 122; A. F. Hill, "Economic Botany," 2nd Ed., McGraw-Hill, New York, 1952, p. 231. 2) R. Kanehira, "Formosan Trees," Yokendo Ltd., Tokyo, 1936, p. 529. 3) S. Fujita, R. Hayashi and Y. Fujita, Nippon Kagaku Kaishi, 1978, 315. 4) V. Herout, "Aspects of Chemistry and Biochemistry," ed. by T. W. Goodwin, Academic Press, London, 1971, p. 60; G. A. Cordell, Chem. Rev., 76, 425 (1976)..
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