New eudesmane-type sesquiterpenoids and other volatile constituents from the roots of Gynura bicolor DC

Flavour and Fragrance Journal

Volumn 26, Issue 1, 2011, Pages 55-64

  Shimizu, Yasuhiro ^a,b   Imayoshi, Yuriko ^b   Kato, Mika ^a,b   Maeda, Kazuhiro ^b   Iwabuchi, Hisakatsu ^b   Shimomura, Koichiro ^a  

^a TOYO UNIVERSITY   (Japan)

^b SAN EI GEN F F I INC   (Japan)

Author keywords

Aroma impact compound; Enantioselective analysis; Gynura bicolor; Methoxypyrazine; New sesquiterpenoid; Polyacetylene; Root

Indexed keywords

AROMA-IMPACT COMPOUND; ENANTIOSELECTIVE ANALYSIS; GYNURA BICOLOR; METHOXYPYRAZINE; ROOT; SESQUITERPENOIDS;

ACETYLENE; ESSENTIAL OILS; ETHERS; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; RESONANCE; VOLATILE ORGANIC COMPOUNDS;

NUCLEAR MAGNETIC RESONANCE;

1 TRIDECENE 3,5,7,9,11 PENTAYNE; 3 ISOPROPYL 6 METHYL 10 OXOUNDECA 2,6 DIENAL; ALISMOL; ALISMOXIDE; BETA FARNESENE; CARYOPHYLLENE; EUDESM 11 EN ALPHA OL; EUDESMANE DERIVATIVE; HUMULENE; INTERMEDEOL; PLANT EXTRACT; PYRAZINE DERIVATIVE; SESQUITERPENOID; TERPENOID DERIVATIVE; UNCLASSIFIED DRUG; VOLATILE AGENT;

AROMA; ARTICLE; ASTERACEAE; CHEMICAL STRUCTURE; GAS CHROMATOGRAPHY; GYNURA BICOLOR; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; OLFACTOMETRY; PLANT ROOT; SYNTHESIS;

GYNURA BICOLOR;

EID: 78650143201     PISSN: 08825734     EISSN: 10991026     Source Type: Journal    
DOI: 10.1002/ffj.2016     Document Type: Article

References (48)

1. T. Tanaka, S. Nakano (ed.). Tanaka's Cyclopedia of Edible Plants of the World. Keigaku, Tokyo, 1976, p. 349.
2. C.-F. Chau, S.-H. Wu Trends Food Sci. Technol. 2006, 17, 313.
3. Shogakukan, Shanghai Science and Technology Publishers (ed.). In The Dictionary of Chinese Drugs, Vol. I, Shogakukan, Tokyo, 1985, pp. 389-390.
4. K. Yoshitama, M. Kaneshige, N. Ishikura, F. Araki, S. Yahara, K. Abe J. Plant Res. 1994, 107, 209.
5. M. Hayashi, S. Miwa, T. Yagi, T. Michihata, T. Enomoto Bull. Ishikawa Agric. Res. Centre 2002, 24, 25.
6. M. Hayashi, K. Iwashita, N. Katsube, K. Yamaki, M. Kobori Nippon Shokuhin Kagaku Kougaku Kaishi 2002, 49, 519.
7. Y. Shimizu, Y. Imayoshi, M. Kato, K. Maeda, H. Iwabuchi, K. Shimomura Flavour Fragr. J. 2009, 24, 251.
8. R. M. Seifert, R. G. Buttery, D. G. Guadagni, D. R. Black, J. G. Harris J. Agric. Food Chem. 1972, 20, 135.
9. H. Iwabuchi, M. Yoshikura, S. Obata, W. Kamisako Yakugaku Zasshi. 1984, 104, 951.
10. W. A. König, N. Bülow, C. Fricke, S. Melching, A. Rieck, H. Muhle Phytochemistry 1996, 23, 629.
11. A. M. Adio Tetrahedron 2009, 65, 1533.
12. W. Feger, H. Brandauer, H. Ziegler J. Essent. Oil Res. 2001, 13, 274.
13. C. Bicchi, E. Liberto, M. Matteodo, B. Sgorbini, L. Mondello, B. d'Acampora Zellner, R. Costa, P. Rubiolo Flavour Fragr. J. 2008, 23, 382.
14. E. Cicchetti, P. Merle, A. Chaintreau Flavour Fragr. J. 2008, 23, 450.
15. T. E. Acree, J. Barnard, D. G. Cunningham Food Chem. 1984, 14, 273.
16. H. Van den Dool, P. D. Kratz J. Chromatogr. 1963, 11, 463.
17. R. P. Adams Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry, 4th edition. Allured, Carol Stream, IL, 2007.
18. Wiley Registry 7th edition. NIST: 2005, [12 June 2010].
19. S. M. Colby, J. Crock, B. D. Rizzo, P. G. Lemaux, R. Croteau Proc. Natl. Acad. Sci. U. S. A. 1998, 95, 2216.
20. B. Marongiu, A. Piras, S. Porcedda, E. Tuveri Flavour Fragr. J. 2006, 21, 718.
21. I. Kitagawa, M. Kobayashi, Z. Cui, Y. Kiyota, M. Ohnishi Chem. Pharm. Bull. 1986, 34, 4590.
22. M. Yoshikawa, H. Matsuda J. Trad. Med. 2002, 19, 119.
23. J.-W. De Kraker, M. C. R. Franssen, A. De Groot, T. Shibata, H. J. Bouwmeester Phytochemistry 2001, 58, 481.
24. N. Uchiyama, K. Matsunaga, F. Kikuchi, G. Honda, A. Tsubouchi, J. N. Shimada, T. Aoki Chem. Pharm. Bull. 2002, 50, 1514.
25. S. Z. Choi, S. O. Lee, S. U. Choi, K. R. Lee Arch. Pharm. Res. 2003, 26, 521.
26. F. Kikuchi, K. Matsuo, M. Ito, T. K. Qui, G. Honda Chem. Pharm. Bull. 2004, 52, 1495.
27. R. E. Corbett, R. A. J. Smith Tetrahedron Lett. 1967, 1009.
28. G. L. Chetty, V. B. Zalkow, L. H. Zalkow Tetrahedron Lett. 1968, 3223.
29. A. S. Feliciano, M. Medarde, B. D. Rey, J. M. Miguel Del Corral, A. F. Barrero Phytochemistry 1990, 29, 3207.
30. R. P. W. Keselmans, J. B. P. A. Wijnberg, A. J. Minnaard, R. E. Walinga, A. de Groot J. Org. Chem. 1991, 56, 7237.
31. P. M. Abreu, R. G. Noronha Flavour Fragr. J. 1997, 12, 79.
32. Y. Oshima, T. Itokawa, H. Hikino Phytochemistry 1983, 22, 183.
33. M. Yoshikawa, S. Hatakeyama, N. Tanaka, Y. Fukuda, N. Murakami, J. Yamahara Chem. Pharm. Bull. 1992, 40, 2582.
34. M. Yoshikawa, S. Yamaguchi, H. Matsuda, Y. Kohda, H. Ishikawa, N. Tanaka, J. Yamahara, N. Murakami Chem. Pharm. Bull. 1994, 42, 1813.
35. G. Blay, B. Garcia, E. Molina, J. R. Pedro J. Org. Chem. 2006, 71, 7866.
36. M. Yoshikawa, S. Hatakeyama, N. Tanaka, T. Matsuoka, J. Yamahara, N. Murakami Chem. Pharm. Bull. 1993, 41, 2109.
37. S.-Y. Cheng, Y.-C. Huang, Z.-H. Wen, S.-F. Chiou, S.-K. Wang, C.-H. Hsu, C.-F. Dai, C.-Y. Duh Tetrahedron Lett. 2009, 50, 802.
38. J. S. Sörensen, D. Holme, E. T. Borlaug, N. A. Sörensen Acta Chem. Scand. 1954, 8, 1769.
39. R. G. Binder, M. E. Benson, R. A. Flath J. Agric. Food Chem. 1990, 38, 1245.
40. M. Takasugi, S. Kawashima, N. Katsui, A. Shirata Phytochemistry 1987, 26, 2957.
41. S. A. Zid, Y. Orihara Plant Cell Tissue Cult. 2005, 81, 65.
42. G. Guillet, B. J. R. Philogène, J. O'Meara, T. Durst, J. T. Arnason Phytochemistry 1997, 46, 495.
43. K. E. Murray, J. Shipton, F. B. Whitfield Chem. Ind. (London) 1970, 897.
44. R. G. Buttery, R. M. Seifert, R. E. Lundin, D. G. Guadagni, L. Ling Chem. Ind. (London) 1969, 490.
45. R. M. Seifert, R. G. Buttery, D. G. Guadagni, D. R. Black, J. G. Harris J. Agric. Food Chem. 1970, 18, 246.
46. J. W. K. Burrell, R. A. Lucas, D. M. Michalkiewicz, G. Riezebos Chem. Ind. (London) 1970, 1409.
47. H. J. Takken, L. M. Van der Linde, M. Boelens, J. M. Van Dort J. Agric. Food Chem. 1975, 23, 838.
48. C. L. Steele, J. Crock, J. Bohlmann, R. Croteau J. Biol. Chem. 1998, 273, 2078.