Seven germacranolides, eupaglehnins A, B, C, D, E, and F, and 2α-acetoxyepitulipinolide from Eupatorium glehni

Chemical and Pharmaceutical Bulletin

Volumn 50, Issue 9, 2002, Pages 1250-1254

  Tori, Motoo ^a   Takeichi, Yoshiko ^a   Kuga, Hiroe ^a   Nakashima, Katsuyuki ^a   Sono, Masakazu ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

Compositae; Eupaglehnin; Eupatorium glehni; Germacranolide; Sesquiterpene

Indexed keywords

2ALPHA ACETOXYEPITULIPINOLIDE; CHLORINE; ESTER; EUPAGLEHNIN A; EUPAGLEHNIN B; EUPAGLEHNIN C; EUPAGLEHNIN D; EUPAGLEHNIN E; EUPAGLEHNIN F; EUPATORIOPICRIN; EUPATORIUM GLEHNI EXTRACT; GERMACRANOLIDE DERIVATIVE; LACTONE; PLANT EXTRACT; SESQUITERPENOID; UNCLASSIFIED DRUG; GERMACRANOLIDE; SESQUITERPENE;

ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DATA ANALYSIS; DRUG ISOLATION; DRUG STRUCTURE; EUPATORIUM GLEHNI; HUMAN; HUMAN CELL; MEDICINAL PLANT; SPECTROSCOPY; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; EUPATORIUM; INFRARED SPECTROPHOTOMETRY; ISOLATION AND PURIFICATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EUPATORIUM; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; SESQUITERPENES; SESQUITERPENES, GERMACRANE; SPECTROPHOTOMETRY, INFRARED;

EID: 0036730296     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.50.1250     Document Type: Article

References (36)

1. Kupchan S. M., Fujita T., Maruyama M., Britton R. W., J. Org. Chem., 38, 1260-1264 (1973).
2. Takahashi T., Eto H., Ichimura T., Murae T., Chem. Lett., 1978, 1345-1348 (1978).
3. Takahashi T., Ichimura T., Murae T., Chem. Pharm. Bull., 27, 2539-2543 (1979).
4. Woerdenbag H. J., Meijer C., Mulder N. H., de Vries E. G., Hendriks H., Malingre Th. M., Planta Med., 52, 112-114 (1986).
5. Woerdenbag J., Moskal T. A., Pras N., Malingré Th. M., J. Nat. Prod., 56, 849-856 (1993).
6. The plant was identified by Dr. Takayuki Kawahara, Hokkaido Branch of the Forestry and Forest Products Research Institute, Forestry Agency, Ministry of Agriculture, Forestry and Fisheries, to whom many thanks are due. According to his research, the plant name E. sachalinense should be changed to E. glehni based on gene identification methodology.
7. Kawahara T., Yahara T., Watanabe K., Bot. Mag. Tokyo, 102, 165-179 (1989).
8. Kawahara T., Yahara T., Watanabe K., Plant Species Biol., 4, 37-46 (1989).
9. Tori M., Kawahara M., Sono M., Tetrahedron Lett., 38, 1965-1968 (1997).
10. Tori M., Kawahara M., Sono M., Phytochemistry, 47, 401-409 (1998).
11. Tori M., Katto A., Sono M., Phytochemistry, 52, 487-493 (1999).
12. Tori M., Shiotani Y., Tanaka M., Nakashima K., Sono M., Tetrahedron Lett., 41, 1797-1799 (2000).
13. Tori M., Takeichi Y., Kuga H., Nakashima K., Sono M., Heterocycles, 52, 1075-1078 (2000).
14. Tori M., Ohara Y., Nakashima K., Sono M., J. Nat. Prod., 64, 1048-1051 (2001).
15. Ohno N., Mabry T., Phytochemistry, 18, 1003-1006 (1979).
16. Bohlmann F., Adler A., King R. M., Robinson H., Phytochemistry, 21, 1169-1170 (1982).
17. Zdero C., Bohlmann F., Planta Med., 53, 169-172 (1987).
18. Although the abstract of Ref. 16 states that 2α-acetoxyeupatolide was isolated from the plant, compound 1 in this paper must be 2α-hydroxyeupatolide and its name was erroneously assigned to be 2α-acetoxyeupatolide.
19. Private communication with Professor T. Takahashi.
20. Monde K., Satoh H., Nakamura M., Tamura M., Takasugi M., J. Nat. Prod., 61, 913-921 (1998).
21. Martini U., Zapp J., Becker H., Phytochemistry, 47, 89-96 (1998).
22. Bruno M., Fazio C., Piozzi F., Savona G., Rodrîguez B., de la Torre M. C., Phytochemistry, 40, 505-507 (1995).
23. Hashimoto T., Tori M., Asakawa Y., Phytochemistry, 28, 3377-3381 (1989), and references cited therein.
24. Dolejs L., Herout V., Collect. Czech. Chem. Commun., 27, 2654-2661 (1962).
25. Doskotch R. W., El-Feraly R. W., J. Org. Chem., 35, 1928-1936 (1970).
26. Drozdz B., Grabarczyk H., Samek Z., Holub M., Herout V., Sorm F., Collect. Czech. Chem. Commun., 37, 1546-1554 (1972).
27. Woerdenbag H. J., Meijer C., Mulder N. H., de Vries E. G. E., Hendriks H., Malingré Th. M., Planta Med., 52, 112-114 (1986).
28. Woerdenbag H. J., Lemstra W., Hendriks H., Malingré Th. M., Konings A. W. T., Planta Med., 53, 318-322 (1987).
29. Woerdenbag H. J., Moskal T. A., Pras N., Malingré Th. M., J. Nat. Prod., 56, 849-856 (1993).
30. Lee K. H., Huang H. C., Huang E. S., Furukawa H., J. Pharm. Sci., 61, 629-631 (1972).
31. McPhail A. T., Onan K. D., J. Chem. Soc. Perkin Trans. 2, 1975, 1798-1801 (1975).
32. Bohlmann F., Hirschmann G. S., Jakupovic J., Phytochemistry, 23, 1435-1437 (1984).
33. De Hernández Z. N. J., Catalán C. A. N., Hernández L. R., Guerra-Ramírez D., Joseph-Nathan P., Phytochemistry, 51, 79-82 (1999).
34. Herz W., de Groote R., Murari R., Kumar N., J. Org. Chem., 44, 2784-2788 (1979).
35. Gill R. G., Pacciaroni A. D. V., Oberti J. C., Diaz J. G., Herz W., Phytochemistry, 31, 593-596 (1992).
36. Ito K., Sakakibara Y., Haruna M., Lee K.-H., Chem. Lett., 1979, 1469-1472 (1979).