Biosynthesis of phytoecdysteroids in Ajuga hairy roots: Clerosterol as a precursor of cyasterone, isocyasterone and 29-norcyasterone

Tetrahedron Letters

Volumn 44, Issue 2, 2003, Pages 323-326

  Okuzumi, Keiko ^a   Hara, Noriyuki ^a   Fujimoto, Yoshinori ^a   Yamada, Junko ^b   Nakamura, Atsuko ^b   Takahashi, Kyoko ^b   Morisaki, Masuo ^b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b KEIO UNIVERSITY   (Japan)

Author keywords

29 norcyasterone; Biosynthesis; Clerosterol; Codisterol; Cyasterone; Ecdysteroids; Isocyasterone; Steroids and sterols

Indexed keywords

29 NORCYASTERONE; CLEROSTEROL; CYASTERONE; ISOCYASTERONE; STEROID; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; FEEDING; HAIR ROOT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; STEREOCHEMISTRY; STEROL SYNTHESIS;

EID: 0037420998     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02565-0     Document Type: Article

References (25)

1. (a) Lafont R.; Horn, D.H.S. In Ecdysone; Koolman J., Ed.; Thieme: New York, 1989; pp. 39-64;
2. (b) Camps, F. In Ecological Chemistry and Biochemistry of Plant Terpenoids; Harbone, J. B.; Tomas-Barberán, F. A., Eds.; Clarendon Press: Oxford 1991;331-376.
3. (a) Takemoto T., Hikino Y., Nomoto K., Hikino H. Tetrahedron Lett. 8:1967;3191-3194.
4. (b) Hikino H., Nomoto K., Takemoto T. Tetrahedron. 27:1971;315-321.
5. (a) Imai S., Toyosato T., Sakai M., Sato Y., Fujioka S., Murata E., Goto M. Chem. Pharm. Bull. 17:1969;340-342;
6. (b) Camps F., Coll J. Phytochemistry. 32:1993;1361-1370.
7. Matsumoto T., Tanaka N. Agric. Biol. Chem. 55:1991;1019-1025.
8. (a) Hikino, H.; Nomoto, K.; Takemoto, T. Chem. Pharm. Bull. 1971, 19, 433-435;
9. Hikino H., Nomoto K., Takemoto T. Phytochemistry. 10:1971;3173-3178.
10. Camps F., Coll J., Cortel A. Chem. Lett. 1982;1313-1316.
11. Warren J.T., Hetru C. Invertebr. Reprod. Dev. 18:1990;91-99.
12. Adler J.H., Grebenok R.J. Lipids. 30:1995;257-262.
13. Boid R., Rees H.H., Goodwin T.W. Biochem. Soc. Trans. 2:1974;1066-1070.
14. Boid R., Rees H.H., Goodwin T.W. Biochem. Physiol. Pflanzen. 168:1975;27-40.
15. Nagakari M., Kushiro T., Matsumoto T., Tanaka N., Kakinuma K., Fujimoto Y. Phytochemistry. 36:1994;907-910.
16. Fujimoto Y., Nakagawa T., Yamada J., Morisaki M. J. Chem. Soc., Chem. Commun. 1996;2063-2064.
17. Okuzumi, K.; Fujimoto, Y., unpublished results.
18. Fujimoto Y., Ohyama K., Nomura K., Hyodo R., Takahashi K., Yamada J., Morisaki M. Lipids. 35:2000;279-288.
19. Yagi T., Morisaki M., Kushiro T., Yoshida H., Fujimoto Y. Phytochemistry. 41:1996;1057-1064.
20. 13C NMR δ: 18.72 (C-27).
21. Kline T.B., Prestwich G.D. Tetrahedron Lett. 23:1982;3043-3046.
22. Kimura M., Khalifa F.A.M., Ikekawa N. Chem. Pharm. Bull. 32:1984;4372-4381.
23. Yamada, J.; Takahashi, K.; Morisaki, M.; Fujimoto, Y., unpublished results.
24. Imai S., Fujioka S., Murata E., Otsuka K., Nakanishi K. Chem. Commun. 1969;82-83.
25. Analysis of the sterol fraction of C. officinalis roots, which contain 1 and 2, confirmed that (24α)-alkylsterols (sitosterol 54% and stigmasterol 33%) are contained exclusively.