Metabolic origin of C-26 and C-27 of isofucosterol in tissue cultures of Catharanthus roseus

Natural Product Letters

Volumn 11, Issue 3, 1998, Pages 207-210

  Fujimoto, Yoshinori ^a   Sato, Naoko ^a   Sekiyama, Yasuyo ^a   Ito, Michiko ^a   Suzuki, Takayuki ^a   Hamada, Hiroki ^b   Morisaki, Masuo ^c  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

^c KEIO UNIVERSITY   (Japan)

Author keywords

Biosynthesis; Catharanthus roseus; Isofucosterol; Phytosterol

Indexed keywords

ACETIC ACID; CARBON 13; ISOFUCOSTEROL; METHYL GROUP; MEVALONIC ACID; SITOSTEROL; STEROL; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CELL CULTURE; HIGHER PLANT; PLANT CELL;

CATHARANTHUS ROSEUS;

EID: 0031976224     PISSN: 10575634     EISSN: None     Source Type: Journal    
DOI: 10.1080/10575639808044948     Document Type: Article

References (14)

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2. 13C Assignment of Diastereotopic C-26 and C-27 Methyl Groups of 24-Methylene-cholesterol: Steric Course of Hydrogen Migration from C-24 to C-25 during Its Biosynthesis in Higher Plants. Chem. Pharm. Bull., 45, 224-226.
3. D. -A. Guo, Z. Jia, W. D. Nes (1996) Stereochemistry of Hydrogen Migration from C-24 to C-25 during Phytosterol Biomethylation. J. Am. Chem.Soc. 118, 8507-8508.
4. 3]Acetate. J. Chem. Soc., Chem. Commun., 1139-1141.
5. 3]Acetate. J. Chem. Soc., Chem. Commun., 1139-1141.
6. 13C]Mevalonate. Phytochemistry, 31, 805-811.
7. Y. Fujimoto, N. Sato, T. Okuzumi, J. Yamada, and M. Morisaki, Stereochemistry of the Reduction of 24-Ethyldesmosterol to Sitosterol in Tissue Cultures of Oryza sativa, submitted for publication.
8. 2]Acetate in Tissue Cultures of Physalis perviana - The Stereochemistry of the Hydride Shift from C-24 to C-25. J. Chem. Soc., Perkin Trans. 1, 105-109.
9. F. Nicotra, F. Ronchetti, G. Russo, G. Lugaro, M. Casellato (1981) Stereochemical Fate of the Isopropylidene Methyl Groups of Lanosterol during the Biosynthesis of Isofucosterol in Pinus pines. J. Chem. Soc., Perkin Trans. 1, 498-502.
10. 24(25)-cholesterols as Immediate Biosynthetic Precursors of 24-Alkylsterols in Higher Plants. Tetrahedron, 53, 877-884.
11. 13C]Acetate in Tissue Cultures of Isodan japonicaus Hara. J. Chem. Soc., Chem. Commun., 319-320.
12. Y. Fujimoto, Y. Ikuina, M. Nagakari, K. Kakinuma, and N. Ikekawa (1990) C-25 Prochirality in the Fragmentation Reaction Catalysed by Fucosterol Epoxide Lyase from the Silkworm, Bombyx mori. J. Chem. Soc., Perkin Trans. 1, 2041-2046.
13. 24(28)-Ethylidene Sterols: Studies on the Recombinant Phytosterol Methyl Transferase from Arabidopsis thaliana. Tetrahedron Lett., 38, 6115-6118.
14. δ:37.3 (C-1), 31.7 (J=35.8 Hz, C-2), 71.8 (J=35.8 Hz, C-3), 42.3 (C-4), 140.8 (J=64.8 Hz, C-5), 121.7 (J=64.8 Hz, C-6), 31.9 (C-7), 31.9 (C-8), 50.2 (J=35.8 Hz, C-9), 36.5 (J=35.8 Hz, C-10), 21.1 (J=35.8 Hz, C-13), 56.8 (C-14), 24.3 (C-15), 28.2 (J=34.1 Hz, C-16), 56.0 (J=34.1 Hz, C-17), 11.9 (C-18), 19.4 (J=35.8 Hz, C-19), 36.2 (J=37.5 Hz, C-20), 18.8 (37.5 Hz, C-21), 36.0 (C-22), 27.9 (J=42.6 Hz, C-23), 145.88 (J=42.6 Hz, C-24), 116.5 (C-28), 12.8 (C-29). Signals listed with J value were accompanied by a satellite doublet.