RSS-Feed abonnieren
DOI: 10.1055/s-2003-39713
Antimicrobial Diterpenes from the Seeds of Cephalotaxus harringtonia var. drupacea
Publikationsverlauf
Received: September 27, 2002
Accepted: January 25, 2003
Publikationsdatum:
12. Juni 2003 (online)
Abstract
Six diterpenes, including two new natural products, were isolated from the seeds of Cephalotaxus harringtonia. The new metabolites were characterised as 8β-hydroxy-9(11),13-abietadien-12-one and 5,6-didehydroferruginol, while the known compounds were identified as ferruginol, sugiol, 6,12-dihydroxyabieta-5,8,11,13-tetraen-7-one, and abieta-8,11,13-trien-7β-ol. These compounds were studied in vitro for their antimicrobial activity against clinically isolated bacteria and Candida strains. Ferruginol and 6,12-dihydroxyabieta-5,8,11,13-tetraen-7-one showed antimicrobial activity against Gram-positive bacteria. None of the six diterpenes was active against the Gram-negative organisms and yeasts tested.
References
-
1 Huang L, Xue Z.
Cephalotaxus Alkaloids. In: Brossi A, ed
The Alkaloids Chemistry and Pharmacology . Vol. XXIII New York; Academic Press 1984: pp. 157-226 - 2 Yang Z, Kitano Y, Chiba K, Shibata N, Kurokawa H, Doi Y, Arakawa H, Tada M. Synthesis of various oxidized abietane diterpenes and their antibacterial activities against MRSA and VRE. Bioorganic & Medicinal Chemistry. 2001; 9 347-56
- 3 Evans G B, Furneaux R H, Gravestock M B, Lynch G P, Scott G K. The synthesis and antibacterial activity of totarol derivatives. Part 1: modification of ring C and pro-drugs. Bioorganic & Medicinal Chemistry. 1999; 7 1953-64
- 4 Ulubelen A, Öksuz S, Kolak U, Bozok-Johansson C, Celik C, Voelter W. Antibacterial diterpenes from the roots of Salvia viridis . Planta Medica. 2000; 66 458-62
- 5 Fukui H, Koshimizu K, Egawa H. A new diterpene with antimicrobial activity from Chamaecyparis pisifera Endle. Agricultural and Biological Chemistry. 1978; 42 1419-23
- 6 Matsumoto T, Ohsuga Y, Harada S, Kukui K. Synthesis of taxodione, royleanone, cryptojaponol, and methyl 11-hydroxy-12-methoxy-7-oxabieta-8,11,13-trien-18-oate. Bulletin of the Chemical Society of Japan. 1977; 50 266-72
- 7 Burnell R H, Jean M, Poirier D. Synthesis of taxodione. Canadian Journal of Chemistry. 1987; 65 775-81
- 8 Miguel Del Corral J M, Gordaliza M, Salinero M A, San Feliciano A. 13C-NMR data for abieta-8,11,13-triene diterpenoids. Magnetic Resonance in Chemistry. 1994; 32 774-81
- 9 Burnell R H, Jean M. The introduction of oxygen functions into the B ring in synthetic diterpenes. Synthetic Communications. 1984; 14 1229-37
- 10 Joland S D, Hoffmann J J, Schram K H, Cole J R. A new diterpene from Cupressus govenia var. abramasiana: 5β-hydroxy-6-oxasugiol (cupresol). Journal of Natural Products. 1984; 47 983-7
- 11 Fang J M, Lee C K, Cheng Y S. Diterpenes from leaves of Juniperus chinensis . Phytochemistry. 1993; 33 1169-72
- 12 Su W C, Fang J M, Cheng Y S. Abietanes and kauranes from leaves of Criptomeria japonica . Phytochemistry. 1994; 35 1279-84
-
13 Connolly J D, Hill R A. Dictionary of Terpenoids. Vol. 2
Di- and higher terpenoids . London; Chapman & Hall 1991
Prof. Gabriela Mazzanti
Dipartimento di Farmacologia delle Sostanze Naturali e Fisiologia Generale
Università di Roma ”La Sapienza”
Piazzale Aldo Moro 5
00185 Roma
Italy
Fax: +39-06-49912480
eMail: gabriela.mazzanti@uniroma1.it