An Improved Synthesis of 7, 8-Epoxy-1,3,11-cembratriene-15R(α), 16-diol, a Cembranoid of Marine Origin with a Potent Cancer Chemopreventive Activity
Abstract
:Introduction
Results and Discussion
Conclusions
Experimental
General
Materials
Chemopreventive activity
Synthesis of 7, 8-epoxy-1,3,11-cembratriene-15R(α)-16-diol (7)
Concentration | 3 | 4 | Sarcophytol-A | 5 | 6 |
---|---|---|---|---|---|
32.0 nmol/mL | 14.2 | 12.7 | 11.7 | 5.9 | 3.6 |
16.0 nmol/mL | 62.8 | 60.8 | 60.4 | 55.8 | 52.4 |
3.20 nmol/mL | 81.3 | 78.2 | 79.1 | 74.6 | 71.3 |
0.32 nmol/mL | 100 | 96.0 | 97.3 | 93.8 | 90.6 |
Compound | Concentration | |||
---|---|---|---|---|
32 nmol/mL | 16 nmol/mL | 3.2 nmol/mL | 0.32 nmol/mL | |
7 | 5.0a(60b) | 38.4(>80) | 71.2(>80) | 93.6(>80) |
Sarcophytol-Ac | 8.5(60) | 40.7(>80) | 73.9 (>80) | 97.0(>80) |
- Sample Availability: Samples are available from the authors.
References and Notes
- Haefner, B. Drugs from the Deep: Marine Natural Products as Drug Candidates. Drug Discovery Today 2003, 8, 536–544. [Google Scholar]
- Fujiki, H.; Suganuma, M.; Takagi, K.; Nishiwaki, S.; Yoshizawa, S.; Okabe, S.; Yatsunami, J.; Frenkel, K.; Troll, W.; Marshall, J. A.; Tius, M. A. Sarcophytol A and its Analogs. Cancer Preventive Activity in Phenolic Compounds in Food and their Effects on Health II. Antioxidants & Cancer Prevention. Huang, M-T, Ho, C-T, Lee, C.Y., Eds.; In ACS Symp. Series 507; American Chemical Society: Washington DC, 1992; pp. 380–387. [Google Scholar]
- Fujiki, H.; Suganuma, M.; Komori, A.; Yatsunami, J.; Okabe, S.; Ohta, T.; Sueoka, E. A New Tumor Promotion Pathway and its Inhibitors. Cancer Det. Prev 1994, 18, 1–7. [Google Scholar]
- Steele, V.E.; Moon, R.C.; Lubet, R.A.; Grubbs, C.J.; Reddy, B.S.; Wargovich, M.; McCormick, D.L.; Pereira, M.A.; Crowell, J.A. Preclinical Efficacy Evaluation of Potential Chemopreventive Agents in Animal Carcinogenesis Models; Methods and Results from the NCI Chemoprevention Drug Development Program. J. Cell. Biochem 1994, suppl 20, 32–54. [Google Scholar]
- Ne'eman, I.; Fishelson, L.; Kashman, Y. Sarcophine, A New Toxin from the Soft Coral Sarcophyton Glaucum (Alcyonaria). Toxicon 1974, 12, 593–598. [Google Scholar]
- Katsuyama, I.; Fahmy, H.; Zjawiony, J. K.; Sherief, I. K.; Kilada, R.W; Konoshima, T.; Takasaki, M.; Tokuda, H. Semisynthesis of New Sarcophine Derivatives with Chemopreventive Activity. J. Nat. Prod 2002, 65, 1809–1814. [Google Scholar]
- Takasaki, M.; Konoshima, T.; Komatsu, K.; Tokuda, H.; Nishino, H. Anti-tumor-promoting activity of lignans from the aerial part of Saussurea medusa. Cancer Lett 2000, 158, 53–59. [Google Scholar]
- Czarkie, D.; Carmely, S; Groweiss, A.; Kashman, Y. Attempted Acid-Catalyzed Transannular Reactions in the Cembranoids. Tetrahedron 1985, 41, 1049–1056. [Google Scholar]
© 2004 by MDPI Reproduction is permitted for noncommercial purposes.
Share and Cite
Fahmy, H.; Khalifa, S.I.; Konoshima, T.; Zjawiony, J.K. An Improved Synthesis of 7, 8-Epoxy-1,3,11-cembratriene-15R(α), 16-diol, a Cembranoid of Marine Origin with a Potent Cancer Chemopreventive Activity. Mar. Drugs 2004, 2, 1-7. https://doi.org/10.3390/md201001
Fahmy H, Khalifa SI, Konoshima T, Zjawiony JK. An Improved Synthesis of 7, 8-Epoxy-1,3,11-cembratriene-15R(α), 16-diol, a Cembranoid of Marine Origin with a Potent Cancer Chemopreventive Activity. Marine Drugs. 2004; 2(1):1-7. https://doi.org/10.3390/md201001
Chicago/Turabian StyleFahmy, Hesham, Sherief I. Khalifa, Takao Konoshima, and Jordan K. Zjawiony. 2004. "An Improved Synthesis of 7, 8-Epoxy-1,3,11-cembratriene-15R(α), 16-diol, a Cembranoid of Marine Origin with a Potent Cancer Chemopreventive Activity" Marine Drugs 2, no. 1: 1-7. https://doi.org/10.3390/md201001