Summary
A new sesquiterpene alcohol, 12-hydroxy-E-γ-bisabolene, is reported from an undescribed Caribbean sea whip of the genusPseudopterogorgia. The structure of this new alcohol was established based upon spectral analyses and through chemical interconversions.
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Bandurraga, M. M., Fenical, W., Donovan, S. F., and Clardy, J., J. Am. chem. Soc.104 (1982) 6463.
Izac, R. R., Bandurraga, M. M., Wasylyk, J. M., Dunn, F. W., and Fenical, W., Tetrahedron38 (1982) 301.
We thank Frederick M. Bayer, Smithsonian Institution, for his taxonomic advice withPseudopterogorgia species.
Other physical and spectral features for alcohol2 include: oil, UV λmax (MeOH)=250 nm (ω=4900), IR (CHCl3):3350–3450, 2960, 2930, 1715, 1670, 1450, 1380 cm−1, HRMS: M+ m/z obsd. 219.1746 (M+-H, 25.5), C15H23O requires 219.1749, 201.1633 M+-H3O, C15H21O, 13).
Compound3 exhibited the following spectral characteristics: (IR (CHCl3): 2940, 1720, 1670, 1510, 1420, 1380, 1210 cm−1, LRMS: M+, m/z 262 for C17H26O2;1H NMR (360 MHz, CCl4): σ 5.50 (1 H, bs), 5.37 (1 H, bs), 4.44 (2 H, bs), 2.72 (2 H, bs), 2.30 (2 H, bt), 2.08 (3 H, s), 2.11 (4 H, bs), 2.08 (3 H, s), 1.98 (2 H, bt), 1.67 (9 H, s).
Compound4 exhibited the following spectral characteristics: UV: λmax (MeOH)=247 nm (ω=2200), IR (CHCl3): 2960, 1720, 1450, 1360 cm−1, LRMS: M+, m/z (relative intensity) 260 (0.3) for C17H24O2, 200 (M+-HOAc, 5), 158 (6), 145 (11), 143 (22), 132 (37),1H NMR (360 MHz, CDCl3): σ 7.11 (4 H, m), 5.42 (1 H, bt), 4.43 (2 H, bs), 2.67 (1 H, m), 2.32 (3 H, s), 2.09 (3 H, s), 1.59 (3 H, s), 1.22 (3 H, d, J=6.9 Hz).
Epoxide5 exhibited the following spectral characteristics: IR (CHCl3): 3410, 2980, 2950, 2920, 1430, 1370 cm−1, LRMS: M+, m/z 236 for C20H24O2, 218 (M+-H2O);1H NMR (360 MHz, CDCl3): σ 5.42 (1 H, bt), 5.36 (1 H, bs), 4.00 (2 H, bs), 2.38 (1 H, bs), 2.33 (1 H, bs), 2.16 (2 H, m), 2.04 (2 H, m), 1.76 (2 H, m), 1.70 (3 H, s), 1.68 (3 H, s), 1.62 (2 H, m), 1.33 (3 H, s).
Compound6 exhibited the following spectral characteristics: IR (CHCl3): 3300 (brd), 2920, 1715, 1350 cm−1, LRMS: M+, m/z 124 for C8H12O (M+-H2O);1H NMR (360 MHz, CDCl3): σ 5.37 (1 H, bt), 4.00 (2 H, bs), 2.51 (2 H, t), 2.32 (2 H, t), 2.15 (3 H, s), 1.68 (3 H, s).
The reported values for C7, C11 and C14 forE-ψ-bisabolene are 29.7, 27.4 and 18.4 ppm. TheZ isomer shows resonances at 26.8, 29.4 and 17.8 ppm12·Since2 shows bands at 29.9, 27.2 and 18.4 ppm it is assumed to be theE isomer.
Izac, R. R., Ph. D. Thesis, University of California, Riverside 1978.
McEnroe, F. J., and Fenical, W., Tetrahedron34 (1978) 1661.
Ciereszko, L. S., and Karns, T. K. B., in: Biology and Geology of Coral Reefs, vol. II, Biology 1, p. 183. Eds O. A. Jones and R. Endean. Academic Press, New York 1973.
Jeffs, P. W., and Lytle, L. T., Lloydia37 (1974) 315.
Weinheimer, A.J., Schmitz, F. J., and Ciereszko, L. S. in: Drugs from the Sea; Trans. Drugs from the Sea Symp., p. 135. Mar. Technol. Soc., Washington, DC 1967.
Gerhart, D. J., Biol. Bull.164, (1983) 71.
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Acknowledgment. This research was supported by NOAA, Office of Sea Grant, Department of Commerce, under grant NA80AA-D-00120, and in part by the California State Resources Agency, project R/MP-22. The U.S. Government is authorized to reproduce and distribute reprints. We wish to acknowledge the mass spectral support provided by the Bioorganic Biomedical Mass Spectrometry Resource Center, University of California, San Francisco (A.L. Burlingame, Director) which is supported through NIH grant RR00719.
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Look, S.A., Buchholz, K. & Fenical, W. 12-Hydroxy-E-γ-bisabolene, a new sesquiterpene alcohol from a Caribbean sea whip of the genusPseudopterogorgia (Gorgonacea, Cnidaria). Experientia 40, 931–933 (1984). https://doi.org/10.1007/BF01946443
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DOI: https://doi.org/10.1007/BF01946443