Skip to main content
Elsevier - PMC COVID-19 Collection logoLink to Elsevier - PMC COVID-19 Collection
. 2001 Feb 1;51(16):4571–4618. doi: 10.1016/0040-4020(95)00216-U

The natural products chemistry of West Indian gorgonian octocorals

Abimael D Rodríguez 1
PMCID: PMC7131365  PMID: 32287414

The content is available as a PDF (2.4 MB).

References

References and notes

  • 1.Bayer F.M. Martinus Nijhoff; The Hague: 1961. The Shallow-Water Octocorallia of the West Indian Region. [Google Scholar]
  • 2.Ciereszko L.S. In: Comparative Biochemistry of Nitrogen Metabolism. Campbell J.W., editor. Academic Press; New York: 1970. pp. 57–65. [Google Scholar]
  • 3.Ciereszko L.S., Karns T.K.B. In: Biology and Geology of Coral Reef. Jones O.A., Endean R., editors. Academic Press; New York: 1973. pp. 183–203. [Google Scholar]
  • 4.Fenical W. In: Scheuer P.J., editor. Vol II. Academic Press; New York: 1978. pp. 173–245. (Marine Natural Products Chemistry, Chemical and Biological Perspectives). [Google Scholar]
  • 5.Tursch B., Braekman J.C., Daloze D., Kaisin M. In: Marine Natural Products Chemistry, Chemical and Biological Perspectives. Scheuer P.J., editor. Academic Press; New York: 1978. pp. 247–296. [Google Scholar]
  • 6.Weinheimer A.J., Chang C.W.J., Matson J.A. Fortschr. Chem. Org. Naturst. 1979;36:285–387. [Google Scholar]
  • 7.Faulkner D.J. Nat. Prod. Rep. 1993;10:497–539. doi: 10.1039/np9931000497. [DOI] [PubMed] [Google Scholar]; Faulkner D.J. Nat. Prod. Rep. 1992;9:323–364. [Google Scholar]; Faulkner D.J. Nat. Prod. Rep. 1991;8:97–147. doi: 10.1039/np9910800097. [DOI] [PubMed] [Google Scholar]; Faulkner D.J. Nat. Prod. Rep. 1990;7:269–309. doi: 10.1039/np9900700269. [DOI] [PubMed] [Google Scholar]; Faulkner D.J. Nat. Prod. Rep. 1988;5:613–663. doi: 10.1039/np9880500613. [DOI] [PubMed] [Google Scholar]; Faulkner D.J. Nat. Prod. Rep. 1987;4:539–576. doi: 10.1039/np9870400539. [DOI] [PubMed] [Google Scholar]; Faulkner D.J. Nat. Prod. Rep. 1986;3:1–33. doi: 10.1039/np9860300001. [DOI] [PubMed] [Google Scholar]; Faulkner D.J. Nat. Prod. Rep. 1984;1:551–598. [Google Scholar]; Faulkner D.J. Nat. Prod. Rep. 1984;1:251–280. [Google Scholar]
  • 8.Sammarco P.W., Coll J.C. In: Bioorganic Marine Chemistry. Scheuer P.J., editor. Springer-Verlag; Berlin Heidelberg: 1988. pp. 87–116. [Google Scholar]
  • 9.Coll J.C. Chem. Rev. 1992;92:613–631. [Google Scholar]
  • 10.Burkholder P.R., Burkholder L.M. Science. 1958;127:1174–1175. doi: 10.1126/science.127.3307.1174. [DOI] [PubMed] [Google Scholar]
  • 11.Goad L.J. In: Scheuer P.J., editor. Vol II. Academic Press; New York: 1978. pp. 75–172. (Marine Natural Products Chemistry, Chemical and Biological Perspectives). [Google Scholar]
  • 12.Kerr R.G., Baker B.J. Nat. Prod. Rep. 1991;8:465–497. [Google Scholar]
  • 13.Liaaen-Jensen S. In: Scheuer P.J., editor. Vol II. Academic Press; New York: 1978. pp. 1–73. (Marine Natural Products Chemistry, Chemical and Biological Perspectives). [Google Scholar]
  • 14.D'Auria M.V., Minale L., Riccio R. Chem. Rev. 1993;93:1839–1895. [Google Scholar]
  • 15.Joseph J.D. In: Ackman R.G., editor. Vol II. CRC Press Inc; Boca Ratón, Florida: 1989. pp. 70–75. (Marine Biogenic Lipids, Fats, and Oils). [Google Scholar]
  • 16.Weinheimer A.J. In: Food-Drugs from the Sea, Proceedings 1972. Worthen L.R., editor. Marine Technology Society; Washington, D.C: 1973. pp. 359–366. [Google Scholar]
  • 17.Weinheimer A.J., Karns T.K.B. In: Food-Drugs from the Sea, Proceedings 1974. Webber H.H., Ruggieri G.D., editors. Marine Technology Society; Washington, D.C: 1976. pp. 491–496. [Google Scholar]
  • 18.Kaul P.N., Kulkarni S.K., Weinheimer A.J., Schmitz F.J., Karns T.K.B. Lloydia. 1977;40:253–268. [PubMed] [Google Scholar]
  • 19.Weinheimer A.J., Matson J.A., Karns T.K.B., Hossain M.B., Van der Helm D. In: Drugs & Food from the Sea Myth or Reality. Kaul P.N., Sindermann C.J., editors. University of Oklahoma; Norman: 1978. pp. 117–121. [Google Scholar]
  • 20.Ciereszko L.S., Sifford D.H., Weinheimer A.J. Ann. N.Y. Acad. Sci. 1960;90:917–919. doi: 10.1111/j.1749-6632.1960.tb26437.x. [DOI] [PubMed] [Google Scholar]
  • 21.Ciereszko L.S., Odense P.H., Schmidt R.W. Ann. N.Y. Acad. Sci. 1960;90:920–922. doi: 10.1111/j.1749-6632.1960.tb26438.x. [DOI] [PubMed] [Google Scholar]
  • 22.Ciereszko L.S. Trans. N.Y. Acad. Sci. 1962;24:502–503. doi: 10.1111/j.2164-0947.1962.tb01426.x. [DOI] [PubMed] [Google Scholar]
  • 23.Stierle D.B., Carté B., Faulkner D.J., Tagle B., Clardy J. J. Am. Chem. Soc. 1980;102:5088–5092. [Google Scholar]
  • 24.Selover S.J., Crews P., Tagle B., Clardy J. J. Org. Chem. 1981;46:964–970. [Google Scholar]
  • 25.Morales J.J., Lorenzo D., Rodríguez A.D. J. Nat. Prod. 1991;54:1368–1382. doi: 10.1021/np50077a021. [DOI] [PubMed] [Google Scholar]
  • 26.Rodríguez A.D. Magn. Reson. Chem. 1992;30:977–986. [Google Scholar]
  • 27.Tang X., Li Y.J., Morales J.J., Rodríguez A.D. J. Cryst. Spect. Res. 1993;23:641–644. [Google Scholar]
  • 28.Rodríguez A.D., Cóbar O.M. Tetrahedron. 1993;49:319–328. [Google Scholar]
  • 29.Rodríguez A.D., Cóbar O.M., Martínez N. J. Nat. Prod. 1994;57:1638–1655. doi: 10.1021/np50114a005. [DOI] [PubMed] [Google Scholar]
  • 30.Crews P., Klein T.E., Rick Hogue E., Myers B.L. J. Org. Chem. 1982;47:811–815. [Google Scholar]
  • 31.Rodríguez A.D., Cóbar O.M., Martínez N. Tetrahedron Lett. 1994;35:5793–5796. [Google Scholar]
  • 32.Dookran R., Maharaj D., Mootoo B.S., Ramsewak R., McLean S., Reynolds W.F., Tinto W.F. Tetrahedron. 1994;50:1983–1992. [Google Scholar]
  • 33.Burks J.E., Van der Helm D., Chang C.Y., Ciereszko L.S. Acta Cryst. 1977;B33:704–709. [Google Scholar]
  • 34.Maharaj D., Mootoo B.S., Lough A.J., McLean S., Reynolds W.F., Tinto W.F. Tetrahedron Lett. 1992;33:7761–7764. [Google Scholar]
  • 35.Coval S.J., Cross S., Bernardinelli G., Jefford C.W. J. Nat. Prod. 1988;51:981–984. [Google Scholar]
  • 36.Harvell C.D., Fenical W., Roussis V., Ruesink J.L., Griggs C.C., Greene C.H. Mar. Ecol. Prog. Ser. 1993;93:165–173. [Google Scholar]
  • 37.Rodríguez A.D., Cóbar O.M. Tetrahedron. 1995 submitted. [Google Scholar]
  • 38.Grode S.H., James T.R., Cardellina J.H., II Tetrahedron Lett. 1983;24:691–694. [Google Scholar]
  • 39.Grode S.H., James T.R., Jr., Cardellina J.H., II, Onan K.D. J. Org. Chem. 1983;48:5203–5207. [Google Scholar]
  • 40.Cardellina J.H., II, James T.R., Jr., Chen M.H.M., Clardy J. J. Org. Chem. 1984;49:3398–3399. [Google Scholar]
  • 41.Cardellina J.H., II Pure & Appl. Chem. 1986;58:365–374. [Google Scholar]
  • 42.Cardellina J.H., II . In: Biologically Active Natural Products: Potential Use in Agriculture. Cutler H.G., editor. 1988. pp. 305–315. (ACS Symposium Series 380). Washington, D.C. [Google Scholar]
  • 43.Cardellina J.H., II, Raub M.F., VanWagenen B.C. In: Allelochemicals: Role in Agriculture and Forestry. Waller G.R., editor. 1987. pp. 562–571. (ACS Symposium Series 330). Washington, D.C. [Google Scholar]
  • 44.Cardellina J.H., II, Hendrickson R.L., Manfredi K.P., Strobel S.A., Clardy J. Tetrahedron Lett. 1987;28:727–730. [Google Scholar]
  • 45.Brehm M., Dauben W.G., Köhler P., Lichtenthaler F.W. Angew. Chem. Int. Ed. Engl. 1987;26:1271–1273. [Google Scholar]
  • 46.Pordesimo E.O., Schmitz F.J., Ciereszko L.S., Hossain M.B., Van der Helm D. J. Org. Chem. 1991;56:2344–2357. [Google Scholar]
  • 47.Look S.A., Fenical W., Van Engen D., Clardy J. J. Am. Chem. Soc. 1984;106:5026–5027. [Google Scholar]
  • 48.Dookran R., Maharaj D., Mootoo B.S., Ramsewak R., McLean S., Reynolds W.F., Tinto W.F. J. Nat. Prod. 1993;56:1051–1056. [Google Scholar]
  • 49.Pathirana C., Fenical W., Corcoran E., Clardy J. Tetrahedron Lett. 1993;34:3371–3372. [Google Scholar]
  • 50.Huang H., Forsyth C.J. Tetrahedron Lett. 1993;34:7889–7890. [Google Scholar]
  • 51.Fenical W., Pawlik J.R. Mar. Ecol. Prog. Ser. 1991;75:1–8. [Google Scholar]
  • 52.Weinheimer A.J., Matson J.A., Van der Helm D., Poling M. Tetrahedron Lett. 1977:1295–1298. [Google Scholar]
  • 53.Martin G.E., Matson J.A., Weinheimer A.J. Tetrahedron Lett. 1979:2195–2198. [Google Scholar]
  • 54.Still W.C., Mobilio D. J. Org. Chem. 1983;48:4785–4786. [Google Scholar]
  • 55.Kato T., Aoki M., Uyehara T. J. Org. Chem. 1987;52:1803–1810. [Google Scholar]
  • 56.Tius M.A., Fauq A.H. J. Am. Chem. Soc. 1986;108:1035–1039. [Google Scholar]
  • Marshall J.A., Cleary D.G. J. Org. Chem. 1986;51:858–863. [Google Scholar]
  • Marshall J.A., Jenson T.M., DeHoff B.S. J. Org. Chem. 1987;52:3860–3866. [Google Scholar]
  • 58.Shin J., Fenical W. J. Org. Chem. 1988;53:3271–3276. [Google Scholar]
  • 59.Xinhua B., Van der Helm D., Shin J., Fenical W. Acta Cryst. 1992;C48:891–894. doi: 10.1107/s0108270191011241. [DOI] [PubMed] [Google Scholar]
  • 60.Look S.A., Fenical W., Qi-tai Z., Clardy J. J. Org. Chem. 1984;49:1417–1423. [Google Scholar]
  • 61.Shin J., Fenical W. J. Org. Chem. 1991;56:1227–1233. [Google Scholar]
  • 62.Gopichand Y., Schmitz F.J. Tetrahedron Lett. 1978:3641–3644. [Google Scholar]
  • 63.Shin J., Fenical W. J. Org. Chem. 1991;56:3153–3158. [Google Scholar]
  • 64.Iwashima M., Nagaoka H., Kobayashi K., Yamada Y. Tetrahedron Lett. 1992;33:81–82. [Google Scholar]
  • 65.The true source of the dolabellane diterpenoids in reference 66 is not E. calyculata but E. laciniata. This correction has been noted in reference 68. The same correction applies also to reference 67.
  • 66.Look S.A., Fenical W. J. Org. Chem. 1982;47:4129–4134. [Google Scholar]
  • 67.Cáceres J., Rivera M.E., Rodríguez A.D. Tetrahedron. 1990;46:341–348. [Google Scholar]
  • 68.Shin J., Fenical W. J. Org. Chem. 1991;56:3392–3398. [Google Scholar]
  • 69.Rodríguez A.D., Acosta A.L., Dhasmana H. J. Nat. Prod. 1993;56:1843–1849. doi: 10.1021/np50100a031. [DOI] [PubMed] [Google Scholar]
  • 70.Rodríguez A.D., González E., González C. J. Nat. Prod. 1995;58 doi: 10.1021/np50116a010. in press. [DOI] [PubMed] [Google Scholar]
  • 71.Williams D.R., Coleman P.J., Nevill C.R., Robinson L.A. Tetrahedron Lett. 1993;34:7895–7898. [Google Scholar]
  • 72.Mehta G., Karra S.R., Krishnamurthy N. Tetrahedron Lett. 1994;35:2761–2762. [Google Scholar]
  • 73.Weinheimer A.J., Youngblood W.W., Washecheck P.H., Karns T.K.B., Ciereszko L.S. Tetrahedron Lett. 1970:497–500. [Google Scholar]
  • 74.Weinheimer A.J., Schmitz F.J., Ciereszko L.S. In: Drugs from the Sea. Trans. Symp. Freudenthal H.D., editor. Marine Technology Society; Washington, D.C: 1968. pp. 135–140. [Google Scholar]
  • 75.Harirchian B., Bauld N.L. J. Am. Chem. Soc. 1989;111:1826–1828. [Google Scholar]
  • 76.Morales J.J., Espina J.R., Rodríguez A.D. Tetrahedron. 1990;46:5889–5894. [Google Scholar]
  • 77.Rehm S.J. University of Oklahoma; Norman: 1971. (Ph.D. Thesis). [Google Scholar]
  • 78.Ealick S.E., Van der Helm D., Weinheimer A.J. Acta Cryst. 1975;B31:1618–1626. [Google Scholar]
  • 79.Van der Helm D., Ealick S.E., Weinheimer A.J. Cryst. Struct. Comm. 1974;3:167–171. [Google Scholar]
  • 80.Fontán L.A., Yoshida W.Y., Rodríguez A.D. J. Org. Chem. 1990;55:4956–4960. [Google Scholar]
  • 81.Perkins D.L., Ciereszko L.S. J. Protozool. Suppl. 1970;17:20. [Google Scholar]
  • 82.Hadfield M.G., Ciereszko L.S. In: Drugs & Food from the Sea Myth or Reality. Kaul P.N., Sindermann C.J., editors. University of Oklahoma; Norman: 1978. pp. 145–150. [Google Scholar]
  • 83.Lee W.Y., Macko S.A., Ciereszko L.S. J. Exp. Mar. Biol. Ecol. 1981;54:91–96. [Google Scholar]
  • 84.Ciereszko L.S., Guillard R.R.L. J. Exp. Mar. Biol. Ecol. 1989;127:205–210. [Google Scholar]
  • 85.Eterović V.A., Li L., Ferchmin P.A., Lee Y.H., Hann R.M., Rodríguez A.D., McNamee M.G. Cell. Mol. Neurobiol. 1993;13:111–121. doi: 10.1007/BF00735368. [DOI] [PubMed] [Google Scholar]
  • 86.Marshall J.A., Karas L.J., Coghlan M.J. J. Org. Chem. 1982;47:699–701. [Google Scholar]
  • 87.Marshall J.A., Andrews R.C., Lebioda L. J. Org. Chem. 1987;52:2378–2388. [Google Scholar]
  • 88.Fontán L.A., Rodríguez A.D. J. Nat. Prod. 1991;54:298–301. [Google Scholar]
  • 89.Rodríguez A.D., Li Y., Dhasmana H., Barnes C.L. J. Nat. Prod. 1993;56:1101–1113. [Google Scholar]
  • 90.Rodríguez A.D., Piña I.C., Soto J.J., Rojas D.R., Barnes C.L. Can. J. Chem. 1995;58 in press. [Google Scholar]
  • 91.Rodríguez A.D., Soto J.J., Piña I.C. J. Nat. Prod. 1995 doi: 10.1021/np50122a008. submitted. [DOI] [PubMed] [Google Scholar]
  • 92.Archer D.A., Bromidge S.M., Sammes P.G. J. Chem. Soc., Perkin Trans. 1. 1988:3223–3228. [Google Scholar]
  • 93.Most of the cembranolides listed here have actually been attributed to E. mammosa or both E. mammosa and E. succinea. Clearly, these two species of Eunicea are taxonomically complex and thus easily confused with one another. After multiple collections near Puerto Rico, we have found that the presence of 12,13-bisepieupalmerin (152) [or that of its congeners eunicin (143) and jeunicin (145), all of which possess the (12R, 13S) configuration] constitutes a reliable chemotaxonomic tool to identify specimens of E. succinea. Likewise, the presence of eupalmerin acetate (113) [or eupalmerin (116), each having the (12S, 13R) configuration] serves equally well to identify specimens of E. mammosa. Since compounds 113 and 152 have never been found to occur within the same organism, this method may constitute a simple and reliable chemotaxonomic test.
  • 94.Weinheimer A.J., Middlebrook R.E., Bledsoe J.O., Jr., Marsico W.E., Karns T.K.B. J. Chem. Soc., Chem. Commun. 1968:384–385. [Google Scholar]
  • 95.Hossain M.B., Nicholas A.F., Van der Helm D. J. Chem. Soc., Chem. Commun. 1968:385–386. [Google Scholar]
  • 96.Gampe R.T., Jr., Alam M., Weinheimer A.J., Martin G.E., Matson J.A., Willcott M.R., III, Inners R.R., Hurd R.E. J. Am. Chem. Soc. 1984;106:1823–1826. [Google Scholar]
  • 97.Van der Helm D., Enwall E.L., Weinheimer A.J., Karns T.K.B., Ciereszko L.S. Acta Cryst. 1976;B32:1558–1560. [Google Scholar]
  • 98.Sanduja R., Linz G.S., Alam M., Weinheimer A.J., Martin G.E., Ezell E.L. J. Heterocyclic Chem. 1986;23:529–535. [Google Scholar]
  • 99.Weinheimer A.J., Matson J.A., Poling M., Van der Helm D. Acta Cryst. 1982;B38:580–583. [Google Scholar]
  • 100.Gross R.A. University of Oklahoma; Norman: 1974. (Ph.D. Thesis). [Google Scholar]
  • 101.Ciereszko L.S. 1977. Marine Research in Indonesia; pp. 113–118. [Google Scholar]
  • 102.Gupta P.K.S., Hossain M.B., Van der Helm D. Acta Cryst. 1986;C42:434–436. [Google Scholar]
  • 103.Chang C.Y. University of Oklahoma; Norman: 1977. (Ph.D. Thesis). [Google Scholar]
  • 104.Chang C.Y., Ciereszko L.S., Hossain M.B., Van der Helm D. Acta Cryst. 1980;B36:731–733. [Google Scholar]
  • 105.Gopichand Y., Ciereszko L.S., Schmitz F.J., Switzner D., Rahman A., Hossain M.B., Van der Helm D. J. Nat. Prod. 1984;47:607–614. doi: 10.1021/np50034a007. [DOI] [PubMed] [Google Scholar]
  • 106.Eterović V.A., Hann R.M., Ferchmin P.A., Rodríguez A.D., Li L., Lee Y.H., McNamee M.G. Cell. Mol. Neurobiol. 1993;13:99–110. doi: 10.1007/BF00735367. [DOI] [PubMed] [Google Scholar]
  • 107.Rodríguez A.D., Dhasmana H. J. Nat. Prod. 1993;56:564–570. doi: 10.1021/np50094a017. [DOI] [PubMed] [Google Scholar]
  • 108.Shin J., Fenical W. Tetrahedron Lett. 1989;30:6821–6824. [Google Scholar]
  • 109.Shin J., Fenical W. Tetrahedron. 1993;49:9277–9284. [Google Scholar]
  • 110.Shin J., Fenical W., Stout T.J., Clardy J. Tetrahedron. 1993;49:515–524. [Google Scholar]
  • 111.Weinheimer A.J., Washecheck P.H. Tetrahedron Lett. 1969:3315–3318. doi: 10.1016/s0040-4039(00)99750-8. [DOI] [PubMed] [Google Scholar]
  • 112.Ciereszko L.S., Chang C.W.J. J. Chem. Ed. 1978;55:744. [Google Scholar]
  • 113.Van Alstyne K.L., Paul V.J. Coral Reefs. 1992;11:155–159. [Google Scholar]
  • 114.Ksebati M.B., Ciereszko L.S., Schmitz F.J. J. Nat. Prod. 1984;47:1009–1012. doi: 10.1021/np50036a018. [DOI] [PubMed] [Google Scholar]
  • 115.Jeffs P.W., Lytle L.T. Lloydia. 1974;37:315–317. [Google Scholar]
  • 116.Asaoka M., Shima K., Fujii N., Takei H. Tetrahedron. 1988;44:4757–4766. [Google Scholar]
  • 117.Wang Z., Cheng Z. Youji Huaxue. 1993;13:244–249. [Google Scholar]
  • 118.Kelecom A., Brick-Peres M., Fernandes L. J. Nat. Prod. 1990;53:750–752. [Google Scholar]
  • 119.Lasker H.R. Mar. Ecol. Prog. Ser. 1984;19:261–268. [Google Scholar]
  • 120.Ealick S.E., Van der Helm D., Gross R.A., Jr., Weinheimer A.J., Ciereszko L.S. Acta Cryst. 1980;B36:1901–1907. [Google Scholar]
  • 121.Chan W.R., Tinto W.F., Manchand P.S., Todaro L.J., Ciereszko L.S. Tetrahedron. 1989;45:103–106. [Google Scholar]
  • 122.Peniston M., Rodríguez A.D. J. Nat. Prod. 1991;54:1009–1016. [Google Scholar]
  • 123.Takayanagi H., Kitano Y., Morinaka Y. Tetrahedron Lett. 1990;31:3317–3320. [Google Scholar]
  • 124.Takahashi T., Yokoyama H., Haino T., Yamada H. J. Org. Chem. 1992;57:3521–3523. [Google Scholar]
  • 125.Takayanagi H., Kitano Y., Morinaka Y. J. Org. Chem. 1994;59:2700–2706. [Google Scholar]
  • 126.Kodama M., Yoshio S., Yamaguchi S., Fukuyama Y., Takayanagi H., Morinaka Y., Usui S., Fukazawa Y. Tetrahedron Lett. 1993;34:8453–8456. [Google Scholar]
  • 127.Li W., Li Y., Mao J., Li Y. Chin. J. Chem. 1993;11:159–163. [Google Scholar]
  • 128.Weinheimer A.J., Spraggins R.L. Tetrahedron Lett. 1969:5185–5188. doi: 10.1016/s0040-4039(01)88918-8. [DOI] [PubMed] [Google Scholar]
  • 129.Weinheimer A.J. Stud. Trop. Oceanogr. 1974;12:17–21. [Google Scholar]
  • 130.Weinheimer A.J., Spraggins R.L. In: Food-Drugs from the Sea, Proceedings 1969. Youngken H.W., editor. Marine Technology Society; Washington, D.C: 1970. pp. 311–314. [Google Scholar]
  • 131.Schneider W.P., Rhuland L.E., Hamilton R.D., Bundy G.L., Daniels E.G., Lincoln F.H., Pike J.E. In: Food-Drugs from the Sea, Proceedings 1972. Worthen L.R., editor. Marine Technology Society; Washington, D.C: 1973. pp. 151–155. [Google Scholar]
  • 132.Spraggins R.L. In: Food-Drugs from the Sea, Proceedings 1972. Worthen L.R., editor. Marine Technology Society; Washington, D.C: 1973. pp. 157–163. [Google Scholar]
  • 133.Bundy G.L., Schneider W.P., Lincoln F.H., Pike J.E. J. Am. Chem. Soc. 1972;94:2123–2124. doi: 10.1021/ja00761a061. [DOI] [PubMed] [Google Scholar]
  • 134.Schneider W.P., Hamilton R.D., Rhuland L.E. J. Am. Chem. Soc. 1972;94:2122–2123. doi: 10.1021/ja00761a060. [DOI] [PubMed] [Google Scholar]
  • 135.Bundy G.L., Daniels E.G., Lincoln F.H., Pike J.E. J. Am. Chem. Soc. 1972;94:2124. doi: 10.1021/ja00761a062. [DOI] [PubMed] [Google Scholar]
  • 136.Schneider W.P., Bundy G.L., Lincoln F.H., Daniels E.G., Pike J.E. J. Am. Chem. Soc. 1977;99:1222–1232. doi: 10.1021/ja00446a039. [DOI] [PubMed] [Google Scholar]
  • 137.Ciereszko L.S., Gopichand Y., Schmitz F.J., Schneider W.P., Bundy G.L. Experientia. 1985;41:37–38. [Google Scholar]
  • 138.Groweiss A., Fenical W. J. Nat. Prod. 1990;53:222–223. [Google Scholar]
  • 139.Gerhart D.J. Mar. Ecol. Prog. Ser. 1984;19:181–187. [Google Scholar]
  • 140.Gerhart D.J. Biochem. Syst. Ecol. 1986;14:417–421. [Google Scholar]
  • 141.Pawlik J.R., Burch M.T., Fenical W. J. Exp. Mar. Biol. Ecol. 1987;108:55–66. [Google Scholar]
  • 142.Pawlik J.R., Fenical W. Mar. Ecol. Prog. Ser. 1989;52:95–98. [Google Scholar]
  • 143.Corey E.J., Matsuda S.P.T. Tetrahedron Lett. 1987;28:4247–4250. [Google Scholar]
  • 144.Corey E.J., Matsuda S.P.T., Nagata R., Cleaver M.B. Tetrahedron Lett. 1988;29:2555–2558. [Google Scholar]
  • 145.Brash A.R. J. Am. Chem. Soc. 1989;111:1891–1892. [Google Scholar]
  • 146.Baertschi S.W., Brash A.R., Harris T.M. J. Am. Chem. Soc. 1989;111:5003–5005. [Google Scholar]
  • 147.Gerwick W.H. Chem. Rev. 1993;93:1807–1823. [Google Scholar]
  • 148.Gopichand Y., Schmitz F.J. J. Org. Chem. 1980;45:2523–2526. [Google Scholar]
  • 149.The acyclic sesquiterpene ketone 199 was isolated in this laboratory as a colorless liquid from a specimen of Plexaurella grisea collected off the west coast of Puerto Rico near Mona Island. The following spectroscopic data were recorded: IR (neat) 3090, 3028, 2958, 2929, 2872, 1713, 1617, 1464, 1367, 1143, 1061, 1035, 987, 965, 889 cm−1; UV (hexane) λmax = 270 nm (ε 30,000); 1H-NMR (CDCl3; 300 MHz) δ 6.34 (2H, m), 5.97 (1H, d, J = 11.1 Hz), 5.63 (1H, dd, J = 7.5, 15 Hz), 5.15 (1H, d, J = 17.4 Hz), 4.98 (1H, d, J = 10.5 Hz), 2.81 (1H, m), 2.38 (2H, ddd, J = 7.0, 14.1 Hz), 2.23 (2H, d, J = 6.6 Hz), 2.12 (1H, m), 1.81 (3H, s), 1.02 (3H, d, J = 6.9 Hz), 0.87 (6H, d, J = 6.3 Hz); 13C-NMR (CDCl3; 75, MHz) δ 209.45 (s), 141.29 (d), 139.75 (d), 134.12 (s), 131.16 (d), 125.29 (d), 112.05 (t), 52.56 (t), 50.27 (t), 32.88 (d), 24.48 (d), 22.58 (q, X 2C), 20.25 (q), 11.94 (q); LREIMS m/z [M]+ 220 (14%) (C15H24O requires 220), 205 (0.3), 178 (0.1), 163 (2), 135 (9), 121 (16), 120 (27); 107 (15), 105 (37), 93 (51), 92 (11), 91 (59), 85 (49), 79 (37), 77 (50), 65 (15), 57 (100).
  • 150.Weinheimer A.J., Matson J.A. Lloydia. 1975;38:378–382. [PubMed] [Google Scholar]
  • 151.Tanaka T., Funakoshi Y., Uenaka K., Maeda K., Mikamiyama H., Takemoto Y., Maezaki N., Iwata C. Chem. Pharm. Bull. 1994;42:300–305. [Google Scholar]
  • 152.Youngblood W.W. Ph.D. Thesis. University of Oklahoma; Norman: 1969. [Google Scholar]
  • 153.Ramaiah P., Rao A.S. Synth. Commun. 1989;19:931–942. [Google Scholar]
  • 154.Hossain M.B., Van der Helm D. Rec. Trav. Chim. Pays-Bas. 1969;88:1413–1423. [Google Scholar]
  • 155.Rice J.R., Papastephanou C., Anderson D.G. Biol. Bull. 1970;138:334–343. doi: 10.2307/1540217. [DOI] [PubMed] [Google Scholar]
  • 156.Papastephanou C., Anderson D.G. Comp. Biochem. Physiol. 1982;73B:617–624. [Google Scholar]
  • 157.Ciereszko L.S. In: Food-Drugs from the Sea, Proceedings 1974. Webber H.H., Ruggieri G.D., editors. Marine Technology Society; Washington, D.C: 1976. pp. 297–301. [Google Scholar]
  • 158.Martin G.E., Matson J.A., Turley J.C., Weinheimer A.J. J. Am. Chem. Soc. 1979;101:1888–1890. [Google Scholar]
  • 159.Marshall J.A., Royce R.D., Jr. J. Org. Chem. 1982;47:693–698. [Google Scholar]
  • 160.McMurry J.E., Dushin R.G. J. Am. Chem. Soc. 1990;112:6942–6949. [Google Scholar]
  • 161.McMurry J.E., Dushin R.G. J. Am. Chem. Soc. 1989;111:8928–8929. [Google Scholar]
  • 162.Tius M.A., Reddy N.K. Tetrahedron Lett. 1991;32:3605–3608. [Google Scholar]
  • 163.Dauben W.G., Wang T., Stephens R.W. Tetrahedron Lett. 1990;31:2393–2396. [Google Scholar]
  • 164.Perkins D.L., Ciereszko L.S. Hydrobiologia. 1973;42:77–84. [Google Scholar]
  • 165.Perkins D.L., Ciereszko L.S. Vol. 54. 1974. pp. 34–35. (Proc. Okla. Acad. Sci.). [Google Scholar]
  • 166.Rodríguez A.D., Martínez N. Experientia. 1993;49:179–181. doi: 10.1007/BF01989427. [DOI] [PubMed] [Google Scholar]
  • 167.Wasylyk J.M., Martin G.E., Weinheimer A.J., Alam M. J. Nat. Prod. 1989;52:391–394. [Google Scholar]
  • 168.Bandurraga M.M., Fenical W., Donovan S.F., Clardy J. J. Am. Chem. Soc. 1982;104:6463–6465. [Google Scholar]
  • 169.Paquette L.A., Rayner C.M., Doherty A.M. J. Am. Chem. Soc. 1990;112:4078–4079. [Google Scholar]
  • 170.Paquette L.A., Doherty A.M., Rayner C.M. J. Am. Chem. Soc. 1992;114:3910–3926. [Google Scholar]
  • 171.Rayner C.M., Astles P.C., Paquette L.A. J. Am. Chem. Soc. 1992;114:3926–3936. [Google Scholar]
  • 172.Marshall J.A., Robinson E.D. J. Org. Chem. 1990;55:3450–3451. [Google Scholar]
  • 173.Marshall J.A., Wang X. J. Org. Chem. 1991;56:6264–6266. [Google Scholar]
  • 174.Marshall J.A., Wang X. J. Org. Chem. 1992;57:3387–3396. [Google Scholar]
  • 175.Marshall J.A., Yu B. J. Org. Chem. 1994;59:324–331. [Google Scholar]
  • 176.Marshall J.A., DuBay W.J. J. Org. Chem. 1994;59:1703–1708. [Google Scholar]
  • 177.Look S.A., Buchholz K., Fenical W. Experientia. 1984;40:931–933. doi: 10.1007/BF01946443. [DOI] [PubMed] [Google Scholar]
  • 178.Tinto W.F., Chan W.R., Reynolds W.F., McLean S. Tetrahedron Lett. 1990;31:465–468. [Google Scholar]
  • 179.Paquette L.A., Astles P.C. Tetrahedron Lett. 1990;31:6505–6508. [Google Scholar]
  • 180.Paquette L.A. Chemtracts: Org. Chem. 1992;5:141–157. [Google Scholar]
  • 181.Chan W.R., Tinto W.F., Laydoo R.S., Machand P.S., Reynolds W.F., McLean S. J. Org. Chem. 1991;56:1773–1776. [Google Scholar]
  • 182.Paquette L.A., Astles P.C. J. Org. Chem. 1993;58:165–169. [Google Scholar]
  • 183.Astles P.C., Paquette L.A. Synlett. 1992:444–446. [Google Scholar]
  • 184.Tinto W.F., Lough A.J., Reynolds W.F., McLean S. Tetrahedron Lett. 1991;32:4661–4664. [Google Scholar]
  • 185.Tinto W.F., John L., Reynolds W.F., McLean S. Tetrahedron. 1991;47:8679–8686. [Google Scholar]
  • 186.McLean S., Reynolds W.F., John L.M.D., Tinto W.F. Magn. Reson. Chem. 1992;30:362–363. [Google Scholar]
  • 187.Ito M., Hirata Y., Shibata Y., Tsukida K. J. Chem. Soc., Perkin Trans. 1. 1990:197–199. [Google Scholar]
  • 188.Ito M., Yamano Y., Shibata Y. Methods Enzymol. 1992;213:13–22. [Google Scholar]
  • 189.Yamano Y., Ito M. J. Chem. Soc., Perkin Trans. 1. 1993:1599–1610. [Google Scholar]
  • 190.John L.M.D., Tinto W.F., McLean S., Reynolds W.F. J. Nat. Prod. 1993;56:144–146. [Google Scholar]
  • 191.Harvell C.D., Fenical W., Greene C.H. Mar. Ecol. Prog. Ser. 1988;49:287–294. [Google Scholar]
  • 192.Harvell C.D., Fenical W. Limnol. Oceanogr. 1989;34:382–389. [Google Scholar]
  • 193.Weinheimer A.J., Washecheck P.H., Van der Helm D., Hossain M.B. J. Chem. Soc., Chem. Commun. 1968:1070–1071. [Google Scholar]
  • 194.Rivero R.B., Pérez A.R., Castro H.V., Argilagos C.S., Henriquez R.D. Z. Naturforsch. 1990;45B:1571–1572. [Google Scholar]
  • 195.Koft E.R., Broadbent T.A. Org. Prep. Proced. Int. 1988;20:199–204. [Google Scholar]
  • 196.Plamondon J., Canonne P. Tetrahedron Lett. 1991;32:589–592. [Google Scholar]
  • 197.Weinheimer A.J., Metzner E.K., Mole M.L., Jr. Tetrahedron. 1973;29:3135–3136. [Google Scholar]
  • 198.Izac R., Bandurraga M.M., Wasylyk J.M., Dunn F.W., Fenical W. Tetrahedron. 1982;38:301–304. [Google Scholar]
  • 199.Chan W.R., Tinto W.F., Moore R. Tetrahedron. 1990;46:1499–1502. [Google Scholar]
  • 200.Fenical W. J. Nat. Prod. 1987;50:1001–1008. doi: 10.1021/np50054a001. [DOI] [PubMed] [Google Scholar]
  • 201.Wright A.E., Burres N.S., Schulte G.K. Tetrahedron Lett. 1989;30:3491–3494. [Google Scholar]
  • 202.Culver P., Burch M., Potenza C., Wasserman L., Fenical W., Taylor P. Mol. Pharmacol. 1985;28:436–444. [PubMed] [Google Scholar]
  • 203.Abramson S.N., Trischman J.A., Tapiolas D.M., Harold E.E., Fenical W., Taylor P. J. Med. Chem. 1991;34:1798–1804. doi: 10.1021/jm00110a007. [DOI] [PubMed] [Google Scholar]
  • 204.Groebe D.R., Dumm J.M., Abramson S.N. J. Biol. Chem. 1994;269:8885–8891. [PubMed] [Google Scholar]
  • 205.Abramson S.N., Culver P., Kline T., Li Y., Guest P., Gutman L., Taylor P. J. Biol. Chem. 1988;263:8568–8573. [PubMed] [Google Scholar]
  • 206.Abramson S.N., Fenical W., Taylor P. Drug Develop. Res. 1991;24:297–312. [Google Scholar]
  • 207.Astley M.P., Pattenden G. Synthesis. 1992;101-105 [Google Scholar]
  • 208.Look S.A., Fenical W., Matsumoto G.K., Clardy J. J. Org. Chem. 1986;51:5140–5145. [Google Scholar]
  • 209.Look S.A., Fenical W., Jacobs R.S., Clardy J. Vol. 83. 1986. pp. 6238–6240. (Proc. Natl. Acad. Sci. USA). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 210.Ettouati W.S., Jacobs R.S. Mol. Pharmacol. 1987;31:500–505. [PubMed] [Google Scholar]
  • 211.Broka C.A., Chan S., Peterson B. J. Org. Chem. 1988;53:1584–1586. [Google Scholar]
  • 212.Corey E.J., Carpino P. J. Am. Chem. Soc. 1989;111:5472–5474. [Google Scholar]
  • 213.Corey E.J., Carpino P. Tetrahedron Lett. 1990;31:3857–3858. [Google Scholar]
  • 214.Look S.A., Fenical W. Tetrahedron. 1987;43:3363–3370. [Google Scholar]
  • 215.Cowin L.M., Massy-Westropp R.A. J. Nat. Prod. 1992;55:1790–1794. [Google Scholar]
  • 216.Harvis C.A., Burch M.T., Fenical W. Tetrahedron Lett. 1988;29:4361–4364. [Google Scholar]
  • 217.Roussis V., Wu Z., Fenical W. J. Org. Chem. 1990;55:4916–4922. [Google Scholar]
  • 218.Ganguly A.K., McCombie S.W., Cox B., Lin S., McPhail A.T. Pure & Appl. Chem. 1990;62:1289–1291. [Google Scholar]
  • 219.McCombie S.W., Cox B., Lin S.I., Ganguly A.K., McPhail A.T. Tetrahedron Lett. 1991;32:2083–2086. [Google Scholar]
  • 220.McCombie S.W., Cox B., Ganguly A.K. Tetrahedron Lett. 1991;32:2087–2090. [Google Scholar]
  • 221.Look S.A., Burch M.T., Fenical W., Qi-tai Z., Clardy J. J. Org. Chem. 1985;50:5741–5746. [Google Scholar]
  • 222.Marshall J.A., Nelson D.J. Tetrahedron Lett. 1988;29:741–744. [Google Scholar]
  • 223.McEnroe F.J., Fenical W. Tetrahedron. 1978;34:1661–1664. [Google Scholar]
  • 224.Tanaka J., Nobutani K., Adachi K. Nippon Kagaku Kaishi. 1988;7:1065–1073. [Google Scholar]
  • 225.Ono M., Yamamoto Y., Todoriki R., Akita H. Heterocycles. 1994;37:181–185. [Google Scholar]
  • 226.Schmitz F.J., Ciereszko L.S., Sifford D.H., Weinheimer A.J. Tetrahedron Lett. 1966:97–104. [Google Scholar]
  • 227.Larson G.L., Betancourt de Pérez R.M. J. Org. Chem. 1985;50:5257–5260. [Google Scholar]
  • 228.Podraza K.F., Sneden A.T. J. Nat. Prod. 1985;48:792–795. [Google Scholar]
  • 229.Trost B.M., Müller T.J.J. J. Am. Chem. Soc. 1994;116:4985–4986. [Google Scholar]
  • 230.Schmitz F.J., Lorance E.D., Ciereszko L.S. J. Org. Chem. 1969;34:1989–1990. [Google Scholar]
  • 231.Pawlik J.R., Fenical W. Mar. Ecol. Prog. Ser. 1992;87:183–188. [Google Scholar]
  • 232.Rodríguez A.D., Ramírez C. J. Nat. Prod. 1994;57:339–347. doi: 10.1021/np50105a002. [DOI] [PubMed] [Google Scholar]
  • 233.Schmitz F.J., Lorance E.D. J. Org. Chem. 1971;36:719–721. [Google Scholar]
  • 234.Schmitz F.J., Lorance E.D., Ciereszko L.S. In: Food-Drugs from the Sea, Proceedings 1969. Youngken H.W., editor. Marine Technology Society; Washington, D.C: 1970. pp. 315–318. [Google Scholar]
  • 235.Fenical, W., Scripps Institution of Oceanography, University of California, San Diego, personal communication, 1994.

Articles from Tetrahedron are provided here courtesy of Elsevier

RESOURCES