Advertisement

Chemical and Biological Aspects of Marine Monoterpenes

  • S. Naylor
  • F. J. Hanke
  • L. V. Manes
  • P. Crews
Part of the Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products book series (FORTCHEMIE (closed), volume 44)

Abstract

The earliest studies on monoterpenes date back to the 1800’s. Nevertheless, this area remains of current interest since monoterpenes are abundant in volatile plant and seaweed oils (1). As the simplest terpenoids, monoterpenes are formed by the dimerization of isoprene (C5) equivalents, and have carbon skeletons which are subdivided into regular or rearranged isoprene types (2). In spite of such a simple genesis, about ten different carbon frameworks had been identified by 1920, and by 1972 they included 30 from a pool of more than 400 compounds (3). In recent years the study of monoterpenes has attracted the attention of diverse groups ranging from organic chemists to ecologists (4–7). Not surprisingly, the monoterpene literature includes reviews on their biochemistry, biosynthesis, synthesis, or structure determination (1–4, 8–11).

Keywords

Digestive Gland Biological Aspect Marine Natural Product Tetrahedron Letter Absolute Stereochemistry 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Mayo, P. DE: Mono- and Sesquiterpenoids. In: The Chemistry of Natural Products, Vol. II, pp. 1–179 ( K. W. Bratley, ed.). New York: Interscience. 1959.Google Scholar
  2. 2.
    Ruzicka, L.: History of the Isoprene Rule. Proc. Chem. Soc. 341 (1959).Google Scholar
  3. 3.
    Devon, T. K., and A. I. Scott: Handbook of Naturally Occurring Compounds. Vol. II, p. 576. New York: Academic Press. 1972.Google Scholar
  4. 4.
    Cavill, G. W. K.: Insect Terpenoids and Nepetalactone. In: Cyclopentanoid Terpene Derivatives, pp. 203–235 ( W. I. Taylor and A. R. Battersby, eds.). New York: Marcel Dekker. 1969.Google Scholar
  5. 5.
    Halligan, J. P.: Toxic Terpenes from Artemisia californica. Ecology 56, 999 (1975).CrossRefGoogle Scholar
  6. 6.
    Bowers, W. S.: Insect Juvenile Hormones and Pheromones of Isopentenoid Biogenesis. Lipids 13, 736 (1978).CrossRefGoogle Scholar
  7. 7.
    Epstein, W. W., and L. A. Gaudioso: A Non-head-to-tail Monoterpenoid with a New Skeletal System from Artemisia tridentata rothrockii. J. Org. Chem. 47, 175 (1982).CrossRefGoogle Scholar
  8. 8.
    Francis, M. J. O.: Monoterpene Biosynthesis. In: Aspects of Terpenoid Chemistry and Biochemistry, pp. 29–448 ( T. W. Goodwin, ed.). New York: Academic Press. 1971.Google Scholar
  9. 9.
    Poulter, C. D., and H. C. Rilling: The Prenyl Transfer Reaction. Enzymatic and Mechanism Studies of the 1–4 Coupling Reaction in the Terpene Biosynthetic Pathway. Accounts Chem. Res. 11, 307 (1978).CrossRefGoogle Scholar
  10. 10.
    Loomis, W. D.: Biosynthesis and Metabolism of Monoterpenes. In: Terpenoids in Plants, pp. 59–80 (J. B. Pridham, ed.). New York: Academic Press. 1967, and references therein.Google Scholar
  11. 11.
    Whittaker, D.: The Monoterpenes. IN: Chemistry ofTerpenes and Terpenoids, pp. 11–82 (A. A. Newman, ed.). New York: Academic Press. 1972.Google Scholar
  12. 12.
    Katayama, T.: The Volatile Constituents of Seaweed. III. The Terpenes of Volatile Constituents of U-lva pertusa. Bull. Japan Soc. Sci. Fisheries 21, 412 (1955).CrossRefGoogle Scholar
  13. 13.
    Katayama, T.: Volatile Constituents. In: Physiology and Biochemistry of Algae, pp.467–473 ( R. A. Lewis, ed.). New York: Academic Press. 1962.Google Scholar
  14. 14.
    Faulkner, D. J., and M. O. Stallard: 7-Chloro-3,7-dimethyl-l,4,6-tri-bromo-l-octen- 3-0l, A Novel Monoterpene Alcohol from Aplysia californica. Tetrahedron Letters 1171 (1973).Google Scholar
  15. 15.
    Faulkner, D. J., M. O. Stallard, J. Fayos, and J. Clardy: (3R, 4S,lS)-trans,trans-3,l- dimethyl-l,8,8-tribromo-3,4,7-trichloro-l,5-octadiene, a Novel Monoterpene from the Sea Hare, Aplysia californica. J. Amer. Chem. Soc. 95, 3413 (1973).CrossRefGoogle Scholar
  16. 16.
    Crews, P., and E. Kho: Cartilagineal. An Unusual Monoterpene Aldehyde from Marine Alga. J. Org. Chem. 39, 3303 (1974).CrossRefGoogle Scholar
  17. 17.
    Crews, P.: The Breadth of Monoterpene Synthesis by Marine Red Algae: Potential Difficulties in their Application as Taxonomic Markers. In: Marine Natural Products Chemistry (D. J. Faulkner and W. Fenical, eds.), IV: 1, pp. 211–223. New York: Plenum Press. 1977.CrossRefGoogle Scholar
  18. 18.
    Faulkner, D. J.: Interesting Aspects of Marine Natural Products Chemistry. Tetrahedron 33, 1421 (1977); Natural Organohalogen Compounds. In: The Handbook of Environmental Chemistry ( D. Hutzinger, ed.). Berlin-Heidelberg-New York: Springer. 1980.Google Scholar
  19. 19.
    Moore, R. E.: Marine Aliphatic Natural Products. In: Aliphatic and Related Natural Product Chemistry. Vol. I, pp. 20—67 (F. D. Gunstone, ed.). The Chemical Society. 1979.Google Scholar
  20. 20.
    Christophersen, C., and J. S. Carle: Chemical Signals from a Marine Bryozoan. Naturwiss. 65, 440 (1978).CrossRefGoogle Scholar
  21. 21.
    Ichikawa, N., Y. Naya, and S. Enomoto: Halogenated Monoterpene Derivatives from Desmia (Chondrococcus) japonicus. Proc. Japan Acad. 51, 562 (1975).Google Scholar
  22. 22.
    Siuda, J. F., and J. F. Debarnardis: Naturally Occurring Halogenated Organic Compounds. Lloydia 36, 107 (1973).Google Scholar
  23. 23.
    Andrews, A. G., C. L. Jenkins, M. P. Starr, J. Shepherd, and H. Hope: Structure of Xanthomonadin I. A Novel Dibrominated Aryl-polyene Pigment Produced by the Bacteium Xanthomonas juglandis. Tetrahedron Letters 4023 (1976).Google Scholar
  24. 24.
    Riley, J. P., and R. Chester: Introduction to Marine Chemistry, p. 465. New York: Academic Press. 1971.Google Scholar
  25. 25.
    Fenical, W.: Natural Products Chemistry in the Marine Environment. Science 215, 923 (1982).CrossRefGoogle Scholar
  26. 26.
    Weatherston, J.: The Chemistry of Anthropod Defense Substances. Quart. Rev. 21, 287 (1967).CrossRefGoogle Scholar
  27. 27.
    Dodson, C. H., R. L. Dressler, H. G. Hills, R. M. Adams, and N. H. Williams: Biologically Active Compounds in Orchid Fragrances. Science 164, 1243 (1969).CrossRefGoogle Scholar
  28. 28.
    Hanover, J. W.: Physiology of Tree Resistance to Insects. An. Rev. Entomol. 20, 75 (1975).CrossRefGoogle Scholar
  29. 29.
    Muller, C. H., and C. H. CHOU: Phytotoxins: An Ecological Phase of Phytochemistry. In: Phytochemical Ecology, pp. 201–215 ( J. B. Harborne, ed.). New York: Academic Press. 1972.Google Scholar
  30. 30.
    Paul, J. V., O. J. Mcconnell, and W. Fenical: Cyclic Monoterpenoid Feeding Deterrents from the Red Marine Alga Ochtodes crockeri. J. Org. Chem. 45, 3401 (1980).CrossRefGoogle Scholar
  31. 31.
    Jacobs, R., and P. Crews: Unpublished results.Google Scholar
  32. 32.
    Stallard, M. O., and D.J. Faulkner: Chemical Constituents of the Digestive Gland of the Seahare Aplysia californica — II. portance of Diet. Comp. Biochem. Physiol. 49 B, 25 (1974).Google Scholar
  33. 33.
    Burbott, A. J., and W. D. Loomis: Evidence for Metabolic Turnover of Monoterpenes in Peppermint. Plant Physiol. 44, 173 (1969).CrossRefGoogle Scholar
  34. 34.
    Sandermann, W.: Terpenoids: Structure and Distribution. In: Comparative Biochemistry, Vol. 3, pp. 503–590 ( M. Florkin and H. S. Mason, eds.). New York: Academic Press. 1972.Google Scholar
  35. 35.
    Wehrli, F. W., and T. Nishida: The Use of Carbon-13 Nuclear Magnetic Resonance Spectroscopy in Natural Products Chemistry. Fortschr. Chem. Org. Naturstoffe 36, 1–229 (1979).Google Scholar
  36. 36.
    Sims, J. J., A. F. Rose, and R. R. Izac: Application of 13C-NMR to Marine Natural Products. IN: Marine Natural Products. Chemical and Biological Perspectives, Vol. II, pp. 297–378 (P. J. Scheuer, ed.). New York: Academic Press. 1978.Google Scholar
  37. 37.
    Crews, P., F. J. Hanke, S. Naylor, E. R. Hogue, E. Khzo, and R. Braslau: Halogen Regiochemistry and Substituent Stereochemistry Determination in Marine Monoterpenes by 13C NMR. J. Org. Chem. (In press.)Google Scholar
  38. 38.
    Martin, J. D., and J. Darias: Algal Sesquiterpenoids. In: Marine Natural Products. Chemical and Biological Perspectives, Vol. I, pp. 125–171 ( P. J. Scheuer, ed.). New York: Academic Press. 1978.Google Scholar
  39. 39.
    Fenical, W.: Deterpenoids. In: Marine Natural Products. Chemical and Biological Perspectives, Vol. II, pp. 173–245 ( P. J. Scheuer, ed.). New York: Academic Press. 1978.Google Scholar
  40. 40.
    See Footnote 13 in: Selover, S. J., and P. Crews: Kylinone, a New Sesquiterpene Skeleton from the Marine Alga Laurencia pacifica. J. Org. Chem. 45, 69 (1980).Google Scholar
  41. 41.
    Charlwood, B. V., and D. V. Banthorpe: The Biosynthesis of Monoterpenes. Progr. Phytochem. 5, 65 (1978).Google Scholar
  42. 42.
    Croteau, R.: Biosynthesis of Monoterpenes. In: Biosynthesis of Isoprenoid Compounds, Vol. I, pp. 225—282 ( J. W. Porter and S. L. Spurgeon, eds.). New York: Wiley and Sons. 1981.Google Scholar
  43. 43.
    Theiler, R. F., J. C. Cook, and L. P. Hagar: Halohydrocarbon Synthesis by Bromoperoxidase. Science 202, 1094 (1978).CrossRefGoogle Scholar
  44. 44.
    Hager, L. P., D. R. Morris, F. S. Brown, and H. Eberwein: Chloroperoxidase II. Utilization of Halogen Anions. J. Biol. Chem. 241, 1769 (1966).Google Scholar
  45. 45.
    Pedersen, M.: A Brominating and Hydroxylating Peroxidase from the Red Alga Cystoclonium purpureum. Physiol. Plant 37, 6 (1976).CrossRefGoogle Scholar
  46. 46.
    Theiler, R. F., J. S. Siuder, and L. P. Hager: Bromoperoxidase from the Red Algae Bonnemasisonia hamifera. In: Food and Drugs from the Sea, pp. 153–169 ( P. W. Kaul and C. J. Sindemann, eds.). Oklahoma: University of Oklahoma Press. 1978.Google Scholar
  47. 47.
    Fenical, W.: Molecular Aspects of Halogen-based Biosynthesis of Marine Natural Products. Recent Adv. Phytochem. 13, 214 (1979).Google Scholar
  48. 48.
    Ichikawa, N., Y. Naya, and S. Enomoto: New Halogenated Monoterpenes from Desmia (Chondrococcus) hornemanni. Chem. Lett. (Japan) 1333 (1974).Google Scholar
  49. 49.
    Yoshihara, K., and Y. Hirose: The Derivation of a Brominated Algal Component from Myrcene. Bull. Chem. Soc. (Japan) 51, 653 (1978).CrossRefGoogle Scholar
  50. 50.
    Masaki, Y, K. Hashimoto, K. Sakuma, and K. Kaji: New Ochtodane Syntheses from Myrcene. Tetrahedron Letters 1481 (1982).Google Scholar
  51. 51.
    Mynderse, J. S., D. J. Faulkner, J. Finer,and J. Clardy: (1R, 2S, 4S, 5R)-l-Bromo- /ra 1y-2-chlorovinyl-4,5-dichloro-l,5-dimethyl cyclohexane, a New Monoterpene Skeletal Type from the Red Alga Plocamium violaceum. Tetrahedron Letters 2175 (1975).Google Scholar
  52. 52.
    Higgs, M. D., D. J. Vanderah, and D. J. Faulkner: Polyhalogenated Monoterpenes from Plocamium cartilagineum from the British Coast. Tetrahedron 33, 2775 (1977).CrossRefGoogle Scholar
  53. 53.
    Stierle, D. B., and J. J. Sims: Marine Natural Products — XV. Polyhalogenated Cyclic Monoterpenes from the Red Alga Plocamium cartilagineum of Antarctica. Tetrahedron 35, 1261 (1969).CrossRefGoogle Scholar
  54. 54.
    Stierle, D. B., R. M. Wing, and J. J. Sims: Marine Natural Products XI, Costatone and Costatolide, New Polyhalogenated Monoterpenes from the Red Seaweed Plocamium costatum. Tetrahedron Letters 4455 (1976).Google Scholar
  55. 55.
    Hogberg, H. E., R. H. Thompson, and T. J. King: The Cymopols, A Group of Prenylated Bromohydroquinones from the Green Calcareous Alga Cymopolia barbata. J. Chem. Soc. Perkin I, 1696 (1976).Google Scholar
  56. 56.
    Kho-Wiseman, E.: Natural Products Chemistry of the Red Marine Algae Plocamium violaceum (Farlow) and Plocamium cartilagineum (Dixon). Ph. D. Thesis, University of California, Santa Cruz (1978).Google Scholar
  57. 57.
    Howard, B. M., A. M. Nonomura, and W. Fenical: Chemotaxonomy in Marine Algae. Secondary Metabolite Synthesis by Laurencia in Unialgal Culture. Biochem. Syst. Ecol. 8, 329 (1980).CrossRefGoogle Scholar
  58. 58.
    crews, P., L. campaabell, and E. Heron: Different Chemical Types of Plocamium violaceum (Rhodophyta) from the Monterey Bay Region, California. J. Phycol. 13, 297 (1977).Google Scholar
  59. 59.
    Mynderse, J. S., and D. J. Faulkner: Variations in the Halogenated Monoterpene Metabolites of Plocamium cartilagineum and P. violaceum. Phytochem. 17, 237 (1978).CrossRefGoogle Scholar
  60. 60.
    Fenical, W., and J. N. Norris: Chemotaxonomy in Marine Algae: Chemical Separat ion of Some Laurencia Species (Rhodophyta) from the Gulf of California. J. Phycol. 11, 104 (1975).Google Scholar
  61. 61.
    Abbott, I. A., and G. J. Hollenberg: Marine Algae of California, p. 827. Stanford, Ca.: Stanford University Press. 1973.Google Scholar
  62. 62.
    Dixon, P. S.: Biology of the Rhodophyta, p. 285. Edinburgh: Oliver and Boyd. 1973.Google Scholar
  63. 63.
    Dixon, P. S.: The Typification of Fucus cartilagineus and F. corneus Huds. Blumea 15, 55 (1967).Google Scholar
  64. 64.
    Mynderse, J. S., and D. J. Faulkner: Polyhalogenated Monoterpenes from the Red Alga Plocamium cartilagineum. Tetrahedron 31, 1963 (1975).CrossRefGoogle Scholar
  65. 65.
    Crews, P., and E. Kho-Wiseman: Acyclic Polyhalogenated Monoterpenes from the Red Alga Plocamium violaceum. J. Org. Chem. 42, 2812 (1977).CrossRefGoogle Scholar
  66. 66.
    Fenical, W.: “Chemical Variation in Laurencia pacifica (Kylin) Sesquiterpenes”, unpublished results.Google Scholar
  67. 67.
    Tursch, B.: Some Recent Developments in the Chemistry of Alcyonaceans. Pure Appl. Chem. 48, 1 (1976).Google Scholar
  68. 68.
    Crews, P., E. Kho-Wiseman, and P. Montana: Halogenated Alicyclic Monoterpenes from the Red Alga Plocamium. J. Org. Chem. 43, 116 (1978).CrossRefGoogle Scholar
  69. 69.
    Mcconnell, O. J., and W. Fenical: Ochtodene and Ochtodiol: Novel Polyhalogenated Cyclic Monoterpenes from the Red Seaweed Ochtodes secundiramea. J. Org. Chem, 43, 4238 (1978).CrossRefGoogle Scholar
  70. 70.
    Naya, Y., Y. Hirose, and N. Ichikawa: Labile Halogenated Monoterpenes from Desmia (Chondrococcus) japonicus (Harvey). Chem. Letters (Japan) 839 (1976).Google Scholar
  71. 71.
    Crews, P., P. Ng., E. Kho-Wiseman, and C. Pace: Halogenated Monoterpenes from the Red Alga Microcladia. Phytochem. 15, 1707 (1976).Google Scholar
  72. 72.
    Smith, G. M.: Marine Algae of the Monterey Peninsula, California, p. 752. Stanford, Ca.: Stanford University Press. 1969.Google Scholar
  73. 73.
    Fenical, W.: Personal communication.Google Scholar
  74. 74.
    Oahta, K., and M. Takagi: Halogenated Sesquiterpenes from Marine Red Alga Marginisporum aberrans. Phytochem. 16, 1062 (1977).CrossRefGoogle Scholar
  75. 75.
    Mcmillan, and I. C. Paul: Structures of Halogenated and Antimicrobial Organic Compounds from Marine Sources. In: The Nature of Seawater, pp. 651–666 ( E. D. Goldberg, ed.). Berlin: Abakon Verlagsgesellschaft. 1975.Google Scholar
  76. 76.
    Bates, P., J. W. Blunt, M. P. Hartshorn, A. J. Jones, M. H. G. Munro, W. T. Robinson, and S. C. Yorke: Halogenated Metabolites of the Red Alga Plocamium cruciferum. Aust. J. Chem. 32, 2545 (1979).CrossRefGoogle Scholar
  77. 77.
    Mabry, T. J.: The Chemistry of Geographical Races. Pure Appl. Chem. 34, 377 (1973).Google Scholar
  78. 78.
    Faulkner, D. J., and C. Ireland: The Chemistry of Some Opisthobranch Molluscs. IN: Marine Natural Products Chemistry, Vol. IV: 1, pp. 23–24 (D. J. Faulkner and W. Fenical, eds.). New York: Plenum Press. 1977.CrossRefGoogle Scholar
  79. 79.
    Schulte, G. R., and P. J. Scheuer: Defense Allonomes of Some Marine Molluscs. Tetrahedron 38, 1857 (1982).CrossRefGoogle Scholar
  80. 80.
    Thompson, J. E., R. P. Walker, S. J. Wratten, and D. J. Faulkner: A Chemical Defense Mechanism for the Nudibranch Cadlina luteomarginata. Tetrahedron 38, 1865 (1982).CrossRefGoogle Scholar
  81. 81.
    Imperato, F., L. Minale, and R. Riccio: Constituents of the Digestive Gland of Molluscs of the Genus Aplysia. II. Halogenated Monoterpenes from Aplysia limacina. Experientia 33, 1273 (1977).CrossRefGoogle Scholar
  82. 82.
    Stallard, M. O., and D. J. Faulkner: Chemical Constituents of the Digestive Gland of the Sea Hare Aplysia californica — II. Chemical Transformations. Comp. Biochem. Physiol. 49B, 37 (1974).Google Scholar
  83. 83.
    Ireland, C., M. O. Stallard, D. J. Faulkner, J. Finer, and J. Clardy: Some Chemical Constituents of the Digestive Gland of the Sea Hare Aplysia californica. J. Org. Chem. 41, 2461 (1976).CrossRefGoogle Scholar
  84. 84.
    Hagar, L. P.: Mother Nature Likes Some Halogenated Compounds. Basic Life Sci. 19, 415 (1982).Google Scholar
  85. 85.
    Finer, J., K. Hirotsu, and J. Clardy: X-ray Diffraction and the Structure of Marine Natural Products. In: Marine Natural Products Chemistry, Vol. IV, pp. 147–158 ( D. J. Faulkner and W. Fenical, eds.). New York: Plenum Press. 1977.Google Scholar
  86. 86.
    Crews, P., and E. Kho: Plocamene B, a New Cyclic Monoterpene Skeleton from a Red Marine Alga. J. Org. Chem. 40, 2568 (1975).CrossRefGoogle Scholar
  87. 87.
    Van Engen, D., J. Clardy, E. Kho-Wiseman, P. Crews, M. D. Higgs, and D. J. Faulkner: Violacene: A Reassignment of Structure. Tetrahedron Letters 29 (1978).Google Scholar
  88. 88.
    Woolard, F. X., R. E. Moore, D. van Engen, and J. Clardy: The Structure and Absolute Configuration of Chondrocolactone, a Halogenated Monoterpene from the Red Alga Chondrococcus hornemanni, and a Revised Structure for Chondrocole A. Tetrahedron Letters 2367 (1978).Google Scholar
  89. 89.
    Benyon, J. H.: Mass Spectrometry and Its Applications to Organic Chemistry. New York: Elsevier Publishing Co. 1960.Google Scholar
  90. 90.
    Squillacote, M. E., R. S. Sheridan, O. L. Chapman, and F. A. L. Anet: Planar s-cis- 1,3-butadiene. J. Amer. Chem. Soc. 101, 3657 (1979).CrossRefGoogle Scholar
  91. 91.
    Harris, R. K., and A. V. Cunliffe: Nuclear Magnetic Resonance Studies of 1,3- butadienes. IX — The 1H Spectra of Isoprene and Related Compounds. Org. Mag. Resonance 9, 483 (1977).CrossRefGoogle Scholar
  92. 92.
    Stierle, D. B., R. M. Wing, and J. J. SIMS: Marine Natural Products — XVI. Polyhalogenated Acyclic Monoterpenes from the Red Alga Plocamium of Antarctica. Tetrahedron 35, 2855 (1979).CrossRefGoogle Scholar
  93. 93.
    Mynderse, J. S., and D. J. Faulkner: Violacene, a Polyhalogenated Monocyclic Monoterpene from the Red Alga Plocamium violaceum. J. Amer. Chem. Soc. 96, 6771 (1974).CrossRefGoogle Scholar
  94. 94.
    Norton, R. S., R. G. Warren, and R. J. Wells: Three New Polyhalogenated Monoterpenes from Plocamium species. Tetrahedron Letters 3905 (1977).Google Scholar
  95. 95.
    Burreson, B. J., F. X. Woolard, and R. E. Moore: Chondrocole A and B, Two Halogenated Dimethylhexahydrobenzofurans from the Red Alga Chondrococcus hornemanni (Mertens) Schmitz. Tetrahedron Letters 2155 (1975).Google Scholar
  96. 96.
    Evidence for the Biogenesis of Halogenated Myrcenes from the Red Alga Chondrococcus hornemanni. Chem. Letters (Japan) 1111 (1975).Google Scholar
  97. 97.
    Crews, P.: Monoterpene Halogenated by the Red Alga Plocamium oregonum. J. Org. Chem. 42, 2634 (1977).CrossRefGoogle Scholar
  98. 98.
    Levy, G. C., R. L. Lichter, and G. L. Nelson: Carbon-13 Nuclear Magnetic Resonance Spectroscopy. 2nd Edition, p. 338. Wiley-Interscience. 1980.Google Scholar
  99. 99.
    Crews, P., and E. Kho-Wiseman: Stereochemical Assignments in Marine Natural Products by 13C NMR Gamma Effects. Tetrahedron Letters 2483 (1978).Google Scholar
  100. 100.
    Gonzalez, A. G., J. M. Arteaga, J. D. Martin, M. L. Rodriguez, J. Fayos, and M. Martines-Ripolls: Two New Polyhalogenated Monoterpenes from the Red Alga Plocamium cartilagenium. Phytochem. 17, 947 (1978).CrossRefGoogle Scholar
  101. 101.
    Woolard, F. X., R. E. Moore, M. Mahindran, and A. Sivapalan: (-)-3- Bromomethyl-3-chloro-7-methyl-l,6-octa-Diene from Sri Lankan Chondrococcus hornemanni. Phytochem. 15, 1069 (1976).CrossRefGoogle Scholar
  102. 102.
    Blunt, J. W., M. P. Hartshorn, M. H. G. Munro, and J. C. Yorke: A novel, C8 Dichlorodienol Metabolite of the Red Alga Plocamium cruciferum. Tetrahedron Letters 4417 (1978).Google Scholar
  103. 103.
    Wilcott, M. R., R. E. Davis, D. J. Faulkner, and M. O. Stallard: The Configuration and Conformation of 7-Chloro-l,6-dibromo-3,7-dimethyl-3,4-epoxy-l-octene. Tetrahedron Letters 3967 (1973).Google Scholar
  104. 104.
    Dunlop, R. W., P. T. Murphy, and R. J. Wells: A New Polyhalogenated Monoterpene from the Red Alga Plocamium angustum. Aust. J. Chem. 32, 2735 (1979).CrossRefGoogle Scholar
  105. 105.
    Kazlauskas, R., P. T. Murphy, R. J. Quinn, and R. J. Wells: TWO Polyhalogenated Monoterpenes from the Red Alga Plocamium costatum. Tetrahedron Letters 4451 (1976).Google Scholar

Copyright information

© Springer-Verlag/Wien 1983

Authors and Affiliations

  • S. Naylor
    • 1
  • F. J. Hanke
    • 1
  • L. V. Manes
    • 1
  • P. Crews
    • 1
  1. 1.Thimann Laboratories and Center for Coastal Marine StudiesUniversity of CaliforniaSanta CruzUSA

Personalised recommendations