Saturated and unsaturated hydrocarbons in marine benthic algae

Marine Biology - Tập 8 - Trang 190-201 - 1971
W. W. Youngblood1, M. Blumer2, R. L. Guillard2, F. Fiore3
1Chemistry Department, Florida Technological University, Orlando, USA
2Woods Hole Oceanographic Institution; Woods Hole USA
3Systematics-Ecology Program, Marine Biological Laboratory, Woods Hole, USA

Tóm tắt

Saturated and olefinic hydrocarbons were determined in 24 species of green, brown and red benthic marine algae from the Cape Cod area (Massachusetts, USA). Among the saturated hydrocarbons, n-pentadecane predominates in the brown and n-heptadecane in the red algae. A C17 alkyleyclopropane has been identified tentatively in Ulvalactuca and Enteromorpha compressa, two species of green algae. Mono-and diolefinic C15 and C17 hydrocarbons are common. The structures of several new C17, C19 and C21 mono-to hexaolefins have been elucidated by gas chromatography, mass spectrometry and ozonolysis. In fruiting Ascophyllum nodosum, the polyunsaturated hydrocarbons carbons occur exclusively in the reproductive structures. The rest of the plant contains n-alkanes from C15 to C21. A link between the reproductive chemistry of benthic and planktonic algae and their olefin content is suggested. An intriguing speculation is based on Paffenhöfer's (1970) observation that the sex ratio of laboratory reared Calanus helgolandicus depends upon the species of algae fed to the nauplii. The percentage of males produced correlates with our analyses of heneicosahexaene in the algal food. Our analyses of the hydrocarbons in benthic marine algae from coastal environments should aid studies of the coastal food web and should enable us to distinguish between hydrocarbon pollutants and the natural hydrocarbon background in inshore waters.

Tài liệu tham khảo

Ackman, R. G., C. S. Tocher and J. McLachlan: Marine phytoplankter fatty acids. J. Fish Res. Bd Can. 25, 1603–1620 (1968). Blumer, M.: Hydrocarbons in the digestive tract and the liver of a basking shark. Science, N.Y. 156, 390–391 (1967). —An integrated gas chromatograph-mass spectrometer system with carrier gas separator. Analyt. Chem. 40, 1590–1592 (1968). Blumer, M. The persistence of an olefinic hydrocarbon in the marine food web. In: Summary of investigation, p. 40. Unpubl. M.s. Woods Hole Oceanographic Institution 1969. —The organic chemistry of sea water In: Symposium on organic matter in natural waters. Ed. by D. W. Hood. Alaska: University Press 1970. (In press). —R. R. L. Guillard and T. Chase: Hydrocarbons of marine phytoplankton. Mar. Biol. 8, 183–189 (1971). —M. M. Mullin and R. R. L. Guillard: A polyunsaturated hydrocarbon (3,6,9,12,15,18-heneicosahexaene) in the marine food web. Mar. Biol. 6, 226–236 (1970a). ——D. W. Thomas: Pristane in the marine environment. Helgoländer wiss. Meeresunters. 10, 187–201 (1964). —J. C. Robertson, J. E. Gordon and J. Sass: Phytolderived C19 di-and triolefinic hydrocarbons in marine zooplankton and fishes. Biochemistry, N.Y. 8, 4067–4074 (1969). M. M. Mullin G. Souza and J. Sass: Hydrocarbon pollution of edible shellfish by an oil spill. Ref. No. 70-1, pp 1–13. Unpubl. M.s. Woods Hole Oceanographic Institution, 1970b. Blumer, M., M. M. Mullin H. L. Sanders, J. F. Grassle and G. R. Hampson: The West Falmouth oil spill. Ref. 70-44, pp 1–32. Unpubl. M.s. Woods Hole Oceanographic Institution. 1970c. ——J. Sass: Hydrocarbon pollution of edible shellfish by an oil spill. Mar. Biol. 5, 195–202 (1970b). Budzikiewicz, H., C. Djerassi and D. H. William: Mass spectra of organic compounds, 690 pp. San Fracisco: Holden Day 1967. Burg, S. P. and E. A. Burg: Ethylene action and the ripening of fruits. Science, N.Y. 148, 1190–1196 (1965). Clark, R. C., Jr. and M. Blumer: Distribution of n-paraffins in marine organisms and sediments. Limnol. Oceanogr. 12, 79–87 (1967). Collins, C. J.: Protonated cyclpropanes. Chem. Rev. 69, 543–550 (1969). Gelpi, E., J. Oro, H. J. Schneider and E. O. Bennet: Olefins of high molecular weight in two microscopic algae. Science, N.Y. 161, 700–702 (1968). —H. Schneider, J. Mann and J. Oro: Hydrocarbons of geochemical significance in microscopic algae. Phytochem. 9, 603–612 (1970). Khimii, U.: Structure and reactivity of cyclopropane and its derivatives. Russian Chem. Rev. 31, 419–439 (1962). Kovats, E.: Gas-chromatographische Charakterisierung organischer Verbindungen. Teil 1: Retentionsindices aliphatischer Halogenide, Alkohole, Aldehyde und Ketone. Helv. chim. Acta 41, 1915–1932 (1958). Lawrence, C. D. and F. H. Tipper: Some reactions of cyclopropane and a comparison with the lower olefins. Part I. Introduction and reaction with strong acids. J. chem. Soc. 1, 713–716 (1955). Lee, R. F., J. C. Nevenzel, G. A. Paffenhöfer, A. A. Benson, S. Patton and T. E. Kavanagh: A unique hexaene hydrocarbon from a diatom (Skeletonema costatum). Biochem. biophys. Acta 202, 386–388 (1970). Moore, R. E., J. A. Pettus, Jr. and M. S. Doty: Dictoptyerene A, an odoriferous constituent from algae of the genus Dictyopteris. Tetrahedron Lett. 46, 4787–4790 (1968). Paffenhöfer, G. A.: Cultivation of Calanus helgolandicus under controlled conditions. Helgoländer wiss. Meeresunters. 20, 346–359 (1970). Pettus, J. A. and R. E. Moore: Isolation and structure determination of an undeca-1,3,4,8-tetraene and dictyopterene B from algae of the genus Dictyopteris. Chem. Comm. 17, 1093–1094 (1970). Stránský, K. and M. Streibl: On natural waxes. XII. Composition of hydrocarbons in morphologically different plant parts. Colln Czech. chem. Commun. Engl. Edn 34, 103–107 (1969). Taylor, W. R.: Marine algae of the Eastern tropical and subtropical coasts of the Americas, 870 pp. Ann Arbor, Michigan: University of Michigan Press 1960. —Marine algae of the northeastern coast of North America. Second revised edition, second printing with corrections and addenda, 509 pp. Ann Arbor, Michigan: University of Michigan Press 1962. Wall, D., R. R. L. Guillard, B. Dale, E. Swift and N. Watabe: Calcitic resting cysts in Peridinium trochoideum (Stein) Lemmermann, an autotrophic marine dinoflagellate. Phycologia 9 (2), 151–156 (1970). Wehrli, A. and E. Kovats: Gaschromatographische Charakterisierung organischer Verbindungen. Teil 3: Berechnung der Retentionsindices aliphatischer, alioyclischer und aromatischer Verbindungen. Helv. chim. Acta 42, 2709–2736 (1959).