C25 and C30 highly branched isoprenoid alkenes in laboratory cultures of two marine diatoms

Abstract C 25 and C 30 highly branched isoprenoid (HBI) alkenes have been isolated from laboratory cultures of the marine diatoms Haslea ostrearia and Rhizosolenia setigera . At least seven C 25 isoprenoid alkenes, with carbon skeleton II , were found in the culture of H. ostrearia . A C 25:4 HBI alkene was the major hydrocarbon present. Other hydrocarbons included a C 25:3 alkene, a different C 25:4 alkene, two C 25:5 alkenes and two unidentified minor components that exhibited properties consistent with alkenes. Three C 30:5 HBI alkenes and smaller amounts of two C 30:6 alkenes, all with carbon skeleton III , were identified in R. setigera . These isoprenoid hydrocarbons were not present in thirteen other species of diatom examined. All species possessed the alkene n -heneicosa-3,6,9,12,15,18-hexaene ( n -C 21:6 ), and eight also had n -heneicosa-3,5,9,12,15-pentaene ( n -C 21:5 ). Highly branched isoprenoid alkenes are commonly reported in marine sediments and waters, but this is their first identification in marine microalgae. These data support previous suggestions that these alkenes might be derived from diatoms in many contemporary marine environments.

[1]  S. M. Barrett,et al.  Essential polyunsaturated fatty acids from 14 species of diatom (Bacillariophyceae) , 1993 .

[2]  M. Altabet,et al.  Nitrogen transport by vertically migrating diatom mats in the North Pacific Ocean , 1993, Nature.

[3]  A. Alldredge,et al.  Abundance and production rates of floating diatom mats (Rhizosolenia castracanei and R. imbricata var. shrubsolei) in the Eastern Pacific Ocean , 1982 .

[4]  R. Risebrough,et al.  Recent contributions of high resolution gas chromatography to the analysis of environmental hydrocarbons , 1983 .

[5]  J. Damsté,et al.  Characterisation of highly branched isoprenoid thiophenes occurring in sediments and immature crude oils , 1989 .

[6]  Richard F. Lee,et al.  Distribution of 21:6 hydrocarbon and its relationship to 22:6 fatty acid in algae , 1971 .

[7]  P. Boehm,et al.  Benthic hydrocarbons of Rhode Island Sound , 1978 .

[8]  F. Prahl,et al.  The early diagenesis of aliphatic hydrocarbons and organic matter in sedimentary particulates from Dabob Bay, Washington , 1980 .

[9]  Jack G. Baldauf,et al.  Vast Neogene laminated diatom mat deposits from the eastern equatorial Pacific Ocean , 1993, Nature.

[10]  R. Guillard,et al.  Studies of marine planktonic diatoms. I. Cyclotella nana Hustedt, and Detonula confervacea (cleve) Gran. , 1962, Canadian journal of microbiology.

[11]  C. Sancetta Green sea, black mud , 1993, Nature.

[12]  Pierre Metzger,et al.  Lycopadiene, a tetraterpenoid hydrocarbon from new strains of the green alga Botryococcus braunii. , 1987 .

[13]  P. Gearing,et al.  Hydrocarbons in 60 northeast Gulf of Mexico shelf sediments: a preliminary survey , 1976 .

[14]  N. Frew,et al.  Hydrocarbons in cores of northwestern Atlantic coastal and continental margin sediments , 1977 .

[15]  J. Hedges,et al.  Hydrocarbon geochemistry of the Puget Sound region—II. Sedimentary diterpenoid, steroid and triterpenoid hydrocarbons , 1981 .

[16]  J. Huisman,et al.  Toxic effects of a bloom of the diatom Rhizosolenia chunii on shellfish in Port Phillip Bay, Southeastern Australia , 1989 .

[17]  J. Hayes,et al.  Recognition of Paleobiochemicals by a Combined Molecular Sulfur and Isotope Geochemical Approach , 1992, Science.

[18]  J. N. Robson Synthetic and biodegradation studies of some sedimentary isoprenoid hydrocarbons , 1987 .

[19]  S. Rowland,et al.  Synthesis of a highly branched C30 sedimentary hydrocarbon , 1988 .

[20]  G. Ryback,et al.  2,6,10-Trimethyl-7-(3-methylbutyl)-dodecane, a novel sedimentary biological marker compound. , 1982 .

[21]  J. Grimalt,et al.  Extractable and bound neutral lipids in some lacustrine sediments , 1984 .

[22]  J. Hedges,et al.  Hydrocarbon geochemistry of the Puget Sound region—I. Sedimentary acyclic hydrocarbons , 1980 .

[23]  R. Risebrough,et al.  Dissolved, particulate and sedimentary hydrocarbons in a deltaic environment , 1984 .

[24]  E. Casadevall,et al.  Structures of some botryococcenes: branched hydrocarbons from the b-race of the green alga Botryococcus braunii , 1985 .

[25]  G. Fryxell,et al.  Handbook of the Common Plankton Diatoms of the Southern Ocean: Centrales Except the Genus Thalassiosira , 1986 .

[26]  C. Largeau,et al.  Lipids and Macromolecular Lipids of the Hydrocarbon-rich Microalga Botryococcus braunii. Chemical Structure and Biosynthesis. Geochemical and Biotechnological Importance , 1991 .

[27]  S. M. Barrett,et al.  C30C32 alkyl diols and unsaturated alcohols in microalgae of the class Eustigmatophyceae , 1992 .

[28]  S. Rowland,et al.  Occurrence of 2,6,10-trimethyl-7-(3-methylbutyl)-dodecane and related hydrocarbons in the green alga Enteromorpha prolifera and sediments , 1985 .

[29]  S. Rowland,et al.  Identification of novel widely distributed sedimentary acyclic sesterterpenoids , 1986, Nature.

[30]  S. Rowland,et al.  The widespread occurrence of highly branched acyclic C20, C25 and C30 hydrocarbons in recent sediments and biota—A review , 1990 .

[31]  J. Quinn,et al.  Geochemistry of C25 and C30 biogenic alkenes in sediments of the narragansett bay estuary , 1983 .

[32]  C. Stranger,et al.  The Structure of a New C25 Isoprenoid Alkene Biomarker From Diatomaceous Microbial Communities , 1993 .

[33]  Peter D. Nichols,et al.  OCCURRENCE OF AN ISOPRENOID C25 DIUNASATURATED ALKENE AND HIGH NEUTRAL LIPID CONTENT IN ANTRACTIC SEA‐ICE DIATOM COMMUNITIES 1 , 1988 .

[34]  A. Alldredge,et al.  Nitrogen Fixation by Floating Diatom Mats: A Source of New Nitrogen to Oligotrophic Ocean Waters , 1983, Science.

[35]  P. Falkowski,et al.  Massive fluxes of rhizosolenid diatoms: A common occurrence? , 1991 .