The Botryococcenes—hydrocarbons of novel structure from the alga Botryococcus braunii, Kützing

Maxwell, James R.; Douglas, A.G.; Eglinton, G.; McCormick, A.

doi:10.1016/s0031-9422(00)85672-1

Cited by 209 publications

(61 citation statements)

References 12 publications

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“…Origin of BAQCs. Quaternary substituted carbon atoms are extremely rare in aliphatic natural products, with the exception of the isoprenoid-based botryococcenes from the alga Botryococcus braunii (27). These rare exceptions also include the tert-butyl lipidic side chains of the feeding deterrents ypaoamide and antillatoxin of the cyanobacterium Lyngbia majuscula (28,29).…”

Section: Resultsmentioning

confidence: 99%

Branched aliphatic alkanes with quaternary substituted carbon atoms in modern and ancient geologic samples

Kenig

Simons

Crich

et al. 2003

Proc. Natl. Acad. Sci. U.S.A.

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A pseudohomologous series of branched aliphatic alkanes with a quaternary substituted carbon atom (BAQCs, specifically 2,2-dimethylalkanes and 3,3-and 5,5-diethylalkanes) were identified in warm (65°C) deep-sea hydrothermal waters and Late Cretaceous black shales. 5,5-Diethylalkanes were also observed in modern and Holocene marine shelf sediments and in shales spanning the last 800 million years of the geological record. The carbon number distribution of BAQCs indicates a biological origin. These compounds were observed but not identified in previous studies of 2.0 billion-to 2.2 billion-year-old metasediments and were commonly misidentified in other sediment samples, indicating that BAQCs are widespread in the geological record. The source organisms of BAQCs are unknown, but their paleobiogeographic distribution suggests that they have an affinity for sulfides and might be nonphotosynthetic sulfide oxidizers. P rokaryotes in ancient environments usually are detected by microscopy (1, 2) and geochemical evidence (e.g., stable isotope fractionation of carbon and sulfur; ref.3). The fossil record of bacteria and archaea is meager and controversial because of their poor preservation potential (1, 4). However, some lipids have excellent preservation potential and are used to demonstrate the presence of archaea and bacteria in ancient sedimentary environments (2, 5-9). Here we identify branched aliphatic alkanes with quaternary substituted carbon atoms (BAQCs). These compounds, observed in hydrothermal waters at the Ocean Drilling Project (ODP) site 1026B on the flanks of the Juan de Fuca ridge (Northeast Pacific) are natural products and occur in nonhydrothermal sediments ranging in age from modern to at least 2.0 billion to 2.2 billion years (Ga). MethodsField Sampling. Particulate organic material was retrieved from hydrothermal waters by using a combusted glass-fiber filter (142 mm) affixed to a circulation obviation retrofit kit (10) The Cenomanian and Turonian (Late Cretaceous) samples were collected at outcrops along the Bainbridge river in the Pasquia Hills region of easternmost central Saskatchewan, Canada (12). They are thermally immature based on the dominant 17␤,21␤(H) stereochemical configuration of the hopanes. The descriptions of other sediment samples analyzed can be found in the references listed in the Fig. 3 legend. Laboratory Methods. Extraction, separation, and GC-MS were performed as described (13). The filter and sediment samples were Soxhlet-extracted by using dichloromethane and methanol (7.5:1, vol͞vol). The sediment extracts were further separated by column chromatography to obtain a hydrocarbon fraction. Linear alkanes were removed from the hydrocarbon fraction by adduction on US-Y zeolite to obtain a fraction of branched and cyclic hydrocarbons. The total extract and subfractions, as well as authentic standards, were analyzed by GC-MS on a HewlettPackard 6890 gas chromatograph coupled to a Hewlett-Packard 5973 mass selective detector operated in electron ionization mode at 70 eV, scannin...

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Section: Resultsmentioning

confidence: 99%

Branched aliphatic alkanes with quaternary substituted carbon atoms in modern and ancient geologic samples

Kenig

Simons

Crich

et al. 2003

Proc. Natl. Acad. Sci. U.S.A.

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“…As shown in chromatogram II, the nonpolar lipid fraction of the A strain was resolved into many components, some of which were identified by co-thin-layer chromatography with authentic standards as sterol ester (spot 1), wax ester (2), triacylglycerols (3", 5), free fatty acid (6), diacylglycerols (7 and 8), sterol (9), chlorophyll (10), and monoacylglycerol (11). Several spots of carotenoid as indicated with oblique lines were also found.…”

Section: Content and Composition Of Lipidsmentioning

confidence: 99%

Lipid Composition of a Green Alga,Botryococcus braunii

Yamaguchi¹,

Nakano²,

Murakami³

et al. 1987

Agricultural and Biological Chemistry

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Botryococcus braunii strain Austin and strain Berkeley cultured under the same conditions contained 27.4 g and 34.0 g of lipids per 100 g of dry alga, respectively. The lipids in the former strain were 25.5% hydrocarbons, 58.8% other nonpolar lipids, and 15.7% polar lipids, and those in the latter strain were 71.6%, 9.2%, and 19.2%, respectively. Distinct differences were also observed in the components of the nonpolar and polar lipids, especially in the latter, between the strains. The fatty acid composition of the nonpolar lipid fraction in Austin strain was unique, oleic acid being 81 % of the total acids.The colonial microalga Botryococcus braunii is a freshwater autotrophic species belonging to the Chlorophyceae and is known to produce unusually high levels of liquid hydrocarbons. The alga has been proposed as a renewable source of fuels from recent concern for future energy requirements. It occurs throughout the world in a wide variety of climates and includes several strains which are classified into two races, A and B.ll The A race accumulates linear olefins, odd numbered from 23 to 31, chiefly CZ7 , CZ9 ' and C31 dienes or trienes, whereas the B race produces polyunsaturated triterpenes of the general formula CnH2n-10, n = 30 ~ 37, termed botryococcenes. 1 -4) These findings suggest that the same strain is unable to yield successively the two types of hydrocarbons contrary to previous proposals. 5 ) Numerous reports have been published regarding hydrocarbons of this alga in relation to production and composition under different growth conditions,4-10) their chemical structures,Z,1l-15) and biosynthesis.1 6 -1 9 ) Largeau et al. 16J showed that [9,1O-3H]-palmitic acid was rapidly incorporated into the A race hydrocarbons and Templier et al.17) indicated that [1O-14C]-0Ieic acid was an efficient precursor of the hydrocarbons. These fatty acids seem to be key intermediate metabolites in the biosynthesis from carbon dioxide to alkadienes and trienes.Douglas et aeO) reported that fatty acids of a natural winter bloom of B. braunii Kiitzing belonging to the B race ranged from C 14 to C 30 , palmitic, oleic, octacosenoic acids being the major components. To our knowledge, however, no other information is available concerning the fatty acid composition of B. braunii.Such a situation prompted us to investigate lipid composition of this alga. In this study, we have chosen two B. braunii strains, one each from the A and B races, and compared their lipids. We report here their nonpolar and polar 494 K. YAMAGUCHI et al. lipid composition and fatty acid composition. MATERIALS AND METHODSMicroorganisms. Botryococcus braunii strain Austin belonging to the A race was obtained from the Austin culture collection (University of Texas) and B. braunii strain Berkeley belonging to the B race was originally isolated to unialgal culture by Dr. Arthur M. Nonomura from lilyculturing tanks in the Department of Botany greenhouse of the University of California, Berkeley.4) Henceforth, they are referred to as the A and B strai...

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“…Figure 16b). The source of this soluble organic matter appears to be marine, and it may have had a major contribution from an unknown species analogous to the present day alga Botryococcus braunü, which contains various C 34 hydrocarbons at one stage of its life cycle (Maxwell et al, 1968). .…”

Section: Discussionmentioning

confidence: 99%

Preliminary Organic Analyses of DSDP Cores, Leg 14, Atlantic Ocean

Simoneit¹,

Scott²,

Burlingame³

1973

Initial Reports of the Deep Sea Drilling Project

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Organic carbon-rich samples from Sites 138 and 144 of DSDP Leg 14 were analyzed. A sample of Oligocene age yielded mainly alkanes, C n H2 w+ 2 for n = 19 to 36 with an odd over even predominance; carboxylic acid methyl esters (formed by clay catalysis with solvent methanol), C π H2 W θ2 for n = 14 to 25 with an even over odd predominance; and steranes (e.g. cholestane, ergostane, and stigmastane), sterones, and triterpanes. The other samples, all of Cretaceous age, yielded mainly alkanes, C n U2n+2 for n = 19 to 30 + with no significant predominance; carboxylic acid methyl esters, C w H2 n θ2 for n = 14 to 24 with no predominance; and sterones and steranes probably of marine origin. These Cretaceous sediments contain large amounts of kerogen and the extractable petroliferous material appears to have gone through maturation processes.

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The Botryococcenes—hydrocarbons of novel structure from the alga Botryococcus braunii, Kützing

Cited by 209 publications

References 12 publications

Branched aliphatic alkanes with quaternary substituted carbon atoms in modern and ancient geologic samples

Branched aliphatic alkanes with quaternary substituted carbon atoms in modern and ancient geologic samples

Lipid Composition of a Green Alga,Botryococcus braunii

Preliminary Organic Analyses of DSDP Cores, Leg 14, Atlantic Ocean

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