Botryococcene–a tetramethylated acyclic triterpenoid of algal origin

Lipids and Macromolecular Lipids of the Hydrocarbon-rich Microalga Botryococcus braunii. Chemical Structure and Biosynthesis. Geochemical and Biotechnological Importance

“…13C-NMR analysis and permanganateperiodate oxidation to (17) supported gross structure (16) (31). The absolute configuration of this botryococcene was recently established by oxidative degradation of the 26,27-dihydroderivative and comparison of the resulting enantiomers with optically pure synthons (38).…”

“…The first hydrocarbon described from the B race was a C 34 compound called "botryococcene" (31), one of the most widespread members of the botryococcene family as demonstrated by subsequent studies. Due to its large predominance in the total hydrocarbon fraction isolated from some strains, ca 90%, no additional purification was needed for identification of the C 34 compound.…”

“…On the basis of structural considerations it was at first proposed that the C34 botryococcene (16) arose from a tail-to-tail linkage of two dimethylated C 1S units (31). However, characterization of numerous lower and higher homologues and feeding experiments with 14C and 13C labelled precursors suggest that the C 30 compound (7), derived from the irregular coupling of two farnesyl pyrophosphates via presqualene pyrophosphate, is in fact the precursor of all the higher botryococcenes.…”

“…CH 2 In the synthesis depicted in Fig. 10, WHITE et al (52) converted the protected methoxymethyl (MOM) ether (30) derived from (29) into the aldehyde (31), followed by a Wittig reaction to obtain the E cx.,~ unsaturated ester (32); Subsequent reaction of the bis-MOM derivative (33) with lithium diisopropylamide furnished, via a fragmentation-recombination process, two diastereoisomers (34) and (35). After chromatographic separation of (34), its bis-ether derivative (36) was converted into an aldehyde which was transformed to (37) in a second Wittig reaction.…”

Sedimentary lipids as indicators of depositional conditions in the coastal Peruvian upwelling regime

“…The fresh-water, green microalga Botryococcus braunii has been found to produce significant concentrations of other acyclic isoprenoid hydrocarbons (MAXWELL et al, 1968;COX et al, 1973), including tetradehydrolycopane (METZGER and CASADEV ALL, 1987). A planktonic source of lycopane in SC3 is consistent with the loading of lycopane on factor 1 with C27 stenols, C2s stenols, and phytol, compounds with unequivocally planktonic sources, and with tetrahymanol, a compound of probable planktonic origin.…”