✍ Scribed by Pierre Metzger*; André Aumelas
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A series of polyethersof a new type, IycopanerolsA, consistingof tetraterpenoid and unbranchedaliphaticmoieties,was isolatedfmm a L strain of the greenmicmalgaBonyococcus ImmJW.Their structureswereestablishedon the basis of [email protected] Science Ltd.
TheL shainsof thegreenwlonialmicroalgaBotryococcus bmuru 'iare chamcterizedby the productionof lycopadiene1, anacyclictetraterpenoid hy~nl.
This compoud is synthesizedin variableamounts by thealga (0.07-8% of drywt)dependingonthe originofthe stmin2; it couldbeat the originof Iycopanefound in somelacusttinesediments3a9b. Fromthe oil extractedfromthedryalgalbiomasswith heptane,we isolated also a monoepoxidederivedfromlycopadieneand its corresponding dio14.We have furtherinvestigatedthe extractsandisolatedseveralseriesof polyetherswe namedlycopanerols. In this paperwe reportthe isolation andthe structuralelucidationof compoundsof oneoftheseseries,Iycopanerols A, 2.
B. bruum"i (Yamoussoukm strain,Ivory-Coast) wasculturedunderair-liftconditions(1%C02), at 25"C, undercontinuouslight of 470 kE.m-2.S-l and on a chemicallydefinedmedinm5.The extractionof the dry biomasswithheptanefurnisheda resin-likeextractfromwhicha rubberymaterialwas removedby dissolution in CHC13and additionof an equivalentvolumeof MeOH. The remainingfiltrate, free of "rubber",was subjectedto silicagelcolumnchromatography and the fractionelutedwithheptadether (19:1)was collected. FurtherpurificationofthisfractionbyTLCoversilicagelfurnisheda clearoil (12.6%of drywt);[a&o= -6.9' (c. 4.58, n-heptane).The HRFAB(NBA-LiCl) mass spectrumdisplayedthree [M+L.i]+adductions at rrdz 15%.6512,1624.6764and 1652.7133, in a ratio of c.a 12:35:53, corresponding to the molecularformulae C108H212O5([M+fi]+ ~alcd. 1596.6495),C11OH216O5 ([M+Li]+C~Cd. 1624.6808)~d Cl12H22005 ([M+Ii]+ calcd. 1652.7121)respectively;these data suggestedthat the mixture was made of a series of homologous compoundsincreasingin molecularmassbytwomethylenessuccessively.
TheIR spectrumshowedabsorptionbandsfor hydmxylgroup(3580cm-l) and C-O bonds(1095and 1070cm-l). The presenceof a tertiaryalcoolfunctionwas deducedfmm trimethylsilylation and fmm the
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