PHENOLIC ETHER LIPIDS WITH AN N-ALKENYLRESORCINOL MOIETY FROM A BOLIVIAN STRAIN OF BOTRYOCOCCUS-BRAUNII (A-RACE)

Authors
Citation
P. Metzger, PHENOLIC ETHER LIPIDS WITH AN N-ALKENYLRESORCINOL MOIETY FROM A BOLIVIAN STRAIN OF BOTRYOCOCCUS-BRAUNII (A-RACE), Phytochemistry, 36(1), 1994, pp. 195-212
Citations number
15
Categorie Soggetti
Plant Sciences
Journal title
ISSN journal
00319422
Volume
36
Issue
1
Year of publication
1994
Pages
195 - 212
Database
ISI
SICI code
0031-9422(1994)36:1<195:PELWAN>2.0.ZU;2-T
Abstract
Eight series of phenolic ether lipids have been isolated from a Bolivi an strain of Botryococcus braunii (A race). The lipids constitute, as a whole, up to 34% of the dry biomass. They are structurally related t o a homologous series of three long chain n-alkenylresorcinols with C- 25, C-27 (major) and C-29 hydrocarbon chains, and, a minor series of n -alkenylresorcinol dimethyl ethers excepted, to hydrocarbons e.g. C-27 dienes and tetraenes previously identified in this strain. The above structures were determined by spectroscopic analyses and chemical degr adations involving oxidation and ether cleavage. With the exception of the dimethyl ethers, these lipids exhibit one or two ether bridges bi nding, on the one hand, the resorcinol nucleus, and on the other a C-2 7 alkatrienyl chain and/or a C-27 alkenyl one. The latter can, in turn be ether-linked to an alkatrienyl chain, thus resulting in the format ion of high M(r) ether lipids. Moreover, one of these phenolic ethers was found to result from a C-alkylation of the aromatic nucleus. On st ructural grounds, a biogenetic relationship is proposed between these unusual ether lipids, with the monoepoxides derived from C-27 dienes a nd C-27 tetraenes as possible intermediates in thetetraenes as possibl e intermediates in the O- and C-alkylation pathways of the resorcinol nucleus.