A dialkylcyclohexadienecarbinol from the bacterium Zymomonas mobilis, a novel type of potential membrane lipid

Koukkou, Anna‐Irini; Douka, Eugenia; Drainas, Constantin; Pale-Grosdemange, Catherine; Rohmer, Michel

doi:10.1016/s0040-4039(98)01059-4

Cited by 6 publications

(3 citation statements)

References 11 publications

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“…[20]. The composition of the Z. mobilis hydrocarbon fraction is very striking, containing triterpenes that have never previously been observed in prokaryotes, such as the bicyclic K-and Q-polypodatetraenes (2 and 3) and a complete series of rearranged hopenes, including hop-21-ene (13), hop-17(21)-ene (7), neohop-13(18)-ene (8), neohop-12-ene (10) and the fully rearranged fern-8-ene (11). All these hydrocarbons were present in Z. mobilis in larger amounts than those found in the formerly mentioned bacteria, at concentrations of the same order of magnitude as that of diploptene.…”

Section: Resultsmentioning

confidence: 99%

“…Such membrane lipids are thought to counterbalance the destabilizing action of ethanol, playing an essential role as modulators in ethanol tolerance [4]. Continuing our lipid screening in Z. mobilis, in an e¡ort to better understand its unusual tolerance towards membrane-unfriendly growth conditions [8], we now report the identi¢cation of triterpenic hydrocarbons ( Figs. 1 and 2), which are characteristic for failures of the normal cyclization process of squalene into diploptene [9].…”

Section: Introductionmentioning

confidence: 92%

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Structural diversity of the triterpenic hydrocarbons from the bacterium Zymomonas mobilis: the signature of defective squalene cyclization by the squalene/hopene cyclase

Douka¹

2001

FEMS Microbiology Letters

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Twelve polycyclic triterpenic hydrocarbons (K-and Q-polypodatetraenes, dammara-20(21),24-diene, 17-isodammara-12,24-diene, eupha-7,24-diene, hop-17(21)-ene, neohop-13(18)-ene, 17-isodammara-20(21),24-diene, neohop-12-ene, fern-8-ene, diploptene and hop-21-ene) were detected in the hydrocarbon fraction from the bacterium Zymomonas mobilis. Some of them have never been reported from bacteria. These triterpenes were present in Z. mobilis in significant amounts, comparable to those of diploptene, which is usually the major triterpenic hydrocarbon in hopanoid-producing bacteria. The occurrence of such compounds confirms the lack of specificity of bacterial squalene cyclases and the possibility of alternative cyclization routes induced by the existence in the cyclization process of intermediate carbocations of sufficient lifetime. ß

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 92%

Structural diversity of the triterpenic hydrocarbons from the bacterium Zymomonas mobilis: the signature of defective squalene cyclization by the squalene/hopene cyclase

Douka¹

2001

FEMS Microbiology Letters

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“…Such membrane lipids are thought to counterbalance the destabilizing action of ethanol, playing an essential role as modulators in ethanol tolerance [4]. Continuing our lipid screening in Z. mobilis , in an effort to better understand its unusual tolerance towards membrane‐unfriendly growth conditions [8], we now report the identification of triterpenic hydrocarbons (Figs. 1 and 2), which are characteristic for failures of the normal cyclization process of squalene into diploptene [9].…”

Section: Introductionmentioning

confidence: 94%

Structural diversity of the triterpenic hydrocarbons from the bacterium Zymomonas mobilis: the signature of defective squalene cyclization by the squalene/hopene cyclase

Douka

Koukkou

Drainas

et al. 2001

FEMS Microbiology Letters

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Twelve polycyclic triterpenic hydrocarbons (alpha- and gamma-polypodatetraenes, dammara-20(21),24-diene, 17-isodammara-12,24-diene, eupha-7,24-diene, hop-17(21)-ene, neohop-13(18)-ene, 17-isodammara-20(21),24-diene, neohop-12-ene, fern-8-ene, diploptene and hop-21-ene) were detected in the hydrocarbon fraction from the bacterium Zymomonas mobilis. Some of them have never been reported from bacteria. These triterpenes were present in Z. mobilis in significant amounts, comparable to those of diploptene, which is usually the major triterpenic hydrocarbon in hopanoid-producing bacteria. The occurrence of such compounds confirms the lack of specificity of bacterial squalene cyclases and the possibility of alternative cyclization routes induced by the existence in the cyclization process of intermediate carbocations of sufficient lifetime.

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Preparation of Difunctional Compounds

2002

Compendium of Organic Synthetic Methods

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A dialkylcyclohexadienecarbinol from the bacterium Zymomonas mobilis, a novel type of potential membrane lipid

Cited by 6 publications

References 11 publications

Structural diversity of the triterpenic hydrocarbons from the bacterium Zymomonas mobilis: the signature of defective squalene cyclization by the squalene/hopene cyclase

Structural diversity of the triterpenic hydrocarbons from the bacterium Zymomonas mobilis: the signature of defective squalene cyclization by the squalene/hopene cyclase

Structural diversity of the triterpenic hydrocarbons from the bacterium Zymomonas mobilis: the signature of defective squalene cyclization by the squalene/hopene cyclase

Preparation of Difunctional Compounds

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