Hopanoid lipids in Bradyrhizobium and other plant-associated bacteria and cloning of the Bradyrhizobium japonicum squalene-hopene cyclase gene

Kannenberg, Elmar L.; Perzl, Michael; Müller, Peter; Härtner, Thomas; Poralla, Karl

doi:10.1007/978-94-011-5700-1_15

Cited by 6 publications

(6 citation statements)

References 18 publications

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“…For overview on biochemical properties of well-studied SHCs, see Table 1. The highest amino acid similarity of B. japonicum SHC was found to a Zymomonas mobilis SHC (43,68,69). The genetic context of these two SHCs has been analyzed in more detail.…”

Section: Purification and Properties Of Shcsmentioning

confidence: 99%

Squalene-Hopene Cyclases

Siedenburg

Jendrossek

2011

Appl Environ Microbiol

124

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Hopanoids and sterols are members of a large group of cyclic triterpenoic compounds that have important functions in many prokaryotic and eukaryotic organisms. They are biochemically synthesized from linear precursors (squalene, 2,3-oxidosqualene) in only one enzymatic step that is catalyzed by squalene-hopene cyclase (SHC) or oxidosqualene cyclase (OSC). SHCs and OSCs are related in amino acid sequences and probably are derived from a common ancestor. The SHC reaction requires the formation of five ring structures, 13 covalent bonds, and nine stereo centers and therefore is one of the most complex one-step enzymatic reactions. We summarize the knowledge of the properties of triterpene cyclases and details of the reaction mechanism of Alicyclobacillus acidocaldarius SHC. Properties of other SHCs are included.

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Section: Purification and Properties Of Shcsmentioning

confidence: 99%

Squalene-Hopene Cyclases

Siedenburg

Jendrossek

2011

Appl Environ Microbiol

124

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“…This is also the case for Rhizobium NGR234, where a cluster of open reading frames (ORFs) with signi¢cant similarity to hopanoid biosynthetic genes in Zymomonas mobilis and Bradyrhizobium japonicum [3], including the gene for squalene^hopene cyclase, are encoded by the symbiosis plasmid [4]. Yet, no hopanoids have been detected in laboratory cultures [5], indicating that hopanoids are formed under speci¢c environmental or developmental conditions.…”

Section: Introductionmentioning

confidence: 99%

Hopanoids are formed during transition from substrate to aerial hyphae in Streptomyces coelicolor A3(2)

Poralla

2000

FEMS Microbiology Letters

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Streptomyces coelicolor A3(2) contains a cluster of putative isoprenoid and hopanoid biosynthetic genes. The strain does not produce the pentacyclic hopanoids in liquid culture but produces them on solid medium when sporulating. Mutants defective in the formation of aerial mycelium and spores (bld), with the exception of bldB, do not synthesize hopanoids, whereas mutants, which form aerial mycelium but no spores (whi), do. The membrane condensing hopanoids possibly may alleviate stress in aerial mycelium by diminishing water permeability across the membrane. ß

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“…nodulating Lupinus and the closely related, photosynthetic, nitrogenfixing Photorhizobium sp. BTAiI, nodulating the tropical legume Aeschynomene indica) the occurrence of diploptene (1) and diplopterol (2), which are both nearly ubiquitous in hopanoid producers, as well as dihomohopan-32-ol, which represented the signature of the C 35 bacteriohopanepolyol derivatives [12,26]. According to the GC analyses, all these hopanoid producing strains [e.g.…”

Section: Discussionmentioning

confidence: 99%

“…Is it the same enzyme, which produces the two triterpene series, or are two different enzymes required? A squalene cyclase gene has been cloned from both organisms and expressed in Escherichia coli [26,35]. In addition, in Rh.…”

Section: Discussionmentioning

confidence: 99%

Novel methylated triterpenoids of the gammacerane series from the nitrogen‐fixing bacterium Bradyrhizobium japonicum USDA 110

Bravo

Perzl

Härtner

et al. 2001

European Journal of Biochemistry

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The nitrogen-fixing, symbiotic root-nodule forming bacterium Bradyrhizobium japonicum USDA 110 contained gammacerane derivatives next to triterpenoids of the hopane series. Diploptene, diplopterol, 2 beta-methyldiplopterol, aminobacteriohopanetriol and adenosylhopane were accompanied by tetrahymanol and the corresponding novel methylated homologues 2 beta-methyltetrahymanol, 20 alpha-methyltetrahymanol, and 2 beta,20 alpha-dimethyltetrahymanol. Incorporation of [(2)H(3)]methyl-L-methionine indicated that the additional methyl groups originated from methionine, probably with S-adenosylmethionine acting as methyl donor, with retention of the three deuterium atoms. The simultaneous presence of hopane and gammacerane derivatives seems a characteristic feature of the genus Bradyrhizobium and the phylogenetically closely related Rhodopseudomonas palustris.

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Hopanoid lipids in Bradyrhizobium and other plant-associated bacteria and cloning of the Bradyrhizobium japonicum squalene-hopene cyclase gene

Cited by 6 publications

References 18 publications

Squalene-Hopene Cyclases

Squalene-Hopene Cyclases

Hopanoids are formed during transition from substrate to aerial hyphae in Streptomyces coelicolor A3(2)

Novel methylated triterpenoids of the gammacerane series from the nitrogen‐fixing bacterium Bradyrhizobium japonicum USDA 110

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