Proc Natl Acad Sci U S A. 2007 Sep 18;104(38):15099-104. Epub 2007 Sep 11.

Biosynthesis of 2-methylbacteriohopanepolyols by an anoxygenic phototroph.

Rashby SE, Sessions AL, Summons RE, Newman DK.

Source

Divisions of Geological and Planetary Sciences and Biology, California Institute of Technology and Howard Hughes Medical Institute, Pasadena, CA 91125, USA.

Abstract

Sedimentary 2-methyhopanes have been used as biomarker proxies for cyanobacteria, the only known bacterial clade capable of oxygenic photosynthesis and the only group of organisms found thus far to produce abundant 2-methylbacteriohopanepolyols (2-MeBHPs). Here, we report the identification of significant quantities of 2-MeBHP in two strains of the anoxygenic phototroph Rhodopseudomonas palustris. Biosynthesis of 2-MeBHP can occur in the absence of O(2), deriving the C-2 methyl group from methionine. The relative abundance of 2-MeBHP varies considerably with culture conditions, ranging from 13.3% of total bacteriohopanepolyol (BHP) to trace levels of methylation. Analysis of intact BHPs reveals the presence of methylated bacteriohopane-32,33,34,35-tetrol but no detectable methylation of 35-aminobacteriohopane-32,33,34-triol. Our results demonstrate that an anoxygenic photoautotroph is capable of generating 2-MeBHPs and show that the potential origins of sedimentary 2-methylhopanoids are more diverse than previously thought.

PMID:: 17848515; [PubMed - indexed for MEDLINE]
PMCID: PMC1986619

Free PMC Article

Images from this publication.See all images (4) Free text

Publication Types, MeSH Terms, Substances

Publication Types

MeSH Terms

Substances

LinkOut - more resources

Full Text Sources

Other Literature Sources

COS Scholar Universe

Supplemental Content

Related citations

Identification of a methylase required for 2-methylhopanoid production and implications for the interpretation of sedimentary hopanes. [Proc Natl Acad Sci U S A. 2010]
Identification of a methylase required for 2-methylhopanoid production and implications for the interpretation of sedimentary hopanes.
Welander PV, Coleman ML, Sessions AL, Summons RE, Newman DK. Proc Natl Acad Sci U S A. 2010 May 11; 107(19):8537-42. Epub 2010 Apr 26.
Hopanoids play a role in membrane integrity and pH homeostasis in Rhodopseudomonas palustris TIE-1. [J Bacteriol. 2009]
Hopanoids play a role in membrane integrity and pH homeostasis in Rhodopseudomonas palustris TIE-1.
Welander PV, Hunter RC, Zhang L, Sessions AL, Summons RE, Newman DK. J Bacteriol. 2009 Oct; 191(19):6145-56. Epub 2009 Jul 10.
Novel methylated triterpenoids of the gammacerane series from the nitrogen-fixing bacterium Bradyrhizobium japonicum USDA 110. [Eur J Biochem. 2001]
Novel methylated triterpenoids of the gammacerane series from the nitrogen-fixing bacterium Bradyrhizobium japonicum USDA 110.
Bravo JM, Perzl M, Härtner T, Kannenberg EL, Rohmer M. Eur J Biochem. 2001 Mar; 268(5):1323-31.
Review Molecular-organization and biosynthesis of pigment-protein complexes of Rhodopseudomonas capsulata. [Ann Microbiol (Paris). 1983]
Review Molecular-organization and biosynthesis of pigment-protein complexes of Rhodopseudomonas capsulata.
Drews G, Peters J, Dierstein R. Ann Microbiol (Paris). 1983 Jul-Aug; 134B(1):151-8.
Review Effects of shallow-water hydrothermal venting on biological communities of coastal marine ecosystems of the western Pacific. [Adv Mar Biol. 2006]
Review Effects of shallow-water hydrothermal venting on biological communities of coastal marine ecosystems of the western Pacific.
Tarasov VG. Adv Mar Biol. 2006; 50:267-421.

See reviews... See all...

Cited by 5 PubMed Central articles

Significant natural product biosynthetic potential of actinorhizal symbionts of the genus frankia, as revealed by comparative genomic and proteomic analyses. [Appl Environ Microbiol. 2011]
Significant natural product biosynthetic potential of actinorhizal symbionts of the genus frankia, as revealed by comparative genomic and proteomic analyses.
Udwary DW, Gontang EA, Jones AC, Jones CS, Schultz AW, Winter JM, Yang JY, Beauchemin N, Capson TL, Clark BR, et al. Appl Environ Microbiol. 2011 Jun; 77(11):3617-25. Epub 2011 Apr 15.
Identification of a methylase required for 2-methylhopanoid production and implications for the interpretation of sedimentary hopanes. [Proc Natl Acad Sci U S A. 2010]
Identification of a methylase required for 2-methylhopanoid production and implications for the interpretation of sedimentary hopanes.
Welander PV, Coleman ML, Sessions AL, Summons RE, Newman DK. Proc Natl Acad Sci U S A. 2010 May 11; 107(19):8537-42. Epub 2010 Apr 26.
Hopanoids play a role in membrane integrity and pH homeostasis in Rhodopseudomonas palustris TIE-1. [J Bacteriol. 2009]
Hopanoids play a role in membrane integrity and pH homeostasis in Rhodopseudomonas palustris TIE-1.
Welander PV, Hunter RC, Zhang L, Sessions AL, Summons RE, Newman DK. J Bacteriol. 2009 Oct; 191(19):6145-56. Epub 2009 Jul 10.

See all...

Related information

Related Citations
Calculated set of PubMed citations closely related to the selected article(s) retrieved using a word weight algorithm. Related articles are displayed in ranked order from most to least relevant, with the “linked from” citation displayed first.
References for this PMC Article
Citation referenced in PubMed article. Only valid for PubMed citations that are also in PMC.
Substance (MeSH Keyword)
PubChem chemical substance (submitted) records that are classified under the same Medical Subject Headings (MeSH) controlled vocabulary as the current articles.
Free in PMC
Free full text articles in PMC
Cited in PMC
Full-text articles in the PubMed Central Database that cite the current articles.

Recent activity

Clear Turn Off Turn On

Biosynthesis of 2-methylbacteriohopanepolyols by an anoxygenic phototroph.
Biosynthesis of 2-methylbacteriohopanepolyols by an anoxygenic phototroph.
Proc Natl Acad Sci U S A. 2007 Sep 18 ;104(38):15099-104. Epub 2007 Sep 11 .

PubMed
Reproducibility of the 1998 World Health Organization/International Society of U...
Reproducibility of the 1998 World Health Organization/International Society of Urologic Pathology classification of papillary urothelial neoplasms of the urinary bladder.
Virchows Arch. 2003 Dec ;443(6):734-40. Epub 2003 Oct 8 .

PubMed
An endothelial laminin isoform, laminin 8 (alpha4beta1gamma1), is secreted by bl...
An endothelial laminin isoform, laminin 8 (alpha4beta1gamma1), is secreted by blood neutrophils, promotes neutrophil migration and extravasation, and protects neutrophils from apoptosis.
Blood. 2004 Sep 15 ;104(6):1859-66. Epub 2004 Jun 1 .

PubMed
Interleukin-6 and transforming growth factor-beta 1 control expression of cathep...
Interleukin-6 and transforming growth factor-beta 1 control expression of cathepsins B and L in human lung epithelial cells.
J Interferon Cytokine Res. 2001 Jan ;21(1):11-9.

PubMed
Intravenous nutrient therapy: the "Myers' cocktail".
Intravenous nutrient therapy: the "Myers' cocktail".
Altern Med Rev. 2002 Oct ;7(5):389-403.

PubMed

Your browsing activity is empty.

Activity recording is turned off.

Turn recording back on

PubMed

Display Settings:

Send to: