Analysis of non-derivatized bacteriohopanepolyols using UHPLC-HRMS reveals great structural diversity in environmental lipid assemblages

Hopmans, Ellen C.; Smit, Nadine T.; Schwartz-Narbonne, Rachel; Damsté, Jaap S. Sinninghe; Rush, Darci

doi:10.1016/j.orggeochem.2021.104285

Cited by 11 publications

(17 citation statements)

References 63 publications

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“…The recently described propenolamine-BHT, ethenolamine-BHT, ethenolamine-255 BHpentol, and ethenolamine-BHhexol (Fig. 3) were identified in our samples after Hopmans et al (2021). In addition, we putatively identified unsaturated versions of ethenolamine-BHT (Appendix B4, Fig.…”

supporting

confidence: 55%

“…Samples were analyzed following the methods described in Hopmans et al (2021). Briefly, samples were analyzed on an Agilent 1290 Infinity I UHPLC coupled to a quadrupole-orbitrap HRMS equipped with an Ion Max source and heated ESI probe (HESI) (ThermoFisher Scientific, Waltham, MA).…”

Section: Uhplc/hrms Analysismentioning

confidence: 99%

“…Previously, "soil-marker BHPs" included only adenosylhopane, N1-methylinosylhopane (i.e., type-2 adenosylhopane after Hopmans et al, 2021), adenosylhopaneHG-Me (i.e., type-3 adenosylhopane after Hopmans et 190 al., 2021) .…”

Section: Rsoil Indexmentioning

confidence: 99%

“…Recent studies and advancements in BHP analysis highlight the wide distribution and diversity of BHPs in both 40 marine and terrestrial environments Pearson et al, 2009;Sáenz et al, 2011;Kusch et al, 2019;Hopmans et al, 2021). Bacteriohopanetetrol (BHT), BHT-cyclitol ether (CE), and aminotriol, for instance, are ubiquitous in environmental samples and culture studies, and are not associated with any specific organisms or environments (e.g., Talbot et al, 2003;Zhu et al, 2011).…”

Section: Introduction 30mentioning

confidence: 99%

“…Nucleoside BHPs were particularly diverse in the water column SPM and surface sediments in lakes Empadadas, São Jorge, and Lomba. We identified fourteen nucleoside BHPs, including three inosylhopanes, described by Hopmans et al (2021;Appendix B, Fig. B2 & B3).…”

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confidence: 99%

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Distributions of bacteriohopanepolyols in lakes and coastal lagoons of the Azores Archipelago

Richter

Hopmans²,

Mitrović³

et al. 2023

Preprint

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Abstract. Bacteriohopanepolyols (BHPs) are a diverse class of lipids produced by bacteria across a wide range of environments. In this study, we aim to further identify BHPs related to ecological niches and/or specific bacteria by characterizing the distribution of BHPs in suspended particulate matter (SPM) of the water column and in sediments in a range of lakes and coastal lagoons from the Azores Archipelago, as well as in a co-culture enriched for methanotrophs. Sediment samples from Azorean lakes with low oxygen conditions during the summer months (i.e., Azul, Verde, Funda, and Negra) contain relatively high abundances of BHPs that are typically associated with methane-oxidizing (methanotrophic) bacteria (i.e., aminotetrol, aminopentol, and methylcarbamate-aminopentol), as well as the ethenolamine-BHPs (i.e., ethenolamine-BHpentol and ethenolamine-BHhexol) and the formylated aminoBHPs. Both ethenolamine-BHPs and formylated aminoBHPs were also detected in a co-culture enriched for methanotrophs obtained from a lake. In the SPM of all water columns, bacteriohopanetetrol (BHT), BHT-cyclitol ether, and aminotriol are the dominant BHPs. In SPM from Lake Funda, nucleoside BHPs (i.e., Me-adenosylhopaneHG-diMe, N1-methylinosylhopane, 2Me-N1-inosylhopane, and Me-N1-inosylhopane) are present in low abundance or absent under oxic conditions but increase in concentration near the chemocline, suggesting potential in situ production of these nucleoside BHPs rather than an allochthonous origin. In contrast, sediments from shallow, well-mixed lakes (i.e., Empadadas, São Jorge, and Lomba) contain higher abundances of adenosylhopane and N1-methylinosylhopane, which likely originate from bacteria living in nearby soils. In the coastal lagoons, Cubres East and West, methoxylated-BHTs were detected, and higher abundances of ethenolamine-BHT were observed. This study highlights the diversity of BHPs in lakes and coastal lagoons and their potential as taxonomic markers for bacteria associated with certain ecological niches, which can be preserved in sedimentary records.

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supporting

confidence: 55%

Section: Uhplc/hrms Analysismentioning

confidence: 99%

Section: Rsoil Indexmentioning

confidence: 99%

Section: Introduction 30mentioning

confidence: 99%

mentioning

confidence: 99%

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Distributions of bacteriohopanepolyols in lakes and coastal lagoons of the Azores Archipelago

Richter

Hopmans²,

Mitrović³

et al. 2023

Preprint

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Characterization of HpnG as a Purine Nucleoside Phosphorylase in Bacteriohopanepolyol Biosynthesis^†

Li,

Zhu,

Zhong

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryHpnG plays a crucial role in the production of ribosylhopane, a key intermediate in the biosynthesis of bacteriohopanepolyol. Despite early extensive studies, the precise function of HpnG has remained elusive. Here, we report functional characterization of HpnG as a purine nucleoside phosphorylase, which converts adenosylhopane to phosphoribosylhopane in the presence of phosphate. HpnG demonstrates broad substrate specificity and impressive stability, making it a valuable enzymatic tool for applications in nucleoside processing and related biotechnology.

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Marine nitrogen cycling dynamics under altering redox conditions: Insights from deposition of sapropels S1 and the ambiguous S2 in the Eastern Mediterranean Sea

Kemenade

Cutmore

Hennekam

et al. 2023

Geochimica et Cosmochimica Acta

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Analysis of non-derivatized bacteriohopanepolyols using UHPLC-HRMS reveals great structural diversity in environmental lipid assemblages

Cited by 11 publications

References 63 publications

Distributions of bacteriohopanepolyols in lakes and coastal lagoons of the Azores Archipelago

Distributions of bacteriohopanepolyols in lakes and coastal lagoons of the Azores Archipelago

Characterization of HpnG as a Purine Nucleoside Phosphorylase in Bacteriohopanepolyol Biosynthesis^†

Marine nitrogen cycling dynamics under altering redox conditions: Insights from deposition of sapropels S1 and the ambiguous S2 in the Eastern Mediterranean Sea

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Analysis of non-derivatized bacteriohopanepolyols using UHPLC-HRMS reveals great structural diversity in environmental lipid assemblages

Cited by 11 publications

References 63 publications

Distributions of bacteriohopanepolyols in lakes and coastal lagoons of the Azores Archipelago

Distributions of bacteriohopanepolyols in lakes and coastal lagoons of the Azores Archipelago

Characterization of HpnG as a Purine Nucleoside Phosphorylase in Bacteriohopanepolyol Biosynthesis†

Marine nitrogen cycling dynamics under altering redox conditions: Insights from deposition of sapropels S1 and the ambiguous S2 in the Eastern Mediterranean Sea

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Characterization of HpnG as a Purine Nucleoside Phosphorylase in Bacteriohopanepolyol Biosynthesis^†