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  "author": "Darci Rush (Royal Netherlands Institute for Sea 
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  "author": "Darci Rush (Royal Netherlands Institute for Sea 
            
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Research)",
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Research)",
            
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  "author_email": "darci.rush@nioz.nl",
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  "author_email": "darci.rush@nioz.nl",
            
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  "code": "7b.b.7j",
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  "code": "7b.b.7j",
            
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  "contributor": "Royal Netherlands Institute for Sea Research 
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  "contributor": "Royal Netherlands Institute for Sea Research 
            
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(NIOZ)",
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(NIOZ)",
            
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  "creator_user_id": "04853165-3f89-4016-9300-1ed632a64052",
            
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  "creators": 
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  "creators": 
            
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e\":\"Rush\",\"orcid\":\"0000-0002-6567-4116\",\"affiliation\":\"Royal 
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e\":\"Rush\",\"orcid\":\"0000-0002-6567-4116\",\"affiliation\":\"Royal 
            
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Netherlands Institute for Sea 
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Netherlands Institute for Sea 
            
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e,\"contactemailaddress\":\"darci.rush@nioz.nl\",\"formatted\":\"Darci 
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e,\"contactemailaddress\":\"darci.rush@nioz.nl\",\"formatted\":\"Darci 
            
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Rush - Royal Netherlands Institute for Sea Research - ORCID: 
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Rush - Royal Netherlands Institute for Sea Research - ORCID: 
            
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0000-0002-6567-4116 - Corresponding Author - darci.rush@nioz.nl\"}]",
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0000-0002-6567-4116 - Corresponding Author - darci.rush@nioz.nl\"}]",
            
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  "dataset_persistent_id": "DOI:10.25850/nioz/7b.b.7j",
            
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  "deposit_date": "2025-11-27",
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  "deposit_date": "2025-11-27",
            
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  "depositor": "Darci Rush (darci.rush@nioz.nl)",
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  "depositor": "Darci Rush (darci.rush@nioz.nl)",
            
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  "distribution_date": "2025-11-27",
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  "distribution_date": "2025-11-27",
            
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  "distributor": "Research Data Management(NIOZ Royal Netherlands 
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  "distributor": "Research Data Management(NIOZ Royal Netherlands 
            
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Institute for Sea Research)",
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Institute for Sea Research)",
            
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  "doi_date_published": "2025-11-27T11:14:32.465535",
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  "doi_date_published": "2025-11-27T11:14:32.465535",
            
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  "license_title": null,
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  "maintainer": "Darci",
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  "maintainer": "Darci",
            
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  "maintainer_email": "darci.rush@nioz.nl",
            
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  "name": "darci-rush",
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  "name": "darci-rush",
            
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  "notes": "Anaerobic ammonium oxidation (anammox) is an important 
31
  "notes": "Anaerobic ammonium oxidation (anammox) is an important 
            
32
process in modern global nitrogen cycling. However, the contribution 
32
process in modern global nitrogen cycling. However, the contribution 
            
33
of anammox to ancient nitrogen biogeochemical cycles cannot currently 
33
of anammox to ancient nitrogen biogeochemical cycles cannot currently 
            
34
be accounted for because the most characteristic lipid biomarkers of 
34
be accounted for because the most characteristic lipid biomarkers of 
            
35
anammox bacteria, ladderane lipids containing concatenated series of 
35
anammox bacteria, ladderane lipids containing concatenated series of 
            
36
cyclobutane moieties, do not preserve as such into the catagenetic 
36
cyclobutane moieties, do not preserve as such into the catagenetic 
            
37
window in the sedimentary record. Alternative lipid biomarkers that 
37
window in the sedimentary record. Alternative lipid biomarkers that 
            
38
are more resistant to degradation are needed by the geochemical 
38
are more resistant to degradation are needed by the geochemical 
            
39
community to investigate the presence anammox in high maturity 
39
community to investigate the presence anammox in high maturity 
            
40
sediments and inform on past marine oxygen depletion, nitrogen 
40
sediments and inform on past marine oxygen depletion, nitrogen 
            
41
cycling, and the formation of organic rich sediment such as black 
41
cycling, and the formation of organic rich sediment such as black 
            
42
shale deposits. Here, we describe novel cyclic hydrocarbons produced 
42
shale deposits. Here, we describe novel cyclic hydrocarbons produced 
            
43
by the simulated thermal maturation of anammox bacterial biomass. 
43
by the simulated thermal maturation of anammox bacterial biomass. 
            
44
Alkyl branched tricyclic hydrocarbons were present in pyrolysates 
44
Alkyl branched tricyclic hydrocarbons were present in pyrolysates 
            
45
generated by hydrous pyrolysis experiments at temperatures >200 
45
generated by hydrous pyrolysis experiments at temperatures >200 
            
46
\u00b0C, in the window of oil generation. Two-dimensional gas 
46
\u00b0C, in the window of oil generation. Two-dimensional gas 
            
47
chromatography-mass spectrometry revealed that these artificial 
47
chromatography-mass spectrometry revealed that these artificial 
            
48
maturation experiments generated multiple series of cyclic 
48
maturation experiments generated multiple series of cyclic 
            
49
hydrocarbons. A representative product was isolated by preparative gas 
49
hydrocarbons. A representative product was isolated by preparative gas 
            
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chromatography, but was shown to be composed of two co-eluting 
50
chromatography, but was shown to be composed of two co-eluting 
            
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components. Their structures were partially identified, by way of 
51
components. Their structures were partially identified, by way of 
            
52
two-dimensional nuclear magnetic resonance (NMR), to be 
52
two-dimensional nuclear magnetic resonance (NMR), to be 
            
53
4-octyl-tricyclo[7.3.0.02,8]dodecanes with the three concatenated 
53
4-octyl-tricyclo[7.3.0.02,8]dodecanes with the three concatenated 
            
54
rings comprising of 7, 4, and 5 carbons. This ring assemblage was 
54
rings comprising of 7, 4, and 5 carbons. This ring assemblage was 
            
55
further confirmed through NMR and mass spectral comparisons with four 
55
further confirmed through NMR and mass spectral comparisons with four 
            
56
synthesized model compounds. The isolated components had a stable 
56
synthesized model compounds. The isolated components had a stable 
            
57
carbon isotopic composition similarly depleted in 13C as the ladderane 
57
carbon isotopic composition similarly depleted in 13C as the ladderane 
            
58
fatty acids of the original anammox biomass, consistent with a 
58
fatty acids of the original anammox biomass, consistent with a 
            
59
ladderane lipid source. The C20 hydrocarbons could have formed from 
59
ladderane lipid source. The C20 hydrocarbons could have formed from 
            
60
thermal ether cleavage and ring-opening of the C20-[5]- or 
60
thermal ether cleavage and ring-opening of the C20-[5]- or 
            
61
[3]-ladderane glycerol ether, common membrane lipids of anammox 
61
[3]-ladderane glycerol ether, common membrane lipids of anammox 
            
62
bacteria. Molecular mechanic calculations were used to generate the 
62
bacteria. Molecular mechanic calculations were used to generate the 
            
63
relative structural stability of stereoisomers and the possible 
63
relative structural stability of stereoisomers and the possible 
            
64
conversion steps to the formation of these components. These indicated 
64
conversion steps to the formation of these components. These indicated 
            
65
that the 7-4-5 components were the result of the breakdown and 
65
that the 7-4-5 components were the result of the breakdown and 
            
66
rearrangement of bonds in the cyclobutane rings from 
66
rearrangement of bonds in the cyclobutane rings from 
            
67
biosynthetically-derived 4-4-4-4-4 ladderane lipids. These components 
67
biosynthetically-derived 4-4-4-4-4 ladderane lipids. These components 
            
68
were not detected in thermally mature sediment and rocks screened 
68
were not detected in thermally mature sediment and rocks screened 
            
69
using conventional GC-MS analysis, however, by using more advanced 
69
using conventional GC-MS analysis, however, by using more advanced 
            
70
chromatography methods these lipids may be still be helpful biomarkers 
70
chromatography methods these lipids may be still be helpful biomarkers 
            
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for assessing past anammox in ancient sediments and crude oils.",
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for assessing past anammox in ancient sediments and crude oils.",
            
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