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{{Short description|Biomarker for human faecal matter}}
{{chembox
{{cs1 config|name-list-style=vanc|display-authors=6}}
⚫ | verifiedrevid = 401967938
{{More footnotes|date=March 2019}}
⚫ | Name = Coprostanol
{{Chembox
⚫ | ImageFile = coprostanol.png
| Verifiedfields = changed
| ImageName = Coprostanol
| Watchedfields = changed
⚫ | IUPACName = 5β-cholestan-3β-ol
⚫ | verifiedrevid = 401969604
⚫ | OtherNames = 5β-coprostanol<br />coprostanol
⚫ | Name = Coprostanol
⚫ | Section1 = {{Chembox Identifiers
⚫ | ImageFile = coprostanol.png
⚫ | SMILES = O4CC3((CC21CC(1(C)CC23)(C)CCCC(C)C)C4)C
| ImageSize = 260
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ImageAlt = Skeletal formula of coprostanol
⚫ | ChemSpiderID = 19951861
| ImageFile1 = Coprostanol 3D ball.png
| ImageSize1 = 260
| ImageAlt1 = Ball-and-stick model of the coprostanol molecule
⚫ | IUPACName = 5β-cholestan-3β-ol
⚫ | OtherNames = 5β-coprostanol<br />coprostanol
⚫ | Section1 = {{Chembox Identifiers
⚫ | SMILES = O4CC3((CC21CC(1(C)CC23)(C)CCCC(C)C)C4)C
| PubChem = 221122
⚫ | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
⚫ | ChemSpiderID = 191826
| EC_number = 206-638-8
| ChEBI = 89519
| ChEMBL = 2048325
| InChI = 1/C27H48O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-25,28H,6-17H2,1-5H3/t19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1 | InChI = 1/C27H48O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-25,28H,6-17H2,1-5H3/t19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1
| InChIKey = QYIXCDOBOSTCEI-NWKZBHTNBU | InChIKey = QYIXCDOBOSTCEI-NWKZBHTNBU
⚫ | StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| InChI1 = 1/C27H48O/c1-18(2)8-6-9-19(3)22-14-15-23-21-13-12-20-10-7-11-25(28)27(20,5)24(21)16-17-26(22,23)4/h18-25,28H,6-17H2,1-5H3/t19-,20+,21+,22-,23+,24+,25?,26-,27+/m1/s1 | StdInChI = 1S/C27H48O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-25,28H,6-17H2,1-5H3/t19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1
| InChIKey1 = FVBJWENATSMJIB-YGNXBUKOBH
⚫ | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| SMILES1 = CC(C)CCC(C)4CC34(C)CC13CC2CCCC(O)12C
⚫ | StdInChIKey = QYIXCDOBOSTCEI-NWKZBHTNSA-N
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C27H48O/c1-18(2)8-6-9-19(3)22-14-15-23-21-13-12-20-10-7-11-25(28)27(20,5)24(21)16-17-26(22,23)4/h18-25,28H,6-17H2,1-5H3/t19-,20+,21+,22-,23+,24+,25?,26-,27+/m1/s1
⚫ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChIKey = FVBJWENATSMJIB-YGNXBUKOSA-N
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 360-68-9 | CASNo = 360-68-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = PPT67I3S74
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| C = 27 | H = 48 | O = 1
| Formula = {{carbon}}<sub>27</sub>{{hydrogen}}<sub>48</sub>{{oxygen}}
⚫ | Appearance =
| MolarMass = 388.6756 g/mol
⚫ | Density =
⚫ | Appearance =
| Solubility = Poorly soluble
⚫ | Density =
| Solubility = | MeltingPtC = 102
| MeltingPt = 102 °C | BoilingPt =
| BoilingPt =
}} }}
| Section7 = {{Chembox Hazards | Section7 = {{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
| MainHazards = | MainHazards =
| FlashPt = non-flammable | FlashPt = Non-flammable
| RPhrases =
| SPhrases =
}} }}
| Section8 = {{Chembox Related | Section8 = {{Chembox Related
| Function = Stanols | OtherFunction_label = Stanols
| OtherFunctn = ]<br />]<br />] | OtherFunction = ]<br />]<br />]
}} }}
}} }}


'''5β-Coprostanol''' ('''5β-cholestan-3β-ol''') is a 27 ] ] formed from the ] of ] (cholest-5en-3β-ol) in the ] of most higher animals and birds. This compound has frequently been used as a ] for the presence of ] ] matter in the ]. '''5β-Coprostanol''' ('''5β-cholestan-3β-ol''') is a 27-] ] formed from the net reductive ] of ] (cholest-5en-3β-ol) in the ] of most higher animals and birds. This compound has frequently been used as a ] for the presence of ] ] matter in the ]. 5β-coprostanol is thought to be exclusively ]l in origin.


==Chemical properties== ==Chemical properties==

===Solubility === ===Solubility ===
5β-coprostanol has a low water ] and consequently a high ] (log Kow = 8.82). This means that in most environmental systems, 5β-coprostanol will be associated with the solid phase. 5β-coprostanol has a low water ], and consequently a high ] {{nowrap|(log K<sub>ow</sub> {{=}} 8.82)}}. In other words, 5β-coprostanol has an affinity nearly 1 billion times higher for ] than for ]. This means that in most environmental systems, 5β-coprostanol will be associated with the ].


===Degradation=== ===Degradation===
In ] sediments and soils, 5β-coprostanol is stable for many hundreds of years enabling it to be used as an indicator of past faecal discharges. As such, records of 5β-coprostanol from paleo-environmental archives have been used to further constrain the timing of human settlements in a region, as well as reconstruct relative changes in human populations and agricultural activities over several thousand years.<ref name=":0">{{cite journal | vauthors = D'Anjou RM, Bradley RS, Balascio NL, Finkelstein DB | title = Climate impacts on human settlement and agricultural activities in northern Norway revealed through sediment biogeochemistry | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 109 | issue = 50 | pages = 20332–20337 | date = December 2012 | pmid = 23185025 | pmc = 3528558 | doi = 10.1073/pnas.1212730109 | doi-access = free | bibcode = 2012PNAS..10920332D }}</ref>
In ] sediments and soils, 5β-coprostanol is stable for many hundreds of years enabling it to be used as an indicator of past faecal discharges.


===Chemical analysis=== ===Chemical analysis===
Since the ] has a ] (-OH) group, it is frequently bound to other ] including ]; most analytical methods, therefore, utilise a strong ] (KOH or NaOH) to ] the ] linkages. Typical extraction ] include 6% KOH in ]. The free ] and ] (saturated sterols) are then separated from the ] by partitioning into a less polar solvent (''e.g''. ]). Prior to analysis, the hydroxyl group is frequently derivatised with ] (bis-trimethyl silyl trifluoroacetamide) to replace the hydrogen with the less exchangeable trimethylsilyl (TMS) group. Instrumental analysis is frequently conducted on ] (GC) with either a ] (FID) or ] (MS). The ] for 5β-coprostanol - TMS ether can be seen in the figure.<br /> Since the ] has a ] (-OH) group, it is frequently bound to other ] including ]; most analytical methods, therefore, utilise a strong ] (KOH or NaOH) to ] the ] linkages. Typical extraction ] include 6% KOH in ]. The free ] and ] (saturated sterols) are then separated from the ] by partitioning into a less polar solvent such as ]. Prior to analysis, the hydroxyl group is frequently derivatised with ] (bis-trimethyl silyl trifluoroacetamide) to replace the hydrogen with the less exchangeable trimethylsilyl (TMS) group. Instrumental analysis is frequently conducted on ] (GC) with either a ] (FID) or ] (MS). The ] for 5β-coprostanol - TMS ether can be seen in the figure. Alternatively, liquid-chromatography mass spectrometry (LC-MS) techniques that employ atmospheric pressure chemical ionization (APCI) may also be employed to detect coprostanol under positive mode.<br />
] ]


===Isomers=== ===Isomers===
As well as the faecally derived stanol, two other isomers can be identified in the environment; 5α-cholestanol (5α-cholestan-3β-ol) and epi-coprostanol (5β-cholestan-3α-ol). As well as the faecally derived stanol, two other isomers can be identified in the environment; 5α-cholestanol


==Formation and occurrence== ==Formation and occurrence==

===Faecal sources=== ===Faecal sources===
5β-coprostanol is formed by the conversion of cholesterol to coprostanol in the gut of most higher animals by intestinal bacteria. The general scheme for its production via a ] intermediate can be seen in the figure proposed by Grimalt et al., 1990. 5β-coprostanol is formed by the conversion of ] to coprostanol in the gut of most higher animals by intestinal ]. It is generally accepted that the metabolism of cholesterol to coprostanol by gut bacteria proceeds in an indirect manner via ketone intermediates, rather than direct reduction of the Δ<sup>5,6</sup> double bond.<ref>{{cite journal | vauthors = Kenny DJ, Plichta DR, Shungin D, Koppel N, Hall AB, Fu B, Vasan RS, Shaw SY, Vlamakis H, Balskus EP, Xavier RJ | title = Cholesterol Metabolism by Uncultured Human Gut Bacteria Influences Host Cholesterol Level | journal = Cell Host & Microbe | volume = 28 | issue = 2 | pages = 245–257.e6 | date = August 2020 | pmid = 32544460 | pmc = 7435688 | doi = 10.1016/j.chom.2020.05.013 }}</ref> be seen in the figure proposed by Grimalt et al., (1990).


] ]


{| class="wikitable" {| class="wikitable"
|+ A list of the animals in which 5β-coprostanol has been identified in the faecal matter. |+ List of animals in which 5β-coprostanol has been identified in faecal matter.
|- |-
!Animals Producing Coprostanol !Animals producing coprostanol
!Animals NOT Producing Coprostanol !Animals NOT producing coprostanol
|- |-
||Humans||dogs ||Humans||Dogs
|- |-
||Cattle||? ||Cattle||?
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===5β-coprostanol / cholesterol ratio=== ===5β-coprostanol / cholesterol ratio===
Since 5β-coprostanol is formed from cholesterol in the ] ], the ratio of the product over reactant can be used to indicate the degree of faecal matter in samples. Raw untreated sewage typically has a 5β-coprostanol / cholesterol ratio of ~10 which decreases through a sewage treatment plant (STP) such that in the discharged liquid wastewaters the ratio is ~2. Undiluted STP wastewaters may be identified by this high ratio. As the faecal matter is dispersed in the environment, the ratio will decrease as more (non-faecal) cholesterol from animals is encountered. Grimalt & Albaiges have suggested that samples with a 5β-coprostanol / cholesterol greater than 0.2 may be considered as contaminated by faecal material. Since 5β-coprostanol is formed from ] in the ] ], the ratio of the product over reactant can be used to indicate the degree of faecal matter in samples. Raw untreated sewage typically has a 5β-coprostanol / cholesterol ratio of ~10 which decreases through a sewage treatment plant (STP) such that in the discharged liquid wastewaters the ratio is ~2. Undiluted STP wastewaters may be identified by this high ratio. As the faecal matter is dispersed in the environment, the ratio will decrease as more (non-faecal) cholesterol from animals is encountered. Grimalt & Albaiges (<u>year?</u>){{Citation needed|date=February 2024}} have suggested that samples with a 5β-coprostanol / cholesterol greater than 0.2 may be considered as contaminated by faecal material.


===5β-Coprostanol / (5β-Coprostanol + 5α-Cholestanol) Ratio=== ===5β-coprostanol / (5β-coprostanol + 5α-cholestanol) ratio===
Another measure of human faecal contamination is the proportion of the two 3β-ol ]s in the 5β form. 5α-cholestanol is formed naturally in the environment by bacteria and generally does not have a faecal origin. Samples with ratios greater than 0.7 may be contaminated with human faecal matter; samples with values less than 0.3 may be considered uncontaminated. Samples with ratios between these two cut-offs can not readily be categorised on the basis of this ratio alone.<br /> Another measure of human faecal contamination is the proportion of the two 3β-ol ]s of the saturated sterol form. 5α-cholestanol is formed naturally in the environment by bacteria and generally does not have a faecal origin. Samples with ratios greater than 0.7 may be contaminated with human faecal matter; samples with values less than 0.3 may be considered uncontaminated. Samples with ratios between these two cut-offs can not readily be categorised on the basis of this ratio alone.<br />
] ]


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===5β-coprostanol / 24-ethyl coprostanol=== ===5β-coprostanol / 24-ethyl coprostanol===
Herbivores such as cows and sheep consume terrestrial plant matter (grass) which contains β-sitosterol as the principal sterol. β-sitosterol is the 24-ethyl derivative of cholesterol and can be used as a biomarker for terrestrial plant matter (see section). In the gut of these animals, bacteria biohydrogenate the double bond in the 5 position to create 24-ethyl coprostanol and so this compound can be used as a biomarker for faecal matter from herbivores. Typical values in different source materials can be seen in the table after Gilpin. Herbivores such as cows and sheep consume terrestrial plant matter (grass) which contains β-sitosterol as the principal sterol. β-sitosterol is the 24-ethyl derivative of cholesterol and can be used as a biomarker for terrestrial plant matter (see section). In the gut of these animals, bacteria biohydrogenate the double bond in the 5 position to create 24-ethyl coprostanol and so this compound can be used as a biomarker for faecal matter from herbivores. Typical values in different source materials can be seen in the table after Gilpin (<u>year?</u>).{{Citation needed|date=February 2024}}


{| {|
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!5β-cop / 24-ethyl cop !5β-cop / 24-ethyl cop
|- |-
|Septic tanks | Septic tanks
|2.9 – 3.7 | 2.9 – 3.7
|- |-
|Community wastewater | Community wastewater
|2.6 – 4.1 | 2.6 – 4.1
|- |-
|Abattoir – sheep, cattle | Abattoir – sheep, cattle
|0.5 – 0.9 | 0.5 – 0.9
|- |-
|Dairy shed wash-down | Dairy shed wash-down
|0.2 | 0.2
|} |}


===Epi-coprostanol / 5β-coprostanol=== ===Epi-coprostanol / 5β-coprostanol===
During sewage treatment, 5β-coprostanol may be converted to 5β-cholestan-3α-ol form, epi-coprostanol. There is also a slow conversion of 5β-coprostanol to epi-coprostanol in the environment and so this ratio will indicate either the degree of treatment of sewage or its age in the environment. A cross-plot of the 5β-coprostanol / cholesterol ratio with the epi-coprostanol / 5β-coprostanol can indicate both faecal contamination and treatment.<br /> During sewage treatment, 5β-coprostanol may be converted to 5β-cholestan-3α-ol form, epi-coprostanol. There is also a slow conversion of 5β-coprostanol to epi-coprostanol in the environment and so this ratio will indicate either the degree of treatment of sewage or its age in the environment. A ] of the 5β-coprostanol / cholesterol ratio with the epi-coprostanol / 5β-coprostanol can indicate both faecal contamination and treatment.<br />
] ]

==Related markers== ==Related markers==

===5α-cholestanol / cholesterol=== ===5α-cholestanol / cholesterol===
In the environment, bacteria preferentially produce 5α-cholestan-3β-ol (5α-cholestanol) from cholesterol rather than the 5β isomer. This reaction occurs principally in anaerobic reducing sediments and the 5α-cholestanol / cholesterol ratio may be used as a secondary (process) biomarker for such conditions. No cut-off values have been suggested for this marker and so it is used in a relative sense; the greater the ratio, the more reducing the environment. Reducing environments are frequently associated with areas experiencing high organic matter input; this may include sewage derived discharges. The relationship between reducing conditions and the potential source can be seen in a cross plot with a sewage indicator.<br /> In the environment, bacteria preferentially produce 5α-cholestan-3β-ol (5α-cholestanol) from cholesterol rather than the 5β isomer. This reaction occurs principally in anaerobic reducing sediments and the 5α-cholestanol / cholesterol ratio may be used as a secondary (process) biomarker for such conditions. No cut-off values have been suggested for this marker and so it is used in a relative sense; the greater the ratio, the more reducing the environment. Reducing environments are frequently associated with areas experiencing high organic matter input; this may include sewage derived discharges. The relationship between reducing conditions and the potential source can be seen in a cross plot with a sewage indicator.<br />
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It may be suggested from this relationship that sewage discharges are in part responsible for the anaerobic reducing conditions in the sediments. It may be suggested from this relationship that sewage discharges are in part responsible for the anaerobic reducing conditions in the sediments.


==Use in archaeological studies==
⚫ ==References==
Coprostanol and its derivative epicoprostanol are used in ] and ] studies as indicators of past human activity due to their longevity in soils and strong association with production in the human gut.<ref>{{Cite journal| vauthors = Bull ID, Simpson IA, van Bergen PF, Evershed RP |date=1999|title=Muck 'n' molecules: organic geochemical methods for detecting ancient manuring|url=https://www.cambridge.org/core/journals/antiquity/article/muck-n-molecules-organic-geochemical-methods-for-detecting-ancient-manuring/1240E2A5870732D69B66F40AD114213C|journal=Antiquity|language=en|volume=73|issue=279|pages=86–96|doi=10.1017/S0003598X0008786X|s2cid=56237722 |issn=0003-598X}}</ref><ref>{{Cite journal| vauthors = Sistiaga A, Berna F, Laursen R, Goldberg P |date=2014-01-01|title=Steroidal biomarker analysis of a 14,000 years old putative human coprolite from Paisley Cave, Oregon|url=http://www.sciencedirect.com/science/article/pii/S0305440313003634|journal=Journal of Archaeological Science|language=en|volume=41|pages=813–817|doi=10.1016/j.jas.2013.10.016|bibcode=2014JArSc..41..813S |issn=0305-4403}}</ref> Researchers have used the presence of coprostanol to identify archaeological features such as ]s or landscape activities like ].<ref>{{Cite journal| vauthors = Bethell PH, Goad LJ, Evershed RP, Ottaway J |date= September 1994 |title=The Study of Molecular Markers of Human Activity: The Use of Coprostanol in the Soil as an Indicator of Human Faecal Material|url=http://www.sciencedirect.com/science/article/pii/S0305440384710612|journal=Journal of Archaeological Science|language=en|volume=21|issue=5|pages=619–632|doi=10.1006/jasc.1994.1061|bibcode=1994JArSc..21..619B |issn=0305-4403}}</ref><ref>{{Cite journal| vauthors = Bull ID, Evershed RP, Betancourt PP |date=2001|title=An organic geochemical investigation of the practice of manuring at a Minoan site on Pseira Island, Crete|journal=Geoarchaeology|language=en|volume=16|issue=2|pages=223–242|doi=10.1002/1520-6548(200102)16:2<223::AID-GEA1002>3.0.CO;2-7|issn=1520-6548|doi-access=free|bibcode=2001Gearc..16..223B }}</ref> Variations in the concentration of coprostanol over time can be used to create human population reconstructions within a specific depositional environment.<ref name=":0" /><ref>{{Cite journal| vauthors = White AJ, Stevens LR, Lorenzi V, Munoz SE, Lipo CP, Schroeder S |date=2018-05-01|title=An evaluation of fecal stanols as indicators of population change at Cahokia, Illinois|url=http://www.sciencedirect.com/science/article/pii/S0305440318301006|journal=Journal of Archaeological Science|language=en|volume=93|pages=129–134|doi=10.1016/j.jas.2018.03.009|bibcode=2018JArSc..93..129W |issn=0305-4403}}</ref>
⚫ Mudge, S.M. & Ball, A.S. (2006) Sewage In: Environmental Forensics: A Contaminant Specific Approach Eds. Morrison, R. and Murphy, B. Elsevier, pp533.

⚫ Bethell, P. H., L. J. Goad, Evershed, RP and Ottaway, J. (1994). "The study of molecular markers of human activity: the use of coprostanol in the soil as an indicator of human faecal material." Journal of Archaeological Science 21: 619-632


== See also ==
Bull, I.D., M.J. Lockheart, M.M. Elhmmali, D.J. Roberts, and R.P. Evershed. (2002). "The origin of faeces by means of biomarker detection." Environment International 27(8): 647-654.
*]


⚫ == References ==
{{reflist}}


== Further reading ==
<references/>
{{refbegin}}
⚫ * {{Cite book | vauthors = Mudge SM, Ball AS |year=2006|title=Sewage In: Environmental Forensics: A Contaminant Specific Approach| veditors = Morrison R, Murphy B |publisher=Elsevier |page=533}}
⚫ * {{Cite journal|year=1994|title=The study of molecular markers of human activity: the use of coprostanol in the soil as an indicator of human faecal material|journal=Journal of Archaeological Science|volume= 21|pages= 619–632|doi=10.1006/jasc.1994.1061|issue=5| vauthors = Bethell P |bibcode=1994JArSc..21..619B }}
* {{cite journal | vauthors = Bull ID, Lockheart MJ, Elhmmali MM, Roberts DJ, Evershed RP | title = The origin of faeces by means of biomarker detection | journal = Environment International | volume = 27 | issue = 8 | pages = 647–654 | date = March 2002 | pmid = 11934114 | doi = 10.1016/S0160-4120(01)00124-6 | bibcode = 2002EnInt..27..647B }}
{{refend}}


] ]
] ]
]