Some representative hopanoids: A. Diploptene, also called 22(29)-hopene B. Diplopterol, also called hopan-22-ol, the hydrated cyclomer of diploptene C. Bacteriohopanetetrol (BHT), a common extended hopanoid D. Hopane, the diagenetic product of A and B that results from reducing conditions during deposition and persists in the rock record. The diagenetic product of C would be an extended C35 hopane.
Hopanoids are a diverse subclass of triterpenoids with the same hydrocarbon skeleton as the compound hopane. This group of pentacyclic molecules therefore refers to simple hopenes, hopanols and hopanes, but also to extensively functionalized derivatives such as bacteriohopanepolyols (BHPs) and hopanoids covalently attached to lipid A.[1][2]
The first known hopanoid, hydroxyhopanone, was isolated by two chemists at The National Gallery, London working on the chemistry of dammar gum, a natural resin used as a varnish for paintings.[3] While hopanoids are often assumed to be made only in bacteria, their name actually comes from the abundance of hopanoid compounds in the resin of plants from the genus Hopea. In turn, this genus is named after John Hope, the first Regius Keeper of the Royal Botanic Garden, Edinburgh.
Since their initial discovery in an angiosperm, hopanoids have been found in plasma membranes of bacteria, lichens, bryophytes, ferns, tropical trees and fungi.[4] Hopanoids have stable polycyclic structures that are well-preserved in petroleum reservoirs, rocks and sediment, allowing the diagenetic products of these molecules to be interpreted as biomarkers for the presence of specific microbes and potentially for chemical or physical conditions at the time of deposition.[5] Hopanoids have not been detected in archaea.[6][7]
^Welander PV (August 2019). "Deciphering the evolutionary history of microbial cyclic triterpenoids". Free Radical Biology & Medicine. Early Life on Earth and Oxidative Stress. 140: 270–278. doi:10.1016/j.freeradbiomed.2019.05.002. PMID 31071437.
^Sohlenkamp C, Geiger O (January 2016). "Bacterial membrane lipids: diversity in structures and pathways". FEMS Microbiology Reviews. 40 (1): 133–59. doi:10.1093/femsre/fuv008. PMID 25862689.
^Mills JS, Werner AE (1955-01-01). "The chemistry of dammar resin". Journal of the Chemical Society (Resumed): 3132–3140. doi:10.1039/JR9550003132. ISSN 0368-1769.
^Volkman JK (2005-02-01). "Sterols and other triterpenoids: source specificity and evolution of biosynthetic pathways". Organic Geochemistry. 36 (2): 139–159. doi:10.1016/j.orggeochem.2004.06.013.
^Hunt JM, Philp RP, Kvenvolden KA (2002-09-01). "Early developments in petroleum geochemistry". Organic Geochemistry. 33 (9): 1025–1052. doi:10.1016/S0146-6380(02)00056-6.
^William W. Christie. "The AOCS Lipid Library. Hopanoids". American Oil Chemists' Society. Archived from the original on 2016-03-05. Retrieved 2015-11-17.
^"Hopanoids - AOCS Lipid Library". 2016-03-05. Archived from the original on 2016-03-05. Retrieved 2020-03-06.
an angiosperm, hopanoids have been found in plasma membranes of bacteria, lichens, bryophytes, ferns, tropical trees and fungi. Hopanoids have stable polycyclic...
in the human body. It is also an intermediate in the biosynthesis of hopanoids in many bacteria. Squalene is an important ingredient in some vaccine...
precursor for the formation of many triterpenoids, including bacterial hopanoids and eukaryotic sterols. By definition triterpenoids are triterpenes that...
The rest of the aliphatic chain is non-polar. Cholesterol Ergosterol Hopanoids Hydroxysteroid Phytosterol Steroids Zoosterol "sterol (CHEBI:15889)"....
a variety of other chemical compounds which are collectively known as hopanoids. The first compound of the hopane family to be isolated and characterised...
the hopanoids. These compounds share a common pentacyclic core with title compound hopane, yet they demonstrate great structural diversity. Hopanoids are...
species of bacteria produce hopanoids, more recent studies estimate around 4% of bacteria have the ability to produce hopanoids. Several studies have used...
eukaryotes is conjectured – and the more-common pentacyclic triterpinoid hopanoid framework. Fungal steroids include the ergosterols, which are involved...
archaea. Terpenoid lipids are a group of lipids containing cholesterol, hopanoids, carotenoid, phytane, and bisphytane. Although terpenoids are the main...
Retigeric acid B is a hopanoids chemical compound isolated from Lobaria. Zhang HJ, Ou Y, Lou HX (June 2007). "[Studies on chemical constituents of Lobaria...
VAMP proteins. Phytosterols, such as sitosterol and stigmasterol, and hopanoids serve a similar function in plants and prokaryotes. Homeoviscous adaptation...
Rhodoplanes is a phototrophic genus of bacteria. Rhodoplanes produces hopanoids like diplopterol, tetrahymanol, 2-methyldiplopterol, 2-methyltetrahymanol...
However, many microbes do contain structurally related compounds called hopanoids which likely fulfill the same function. Unlike eukaryotes, bacteria can...
signaling pathway is hypothesized to be a bacterial regulatory pathway of hopanoids that are common lipid components in bacteria and are structural analogs...
molecular fossils that are often lipid biomarkers. Molecules like sterols and hopanoids, membrane lipids found in eukaryotes and bacteria, respectively, can be...
on primordial hydrocarbons and die in that environment. For example, hopanoids are just parts of the bacterial cell wall present in oil as a contaminant...
substances familiar to all in the form of cholesterol in our cells. He studied hopanoids in particular, which are found in sedimentary rock materials. He then...
interesting characteristic of Z. mobilis is that its plasma membrane contains hopanoids, pentacyclic compounds similar to eukaryotic sterols. This allows it to...
distribution of hopanoid C-2 methyltransferase in the bacterial domain, and interpret their findings as indicating that Alphaproteobacteria evolved hopanoid C-2 methyltransferase...
Hodgkin–Huxley model Homeoviscous adaptation Homologous desensitization Hopanoids Howard Berg Hugh Herr Human leg Human skeletal changes due to bipedalism...
Neunlist S, Holst O, Rohmer M (March 1985). "Prokaryotic triterpenoids. The hopanoids of the purple non-sulphur bacterium Rhodomicrobium vannielii: an aminotriol...
and also may have increased the gelification processes, raising the pH. Hopanoids are abundant and an indicator of common bacterial activity. The vegetation...
component. In contrast, bacteria produce other cyclic triterpenoids such as hopanoids and their diagenetic products hopanes are utilized as bacterial biomarkers...
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