Steranes constitute a group of

alkane In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in whi ...

organic compounds with a

cyclopentane Cyclopentane (also called C pentane) is a highly flammable alicyclic compound, alicyclic hydrocarbon with chemical formula C5H10, C5H10 and CAS number 287-92-3, consisting of a ring of five carbon atoms each bonded with two hydrogen atoms above and ...

-fused hydrogenated

phenanthrene Phenanthrene is a polycyclic aromatic hydrocarbon (PAH) with formula C14H10, consisting of three fused benzene rings. It is a colorless, crystal-like solid, but can also appear yellow. Phenanthrene is used to make dyes, plastics, pesticides, expl ...

structure as the parent nucleus, and they derived from

steroid A steroid is an organic compound with four fused compound, fused rings (designated A, B, C, and D) arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes t ...

s or

sterol A sterol is any organic compound with a Skeletal formula, skeleton closely related to Cholestanol, cholestan-3-ol. The simplest sterol is gonan-3-ol, which has a formula of , and is derived from that of gonane by replacement of a hydrogen atom on ...

s via diagenetic and catagenetic degradation, such as

hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated ...

. They are found in sediments and sedimentary rocks in nature. Steranes are derivatives of

gonane Gonane (cyclopentanoperhydrophenanthrene) is a chemical compound with formula , whose structure consists of four hydrocarbon rings fused together: three cyclohexane units and one cyclopentane. It can also be viewed as the result of fusing a cyc ...

, the steroid nucleus which is also called "cyclopentanoperhydrophenanthrene". They have an androstane skeleton with a side chain at the C-17 carbon, constituting the scaffold of all sterols. Steranes are widely used as

biomarkers In biomedical contexts, a biomarker, or biological marker, is a measurable indicator of some biological state or condition. Biomarkers are often measured and evaluated using blood, urine, or soft tissues to examine normal biological processes, p ...

for the presence of

eukaryotes The eukaryotes ( ) constitute the domain of Eukaryota or Eukarya, organisms whose cells have a membrane-bound nucleus. All animals, plants, fungi, seaweeds, and many unicellular organisms are eukaryotes. They constitute a major group of ...

in past ecosystems because steroids are nearly exclusively produced by eukaryotes. In particular,

cholestanes Cholestane is a Saturated and unsaturated compounds, saturated tetracyclic steroid biosynthetically derived from triterpenoids. This 27-carbon biomarker is produced by diagenesis of cholesterol and is one of the most abundant biomarkers in the roc ...

are diagenetic products of cholesterol in

animals Animals are multicellular, eukaryotic organisms in the biological kingdom Animalia (). With few exceptions, animals consume organic material, breathe oxygen, have myocytes and are able to move, can reproduce sexually, and grow from a ...

, while stigmastanes are diagenetic products of stigmasterols in

algae Algae ( , ; : alga ) is an informal term for any organisms of a large and diverse group of photosynthesis, photosynthetic organisms that are not plants, and includes species from multiple distinct clades. Such organisms range from unicellular ...

and

land plants The embryophytes () are a clade of plants, also known as Embryophyta (Plantae ''sensu strictissimo'') () or land plants. They are the most familiar group of photoautotrophs that make up the vegetation on Earth's dry lands and wetlands. Embryophy ...

. However, some bacteria are now known to produce sterols and it is inferred that the ultimate origin of sterol biosynthesis is in bacteria. Sterols are produced via protosterols that are direct cyclization compounds of

squalene Squalene is an organic compound. It is a triterpene with the formula C30H50. It is a colourless oil, although impure samples appear yellow. It was originally obtained from shark liver oil (hence its name, as '' Squalus'' is a genus of sharks). ...

by the catalysis of

oxidosqualene cyclase Oxidosqualene cyclases (OSC) are enzymes involved in cyclization reactions of 2,3-oxidosqualene to form sterols or triterpenes. There are two major groups of sterol-producing OSC enzymes: * Cycloartenol synthase (CAS), found in all plants, which ...

. All known sterols in eukaryotes are enzymatically extensively modified from protosterols, while organisms that only produce protosterols are not known. The oldest record of modified steranes are in sedimentary rocks deposited ca. 720–820 million years ago. In contrast, diagenetic products of protosterols (called protostanes and cyclosteranes) are widely distributed in older

Proterozoic The Proterozoic ( ) is the third of the four geologic eons of Earth's history, spanning the time interval from 2500 to 538.8 Mya, and is the longest eon of Earth's geologic time scale. It is preceded by the Archean and followed by the Phanerozo ...

rocks and imply the presence of extinct proto-eukaryotes and/or sterol-producing bacteria before the evolution of crown-group eukaryotes. Steranes may be rearranged to diasteranes during

diagenesis Diagenesis () is the process of physical and chemical changes in sediments first caused by water-rock interactions, microbial activity, and compaction after their deposition. Increased pressure and temperature only start to play a role as sedi ...

(C-27 to C-30, rearrangement at C-18 and C-19, no R at C-24). Oils from clastic source rocks tend to be rich in diasteranes.

Cholesterol Cholesterol is the principal sterol of all higher animals, distributed in body Tissue (biology), tissues, especially the brain and spinal cord, and in Animal fat, animal fats and oils. Cholesterol is biosynthesis, biosynthesized by all anima ...

and its derivatives (such as

progesterone Progesterone (; P4) is an endogenous steroid and progestogen sex hormone involved in the menstrual cycle, pregnancy, and embryogenesis of humans and other species. It belongs to a group of steroid hormones called the progestogens and is the ma ...

aldosterone Aldosterone is the main mineralocorticoid steroid hormone produced by the zona glomerulosa of the adrenal cortex in the adrenal gland. It is essential for sodium conservation in the kidney, salivary glands, sweat glands, and colon. It plays ...

cortisol Cortisol is a steroid hormone in the glucocorticoid class of hormones and a stress hormone. When used as medication, it is known as hydrocortisone. Cortisol is produced in many animals, mainly by the ''zona fasciculata'' of the adrenal corte ...

, and

testosterone Testosterone is the primary male sex hormone and androgen in Male, males. In humans, testosterone plays a key role in the development of Male reproductive system, male reproductive tissues such as testicles and prostate, as well as promoting se ...

), are common examples of compounds with the sterane scaffold.

References

Steroids Cholestanes {{steroid-stub

See also

References