por what is the cyclopentanoperhydrophenanthrene?
He cyclopentanoperhydrophenanthrene, estrane, sterane or gonane, is a hydrocarbon made up of several cyclic rings that make up the central skeleton of cholesterol and its hormonal derivatives, as well as some drugs and their derivatives. Plants and animals contain various compounds with cyclopentanoperhydrophenanthrene skeletons that have important functions in their life processes.
The pharmacological industry has been dedicated for decades to the investigation of the natural compounds of different organisms in search of active and effective ingredients for the development of medicines, pesticides and other chemical compounds.
In these investigations, some cyclopentanoperhydrophenanthrene esters or acids have turned out to be useful as active principles of therapeutic agents, which are used in combination with other substances for the treatment of certain types of pathologies and diseases.
Structure and characteristics of cyclopentanoperhydrophenanthrene
Cyclopentanoperhydrophenanthrene is a four-ring polycyclic hydrocarbon that results from the condensation of a cyclopentane nucleus with a phenanthrene. This is considered a product of total saturation by hydrogenation of phenanthrene.
It is composed of 17 carbon atoms, and some natural derivatives always have two methyl groups at carbons 10 and 13, known as angular methyls.
The cyclopentanoperhydrophenanthrene molecule, together with the angular methyls, has six asymmetric carbons (5.10; 8.9; 13.14), so the compound has at least 64 isomers. However, most naturally occurring steroid derivatives only differ in stereoisomerism at carbons 5 and 10.
Compounds derived from cyclopentanoperhydrophenanthrene have highly hydrophobic behavior, since they have a central core of four interconnected cyclic rings that can function to repel water around them in aqueous media.
Occurrence in nature
sterols: cholesterol
The cyclic structure of cyclopentanoperhydrophenanthrene can be found in multiple compounds in nature.
Sterols are secondary alcoholic compounds whose main skeleton is the polycyclic ring of cyclopentanoperhydrophenanthrene. Among the best studied sterols is cholesterol.
Cholesterol is a solid alcohol with 27 carbon atoms that is found only in animals. It derives from a molecule known as cholestene, which comes from cholestane, formed by a double bond between carbons 5 and 6 of cholestene.
This compound has a side chain on the 17-position carbon and an OH group on the 3-position carbon.
Steroids, vitamins, and steroid hormones such as progesterone, aldosterone, cortisol, and testosterone are derived from cholesterol. These hormones, despite presenting great variations between their structures, maintain the cyclopentanoperhydrophenanthrene molecule as their central skeleton.
steroids
The basis of the structure of steroids is the four-ringed core of the cyclopentanoperhydrophenanthrene molecule. Natural steroids in mammals are synthesized primarily in the sexual organs, adrenal glands, and placenta, and are all derived from cholesterol.
Steroids are a varied group of compounds that are generally hormonal in nature or are vitamins that have carbonyl, hydroxyl, or hydrocarbon chain groups as substituent groups of the cyclopentanoperhydrophenanthrene skeleton.
Among the steroids are vitamin D and its derivatives. Some scientists classify cholesterol as a steroid.
In the brain, glial cells possess all the cellular machinery for synthesizing on site many neurosteroids necessary for its function.
steroid hormones
Steroid hormones are a large class of small lipophilic molecules that are synthesized in steroidogenic tissues and that act at their target sites to regulate a myriad of physiological functions of the endocrine system, including sexual and reproductive development.
Some steroid hormones are produced by the cells of the adrenal cortex, the «thecal» cells of the ovary, and the testicular Leydig cells. In the placenta, trophoblast cells synthesize large amounts of progesterone and estrogen, both steroid hormones.
Progesterone is a naturally occurring hormone that belongs to the family of progestogenic hormones. These promote the development of the ovaries in animals, which is why it is said that progesterone is the hormone responsible for secondary sexual development in the female sex.
Estrogens are hormones derived from estrane. These hormones are typical of the first half of the female sexual cycle and induce the formation of organs such as the breasts and ovaries.
Being steroid hormones, the structure of progesterone and estrogen consists of a central skeleton of cyclopentanoperhydrophenanthrene that varies only in the ketone and oxygen functional groups.
use in industry
In the pharmaceutical industry, numerous drugs have been developed using the cyclic skeleton of cyclopentanoperhydrophenanthrene or cholesterol derivatives as the main structure.
Such is the case of levonorgestrel, a progestin used in contraceptive formulations, which has an activity 80 times more powerful than the body’s natural progesterones. This drug has an androgenic effect, as it competes with testosterone to activate the progesterone-binding protein.
Many corticosteroids, such as cortisone, hydrocortisone and prednisone, are currently used for the treatment of different inflammatory conditions, skin eruptions, for the treatment of asthma and lupus. These compounds are synthetic steroids that mimic the effects of many hormones produced by the adrenal glands.
Dehydroepiandrosterone is a synthetic testosterone precursor steroid hormone, marketed as a pre-hormone nutritional supplement, commonly known as andros. As a curious fact, in 1998 the sales of this drug skyrocketed after the doping of Mark McGwire, who was at the time the record holder for home run in major league baseball.
Importance of Cyclopentanoperhydrophenanthrene
The importance of the cyclopentanoperhydrophenanthrene skeleton lies in its presence as a fundamental part of various molecules in nature.
Cholesterol is an important constituent of biological membranes and of lipoproteins of an amphipathic nature. It is a precursor in the synthesis of vitamin D, steroid hormones and bile acids.
Vitamin D has an important role in lowering the risk of chronic diseases, including various types of cancer, autoimmune diseases, and cardiovascular diseases. Humans acquire this compound by exposure to sunlight or through food ingested in the diet.
The processing of vitamin D is related to the levels of the parathyroid hormone, therefore it is closely linked to the body’s metabolism in humans.
Phytosterols are bioactive plant compounds analogous to cholesterol in animals that have a four-ring molecular structure derived from cyclopentanoperhydrophenanthrene.
These compounds are present in plants and differ from each other by the number of carbon atoms and the nature of their side chain. Crude palm oil, widely used in various industries, including the food industry, is rich in this type of sterols.
References
Hughes, R., Newsom-Davis, J., Perkin, G., & Pierce, J. Controlled trial of prednisolone in acute polyneuropathy. The Lancet.
Paul, S., & Purdy, R. Neuroactive steroids. The FASEB Journal.
Holick, M. F. Vitamin D Deficiency. The New England Journal of Medicine.
Russell, D. Cholesterol Biosynthesis and Metabolism. Cardiovascular Drugs and Therapy.